MXPA00005100A - Imidazole derivatives having an inhibitory activity for farnesyl transferase and process for preparation thereof - Google Patents

Abstract

The present invention relates to a novel imidazole derivative represented by formula (1) which shows an inhibitory activity against farnesyl transferase or pharmaceutically acceptable salts or isomers thereof, in which A, n1 and Y are defined in the specification;to a process for preparation of the compound of formula (1);to intermediates which are used in the preparation of the compound of formula (1);and to a pharmaceutical composition comprising the compound of formula (1) as an active ingredient.

Description

DERIVATIVES ^ OF OgDAZOL THAT PRESENT AN ACTIVITY -CNHIBITORIfli AGAINST EARNESIL TRANSFERASE AND A PROCEDURE FOR PREPARATION DESCRIPTION OF THE INVENTION The present invention relates to a novel imidazole derivative represented by the formula (1) illustrated below and having an inhibitory activity against farnesyl trans ferase: wherein A, nx and Y are defined according to what will be described below, or pharmaceutically acceptable salts or isomers thereof. In addition, the present invention relates to a process for the preparation of the compound of the formula (1), to the intermediates which are used in the preparation of the compound of the formula (1), and to a pharmaceutical composition comprising the compound of the Formula (1) as an active ingredient. Ras proteins from mammals act as switches to indicate events associated with cell growth and differentiation. The proto-oncogene family of ras consists of three members, N-, K-, and H-ras, which encode the 4 highly homologous types of proteins; that is, the ti, N-ras proteins of the 189 residues and the two isomorphic proteins K-ras-4B and K-ras-4A of 188 and 189 residues, respectively. The chemical basis for the switch mechanism comprises the cycling of the protein in the bound state of inactive guanosine diphosphate (GDP) (turned off) and the bound state of active guanosine triphosphate (GTP) (switched on) (Boourne, HR; Sanders, DA; McCormick, F., Nature, 1991, 349, 117). Biochemical and structural studies have shown that point mutations of residues 12, 13 and 61, located in the area close to the phosphoryl base of GTP that result in a reduction in the activity of guanosine triphosphatase are associated with many human cancers, in particular, with pancreatic cancer, urinary bladder carcinoma, colon cancer, etc. (Bos, J. I., Cancer Res., 1989, 49, 4682). The Ras protein is synthesized as a cytosolic precursor that is finally found on the cytoplasmic side of the plasma membrane after a series of post-translational modifications (Gibbs, J.B., Cell 1991, 65 1). This series of biochemical modifications, by means of changes in the state of the electric charge or the spatial structure to increase the hydrophobicity, allow the Ras protein to bind to the cell membrane more easily. The first obligatory step in the series is the addition of a farnesyl moiety in the cysteine residue of the C-thermal CAAX motif (C, cysteine; A, generally an aliphatic residue; X, any other amino acid) in a reaction catalyzed by the farnesil protein transferase (FTase). This modification is essential for the Ras function, as demonstrated by the inability of the Ras mutants lacking the C-terminal cysteine to be farnesilar to be located in the plasma, and to transform the mammalian cells into culture (Hancock, JF, Magee, AI, Childs, JE, Marshall, CJ, Cell 1989, 57, 1167). Subsequent postranslational modifications, the • 5 fragmentation of the AAX residues, the carboxyl methylation of the farnesylated cysteine, and the palmitoylation of the cysteines located upstream of the CAAX motif in the H- and N-ras proteins that are not mandatory for the Ras membrane association or an activity of cellular transformation. Interestingly, K-ras-48, different from H- and N-ras, possesses a region rich in multiple lysine which is called polybasic domain instead of having the cysteine necessary for palmitoylation, which is why makes it easier for farnesylated ras protein to bind the anionic lipid layer of the cell membrane. Therefore, it has been suggested to inhibitors of Ftasa that catalyzes the obligatory modification as anticancer agents for tumors in which the Ras oncogene contributes in the transformation (Buses, J. E. collaborators, Chemistry & Biology, 1995, 2, 787). A great • number of identified FTase inhibitors renciently demonstrated a potent specific ability to block farnesylation, signaling and Ras transformation in transformed cells and in the lines of tumor cells in vitro and in animal models (Kohl, NE and their collaborators, Nati, Acad. Sci., USA, 1994, 91, 9141; Kohl, NE and their collaborators, Nature Medicine, 1993, 1, 792).

However, most inhibitors are related to the CAAX motif as a mimic of the Ras substrate motif and are peptidic in nature or contain a sulfhydryl group (USP No. 5,141,851; Kohl, NE and co-workers, Science, 1993, 260, 1934; PCT / US95 / 12224, Graham and their collaborators; Sebti, SM and their collaborators, J. Biol. Chem., 1995, 270, 26802; James, GL and his collaborators, Science, 1993, 260, 1937, Bishop, WR and their collaborators, J. Biol. Chem., 1995, 270, 30611). Recently, a new type of peptidomimetic inhibitor that mimics the catalytic passage of Ftase has been reported (Poulter, C. D. et al., J. Am. Chem. Soc, 1996, 118, 8761). The chemical basis of the inhibitor design is related to the reaction mechanism. That is, the transfer of the prenyl group by means of the enzyme is the electrophilic displacement and the reaction requires a charge (+) in a transition state. However, these above-described inhibitors possess limited activity and selectivity for the inhibition of the oncogenic function of Ras proteins, in particular, K-ras-4B, which was found to be more common in human cancer. Accordingly, a new inhibitor is required which possesses the ability to effectively inhibit K-ras activity. With regard to restenosis and proliferative vascular diseases, it has been shown that the inhibition of cellular ras prevents the proliferation of smooth muscle after vascular injury in vivo (Indolfi C. et al., Nature Med., 1995, 1 (6), 541, 545).

Definitely, this report supports the role of farnesyl transferase inhibitors in this disease, and presents the inhibition of the accumulation and proliferation of vascular smooth muscle. The inventors of the present have carried out studies to develop a compound possessing the structural characteristics that mimic an intermediate state of the catalytic reaction of the FTase and as a result, they discovered that the imidazole derivatives according to the present invention can inhibit the enzyme in potent form. Therefore, the object of the present invention is to provide an imidazole derivative of the formula (1) which inhibits the activity of the Ftase, a process for its preparation and a. intermediary which can be used effectively for the preparation of the compound of the formula (1). It is another object of the present invention to provide a pharmaceutical composition comprising the compound of the formula (1) as an active ingredient. The first object of the present invention is to provide an imidazole derivative represented by formula (1) which is represented below, which inhibits the activity of farnesyl transferase: wherein: ni represents an integer ranging from 1 to 4, A represents hydrogen, straight or branched chain C1-C10 alkyl which may be optionally substituted by C3-C7 cycloalkyl or lower alkoxy; or 'a radical that is selected from the following group: where; a and Ri ', independently from each other, represent hydrogen, halogen, cyano, nitro, hydroxycarbonyl, aminocarbonyl, aminothiocarbonyl, lower alkoxy, phenoxy, phenyl, benzyloxy, or lower alkyl which may be optionally substituted by C3-C6 cycloalkyl, R2 represents hydrogen or lower alkyl, or represents -EF, where E is -CH2-, -C (O) or -S (0) 2- 'and F is hydrogen; lower alkyl which may be optionally substituted by phenoxy or biphenyl; lower alkoxy which may be optionally substituted by aryl; phenyl; benzyl; benzyloxy; or amino which may be optionally substituted by lower alkyl, benzyl or C5-C6 cycloalkyl, R3 represents hydrogen, alkyl or lower phenyl, R represents a radical selected from the group indicated below: where: n2 and n3 / independently of each other, denote 0, 1, 2, 3 or 4, Rs and R9. independently of one another, they represent hydrogen, lower alkyl, lower alkoxy, phenoxy, phenyl, hydroxy or halogen, R5 and Rs, independently of each other, represent hydrogen, lower alkyl, lower alkoxy, phenoxy, phenyl, cyano, hydroxy or halogen, R7 represents hydrogen, lower alkyl which may be optionally substituted by C3-Cg cycloalkyl; lower alkoxy; hydroxy; C3-Cs cycloalkyl; di (lower alkyl) amino; phenyl; phenoxy; or halogen, Rio represents, hydrogen, lower alkyl or lower alkoxy, Y represents a radical selected from the group indicated below: wherein: X represents O or S, B represents hydrogen or lower alkyl which may be optionally substituted by hydroxy, mercapto, lower alkoxy, lower alkylthio or arylc, C represents hydrogen or lower alkyl which may be optionally substituted by aryl; or represents a radical selected from the group indicated below: where Rn and R12 # independently from each other, represent hydrogen, lower alkyl, lower alkoxy, halogen, cyano, hydroxycarbonyl, amino, carbonyl, aminothiocarbonyl, hydroxy, phenyl or phenoxy, R13 and? 4 / independently from each other, represent hydrogen, lower alkyl, aryl or -fíCH? rX-Ru where X is defined as described above, n is an integer ranging from 2 to 4 and Ri5 is lower alkyl, D represents an amino acid residue or lower alkyl ester of an amino acid residue; or represents a radical that is selected from the following group: where Ro is defined according to what was described above, Q represents O, S, S = 0 or S02, Z represents O, S, S = 0, S02, C = 0 or C = S, or represents CH-R2o or N -R20 (where R2o is hydrogen, lower alkyl or hydroxy), ns denotes an integer ranging from 1 to 3, Ri6 and i7, independently of each other, represents hydrogen; aryl, lower alkyl which may be optionally substituted by aryl or cyanoaryl; or (CH2) p? -Q-H where n4, Q and Rio are defined as described above, Ris and Ri9. independently of each other, they represent hydrogen; halogen; hydroxy; cyano; lower alkyl; lower alkoxy; alkoxyalkyl; alkylthio; hydroxycarbonyl; aminocarbonyl; aminothiocarbonyl; alkylsulfonyl; alkylthioalkyl; alkylthioalkyloxy; aril; or oxy, thio, sulfonyl or lower alkyl substituted by aryl, G represents a radical? uß is selected from the group indicated below: where R n and 2 2 are defined as described above, I represents lower alkoxy or represents a radical selected from the following group: where he laughs 17 and Z are defined as safe, as described above, L represents a radical selected from the following group: - + LJ * - where Z and Q are defined as described above, provided that (1) n2 is different from 0 when R3 is hydrogen, and (2) And it's different from when A is or the pharmaceutically acceptable salts or isomers thereof. In particular, the compound according to the present invention has a structure completely different from that of the known inhibitors for farnesyl transferase, and likewise, it never includes the thiol moiety. In the definitions for the substituents of the compound of the formula (1), the term "lower alkyl" refers to a straight or branched chain alkyl having between 1 and 4 carbon atoms and including methyl, ethyl, isopropyl, isobutyl and t-butyl. Since the compound of the formula (1) according to the present invention can have asymmetric carbon atoms according to the substituents, it can be present in the form of an R or S isomer, a racemate or mixtures thereof. In this way, the present invention also includes all these stereoisomers and their mixtures. Additionally, the compound of formula (1) according to the present invention can form a pharmaceutically acceptable salt. Said salt includes a non-toxic acid addition salt containing a pharmaceutically acceptable anion, for example a salt with inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, iodhydric acid, etc., a salt with organic carboxylic acids such as tartaric acid, formic acid, citric acid, acid acetic acid, trichloroacetic acid, trifluoroacetic acid, gluconic acid, benzoic acid, lactic acid, fumaric acid, maleic acid, asparagic acid, etc., or a salt with sulfonic acids such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, naphthalenesulfonic acid , etc.; a base addition salt, for example a salt with pyridine or ammonia; and a metal addition salt, for example a salt with alkali metal or alkaline earth metal such as, for example, lithium salt. Also, the present invention includes a solvate of the compound of the formula (1) such as, for example, an alcoholate or hydrate thereof. They can be produced following conventional conversion methods. Among the compounds of the formula (1) according to the present invention, the compounds that are preferred include all those in which: ni represents an integer ranging from 1 to 3, A represents hydrogen; C1-C10 straight or branched chain alkyl which may be optionally substituted by C3-C7 cycloalkyl or lower alkoxy or a radical selected from the group included below: where R1 and Ri ', independently of each other, represent hydrogen, halogen, cyano, nitro, hydroxycarbonyl, aminocarbonyl, aminothiocarbonyl, lower alkoxy, phenoxy, phenyl, benzyloxy, or lower alkyl which may be optionally substituted by C3-C6 cycloalkyl, R2 'represents hydrogen or lower alkyl, or represents -EF, where E is -CH2-, -C (O) or -S (O) 2- and F is hydrogen; lower alkyl which may be optionally substituted by phenoxy or biphenyl; lower alkoxy which may be optionally substituted by aryl; phenyl; benzyl; benzyloxy; or amino which may be optionally substituted by lower alkyl, benzyl or C5-C6 cycloalkyl, R3 represents hydrogen or lower alkyl, R4 represents a radical selected from the group indicated below: -HCH? ni - | - < CH_) r $ --CHíJn¡j- where n2 and n3 / independently of each other, denote 0, 1, 2, 3 or 4, Rs, Re, Rs and R9. independently of one another, they represent hydrogen, lower alkyl, lower alkoxy, phenoxy, hydroxy or halogen, R7 represents hydrogen, lower alkyl which may be optionally substituted by C3-C6 cycloalkyl, "lower alkoxy, hydroxy; C3-Cg cycloalkyl; halogen, Rio represents hydrogen, methyl or methoxy; Y represents a radical selected from the group indicated below: wherein: X represents 0 or S, B represents hydrogen or lower alkyl which may be optionally substituted by lower alkoxy or aryl, C represents hydrogen or lower alkyl which may be optionally substituted by aryl; or represents a radical selected from the group indicated below: where R p and R 2, independently of each other, represent hydrogen, lower alkyl, lower alkoxy, halogen, cyano, aminocarbonyl, phenyl or phenoxy, R 13 and 14, independently from each other, represent hydrogen, lower alkyl, aryl or -ÍCH? G * -RIS where X is defined as described above, n is 2 and Ris is lower alkyl, D represents an amino acid residue or a lower alkyl ester of an amino acid residue; or represents a radical that is selected from the following group: where: Rio is defined according to what was described above, Q represents O, S, S = 0 or S02, Z represents O, S, S = 0, S02, C = 0 or C = S, or represents CH-R20 or N-R20 (where R2o is hydrogen, lower alkyl or hydroxy), ns denotes an integer ranging from 1 to 3, i6 and Ri7, independently of each other, represent hydrogen; aryl, lower alkyl which may be optionally substituted by aryl or where n4, Q and Rio are defined as described above, Ris and Rig, independently of each other, represent hydrogen; halogen; hydroxy; cyano; lower alkyl; lower alkoxy; alkoxyalkyl; alkylthio; hydroxycarbonyl; aminocarbonyl; aminothiocarbonyl; alkylsulfonyl; alkylthioalkyl; alkylthioalkyloxy; aril; or oxy, thio, sulfonyl or lower alkyl substituted by aryl, G represents a radical selected from the group indicated below: where: Rn and R12 are defined as described above, I represents lower alkoxy or represents a radical selected from where: laugh 17 and Z are defined as described above, L represents a radical selected from the following group: where Z and Q are defined as described above, provided that (1) n2 is different from 0 when R3 is hydrogen, and [2) Y is different from when A is Particularly preferred compounds include all those in which Y represents: and C represents Some typical examples of the compound of the formula (1) according to the present invention are presented in Table 1 below.

Table 1-1 COM. COM. TRUCTURE NO. STRUCTURE IS NO.

Table 1-2 • Table 1-3 Table 1-4 Table 1-5 Table 1-6 Table 1-7 Table 1-8 Table 1-9 Table 1-10 Table 1-11 Table 1-12 Table 1-13 Table 1-14 Table 1-15 Table 1-16 Table 1-17 Table 1-18 Table 1-19 Table 1-20 Table 1-21 It is another object of the present invention to provide processes for preparing the imidazole derivative of the formula (1) as defined above. According to the present invention, the imidazole derivative of the formula (1) can be prepared following processes characterized in that: (a) a compound represented by the formula (2) which is included below is reacted in a solvent, in the presence of a base, with a compound represented by the formula (3) that is included below, and then the trityl group is removed from the product thus obtained in the presence of trifluoroacetic acid to produce a compound represented by the formula (cf. ) which is included below or Reaction Scheme 1 (b) a compound represented by the formula (4) which is presented below in a solvent, in the presence of a base, is reacted with the compound of the formula (3) to produce a compound represented by the formula given next (Ib); o Reaction scheme 2 (c) a compound represented by the formula (5) which is detailed below is reacted in a solvent, in the presence of a base, with the compound of the formula (3), the trityl group is removed from the product obtained therefrom. in the presence of trifluoroacetic acid to produce a compound represented by the formula (6) which is included below, and subsequently the hydrogenation reaction is carried out to produce a compound represented by the formula (le) which is included below; o Reaction scheme 3 (d) a compound represented by the formula (7) which is included below is hydrolyzed to produce a compound represented by the formula (8) which is included below which is subsequently reacted with a compound represented by the formula (9) ) which is then included in the presence of a coupling agent to produce a compound represented by the formula (Id) which is included below; o Reaction scheme 4 (e) the carbonyl group is converted into a compound represented by the formula (le) which is detailed below in the thiocarbonyl group in the presence of a sulfurizing agent to produce a compound represented by the formula (I) which is presented below; o Reaction scheme 5 (f) a compound represented by the formula (lg) which is presented below is coupled in a solvent with a compound represented by the formula (10) to produce a compound represented by the formula (lh); or Reaction scheme 6 (g) a compound represented by the formula (11) which is included in an inert solvent is cyclized to produce a compound represented by the formula (Li); o Reaction scheme 7 (h) the amide group is converted to the compound of the formula (11) in the thioamide group to produce a compound represented by the formula (12) which is included below and which is subsequently cyclized in an inert solvent to produce a compound represented by the formula (Ij) which is included below; o Reaction scheme 8 (i) a compound represented by the formula (13) which is included below is reacted in a solvent with a compound represented by the formula (14a) which is then included to produce the compound of the formula (Ij); o Reaction scheme 9 (j) the compound of the formula (13) is reacted in a solvent with a compound represented by the formula (14b ") which is included below to produce a compound represented by the formula (lk) which is included below; o Reaction scheme 10 (k) a compound represented by the formula (11) is hydrolyzed in the presence of a base and the product obtained in this manner is reacted in a solvent in the presence of a coupling agent with a compound represented by the formula (15) which it is included below to produce a compound represented by the formula (Im); o Reaction scheme 11 (1) a compound represented by the formula (16) which is included below is reacted in a solvent, in the presence of a base, with a compound represented by the formula (17) which is included below to produce a compound represented by the formula (ln) that is included next; o Reaction scheme 12 (m) a compound represented by the formula (18) which is then included in a solvent, in the presence of a base, is reacted with the compound of the formula (17) and deprotected to produce a compound represented by the formula (I) which is included below which is subsequently coupled with a compound represented by the formula (19) which is included below to produce a compound represented by the formula (Ip) which is presented below: Diagram of reaction 13 in the above reaction schemes A, N, B, C, X, D, Ri6, R? , R 2, G, I, L, E and F are defined as described above, I 'represents lower alkoxy, I "is identical to I except that lower alkoxy is not included, T represents hydroxy or a reactive leaving group, preferably halogen , Tr represents trityl, Cbz represents benzyloxycarbonyl and has the same meaning throughout the present specification, however, the compound according to the present invention can be conveniently prepared by following any of the methods designed by combining the various Synthetic routes known from the prior art and, said combination can be easily carried out by any person skilled in the art, Procedures (a) to (m) will be explained in more detail later in the procedures (a) to (a). e) to carry out the preparation of the compound according to the present invention, any of the inert solvents which do not affect the adv the reaction and, preferably, one or more of those selected from the group consisting of: dimethylformamide, dimethylacetamide, ethanol, water, methylene chloride, chloroform, tetrahydrofuran and N-methylpyrrolidinone. As the base, one or more of those selected from the group consisting of sodium hydride, potassium hydroxide, potassium carbonate, potassium t-butoxide, sodium amide, sodium bis (trimethylsilyl) amide and bis can be mentioned. potassium (trimethylsilyl) amide and, more preferably, sodium hydride or potassium hydroxide. As the coupling agent used in the process for reacting the compound of the formula (8) with the compound of the formula (9), a mixture of 1-hydroxybenzotrizol and one or more of the substances selected from the group consisting of carbodiimides such as dicyclohexylcarbodiimide (DCC), l-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDC), 1,1 '-dicarbonyl-diimidazole (CDI), etc., and an inorganic dehydrating agent such as silicone tetrachloride. Among them, a mixture of 1-ethyl-3- (3-dimethyl-aminopropyl) carbodiimide (EDC) and 1-hydroxybenzotrizol hydrate is particularly preferred.

The sulfurizing agent used in the preparation of the compound of the formula (I) from the compound of the formula (le) includes 2,4-bis (phenylthio) -1,3-dithia-2,4-diphosphatane-2, 4-disulfide, Lawesson's reagent and PS? O. More preferably, 2,4-bis (phenylthio) -1,3-dithia-2,4-diphosphatane-2,4-disulfide can be used. The compound of the formula (lg) which is used as an initial material in the process (f) can be prepared by deprotecting the corresponding compound which is protected by a benzyloxycarbonyl group at the 1-position of the piperidine moiety. The deprotection reaction can be carried out by the application of conventional reaction conditions, preferably using Pd (OH) 2 / C or Pd / C in an alcohol solvent in a hydrogen atmosphere. The compound of the formula (lg) obtained in this manner is coupled to the compound of the formula (10) in an inert solvent, as mentioned above, optionally in the presence of a tertiary amine base to produce the compound of the formula (Ih). Alternatively, it is possible to react the compound of the formula (lg) in the presence of a coupling agent as mentioned for process (d) with the carboxylic acid derivative (T = OH) to produce the compound of the formula (lh) in the form of amide. In the cyclization reactions of (g) and (h) for the preparation of the compounds (li) and (lj), any solvent and, preferably, one or more of those selected from tetrahydrofuran and ethanol can be used. As the sulphidation agent used in the process of converting the amide group to thioamide in the process (h), there may be mentioned 2,4-bis (phenylthio) -1,3-dithia-2,4-diphosphatane-2, 4-disulfide, Lawesson's reagent or PS? O and, preferably, the Lawesson reagent. In processes (i) and (j) for the preparation of the compounds (lj) and (lk), by reacting the compound of the formula (13) with the compound of the formula (14a) or (14b), they can use one or more solvents selected from ethanol and isopropyl alcohol. Additionally, a common organic base can be used, such as, for example, one or more of those selected from a group consisting of lithium hydroxide, sodium hydroxide and potassium hydroxide and, preferably, lithium hydroxide can be used in the process (k) in which the compound of the formula (11) is hydrolyzed and then reacted with the compound of the formula (15) to produce the compound of the formula (lm). As the coupling agent, those mentioned for process (d) can be used. In processes (1) and (m), any inert solvent and, preferably, one or more of those selected from dimethylformamide and dimethyl acetamide can be employed as the solvent and, as the base, one or more of the which are selected from the group consisting of sodium hydride, sodium amide, sodium bis (trimethylsilyl) amide and potassium bis (trimethylsilyl) amide. The deprotection reaction in the process can be carried out under conventional reaction conditions for deprotection, preferably in the presence of Pd / C or Pd (OH) 2 / C in a hydrogen atmosphere. The coupling used for the combination of the compound of the formula (I) with the compound of the formula (19) can be the same as that mentioned for process (d) .The compound of the formula 3, used as the intermediate In the procedures for the preparation of the compound of the formula (1) according to the present invention, it is in itself a new compound, accordingly, it is another object of the present invention to provide The compound of the formula (3). As it is presented in reaction Schemes 14 to 16 which are included below, the compound of the formula (3) can be prepared by a process which is characterized in that the compound is reacted represented by the formula (20) which is included below in a solvent, in the presence of a coupling agent, with a compound represented by the formula (21! following; the compound of the formula (20) is reacted in a solvent, in the presence of dimethylformamide (DMF), with thionyl chloride to produce a compound represented by the formula (20a) which is included below and after which the compound is reacted of the formula (20a) obtained in this manner in a solvent with the compound of the formula (21); or a compound represented by the formula (3a) which is then included in a solvent is oxidized to produce a compound represented by the formula (3b) which is included below. Reaction scheme 14 Reaction scheme 15 Reaction scheme 16 In Reaction Schemes 14, 15 and 16 above B, C, and D are defined as described above, Qa represents S or S = 0. In the aforementioned processes, according to Reaction Schemes 14 to 16 for the preparation of compound (3), any of the inert solvents and, preferably, one or more of those selected from dimethylformamide, dimethylacetamide, chloride are used. of methylene, tetrahydrofuran and 1,2-dichloroethane as the solvent. As the coupling agent in Reaction Scheme 14, there may be mentioned a mixture of 1-hydroxybenzotrizol and one or more substances which are selected from the group consisting of carbodiimides such as dicyclohexylcarbodiimide (DCC), l-ethyl-3- ( 3-dimethylamino-propyl) carbodiimide (EDC), etc. Among them, the one which is particularly preferred is a mixture of l-ethyl-3- (3-dimethylaminopropyl) carbodiimiide (EDC) and 1-hydroxy-benzotrizol hydrate. The dimethylformamide in the procedure of Reaction Scheme 15 is used in a catalytic amount. In addition, the excess of metachloroperbenzoic acid is preferably used as the oxidant in the process according to Reaction Scheme 16. However, it is possible to select the coupling agent, the oxidant, the solvent, the catalyst, etc. suitably among others other than those mentioned above for the purpose that the reaction can be carried out. And the reaction conditions that include the amount of reagents, the reaction temperature, the reaction time, etc. they can be determined easily by any person skilled in the art according to the specific reagents. Since the compound of the formula (8) which is used as an intermediate for preparing the compound of the formula (Id) in the process (d) is also a new compound as well as the compound of the formula (3) and, it is another object of the present invention to provide the intermediate compound of formula (8). It can be obtained by thihydrolyzing the compound of the formula (7). On the other hand, the initial materials used in the aforementioned processes can be prepared according to the specific procedures that are described in Reaction Schemes 17 to 29 which are detailed below. First of all, the compound of the formula (2) can be obtained by protection and halogenation according to what is presented in the reaction Scheme 17 which is included below.

The compound of the formula (4) in which A 'is 4-cyan-benzyl can be synthesized by means of protection, acetylation, coupling, deprotection and halogenation as presented in the reaction Scheme 18 included then. Most often, compound (4) is prepared following a procedure in which an amine compound is reacted with dihydroxyacetone to produce a mercaptoimidazole derivative, which is then distilled and halogen as presented in Reaction Scheme 19 It is included below. Reference may be made to J. Med. Chem. , 33, 1312-1329, 1990, in which a similar reaction is explained in greater detail to see the specific reaction conditions. Reaction scheme 18 Reaction scheme 19 The amine compound used in Reaction Scheme 19 above, wherein A represents 1- (benzyloxycarbonyl) piperidin-4-ylmethyl can be synthesized from -aminomethylpiperidine by protection, benzyloxycarbonylation and deprotection according to what is presented in the reaction Scheme 20 In Reaction Scheme 20 cited above: CbzCl represents benzylchloroformate and has the same meaning throughout the present specification. The compound of the formula (5) can be synthesized by esterification, protection, reduction and halogenation according to what is presented in the following Reaction Scheme 21. Reaction scheme 21 in Reaction Scheme 21 above, DIBAL represents diisobutylaluminum hydride. Also, in Reaction Scheme 21 above, it is possible to reduce the alcohol compound obtained before preparing the final chloride compound in a conventional manner and then it can be reacted with thionyl chloride to produce the compound of the formula (2) where neither is 3. The compound of the formula (20) used as the initial mater-Lal in the preparation of the intermediate of the formula (3) can be prepared, for example, according to the procedure described in Reaction Scheme 22 which is included below, a procedure performed from 1-naphthaldehyde. In particular, the intermediate of the formula (3) in which D is 1-naphthyl can be conveniently synthesized according to Reaction Schemes 23 and 24 which are included below. Reaction scheme 22 Reaction scheme 23 Reaction scheme 24 The compound of the formula (11) used as the starting material in the process (g) can be prepared by coupling a hydrochloride salt of a glycinate derivative with a hydrochloride salt of 4-imidazoleacetic acid, as represented in Reaction scheme 25. As the coupling agent, those mentioned in process (d) can be used. Meanwhile, the compound of the formula (13) used in the process (i) can be prepared according to the procedure described in the following reaction Scheme 26, in which the chloride derivative obtained is used. in the procedure of Reaction Scheme 19 as the initial material. Reaction scheme 25 Reaction scheme 26 t UC1 NiC iülMSet E? E3 The compounds (14a) and (14b) employed in the processes (i) and (j) can be prepared according to Reaction Schemes 27 and 28, respectively. First, the compound of the formula (14a) can be synthesized by reacting an aldehyde derivative with methyl dichloroacetate in the presence of potassium t-butoxide. The compound of the formula (14b) in which I is I 'can be synthesized by reacting a ketone derivative with dialkylcarbonate in the presence of sodium hydride, and subsequently by reacting the product obtained in this manner with sulfuryl chloride. Reaction scheme 27 Reaction scheme 28 EE27? 3 Finally, the reagent of formula (17) can be prepared in processes (1) and (m) where G represents 1-naphthyl and L represents N-methyl-N- (2-methoxyethyl) amino from of 1-naphthaldehyde according to Reaction Scheme 29 which is included below. The other compounds (17) possessing different substituents can also be prepared according to Reaction Scheme 29. Reaction Scheme 29 The compound of the formula (1) prepared according to the aforementioned methods exhibits an inhibitory activity against farnesyl transferase and, thus, can be used effectively as an anticancer agent. Therefore, the present invention also provides a pharmaceutical composition comprising the novel compound of formula (1), as defined above, or a pharmaceutically acceptable salt or isomer thereof as an active ingredient together with a pharmaceutically carrier acceptable. In particular, the compound of the formula (1) can be used very effectively for the treatment of cancer, restenosis, atherosclerosis and infections caused by hepatitis delta and related viruses. When the active compound according to the present invention is used for clinical purposes, it is preferably administered in an amount between 10 mg and 100 mg per kg of body weight per day. The total daily dosage may be administered once or several times. However, the specific administration dose for the patient may vary with the specific compound used., the body weight of the individual patient, sex, hygienic conditions, diets, time or method of administration, the rate of excretion, the mixing ratio of the agent, the severity of the disease to be treated, etc. The compound of the present invention can be administered in the form of injections or oral preparations. Injections, for example, sterilized in an aqueous or oily suspension for injections, can be prepared according to the known method employing suitable dispersing agents, wetting agents or suspending agents. Solvents that can be employed for the preparation of injections include water, Ringer fluids and NaCl solution, and sterilized fixative oil can also be conveniently employed as the solvent or suspending medium. Any non-stimulating fixative oil including mono- or di-glyceride can be used for this purpose. Also, a fatty acid, for example oleic acid, can be used for the injections. As the solid preparation for oral administration, there may be mentioned capsules, tablets, pills, powders and granules, etc. and, preferably, capsules and tablets. It is also convenient that the tablets and pills are formulated as an enteric coated preparation. The solid preparations can be prepared by mixing the active compound of the formula (1) according to the present invention with at least one carrier selected from the group consisting of inactive diluents such as sucrose, lactose, starch, etc., lubricants such as magnesium stearate, disintegrating agents and binding agents. Next, the present invention will be explained more specifically in the following examples. However, it should be understood that the examples that follow are intended to illustrate the present invention but in no way limit the scope of the present invention. In addition, the procedures for preparing the starting substances that are used for the purpose of obtaining the compound of the formula (1) in the Preparations presented below will be explained in greater detail. Preparation 1: Synthesis of 1- (3,4-melenedi-dioxybenzyl) -5-chloromethyl-1H-imidazole 1 -1) 1- (3,4-methylenedioxybenzyl) -5-hydroxymethyl-1H-imidazole hydrochloride carried out a modified method of J. Med. Chem. , 33, 1312-1329, 1990 using dihydroxyacetone dimer and piperonylamine as starting materials. 1.37 g (10 mmol) of piperonylamine, 1.08 g (5.5 mmol) of dihydroxyacetone dimer and 1.15 g (11 mmol) of potassium thiocinate in 10 ml of isopropyl alcohol were introduced and then of this, 2 ml of acetic acid were added and the mixture was reacted at room temperature for 48 hours. The reaction mixture was filtered and the residual solid obtained in this manner was washed with 5 ml of isopropyl alcohol (x2) and with 5 ml of water (x2). The filtered solid was introduced into 12.5 ml of 10% aqueous nitric acid solution and the resulting solution was cooled to 0 ° C. After adding 10 mg of sodium nitrite in the form of parts to the reaction solution, the mixture was reacted at room temperature for 1 hour. The aqueous solution was washed with 10 ml of ethyl acetate, basified and subsequently recrystallized to obtain 1.16 g (Yield: 50%) of the title compound. 1ti NMR (CDC13) d 4.45 (s, 2H), 5.13 (s, 2H), 5.97 (s, 2H), 6.70 (m, 2H), 6.78 (d, ÍH) , 6.95 (s, ÍH), 7.45 (s, HH) FAB 233 (M + H), Ci2H 2 2N203 1 -2) Chlorohydrate of 1- (3,4-methylenedioxybenzyl) -3- chloromethyl- 1H-imidazole 233 mg (1 mmol) of the compound prepared in Preparation 1-1) were dissolved in 3 ml of chloroform and subsequently 355 mg (3 mmol) of thionyl chloride were slowly added dropwise at 0 ° C. After stirring for 2 hours, the solvent was removed by distillation at reduced pressure and the remainder of the hydrochloride was removed in order to obtain the title compound in 95% yield. The product obtained in this manner was used directly in the next reaction without purification. Preparation 2: Synthesis of 1- (naphthalen-1-ylmethyl) -5-chloromethyl-1H-imidazole 2-1) hydrochloride 1 - (Naphthalen-1-ylmethyl) -5'-hydroxymethyl-1H-imidazole The compound of the title with a yield of 65% according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone and (naphthalen-1-ylmethyl) amine dimer were used as the starting materials. ? H NMR (CDC13) d 4, 44 (s, 2H), 5.42 (s, 2H), 6.78 (d, ÍH), 6.85 (s, ÍH), 7.25 (m, 1H), 7.35 (s, HH), 7.43 (m, 2H), 7.65 (d, HH), 7.68 (d, 1H), 8.02 (d, HH). FAB 239 (M + H), C? 5H? 4N20 2-2) Hydrochloride of 1- (naphthalene-1-methylmethyl) -5-chloromethyl-1H-imidazole The title compound was obtained in 90% yield of according to the same procedure followed for Preparation 1-2) using the compound prepared in Preparation 2-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 3: Synthesis of 1- ((R) -.-methylbenzyl) -5-chloromethyl-1H-imidazole 3-1) 1 - ((R) -a-methylbenzyl) -5-hydroxymethyl-1H-imidazole hydrochloride. The title compound was obtained with a yield of 60% according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone dimer and (R) - (+) -a-methylbenzylamine were used as starting materials. 2H NMR (CDC13) d 1.73 (d, 3H), 4.28 (s, ÍH) -, 4.43 (d, ÍH), 5.60 (m, ÍH), 6.75 (s, ÍH) ), 7.04 (d, 2H), 7.23 (m, 3H), 7.42 (s, ÍH). FAB 203 (M + H), C12H? 4N20 3-2) 1 - ((R) -a-methylbenzyl) -5-chloromethyl-1H-1-idazole hydrochloride The title compound was obtained in 90% yield of according to the same procedure followed for Preparation 1-2) using the compound to be prepared in Preparation 3-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 4: Synthesis of 1- ((S) -a-methyl-benzyl) -5-chloromethyl-1H-imidazole 4-1) hydrochloride 1 - ((S) -a-methylbenzyl) -5-hydroxymethyl-1H- imidazole The title compound was obtained in 55% yield according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone dimer and (S) - (+) - a-methylbenzylamine were used as starting materials. XH NMR (CDC13) d 1.73 (d, 3H), 4.28 (s, ÍH), 4.43 (d, ÍH), 5.60 (m, 1H), 6.75 (s, ÍH) , 7.04 (d, 2H), 7.23 (m, 3H), 7.42 (s, ÍH) FAB 203 (M + H), C? 2H? 4N20 4-2) Hydrochloride of 1 - (( S) -a-methylbenzyl) -5-chloromethyl-lH-imidazole The title compound was obtained in 94% yield according to the same procedure followed for Preparation 1-2) using the compound to be prepared in Preparation 4-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 5: Synthesis of 1-phenethyl-5-chlorome-1H-imidazole 5-1) -Fenethyl-5-hydroxymethyl-1H-imidazole hydrochloride Synthesis was obtained in 70% yield in accordance with the same procedure followed for Preparation 1-1) except that dihydroxyacetone dimer and phenethylamine were used as starting materials. 1ti NMR (CDC13) d 3.08 (t, 2H), 4.27 (t, 2H), 4.47 (s, 2H), 6.89 (s, ÍH), 7.05 (d, 2H) , 7.26 (m, 3H), 7.44 (S, ÍH). FAB 203 (M + H), CX2H? N20 5-2) l-phenethyl-5-chloromethyl-lH-imidazole hydrochloride The title compound was obtained in 90% yield according to the same procedure followed for Preparation 1-2) using the compound to be prepared in the ß ß Preparation 5-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 6: Synthesis of 3- [N- (1-methyoxyethyl) -N-methyl] carbamoyl-4- (naph alen-1-yl) -lH-pyrrole 6-1) Ethyl ester of 3- (Naphthalenic acid -1-yl) -acyclic 22.4 g (0.10 mol) of triethylphosphonoacetate were dissolved in 500 ml of acetonitrile, and slowly, 30.4 g (0.2 mol) of 1,8-diazabicyclo [5.4. 0] undec-7-ene (1, 5-5) (DBÜ). To this solution were slowly introduced 15.6 g (0.10 mol) of 1-naphthaldehyde dissolved in 20 ml of tetrahydrofuran and the mixture was stirred for 8 hours. The organic solvent was removed by distillation under reduced pressure. The resulting residue was dissolved in ethyl acetate, washed twice with water, dried in magnesium sulfate, concentrated, and then subjected to silica gel column chromatography (eluent: n-hexane / acetate). ethyl = 95/5, v / v) to obtain 20.3 g (0.090 mol, yield 90%) of the title compound. XH NMR (CDC13) d 1.33 (t, 3H), 4.10 (q, 2H), 6.75 (q, ÍH), 7.50 (m, 3H), 7.73 (d, ÍH) , 7.85 (m, 2H), 8.10 (d, ÍH), 8.21 (d, ÍH) FAB 227 (M + H) 6-2) 3- (Ethoxycarbonyl) -4- (naphthalen-1) -Il) -lH-pyrrole 4.3 g (18.9 mmol) of 3- (naphthalen-1-yl) -acrylic acid ethyl ester prepared in Preparation 6-1) and 3.68 g (18 g) were dissolved. , 9 mmol) of tosylmethylisocyanide in 100 ml of tetrahydrofuran. 2.55 g (22.7 mmol) of potassium t-butoxide dissolved in 100 ml of tetrahydrofuran were slowly added thereto and the mixture was refluxed for 30 minutes. 100 ml of water was introduced into the reaction solution to stop the reaction and the solvent was removed under reduced pressure. The reaction solution was extracted with diethyl ether, washed with aqueous sodium chloride solution, and then dried in magnesium sulfate. The solvent was removed under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate / n-hexane = 1/3, v / v) to obtain 3.85 g (14.3 mmol. , yield: 77%) of the title compound. XH NMR (CDC13) d 1.27 (t, 3H), 4.07 (q, 2H), 6.76 (s, ÍH), 7.28-7.47 (m, 5H), 7.59 ( s, ÍH), 7.82 (m, 2H), 9.99 (s, ÍH) FAB 266 (M + H) 6-3) 3-Hydroxycarbonyl -4- (naphthalen-1 -yl) -lH-pyrrole 2.64 g (10 mmol) of the compound prepared in Preparation 6-2) were dissolved in 50 ml of 50% ethanol and 2.24 g (40 mmol) of potassium hydroxide were added thereto. The reaction mixture was refluxed for 7 hours, cooled to room temperature, brought to pH 4-5, extracted with ethyl acetate and dried in sodium sulfate. The solvent was removed under reduced pressure to obtain 1.90 g (8.1 mmol, yield: 81%) of the title compound. The product obtained in this manner was used directly in the next reaction without purification. XH NMR (CDC13) d 6.60 (s, ÍH), 7.32-7.49 (m, 5H), 7.54 (s, ÍH), 7.84 (m, 2H), 9.92 ( s, ÍH) FAB 238 (M + H) 6-4) 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -IH-pyrrole 234 mg was dissolved ( 1 mmol) of the compound prepared in Preparation 6-3) in 2 ml of dimethylformamide and then 230 mg (1.2 mmol) of EDC, 101 mg (1 mmol) of triethylamine and 162 mg (1 mg) were added thereto. 2 mmol) of HOBT. The resulting mixture was stirred at 0 ° C for 5 minutes. 124 mg (1 mmol) of N- (2-methoxyethyl) -N-methylamine hydrochloride was added to the reaction solution, which was subsequently stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and then 10 ml of saturated potassium carbonate solution was added to the residue. The resulting solution was extracted with 20 ml of ethyl acetate, washed with 10 ml of IN aqueous hydrochloric acid solution, washed with aqueous sodium chloride solution and water, dried in sodium sulfate and subsequently dried. concentrated to yield 246 mg (0.79 mmol, yield: 79%) of the title compound. XH NMR (CDC13) d 2.46 (s, 2H), 2.80-3.40 (m, 8H), 3.40 (s, ÍH), 6.80 (s, ÍH), 7.00 ( s, HH), 7.42 (m, 4H), 7.73 (d, HH), 7.81 (d, 1H), 8.17 (d, HH), 10.66 (s, HH) FAB 309 (M + H) Preparation 7: Synthesis of 3- (morpholin-4-yl) carbonyl-4- (naph alen-1-yl) -lH-pyrrole 234 mg (1 mmol) of the compound prepared in the Preparation was dissolved 6-3) in 2 ml of dimethylformamide and then 230 mg (1.2 mmol) of EDC and 162 mg (1.2 mmol) of HOBT. The resulting mixture was stirred at 0 ° C for 5 minutes. To the reaction solution was added 87 mg (1 mmol) of morpholino, which was subsequently stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and subsequently 10 ml of saturated potassium carbonate solution were added to the residue. The resulting solution was extracted with ethyl acetate, washed with 10 ml of IN aqueous hydrochloric acid solution, washed with aqueous sodium chloride solution and water and then dried in concentrated sodium sulfate to yield 243 mg. (0.8 mmol, yield: 80%) of the title compound. ñ NMR (CDC13) d 2.13-3.52 (br, 8H), 6.54 (s, ÍH), 7.31-7.51 (m, 3H), 7.53 (s, ÍH), 7.81. (m, 2H), 9.93 (s, 1H) FAB 307 (M + H) Preparation 8: Synthesis of 3- (4-methylpiperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH -pyrrole The title compound was obtained in 75% yield according to the same procedure followed in Preparation 6-4) except that the compound prepared in Preparation, 6-3) and 4-methylpiperazine were used. XH NMR (CDC13) d 1.15 (br, 2H), 1.87 (br, 2H), 1.92 (s, 3H), 2.96 (br, 2H), 3.41 (br, 2H) , 6.83 (s, ÍH), 7.09 (s, ÍH), 7.36-7.42 (m, 4H), 7.73 (d, 1H), 7.75 (d, ÍH), 8.10 (d, 1H), 10.52 (s, 1H) FAB (M + H): 320 Preparation 9: Synthesis of 3-. { N- [2- (N, N-dimethylamino) ethyl] -N-methyl} carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole The title compound was obtained in 82% yield according to the same procedure followed for Preparation 6-4) except that the compound prepared in the Preparation 6-3) and N, N, N '-trimethyl-ethylenediamine. XH NMR (CDC13) d 1.89 (br, 3H), 2.18 (br, 4H), 2.44 (br, 2H), 2.75 (s, 1H), 2.98 (br, ÍH) , 3.36 (br, 2H), 6.84 (s, ÍH), 7.07 (s, ÍH), .7.38-7.43 (m, 4H), 7.74 (d, ÍH) , 7.83 (d, ÍH), 8.13 (b, ÍH), 10.14 (br, 1H) FAB (M + H): 322 Preparation 10: Synthesis of 4- (naphthalen-1-yl) - 3- (thiomorpholin-4-yl) carbonyl-lH-pyrrole 234 mg (1 mmol) of the compound prepared in Preparation 6-3) were dissolved in 2 ml of dimethylformamide and subsequently 230 mg (1.2 mg) were added thereto (1.2 mmol). mmol) of EDC and 162 mg (1.2 mmol) of HOBT. The resulting mixture was stirred at 0 ° C for 3 minutes. To the reaction solution were added 87 mg (1 mmol) of thiomorpholino, which was subsequently stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and then 10 ml of saturated potassium carbonate solution was added to the residue. The resulting solution was extracted with ethyl acetate, washed with 10 ml of IN aqueous hydrochloric acid solution, washed with saturated sodium chloride solution and water and then dried with sodium sulfate and concentrated to produce 258 mg (0.8 mmol, yield: 80%) of the title compound. XH NMR (CDC13) d 1.35 (br, 2H), 2.14 (br, 2H), 3.21 (br, 2H), 3.41 (br, 2H), 6.91 (s, ÍH) , 7.21 (s, ÍH), 7.31-7.51 (m, 4H), 7.80 (d, ÍH), 7.87 (d, ÍH), 8.11 (d, ÍH), 10.69 (s, ÍH) FAB 323 (M + H) Preparation 11: Synthesis of 3- (1, l-dioxothiomorpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -IH-pyrrole 323 mg (1 mmol) of the compound prepared in Preparation 10 were dissolved in 3 ml of dichloromethane, added 430 mg (1.5-mmol) of 60% 3-chloroperbenzoic acid (MCPBA) and the resulting mixture was stirred at room temperature for 1 hour. 3 ml of sodium thiosulfate was added to the % to the mixture. in order to extract the excess 3-chloroperbenzoic acid and the resulting mixture was stirred at room temperature for 30 minutes. After the addition of the saturated potassium carbonate solution, the mixture was extracted with dichloromethane, washed with sodium chloride solution and water, dried with sodium sulfate and concentrated to yield 264 mg (0, 75 mmol, yield: 73%) of the title compound. XH NMR (CDC13) d 1.50-2.30 (br, 4H), 3.65 (br, 4H), 6.92 (s, ÍH), 7.20 (s, ÍH), 7.32- 7.34 (m, 4H), 7.81 (d, ÍH), 7.88 (d, ÍH), 8.12 (d, ÍH), 10.69 (s, ÍH) FAB 355 (M + H ) Preparation 12: Synthesis of 3- [N- (2-methyl-yl-yl) -N-methyl] -carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole 324 mg (1 mmol) of the prepared compound were dissolved in Preparation 6-3) in 2 ml of dimethylformamide, 230 mg (1.2 mmol) of EDC, 101 mg (1 mmol) of triethylamine and 162 mg (1.2 mmol) of HOBT were added. The resulting mixture was stirred at 0 ° C for 5 hours. They were added to the • Reaction solution 140 mg (1 mmol) of N- (2-methylthioethyl) -N-methylamine chloride which was subsequently stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and then a saturated potassium carbonate solution was added to the residue. The The resulting solution was treated with 20 ml of ethyl acetate, washed with 10 ml of IN aqueous hydrochloric acid solution, and • washed with saturated sodium chloride solution and water, dried with sodium sulfate and concentrated to yield 243 mg (0.75 mmol, yield: 75%) of the title compound. XH NMR (CDC13) d 1.98 (s, 3H), 2.13 (br, 2H), 2.46 (br, 2H), 2.65 (br, ÍH), 2.95 (br, ÍH) ), 3.29 (br, ÍH), 6.81, '(s, ÍH), 7.02 (s, ÍH), 7.43 (m, 4H), 7.72 (d, 1H), 7 , 82 (d, ÍH), 8,18 (d, ÍH), 10.65 (s, ÍH) FAB 325 (M + H) 20 Preparation 13: Synthesis of 3-hydroxycarbonyl-5-methyl-4- (naf alen-1-yl) -lH-pyrrole 13-1) 3-ethoxycarbonyl-5-methyl-4- (naphthalen-1-yl) -IH-pyrrole. 4.3 g (18.9 mmol) of 3 were added. - (naphthalen-1-yl) - acrylic acid ethyl ester to be prepared in Preparation 6-1) and 3.95 g (18.9 mmol) of a-met Utos ilmet ilisocyanide presented in AM van Leusen and his collaborators, Tetrahedron Letter, 1975, 40, 3487 in 100 ml of tetrahydrofuran. 2.55 g (22.7 mmol) of potassium t-butoxide dissolved in 100 ml of tetrahydrofuran was slowly added thereto, which was then refluxed for 30 minutes. 100 ml of water was introduced into the reaction solution to stop the reaction and the solvent was removed under reduced pressure. The residue was extracted with diethyl ether, washed with saturated sodium chloride solution and dried in magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to silica gel column chromatography using a solvent mixture of ethyl acetate / n-hexane (1/3, v / v) as an eluent to yield 3.50 g ( 12.5 mmol, yield: 66%) of the title compound. FAB 280 (M + H) 13-2) 3-Hydroxycarbonyl-5-methyl-4- (naphthalen-1-yl) -1H-pyrrole 2.80g (10 mmol) of the compound to be prepared in Preparation 13 was dissolved. -1) in 50 ml of ethanol, 2.24 g (40 mmol) of potassium hydroxide were introduced, and the mixture was refluxed for 7 hours. The reaction solution was cooled to room temperature, adjusted to pH 4-5, extracted with ethyl acetate and dried in sodium sulfate. The solvent was removed under reduced pressure to obtain 2.02 g (8.1 mmol, yield: 81%) of the title compound. FAB 252 (M + H) Preparation 14: Synthesis of 5-methyl-3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole 248 mg (1 mmol) of the compound prepared in Preparation 13-2) were dissolved in ml of dimethylformamide, and then 230 mg (1.2 mmol) of EDC and 162 mg (1.2 mmol) of HOBT were introduced thereto. The resulting mixture was stirred at 0 ° C for 5 minutes. 87 mg (1 mmol) of morpholino were added to the reaction solution, which was then stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and then 10 ml of saturated potassium carbonate solution was added to the residue, The resulting solution was extracted with ethyl acetate, washed with 10 ml of IN aqueous hydrochloric acid solution, washed with saturated sodium chloride solution and water, dried in sodium sulfate and concentrated to yield 224 mg (0.7 mmol, yield: 70%) of the title compound.1i NMR (CDC13) d 2.12 (s, 3H), 2.80-3.40 (br, 8H), 7.01 (s, ÍH), 7.30-7.50 (m, 4H), 7.75-7.95 (m , 3H), 10.60 (br, ÍH) FAB 321 (M + H) Example 1: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- (3, 4 -methylenedioxybenzyl) -lH-imidazol-5-ylmethyl] -4- (naphthalen-1-yl) -lH-pyrrole (1) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. ezcla 50 mg (2, 2 mmol) of the compound to be prepared in Preparation 1 and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 78 mg (yield: 75%) of the title compound. XH NMR (CDC13) d 2.40 (m, 2H), 2.72 (m, ÍH), 2.91. (s, 3H), 3.09 (m, 2H), 3.32 (br, 1H), 4.09 (br, ÍH), 4.89 (s, 2H), 4.95 (s, 2H) , 5.89 (s, 2H), 6.45 (s, ÍH), 6.62 (d, 1H), 6.63 (s, ÍH), 6.70 (d, ÍH), 7.0 ( s, ÍH), 7.16 (s, 1H), 7.31 (t, HH), 7.41 (m, 3H), 7.66 (s, HH), 7.73 (d, 1H), 7.81 (d, ÍH), 8.03 (d, ÍH) FAB (M + H) 523, C3? H30N4O2 Example 2: Synthesis of 1- [1- (3, 4-methylenedioxybenzyl) -lH-imidazole- 5-ylmethyl] -3- (morpholin-4-yl) carbonyl-4 (naphthalen-1-yl) -lH-pyrrole (2) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 7 was dissolved. in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 1 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 70 mg (yield: 67%) of the title compound. XH NMR (CDC13) d 2.36 (br, 2H), 3.06 (br, 4H), 3.33 (br, 2H), 5.23 (s, 2H), 5.33 (s, 2H) , 5.96 (s, 2H), 6.65 (s, ÍH), 6.70-6.85 (m, 3H), 7.18-7.50 (m, 7H), 7.79 (d , HH), 7.81 (d, HH), 7.94 (d, HH) FAB (M + H) 521, C3 H H28N404 Example 3: Synthesis of 1- [1- (3,4-methylenedioxybenzyl) - 1H-imidazol-5-ylmethyl] -3- (4-methylpiperazin-1-yl) sarbonyl-4- (naphthalen-1-yl) -lH-pyrrole (3) 64 mg (0.2 mmol) of the compound was dissolved to be prepared in Preparation 8 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) was added at 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 1 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5). , v / v) to obtain 78 mg (yield: 75%) of the title compound. 1l NMR (CDC13) d 2.18 (s, 3H), 2.30-2.60 (br, 4H), 3.10-3.30 (br, 4H), 4.98 (s, 2H), 5.03 (s, 2H), 5.95 (s, 2H), 6.44 (s, 1H), 6 , 53 (d, ÍH), 6,7 (d, ÍH), 6,73 (d, ÍH), 7,14 (d, ÍH), 7.20-7.40 (m, 3H), 7.50 fm, 3H), 7.81 (d, ÍH), 7.83 (d, ÍH), 7.88 (d, 1H) FAB (M + H) 534, C32H3? N503 Example 4: Synthesis of 3-. { N- [2- (N, N-dimethylamino) ethyl] -N-methyl} carbamoyl-1- [1- (3, 4-methylenedioxybenzyl) -lH-imidazol-5-ylmethyl] -4- (naphthalen-1-yl) -lH-pyrrole (4) 64 mg (0.2 mmol) was dissolved of the compound to be prepared in Preparation 9 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added to 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 1 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5). , v / v) to obtain 78 mg (yield: 71%) of the title compound. XH NMR (CDC13) d 1.87 (m, ÍH), 2.01 (m, 2H), 2.14 (br, 6H), 2.36 (br, 2H), 2.50-3.00 ( br, ÍH), 3.29 (br, 2H), 4.87 (s, 2H), 4.95 (s, 2H), 5.89 (s, 2H), 6.45 (s, ÍH), 6.50 (d, ÍH), 6.63 (d, 1H), 6.72 (d, ÍH), 7.00 (s, ÍH), 7.18 (s, ÍH), 7.31 (br , ÍH), 7.35-7.47 (m, 3H), 7.54 (s, ÍH), 7.73 (d, ÍH), 7, 81. (d, 1H), 8, 01 (br , ÍH) FAB (M + H) 536, C32H33N503 Example 5: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4-naphthalen-1-yl) -1- [1-naph alen -1-ylmethyl) -lH-imidazol-5-ylmethyl] -lH-pyrrole (5) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26 were added, 4 mg (0.66 mmol) of sodium hydride (60%) at 0 ° C and then the mixture was stirred for 5 minutes. 58 mg (2.2 mmol) of the compound to be prepared in Preparation 2 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 79 mg (yield: 75%) of the title compound. XH NMR (CDC13) d 2.37 (br, 2H), 2.72 (br, ÍH), 2.99 (br, 3H), 3.00 (br, 2H), 3.31 (br, ÍH) , 3.71 (br, ÍH), 5.06 (s, 2H), 5.48 (s, 2H), 6.62 (d, ÍH), 6.91 (d, ÍH), 7.03 ( d, 1H), 7.27 (d, 2H), 7.28-7.55 (m, 6H), 7.58 (s, ÍH), 7.69 (d, ÍH), 7.75 (d , HH), 7.81 (d, 2H), 7.87 (d, HH), 8.00 (d, HH) FAB (M + H) 529, C34H32N402 Example 6: Synthesis of 3- (morpholin-4) -yl) carbonyl-4- (naphthalen-1-yl) -1- [1-naph alen-1-ylmethyl) -lH-imidazol-5-ylme il] -lH-pyrrole (6) 62 mg ( , 2 mmol) of the compound to be prepared in Preparation 7 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added to 0 ° C and then the mixture was stirred for 5 minutes. 58 mg (2.2 mmol) of the compound to be prepared in Preparation 2 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5). , v / v) to obtain 76 mg (yield: 72%) of the title compound. ? E NMR (CDC13) d 2.38 (br, 2H), 3.06 (br, 4H), 3.30 (br, 2H), 4.99 (s, 2H), 5.42 (s, 2H) ), 6.58 (d, ÍH), 6.80 (d, 1H), 7.00 (s, 1H), 7.17 (d, ÍH), 7.25 (s, ÍH), 7.26 -7.54 (m, 6H), 7.69 (d, 1H), 771-7.81 (m, 3H), 7.85 (d, 1H), 7.91 (d, 1H) FAB (M + H) 527, C34H30N4O2 Example 7: Synthesis of 3- (4-methylpiperazine- 1-yl) carbonyl-4- (na talen-1-yl) -1- [1- (naph-alen-1-ylmethyl) -1H-imidazol-5-ylmethyl] -lH-pyrrole (7) 62 mg was dissolved (0.2 mmol) of the compound to be prepared in Preparation 8 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the Mix for 5 minutes. 58 mg (2.2 mmol) of the compound to be prepared in Preparation 2 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5). , v / v) to obtain 75 mg (yield: 69%) of the title compound. NMR (CDC13) d 1.07 (br, 2H), 1.77 (d, 2H), 1.85 (s, 3H), 2.84 (br, 2H), 3.27 (br, 2H) ), 4.99 (s, 2H), 5.42 (s, 2H), 6.58 (d, ÍH), 6.80 (d, ÍH), 7.01 (d, ÍH), 7.16 (d, HH), 7.25 (s, 1H), 7.31-7.60 (m, 6H), 7.68 (d, HH), 7.69-7.83 (m, 3H), 7.85 (d, ÍH), 7.94 (d, ÍH) FAB (M + H) 540, C35H33N50 Example 8: Synthesis of 3- [N- (2-methyoxyethyl) -N-methyl) carbamoyl-1- [1- ((R) -a-methylbenzyl) -lH-imidazole -5-ylmethyl] -4- (naphthalen-1-yl) -lH-pyrrole (8) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26 , 4 mg (0.66 mmol) of sodium hydride (60%) at 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 3 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that the mixture was extracted twice with 10 ml of ethyl acetate, dried in sulphate Anhydrous sodium was added, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5, v / v) to obtain 70 mg (yield: 71%) of the title compound. 10? R NMR (CDC13) d 1.78 (d, 3H), 2.28 (s, ÍH), 2.40 (br, 2H), 3.02 (br, 3H), 3.09- (br , 2H), 3.32 (br, 2H), 4.71 (d, • 2H), 4.92 (d, 2H), 5.12 (q, ÍH), 6.59 (d, ÍH), 7.00 (m, 3H), 7.18 (s, ÍH), 7 , 20-7.39 (m, 4H), 7.40-7.62 (m, 3H), 7.74 (m, 2H), 7.82 (d, IH), 8.04 (d, IH) ) 15 FAB (M + H) 493, C3? H32N402 Example 9: Synthesis of 1- [1- ((R)) -a-methylbenzyl) -1H-imidazol-5-ylmethyl] -3- (morpholine-4-) il) carbonyl-4- (na talen-1-yl) -lH-pyrrole (9) 62 mg (0.2 mmol) of the compound being dissolved were dissolved.

In Preparation 7, prepare 2 ml of dimethylformamide, add 26.4 mg (0.66 mmol) of sodium hydride (60%) at 0 ° C and then stir the mixture for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 3 were introduced into the mixture and the whole mixture was stirred room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 71 mg (yield: 72%) of the title compound. H NMR (CDC13) d 1.81 (d, 3H), 2.28 (br, 2H), 3.06 (br, 4H), 3.29 (br, 2H), 4.65 (d, ÍH) , 4.96 (d, ÍH), 5.14 (q, ÍH), 6.62 (d, ÍH), 7.01 (d, 2H), 7.04 (s, ÍH), 7.20 ( s, HH), 7.23-7.36 (m, 5H), 7.39-7.50 (m, 3H), 7.76 (s, HH), 7.78 (d, HH), 7 , 84 (d, ÍH), 8.00 (d, ÍH) FAB (M + H) 491, C3? H30N4O2 Example 10: Synthesis of 1- [1- ((R) -a-methylbenzyl) -1H-imidazole -5-ylmethyl] -3- (4-methylpiperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (10) 64 mg (0.2 mmol) of the compound to be prepared was dissolved in Preparation 8 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) was added at 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 3 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 73 mg (yield: 73%) of the title compound. XH NMR (CDC13) d 1.09 (br, 2H), 1.77 (d, 3H), 1.83 (s, 3H), 1.70-1.00 (br, 2H), 2.90 (br, 2H), 3.31 (br, 2H), 4.73 (d, ÍH), 4.92 (d, ÍH), 5,14 (q, ÍH), 6,60 (d, ÍH), 7,01 (m, • 5 3 H), 7,17 (s, 'ÍH), 7,20-7,35 (m, 4H), 7,45 (m, 3H), 7,73 (m, 2H), 7.80 (d, 1H), 8.00 (d, ÍH) FAB (M + H) 504, C32H33N50 Example 11: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl -1- [1- ((S) -a-methylbenzyl) -lH-imidazol-5-yl-methyl] -10- 4- (naphthalene-1-yl) -lH-pyrrole (11) 62 mg was dissolved ( 0.2 mmol) of the compound that • Prepare in Preparation 6 in 2 ml of dimethylformamide, add 26.4 mg (0.66 mmol) of sodium hydride (60%) at 0 ° C and then stir the mixture for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 4 were added to the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted two times with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and chromatographed on silica gel column (eluent: dichloromethane / methanol = 95 / 5, v / v) to obtain 75 mg (yield: 75%) of the compound of the title. 1H NMR (CDC13) d 1.78 (d, 3H), 2.28 (s, ÍH), 2.40 (br, 2H), 3.02 (br, 3H), 3.09 (br, 2H) , 3.32 (br, 2H), 4.72 (d, 2H), 4.93 (d, 2H), 3.12 '(q, ÍH), 6.59 (d, ÍH), 7.00 (m, 3H), 7.18 (s, ÍH), 7.20-7.39 (m, 4H), 7.40-7.62 (m, 3H), 7.74 (m, 2H), 7.82 (d, ÍH), 8.04 (d, ÍH) FAB (M + H) 493, C3? H32N402 Example 12: Synthesis of 1- [1- ((S) -a-methylbenzyl) -1H- imidazol-5-ylmethyl) -3- (morpholin-4-yl) carbonyl-4- (naph alen-1-yl) -lH-pyrrole (12) 62 mg (0.2 mmol) of the compound to be prepared was dissolved in Preparation 7 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 4 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 73 mg (yield: 73%) of the title compound. XH NMR (CDC13) d 1.81 (d, 3H), 2.28 (br, 2H), 3.06 (br, 4H), 3.29 (br, 2H), 4.64 (d, ÍH), 4.93 (d, ÍH), 3.14 (q, 1H), 6.62 (d, ÍH), 7.01 (d, 2H), 7.04 (s, HH), 7.20 (s, HH), 7.23-7.36 (m, 5H), 7 , 39-7.50 (m, 3H), 7.76 (s, 1H), 7.78 (d, ÍH), 7.84 (d, ÍH), 8.00 (d, ÍH) FAB (M + H) 491, C3? H30N4O2 Example 13: Synthesis of 1- [1- ((S) -a-methylbenzyl) -IH- imidazol-5-ylmethyl) -3- (4-methylpiperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (13) 64 mg (0.2 mmol) of the compound to be prepared in Preparation 8 in 2 ml of dimethylformamide, added 26.4 mg (0.66 mmol) of sodium hydride (60%) to 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 4 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of ^ water to the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: Dichloromethane / methanol = 90/10, v / v) to obtain 75 mg (yield: 75%) of the title compound. 1ti NMR (CDC13) d 1.09 (br, 2H), 1.77 (d, 3H), 1.83 (s, 3H), 1.70-1.90 (br, 2H), 2.90 ( br, 2H), 3.31 (br, 2H), 4.74 (d, 20 ÍH), 4.93 (d, 1H), 5.14 (q, ÍH), 6.60 (d, ÍH) , 7.01 (m, 3H), 7.17 (s, ÍH), 7.20-7.35 (m, 4H), 7.43 (m, 3H), 7.73 (n, 2H), 7.80 (d, 1H), 8.00 (d, 1H) FAB (M + H) 504, C32H30N5O Example 14: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] -carbamoyl-4 - (naphthalen-1-yl) -1- [1- (phenethyl) -lH-imidazol-5-ylmethyl] -lH-pyrrole (14) 62 mg (0.2 mmol) of the compound to be prepared in the Preparation 6 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2 mg) were introduced into the mixture., 2 mmol) of the compound to be prepared in Preparation 5 and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromet no / methanol = 95 / 5, v / v) to obtain 77 mg (yield: 78%) of the title compound. 1 NMR (CDC13) d 2.38 (br, 2H), 2.70 (m, 1H), 2.80 (t, 2H), 2.90 (m, 3H), 3.00 (br, 2H) , 3.31 (br, 1H), 3.41 (br, ÍH), 4.03 (t, 2H). , 4.77 (s, 2H), 6.66 (d, ÍH), 6.97 (d, ÍH), 7.06 (d, HH), 7.22 (m, 3H), 7.30-7.60 (m, 5H), 7.75 (d, HH), 7.80 (d, ÍH), 8.04 (d, ÍH) FAB (M + H) 493, C3? H32N402 Example 15: Synthesis of 3- (morpholin-4-yl) carbonyl-4- (naph alen- 1-yl) -1- [phenethyl) -lH-imidazol-5-ylmethyl] -lH-pyrrole (15) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 7 were dissolved in 2 ml of dimethylformamide , 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 5 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 79 mg (yield: 80%) of the title compound. XH NMR (CDC13) d 2.28 (br, 2H), 2.81 (t, 2H), 2.83 (br, 4H), 3.21 (br, 2H), 4.07 (t, 2H) , 4.78 (s, 2H), 6.68- (d, ÍH), 6.99 (d, ÍH), 7.10 (d, 2H), 7.10 (d, 2H), 7.23 (m, 3H), 7.30 (d, ÍH), 7.50 (m, 3H), 7.67 (s, ÍH), 7.77 (d, ÍH), 7.82 (d, 1H) , 8.00 (d, ÍH) FAB (M + H) 491, C3? H30N4O? Example 16: Synthesis of 3- (4-methyl-piperazin-1-yl) carbonyl-4- (naph-alen-1-yl) -1- [1- (phenethyl) -lH-imidazol-5-yl-methyl) -lH -pyrrole (16) 62 mg (0.2 mmol) of the compound which was prepared in Preparation 8 was dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added. at 0 ° C and then the mixture was stirred for 5 minutes. 50 mg (2.2 mmol) of the compound to be prepared in Preparation 5 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml was introduced. of water to the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 90/10). , v / v) to obtain 75 mg (yield: 75%) of the compound of the title. XH NMR (CDC13) d 1.06 (br, 2H), 1.90-2.00 (br, 2H), 2.05 (s, 3H), 2.80 (t, 2H), 3.37 ( br, 4H), 4.04 (t, 2H), 4.77 (s, 2H), 6.69 (d, ÍH), 6.99 (m, 2H), 7.09 (d, 2H), 7.20-7.36 (m, 8H), 7.78 (d, HH), 7.83 (d, HH), 8.00 (d, HH) FAB (M + H) 304, C32H33N50 Preparation 15 : Synthesis of 1- (2-methoxy) phenethyl-5-chloromethyl-lH-imidazole 15-1) 1- (2-Methoxy) phenethyl-5-hydroxymethyl-1H-imidazole hydrochloride The title compound was obtained in a yield of the 65% according to the same procedure followed for the Preparation 1-1) except that dihydroxyacetone dimer and 2-methoxyphenethylamine were used as starting materials. XH NMR (CDC13) d 3.03 (t, 2H), 3.75 (s, 3H), 4.16 (t, 2H), 4.47 (s, 2H), 4.75 (s, 1H) , 6.74 (s, 1H), 6.73-7.00 (m, 3H), 7.13-7.30 (m, ÍH) FAB 233 (M + H), C? 3H6N202 (M) 15 -2) 1- (2-Methoxy) phenethyl-5-chloromethyl-1H-imidazole hydrochloride The title compound was obtained in a yield of 89% according to the same procedure followed for the Preparation 1-2) using the compound prepared in the Preparation 1-5). The compound obtained in this manner was used directly in the next reaction without purification. Preparation 16: Synthesis of 1- (4-methoxy) phenethyl-5-chloromethyl-1H-imidazole hydrochloride 1-6-1) 1- (4-Methoxy) phenethyl-5-hydroxymethyl-1H-imidazole The title compound was obtained with a performance of 60% according to the same procedure followed for the Preparation 1-1) except that dihydroxyacetone dimer and 4-methoxyphenethylamine were used as starting materials. XH NMR (CDC13) d 2.91 (t, 2H), 3.68 (s, 3H), 4.09 (t, 2H), 4.36 (s, 2H), 6.70 (d, 2H) , 6.77 (s, ÍH), 6.87 (d, 2H), 7.13 (s, ÍH) FAB 233 (M + H) CX3H? 6N202 (M) 16-2) Chlorhydrate of 1 - . 1- (4-Methoxy) phenethyl-5-chloromethyl-1H-imidazole The title compound was obtained in 89% yield according to the same procedure followed for Preparation 1-2) using the compound prepared in Preparation 16 -1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 17: Synthesis of 1- (2-fluo) phenethyl-5-chloromethyl-1H-imidazole 1-1 1-1) hydrochloride 1 - (2-f luo) phenethyl-5-hydroxymethyl-1H-imidazole The title compound was obtained in 68% yield according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone dimer and 2-fluphenethylamine were used as starting materials. XH NMR (CDC13) d 3.12 (t, 2H), 3.50 (br, ÍH), 4.23 (t, 2H), 4.52 (s, 2H), 6.82 (s, ÍH) , 7.02 (m, 3H), 7.20 (m, 2H) FAB 221 (M + H), C? 2Hi3N2OF (M) 11-2) 1- (2-Fluo) phenethyl-5-chloromethyl hydrochloride -IH-i idazole The title compound was obtained in 89% yield according to the same procedure followed for Preparation 1-2) using the compound prepared in Preparation 17-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 18: Synthesis of l- (2-chloro) phene-il-5-chloromethyl-1H-imidazole 18-1) 1- (2-Chloro) phenethyl-3-hydroxymethyl-1H-imidazole hydrochloride The title compound was obtained with a performance of 71% according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone dimer and 2-chlorophenethylamine were used as starting materials. XH NMR (CDC13) d 3.13 (t, 2H), 3.34 (br, ÍH), 4.18 (t, 2H), 4.42 (s, 2H), 6.79 (s, ÍH) , 6.94 (d, 1H), 7.03-7.20 (m, 3H), 7.29 (d, ÍH) FAB 237 (M + H), C? 2H? 3N2OCl (M) 18-2 ) 1- (2-Chloro) phenethyl-5-chloromethyl-1H-imidazole hydrochloride The title compound was obtained in 89% yield according to the same procedure followed for Preparation 1-2) using the compound prepared in Preparation 18-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 19: Synthesis of 1- (3-chloro) phene-5-chloromethyl-1H-imidazole 19-1) 1- (3-chloro) phenethyl-5-hydroxymethyl-1H-imidazole hydrochloride The title compound was obtained with a yield of 72% according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone dimer and 3-chlorophenethylamine were used as starting materials: 1H NMR (CDC13) d 2.95 (t, 2H) , 3.90 (br, ÍH), 4.10 (t, 2H), 4.37 (s, 2H), 6.74 (s, ÍH), 6.85 (m, ÍH), 6.98 ( s, 1H), 7.10 (m, 3H) FAB 237 (M + H), C? 2H? 3N2OCl (M) 19-2) Chlorohydrate of 1 - (3-Chloro) phenethyl-5-chloromethyl-IH Imidazole The title compound was obtained in 91% yield according to the same procedure followed for Preparation 1-2) using the compound prepared in Preparation 19-1. The product obtained in this way was used directly for in the next reaction without purification Preparation 20: Synthesis of 1- (3-enyl) propyl-5-chloro hydrochloride methyl-lH-imidazole 20-1) 1- (3-Phenyl) propyl-3-hydroxymethyl-1H-imidazole The title compound was obtained in a yield of 73% according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone and 3-phenylpropylamine dimer were used as starting materials. XH NMR (CDC13) d 2.11 (m, 2H), 2.61 (t, 2H), 3.98 (t, 2H), 4.25 (br, 1H), 4.53 (s, ÍH) , 6.76 (s, ÍH), 7.10-7.60 (m, 6H) FAB 217 (M + H), C13H16N20 (M) 20-2) Chlorhydrate to. of 1- (3-Phenyl) propyl-5-chloromethyl-1H-imidazole The title compound was obtained in a yield of 91% according to the same procedure followed for the Preparation 1-2) using the compound prepared in Preparation 20-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 21: Synthesis of 1- (nalen-2-yl) ethyl-5-chloromethyl-1H-imidazole 21 -1) 1 - (Naphthalen-2-yl) methyl-3-hydroxymethyl-1H-imidazole hydrochloride Obtained the title compound with a yield of 58% according to the same procedure used for Preparation 1-1) except that the dimer of dihydroxyacetone and (naphthalen-2-yl) methylamine were used as starting materials. 1ñ NMR (CDC13) d 4, 36 (s, 2H), 3.28 (s, 2H), 6.89 (s, ÍH), 7.17 (d, ÍH), 7.35 (m, 2H), 7.41 (s, ÍH), 7.30 (s, ÍH), 7.65 (m, ÍH), 7, 69 (m, 2H).

FAB 239 (M + H), C? 5H? 4 (M) 21 -2) Chloride of l - (Naphthalen-2-yl) methyl-5-chloro-methyl-1H-imide zol The compound of title with a yield of 87% according to the same procedure followed in Preparation 1-2) using the compound prepared in Preparation 21-1). The product obtained in this way was then used directly in the next reaction without purification. Preparation 22: Synthesis of 1- [2- (na talen-1-yl) ethyl] -5-chloromethyl-lH-imidazole 22-1) 1 - [2- (Naphthalen-1-yl) ethyl] -5 hydrochloride -hydroxymethyl-1H-imidazole The title compound was obtained with a yield of 58% according to the same procedure followed for the Preparation - 1-1) except that the dihydroxyacetone dimer and (naphthalen-1-yl) ethylamine were used as starting materials. XH NMR (CDC13) d 3.44 (t, 2H), 4.23 (t, 2H), 4.38 (s, 2H), 6.79 (s, ÍH), 7.07 (d, ÍH) , '7.17 (s, 1H), 7.24 (t, ÍH), 7.32-7.48 (m, 2H), 7.62 (d, ÍH), 7.74 (d, ÍH) , 7.92 (d, ÍH) FAB 253 (M + H), C? SH? 6N20 (M) 22-2) Chlorohydrate of l - [2- (naphthalen-l -yl) ethyl] -5-chloro -met il -1 H-imide ol The title compound was obtained in 87% yield according to the same procedure as that followed for Preparation 1-2) using the compound prepared in Preparation 22-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 23: Synthesis of 1- (4-bromo) hydrochloride • ene il-5-chlorome il-lH-imidazole 5 23-1) 1- (4-Bromo) phenethyl-5-hydroxymethyl-1H-imidazole The title compound was obtained in a yield of 72% according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone dimer and 4-bromophenethylamine were used as materials initials. XH NMR (CDC13) d 2.94 (t, 2H), 3.76 (br, ÍH), 4.11 (t, 2H), 4.37 (s, 2H), 6.74 (s, ÍH) , 6.85 (d, 2H), 6.84 (d, 2H), 7.12 (s, ÍH), 7.29 (d, 2H) FAB 281 (M + H), C? 2H? 3N20Br ( M) 15 23-2) 1- (4-Bromo) phenethyl-5-chloromethyl-1H-imidazole hydrochloride The title compound was obtained in 91% yield according to the same procedure as that followed for Preparation 1-2) using the compound prepared in the • 20 Preparation 23-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 24: Synthesis of 1- (4-fluo) phenethyl-5-chloromethyl-1H-imidazole hydrochloride 24-1-1- (4-Fluo) phenethyl-5-hydroxymethyl-1H-imidazole The title compound was obtained with a yield of 72% according to the same procedure followed for the Preparation 1-1) except that dihydroxyacetone dimer and 4-fluphenethylamine were used as starting materials. XH NMR (CDC13) d 2.99 (t, 2H), 3.76 (br, ÍH), 4.15 (t, 2H), 4.45 (s, 2H), 6.80-7.20 ( m, 5H), 7.26 (s, ÍH) FAB 221 ('M + H), C? 2H? 3N2OF (M) 24-2) 1- (4-Fluo) phenethyl-5-chloromethyl-lH hydrochloride imidazole The title compound was obtained with a yield of 91% according to the same procedure followed for Preparation 1-2) using the compound prepared in the Preparation 24-1). The product obtained in this manner was directly used in the next reaction without purification. Preparation 25: Synthesis of 1- (4-methyl) phene-5-chloromethyl-1H-imidazole 25-1) 1- (4-methyl) phenethyl-5-hydroxymethyl-1H-imidazole hydrochloride The title compound was obtained with a performance of 72% according to the same procedure followed for the Preparation 1-1) except that dihydroxyacetone dimer and 4-methylphenethylamine were used as starting materials. 1H NMR (CDC13) d 3.02 (t, 2H), 2.99 (t, 2H), 3.76 (br, ÍH), 4.19 (t, 2H), 4.47 (s, 2H) , 6.83 (s, ÍH), 6.94 (d, 2H), 7.06 (d, 2H), 7.28 (s, ÍH) FAB 217 (M + H), C? 3H? 6N20 ( M) 25-2) 1 (4-Methyl) phenethyl-5-chloromethyl-1H-imidazole hydrochloride The title compound was obtained in 91% yield according to the same procedure followed for Preparation 1-2) using the compound prepared in Preparation 25-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 26: Synthesis of 1- (4-chloro) phenethyl-3-chloromethyl-1H-imidazole 26-1) 1- (4-Chloro) phenethyl-3-hydroxymethyl-1H-imidazole hydrochloride The title compound was obtained with a yield of 73% according to the same procedure followed for the Preparation 1-1) except that dihydroxyacetone dimer and 4-chlorophenethylamine were used as starting materials. XH NMR (CDC13) d 3.04 (t, 2H), 4.18 (t, 2H), 4.48 (s, 2H), 6.79 (s, ÍH), 6.96 (d, 2H) 7.20-7.40 (m, 3H) FAB 237 (M + H), C? 2H? 3N2OCl (M) 26-2) 1- (4-Chloro) phenethyl-5-chloromethyl-1H- hydrochloride Imidazole The title compound was obtained in 91% yield according to the same procedure followed for Preparation 1-2) using the compound prepared in Preparation 26-1). The product obtained in this manner was used directly in the next reaction without purification. Preparation 27: Synthesis of l- [2- (naph alen-2-yl) ethyl] -5-chloromethyl-lH-imidazole 27-1) l - [2-Naphthalen-2-yl) ethyl] -5- hydrochloride hydroxymethyl-1H-imidazole The title compound was obtained in 58% yield according to the same procedure followed for Preparation 1-1) except that dihydroxyacetone dimer and 2- (naphthalen-2-yl) ethylamine were used as materials initials. 1 NM NMR (CDC13) δ 3.22 (t, 2H), 4.28 (t, 2H), 4.48 (s, 2H), 6.84 (s, HH), 7.19 (d, HH) , 7.24 (d, 2H), 7.44 (m, 2H), 7.52 (s, ÍH), 7.76 (m, 3H) FAB 233 (M + H), C16H? 6N20 (M) 10 27-2) 1 - [2-Naphthalen-2-yl) ethyl] -5-chloromethyl-1H-imidazole hydrochloride # The title compound was obtained in 88% yield according to the same procedure followed for Preparation 1-2) using the compound prepared in the Preparation 27-1). The product obtained in this manner was used directly in the next reaction without purification. Example 17: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- (2-methoxy) phenethyl-1H-imidazol-5-yl] methyl-4- (naphthalene) 1-yl) -lH-pyrrole (17) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of hydride were added of sodium (60%) at 0 ° C and then the mixture was stirred for 5 minutes. 63 mg (2.2 mmol) of the compound that was added to the mixture were introduced into the mixture.

V was prepared in Preparation 15 and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 78 mg (yield: 75%) of the title compound. XH NMR (CDC13) d 2.39 (s, 2H), 2.71 (br, ÍH), 2.90 (t, 2H), 2.95-3.15 (m, 5H), 3.31 ( br, ÍH), 3.32 (br, ÍH), 3.76 (s, 3H), 4.06 (t, 2H), 4.83 (s, 2H), 6.68 (s, ÍH), 6.75-6.95 (m, 3H), 7.23 (s, ÍH), 7.25 (s, ÍH), 7.21 (t, 1H), 7.30-7.48 • (m, 4H), 7.30 (s, ÍH), 7.73 (d, ÍH), 7.81 (d, ÍH), 8.06 (d, ÍH) FAB 523 (M + H), C32H34N403 (M) 15 Example 18: Synthesis of 1- [1- (2-methoxy) phenethyl-1H-imidazol-5-yl] ethyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalene- 1-yl) -lH-pyrrole (18) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 8 were dissolved in 2 ml of dimethylformamide, added 26.4 mg (0.66 mmol) of sodium hydride (60%) to 0 ° C then the mixture was stirred for 5 minutes. 63 mg (2.2 mmol) of the compound to be prepared in Preparation 15 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 75 mg (yield: 70%) of the title compound. XH NMR (CDC13) d 1.09 (br, 2H), 1.70-2.10 (br + s, 5H), 2.83 (t, 2H), 2.99 (br, 2H), 3, 40 (br, 2H), 3.76 (s, 3H), 4.04 (t, 2H), 4.83 (s), 2H), 6.69 (d, 1H), 6.80-6.92 (m, 3H), 7.04 (s, ÍH), 7.08 (s, ÍH), 7.23 (t, ÍH), 7.30 (d, ÍH), 7.33-7.50 (m, 4H), 7.77 (d, 1H), 7.80 (d, 1H), 8.02 (d, ÍH) ) FAB 334 (M + H) C33H34N502 (M) Example 19: Synthesis of 3- [N- (1-methoxyethyl) -N-methyl] carbamoyl-1- [1- (4-methoxy) phenethyl-1H-imidazole- 5-yl] methyl-4- (naphthalen-1-yl) -lH-pyrrole (19) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26 , 4 mg (0.66 mmol) of sodium hydride (60%) at 0 ° C and then the mixture was stirred for 5 minutes. 63 mg (2.2 mmol) of the compound to be prepared in Preparation 16 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 83 mg (yield: 80%) of the title compound.

XH NMR (CDC13) d 2.38 (br, 2H), 2.72 (t, 2H), 2.83-3.13 (m, 7H), 3.31 (br, ÍH), 3.72 (s, 3H), 3.97 (t, 2H), 4.78 (s, 2H), 6.69 (d, ÍH), 6.77 (d, 2H), 6.83 (d, 2H), 7.03 (s, ÍH), 7.06 (s, ÍH), 7.24-7.50 (m, 5H), 7.73 (d, ÍH), 7.82 (d, 1H), 8.03 (d, ÍH) FAB 523 (M + H), C3? H34N403 (M) Example 20: Synthesis of 1- [1- (4-methoxy) phenethyl-1H-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (n-aftalen-1-yl) -lH-pyrrole (20) 62 mg (0.2 mmol) of the compound that was prepared in Preparation 8 was dissolved in 2 ml of dimethylformamide, 26.4 mg was added (0.66 mmol) of sodium hydride (60%) at 0 ° C and then the mixture was stirred for 5 minutes. 63 mg (2.2 mmol) of the compound to be prepared in Preparation 16 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 83 mg (yield: 78%) of the title compound. 1ti NMR (CDC13) d 1.03 (br, 2H), 1.70-2.10 (br + s, 4H), 2.24 (br, ÍH), 2.72 (t, 2H), 2, 89 (br, 2H), 3.30 (br, ÍH), 3.73 (s, 3H), 3.98 (t, 2H), 4.79 (s, 2H), 6.69 (d, ÍH) ), 6.76 (d, 2H), 6.86 (d, 2H), 7.08 (m, 2H), 7.30-7.50 (m, 5H), 7.74 (d, 1H) , 7.80 (d, 1H), 8.00 (d, 1H) FAB 334 (M + H), C33H35N502 (M) Example 21: Synthesis of 1- [1- (2-fluo) phenethyl-1H-imidazole -5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naph alen-1-yl) -IH-pyrrole (21) 62 mg (0.2 mmol) were dissolved ) of the compound to be prepared in Preparation 6 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 61 mg (2.2 mmol) of the compound to be prepared in Preparation 17 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 78 mg (yield: 77%) of the title compound. R NMR (CDC13) d 2.38 (br, 2H), 2.70 (br, ÍH), 2.81 (t, 2H), 2.90-3.38 (m, 7H), 4.03 (t, 2H), 4.91, (s, 2H), 6.71 (d, 2H), 6.92 (m, ÍH), 6.95-7.12 (m, 4H), 7.19 (m, 1H), 7.30-7.65 (m, 4H), 7.73 (d, ÍH), 7.80 (d, ÍH), 8.05 (d, ÍH) FAB 534 (M + H), C3? H31N402F (M) Example 22: Synthesis of 1- [1- (2-fluo) phenethyl-lH-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4 - (naphthalen-1-yl) -lH-pyrrole (22) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 8 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mg) were added. mmol) of sodium hydride (60%) at 0 ° C and then the mixture was stirred for 5 minutes. 61 mg (2.2 mmol) of the compound to be prepared in Preparation 17 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 78 mg (yield: 75%) of the title compound. XH NMR (CDC13) d 1.04 (br, 2H), 1.70-2.10 (br + s, 3H), 2.81 (m, 2H), 3.90 (br, 2H), 3.32 (br, 2H), 4.05 (t, 2H), 4.93 (s, 2H), 6.72 (d, ÍH), 6.90 (t, ÍH), 6.95-7.05 (m, 2H), 7.10 (d, 2H), 7.20 (m, ÍH) ), 7.23-7.50 (m, 4H), 7.75 (d, IH), 7.82 (d, 2H), 8.00 (d, ÍH) FAB 522 (M + H). C32H32N5OF (M) Example 23: Synthesis of 1- [1- (2-chloro) phenethyl-lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -IH-pyrrole (23) 62 mg (0, 2 mmol) of the compound to be prepared in Preparation 6 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred 5 minutes. 64 mg (2.2 mmol) of the compound to be prepared in Preparation 18 were introduced to the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 75 mg (yield: 71%) of the title compound. XH NMR (CDC13) d 2.39 (br, 2H), 2.71 (br, 1H), 2.90-3.38 (m, 9H), 4.06 (t, 2H), 4.87 ( s, 2H), 6.71 (s, ÍH), 6.87 (m, ÍH), 7.00-7.20 (m, 4H), 7.30-7.60 (m, 6H), 7 , 73 (d, ÍH), 7.89 (d, ÍH), 8, 06 (d, ÍH) FAB 527 (M + H), C3? H3? N402Cl (M) Example 24: Synthesis of 1- [1 - (1-chloro) phenethyl-1H-imidazol-5-yl] ethyl-3- [4-methyl-piperazin-1-yl] -carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (24) were dissolved mg (0.2 mmol) of the compound to be prepared in Preparation 8 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then stirred Mix for 5 minutes. 64 mg (2.2 mmol) of the compound to be prepared in Preparation 18 were introduced to the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 84 mg (yield: 78%) of the title compound. ? ti NMR (CDC13) d 1.04 (br, ÍH), 1.70-2.10 (br + s, 3H), 2.35 (br, ÍH), 2.92 (t + br, 4H) , 3.32 (br, 2H), 4.08 (t, 2H), 4.88 (s, 2H), 6.71 (s, ÍH), 6.87 (m, ÍH), 7.09 ( m, 3H), 7.18 (m, ÍH), 7.30-7.55 (m, 6H), 7.75 (d, ÍH), 7.81 (d, ÍH), 8.01 (d ÍH) FAB 538 (M + H), C 32 H 32 N 50 Cl (M) Example 25: Synthesis of 1- [1- (3-chloro) phenethyl-1 H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl ) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (25) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 64 mg (2.2 mmol) of the compound to be prepared in Preparation 19 were introduced to the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methane = 95/5 , v / v) to obtain 80 mg (yield: 76%) of the title compound. 1ti NMR (CDC13) d 2.37 (br, 2H), 2.71 (m, 3H), 2.90-3.20 (m, 6H), 3.30 '(br, ÍH), 3.99 (t, 2H), 4.86 (s, 2H), 6.69 (d, 1H), 6.81 (d, ÍH), 7.00 (s, ÍH), 7.05-7.20 ( m, 5H), 7.30-7.50 (m, 4H), 7.74 (d, ÍH), 7.81 (d, ÍH), 8.04 (d, ÍH) FAB 527 (M + H ), C3? H3? N402Cl (M) Example 26: Synthesis of 1- [1- (3-chloro) phenethyl-lH-imidazol-5-yl] methyl-3- (4-methylpiperazin-1-yl) carbonyl- 4- (naphthalen-1-yl) -lH-pyrrole (26) 62 mg (0.2 mmol) of the compound which was prepared in Preparation 6 was dissolved in 2 ml of dimethylformamide, 26.4 mg (0, 66 mmol) of sodium hydride (60%) at 0 ° C and then the mixture was stirred for 5 minutes 64 mg (2.2 mmol) of the compound which was prepared in Preparation 19 was added to the mixture and stirred The whole mixture was stirred at room temperature for 2 hours, the solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue, after which the mixture was extracted twice with 10 ml of ethyl acetate. or, it was dried in anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methane = 95/5, v / v) to obtain 80 mg (yield: 76%). of the title compound. XH NMR (CDC13) d 1.05 (br, 2H), 1.70-2.10 (br + s, 5H), 2.69 (t, 2H), 2.90 (br, 2H), 3, 32 (br, 2H), 3.98 (t, 2H), 4.87 (s, 2H), 6.70 (d, ÍH), 6.79 (d, ÍH), 6.98 (s, ÍH) ), 7.05-7.21 (m, 3H), 7.30-7.50 (m, 6H), 7.74 (d, IH), 7.82 (d, IH), 7.99 ( d, ÍH) FAB 538 (M + H), C 32 H 32 N 50 Cl (M) Example 27: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naph alen-1-yl) -1 - [1- (3-f nyl) propyl-lH-imidazol-5-yl] methyl-lH-pyrrole (27) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added to 0 ° C and then the mixture was stirred for 5 • minutes. 62 mg (2.2 mmol) of the compound to be prepared in Preparation 20 were introduced to the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluyerite: dichloromethane / methanol = 95/5 , v / v) to obtain 76 mg (yield: 75%) of the title compound. XH NMR (CDC13) d 1.91 (m, 2H), 2.24 (t, 2H), 2.56 (m, 5H), 2.90-3.07 (m, 4H), 3.18 (br, ÍH), 4.03 (t, 2H), 5.12 (s, 2H), 6.37 (s, ÍH), 6 , 90-7.20 (m, 8H), 7.21-7.52 (, 3H), 7.66 (d, HH), 7.72 (d, ÍH), 7.89 (d, HH), 8.06 (br, HH) FAB 507 (M + H), C32H34N402 (M) Example 28: Synthesis of 3- [4 -methylpiperazin-1-yl] carbonyl-4-naphthalen-1-yl) -1- [1- (3-phenyl) ropil-lH-imidazol-5-yl] methyl-lH-pyrrole (28) 62 mg were dissolved (0.2 mmol) of the compound to be prepared in Preparation 8 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added to 0 ° C and then the mixture was stirred for 5 minutes. 62 mg (2.2 mmol) of the compound to be prepared in Preparation 20 were introduced to the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 77 mg (yield: 74%) of the title compound. XH NMR (CDC13) d 1.01 (br, 2H), 2.80-2.01 (s + br + m, 6H), 2.30 (br, ÍH), 2.55 (t, 2H), 2.86 (br, 2H), 3.30 (br, 2H), 3.79 (t, 2H), 5.00 (s) , 2H), 6.58 (s, 1H), 7.00-7.20 (m, 8H), 7.36 (m, ÍH), 7.41 (m, 2H), 7.50 (s, ÍH), 7.74 (d, ÍH), 7.80 (d, HH), 8.00 (d, HH) FAB 518 (M + H), C33H 5 5N50 (M) Example 29: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl- 4- (naphthalen-1-yl) -1- [1- (naphthalen-2-yl) methyl-lH-imidazol-3-yl] methyl-lH-pyrrole (29) 62 mg (0.2 mmol) was dissolved of the compound which was prepared in Preparation 6 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 65 mg (2.2 mmol) of the compound to be prepared in Preparation 21 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95 / 5, v / v) to obtain 85 mg (yield: 80%) of the title compound. XH NMR (CDC13) d 2.36 (br, 2H), 2.72 (br, ÍH), 2.98 (br, 3H), 3.02 (br, 2H), 3.31 (br, ÍH) , 3.73 (br, ÍH), 3.10 (s, 2H), 5.47 (s, 2H), 6.58 (s, ÍH), 7.03 (s, ÍH), 7.08 ( d, ÍH), 7.15 (d, ÍH), 7.21 (s, ÍH), 7.34-7.53 (m, 7H), 7.60 (s, ÍH), 7.70-7 , 83 (m, 4H), 7.97 (d, ÍH) FAB 529 (M + H), C34H30N4O2 (M) Example 30: Synthesis of 3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalene -1-yl) -1- [1-naphthalen-2-yl) methyl-lH-imidazol-5-yl] methyl-lH-pyrrole (30) 62 mg (0.2 mmol) of the compound to be prepared was dissolved in Preparation 8 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) was added at 0 ° C and then the mixture was stirred for 5 minutes. 65 mg (2.2 mmol) of the compound to be prepared in Preparation 21 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that the mixture was extracted twice with 10 ml of ethyl acetateit was dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: 95/5, v / v) to obtain 74 mg (yield: 69%) of the title compound . XH NMR (CDC13) d 0.98 (br, 2H), 1.70-2.00 (s + br, 5H), 2.81 (br, 2H), 3.37 (br, ÍH), 4, 88 (s, 2H), 5.10 (s, 2H), 6.57 (s, ÍH), 7.02 (s, ÍH), 7.08 (d, ÍH), 7.16 (d, 1H) ), 7.21 (s, ÍH), 7.34-7.52 (m, 7H), 7.60 (s, ÍH), 7.70-7.83 (m, 4H), 7.97 ( d, ÍH) FAB 540 (M + H), C 35 H 33 N 50 (M) Example 31: Synthesis of 3- [N- (1-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -1- . { 1- [2- (naph alen-1-yl) ethyl] -1H-imidazol-5-yl} methyl-lH-pyrrole (31) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride were added ( 60%) at 0 ° C and then the mixture was stirred for 5 minutes. 68 mg (2.2 mmol) of the compound to be prepared in Preparation 22 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 77 mg (yield: 71%) of the title compound. XH NMR (CDC13) d 2.34 (br, 2H), 2.68 (br, ÍH), 2.80-3.20 (m, 5H), 3.23 (t, 2H), 3.29 ( br, 2H), 4.12 (t, 2H), 4.43 (s, 2H), 6.43 (m, 2H), 6.84 (d, ÍH), 6.97 (m, 2H), , 21-7.52 (m, 10H), 7.72 (d, ÍH), 7.78-7.83 (m, 2H), 8.01 (d, ÍH) FAB 543 (M + H), C35H34N402 (M) Example 32: Synthesis of -3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -1-. { 1- [2- (naphthalen-1-yl) ethyl] -lH-im-idazol-5-yl} methyl-lH-pyrrole (31) 62 mg (0.2 mmol) of the compound which was prepared in Preparation 8 was dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride were added ( 60%) at 0 ° C and then the mixture was stirred for 5 minutes. 68 mg (2.2 mmol) of the compound to be prepared in Preparation 22 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 83 mg (yield: 75%) of the title compound.

XH NMR (CDC13) d 1.01 (br, 2H), 1.70-2.00 (br + s, 5H), 2.89 (br, 2H), 3.27 (t, 2H), 3, 40 (br, 2H), 4.16 (t, 2H), 4.50 (s, 2H), 6.45 (d, ÍH), 6.90 (d, ÍH), 6.97 (d, ÍH) ), 6.99 (s, 1H), 7.25-7.55 (m, 8H), 7.73-7.95 (m, 5H), 8.00 (d, 1H) FAB 554 (M + H), C36H35N50 (M) Example 33: Synthesis of 1- [1- (4-bromo) phenethyl-1H-imidazol-5-yl] methyl-3- [N- (1-methoxyethyl) -N-methyl] carbamoyl -4- (naphthalen-1-yl) -lH-pyrrole (33) 62 mg (0.2 mmol) of the compound which was prepared in Preparation 6 was dissolved in 2 ml of dimethylformamide, 26.4 mg (0.degree. , 66 mmol) of sodium hydride (60%) a 0 ° C and then the mixture was stirred for 5 minutes. 74 mg (2.2 mmol) of the compound to be prepared in Preparation 23 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 88 mg (yield: 77%) of the title compound. XH NMR (CDC13) d 2.38 (br, 3H), 2.67 (t, 2H), 2.90-3.23 (m, 7H), 3.30 (br, ÍH), 3.97 ( t, 2H), 4.88 (s, ÍH), 6.69 (d, ÍH), 6.82 (d, 2H), 7.08 (d, 2H), 7.27-7.53 (m , 7H), 7.73 (d, ÍH), 7.80 (d, 1H), 8.02 (d, ÍH) FAB 571 (M + H), C31H3? N402Br (M) Example 34: Synthesis of 1 - [1- (4-bromo) phenethyl-lH-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (34) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 8 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 74 mg (2.2 mmol) of the compound to be prepared in Preparation 23 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 82 mg (yield: 70%) of the title compound. H NMR (CDC13) d 1.04 (br, 2H), 1.80-2.00 (br + s, 4H), 2.48 (br, ÍH), 2.66 (t, 2H), 2, 90 (br, 2H), 3.31 (br, ÍH), 2.96 (t, 2H), 4.88 (s, 2H), 6.70 (s, ÍH), 6.82 (d, 2H) ), 7.10 (d, 2H), 7.25-7.60 (m, 7H), 7.73 (d, 1H), 7.82 (d, ÍH), 8.01 (d, ÍH) FAB 582 (M + H), C 32 H 32 N 5 O Br (M) Example 35: Synthesis of 1- [1- (4-fluo) phenethyl-1 H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) - N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (35) 62 mg (0.2 mmol) of the compound which was prepared in Preparation 6 was dissolved in 2 ml of dimethylformamide, 26 , 4 mg (0.66 mmol) of sodium hydride (60%) a 0 ° C and then the mixture was stirred for 5 minutes. 60 mg (2.2 mmol) of the compound which was introduced into the mixture were introduced into the mixture. was prepared in Preparation 24 and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that the mixture was extracted twice with 10 ml of ethyl acetate, dried in sulphate Anhydrous sodium was added, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5, v / v) to obtain 77 mg (yield: 76%) of the title compound. XH NMR (CDC13) d 2.34 (br, 3H), 2.70 (t, 2H), 2.90-3.20 (br, 6H), 3.30 (br, ÍH), 3.96 (t, 2H), 4.86 (s, ÍH), 6.68 (d, ÍH), 6.90 (m, 4H), 7.03 (s, ÍH), 7.09 (s, ÍH) , 7.25-7.52 (m, 5H), 7.73 (d, HH), 8.05 (d, HH) FAB 511, (M + H), C3xH3 N N402F (M) Example 36: Synthesis of 1- [1- (4-fluo) phenethyl-1H-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -IH-pyrrole (36) 62 mg were dissolved (0, 2 mmol) of the compound to be prepared in Preparation 8 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 60 mg (2.2 mmol) of the compound to be prepared in Preparation 24 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 78 mg (yield: 75%) of the title compound. XH NMR (CDC13) d 1.05 (br, 2H), 1.70-2.00 (br + S, 4H), 2.23 (br, ÍH), 2.70 (t, 2H), 2, 90 (br, 2H), 3.30 (br, 2H), 3.88 (t, 2H), 4.87 (s, 2H), 6.69 (s, ÍH), 6.90 (m, 4H ), 7.10 (m, 2H), 7.29 (m, 2H), 7.35-7.50 (m, 3H), 7.74 (d, 1H), 7.82 (d, ÍH) , 8.00 (d, 1H) FAB 522 (M + H), C 32 H 32 N 5 OF '(M) Example 37: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- ( 4-methyl) f-nyl-lH-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -lH-pyrrole (37) 62 mg (0.2 mmol) of the compound to be prepared in the Preparation 6 in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 60 mg (2.2 mmol) of the compound to be prepared in Preparation 25 were introduced into the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 78 mg (yield: 80%) of the title compound. ? H NMR (CDC13) d 2.02 (br, ÍH), 2.28 (s, 3H), 2.38 (br, 2H), 2.70 (br, ÍH), 2.75 (t, 2H ), 2.95-3.20 (m, 5H), 3.31 (br, ÍH), 3.99 (t, 2H), 4.77 (s, 2H), 6.67 (s, ÍH) , 6.85 (d, 2H), 7.06 (m, 4H), 7.25-7.50 (m, 5H), 7.74 (d, ÍH), 7.81 (d, ÍH), 8.07 (d, HH) FAB 507 (M + H), C32H34N402 (M) Example 38: Synthesis of 1- [1- (4-methyl) phenethyl-lH-imidazol-5-yl] methyl-3- [ 4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (38) 62 mg (0.2 mmol) of the compound prepared in Preparation 8 were dissolved in 2 ml of dimethylformamide , 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 60 mg (2.2 mmol) of the compound to be prepared in Preparation 25 were introduced into the mixture and the whole mixture was stirred at room temperature for 3 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After this, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 81 mg (yield: 78%) of the title compound. 1ti NMR (CDC13) d 1.07 (br, ÍH), 1.70-2.10 (br + s, 6H), 2.28 (s, 3H), 2.73 (t, 2H), 2.90 (br, 2H), 3.33 (br, 2H), 4.00 (t, 2H), 4.78 (s, 2H), 6.72 (s, ÍH), 6.86 (m, 2H), 7.04-7.23 (m, 4H), 7.25-7.60 (m, 5H), 7.75 (d, ÍH), 7.82 (d, ÍH), 8.01 (d, ÍH) FAB 518 (M + H), C33H35N50 (M) Example 39: Synthesis of 1- [1- (4-chloro) phenethyl-1H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl ) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (39) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 64 mg (2.2 mmol) of the compound to be prepared in Preparation 26 were introduced to the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried in anhydrous sodium sulfate, concentrated and chromatographed. on a column of silica gel (eluent: dichloromethane / methanol = 95/5, v / v) to obtain 74 mg (yield: 70%) of the title compound. XH NMR (CDC13) d 2.38 (br, 2H), 2.70 (t, 2H), 2.90-3.20 (m, 7H), 3.30 (br, ÍH), 3.97 ( t, 2H), 4.88 (s, 2H), 6.69 (d, ÍH), 6.88 (d, 2H), 7.04 (s, ÍH), 7.09 (s, ÍH), 7.19 (d, 1H), 7.24-7.50 (m, 5H), 7.75 (d, IH), 7.81 (d, IH), 8.02 (d, IH) FAB 327 (M + H), C3? H3? N402Cl (M) Example 40: Synthesis of 1- [1- (4-chloro) phenethyl-lH-imidazol-5-yl] methyl] -3- [4-methyl-piperazine] 1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (40) 62 mg (0.2 mmol) of the compound to be prepared in Preparation 8 were dissolved in 2 ml of dimethylformamide, 26 , 4 mg (0.66 mmol) of sodium hydride (60%) at 0 ° C and then the mixture was stirred for 5 minutes. 64 mg (2.2 mmol) of the compound to be prepared in Preparation 26 were introduced to the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried in anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = • 95 / 5, v / v) to obtain 84 mg (yield: 78%) of the title compound. XH NMR (CDC13) d 1.08 (br, 2H), 1.80 (br, 2H), 1.95 (s, 3H), 2.73 (t, 2H), 2.93 (br, 2H), 3 , 35 (br, 2H), 4.00 (t, 2H), 4.90 (s, 2H), 6.71 (d, ÍH), 6.91 (d, 2H), 7.13-7, 60 (m, 9H), 7.78 (d, ÍH), 7.82 (d, ÍH), 8.01 (d, ÍH) FAB 338 (M + H), C32H32N50C1 (M) Example 41: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naph talen-1-yl) -1-. { 1- [2- (naph alen-2-yl) ethyl] -1H-imidazol-5-yl} methyl-lH-pyrrole (41) 11. 62 mg (0.2 mmol) of the compound that was prepared in Preparation 6 were dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride (60%) were added at 0 ° C and then the mixture was stirred for 5 minutes. 67 mg (2.2 mmol) of the compound to be prepared in Preparation 27 were introduced to the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried in anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5, v / v) to obtain 79 mg (yield: 71%) of the title compound. 1 H NMR (CDC13) d 2.96 (br, 1H), 2.39 (br, 2H), 2.71 (br, 1H), 2.80-3.15 (m, 7H), 3.32 ( br, ÍH), 4.10 (t, 2H), 4.78 (s, ÍH), 6.66 (s, ÍH), 7.09 (m, 3H), 7.42 (m, 8H), 7.63 (m, HH), 7.75 (m, 3H), 7.82 (d, HH), 8.06 (d, HH) FAB 543 (M + H), C35H34N402 (M) Example 42: Synthesis of 3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -1-. { 1- [2- (naph alen-2-yl) ethyl] -iH-im-idazol-5-yl} methyl-lH-pyrrole (42) 62 mg (0.2 mmol) of the compound which was prepared in Preparation 8 was dissolved in 2 ml of dimethylformamide, 26.4 mg (0.66 mmol) of sodium hydride were added ( 60%) a 0 ° C and then the mixture was stirred for 5 minutes. 67 mg (2.2 mmol) of the compound to be prepared in Preparation 27 were introduced to the mixture and the whole mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure and 3 ml of water was introduced into the residue. After that, the mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 95/5 , v / v) to obtain 82 mg (yield: 74%) of the title compound. XH -NMR (CDC13) d 1.05 (br, 2H), 1.70-2.00 (s + br, 4H), 2.34 (br, ÍH), 2.90 (t, 2H), 3 , 01 (br, 2H), 3.32 (br, 2H), 4.08 (t, 2H), 4.78 (s, 2H), 6.65 (d, 2H), 7.10 (m, 3H), 7.21-7.42 (m, 7H), 7.64 (m, 1H), 7.75 (m, 3H), 7.82 (d, IH), 8.01 (d, IH) ) FAB 554 (M + H), C36H35N50 (M) Example 43: Synthesis of 1- [1- (4-hydroxy) phenethyl-1H-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] ] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (43) 53 mg (0.1 mmol) of the compound prepared in Example 20 were dissolved in 1.2 dichloromethane, 75 mg was added (0.3 mmol) of boron hydrobromide (BBr3), and the mixture was stirred for 3 hours. 1 1 methanol was introduced to terminate the reaction and the solvent was removed by distillation under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 20/80, v / v) to obtain 26 mg (yield: 50%) of the title compound. 1 NMR (CDC13) d "1.20 (br, 2H), 1.80-2.05 (br + s, 4H), 2.65 (t, 2H), 3.00-3.60 (br, 5H), 3.98 (t, 2H), 4.88 (s, 2H), 6.72 (m, 5H), 7.09 (s, ÍH), 7.14 (d, ÍH), 7, 23 (s, ÍH), F 7.27 (s, ÍH), 7.33 (d, ÍH), 7.40-7.53 (m, 3H), 7.77 (d, ÍH), 7, 82 (d, ÍH), 1, 93 (d, ÍH) FAB 520 (M + H), C32H3302N5 (M) Preparation 28: Synthesis of 4- (chloromethyl-1-trityl-lH-imidazole Hydrochloride _28-l) 4-hydroxymethyl-1-trityl-lh-imidazole. 3.99 mg (29.6 mmol) of hydrochloride were added.

^ W hydroxymethyl-imidazole in a mixture of 30 ml of dimethylformamide and 10 ml of triethylamine. Then, slowly, a solution of 9.25 g (33.5 mmol) of triphenylmethyl chloride in 110 ml of dimethylformamide was added thereto.

After two hours, 500 ml of water was added to the reaction mixture to obtain a solid. This solid was recrystallized from dioxane to obtain 8.82 g (87% yield) of the title compound. P.f .: 227-229 ° C. 20 28-2) 4-Chloromethyl-1-trityl-1H-imidazole hydrochloride 1.50 g (4.41 mmol) of the compound to be prepared in Preparation 28-1) were dissolved in 50 ml of chloroform , 0.94 ml (13.2 mmol) of thionyl chloride (60%) was slowly added thereto, at 0 ° C, and then the mixture was stirred. room temperature for 2 hours. The organic solvent was removed under reduced pressure to obtain 1.66 g (4.20 mmol, 95% yield) of the title compound, which was used directly in the next reaction, without purification. Preparation 29: Synthesis of 4- (5-chloromethyl-1H-imidazol-1-ylmethyl) benzonitrile 29-1) 4-Acetoxymethyl-1-trityl-1H-imidazole To 100 ml of pyridine was added 5.00 g (14.7 mmol) of the compound prepared in Preparation 28-1) and 1.65 g (16.2 mmol) of acetic anhydride and the mixture was stirred at room temperature for 24 hours. The reaction solution was distilled under reduced pressure to remove the pyridine and then the residue was dissolved in 200 ml of ethyl acetate and washed with 100 ml of an aqueous solution of sodium chloride. The organic solvent was distilled off under reduced pressure and the residue was subjected to column chromatography (eluent: dichloromethane / methanol = 20/1, v / v) to obtain 5.22 g (13.7 mmol, 93% yield) of the title compound. XH NMR (CDC13) d 2.01 (s, 3H), 4.95 (s, 2H), 6.88 (s, ÍH), 7.08 (s, 5H), 7.27 (s, 10H) , 7.45 (s, 1H) 29-2) 4- (4-Acetoxymethyl-1-trityl-1H-imidazol-3-ylmethyl) benzonitrile, 00 g (13.1 mmol) of the compound prepared in Preparation 29-1) was dissolved in 20 ml of dichloromethane, 2.82 g (14.4 mmol) of 4-cyanobenzyl bromide and The mixture was stirred at room temperature for 60 hours. The organic solvent was distilled off under reduced pressure and the residue was subjected to column chromatography (eluent: dichloromethane / methanol = 5/1, v / v) to obtain 5.31 g (9.17 mmol, yield 70%) of the title compound. NMR (CDC13 + CD30D) d 1.95 (s, 3H), 4.95 (s, 2H), 5.45 (s, 2H), 7.11-7.40 (m, 18H), 7.65 (d, 2H), 8.21 (s, ÍH). 29-3) 4 - (5-Acetoxymethyl-1H-imidazol-1-ylmethyl) benzonyl trile 9.10 g (15.7 mmol) of the compound prepared in Preparation 29-2) were dissolved in 500 ml of dichloromethane. There, 6.06 ml (78.7 mmol) of trifluoroacetic acid and 12.5 ml (78.7 mmol) of triethylsilane were slowly added at 0 ° C and the mixture was stirred at room temperature for 1 hour. The organic solvent was distilled off under reduced pressure and then the residue was adjusted to pH 10 with an aqueous solution of saturated K2CO3 and extracted with 300 ml of ethyl acetate. The organic solvent was distilled off under reduced pressure and the residue was subjected to column chromatography using ethyl acetate as eluent, to obtain 3.60 g (14.1 mmol, yield 90%) of the title compound. 1H NMR (CDC13) d 1.90 (s, 3H), 4.97 (s, 2H), 5.25 (s, 2H), 7.14 (d, 2H), 7.21 (d, ÍH) , 7.67 (s, 1H) ', 7.75 (d, 2H) 29-4) 4- (5-Hydroxymethyl-1H-imidazol-1-ylmethyl) benzonitrile 4.20 g (16.5 mmol) were dissolved. ) - of the compound prepared in Preparation 29-3) in 200 ml of methanol; there were incorporated 4.50 g (32.9 mmol) of K2CO3 and the mixture was stirred at room temperature for 20 minutes. The organic solvent was removed by distillation under reduced pressure at room temperature. Then the residue was extracted with 300 ml of ethyl acetate and the extract was subjected to column chromatography (eluent: dichloromethane / methanol = 10/1, v / v) to obtain 3.19 g (15.0 mmol, yield 91 %) of the title compound. XH NMR (CDC13 + CD30D) d 4.28 (s, 2H), 5.18 (s, 2H), 6.84 (s, ÍH), 7.12 (d, 2H), 7.42 (s, ÍH), 7.55 (d, 2H) 29-5) 4- (5-Chloromethyl-lH-imidazol-1-methylmethyl) benzonyl triohydrochloride 3.00 g (14.1 mmol) of the compound prepared in the Preparation 29-4) were dissolved in 40 ml of chloroform; There 5.02 ml (70.5 mmol) of thionyl chloride were added slowly at 0 ° C and the mixture was stirred at room temperature for 2 hours. The organic solvent was removed under reduced pressure to obtain 3.50 g (13.1 mmol, 93% yield) of the title compound. This compound was used directly in the next reaction without purification. Preparation 30: Synthesis of 4- (3-chloro-l-propenyl) -1-trityl-lH-imidazole 30-1) methyl 3- (lH-imidazole-4-yl) acrylate 500 mg (3, 62 mmol) of 3- (1H-imidazol-4-yl) acrylic acid to 20 ml of methanolic HCl and the mixture was stirred at room temperature for 10 hours. The solvent was removed under reduced pressure and then 30 ml of dichloromethane was added to the residue. The mixture was washed sequentially with a solution of saturated NaHCO 3, an aqueous solution of sodium chloride and water. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain 510 mg (3.35 mmol, 93% yield) of the title compound. This compound was used directly in the next reaction without purification. 30-2) 3- (1-Trityl-1H-imidazol-4-yl) methyl acrylate 350 mg (2.30 mmol) of the compound prepared in Preparation 30-1) and 705 mg (2.53 mmol) of The triphenylmethyl chloride was dissolved in 10 ml of dimethylformamide and therein was added 350 μl (2.53 mmol) of triethylamine. After 2 hours, 100 ml of ice water was added to the reaction mixture to obtain a solid. This solid was filtered, washed with diethyl ether and hexane and then dried to obtain 810 mg (2.05 mmol, 87% yield) of the title compound. XH NMR (CDC13) d 3.75 (s, 3H), 6.35 (d, ÍH), 7.05-7.50 (m, 18H). 30-3) 1- (1-Trityl-1H-imidazol-4-yl) propen-3-ol 800 mg (2.03 mmol) of the compound prepared in Preparation 30-2) were added to 20 ml of dry dichloromethane. . After cooling the mixture to -78 ° C, 6.1 ml (IM solution in hexane) of diisobutyl aluminum hydride were added thereto. The temperature was slowly raised to room temperature and then 2 ml of water was added to the mixture to stop the reaction. 3 ml of IN NaOH were added and then 2 ml of water and the mixture was filtered through celite. The organic layer of the filtrate was separated and combined with the dichloromethane extract of the aqueous layer. The mixture was dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and the residue was subjected to column chromatography (eluent: dichloromethane / methanol = 20/1, v / v) to obtain 671 mg (1.83 mmol, yield 90%) of the title compound . XH NMR (CDC13) d 4.25 (s, 2H), 6.45 (s, 2H), 6.78 (s, ÍH), 7.10-7.50 (m, 16H) 30-4) 4 - (3-Chloropropenyl) -1-trityl-1H-imidazole 650 mg (1.77 mmol) of the compound prepared in Preparation 30-3) were added to 10 ml of chloroform. There 135 μl (1.9 mmol) of thionyl chloride were added at 0 ° C and the mixture was stirred at room temperature for 2 hours. The organic solvent was distilled off under reduced pressure and the residue was dissolved in 10 ml of ethyl acetate. The solution was washed with an aqueous solution of saturated NaHCO 3 and the organic solvent was distilled off under reduced pressure to obtain 647 mg (1.68 mmol, 95% yield) of the title compound. ? ti NMR (CDC13) d 4.22 (d, 2H), 6.40-6.55 (m, 2H), 6.81 (s, ÍH), 7.10-7.50 (m, 16H) Preparation 31: Synthesis of 5-chloromethyl-1-methylimidazole hydrochloride 31 -1) 5-Hydroxymethyl-1-methylimidazole The title compound was obtained in a yield of 32% according to the procedure described in J.M.Dener, L-H Zhang, H. Rapoport, J. Org. Chem., 1993, 58, 1159, using dihydroxy-acetone and methylamine hydrochloride as starting materials. XH NMR (CDC13) d 3.67 (s, 3H), 4.58 (s, 2H), 5.37 (brs, ÍH), 6.76 (s, ÍH), 7.32 (s, ÍH) 31 -2) 5-Chloromethyl-1-methylimidazole hydrochloride The title compound was obtained in 95% yield according to the same procedure used in Preparation 28-2) with the exception that the compound to be prepared in Preparation 31-1) was used as a starting material. Preparation 32: Synthesis of hydrochloride 1- (4-bromobenzyl) -5-chloromethyl-lH-imidazole 32-1) 1- (4-Bromobenzyl) -5-hydroxymethyl-1H-imidazole The title compound was obtained in 50% yield according to procedure that is described in J.M.Dener, L-H Zhang, H. Rapoport, J. Org. Chem., 1993, 58, 1159, using a dihydroxyacetone dimer and hydrochloride 4-bromobenzyl-amine as starting materials. XH NMR (CDC13 + CD3OD) d 4.46 (s, 2H), 5.26 (s, 2H), 7.00 (s, ÍH), 7.07 (d, 2H), 7.50 (d, 2H), 7.65 (s, ÍH) 32-2) Chlorhydrate to 1 - (4-Bromobenzyl) -5-chloromethyl-lH-imidazole The title compound was obtained in 96% yield according to the same procedure as that used in Preparation 28-2), with the exception that the compound to be prepared in Preparation 32-1) was used as a start material The product obtained in this way was used directly in the next reaction without purification. Preparation 33: Synthesis of 5-chloromethyl-1-isobutylimidazole Hydrochloride 33-1) 5-Hydroxymethyl-1-isobutylimidazole The title compound was obtained in 45% yield according to the same procedure as that used in Preparation 31 -1) using dihydroxyacetone and isobutylamine hydrochloride as starting materials. 1ti NMR (CDC13) d 0.90 (d, 6H), 1.76 (m, ÍH), 3.62 (d, 2H), 4.24 (brs, ÍH), 4.60 (s, 2H) , 6.85 (s, 1H), 7.45 (s, 1H) FAB (M + H): 155 33-2) 5-Chloromethyl-1-isobutylimidazole hydrochloride The title compound was obtained with a yield of 95% according to the same procedure as that used in Preparation 28-2), with the exception that the compound to be prepared in Preparation 33-1) was used as a starting material. Preparation 34: Synthesis of 5-chloromethyl-1-cyclohexylmethyl-imidazole 34-1 Hydrochloride 5-Hydroxymethyl-1-cyclohexylmethylimidazole The title compound was obtained in 45% yield according to the same procedure as it will be used in Preparation 31-1) using dihydroxyacetone and cyclohexylmethylamine hydrochloride as starting materials. XH NMR (CDC13) d 0.94 (m, 2H), 1.16 (m, 3H), 1.50-1, 70 (m, 6H), 3.65 (d, 2H), 4.24 ( brs, 1H), 4.60 (s, 2H), 6.85 (s, 1H), 7.45 (s, ÍH) FAB (M + H): 195 34-2) 5-Chloromethyl hydrochloride l -cyclohexylmethyl-imidazole The title compound was obtained in 95% yield according to the same procedure as that used in Preparation 28-2), with the exception that the compound to be prepared in Preparation 34-1) was used as a start material Preparation 35: Synthesis of 5-chloromethyl-1-pentylimidazole hydrochloride 35-1) 5-Hydrox imetyl-1-pentyl imide zol The title compound was obtained in 50% yield according to the same procedure as that used in Preparation 31-1), using dihydroxyacetone and pentylamine hydrochloride as starting materials. XH NMR (CDC13) d 0.90 (t, 3H), 1.08 (brs, 2H), 1.30 (m, 4H), 1.45 (m, 2H), 3.64 (t, 2H) , 4.24 (brs, ÍH), 4.60 (s, 2H), 6.84 (s, ÍH), 7.44 (s, lH) FAB (M + H): 169 35-2) Hydrochloride 5-chloromethyl-l-pentylimidazole The title compound was obtained with a yield of 90% according to the same procedure as that used in Preparation 28-2), with the exception that the compound to be prepared in Preparation 35-1) was used as a starting material. Preparation 36: Synthesis of 5-chloromethyl-1-octylimidazole hydrochloride 36-1) 5-Hydroxymethyl-1-octylimidazole The title compound was obtained in a yield of 52% according to the same procedure as that used in Preparation 31-1) using dihydroxyacetone and octylamine hydrochloride as starting materials. XH NMR (CDC13) d 0, 88 (t, 3H), 1.18 (brs, 2H), 1.30 (brs, 10H), 1.42 (m, 2H), 3.67 (t, 2H), 4.23 (brs, 1H), 4.60 (s, 2H), 6.84 (s, ÍH), 7.44 (s, ÍH) FAB (M + H): 211 36-2) Chlorohydrate of 5-chloromethyl-1 - octylimidazole The title compound was obtained with a yield of 93% according to the same procedure as that used in Preparation 28-2), with the exception that the compound that was prepared in Preparation 36-1) was used as a starting material. Preparation 37: Synthesis of 5-chloromethyl-1-decylimidazole hydrochloride 37-1) 5-Hydroxymethyl-1-decyl imidazole The title compound was obtained in a yield of 52% according to the same procedure as that used in Preparation 31-1), using dihydroxyacetone and decylamine hydrochloride as starting materials. XH NMR (CDC13). d 0.88 (t, 3H), 1.04 (brs, 2H), 1.30 (brs, 14H), 1.42 (m, 2H), 3.68 (t, 2H), 4.23 ( brs, ÍH), 4.60 (s, 2H), 6.84 (s, ÍH), 7.44 (s, ÍH). FAB (M + H): 239 37-2) 5-Chloromethyl-1-decylimidazole hydrochloride The title compound was obtained in 93% yield according to the same procedure as that used in Preparation 28-2) with the exception that the compound to be prepared - in Preparation 37-1) was used as a starting material. Preparation 38: Synthesis of 5-chloromethyl-1- (3-methyl) butylimidazole 38-1) 5-Hydroxymethyl-1- (3-methyl) butylimidazole hydrochloride The title compound was obtained in a yield of 52% according to the same procedure as that used in Preparation 31-1), using dihydroxyacetone and isoamylamine hydrochloride as starting materials. 1 NM NMR (CDCl 3) δ 0.90 (d, 6H), 1.32 (m, 2H), 1.65 (m, HH), 3.67 (t, 2H), 4.23 (brs, HH) , 4.60 (s, 2H), 6.84 (s, ÍH), 7.44 (s, ÍH). FAB (M + H): 169 38-2) 5-Chloromethyl-1 - (3-methyl) butylimidazole hydrochloride The title compound was obtained in a yield of 93% according to the same procedure as that used in Preparation 28-2), with the exception that the compound that was prepared in Preparation 38-1) was used as a starting material. Preparation 39: Synthesis of 5-chloromethyl-1- (2-methoxy) ethylimidazole hydrochloride 39-1) 5-Hydroxymethyl-1 - (2-methoxy) ethylimidazole The title compound was obtained in a yield of 60% according to the same procedure as that used in Preparation 31-1), using dihydroxyacetone and 2-methoxyethylamine hydrochloride as starting materials. 1 NMR (CDC13) d 3.38 (s, 3H), 3.42 (t, 2H), 3.65 (t, 2H), 4.23 (brs, ÍH), 4.60 (s, 2H) 6.84 (s, ÍH), 7.44 (s, 1H) FAB (M + H): 157 39-2) 5-Chloromethyl-1- (2-methoxy) ethylimidazole hydrochloride The title compound was obtained with a yield of 93% according to the same procedure as that used in Preparation 28-2), with the exception that the compound that was prepared in Preparation 39-1) was used as a starting material.

Preparation 40: Synthesis of 5-chloromethyl-1- (3-methoxy) propylimidazole 40-1) 5-Hydroxymethyl-1- (3-methoxy) propylimidazole hydrochloride The title compound was obtained in a 61% yield according to the same procedure as that used in Preparation 31-1) using dihydroxyacetone and 3-methoxypropylamine hydrochloride as starting materials.

XH NMR (CDC13) d 1.72 (m, 2H), 3.32 (s, 3H), 3.46 (t, 2H), 3.63 (t, 2H), 4.23 (brs, ÍH) , 4.60 (s, 2H), 6.84 (s, ÍH), 7.44 (s, ÍH) FAB (M + H): 171 40-2) 5-Chloromethyl-1 - (3- methoxy) propylimidazole The title compound was obtained with a yield of 90% according to the same procedure as that used in Preparation 28-2), with the exception that the compound prepared in Preparation 40-1) was used as a starting material. Preparation 41: Synthesis of 5-chloromethyl-1- (3-ethoxy) -ropilimidazole 41 -1) 5-Hydroxymethyl-1- (3-ethoxy) propylimidazole hydrochloride The title compound was obtained in a 61% yield according to with the same procedure as that used in Preparation 31-1) using dihydroxyacetone and 3-ethoxypropylamine hydrochloride as starting materials. XH NMR (CDC13) d 1.20 (t, 3H), 1.72 (m, 2H), 3.50 (s, 4H), 3.63 (t, 2H), 4.23 (brs, ÍH), 4.60 (s, 2H), 6.84 (s, ÍH), 7.44 (s, ÍH) FAB (M + H): 185 41 -2) 5-Chloromethyl-l - (3) Chlorhydrate -ethoxy) propylimidazole The title compound was obtained in 90% yield according to the same procedure as that used in Preparation 28-2), with the exception of the compound to be prepared in Preparation 41-1) It was used as a starting material. Preparation 42: Synthesis of 5-chloromethyl-1- (3-isopropoxy) propylimidazole 42-1) 5-Hydroxymethyl-1 - (3-isopropoxy) propylimidazole hydrochloride The title compound was obtained in 61% yield according to the same procedure as that used in Preparation 31-1), using dihydroxyacetone and 3-isopropoxy-propylamine hydrochloride as starting materials. XH NMR (CDC13) d 1.15 (d, 6H), 1.71 (m, 2H), 3.45-3.55 (m, 3H), 3.63 (t, 2H), 4.23 ( brs, ÍH), 4.60 (s, 2H), 6.84 (s, 1H), 7.44 (s, ÍH) FAB (M + H): 199 42-2) - 5-Chloromethyl Hydrochloride -l- (3-isopropoxy) propylimidazole The title compound was obtained in 90% yield according to the same procedure as that used in Preparation 28-2), with the exception that the compound to be prepared in the Preparation 42-1) was used as a starting material. Example 44: Synthesis of 1- (lH-imidazol-4-yl) methyl-4- (nalen-1-yl) -3- (thiophen-2-yl) carbonyl-lH-pyrrole (44) 44 -1) 3- (Naphthalen-1 -yl) -1 - (thiophen-2-yl) -prop-2-en-l -one 3.12 g (20 mmol) of 1-naphthaldehyde and 2.52 g (20 mmol) of 2-acetylthiophene were dissolved in 20 ml of methanol and 800 mg (20 mmol) of sodium hydroxide were slowly added therein. The mixture was reacted at room temperature for 8 hours and then, the solid produced in this way was filtered and dried. The filtrate was adjusted to pH 4-6, using a solution of IN hydrochloric acid and extracted with ethyl acetate. The organic solvent was removed under reduced pressure and the residue was subjected to column chromatography (eluent: hexane / ethyl acetate = 4 μl, v / v) to obtain 4.23 g (16 mmol, 80% yield) of the compound of the title together with the filtered solid. XH NMR (CDC13) d 7.13-7.31 (m, 2H), 7.55-7.70 (m, 3H), 7.70 (d, 1H), 7.85-7.90 (m , 4H), 8.28 (d, HH), 8.70 (d, HH) 44-2) 4- (Naphthalen-1 -yl) -3- (thiophen-2-yl) carbonyl-lH-pyrrole 2 , 64 g (9.99 mmol) of the compound prepared in Example 44-1) and 2.35 g (12.0 mmol) of tosylmethyl isocyanide were dissolved in 30 ml of tetrahydrofuran. There 1.35 g (12.0 mmol) of potassium t-butoxide were slowly added and the mixture refluxed for 30 minutes. The solvent was removed under reduced pressure and then 15 ml of water and 20 ml of ethyl acetate were added to the residue. The mixture was vigorously stirred and filtered to obtain the resulting solid. This solid was washed with diethyl ether and dried to obtain 1.97 g (6.48 mmol, 65% yield) of the title compound. 1NMR (CDC13) d 6.90 (s, 1H), 7.12 (s, 1H), 7.20-7.45 (m, 4H), 7.55 (s, ÍH), 7.61 ( s, ÍH), 7.70-8.00 (m, 4H), 11.4 (s, ÍH). 44-3) 4 - (Naphthalen-1 -yl) -3- (thiophen-2-yl) carbonyl -1 - (1 -trityl-1H-imidazo 1-4 -yl) met il-lH-p ir rol 200 mg (0.99 mmol) of the compound prepared in Example 44-2) was dissolved in 5 ml of dimethylformamide; there 95 mg (4.0 mmol) of sodium hydride (50%) were added at 0 ° C and the mixture was stirred for 5 minutes. 391 mg (0.99 mmol) of the compound prepared in Preparation 28-2) was added to the reaction solution and stirred at room temperature for 5 hours. The solvent was removed by distillation under reduced pressure and the residue was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated and subjected to column chromatography (eluent: hexane / ethyl acetate = 1/3, v / v) to obtain 205 mg (0.33 mmol, 33% yield) of the title compound. 1H NMR (CDC13) d 5.02 (s, 2H), 6.75 (s, ÍH), 6.79 (s, ÍH), 6.86 (t, ÍH), 7.10-7.52 ( m, 23H), 7.71 (d, ÍH), 7.78 (d, 1H), 7.89 (d, ÍH) 44-4) 1 - (lH-lmidazole -4-yl) ethyl -4- (naphthalen-1 -il) -3- (thiophen-2-yl) carbonyl-lH-pyrrole 190 mg (0.304 mmol) of the compound prepared in Example 44-3) were dissolved in a solvent mixture of trifluoroacetic acid / dichloromethane (0.5 ml / 0, 5 ml) and the solution was stirred at room temperature, for 2 hours. The organic solvent was removed under reduced pressure. The residue was dissolved in 10 ml of ethyl acetate, washed with a saturated Na 2 CO 3 solution and water, dried over anhydrous magnesium sulfate, concentrated and subjected to column chromatography (eluent: ethyl acetate), to obtain 103 mg (0.269 mmol, 88% yield) of the title compound. •? Ti NMR (CDC13) d 4.87 (s, 2H), 6.55 (s, ÍH), 6.72 (s, ÍH), 6.88 (t, ÍH), 7.11-7, 34 (m, 7H), 7.50-7.67 (m, 3H), 7.83 (d, ÍH) FAB MS: 384 (M + l) EXAMPLES 45 A 72: The compounds represented in the following Tables 2 -1 to 2-3 were obtained according to the similar procedure of Example 44. • and • TABLE 2-2 Comp. 1H NMR (CDC13) d FAB No. MS (M + l) 52.21 (s, 3H), 4.92 (s, 2H), 6.62 (s, ÍH), 6.83 (s, ÍH), 392 7, 14-7, 35 (m, 8H), 7, 61-7, 73 (m, 5H), 7.88 (d, ÍH) 53 3,66 (s, 3H), 5,04 (s, 2H), 6,85 (s, ÍH), 6,82 (d, ÍH), 408 6,90 (m, ÍH), 7,12 -7, 17 (m, 2H), 7.26-7.36 < m, 8H), 7.67 (t, ÍH), 7.74 (d, ÍH), 7.93 (d, ÍH) 54 3.75 (s, 3H), 5.02 (s, 2H), 6.71 (m, 3H), 6.80 (t, ÍH), 408 7.20-7.35 (m, 6H), 7, 60-7, 75 (, 4H), 7.91 (d, ÍH) 55 4.83 (s, 2H), 6.51 (s, ÍH), 6.63 (s, ÍH), 6, 85 (m, ÍH), 412 7.03-7.29 (m, 10H), 7, 61-7, 69 (m, 2H), 7.83 (d, ÍH) 56 5.01 (s, 2H), 6.72 (s, ÍH), 6.77 (s, ÍH), 7.22-7.35 (m, 412 11H), 7.61-7, 80 (m, 3H) 57 4.82 (s, 2H), 6.63 (s, 1H), 6.72 (s, ÍH), 7.02-7.24 (m, 446 10H), 7.56-7, 70 (m, 3H) 58 4.91 (s, 2H), 6.65 (s, ÍH), 6.77 (m, ÍH), 7, 20-7, 31 (m, 396 7H), 7.61 (m, 3H), 7.81 (d, 1H) 59 4.92 (s, 2H), 6.45 (ra, ÍH), 6.71 (m, 2H), 7, 20-7, 32 (m, 414 9H), 7.63-7, 77 (m, 3H) 60 5.09 (s, 2H), 6.80-7.20 (m, 4H), 7, 15-7, 35 (m, 4H), 403 7.40 (d, ÍH), TABLE 2-3 • Example 73: Synthesis of 1- [1- (4-cyanobenzyl) -1H-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -3- (thiophen-2-yl) carbonyl-lH-pyrrole (73) 80 mg (0.3 mmol) of the compound prepared in Preparation 29-5) and 90 mg (0.3 mmol) of the compound prepared in Example 44-2) were dissolved in 2 ml of dimethylformamide; There, 36 mg of hydride of # Sodium (60%) and the mixture was stirred for 2 hours. The solvent was removed by distillation under reduced pressure and the residue was subjected to column chromatography (eluent: dichloromethane / methanol = 10/1, v / v) to obtain 83 mg (0.17 mmol, 56% yield) of the title compound . xti NMR (CDC13) d 5.02 (s, 2H), 5.08 (s, ÍH), 6.73 (s, ÍH), 6.85 (s, ÍH), 7.03 (t, ÍH), 7.32-7.45 (m, 11H), 7.63 (s, ÍH), 7.75 (d, ÍH), 7.82 (d, ÍH), 8.02 (d, ÍH).

FAB MS: 499 (M + 1) Example 74 to 77: The compounds represented in the following Table 3 were obtained according to the procedure similar to that of Example 73. TABLE 3 Example 78: Synthesis of 3- (4-fluobenzoyl) -1- (1-methyl-lH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (78) The title compound was obtained in 75% yield according to the same procedure as that used in Example 44-3), with the exception that 3- (4-fluobenzoyl) -4- (naphthalene- 1-yl) -lH-pyrrole and the compound prepared in Preparation 31-2). XH NMR (CDC13) d 3.42 (s, 3H), 5.01 (s, 2H), 6.73 (m, 3H), 7.11 (s, ÍH), 7.24-7.57 ( m, 8H), 7.67-7.75 (m, 2H). FAB MS (M + 1): 410 Example 79: Synthesis of 1- (1-methyl-lH-imidazol-4-yl) ethyl-4- (na talen-1-yl) -3- (4-phenoxybenzoyl) - lH-pyrrole (79) The title compound was obtained in a 70% yield according to the same procedure as that used in Example 44-3) with the exception that 4- (naphthalen-1-yl) was used. ) -3- (4-phenoxybenzoyl) -lH-pyrrole and the compound prepared in Preparation 31-2). XH NMR (CDC13) d 3.52 (s, 3H), 5.12 (s, 2H), 6.63 (d, 2H), 6.76 (d, ÍH), 6.85 (d, 2H) , 7.12 (t, ÍH), 7.20 (s, 1H), 7.28-7.40 (m, 7H), 7.51 (d, 2H), 7.68 (d, 2H), 7.74 (d, ÍH), 7, 83 (d, ÍH). FAB MS (M + 1): 484 Example 80: Synthesis of (S) -1- (1H-imidazol-4-yl) methyl-3- [N- (1-methoxycarbonyl-3-methylthio) propyl] carbamoyl-4 - (naphthalen-1-yl) -lH-pyrrole (80) 80-1) Ethyl 3- (naph talen-1-yl) acrylate 22.4 g (0.10 mole) of triethylphosphonoacetate were dissolved 500 ml of tetrahydrofuran and 12.4 g (1.1 mol) of potassium butoxide were slowly added thereto. To this solution were slowly added 15.6 g (0.10 mol) of 1-naphthaldehyde dissolved in 20 ml of tetrahydrofuran and the mixture was stirred for 8 hours. The organic solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate, washed twice with water, Dried in anhydrous magnesium sulfate, concentrated and subjected to column chromatography (eluent: hexane / ethyl acetate = 95/5, v / v) to obtain 20.3 g (0.090 mol, yield 90%) of the composed of the title. XH NMR (CDC13) d 1.42 (t, 3H), 4.30 (q, 2H), 6.50 (d, ÍH), 7.40-7.60 (m, 3H), 7.73 ( d, ÍH), 7.82 (m, 2H), 8.20 (d, ÍH), .8.50 (d, 1H). 80-2) 3-Ethoxycarbonyl-4- (naphthalen-1-yl) -IH-pyrrole 500 mg (1.89 mmol) of ethyl 3- (naphthalen-1-yl) acrylate to be prepared in Example 80-1 ) and 368 mg (1.89 mmol) of tosylmethyl isocyanide were dissolved in 10 ml of tetrahydrofuran. There, 255 mg (2.27 mmol) of potassium t-butoxide dissolved in tetrahydrofuran (10 ml) were added slowly and the mixture was refluxed for 30 minutes. 10 ml of water was added to the reaction solution to stop the reaction and the solvent was removed • 20 at reduced pressure. The residue was extracted with diethyl ether, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to column chromatography (eluent: ethyl acetate / hexane = 1/3, v / v) to obtain 385 mg (1.45 mmol, 77% yield) of the title compound. XH NMR (CDC13) d 0.86 (t, 3H), 4.02 (q, 2H), 6.81 (s, ÍH), 7.48-7.61 (m, 5H), 7.90- 7.97 (m, 3H), 8.92 (s, ÍH). 80-3) 3-Ethoxycarbonyl-1 - (12-2-imide zol-4-yl) methyl-4- (naphthalen-1-yl) -IH-pyrrole The title compound was obtained with a yield of 39% by applying the procedure described in Examples 44-3) 'and 44-4) of the compounds to be prepared in Example 80-2) and in Preparation 2? -2). XH NMR (CDC13) d 1.11 (t, 3H), 4.22 iq, 2H), 5.05 (s, 2H), 6.78 (s, 1H), 6.89 (s, ÍH), 7.38-7.49, m, 6H), 7.85-7.97 (m, 3H) 80-4). 3-Hydroxycarbonyl-1 - (1H-imide zol-4-yl) methyl-4 - (naphthalen-1-yl) -lH-pyrrole 220 mg (0.64 mmol) of the compound prepared in Example 80-3) they were dissolved in 5 ml of 50% ernol. There, 216 mg (3.8 mmol) of potassium hydroxide were added dropwise and the mixture was refluxed for hours. The reaction solution was cooled until reaching r. =. The atmosphere was adjusted to pH 4-5, extracted with ethyl acetate and dried over anhydrous sodium sulfate. The soltent therein was removed under reduced pressure to obtain 162 mg (0.51 mmol, 80% yield) of the t z lo compound. This compound was used directly in the next reaction without purification. XH NMR (CD30D + CDC13) d 5.01 (s, _ :: -), 6.82 (s, ÍH), 6.87 (s, ÍH), 7.42-7.70 (m, 7H ), 7.82-7.89 -m, 3H) 80-5) (S) -1 - (1H-lmidazole -4-i.2) methyl -3- [N- (1-methoxy-carbonyl-3 -methyl thio) propyl] carbamoyl- - - (naphthalen-1-yl) -1H-pyrrole 200 mg (0.60 mmol) of the compound prepared in Example 80-4) were dissolved in 2 ml of dimethylformamide and then they added there 150 mg (0.78 mmol) of EDC and 105 mg (0.78 mmol) of HOBT. The resulting mixture was stirred at 0 ° C for 5 minutes. To the reaction solution was added 120 mg (0.60 mmol) of L-methionine methyl ester, which was then stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and then 10 ml of a saturated NaHCO 3 solution was added to the residue. The resulting solution was extracted with ethyl acetate, washed with an aqueous solution of sodium chloride and water, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to column chromatography (eluent: dichloromethane / methanol = 20/1, v / v) to obtain 104 mg (0.225 mmol, 37% yield) of the title compound. XH NMR (CDC13) d 1.21 (m, HH), 1.55 (m, 3H), 1.80 (s, 3H), 3.42 (s, 3H), 4.43 (m, HH) , 5.05 (s, 2H), 5.60 (d, ÍH), 6.71 (s, ÍH), 6.95 (s, 1H), 7.21-7.45 (m, 7H), 7.75-7.87 (m, 3H) FAB MS: 463 (M + 1) Example 81: Synthesis of (S) -3- [N- (l-hydroxysarbonyl-3-methylthio) propyl] carbamoyl-1- (lH-imidazol-4-yl) methyl-4- (naf to en-1-yl) -lH-pyrrole (81) 70 mg (0.15 mmol) of the compound prepared in Example 80-5) were dissolved in 2 ml of a mixture of tetrahydrofuran / methanol / water solvents (3/2/1, v / v / v). There, 10 mg (0.18 mmol) of lithium hydroxide were added and the mixture was stirred at room temperature for 4 hours. The solvent was removed under reduced pressure to obtain 68 mg (0.15 mmol, yield 99.7%) of the lithium salt of the title compound. 1H NMR (CD3OD + CDC13) d 1.25 (m, HH), 1.49 (m, 3H), 1.85 (s, 3H), 4.41 (m, HH), 5.11 (s, 2H), 5.58 (d, ÍH), 6.70 (s, ÍH), 6.89 (s, ÍH), 7.15-7.38 (m, 7H), 7.76-7.81 (m, 3H) FAB MS: 449 (M + 1) EXAMPLES 82 to 98: The compounds represented in the following Tables 4-1 and 4-2 were obtained according to the similar procedure of Example 80.

TABLE 4-2 Example 99: Synthesis of 1- (1-methyl-lH-imidazol-5-yl) methyl-3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -5 lH-pyrrole (99) The compound prepared in Example 85 was introduced • a trifly protecting group according to the same procedure as that used in Preparation 28-1) and then the title compound was obtained in a 55% yield by applying the procedures employed in Preparations 29-2) and 29-3), using methyl iodide. 1 H NMR (CDC13) d 2.80-3.45 (m, 8H), 3.58 (s, 3H), 5.19 (s, 2H), 6.75 (d, ÍH), 7.18 ( d, ÍH), 7.21 (s; ÍH), 7.35 (d, ÍH), 7.40-7.50 (m, 3H), 7.72 (d, ÍH), 8.03 (d , HH) 15 FAB MS: 401 (M + 1) • Example 100: Synthesis of (S) -1- [1- (4-sianobenzyl) -1H-imidazol-5-yl] methyl-3- [N- ( 1-methoxycarbonyl-3-methylthio) propyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (100) 20 100-1) 1 - [1- (4-Cyanobenzyl) -lH-imidazole-5- ilmethyl] -3-hydroxycarbonyl-4- (naphthalen-1-yl) -lH-pyrrole The title compound was obtained in 75% yield from the compounds prepared in Example 80-2) and in Preparation 29-5) sequentially applying the procedures of Example 73 and Example 80-4). • 1R NMR (CDC13 + CD3OD) d 5.02 (s, 2H), 5.10 (s, 2H), 6.76 (s, ÍH), 7.07 '(m, 2H), 7.25- 7.82 (m, 12H) 100-2) (S) -1 - [1 - (4-Cyanobenzyl) -lH-imidazol-5-yl] methyl -3- [N- (1 -me tox i -carbon i 1 -3-methyl thio) propyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole The title compound was obtained in a yield of 35% according to the same procedure as that used in the Example 80-5), with the exception that the compound was used • prepared in Example 100-1). * H NMR (CDC13) d 1.85 (s, 3H), 2.04 (m, ÍH), 2.13 (m, ÍH), 2.42 (t, 2H), 3.61 (s, 3H ), 4.83 (m, ÍH), 5.02 (s, 2H), 5.11 (s, 2H), 6.63 (s, ÍH), 7.01 (d, 2H), 7.13 (d, ÍH), 7.22-7.43 (m, 7H), 7.65 -7.92 (m, 4H) FAB MS: 578 (M + 1) Example 101: Synthesis of (S) -1- [1- (4-cyanobenzyl) -1H-imidazol-5-yl] methyl-3 [N- (l-hydroxycarbonyl-3-methylthio) Propyl] carbamoyl-4- (naphthalen-1-yl) -IH-pyrrole (101) The lithium salt of the title compound was obtained in a yield of 96% according to a procedure similar to that of Example 81, of the compound prepared in Example 100-2). 25 1 NM NMR (CDC13 + CD3OD) d 1.82 (s, 3H), 2.00 (m, HH), 2, ll (m, HH), 2.36 (t, 2H), 4.82 (m , ÍH), 4.89 (s, 2H), 5.02 (s, 2H), 6.49 (s, ÍH), 6.88 (d, 2H), 7.11 (d, 1H), 7 , 17-7.32 (m, 7H), 7.62-7.83 (m, 4H) FAB MS: 564 (M + l) EXAMPLES 102 and 103: The compounds represented in the following Table 5 were obtained in accordance with a procedure similar to that of Examples 100 and 101.

TABLE 5 Examples 104 and 105: The compounds represented in the following Table 6 were obtained according to a procedure similar to that of Example 101.

Example 106: Synthesis of 1- [2- (1H-imidazol-1-yl) ethyl] -3- (mor-olin-4-yl) carbonyl-4- (nalen-1-yl) -lH-pyrrole (106 ) 1 06-1) 2- (IH-Imidazol-1-yl) ethyl p-tosylate 0.24 g (2.41 mmol) of 2- (1H-imidazol-1-yl) ethanol and 0.55 were dissolved. g (2.88 mmol) of chloride, of tosyl in 20 ml of dichloromethane. There 0.67 ml of triethylamine was added thereto at 0 ° C and the mixture was stirred at room temperature for 4 hours. The organic solvent was removed under reduced pressure. The residue was dissolved in 10 ml of ethyl acetate, washed sequentially with a solution of IN hydrochloric acid, a saturated sodium bicarbonate solution and a saturated sodium chloride solution.; dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to column chromatography (eluent: dichloromethane / methanol = 20/1, v / v) to obtain 0.30 g (1.13 mmol, 47% yield) of the title compound. 1H NMR (CDC13) d 2.42 (s, 3H), 4.17-4.28 (m, 4H), 6.88 (s, ÍH), 6.99 (s, 1H), 7.29 ( d, 2H), 7.45 (s, ÍH), 7.64 (d, 2H) 106-2) 3-Hydroxycarbonyl -4- (naphthalen-1-yl) -lH-pyrrole The title compound was obtained with a yield of 80% by hydrolyzing the compound prepared in Example 80-2) according to the same procedure as that used in Example 80-4). XH NMR (CDC13 + CD30D) d 7.12 (m, 3H), 7.20-7.31 (m, 3H), 7.50 (d, ÍH), 7.68 (d, ÍH), 7, 76 (d, ÍH) 106-3) 3- (Morpholin-4-yl) carbonyl -4 - (naphthalen-1 -yl) -IH-pyrrole The title compound was obtained in a yield of 99% according to same procedure as that used in Example 80-5), from the compound prepared in Example 106-2) and msrfolino. XH NMR (CDC13) d 2.68-3.62 (brs, 8H), 6.88 (s, ÍH), 7.20 (s, ÍH), 7.30-7.62 (m, 4H), 7.78 (d, ÍH), 7.85 (d, ÍH), 8.08 (d, ÍH), 10.34 (s, 1H) 106-4) l - [2- (IH-Imidazole -l -yl) ethyl] -3- (morpholin-4-yl) carbonyl -4- (naphthalen-1-yl) -lH-pyrrole The title compound was obtained in a yield of 51% by reacting the compound prepared in the Example 106-1) with the compound prepared in Example 106-3), according to the same procedure as that used in Example 44-3). 1H NMR (CDC13) d 2.20-3.72 (brs, 12H), 7.20 (s, ÍH), 7.40-7.55 (m, 8H), 7.82 (d, ÍH), 7.88 (d, 1H), 8.05 (d, 1H) FAB MS: 401 (M + 1) Example 107: Synthesis of (S) -1- [3- (1H-imidazol-4-yl) propyl ] -3- [N- (1-methoxycarbonyl-3-methylthio) propyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (107) 107-1) 3-Ethoxycarbonyl-4- (naphthalen-1) -yl) -l- [3- (1-Trityl-1H-imidazol-4-yl) allyl] -lH-pyrrole The title compound was obtained in a yield of 85% by reacting the compound prepared in Example 80- 2) with the compound prepared in Preparation 30-4) according to the same procedure as that used in Example 44-3). XH NMR (CDCl 3) d 0.82 (t, 3H), 3.95 (q, 2H), 4.67 (s, 2H), 6.23 (d, ÍH), 6.47 (m, ÍH) , 6.63 (s, 1H), 7.02 (s, ÍH), 7.25-7.81 (m, 24H) 107-2) 3-Ethoxycarbonyl -4- (naphthalen-1 -yl) -l - [3- (1-Trityl-1H-imidazol-4-yl) propyl] -lH-pyrrole 300 mg (0.49 mmol) of the compound prepared in Example 107-1) were dissolved in 2 ml of methanol. A catalytic amount of Pd / C was added thereto and the mixture was stirred for 1 hour under a nitrogen atmosphere. The mixture was filtered to remove the catalyst and the solvent therein was removed under reduced pressure. The residue was subjected to column chromatography (eluent: dichloromethane / methanol = 98/2, v / v) to obtain 246 mg (0.40 mmol, 82% yield) of the title compound. 1 H NMR (CDCl 3) δ 0.92 (t, 3 H), 2.22 (m, 2 H), 2.73 (t, 2 H), 4.01 (m, 4 H), 6.70 (s, 1 H) , 6.82 (s, ÍH), 7.32-7.73 (m, 21H), 7.91 (m, 3H) 107-3) (S) -l- [3- (lH-Imidazole-4 -yl) propyl] -3- [N- (1-methoxycarbonyl-3-methylthio) propyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole The compound prepared in Example 107-2) was treated with according to the procedures of Examples 44-4) and 80-4) to remove the trityl group and hydrolyze. Then, the product obtained in this way. was reacted with (L) -methionine methyl ester, according to the same procedure as that used in Example 80-5), to obtain the title compound, with a 29% Yield. X H NMR (CDCl 3) d 1.65 (m, 2 H), 1.90 (s, 3 H), 2.12 (m, 2 H), 2.31 (m, 2 H), 2.73 (m, 2 H) , 3.54 (s, 3H), 4.02 (m, 2H), 4.56 (m, ÍH), 5.77 (d, ÍH), 6.72 (s, ÍH), 6.90 ( s, 1H), 7.42-7.67 (m, 7H), 7.82-8.01 (m, 5H) FAB MS: 491 (M + 1) Example 108: Synthesis of (S) -3- [N- (l-hydroxycarbonyl-3-methylthio) propyl] carbamoyl-1- [3- (lH-imidazol-4-yl) propyl] -4- (naphthalen-1-yl) -lH-pyrrole (108) compound of the title was obtained in a 95% yield according to the same procedure as that used in Example 81, except that the compound prepared in Example 107-3) was used. 1 NM NMR (CDCl 3) δ 1.57 (m, 2 H), 1.88 (s, 3 H), 2.08 (m, 2 H), 2.29 (m, 2 H), 2.77 (m, 2 H) , 4.12 (m, 2H), 4.49 (m, 1H), 5.69 (d, ÍH), 6.77 (s, ÍH), 6.92 (s, ÍH), 7.34- 7.58 (m, 7H), 7.80-7.89 (m, 5H) FAB MS: 477 (M + 1) Example 109: Synthesis of 1- [3- (1H-imidazol-4-yl) propyl ] -3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (109) The title compound was obtained in 42% yield according to the same procedure that would be used in Example 107-3), with the exception that morpholino was used with the compound prepared in Example 107-2). 1R NMR (CDC13) d 2.16 (m, 2H), 2.35 (brs, 2H), 2.63 (m, 2H), 2.80-3.50 (brs, 6H), 3.54 ( s, 3H), 3.96 (m, 2H), 6.74 (d, ÍH), 6.76 (s, ÍH), 7.07 (s, ÍH), 7.33 (t, ÍH), 7.36-7.50 (m, 4H), 7.76 (d, 1H), 7.84 (d, 1H), 8.08 (d, 1H) FAB MS: 415 (M + 1) Example 110 : Synthesis of 1- [1- (4-cyanobenzyl) -IH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4 - (naphthalen-1-yl) -lH-pyrrole (110) 110-1) 3- [N- (2-Methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole 100 mg (0.42 mmol) of the compound prepared in the Example 106-2) and 38 mg (0.4 mmol) of N- (2-methoxyethyl) -N-methylamine were reacted according to a procedure similar to that of Example 80-5), to obtain 110 mg (0.35 mmol, yield 85%) of the title compound. ? NMR (CDCl 3) d 2.21 (s, 3H), 2.64 (brs, ÍH), 2.75 (brs, ÍH), 3.02 (s, 3H), 3.13 (brs, 1H), 3.32 (brs, ÍH), 6.72 (s, HH), 7.05 (m, 2H), 7.21 (m, 2H), 7.54 (m, 1H), 7.78 (m , 2H), 8, 04 (d, ÍH), 8, 78 (brs, 1H) 110-2) 1 - [1 - (4-Cyanobenzyl) -lH-imidazol-5-yl] methyl- 3- [N - (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pi rrol 98 mg (0.32 mmol) of the compound prepared in Example 110-1) and 85 mg (0 , 32 mmol) of the compound prepared in Preparation 29-5) were reacted according to a procedure similar to that of Example 44-3), to obtain 115 mg (0.23 mmol, 72% yield) of the title compound. 1ti NMR (CDC13) d 2.41 (s, 3H), 2.75 (brs, 2H), 3.07 (s, 3H), 3.17 (brs, ÍH), 3.32 (brs, -ÍH ), 4.91 (s, 2H), 5.11 (s, 2H), 6.71 (s, 1H), 7.05 (s, ÍH), 7.17 (d, ÍH), 7.40 -7.68 (m, 9H), 7.78 (d, 1H), 7.88 (d, 1H), 8.06 (d, ÍH) FAB MS: 504 (M + l) Example 111: Synthesis of 1- [1- (4-bromobenzyl) -1H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH- pyrrole (111) 105 mg (0.29 mmol) of the compound prepared in Example 110-1) and 78 mg (0.29 mmol) of the compound prepared in Preparation 32-2) were reacted according to a similar procedure to the employee in Example 44-3), to obtain 121 mg (0.21 mmol, 75% yield) of the title compound. XH NMR (CDC13) d 2, 37 (s, 3H), 2.72 (brs, 2H), 3.04 (s, 3H), 3.15 (brs, ÍH), 3.31 (brs, ÍH), 4.95 (s, 2H), 5.10 (s, 2H), 6.67 (s, ÍH), 7, ll (s, ÍH), 7.23-7.65 (m, 10H), 7.81 (d, ÍH) ), 7.89 (d, ÍH), 8.02 (d, ÍH) FAB MS: 557 (M + l) Example 112: Synthesis of 1- [1- (4-bromobenzyl) -1H-imidazole-5- il] methyl-3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (112) 100 mg (0.33 mmol) of the compound prepared in Example 106-3) and 105 mg (0.33 mmol) of the compound prepared in Preparation 32-2) were reacted according to a procedure similar to that employed in Example 44-3) to obtain 130 mg (0.23 mmol, 71% yield) of the title compound. XH NMR (CDC13) d 2.04 (brs, 2H), 2.25 (brs, ÍH), 3.03 (brs, 5H), 4.93 (s, 2H), 5.07 (s, 2H) , 6.62 (s, ÍH), 7.10 (m, 3H), 7.29 (m, 2H), 7.41 (m, 3H), 7.60 (m, 3H), 7.81 ( d, 1H), 7.89 (d, ÍH), 8.01 (d, ÍH) FAB MS: 555 (M + l) Example 113: Synthesis of 1- [1- (4-cyanobenzyl) -IH-imidazole -5-yl] methyl-3- (morpholin-4-yl) thiocarbonyl-4- (naphthalen-1-yl) -lH-pyrrole (113) 20 mg (0.04 mmol) of the compound prepared in Example 104 and 18 mg of 2,4-bis (phenylthio) -1,3-dithia-2,4-diphosphatan -2,4-disulfide was dissolved in 1 ml of tetrahydrofuran and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added 2 ml of a saturated sodium bicarbonate solution. The resulting mixture was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The organic solvent was removed under reduced pressure and the residue was subjected to column chromatography (eluent: dichloromethane / methanol = 9/1, v / v) to obtain 9 mg (0.017 mmol, 43% yield) of the title compound.

XH NMR (CDCl 3) d 1.88 (brs, 2H), 2.64 (brs, 6H), 4.86 (s, 2H), 5.01 (s, 2H), 6.67 (s, ÍH) , 7.14 (m, 3H), 7.26-7.58 (m, 8H), 7.81 (m, 2H), 8.03 (d, ÍH) • FAB MS: 518 (M + l) Example 114: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- (1-methyl-1H-imidazol-5-yl) methyl-4- (naf to en-1-yl) ) -lH- pyrrole (114) 114-1) 4- (Naphthalen-1-yl) -lH-pyrrole-3-carboxylic acid 2.64 g (10 mmol) of the compound prepared in Example 10 80-2) dissolved in 50 ml of 50% ethanol and therein was added 2.24 g (40 mmol) of potassium hydroxide. The The reaction mixture was refluxed for 7 hours, cooled to room temperature, adjusted to pH 4-5, extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain 1.62 g (8.1 mmol, 81% yield) of the title compound. The product obtained in this way was used in the next reaction without purification. ti NMR (CDC13) d 6.60 (s, ÍH), 7.32-7.49 (m, 5H), 7.54 (s, 20 ÍH), 7.84 (m, 2H), 9.92 (s, ÍH) FAB (M + H): 236 114-2) 3- [N- (2-Methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole 234 mg ( 1 mmol) of the compound prepared in Example 114-1) were dissolved in 2 ml of dimethylformamide and then 230 mg (1.2 mmol) of EDC, 101 mg (1 mmol) of triethylamine and 162 mg (1.2 mmol) of HOBT were added thereto. The resulting mixture was stirred at 0 ° C, for 5 minutes. To the reaction solution was added 124 mg (1 mmol) of N- (2-methoxyethyl) -N-methylamine hydrochloride, which was subsequently stirred at room temperature, for 5 hours. The solvent is • removed under reduced pressure and then 10 5 ml of a saturated potassium carbonate solution were added to the residue. The resulting solution was extracted with 20 ml of ethyl acetate, washed with 10 ml of an aqueous solution of IN hydrochloric acid, washed with an aqueous solution of sodium chloride and water. It was dried in anhydrous sodium sulfate and concentrated to obtain 246 mg (0.8 mmol) of the title compound. • XH NMR (CDC13) d 2.46 (s, 2H), 2.80-3.40 (m, 7H), 3.40 (s, ÍH), 6.80 (s, ÍH), 7.00 (s, ÍH), 7.42 (m, 4H), 7.73 (d, ÍH), 7.81 (d, ÍH), 8.17 (d, ÍH), 10.66 (s, ÍH) 15 FAB (M + H): 309 114-3) 1 - (1-methyl-1H-imidazol-5-yl) methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl -4- ( Naphthalen-1-yl) -IH-pyrrole 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There he added 264 mg (6.6 mmol) of sodium hydride (60%) at 0 ° C and then, the mixture was stirred for 5 minutes. To the mixture was added 367 mg (2.2 mmol) of 5-chloromethyl-1-methylimidazole hydrochloride and the whole mixture was stirred at room temperature for 5 hours. The solvent was removed by distillation under reduced pressure and 10 ml of water was added to the residue. The mixture was subsequently extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol 90/10, v / v ) to obtain 644 mg (Yield 80%) of the title compound. XH NMR (CDC13) d 2.42 (s, 2H), 2.71 (m, ÍH), 3.10 (brs, 6H), 3.30 (brs, ÍH), 3.50 (s, 3H) , 5.09 (s, 2H), 6.70 (s, ÍH), 7.05 (s, ÍH), 7.15 (s, ÍH), 7.30-7.49 (m, 4H), 7.72 (d, ÍH), 7.84 (d, 2H), 8.08 (d, ÍH) FAB (M + H): 403 Example 115: Synthesis of 1- (l-isobutyl-lH-imidazole- 5-yl) methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (115) 618 mg (2.0 mmol) of the compound prepared in the example 114-2) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 459 mg were incorporated (2.2 mmol) of the compound prepared in Preparation 33-2) was added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was removed by distillation, under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v), to obtain 667 mg (Yield 75%) of the title compound. 1 H NMR (CDCl 3) d 0.90 (d, 6H), 1.75 (m, HH), 2.41 (brs, 2H), 2.72 (brs, HH), 3.01 (brs, 6H) , 3.32 (brs, ÍH), 3.62 (d, 2H), 5.13 (s, 2H), 6.72 (s, ÍH), 7.09 (s, ÍH), 7.19 ( s, ÍH), 7.30-7.49 (m, 4H), 7.78 (d, HH), 7.84 (d, 2H), 8.08 d, HH) FAB (M + H): 445 'Example 116: Synthesis of 1- (1-Cyclohexylmethyl-1H-imidazol-5-yl) methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (116) 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 647 mg were incorporated (2.2 mmol) of the compound prepared in Preparation 34-2) was added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 726 mg (Yield 75%) of the title compound. 1H NMR (CDC13) d 0.87 (m, 2H), 1.12 (m, 3H), 1.30 (brs, 1H), 1.40-1.80 (m, 5H), 2.41 ( brs, 2H), 2.72 (brs, ÍH), 3.01 (brs, 6H), 3.32 (brs, ÍH), 3.63 (d, 2H), 5.09 (s, 2H), 6.72 (s, ÍH), 7.09 (s, ÍH), 7.19 (s, ÍH), 7.25 (s, ÍH), 7.30-7.49 (m, 3H), 7 , 78 (d, 1H), 7.83 (d, 2H), 8.08 (d, ÍH) FAB (M + H): 485 Example 117: Synthesis of 3- [N- (2-methoxyethyl) -N -methyl] carbamoyl-4- (naphthalen-1-yl) -1- (l-pentyl-lH-imidazol-5-yl) methyl-lH-pyrrole (117) 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There he • incorporated 264 mg (6.6 mmol) of sodium hydride (60%) at 50 ° C and the mixture was stirred for 5 minutes. 429 mg (2.2 mmol) of the compound prepared in Preparation 35-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was removed by distillation. at reduced pressure and 10 ml of water were added to the residue. The resulting mixture was extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, • concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v) to obtain 714 mg (Yield 78%) of the title. XH NMR (CDC13) d 0.90 (t, 3H), 1.08 (brs, 2H), 1.30 (m, 2H), 1.45 (m, 2H), 2.41 (brs, 2H) , 2.72 (brs, ÍH), 3.01 (brs, 6H), 3.32 (brs, ÍH), 3.63 (t, 2H), 5.09 (s, 2H), 6.72 ( s, ÍH), 7.09 (s, ÍH), 7.19 (s, ÍH), 7.25 (s, 1H), 7, 30-7, 49 - (m, 3H), 7.78 (d, ÍH), 7.83 (d, 2H), 8.08 (d, ÍH) FAB (M + H): 459 Example 118: Synthesis of 3- [N- (2 -methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -1- (l-octyl-lH-imidazol-5-yl) methyl-lH-pyrrole (118) 25 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 508 mg (2.2 mmol) of the compound prepared in Preparation 36-2) was added to the mixture, which was then stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 760 mg (Yield 76%) of the title compound. XH NMR (CDC13) d 0.87 (t, 3H), 1.17 (brs, 2H), 1.30 (brs, 10H), 1.44 (m, 2H), 2.41 (brs, 2H), 2.72 (brs, 1H), 3 , 01 (brs, 6H), 3.32 (brs, 1H), 3.62 (t, 2H), 5.09 (s, 2H), 6.72 (s, 1H), 7.09 (s, ÍH), 7,19 (s, ÍH), 7,25 (s, ÍH), 7,30-7,49 (m, 3H), 7,78 (d, ÍH), 7,83 (d, 2H) ), 8.08 (d, ÍH) FAB (M + H): 501 Example 119: Synthesis of 1- (l-decyl-lH-imidazol-5-yl) methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (nalen-1-yl) -1H-pyrrole (119) 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 567 mg (2.2 mmol) of the compound prepared in Preparation 37-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 667 mg (Yield 75%) of the compound of the "title: XH NMR (CDC13) d 0.87 (t, 3H), 1.1" (brs, 2H), 1.30 (brs, 14H) , 1.44 (m, 2H), 2.41 (brs, 2H), 2.72 (brs, ÍH), 3.01 (brs, 6H), 3.32 (brs, ÍH), 3.62 ( t, SH), 5.09 (s, 2H), 6.72 (s, ÍH), 7.09 (s, ÍH), 7.19 (s, ÍH), ~, 25 (s, ÍH), 7.30-7.49 (m, 3H), 7.78 (d, HH), 7.83 (d, 2H), 8.08 (d, HH) -FAB (M + H): 529 Example 120 : Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- (3-methylbutyl) -lH-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -lH-pyrrole (120) 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dir-ethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 429 mg (2.2 mmol) of the compound prepared in Preparation 38-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v ) to obtain 667 mg (Yield 75%) of the title compound. XH NMR (CDCl 3) d 0.91 (d, 6H), 1.31 (q, 2H), 1.67 (m, HH), 2.41 (brs, 2H), 2.72 (brs, HH) , 3.01 (brs, 6H), 3.32 (brs, ÍH), 3.62 (t, 2H), 5.09 (s, 2H), 6.72 (s, ÍH), 7.09 ( s, ÍH), 7.19 (s, ÍH), 7.25 (s, ÍH), 7.30-7.49 (m, 3H), 7.78 (d, ÍH), 7.83 (d , 2H), 8.08 (d, ÍH) FAB (M + H): 459 Example 121: Synthesis of 1- [1- (2-methoxyethyl) -lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH- pyrrole (121) 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 429 mg (2.2 mmol) of the compound prepared in Preparation 39-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 667 mg (Yield 75%) of the title compound. XH NMR (CDC13) d 2.41 (brs, 2H), 2.72 (brs, 1H), 3.01 (brs, 6H), 3.32 (brs, ÍH), 3.37 (s, 3H) , 3.45 (t, 2H), 3.63 (t, 2H), 5.09 (s, 2H), 6.72 (s, ÍH), 7.09 (s, ÍH), 7.19 ( s, ÍH), 7.25 (s, ÍH), 7.30-7.49 (m, 3H), 7.78 (d, 1H), 7.83 (d, 2H), 8.08 (d , HH) FAB (M + H): 447 Example 122: Synthesis of 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- (3-methoxypropyl) -lH-imidazole-5- il] methyl-4- (naphthalen-1-yl) -lH-pyrrole (122) 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 459 mg (2.2 mmol) of the compound prepared in Preparation 40-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was removed by distillation under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 683 mg (Yield 70%) of the title compound. 1H NMR (CDC13) d 1.71 (m, 2H), 2.41 (brs, 2H), 2.72 (brs, ÍH), 3.01 (brs, 6H), 3.31 (s, 3H) , 3.32 (brs, 1H), 3.48 (t, 2H), 3.63 (t, 2H), 5.09 (s, 2H), 6.72 (s, ÍH), 7.09 ( s, ÍH), 7.19 (s, ÍH), 7.25 (s, ÍH), 7.30-7.49 (m, 3H), 7.78 (d, ÍH), 7.83 (d , 2H), 8.08 (d, ÍH) FAB (M + H): 461 Example 123: Synthesis of 1- [1- (3-ethoxypropyl) -lH-imidazol-5-yl] methyl-3- [N - (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (123) 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 459 mg (2.2 mmol) of the compound prepared in Preparation 41-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 20 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 712 mg (Yield 71%) of the title compound. XH NMR (CDC13) d 1.20 (t, 3H), 1.70 (m, 2H), 2.41 (brs, 2H), 2.72 (brs, ÍH), 3.01 (brs, 6H) , 3.32 (brs, ÍH), 3.50 (m, 4H), 3.63 (t, 2H), 5.09 (s, 2H), 6.72 (s, ÍH), 7.09 ( s, 1H), 7.19 (s, ÍH), 7.25 (s, ÍH), 7.30-7.49 (m, 3H), 7.78 (d, 1H), 7.83 (d , 2H), 8.08 (d, ÍH) FAB (M + H): 475 Example 124: Synthesis of 1- [1- (3-isopropoxypropyl) -lH-imidazol-5-yl] methyl-3- [N - (2-methoxyethyl) -N-methyl] carbamoyl-4- (naph alen-1-yl) -lH-pyrrole (124) 618 mg (2.0 mmol) of the compound prepared in Example 114-2) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the mixture was stirred for 5 minutes. 459 mg (2.2 mmol) of the compound prepared in Preparation 42-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 20 • ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography (eluent: dichloromethane / methanol = 90/10, v / v) to obtain 751 mg (yield 73%) of the title compound. XH NMR (CDC13) d 1.16 (d, 6H), 1.70 (m, 2H), 2.41 (brs, 2H), 2.72 (brs, ÍH), 3.01 (brs, 6H), 3.32 (brs, ÍH), 3.45-3.55 (m, 3H), 3.63 (t, 2H), 5.09 (s, 2H), 6.72 (s, ÍH), 7.09 (s, ÍH), 7.19 (s, ÍH), 7.25 (s, ÍH), 7.30-7.49 (m, 3H), 7.78 (d, ÍH), 7.83 (d, 2H), 8.08 (d, HH) FAB (M + H): 489 Example 125: Synthesis of 1- [1- (4-bromobenzyl) - 15 lH-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (nalen-1-yl) -lH-pyrrole (125) 125-1) 3- [4- Methylpiperazin-l -yl] carbonyl- - (naphthalen-1-yl) -IH-pyrrole The title compound was obtained in a yield of 20 90% according to the same procedure as that used in • Example 80-5), from the compound prepared in Example 106-2) and 4-methylpiperazine. 2 H NMR (CDCl 3) d 1.15 (br, 2 H), 1.87 (br, 2 H), 1.92 (s, 3 H), 2.96 (br, 2 H), 3.41 (br, 2 H) , 6.83 (s, ÍH), 7.09 (s, 25 ÍH), 7.36-7.42 (m, 4H), 7.73 (d, ÍH), 7.75 (d, ÍH) , 8.10 (d, ÍH), 10.52 (s, ÍH) FAB (M + H): 320 125-2) 1 - [1 - (4-Bromobenzyl) -lH-imidazol-5-yl] methyl 3- [4-methylpiperazin-1 -yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole 64 mg (0.2 mmol) of the compound prepared in Example 125-1) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 66 mg (0.22 mmol) of the compound prepared in Preparation 32-2) were added to the mixture, which was subsequently stirred at room temperature, for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 91. mg (Yield 80%) of the title compound. H NMR (CDC13) d 1.15 (br, 2H), 1.77 (br, 2H), 1.86 (s, 3H), 2.82 (br, 2H), 3.28 (br, 2H) , 4.87 (s, 2H), 3.88 (s, 2H), 6.55 (s, ÍH), 6.79 (d, 2H), 6.97 (s, ÍH), 7.16 (s, s, 1H), 7.36 (d, ÍH), 7.36-7.39 (m, 5H), 7.50 (s, ÍH), 7.71 (d, 1H), 7.79 (d , HH), 7.93 (d, HH) FAB (M + H): 568 Example 126: Synthesis of 1- [1- (4-chlorobenzyl) -lH-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (nalen-1-yl) -lH-pyrrole (126) 64 mg (0.2 mmol) of the compound prepared in Example 125-1) were dissolved ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 55 mg (0.22 mmol) of the 1- (4-chlorobenzyl) -5-chloromethylimidazole hydrochloride prepared according to a procedure similar to that used in Preparation 32 were added to the mixture, which was subsequently stirred at room temperature, for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 77 mg (Yield 57%) of the title compound. XH NMR (CDC13) d 1.15 (br, 2H), 1.77 (br, 2H), 1.86 (s, 3H), 2.82 (br, 2H), 3.28 (br, 2H), 4.92 (s, 2H), 4.95 (s, 2H), 6.60 (s, 1H), 6.91 (d, 2H), 6.01 (s, ÍH), 7.22 (s, 1H), 7.26-7.36 (m, 3H) ), 7.36-7.48 (m, 2H), 7.56 (s, ÍH), 7.77 (d, ÍH), 7.82 (d, 1H), 7.93 (d, ÍH) FAB (M + H): 524 Example 127: Synthesis of 1- [1- (4-fluobenzyl) -lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl -4- (naphthalen-1-yl) -lH-pyrrole (127) 62 mg (0.2 mmol) of the compound prepared in Example 114-2) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 51 mg (0.22 mmol) of the 1- (4-fluobenzyl) -5-chloromethylimidazole hydrochloride prepared according to a procedure similar to that employed in Preparation 32 were added to the mixture, which was subsequently stirred at room temperature during 5 hours.

The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 77 mg (Yield 80%) of the title compound. XH NMR (CDC13) d 2.12 (br, 3H), 2.72 (br, ÍH), 3.00-3.20 (m, 5H), 3.32 (s, ÍH), 4.97 ( s, 2H), 3.98 (s, 2H), 6.64 (s, ÍH), 6.95-7.10 (m, 5H), 7.21 (s, ÍH), 7.33 (m , ÍH), 7.40-7.51 (m, 3H), 7.66 (s, HH), 7.74 (d, 1H), -7.81 (d, HH), 8.08 (d , HH) FAB (M + H): 497 Example 128: Synthesis of 1- [1- (4-fluobenzyl) -1H-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl- 4- (na talen-1-yl) -lH-pyrrole (128) 64 mg (0.2 mmol) of the compound prepared in Example 125-1) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 51 mg (0.22 mmol) of the 1- (4-fluobenzyl) -5-chloromethylimidazole hydrochloride prepared according to a procedure similar to that used in Preparation 32 were added to the mixture, which was subsequently stirred at room temperature during 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / l). v) to obtain 79 mg (Yield 80%) of the title compound. 1H NMR (CDC13) d 1.15 (br, 2H), 1.77 (br, 2H), 1.86 (s, 3H), 2.82 (br, 2H), 3.28 (br, 2H) , 4.92 (s, 2H), 4.97 (s, 2H), 6.60 (s, 1H), 6.93 (d, 2H), 6.01 (s, ÍH), 7.22 (s, ÍH), 7.25-7.36 (m, 3H), 7.36-7.47 (m, 2H), 7.57 (s, ÍH), 7.78 (d, 1H), 7.82 (d, ÍH), 7.93 (d, ÍH) FAB (M + H) 508 Preparation 43: Synthesis of 5-chloromethyl-1- (4-methoxybenzyl) imidazole hydrochloride 43-1 ) 5-Hydroxymethyl-1 - (4-methoxybenzyl) imidazole The title compound was obtained in 30% yield according to the same procedure as that used in Preparation 31-1) using dihydroxyacetone and 4-methoxybenzylamine hydrochloride as starting materials. 1 NMR (CDC13 + CD3OD) d 3.75 (s, 3H), 4.50 (s, 2H), 5.15 (s, 2H), 6.86 (m, 3H), 7.08 (d, 2H), 7.42 (s, 1H) FAB (M + H): 219 43-2) 5-Chloromethyl-1 - (4-methoxybenzyl) imidazole hydrochloride The title compound was obtained with a yield of 95% according to the same procedure as that used in Preparation 28-2), with the exception that the compound that was prepared in Preparation 43-1) was used as a starting material. Preparation 44: Synthesis of 5-chloromethyl-1- (3-chlorobenzyl) -imidazole 44-1) 5-Hydroxymethyl-1 - (3-chlorobenzyl) imidazole hydrochloride The title compound was obtained in 60% yield according to with the same procedure as that used in Preparation 31-1) using dihydroxyacetone and 3-chlorobenzylamine hydrochloride as starting materials. XH NMR (CDC13 + CD3OD) d 3.81 (s, 3H), 4.47 (s, 2H), 5.25 (s, 2H), 6.99 (s, ÍH), 7.05 (m, ÍH), 7.14 (s, ÍH), 7.30 (d, 2H), 7.61 (s, ÍH) FAB (M + H): 239.5 44-2) 5-Chloromethyl-Hydrochloride - (3-Chlorobenzyl) imidazole The title compound was obtained in a yield of 92% according to the same procedure as that used in Preparation 28-2), with the exception that the compound to be prepared in Preparation 44 -1) was used as a starting material. Preparation 45: Synthesis of 5-chloromethyl-1- (2-chlorobenzyl) imidazole 45-1 hydrochloride 5-Hydroxymethyl-1 - (2-chlorobenzyl) imidazole The title compound was obtained in 60% yield according to the same procedure as that used in Preparation 31-1), using dihydroxyacetone and 2-chlorobenzylamine hydrochloride as starting materials.

XH NMR (CDC13) d 3.24 (s, 2H), 4.44 (s, 2H), 5.26 (s, 2H), 6.78 (d, 1H), 6.90 (s, ÍH) , 7.15 (m, ÍH), 7.21 (m, ÍH), 7.34 (d, ÍH), 7.38 (s, ÍH) FAB (M + H): 239.5 45-2) Chlorhydrate to 5-romet il-1 - (2-chlorobenzyl) imidazole The title compound was obtained in 92% yield according to the same procedure as that used in Preparation 28-2), with the exception of that the compound to be prepared in Preparation 45-1) was used as a starting material. Preparation 46: Synthesis of 5-chloromethyl-1- (2-fluobenzyl) imidazole 46-1) 5-Hydroxymethyl-1 - (2-p-luobenzyl) imidazole hydrochloride The title compound was obtained in a 71% yield according to with the same procedure as that used in Preparation 31-1) using dihydroxyacetone and 2-fluobenzylamine hydrochloride as starting materials. 1 NMR (CDC13) d 3-, 25 (s, 2H), 4.45 (s, 2H), 5.27 (s, 2H), 6.79 (d, 1H), 7.17 (m, 1H) ), 7.26 (m, HH), 7.35 (d, HH), 7.38 (s, HH) FAB (M + H): 223 46-2) 5-Chloromethyl-1 - (2-chlorohydrate) -f luobenzyl) imidazole The title compound was obtained with a yield of 93% according to the same procedure as that used in Preparation 28-2), with the exception that the compound that was prepared in Preparation 46-1) was used as a starting material. Preparation 47: Synthesis of 5-chloromethyl-1- (4-methylbenzyl) imidazole 47-1) 5-Hydroxymethyl-1- (4-methylbenzyl) imidazole hydrochloride The title compound was obtained in 65% yield according to the same procedure as that used in Preparation 31-1), using dihydroxyacetone and 4-methylbenzylamine hydrochloride as starting materials. 1H NMR (CDC13) d 2.32 (s, 3H), 4.50 (s, 2H), 5.19 (s, 2H), 6.95 (s, ÍH), 7.05 (d, 2H) , 7.15 (d, 2H), 7.59 (s, ÍH) FAB (M + H): 219 47-2) 5-Chloromethyl-1 - (4-methylbenzyl) imidazole hydrochloride The title compound was obtained with a yield of 91% according to the same procedure as that used in Preparation 28-2), with the exception that the compound that was prepared in Preparation 47-1) was used as a starting material. Preparation 48: Synthesis of 5-chloromethyl-1- (3-methylbenzyl) imidazole 48-1) 5-Hydroxymethyl-1- (3-methylbenzyl) imidazole hydrochloride The title compound was obtained in 60% yield according to the same procedure as that used in Preparation 31-1) using dihydroxyacetone and 3-methylbenzylamine hydrochloride as starting materials.

XH NMR (CDC13) d 2.27 (s, 3H), 4.45 (s, 2H), 4.52 (br, ÍH), 5.13 (s, 2H), 6.80 (d, ÍH) , 6.90 (m, 2H), 7.08 (m, HH), 7.17 (m, HH), 7.34 (s, HH) FAB (M + H): 219 48-2) Hydrochloride 5-chloromethyl-1- (3-methylbenzyl) imidazole The title compound was obtained with a yield of 92% according to the same procedure as that used in Preparation 28-2), with the exception that the compound that was prepared in Preparation 48-1) was used as a starting material. Example 129: Synthesis of 1- [1- (4-methoxybenzyl) -lH-imidazol-5-yl] ethyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1- il) -lH-pyrrole (129) 62 mg (0.2 mmol) of the compound prepared in Example 114-2) were dissolved in 2 ml of dimethylformamide. There 26 mg (0.66 mmol) of sodium hydride was added at 0 ° C and the mixture was stirred for 5 minutes. 60 mg (0.22 mmol) of the compound prepared in Preparation 43-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 95/5, v / l). v) to obtain 77 mg (Yield 76%) of the title compound. XH NMR (CDC13) d 2.41 (m, 2H), 2.75 (m, 1H), 3.03 (m, 5H), 3.10 (m, HH), 3.34 (m, HH), 3.76 (m, 3H), 4.91 (s, 2H), 4.93 (s, 2H), 6.62 ( d, ÍH), 6.82 (d, 2H), 6.90-7.07 (m, 3H), 7.21 (s, ÍH), 7.32 (m, ÍH), 7.43 (m , 2H), 7.60 (s, 1H), 7.74 (d, ÍH), 7.82 (d, ÍH), 8.08 (d, ÍH) FAB (M + H): 509, C31H32N403 Example 130: Synthesis of 1- [1- (4-methoxybenzyl) -1H-imidazol-5-yl] methyl-3- (4-methylpiperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH- pyrrole (130) 64 mg (0.2 mmol) of the compound prepared in Example 125-1) were dissolved in 2 ml of dimethylformamide. There 26 mg (0.66 mmol) of sodium hydride was added at 0 ° C and the mixture was stirred for 5 minutes. 60 mg (0.22 mmol) of the compound prepared in Preparation 43-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off • reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 79 mg (Yield 80%) of the title compound. * H NMR (CDC13) d 1.06 (br, 2H), 1.72 (m, 2H), 1.82 (s, 3H), 2.86 (br, 2H), 3.28 (br, 2H) ), 3.75 (s, 3H), 4.91 (s, • 2H), 4.93 (s, 2H), 6.63 (d, ÍH), 6.82 (d, 2H), 6.90-7.07 (m, 3H), 7.23 (s, 1H), 7.33 (m, ÍH), 7.44 (m, 2H), 7.61 (s, 1H), 7.75 (d, ÍH), 7.82 (d, ÍH), 8, 08 (d, 1H) 15 FAB (M + H): 520, C32H33N502 Example 131: Synthesis of 1- [1- (3-chlorobenzyl) -lH-imidazol-5-yl] methyl-3- (4- methyl-piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (131) 64 mg (0.2 mmol) of the compound prepared in Example 125-1) were dissolved in 2 ml of dimethylformamide. There 26 mg (0.66 mmol) of sodium hydride was added at 0 ° C and the mixture was stirred for 5 minutes. 61 mg (0.22 mmol) of the compound prepared in Preparation 44-2) were added to the mixture, which was subsequently stirred at room temperature. atmosphere for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 75 mg (Yield 71%) of the title compound. XH NMR (C'DC13) d 1.02 (br, 2H), 1.78 (br, 2H), 1.87 (s, 3H), 2.84 (br, 2H), 3.30 (br, 2H), 6.64 (m, 2H), 7.01 (s, ÍH), 7.10-7.30 (m, 4H), 7.31-7.47 (m, 4H), 7.53 (s, ÍH), 7.73 (d, ÍH), 7.81 (d, ÍH), 7.96 (d, 1H) FAB (M + H): 524, C31H30N5OC1 Example 132: Synthesis of 1- [ 1- (3-Chlorobenzyl) -1H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -IH-pyrrole (132 62 mg (0.2 mmol) of the compound prepared in Example 114-2) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 61 mg (0.22 mmol) of the compound prepared in Preparation 44-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 95/5, v / l). v) to obtain 80 mg (Yield 78%) of the title compound. XH NMR (CDCl 3) d 2.39 (br, 2H), 2.71 (m, HH), 3.02 (br, 4H), 3.09 (br, HH), 3.32 (br, HH) , 4.09 (br, ÍH), 4.97 (s, 2H), 5.04 '(s, 2H), 6.64 (d, ÍH), 6.90 (m, ÍH), 7.02 (d, 2H), 7.20-7.40 (m, 4H), 7.40-7.60 (m, 3H), 7.74 (d, ÍH), 7.76 (d, 1H), 7.85 (s, ÍH), 8.04 (d, ÍH) FAB (M + H): 513, C30H29N4O2C1 Example 133: Synthesis of 1- [1- (2-Chlorobenzyl) -lH-imidazol-5-yl] methyl-3- (4-methylpiperazin-1-yl) carbonyl-4- (naph alen-1-yl) -lH-pyrrole ( 133) 64 mg (0.2 mmol) of the compound prepared in Example 125-1) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 61 mg (0.22 mmol) of the compound prepared in Preparation 45-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 80 mg (Yield 76%) of the title compound. XH NMR (CDC13) d 1, 06 (br, 2H), 1.80 (br, 2H), 1.86 (s, 3H), 2.84 (br, 2H), 3.30 (br, 2H), 4.98 (s, 2H), 5.11 (s, 2H), 6.63 (m, 2H), 7.01 (s, ÍH), 7.12-7.30 (m, 4H), 7.32-7.46 (m, 4H), 7.53 (s, ÍH), 7.73 (d, ÍH), 7.81 (d, ÍH), 7.97 (d, ÍH) FAB (M + H): 524, C31H30N5OC1 Example 134: Synthesis of 1- [1- (2-chlorobenzyl) -lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalene-1) -yl) -lH-pyrrole (134) 62 mg (0.2 mmol) of the compound prepared in Example 114-2) were dissolved in 2 ml of dimethylformamide. There 26 mg (0.66 mmol) of sodium hydride was added at 0 ° C and the mixture was stirred for 5 minutes. 61 mg (0.22 mmol) of the compound prepared in Preparation 45-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 95/5, v / l). v) to obtain 77 mg (Yield 75%) of the title compound. XH NMR (CDC13) d 2.37 (br, 2H), 2.72 (m, ÍH), 3.01 (br, 4H), 3.10 (br, ÍH), 3.32 (br, ÍH), 4.18 (br, ÍH), 5.04 (s, 2H), 5.17 (s, 2H), 6, 65 (d, 1H), 6.76 (d, 2H), 7.04 (d, ÍH), 7.13-7.35 (m, 4H), 7.36-7.50 (m, 4H), 7.71 (s, ÍH), 7.75 (d, ÍH), 7.82 (d, 1H), 8.01 (d, ÍH) FAB (M + H): 513, C30H29N4O2C1 Example 135: Synthesis of 1- [1- (2-fluobenzyl) -lH-imidazole- 5-yl] methyl-3- (4-methylpiperazin-1-yl) carbonyl-4- (n-aftalen-1-yl) -lH-pyrrole (135) 64 mg (0.2 mmol) of the compound prepared in Example 125-1) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 51 mg (0.22 mmol) of the compound prepared in Preparation 46-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 79 mg (Yield 77%) of the title compound. XH NMR (CDC13) d 1.06 (br, 2H), 1.80 (br, 2H), 1.86 (s, 3H), 2.93 (br, 2H), 3.35 (br, 2H) , 5.03 (s, 2H), 5.06 (s, 2H), 6.66 (m, 2H), 6.87 (m, ÍH), 7.12-7.30 (m, 4H), 7.32-7.46 (m, 4H), 7.58 (s, ÍH), 7.77 (d, ÍH), 7.82 (d, ÍH), 7.97 (d, ÍH) FAB ( M + H): 508, C31H30N5OF Example 136: Synthesis of 1- [1- (4-methyl-benzyl) -lH-imidazol-5-yl] methyl-3- (4-methyl-piperazin-1-yl) carbonyl -4- (naphthalen-1-yl) -lH-pyrrole (136) 64 mg (0.2 mmol) of the compound prepared in Example 125-1) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 57 mg (0.22 mmol) of the compound prepared in Preparation 47-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 81 mg (Yield 80%) of the title compound. XH NMR (CDC13) d 1.09 (br, 2H), 1.83 (br, 2H), 1.86 (s, 3H), 2.24 (s, 3H), 2.93 (br, 2H) , 3.30 (br, 2H), 4.86 (s, 2H), 4.91 (s, 2H), 6.59 (d, ÍH), 6.87 (m, 2H), 7.01 ( s, ÍH), 7.07 (d, 2H), 7.15 (s, HH), 7.25 (m, HH), 7.50 (m, 3H), 7.53 (s, HH), 7.73 (d, ÍH), 7.78 (d, ÍH), 7.97 (d, ÍH) FAB (M + H): 504, C32H33N50 Example 137: Synthesis of 1- [1- (4-methylbenzyl ) -lH-imidazol-5-yl] methyl-3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (137) 62 mg (0.2 mmol) of the compound prepared in Example 106-3) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 57 mg (0.22 mmol) of the compound prepared in Preparation 47-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 95/5, v / l). v) to obtain 80 mg (yield 81%) of the title compound. XH NMR (CDC13) d 2.29 (s, 3H), 2.30-3.60 (br, 8H), 4.94 (s, ÍH), 4.99 (s, 2H), 6.61 ( d, ÍH), 6.91 (d, ÍH), 7.07 (d, ÍH), 7.12 (d, 2H), 7.21 (s, ÍH), 7.32 (d, ÍH), 7.35-7.50 (m, 4H), 7.71 (s, ÍH), 7.77 (d, ÍH), 7.84 (d, ÍH), 7.98 (d, ÍH) FAB ( M + H): 491, C31H30N4O2 Example 138: Synthesis of 1- [1- (3-methylbenzyl) -lH-imidazol-5-yl] methyl-3- (4-methylpiperazin-1-yl) carbonyl-4- ( Naphthalen-1-yl) -lH-pyrrole (138) 64 mg (0, 2 mmol) of the compound prepared in Example 125-1) were dissolved in 2 ml of dimethylformamide. There, 26 mg (0.66 mmol) of sodium hydride were added at 0 ° C and the mixture was stirred for 5 minutes. 57 mg (0.22 mmol) of the compound prepared in Preparation 48-2) were added to the mixture, which was subsequently stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue. The resulting mixture was extracted twice with 10 ml of ethyl acetate, dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel. (eluent: dichloromethane / methanol = 90/10, v / v) to obtain 74 mg (Yield 73%) of the title compound. 1ti NMR (CDCl 3) d 1.06 (br, 2H), 1.80 (br, 2H), 1.84 (s, 3H), 2.91 (br, 2H), 3.27 (br, 2H) , 4.86 (s, 2H), 4.89 (s, 2H), 6.57 (d, 1H), 6.71 (d, ÍH), 6.77 (s, ÍH), 6.97 ( s, ÍH), 7.01 (d, ÍH), 7.15 (m, 2H), 7.25 (d, ÍH), 7.37 (m, 3H), 7.51 (s, ÍH), 7.70 (d, HH), 7.72 (d, HH), 7.98 (d, HH) FAB (M + H): 504, C32H33N50 Preparation 49: Synthesis of 3- (naphthalen-1-yl) carbonyl-lH-pyrrole 49-1) methyl N-methyl-1-naphthalene-hydroxamate 3.44 g (20 mmol) of 1-naphthoic acid were dissolved in 20 ml of dimethylformamide and then 4.6 g (24 mmol) of EDC, 2.02 g (20 mmol) of triethylamine and 3.24 g (24 mmol) of HOBT were incorporated therein. The resulting mixture was stirred at 0 ° C for 5 minutes. To the reaction solution was added 1.85 g (20 mmol) of N, O-dimethylhydroxylamine hydrochloride, which was subsequently stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and then 100 ml of a saturated potassium carbonate solution was added to the residue. The resulting solution was extracted with ethyl acetate. Then, the organic layer was washed sequentially with an aqueous solution of 1 N hydrochloric acid, an aqueous solution of sodium chloride and water, dried over anhydrous sodium sulfate and concentrated to obtain 3.04 g (1.50 mmol) of the composed of the title. 1 NM NMR (CDC13) δ 2.42 (s, 3H), 3.24 (s, 3H), 7.47 (m, 4H), 7.67 (d, HH), 7.74 (m, 2H) , FAB 216 (M + H) 49-2) 1- (Naphthalen-1-yl) -prop-2-en-l -one 2.03 g (9.4 mmol) of the compound prepared in Preparation 49-1 ) were dissolved in 20 ml of dry tetrahydrofuran, and then there slowly added 20 ml of a solution of magnesium bromide IN-tetrahydrofuran at 0 ° C. The mixture was stirred at room temperature for 30 minutes and therein was added 20 ml of IN hydrochloric acid. Subsequently, the resulting solution was extracted with 50 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure to obtain 1.63 g (9 mmol, 96% yield) of the title compound. ? ti NMR (CDC13) d 6.92 (m, 1H), 7.51 (m, 4H), 7.74 (d, ÍH), 7.85 (m, 2H), 7.98 (d, 1H) ), 8.31 (d, ÍH) 49-3) 3- (Naphthalen-1-yl) carbonyl-lH-pyrrole 901 mg (5 mmol) of the compound prepared in Preparation 49-2) and 1.01 g ( 5.5 mmol) of tosylmethyl isocyanide were dissolved in 10 ml of tetrahydrofuran. There, 555 mg (5.5 mmol) of potassium t-butoxide dissolved in 10 ml of tetrahydrofuran were slowly added and the mixture was stirred for 30 minutes. 10 ml of water were added to the reaction solution to stop the reaction and the solvent was removed under reduced pressure. 20 ml of water was added to the residue and the resulting mixture was extracted with ethyl acetate, washed with an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to column chromatography with silica gel (eluent: ethyl acetate / hexane = 1/3, v / v) to obtain 884 mg (4 mmol, Yield 80%) of the title compound. 1rl NMR (CDCl 3) d 6.57 (s, ÍH), 6.66 (s, ÍH), 6.79 (s, ÍH), 7.36 (m, 3H), 7.48 (d, 1H) , 7.77 (d, ÍH), 7.82 (d, ÍH), 8.04 (d, ÍH), 9.91 (s, ÍH) Preparation 50: Synthesis of 4- (na alen-1-il ) carbonyl-3- [N- (2-methoxyethyl) -N-methylcarbamoyl] -lH-pyrrole 50-1) 4 - (Naphthalen-1-yl) -4-oxo-2-bu-tenoic acid 5.88 g ( 60 mmol) of dry maleic acid were dissolved in 100 -. 100 ml dry tetrahydrofuran and the mixture was cooled to 78 ° C. 4.14 g (20 mmol) of 1-bromonaphthalene were dissolved in 100 ml of dry tetrahydrofuran and 13.8 ml of a solution of n-butyllithium-hexane 1.6N were incorporated therein at 78 ° C. This reaction solution was stirred for 5 minutes and then it was added to the dry maleic acid solution that was prepared above, using a cannula. The resulting mixture was stirred for 10 minutes and water was added thereto, to stop the reaction. The solvent was removed under reduced pressure and the residue was acidified by an aqueous solution of IN hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and subjected to column chromatography (eluent: ethyl acetate / hexane = 2/1, v / v) to obtain 1.35 g (6.0 mmol; Yield 30%) of the title compound. XH NMR (CDC13) d 6.81 (d, ÍH), 7.52-7.65 (m, 3H), 7.85 (d, ÍH), 7.89 (d, ÍH), 7.92 ( d, 1H), 8.06 (d, HH), 8.56 (d, HH) 50-2) N- (2-methoxyethyl) -N-methyl -4 - (naphthalene-1-yl) -4- oxo-2-butenoamide 1.3 g (5.9 mmol) of the compound prepared in Preparation 50-1) were dissolved in 10 ml of dimethylformamide, and then 1.7 g (8.9 mmol) of EDC and 1, 2 g (8.9 mmol) of HOBT were added there, at 0 ° C. The resulting mixture was stirred for 5 minutes. To the reaction solution were added 530 mg (5.9 mmol) of N- (2-methoxyethyl) -N-methylamine and 1.2 ml (8.9 mmol) of triethylamine, which mixture was subsequently stirred at room temperature, for 2 hours. The solvent was removed under reduced pressure and then 50 ml of water was added to the residue. The resulting solution was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (eluent: ethyl acetate / hexane = 1/1, v / v) to obtain 1.4 g (4.7 mmol; Yield 80%) of the title compound. XH NMR (CDC13) d 3.05 (s, 3H), 3.32 (s, 3H), 3.54 (m, 2H), 3.65 (m, 2H), 7.40-7.58 ( m, 4H), 7.71 (t, ÍH), 7.89 (m, 2H), 8.03 (d, ÍH), 8.54 (d, 1H) 50-3) 3- [N- ( 2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) carbonyl-lH-pyrrole 1.4 g (4.7 mmol) of the compound prepared in Preparation 50-2) and 1.0 g (5.1 mmol) of tosylmethyl isocyanide were dissolved in 20 ml of tetrahydrofuran. There 790 mg (7.0 mmol) of potassium t-butoxide were added and the mixture was stirred at room temperature for 3 hours. 2 ml of water were added to the reaction solution to stop the reaction and the solvent was removed under reduced pressure. The residue was extracted with ethyl acetate, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was subjected to column chromatography - ^ (eluent: ethyl acetate / hexane = 2/3, v / v) to obtain .2 g (3.6 mmol, yield 76%) of the title compound. XH NMR (CDC13) d 3.04 (s, 3H), 3.35 (s, 3H), 3.47 (m, 2H), 3.64 (m, 2H), 6.55 (d, ÍH) , 6.63 (m, HH), 7.21-7.40 (m, 4H), 7.74 (m, 2H), 8.00 (m, HH), 11.4 (br, HH) Example 139: Synthesis of 1- [1- (4-cyanobenzyl) -10 lH-imidazol-5-yl] methyl-3- (naphthalen-1-yl) carbonyl-lH-pyrrole (139) The title compound was obtained with a performance of % according to the same procedure as that used in Example 1, with the exception that the compound was used prepared in Preparation 29-5) and the compound prepared in Preparation 49-3). XH NMR (CDC13) d 4.86 (s, 2H), 4.95 (s, 2H), 6.52 (s, 1H), 6.61 (s, ÍH), 6.89 (m, 3H) , 7.20 (s, ÍH), 7.49 (m, 6H), 7.75 (s, ÍH), 7.87 (d, ÍH), 7.95 (d, 1H), 8.11 ( d, ÍH) 20 FAB: 417 (M + 1) Example 140: Synthesis of 1- [1- (4-bromo-benzyl) -lH-imidazol-5-yl] methyl-3- (naphthalen-1-yl) carbonyl-lH-pyrrole (140) The title compound was obtained with a yield of 20% according to the same procedure as that used in Example 1, with the exception that the compound prepared in Preparation 32-2) and the compound prepared in Preparation 49-3) were used.

XH NMR (CDC13) d 4, .84 (s, 2H), 4.92 (s, 2H), 6.54 (s, ÍH), 6.67 (s, ÍH), 6.78 (d, 2H ), 6.93 (s, ÍH),. 7.22 (s, ÍH), 7.38 (d, 2H), 7.50 (m, 3H), 7.58 (d, ÍH), 7.89 (d, 1H), 7.95 (d , HH), 8.13 (d, HH), 8.16 (s, 1H) FAB: 470 (M + 1) Example 141: Synthesis of 1- [1- (4-bromobenzyl) -lH-imidazole-5 -yl] methyl-3- [N- (2-methoxyethyl) -N-ethyl] carbamoyl-4- (naphthalen-1-yl) carbonyl-lH-pyrrole (141) The title compound was obtained in a yield of 81%. % according to the same procedure as that used in Example 1, with the exception that the compound prepared in Preparation 32-2) and the compound prepared in Preparation 50-3 were used). XH NMR (CDC13) d 2.94 (s, 3H), 3.25 (s, 3H), 3.42 (m, 2H), 3.48 (m, 2H), 4.72 (s, 2H) , 4.78 (s, 2H), 6.64 (m, 4H), 7.28-7.48 (m, 8H), 7.81 (m, 2H), 8.14 (m, ÍH) FAB : 585 (M + l) Preparation 51: Synthesis of ethyl 1-naphthoylglycinate hydrochloride 51 -1) Ethyl N- (dif enylmethylene) glycinate The salt of glycine ethyl ester hydrochloride and diphenyl ethylimine were reacted according to the procedure describes in MJ O'Donnell, RL Polt, J. Org. Chem 47, 2663, 1982, to obtain the title compound in 90% yield. XH NMR (CDC13) d 1.20 (t, 3H), 4.12 (m, 4H), 7.10-7.40 (m, 8H), 7.59 (d, 2H) 51 -2) Chlorhydrate of 1-naphthoylglycine to ethyl 1-naphthoyl chloride and the compound prepared in Preparation 51-1) were reacted according to the procedure described in J. Singh et al.

Tetrahedron Lett. , 34 (2), 211, 1993 to obtain the title compound with a yield of 48%. XH NMR (DMS0-d6) d 1.78 (s, 3H), 3.65 (q, ÍH), 3.95-4.15 (m, 2H), 6.33 (s, ÍH), 7, 58-7.85 (m, 3H), 8.15 (d, lH), 8.31 (d, lH), 8.38 (d, 2H), 8.42 (d, 2H) Preparation 52: Synthesis of 2- [1- (4-chlorobenzyl) -lH-imidazol-5-yl] thioacetamide 52-1) 1- (4-Chlorobenzyl) -5-hydroxymethyl-1H-imidazole The title compound was obtained in a yield of 50% according to a procedure similar to that described in J.M.Dener, L-H Zhang, H. Rapoport, J. Org. Chem., 1993, 58, 1159, using a dihydroxyacetone dimer and 4-chlorobenzylamine hydrochloride as starting materials.

XH NMR (CDC13 + CD3OD) d 4.50 (s, 2H), 5.20 (s, 2H), 6.94 (s, lH), 7.06 (d, 2H), 7.32 (d, 2H), 7.46 (s, lH) 52-2) 1- (4-Chlorobenzyl) -5-chloromethyl-lH-imidazole hydrochloride 3.00 g (13.5 mmol) of the compound prepared in Preparation 52 -1) were dissolved in 40 ml of chloroform. There, 2.88 ml (40.5 mmol) of thionyl chloride were slowly added at 0 ° C and the mixture was stirred at room temperature for 2 hours. The organic solvent was removed under reduced pressure to obtain 3.64 g (13.1 mmol, 97% yield) of the title compound. This compound was used directly in the next reaction without purification. 52-3) [1- (4-Chlorobenzyl) -lH-imidazol-5-yl] acetoni trile 1.2 g (4.3 mmol) of the compound prepared in Preparation 52-2) were dissolved in 10 ml of sulfoxide of dimethyl and therein was added 1.3 g (26 mmol) of sodium cyanide. The mixture was stirred at room temperature for 6 hours. 30 ml of water were added there and the resulting mixture was extracted with ethyl acetate (20 ml x 3). The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain 0.96 g (4.1 mmol, 96% yield) of the title compound. This compound was used in the next reaction without purification. 1 NMR (CDC13) d 3.70 (s, 2H), 5.12 (s, 2H), 6.88 (s, lH), 7.34 (d, 2H), 7.62 (d, 2H) 7.71 (s, lH) 52-4) 2- [1- (4-Chlorobenzyl) -1H-imide zol-5-yl] thioacetamide 150 mg (0.64 mmol) of the compound prepared in Preparation 52- 3) were dissolved in a solvent mixture of 1 ml of pyridine and 0.3 ml of triethylamine and then saturated by bubbling with hydrogen sulfide gas through the solution for 30 minutes. The reaction solution was stirred at room temperature for 12 hours. The solvent was removed under reduced pressure and 10 ml of water were added thereto. The mixture was extracted with 10 ml of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: methylene chloride / methanol = 20/1, v / v) to obtain 110 mg (0.41 g). mmol, 64% yield) of the title compound. XH NMR (CDC13 + CD3OD) d 3.21 (s, 2H), 5.05 (s, 2H), 6.76 (s, lH), 7.24 (d, 2H), 7.61 (d, 2H), 7.67 (s, lH) FAB: 266 (M + 1) Preparation 53: Synthesis of 2-. { 1- [1- (benzyloxycarbonyl) piperidin-4-yl] methyl-lH-imidazol-5-yl} thioacetamide 53-1) 4-Aminomethyl-1 - (benzyloxycarbonyl) piperidine 22.2 g (0.2 mol) of 4-aminomethylpiperidine were dissolved in 250 ml of toluene and there 21.2 g (0.2 mol) were added. ) of benzaldehyde. The reaction mixture was refluxed for 3 hours with Dean-Starck to remove the water and then cooled to 0 ° C. There, slowly 34.2 g (0.2 mol) of benzylchloro-forma were incorporated, while stirring. The mixture was stirred at room temperature for 3 hours and 220 ml of an aqueous KHS0 IN solution was added thereto. The mixture was extracted three times with 200 ml of diethyl ether and the aqueous layer was basified with a 1N aqueous sodium hydroxide solution. The aqueous solution was saturated with sodium chloride. The aqueous layer was extracted three times with 100 ml of dichloromethane, dried over anhydrous magnesium sulfate and distilled under reduced pressure to obtain 38 g (Yield 91%, molecular weight 248) of the title compound. XH NMR (CDC13) d 1.11 (s, 2H), 1.49 (s, 3H), 1.70 (d, 2H), 2.57 (d, 2H), 2.78 (s, 2H) 4.20 (s, 2H). 5.12 (s, 2H), 7.34-7.35 (m, 5H) 53-2) 1 - [1 - (Benzyloxycarbonyl) piper idin-4-yl] met il-5-hydroxymethyl 2 - mer capto-lH-imidazole 2A, Q g (0.1 mol) of the compound prepared in Preparation 53-1) and 6.0 g (0.1 mol) of acetic acid were dissolved in 50 ml of n-butanol. A solution in which 12.6 g (0.13 mol) of potassium thiocyanate, 15.2 g (0.1 mol) of 1,3-dihydroxyacetone dimer and 10.0 g (0.17 g) were dissolved. mol) of acetic acid in 50 ml of n-butanol was added thereto and the whole mixture was stirred at room temperature. After 48 hours, the solvent was distilled off under reduced pressure and then the residue was dissolved in 200 ml of ethyl acetate and washed three times with 100 ml of water. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain 27 g (75 mmol, 75% yield) of the title compound. XH NMR (CDC13) d 1.22 (d, 2H), 1.57 (d, 2H), 2.30 (s, lH), 2.72 (s, 2H), 3.96 (s, 2H) , 4.15 (d, 2H), 4.46 (s, 2H), 5.10 (s, 2H), 6.62 (s, lH), 7.26-7.37 (m, 5H) 53 -3) 1 - [1 - (Benzyloxycarbonyl) piperidin-4-yl] methyl -5-Hydroxymethyl-1H-imide zol 18.05 g (50 mmol) of the compound prepared in Preparation 53-2) were added to a mixture of 100 ml of 10% nitric acid and 10 ml of ethyl acetate. The resulting reaction mixture was cooled with ice water and then stirred at room temperature for 3 hours. The mixture was basified using an aqueous solution of 4N sodium hydroxide and extracted twice with 100 ml of ethyl acetate. The extracted organic solution was dried over magnesium sulfate and distilled under reduced pressure to obtain 12.3 g (38 mmol, 75% yield) of the title compound.

X H NMR (CDCl 3) d 1.16 (d, 2 H), 1.56 (d, 2 H), 1.98 (s, 1 H), 2.70 (s, 2 H), 3.88 (d, 2 H) , 4.18 (s, 2H), 4.49 (s, lH), 4.56 (s, 3H), 5.10 (s, 2H), 6.82 (s, lH), 7.27- 7.40 (m, 6H) 53-4) 1 - [1 - (Benzyloxycarbonyl) piperidin-4-yl] methyl-5-chloroethyl-1H-imidazole hydrochloride 9.9 g (30 mmol) of the compound prepared in Preparation 53-3) were dissolved in 50 ml of chloroform and 7.1 g (60 mmol) of thionyl chloride were added there, slowly, at 0 ° C. The reaction solution was stirred for 2 hours and the solvent was distilled off under reduced pressure to obtain -9.9 g (95% yield, molecular weight 347.5) of the hydrochloride salt of the title compound. This compound was used directly in the next reaction without purification. 53-5). { 1 - [1 - (Benzyloxycarbonyl) piper idin-4-yl] methyl-1H-imidazol-5'-yl} acetonitrile The title compound was obtained in a yield of 39% according to a procedure similar to that employed in Preparation 52-3), using the compound prepared in Preparation 53-4). X H NMR (CDCl 3) d 1.19 (br, 2 H), 1.60 (br, 2 H), 1.90 (m, H H), 2.72 (br, 2 H), 3.71 (s, 2 H) , 3.81 (d, 2H), 4.22 (br, 2H), 5.11 (s, 2H), 7.03 (s, lH), 7.29-7.36 (m, 5H), 7.51 (s, lH) 53-6) 2-. { 1 - [1 - (Benzyloxycarbonyl) piper idin-4-yl] met il -1 H-imidazol-5-yl} thioacetamide The title compound was obtained with a yield of 74% according to a procedure similar to that used in Preparation 52-4), using the compound prepared in Preparation 53-5). XH NMR (CDC13) d 1.21 (br, 2H), 1.63 (br, 2H), 1.87 (m, lH), 2.71 (br, 2H), 3.31 (s, 2H) , 3.84 (d, 2H), 4.25 (br, 2H), 5.12 • (s, 2H), 7.10 (S, 1H), 7.33-7.41 (m, 5H), 7.62 (s, lH) FAB: 373 (M + l) Preparation 54: Synthesis of methyl 3-chloro-3- (naphthalen-1-yl) -2-oxo-propionate 7.80 g (49.9 mmol) of 1-naphthaldehyde and 7.15 g (49.9 mmol) of methyl dichloroacetate were dissolved in 100 ml of t-butanol and there were incorporated 6.15 g (54.8 mmol) of potassium t-butoxide, at 0 ° C. The mixture was stirred at room temperature for 24 hours and then 50 ml of water was added to stop the reaction. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate.

Ethyl. The organic layer was dried over magnesium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: n-hexane / ethyl acetate = 9/10/10, v / v) to obtain 2.5 g. (9.52 mmol, Yield 19%) of the title compound. • 20 X H NMR (CDCl 3) d 3.78 (s, 3 H), 6.92 (s, 1 H), 7.45-7.73 (m, 4 H), 7.95 (m, 2 H), 8, 12 (d, 1H) Preparation 55: Synthesis of methyl 2-chloro-3- (naphthalen-1-yl) -3-oxo-propionate 55-1) 3- (methyl-naphthalene-1-yl) -3-oxo-propionate 25 2 g (59.9 mmol) of 1-acetonaphthone and 4.8 g (60% in mineral oil, 120 mmol) of sodium hydride were added to 100 ml of dimethyl carbonate and the mixture was refluxed for 24 hours . The solvent was removed under reduced pressure, 100 ml of an aqueous solution of IN HCl was added to the residue and the resulting mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed with water (100 ml x 3), dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to column chromatography with silica gel (eluent: n-hexane / ethyl acetate = 90/10, v / v) to obtain 10.0 g (43.8 mmol, yield 73%) of the compound of the title. XH NMR (CDC13) d 3.75 (s, 3H), 4.14 (s, 2H), 7.45-7.68 (m, 3H), 7.82-8.08 (m, 3H), 8.77 (d, lH) 55-2) methyl 2-chloro-3- (naphthalen-l -yl) -3-oxopropionate 4.56 g (20.0 mmol) of the compound prepared in Preparation 55-1 ) were dissolved in 50 ml of 1,2-dichloroethane and there were slowly added 2.70 g (20.0 mmol) of sulfuryl chloride at 0 ° C. The mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure to obtain 4.70 g (17.9 mmol, 89% yield) of the title compound. ti NMR (CDCl 3) d 3.75 (s, 3H), 5.82 (s, 2H), 7.50-7.72 (m, 3H), 7.85-8.15 (m, 3H), 8.65 (d, lH) Example 142: Synthesis of 4-ethoxycarbonyl-2- (1H-imidazol-5-ylmethyl) -5- (naphthalen-1-yl) oxazole (142) 142-1) Ethyl 2- [ (lH-imidazol-5-yl) acetylamino] -3- (naphthalen-1-yl) -3-oxopropion to 293 mg (0.997 mmol) of the compound prepared in Preparation 51-2), 162 mg (0.996 mmol) of 4-imidazoleacetic acid hydrochloride, 135 mg (0.999) mmol) of HOBT and 191 mg (0.996 mmol) of EDC were added to 10 ml of dimethylformamide and therein, 202 mg (1.99 mmol) of triethylamine were slowly added thereto while stirring. The mixture was stirred at room temperature for 5 hours and then the solvent therein was removed under reduced pressure. To the residue were added 30 ml of ethyl acetate, which was then washed with a saturated solution of sodium bicarbonate and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 95/5, v / v) to obtain 200 mg (0.547 mmol, yield 55). %) of the title compound. 1 H NMR (CDC13) δ 0.92 (t, 3H), 3.70 (s, 2H), 3.98-4.15 (m, 2H), 6.20 (d, ÍH), 6.92 ( s, lH), 7.55 (m, 4H), 7.65 (s, lH), 7.89 (d, lH), 8.06 (d, ÍH), 8.12 (br, ÍH), 8.21 (d, lH), 8.45 (d, lH) 142-2) 4-Ethoxycarbonyl -2- (lH-imidazol-5-ylmethyl) -5- (naphthalen-1-yl) oxazole 100 mg ( 0.27 mmol) of the compound prepared in Example 142-1) were dissolved in 5 ml of THF and then refluxed for 6 hours. The solvent was distilled off under reduced pressure and the residue was subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 95/5, v / v) to obtain 40 mg (0.12 mmol, yield 44). %) of the title compound. XH NMR (CDC13) d 0.98 (t, 3H), 4.13 (q, 2H), 4.27 (s, 2H), 6.92 (s, lH), 7.45-7.58 ( m, 4H), 7.65-7.75 (m, 2H), 7.89 (d, 1H), 7.97 (d, 1H) FAB: 348 (M + 1) Example 143: Synthesis of 2- (lH-imidazol-5-ylmethyl) -4- (morpholin-4-yl) carbonyl-5- (naphthalen-1-yl) oxazole (143) 31 mg (0.09 mmol) of the compound prepared in Example 142- 2) were dissolved in a mixture of tetrahydrofuran / methanol / water solvents (0.6 ml / 0.3 ml / ml) and there were added 6 mg (0.13 mmol) of lithium hydroxide. The reaction solution was stirred at room temperature for 3 hours and the solvent was removed under reduced pressure. The residue was adjusted to a pH of 6 using an aqueous solution of 0.1 N hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried in anhydrous sodium sulfate and concentrated. The concentrate was dissolved in 1 ml of dimethylformamide. There 18 mg (0.13 mmol) of HOBT and 26 mg (0.13 mmol) of EDC were added at 0 ° C and the mixture was stirred for 10 minutes. 9 μl (0.09 mmol) of morpholino and 18 μl (0.13 mmol) of triethylamine were incorporated therein and the mixture was stirred at room temperature for 2 hours. The reaction solution was treated according to the same procedure as that used in Example 142-1) to obtain 14 mg (0.04 mmol, 45% yield) of the title compound. XH NMR (CDC13) d 2.97 (br, 2H), 3.24 (br, 2H), 3.43 (br, 2H), 3.57 (br, 2H), 4.27 (s, 2H) 6.95 (s, lH), 7.52-7.67 (m, 6H), 7.81-7.95 (m, 3H) FAB: 389 (M + l) Example 144: Synthesis of 4- ethoxycarbonyl-2- (1H-imidazol-5-ylmethyl) -5- (naphthalen-1-yl) thiazole (144) 105 mg (0.287 mmol) of the compound prepared in Example 142-1) and 116 mg (0.287 mmol) of Lawesson's Reagent were dissolved in 10 ml of tetrahydrofuran and the mixture was refluxed for 6 hours. The solvent was removed under reduced pressure; 10 ml of a solution of baking soda • Saturated sodium was added to the residue and then the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 95/5, v / v) to give 26 mg (0.075 mmol, yield 26). %) of the compound of Example 142-2) and 24 mg (0.066 mmol, 23% yield) of the title compound. XH NMR (CDC13) d 0.63 (t, 3H), 3.92 (q, 2H), 4.42 (s, 2H), 6.97 (s, lH), 7.405-7.75 (m, 6H), 7.85-7.95 (m, 2H) 15 FAB: 364 (M + l) Example .145: Synthesis of 2- [1- (4-chlorobenzyl) -1H-imidazol-5-ylmethyl] - 4-methoxycarbonyl-5- (naphthalen-1-yl) thiazole (145) 130 mg (0.49 mmol) of the compound prepared in Preparation 20-4) and 129 mg (0.49 mmol) of the compound prepared in Preparation 54 were dissolved in 5 ml of - ethanol and the mixture was refluxed for 5 hours. The solvent was distilled off under reduced pressure and the residue was subjected to column chromatography with gel Silica (eluent: dichloromethane / methanol = 40 μl, v / v) to obtain 45 mg (0.095 mmol, Yield 19%) of the title compound. XH NMR (CDCl 3) d 3.50 (s, 3H), 4.26 (s, 2H), 5.11 (s, 2H), 6.92 (d, 2H), 7.07 (s, ÍH) , 7.21-7.43 (m, 7H), 7.53 (s, lH), 7.83 (m, 2H) FAB: 474 (M + 1) Example 146: Synthesis of 2- [1- ( 4-chlorobenzyl) -lH-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-5- (naphthalen-1-yl) thiazole (146) The title compound was obtained in a yield of 23% according to a procedure similar to that employed in Example 143, using the compound prepared in Example 145. 1ti NMR (CDC13) d 2.63 (br, 2H), 3.02 (br, 2H), 3.24 ( br, 2H), 3.42 (br, 2H), 4.26 (s, 2H), 5.21 (s, 2H), 7.02 (m, 2H), 7.18 (s, lH), 7.31 (m, 2H), 7.43-7.60 (m, 5H), 7.78-7.96 (m, 3H) FAB: 529 (M + 1) Example 147: Synthesis of 2- [1- (4-chlorobenzyl) -1H-imidazol-5-ylmethyl] -4- [N- (2-methoxy) ethyl-N-methylcarbamoyl] - 5- (naph alen-1-yl) thiazole (147) The title compound was obtained with a yield of 41% according to a procedure similar to that employed in Example 143, using the compound prepared in Example 145, with the exception that it was used N- (2-methoxyethyl) methylamine in place of morpholino. XH NMR (CDCl 3) d 2.68 (br, 3H), 2.89-3.39 (m, 7H), 4.22 (s, 2H), 5.17 (s, 2H), 7.01 ( m, 2H), 7.15 (s, lH), 7.33 (m, 2H), 7.40-7.61 (m, 5H), 7.71-7.82 (m, 3H) FAB: 531 (M + l) Example 148: Synthesis of 2- [1- (4-Chlorobenzyl) -lH-imidazol-5-ylmethyl] -5-methoxycarbonyl-4- (naphthalen-1-yl) -iazole (148) 250 mg (0.95 mmol) of the compound prepared in Preparation 52-4) and 249 mg (0.95 mmol) of the compound prepared in Preparation 55-2) were dissolved in 10 ml of ethanol and the mixture was refluxed for 24 hours. The solvent was distilled off under reduced pressure and the residue was subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 40/1, v / v) to obtain 180 mg (0.38 mmol, Yield 40 %) of the title compound. XH NMR (CDC13) d 3.53 (s, 3H), 4.22 (s, 2H), 5.12 (s, 2H), 6.91 (m, 2H), 7.11 (s, ÍH) , 7.21-7.54 (m, 7H), 7.83 (m, 3H) FAB: 474 (M + l) Example 149: Synthesis of 2- [1- (4-chlorobenzyl) -1H-imidazole- 5-ylmethyl] -5- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) thiazole (149) The title compound was obtained with a yield of 39% according to a procedure similar to that used in Example 143, using the compound prepared in Example 148. XH NMR (CDC13) d 2.38 (br, 2H), 2.82 (br, 2H), 3.21 (br, 2H), 3.42 (br, 2H), 4.27 (s, 2H), 5.21 (s, 2H), 6.98 (m, 2H), 7.25 (m, 3H), 7.50-7.61 (m, 2H), m, 5H), 7.89-7.99 (m, 3H) FAB: 529 (M + 1) Example 150: Synthesis of 2-. { 1- [1- (benzyloxycarbonyl) piperidin-4-ylmethyl] -1H-imidazol-5-ylmethyl} -5-methoxycarbonyl-4- (naphthalen-1-yl) iazole (150) 124 mg (0.33 mmol) of the compound prepared in Preparation 53-6) and 87 mg (0.33 mmol) of the compound to be prepared in Preparation 55-2) were dissolved in 10 ml of ethanol and the mixture was refluxed for 20 hours. The solvent was distilled off under reduced pressure and the residue was subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 95/5, v / v) to obtain 95 mg (0.16 mmol, yield 48). %) of the title compound. XH NMR (CDC13) d 1.10 (br, 2H), 1.53 (br, 3H), 2.50 (br, 2H), 3.62 (s, 3H), 3.81 (d, 2H) , 4.19 (br, 2H), 4.41 (s, 2H), 5.14 (d, 2H), 7.16 (s, lH), 7.27-7.61 (m, 10H), 7.78 (s, lH), 7.91 (d, lH), 7.96 (d, lH) FAB: 595 (M + l) Example 151: Synthesis of 2-. { l- [1- (benzyloxycarbonyl) piperidin-4-ylmethyl] -lH-imidazol-5-ylmethyl} -5- [N- (2-methoxy) ethyl-N-methylcarbamoyl] -4- (naphthalen-1-yl) thiazole (151) The title compound was obtained in a yield of 36% according to a procedure similar to employed in the Example 143, using the compound prepared in Example 150, with the exception that it was used N- (2-methoxyethyl) methylamine in place of morpholino. XH NMR (CDCl 3) d 2.68 (br, 3H), 2.89-3.39 (m, 7H), 4.22 (s, 2H), 5.17 (s, 2H), 7.01 ( m, 2H), 7.15 (s, lH), 7.33 (m, 2H), 7.40-7.61 (m, 5H), 7.71-7.82 (m, 3H) FAB: 638 (M + l) Preparation 56: Synthesis of the 4- (5-chloromethyl-lH-imidazol-1-yl-methyl) -piperidine-1-carboxylic acid benzyl ester 56-1) 4-aminomethyl-piperidinyl benzyl ester 1-carboxylic acid 22.2 g (0.2 mol) of 4-aminomethyl-piperidine were dissolved in 250 ml of toluene and then 21.2 g (0.2 mol) of benzaldehyde were incorporated therein. The mixture was refluxed for 3 hours with Dean-Stack and cooled until it reached 0 ° C. Subsequently, 34.2 g (0.2 mol) of benzylchloroformate were added thereto while stirring. After the mixture was stirred for 3 hours, an aqueous solution of potassium hydrosulfate IN (220 ml) was added at room temperature. The mixture was extracted three times with 200 ml of diethyl ether and then the aqueous layer was basified with sodium hydroxide. The aqueous solution was saturated with sodium chloride and extracted three times with 100 ml of dichloromethane. The organic solution was dried in magnesium sulfate and. was distilled under reduced pressure to obtain 38 g (Yield 91%, molecular weight 248) of the title compound. XH NMR (CDC13) d 1.11 (s, 2H), 1.49 (s, 3H), 1.70 (d, 2H), 2.57 (d, 2H), 2.78 (s, 2H) , 4.20 (s, 2H), 5.12 (s, 2H), 7.34-7.35 (m, 5H) FAB (M + H): 249 56-2) Benzylester of 4- (5) acid Hydroxymethyl-2-mercapto-lH-imidazol-1-ylmethyl) -piperidin-1-carboxylic acid 24.8 g (0.1 mol) of the compound prepared in Preparation 56-1) and 6.0 g (0.1 mol) of acetic acid were dissolved in 50 ml of n-butanol and then the resulting solution was added to a solution, in which 12.6 g (0.13 mol) of potassium thiocyanate, 15.2 g (0, 1 mol) of 1,3-dihydroxyacetone dimer and 10.0 g (0.17 mol) of acetic acid were dissolved in 50 ml of n-butanol. The whole mixture was stirred for 48 hours. The solvent was removed by distillation under reduced pressure. There 200 ml of ethyl acetate were added and the mixture was washed three times with 100 ml of water. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure to obtain 27 g (75 mmol, 75% yield, Molecular weight 361) of the title compound. XH NMR (CDC13) d 1.22 (d, 2H), 1.57 (d, 2H), 2.30 (s, lH), 2.72 (s, 2H), 3.96 (s, 2H) , 4.15 (d, 2H), 4.46 (s, 2H), 5.10 (s, 2H), 6.62 (s, lH), 7.26-7.37 (m, 5H) FAB (M + H): 362 56-3) 4- (5-Hydroxymethyl-1H-imidazol-1-ylmethyl) -piperidino-1-carboxylic acid benzyl ester 18.05 g (50 mmol) of the compound prepared in Preparation 56 -2) were added to a mixture of 100 ml of nitric acid (10%) and 10 ml of ethyl acetate. The whole mixture was immersed in ice water for 5 minutes and stirred at room temperature for 3 hours. The mixture was basified with an aqueous solution of 4N sodium hydroxide and then extracted twice with 100 ml of ethyl acetate. The organic extract was dried over magnesium sulfate and distilled under reduced pressure to obtain 12.3 g (38 mmol, yield 75%, molecular weight 329) of the title compound. X H NMR (CDCl 3) d 1.16 (d, 2 H), 1.56 (d, 2 H), 1.98 (s, 1 H), 2.70 (s, 2 H), 3.88 (d, 2 H) , 4.18 (s, 2H), 4.49 (s, lH), 4.56 (s, 3H), 5.10 (s, 2H), 6.82 (s, lH), 7.27- 7.40 (m, 5H) FAB (M + H): 330 56-4) 4- (5-Chloromethyl-lH-imidazole-1-methylmethyl) -piperidine-1-carboxylic acid benzyl ester 9.9 g (30 g) mmol) of the compound prepared in Preparation 56-3) were dissolved in 50 ml of chloroform and therein were slowly added 7.1 g (60 mmol) of thionyl chloride at 0 ° C. The mixture was stirred for 2 hours. The solvent was distilled off under reduced pressure and the residual hydrochloric acid was removed in vacuo to obtain 9.9 g "(95% yield, weight 347.5) of the hydrochloric acid salt of the title compound. XH NMR (CDC13 ) d 1.12 (d, 2H), 1.53 (d, 2H), 2.65 (s, 2H), 3.82 (d, 2H), 4.22 (s, 2H), 4.42 (s, lH), 4.49 (s, 3H), 5.12 (s, 2H), 6.60 (s, lH), 7.30-7.41 (m, 5H) FAB (M + H ): 349 Preparation 57: Synthesis of 1- (4-chlorobenzyl) -5-chloromethyl-1H-imidazole 57-1) 1- (4-chlorobenzyl) -5-hydroxymethyl-1H-imidazole hydrochloride The title compound was obtained with a performance of 50% according to the procedure described in J. M. Dener, L-H Zhang, H. Rapoport, J. Org, Chem., 1993, 58, 1159, using a dihydroxyacetone dimer and 4-chlorobenzylamine hydrochloride as starting materials. X H NMR (CDCl 3 + CD 3 OD) d 4.46 (s, 2 H), 5.26 (s, 2 H), 7.00 (s, 1 H), 7.07 (d, 2 H), 7.50 (d, 2H), 7.65 (s, lH) 57-2) 1- (4-Chlorobenzyl) -5-chloromethyl-1H-imidazole hydrochloride The title compound was obtained in 96% yield according to a procedure similar to that used in Preparation 56-4), with the exception that the compound that was prepared in Preparation 57-1) was used as a starting material. This compound was used directly in the next reaction without purification. Preparation 58: Synthesis of 4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole 58-1) Nt-Butyl-N '- (naphthalen 1-methylmethyl) -hydrazine 5.0 g (32 mmol) of 1-naphthaldehyde and 3.99 g (32 mmol) of t-butylhydrazine hydrochloride were dissolved in 100 ml of methanol and then the mixture was reacted with 1 ml of acetic acid, at room temperature for 24 hours. After the solvent was distilled off under reduced pressure, 20 ml of ethyl acetate were added to the residue. The mixture was washed with a saturated solution of sodium hydrogen carbonate. Subsequently, the separated organic layer was dried in anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, in order to obtain 6.3 g (28 mmol, 86% yield) of the title compound. XH NMR (CDC13) d 1.70 (s, 9H), 7.23 (s, lH), 7.32 (m, lH), 7.42 (m, 2H), 7.80 (d, ÍH) , 7.90 (d, 2H), 8.60 (d, 1H), 9.91 (s, ÍH), 12, 1 (br, lH) FAB (M + H): 227 58-2) Ethyl ester of 1 - (t-Butyl) -3- (naphthalen-1-yl) -lH-pyrazole-4-carboxylic acid 6.3 g (28 mmol) of the compound prepared in Preparation 58-1) and 2.44 g ( 30.8 mmol) of ethyl propionate were dissolved in a solvent mixture of 27 ml of acetic acid and 32 ml of acetonitrile. The entire mixture was reacted to air for 3 days. The solvent was removed and the residue was subjected to column chromatography with silica gel (eluent: ethyl acetate / n-hexane = 9/1, v / v) to obtain 6.76 g (21 mmol, 75% yield). ) of the title compound. XH NMR (CDC13) d 0.80 (t, 3H), 1.65 (s, 9H), 3.98 (q, 2H), 7.38 (m, 2H), 7.48 (m, 1H) ), 7.55 (m, IH), 7.74 (m, lH), 7.85 • (m, 2H), 8.21 (s, lH), 11.31 (br, ÍH) FAB (M + H): 323 58-3) Ethylether of acid 3- (naphthalen-l - ± l) -lH- pyrazole-4-carboxylic acid 3.65 g (11.3 mmol) of the compound prepared in Preparation 58-2) were dissolved in 50 ml of formic acid and the resulting solution was boiled for 12 hours at reflux . The solvent present there was removed by distillation under reduced pressure and ethyl acetate was added. The mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was chromatographed column with silica gel (eluent: ethyl acetate / n-hexane = 6/4, v / v) to obtain 1.1 g (4.1 mmol, 37% yield) of the title compound (see, J). Hetero, Chem., 31, 1447, 1944).

XH NMR (CDCl 3) d 0.80 (t, 3H), 3.98 (q, 2H), 7.35-7.60 (m, 5H), 7.90 (m, 2H), 7.94 ( s, lH) FAB (M + H): 267 58-4) 3- (Naphthalen-1-yl) -lH-pyrazole-4-carboxylic acid 1.1 g (4.1 mmol) of the compound prepared in Preparation 58-3) and 2.1 g (12.4 mmol) of potassium hydroxide were dissolved in 50 ml of a mixture of methanol / water solvents (1: 1, v / v). The mixture was reacted under reflux for 12 hours. The solvent was removed by distillation under reduced pressure. The residue was acidified with an aqueous solution of IN hydrochloric acid, extracted with 50 ml of ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 910 mg (3.8 mmol, 92% yield) of the title compound. XH NMR (CD3OD + CDC13) d 7, 30 (m, 3H), 7.56 (d, ÍH), 7.80-7.95 (m, 3H), 8.07 (s, lH) FAB (M + H): 239 58-5) 4- [N- (2-Methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole 238 mg (1 mmol) of the compound prepared in Preparation 58-4) were dissolved ml of dimethylformamide. There, 230 mg (1.2 mmol) of EDC, 101 mg (l mmol) of triethylamine and 162 mg (1.2 mmol) of HOBT (1-hydroxybenzotriazole) were incorporated. Subsequently the mixture was stirred at 0 ° C for 5 minutes. To said mixture were added 124 mg (1 mmol) of N- (2-methoxyethyl) -N-methylamine hydrochloride, which was subsequently stirred at room temperature for 5 hours. The solvent was removed under reduced pressure. 10 ml of a saturated aqueous solution of potassium carbonate was added to the residue. The mixture was extracted with 20 ml of ethyl acetate, washed with 10 ml of an aqueous solution of IN hydrochloric acid, washed with a saturated solution of sodium chloride and water, dried over anhydrous sodium sulfate, and concentrated to obtain 247 mg (0.8 mmol, 80% yield) of the title compound. XH NMR (CDC13) d 2.40 (s, 2H), 2.81 (s, lH), 2.84 (s, lH), 2.96 (s, lH), 3.02 (s, 4H) , 3.15 (s, 1, 5H), 3.34 (s, 1, 5H), -7.24-7.52 (m, 4H), 7.59 (s, lH), 7.77 ( m, 2H), 7.93 (d, lH) FAB (M + H): 310 Preparation 59: Synthesis of 4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole 238 mg (1 mmol) of the compound prepared in Preparation 58-4) were dissolved in 10 ml of dimethylformamide and there 230 mg (1.2 mmol) of EDC and 162 mg (1.2 mmol) of HOBT were incorporated. The mixture was stirred at 0 ° C for 5 minutes. To the complete mixture 87 mg (1 mmol) of morpholino was added, which was subsequently stirred at room temperature for 5 hours. The solvent was removed under reduced pressure and 10 ml of a saturated aqueous potassium carbonate solution was added to the residue. The mixture was extracted with 20 ml of ethyl acetate, washed with 10 ml of an IN hydrochloric acid solution, washed with an aqueous solution of saturated sodium chloride and water, dried over anhydrous sodium sulfate and concentrated to a obtain 240 mg (0.8 mmol, 80% yield) of the title compound. XH NMR (CDCl 3) d 2.5 (br, 2H), 2.95 (br, 2H), 3.15 (br, 2H), 3.40 (br, 2H), 7.50 (m, 4H) 7.95 (m, 4H), 9.73 (br, 1H) FAB (M + H): 308 Example 152: Synthesis of 1- [1- (1-benzyloxycarbonyl-piperidin-4-ylmethyl) -lH- imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (152) 616 mg (2.0 mmol) of the compound prepared in Preparation 56-4) were dissolved in 10 ml of dimethylformamide. There 264 mg (6.6 mmol) of sodium hydride (60%) were added at 0 ° C and the whole mixture was stirred for 5 minutes. To this mixture was added 765 mg (2.2 mmol) of the compound prepared in Preparation 58-5) and the resulting mixture was stirred at room temperature for 5 hours. The solvent was distilled off under reduced pressure and 10 ml of water was added to the residue.

Subsequently, the mixture was extracted twice with 20 ml of ethyl acetate, dried over magnesium sulfate, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v). v) to obtain 930 mg (Yield 75%) of the title compound. X H NMR (CDCl 3) d 1.11 (m, 2 H), 1.37 (br, 1 H), 1.50 (br, 2 H), 2.35 (br, 1 H), 2.55 (br, 2 H) , 2.71 (br, ÍH), 2.90-3.21 (m, 7H), 3.35 (br, lH), 3.90 (br, 2H), 3.98 (d, ÍH), 4.50 (d, 1H), 5.02 (s, 2H), 5.10 (s, 2H), 7.21-7.40 (m, 6H), 7.41-7.60 (m, 4H), 7.70 (s, lH), 7.80 (s, lH), 7.95 (m, 2H), 8.13 (d, lH) FAB (M + H): 621 Example 153: Synthesis from 1- [1- (1-methoxycarbonylpiperidin-4-ylmethyl) -lH-imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (153) 153-1) 1 - [1 - (Piperidin-4-ylmethyl) -lH-imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl] carbamoyl- 3- (naphthalen-1-yl) -IH-pyrazole 227 mg (0.36 mmol) of the compound prepared in Example 152 were dissolved in methanol. There, 20 mg of palladium hydroxide carbon was added and subsequently, the mixture was reacted at 1 atm of hydrogen for 2 hours. After the reaction was completed, the mixture was filtered and the solvent was removed. The filtrate was subjected to column chromatography with silica gel (eluent: ammonia water / methanol = 15/85, v / v) to obtain 128 mg (0.26 mmol, yield 74%) of the title compound. XH NMR (CDC13) d 1.08 (s, 2H), 1.53 (m, 4H), 2.33 (s, 2H), 2.64 (br, 4H), 3.20 (m, 6H) , 3.31 (s, lH), 3.75 (d, 2H), 4.13 (m, 2H), 5.10 (s, 2H), 6.71 (s, lH), 7.11 ( s, lH), 7.30 (m, 9H), 7.74 (d, lH), 7.81 (d, lH), 7.90 (s, lH), 8.06 (d, lH) FAB (M + H): 486 153-2) 1 - [1 - (1-methoxycarbonylpiperidin-4-ylmethyl) -lH-imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -IH-pyrazole 30 mg (62 μmol) of the compound prepared in Example 153-1) were added to 2 ml of dichloromethane. There, 5.4 mg (6.9 μmol) of methyl chloroformate were incorporated through an injector and the mixture was stirred for 2 hours. The solvent was removed under reduced pressure and the residue was subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 80/20, v / v) to obtain 27.8 mg (5.3 μmol, yield 85 %) of the title compound. XH NMR (CDC13) d 1.11 (br, 2H), 1.33 (br, ÍH), 1.53 (br, 2H), 2.39 (s, 2H), 2.70 (br, 4H) , 2.90-3.20 (br, 6H), 3.32 (s, lH), 3.62 (s, 3H), 3.78 (d, 2H), 4.16 (m, 2H), 5.16 (s, 2H), 6.74 (s, lH), 7.10 (s, lH), 7.21-7.50 (m, 14H), 7.76 (d, lH), 7 , 84 (d, lH), 7.91 (s, lH), 8.07 (d, 1H) FAB (M + H): 545 Example 154: Synthesis of 1- [1- (4-bromobenzyl) -1H -imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (154) The compound. of the title was obtained with an 81% yield according to the same procedure as that carried out in Example 152, with the exception that the compound prepared in Preparation 32-2) and the compound prepared in Preparation 58 were used. -5). X H NMR (CDCl 3) d 2.41 (s, 2 H), 2.82 (s, 1 H), 2.85 (s, 1 H), 2.98 (s, 1 H), 3.04 (s, 4 H) , 3.17 (s, 1, 5H), 3.36 (s, 1, 5H), 5.11 (s, 2H), 5.21 (s, 2H), 6.95 (d, 2H), 7.25 (d, 2H), 7.35-7.60 (m, 5H), 7.64 (s, lH), 7.72 (s, lH), 7.81 (m, 2H), 8 , 11 (d, lH) FAB (M + H): 558 Example 155: Synthesis of 1- [1- (4-chlorobenzyl) -1H-imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (na talen-1-yl) -lH-pyrazole (155) The title compound was obtained in an 81% yield according to the same procedure carried out in Example 152, with except that the compound prepared in Preparation 57-2) and the compound prepared in Preparation 58-5 were used). XH NMR (CDC13) d 2.41 (s, 2H), 2.82 (s, lH), 2.85 (s, lH), 2.98 (s, lH), 3.04 (s, 4H) , 3.17 (s, 1, 5H), 3.36 (s, 1, 5H), 5.20 (s, 2H), 5.25 (s, 2H), 6.97 (d, 2H), 7.26 (d, 2H), 7.35-7.46 (m, 5H), 7.47 (s, lH), 7.58 (s, lH), 7.88 (m, 2H), 8 , 11 (d, lH) FAB (M + H): 514 Example 156: Synthesis of 1- [1- (4-cyanobenzyl) -1H-imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (156) The title compound was obtained in an 81% yield according to the same procedure as in the Example 152, with the exception that the compound prepared in Preparation 29-5) and the compound prepared in Preparation 58-5) were used. X H NMR (CDCl 3) d 2.41 (s, 2 H), 2.82 (s, 1 H), 2.85 (s, 1 H), 2.98 (s, 1 H), 3.04 (s, 4 H) , 3.17 (s, 1, 5H), 3.36 (s, 1, 5H), 5.20 (s, 2H), 5.31 (s, 2H), 6.99 (d, 2H), 7.26 (d, 2H), 7.35-7.46 (m, 5H), 7.48 (s, lH), 7.57 (s, lH), 7.89 (m, 2H), 8 , 12 (d, ÍH) FAB (M + H): 505 Example 157: Synthesis of 1- [1-methyl-lH-imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl ] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (157) The title compound was obtained in an 81% yield according to the same procedure as in Example 152, with the exception that used l-methyl-5-chloromethyl-1H-imidazole hydrochloride and the compound prepared in Preparation 58-5). XH NMR (CDC13) d 2.42 (br, 2H), 2.71 (br, 1H), 3.10 (br, 5H), 3.30 (br, 1H), 3.50 (s, 3H) , 5.17 (s, 2H), 6.69 (s, lH), • 7.09 (s, lH), 7.41 (m, 9H), 7.74 (d, lH), 7.83 (d, lH), 7.89 (s, lH), 8.05 ( d, lH) FAB (M + H): 404 Example 158: Synthesis of 1- [1- (1-benzyloxycarbonyl-piperidin-4-ylmethyl) -lH-imidazol-5-ylmethyl] -4- (morpholine-4-) il) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole (158) 612 mg (2.0 mmol) of the compound prepared in Preparation 59 were dissolved in 10 ml of dimethylformamide.

There 264 mg (6.6 mmol) of sodium hydride (60%) were added, at 0 ° C and the whole mixture was stirred for 5 minutes. To the mixture was added 765 mg (2.2 mmol) of the compound prepared in Preparation 56-4), which was then stirred at room temperature for 5 hours. The solvent was removed by distillation, under reduced pressure, and 10 ml of water was added to the residue. The resulting mixture was then extracted twice with 20 ml of ethyl acetate, dried in sulfate • 20 mg, concentrated and subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 90/10, v / v) to obtain 930 mg (Yield 75%) of the title compound. X H NMR (CDCl 3) d 1.11 (m, 2 H), 1.37 (br, 1 H), 1.50 (br, 2 H), 1.62 (br, lH), 2.35 (br, lH), 2.55 (br, 2H), 2.71 (br, lH), 3.14 (br, 2H), 3.35 ( br, 2H), 3.90 (br, 2H), 4.15 (m, 4H), 5.02 (s, 2H), 5.10 (s, 2H), 7.21-7.40 (m , 6H), 7.41-7.60 (m, 4H), 7.70 (s, lH), 7.80 (s, lH), 7.95 (m, 2H), 8.13 (d, lH) FAB (M + H): 619 Example 159: Synthesis of 1- [1- (1-methoxycarbonylpiperidin-4-ylmethyl) -lH-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-3 - (naphthalen-1-yl) -lH-pyrazole (159 ) 159-1) 1 - [1 - (Piperidin-4-ylmethyl) -lH-imidazol-5-ylmethyl] -4 - (morpholin-4-yl) carbonyl-3- (naphthalen-1 -yl) -IH- Pyra ol 227 mg (0.36 mmol) of the compound prepared in Example 158 were dissolved in methanol. There, 20 mg of palladium hydroxide carbon was incorporated and the mixture was reacted at 1 atm of hydrogen for 2 hours. After the reaction was completed, the mixture was filtered and the solvent there present was removed. The residue was subjected to column chromatography with silica gel (eluent: water of ammonia / methanol = 15/85, v / v) to obtain 120 mg (0.26 mmol, yield 74%) of the title compound. XH NMR (CDC13) d 1.06 (m, 2H), 1.43 (m, 3H), 2.36 (br, 5H), 2.41-3.79 (br, 13H), 3.78 ( d, 2H), 5.22 (s, 2H), 6.88 (s, lH), 7.12 (d, 2H), 7.26 (m, ÍH), 7.35 (m, 3H), 7.63 (s, lH), 7.75 (d, lH), 7.80 (d, lH), 7.93 (d, 1H) FAB (M + H): 484 159-2) 1 - [ 1 - (1-Methoxycarbonylpiperidin-4-ylmethyl) -1H-imidazol-5-ylmethyl] -4 - (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole 30 mg (62 μmol ) of the compound prepared in Example 159-1) were dissolved in 2 ml of dichloromethane. There 5.4 mg (6.9 μmol) of methyl chloroformate was added through an injector and the whole mixture was stirred for 2 hours. The solvent was removed under reduced pressure and the residue was subjected to column chromatography with silica gel (eluent: dichloromethane / methanol = 80/20, v / v) to obtain 27.8 mg (5.3 μmol, yield 85 %) of the title compound.

XH NMR (CDC13) d 1.05 (br, 2H), 1.32 (br, ÍH), 1.53 (br, 2H), 2.31-2.72 (m, 5H), 3.03-3.33 (m, 7H), 3.62 (s, 3H), 3.66 (m, 2H), 4, 13 (br, 2H), 5.12 (s, 2H), 6.71 (s, lH), 7.03 (s, lH), 7.14 (S, 1H), 7.24-7.43 (m, 5H), 7.74 (d, 1H), 7.82 (d, 1H), 8.10 (d, 1H) FAB (M + H): 543 Example 160: Synthesis of 1- [1- (4-bromobenzyl) -1H-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole (160) The title compound was obtained with an 81% yield according to the same procedure as that carried out in Example 152, with the exception that the compound prepared in Preparation 32-2) and the compound prepared in Preparation 59 were used. XH NMR (CDC13 ) d 2.35 (br, 2H), 2.80 (br, 2H), 3.15 (br, 2H), 3.35 (br, 2H), 5.29 (s, 2H), 5.31 (s, 2H), 7.00 (d, 2H), 7.20-7.35 (m, 3H), 7.40-7.60 (m, 4H), 7.72 (s, lH), 7.80 (s, lH), 7.90 (m, 2H), 8.01 (d, lH) FAB (M + H): 556 Example 161: Synthesis of 1- [1- (4-slorobenzyl) - 1H-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yD-1H-pyrazole (161) The title compound was obtained with an 81% yield according to the same procedure as in Example 152, with the exception that the compound prepared in Preparation 57-2) and the compound prepared in Preparation 59 were used. XH NMR ' (CDC13) d 2.35 (br, 2H), 2.80. (br, 2H), 3.15 (br, 2H), 3.35 (br, 2H), 5.29 (s, 2H), 5.31 (s, 2H), 7.00 (d, 2H) , 7.20-7.35 (m, 3H), 7.40-7.60 (m, 4H), 7.72 (s, lH), 7.80 (s, lH), 7.90 (m , 2H), 8.01 (d, ÍH) FAB (M + H): 512 Example 162: Synthesis of 1- [1- (4-cyanobenzyl) -1H-imidazol-5-ylmethyl] -4- (morpholine- 4-yl) carbonyl-3- (naphthalen-1-yD-1H-pyrazole (162) The title compound was obtained in an 81% yield according to the same procedure performed in Example 152, with the exception of that the compound prepared in Preparation 29-5) and the compound prepared in the Preparation 59. XH NMR (CDCl 3) d 2.35 (br, 2H), 2.80 (br, 2H), 3.15 (br, 2H), 3.35 (br, 2H), 5.28 (s) , 2H), 5.34 (s, 2H), 7.03 (d, 2H), 7.20-7.35 (m, 3H), 7.40-7.60 (m, 4H), 7, 72 (s, lH), 7.80 (s, lH), 7.90 (m, 2H), 8.01 (d, lH) FAB (M + H): 503 Example 163: Synthesis of 1- (1 -methyl-lH-imidazol-5-ylmethyl) -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole (163) The title compound was obtained in a yield 81 % according to the same procedure as in Example 152, with the exception that l-methyl-5-chloromethyl-lH-imidazole hydrochloride and the compound prepared in Preparation 59 were used. XH NMR (CDCI3) d 2.35 (br, 2H), 2.80 (br, 2H), 3.15 (br, 2H), 3.35 (br, 2H), 3.62 (s, 3H), 5.29 (s) , 2H), 7.20-7.35 (m, 3H), 7.40-7.60 (m, 2H), 7.72 (s, lH), 7.80 (s, lH), 7, 90 (m, 2H), 8.01 (d, ÍH) FAB (M + H): 402 * Experimental Example 1 In vitro analysis of the inhibitory activity for Ras farnesyl transferase In the present experiment, the transferase was used a farnesil of Ras produced by genetic recombination techniques, according to the improved method of Pompliano (Pompliano et al., Biochemistry, 1992, 31, 3800) and Ras substrate protein (Ras-CVLS), which was described in Korean Patent Application No. 97-14409, was used after its purification, in accordance with the known method (see, Chung et al., Biochimica et Biophysica Acta, 1992, 278, 1129). The enzymatic reaction was carried out in 50μl of a 50mM sodium HEPES buffer solution, which contained 25mM potassium chloride, 25mM magnesium chloride, 10mM DTT and 50 μM zinc chloride. 1.5 μM of Ras substrate protein, 0.15 μM tritium-farnesyl-pyrophosphate and 4.5 nM farnesyl transferase were used. More specifically, in the initial step, the farnesyl transferase was incorporated into the aforementioned buffer solution. The reaction was maintained for 30 minutes at 37 ° C and then the said reaction was stopped by the addition of 1 ml of ethanol solution, which contained ÍM HCl. The formed precipitates were adsorbed on the GF / B filter, using a Hopper manifold (Hopper #FH 225V) for binding to the filter, washed with ethanol and then the radioactivity of the dry filter was measured using an LKBβ counter. The enzymatic titration was measured in the unsaturated state of the substrate, where the concentrations of the Ras substrate protein and farnesyl transferase had a quantitative relationship. The compound according to the present invention, dissolved in dimethyl sulfoxide (DMSO) was incorporated into the reaction solution in an amount less than 5% of the total reaction solution. Subsequently, the inhibitory activity of the enzymes thereof was calculated. The inhibitory activity of the enzymes was represented as a comparison between the percentage of the amount of farnesyl incorporated into the Ras substrate protein, in the presence of the test compound and in the absence of the test compound. The IC50 of the test compound was defined as the concentration at which 50% of the epi- gem activity is inhibited. To evaluate the selective inhibitory activity of the enzymes of the compound according to the present invention, the inhibitory activity on the transferase of geranylgeranyl was measured. Geranylgeranyl transferase was purified from the brain of a bovine, according to the modified Schaber's method (Schaber et al., J. Biol. Chem. 1990, 265, 14701) and substantially the same experimental procedure was carried out. performed for the farnesyl transferase in the geranylgeranyl phosphate and the Ras-CVIL substrate protein. The results of the test are shown in the following Table 7. Experimental Example 2 In vivo analysis of the inhibitory activity for ras farnesyl transferase In the present experiment, the Rat2 cell line, which expresses the C-Harvey protein, was used. Ras, which has a transforming activity and the cell line Rat2 (Korean Patent Application No. 97-14409), which is transformed with the fused protein of H-Ras substituted with a polybasic lysine domain in the C-terminus of K-Ras. The experiment was carried out using the modified method of Declue's (Declue, J. E. et al., Cancer Research, 1991, 51, 712). The experimental method will be described in more detail below. 3 x 105 cells of the transformed Rat2 fibroblast cell line were sprayed on a 60 mm cell culture plate and cultured for 48 hours in a cell incubator at 37 ° C. After reaching 50% of the density or more, they were treated with the test compounds. The compound according to the present invention, dissolved in dimethyl sulfoxide (DMSO), was used. A concentration of 1% methyl sulfoxide was used both in the control and in the test groups. Four hours after starting the treatment with the compound, methionine was added, labeled with 150 μCi of the radioactive isotope [35S] per 1 ml of the medium. After a culture that extended for 20 hours, the cells were washed with water of physiological saline. The cells were lysed with 1 ml of a cold cell lysis buffer solution (50 mM HEPES sodium buffer solution, which contained 5 mM magnesium chloride, 1 mM DTT, 1% NP 40, 1 mM EDTA, 1 mM PMSF, 2 μM of leupeptin, 2 μM of pepstatin A and 2 μM of analgesic) and the supernatant was obtained in which the cells were lysed through a high-speed centrifugation of 12,000 g × 5 minutes. The amount of radioisotope in the supernatant was measured and standardized to obtain the quantitative result in the immunoprecipitation reaction. Subsequently, Y13-259, a monoclonal antibody that binds specifically to Ras protein (Furt, M. E. et al., J. Virol, 1982, 43, 294) was added and reacted for 15 hours at 4 ° C. A suspension of protein A (combined with goat anti-murine immunoglobulin antibody) was added to the solution and reacted for 1 hour at 4 ° C. Then, in order to eliminate the non-specific binding product, the immunoprecipitates were washed with a buffer solution (50mM Tris-chloride buffer solution containing 50mM sodium chloride, 0.5% sodium dioxycholate, 0.5% of NP 40 and 0.1% SDS). The precipitates were incorporated into a buffer solution for electrophoresis, boiled and then electrophoresed using 13.5% SDS polyacrylamide gel. Once the electrophoresis was finished, the gel was fixed and dried. Then, said gel was exposed to an X-ray film, revealed and printed. Based on the results of the experiment, the protein band intensities combined with or without Ras farnesyl protein were calculated and the concentration of the test compound that inhibited 50% of the farnesyl binding was defined as CIC50, an activity Inhibitor of ras farnesyl transferase in vivo. The results of the test are presented in the following Table 7.

TABLE 7-1 • TABLE 7-1 Table 7-2 • Table 7-3 • 223 Table 7-4 • Table 7-5 Table 7-6 Table 7-7 • • Table 7-8

Claims (12)

CLAIMS 1. An imidazole derivative compound, characterized in that it is represented by formula (1) which is detailed below: [Formula 1] wherein: ni represents an integer ranging from 1 to 4, A represents hydrogen, Ci-Cio straight or branched chain alkyl which may be optionally substituted by C3-C cycloalkyl or lower alkoxy; or a radical that is selected from the following group: where: R? And Ri '/ independently from each other, represent hydrogen, halogen, cyano, nitro, hydroxycarbonyl, aminocarbonyl, aminothiocarbonyl, lower alkoxy, phenoxy, phenyl, benzyloxy, or lower alkyl which may be optionally substituted by, C3-C6 cycloalkyl, R2 represents hydrogen or lower alkyl, or represents -EF, where E is -CH2-, -C (O) or -S (0) 2- and F is hydrogen; lower alkyl which may be optionally substituted by phenoxy or biphenyl; lower alkoxy which may be optionally substituted by aryl; phenyl; benzyl; benzyloxy; or amino which may be optionally substituted by lower alkyl, benzyl or C5-C6 cycloalkyl, R3 represents hydrogen, alkyl or lower phenyl,
1. R4 represents a radical selected from the group indicated below: where: n2 and n3, independently of each other, denote 0, 1, 2, 3 or 4, R5 and Rg, independently of each other, represent hydrogen, lower alkyl, lower alkoxy, phenoxy, phenyl, hydroxy or halogen, Re and Rß. independently of one another, they represent hydrogen, lower alkyl, lower alkoxy, phenoxy, phenyl, cyano, hydroxy or halogen, R7 represents hydrogen, lower alkyl which may be optionally substituted by C3-Cd cycloalkyl; lower alkoxy; hydroxy; C3-C6 cycloalkyl; di (lower alkyl) amino; phenyl; phenoxy; or halogen, Rio represents hydrogen, lower alkyl or lower alkoxy, Y represents a radical selected from the group indicated below: wherein: X represents O or S, B represents hydrogen or lower alkyl which may be optionally substituted by hydroxy, mercapto, lower alkoxy, lower alkylthio or aryl, C represents hydrogen or lower alkyl which may be optionally substituted by aryl; or represents a radical selected from the group indicated below: where Ru and R12 # independently from each other, represent hydrogen, lower alkyl, lower alkoxy, halogen, cyano, hydroxycarbonyl, amino, carbonyl, aminothiocarbonyl, hydroxy, phenyl or phenoxy, R13 and R? , independently of each other, represent hydrogen, lower alkyl, aryl or -Hntorx-R « where X is defined as described above, n is an integer ranging from 2 to 4 and R15 is lower alkyl, D represents an amino acid residue or lower alkyl ester of an amino acid residue; or represents a radical that is selected from the following group: where: Rio is defined according to what was described above, Q represents O, S, S = 0 or S02, Z represents O, S, S = 0, S02, C = 0 or C = S, or represents CH-R2o or N-R20 (where R2o is hydrogen, lower alkyl or hydroxy), n5 denotes an integer ranging from 1 to 3, Rie and Ri7, independently of each other, represents hydrogen; aryl, lower alkyl that can be • optionally substituted by aryl or cyanoaryl; or CCH_) pr-Q-K where n4, Q and R10 are defined as described above, Ris and Ri9 independently of each other, represent hydrogen; halogen; hydroxy; cyano; lower alkyl; lower alkoxy; alkoxyalkyl; alkylthio; hydroxycarbonyl; • aminocarbonyl; aminothiocarbonyl; alkylsulfonyl; alkylthioalkyl; alkylthioalkyloxy; aril; or oxy, thio, sulfonyl or lower alkyl substituted by aryl, G represents a radical selected from the group indicated below: where: Rn and R? 2 are defined as described above, I represents lower alkoxy or represents a radical selected from the following group: 25 where Ri6. 17 and Z are defined as described above, L represents a radical selected from the following group: where Z and Q are defined as described above, provided that (1) n2 is different-from 0 when R3 is hydrogen, and [2) And it's different from when A is or a pharmaceutically acceptable salt or isomer thereof.
2. 2 . The compound according to claim 1, characterized in that: ni represents an integer 'ranging from 1 to 3, A represents hydrogen; Ci-Cio straight or branched chain alkyl which may be optionally substituted by C3-C7 cycloalkyl or lower alkoxy; or a radical that is selected from the group that is included below: Docum e nto y ^ c-r-o lo ^ t • where: RI and Ri 'independently from each other, represent hydrogen, halogen, cyano, nitro, hydroxycarbonyl, aminocarbonyl, aminothiocarbonyl, lower alkoxy, phenoxy, Phenyl, benzyloxy, or lower alkyl which may be optionally substituted by C3-C6 cycloalkyl, R2 represents hydrogen or lower alkyl, or represents -EF, where E is -CH2-, -C (0) or -S (0) 2 - and F is hydrogen; lower alkyl which may be optionally substituted by phenoxy or biphenyl; lower alkoxy which may be optionally substituted by aryl; phenyl; benzyl; benzyloxy; or amino which may be optionally substituted by lower alkyl, benzyl or. C5-C6 cycloalkyl, R3 represents hydrogen or lower alkyl, R4 represents a radical selected from the group indicated below: where: n2 and n3, independently of each other, denote 0, 1, 2, 3 or 4, R5, R6, Rs and 9. independently of each other, • represent hydrogen, lower alkyl, lower alkoxy, hydroxy or halogen, R7 represents hydrogen, lower alkyl which may be optionally substituted by C3-C6 cycloalkyl; lower alkoxy; hydroxy; C3-C6 cycloalkyl; or halogen, Rio represents hydrogen, methyl or methoxy; And represents a radical selected from the group indicated below: Where: X represents O or S, B represents hydrogen or lower alkyl which may be optionally substituted by lower alkoxy or aryl, C represents hydrogen or lower alkyl which may be optionally substituted by aryl; or represents a radical selected from the group indicated below: where Rn and Ri2, independently of each other, represent hydrogen, lower alkyl, lower alkoxy, halogen, cyano, aminocarbonyl, phenyl or phenoxy, R13 and i4, independently of each other, represent hydrogen, lower alkyl, aryl where X is defined as described above, n is 2 and Ri5 is lower alkyl, D represents an amino acid residue or lower alkyl ester of an amino acid residue; or represents a radical that is selected from the following group: where: Rio is defined according to what was described above, Q represents 0, S, S = 0 or S02, • Z represents O, S, S = 0, S02 or C = 0, or represents CH-R2o or N-R20 (where R20 is hydrogen, lower alkyl or hydroxy), ns denotes an integer ranging from 1 to 3, R16 and Ri7, independently of each other, represent hydrogen; aryl, lower alkyl which may be optionally substituted by aryl or cyanoaryl; or flMt? fi-Q-B. Where n4, Q and R10 are defined as described above, Ris and R19. independently of each other, they represent hydrogen; halogen; hydroxy; cyano; lower alkyl; lower alkoxy; alkoxyalkyl; alkylthio; hydroxycarbonyl; aminocarbonyl; aminothiocarbonyl; alkylsulfonyl; Alkylthioalkyl; alkylthioalkyloxy; aril; or oxy, thio, sulfonyl or lower alkyl substituted by aryl, G represents a radical selected from the group indicated below: where: Rii and R12 are defined as described above, I represents lower alkoxy or represents a radical selected from the following group: where: Ri6. 17 and Z are defined as described above, L represents a radical selected from the following group: where Z and Q are defined as described above, provided that (1) n2 is different from 0 when R3 is hydrogen, and (2) Y is different from when A is
3. 3. The compound, according to claim 1, characterized in that Y represents and C represents
4. 4. The compound according to claim 1, characterized in that it is selected from the group consisting of: 3- [N- (2-methoxyethyl) -methyl] carbamoyl-1- [1- (3,4-methylene-dioxybenzyl) ) -lH-imidazol-5-ylmethyl] -4- (naphthalen-1-yl) -1H-pyrrole (1), 1- [1- (3,4-methylenedioxybenzyl-1H-imidazol-5-ylmethyl) -3 - (morphin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (2), 1- [1- (3,4-methylenedioxybenzyl-1H-imidazol-5-ylmethyl) -3 - (4-methyl-piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) '- lH-pyrrole (3), 3 { N- [2- (N, N-dimethylamino) ethyl] - N-methyl.}. Carbamoyl-1- [1- (3, -methylenedioxybenzyl-1H-imidazol-5-ylmethyl] -4- (naphthalen-1-yl) -lH-pyrrole (4), 3- [N-] (2-methoxyethyl) -N-methyl] carbamoyl-4-naphthalen-1-yl) -1- [1-naphthalen-1-ylmethyl) -lH-imidazoI-5-ylmethyl] -lH-pyrrole (5), 3 - (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -1- [1-naphthalen-1-ylmethyl) -lH-imidazol-5-ylmethyl] -1H-pyrrole (6), 3- (4-methylpiperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -1- [1 - (naphthalen-1-yl-methyl) -lH- imidazol-5-yl-methyl] -lH-pyrrole (7), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- ((R) -a-methylbenzyl-1H-imidazole -5-ylmethyl] -4- (naphthalen-1-yl) -lH-pyrrole (8), 1- [1- ((R) -a-methylbenzyl-1H-imidazol-5-ylmethyl] -3- (morfol in-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (9), 1- [1- ((R) -a-methylbenzyl-1H-imidazol-5-ylmethyl] -3- (4-methyl-piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (10), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [ 1- ((S) -a-methyl-benzyl-lH-imidazol-5-ylmethyl] -4- (naphthalen-1-yl) -lH-pyrrole (11) 1- [1- ((S) -a-methylbenzyl-lH-imidazol-5-ylmethyl] -3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (12) , 1- [1- ((S) -a-methylbenzyl-1H-imidazol-5-ylmethyl] -3- (4-methylpiperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (13), 3- [N- (2-methoxyethyl) -N-methyl] carbamoy1-4- (naphthalen-1-yl) -1- [1- (phenethyl) -lH-imidazol-5-ylmethyl] -lH-pyrrole (14 ), 3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -1- [1- (phenethyl) -lH-imidazol-5-ylmethyl] -lH-pyrrole (15), 3- (4-methyIpiperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -1- [1 - (phenethyl) -lH-imidazol-5-ylmethyl) -lH-pyrrole (16), 3- [N - (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- (2-methoxy) phenethyl-lH-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -lH-pyrrole (17 ), 1- [1- (2-methoxy) phenethyl-1H-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (18), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- (4-methoxy) phenethyl-lH-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -lH -pyrrole (19), 1- [1- (4-methoxy) phenethyl-1H-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (20), 1- [1- (2-fluo) phenethyl-lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH -pyrrole (21) 1- [1- (2-fluo) phenethyl-lH-imidazol-5-yl] methyl-3- [4-methyl-piperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (22), 1- [1- (2-chloro) phenethyl-lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1- il) -lH-pyrrole (23) l- [l- (2-chloro) phenethyl-lH-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1) -yl) -lH-pyrrole (24), 1- [1- (3-Chloro) phenethyl-1H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH -pyrrole (25) 1- [1- (3-chloro) phenethyl-1H-imidazol-5-yl] ethyl-3- [4-methyl-piperazin-1-yl] carbonyl-4- (naphthalen-1-yl) ) -lH-pyrrole (26), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -1- [1- (3-phenyl) propyl-1H- imidazol-5-yl] ethyl-lH-pyrrole (27) 3- [4-methylpiperazin-1-yl] carbonyl-4-naphthalen-1-yl) -1- [1- (3-phenyl) propyl-1H- imidazol-5-yl] methyl-lH-pyrrole (28), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -l- [l- (naphthalene- 2-yl) methyl-lH-imidazol-5-yl] methyl-1H-pyrrole (29), 3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -l- [l -naphthalen-2-yl) methyl-lH-imidazol-5-yl] methyl-lH-pyrrole (30) 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -1-. { 1- [2- (naphthalen-1-yl) ethyl] -lH-imidazol-5-yl} methyl-lH-pi rrol (31), 3- [4-methyIpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -1-. { 1 [2- (naphthalen-1-yl) ethyl] -lH-imidazol-5-yl} methyl-lH-pyrrole (32), 1- [1- (4-bromo) phenethyl-1H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH -pyrrole (33) 1- [1- (4-Bromo) phenethyl-lH-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -IH-pyrrole (34 ), 1- [1- (4-fluo) phenethyl-lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH -pyrrole (35) 1- [1- (4-fluo) phenethyl-1H-imidazol-5-yl] methyl-3- [4-methyl-piperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (36), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- [1- (4-methyl) phenethyl-1H-imidazol-5-yl] methyl-4- (naphthalen-1- il) -lH-pyrrole (37), 1- [1- (4-methyl) phenethyl-1H-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalene- 1-yl) -IH-pyrrole (38), 1- [1- (4-chloro) phenethyl-1H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH -pyrrole (39) 1- [1- (4-chloro) phenethyl-1H-imidazol-5-yl] methyl] -3- [4-methyl-piperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH- pyrrole (40), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -1-. { 1- [2- (naphthalen-2-yl) ethyl] -lH-imidazol-5-yl} methyl-1H-pi-rrol (41), 3- [4-methyl-piperazin-1-yl] -carbonyl-4- (naphthalen-1-yl) -l-. { 1 - [2- (Naphthalen-2-yl) ethyl] -lH-imidazol-5-yl} methyl-lH-pyrrole (42) 1- [1- (4-hydroxy) phenethyl-lH-imidazol-5-yl] methyl-3- [4-methylpiperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (43 ), 1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (thiophen-2-yl) carbonyl-lH-pyrrole (44), 1- (1H-imidazole-4) il) methyl-4- (naphthalen-1-yl) -3- (thiophen-3-yl) carbonyl-lH-pyrrole (45), 3-benzoyl-l- (lH-imidazol-4-yl) methyl-4 - (naphthalen-1-yl) -1 H -pyrrole (46), 3- (2-bromobenzoyl) -1- (1 H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (47), 3- (3-bromobenzoyl) -1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (48), 3- (4-bromobenzoyl) - 1- (1H-imidazol-4-yl) ethyl-4- (naphthalen-1-yl) -lH-pyrrole (49), 1- (1H-imidazol-4-yl) methyl-3- (2-methylbenzoyl) -4- (naphthalen-1-yl) -lH-pyrrole (50), 1- (1H-imidazol-4-yl) methyl-3- (3-methylbenzoyl) -4- (naphthalen-1-yl) -lH -pyrrole (51), 1- (1H-imidazol-4-yl) methyl-3- (4-methylbenzoyl) -4- (naphthalen-1-yl) -lH-pyrrole (52), 1- (1H-imidazole -4-yl) methyl-3- (3-methoxybenzoyl) -4- (naphthalen-1-yl) -lH-pyrrole (53), 1- (1H-imidazol-4-yl) methyl-3- (4- methoxybenzoyl) -4- (naphthalen-1-yl) -lH-pyrrole (54), 3- (2-chlorobenzoyl) -1- (lH-imidazole-4 -yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (55), 3- (4-chlorobenzoyl) -1- (1H-imidazol-4-yl) methyl-4- (naphthalene -1- il) -lH-pyrrole (56), 3- (2,4-dichlorobenzoyl) -1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (57), 3- (4-Fluobenzoyl) -1- (IH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (58), 3- (2,4-difluobenzoyl) -1- (lH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (59), 3- (4-cyanobenzoyl) -1- (lH-imidazol-4-yl) methyl-4 - (naphthalen-1-yl) -lH-pyrrole (60), 1- (1H-imidazol-4-yl) methyl-3- (4-methylthiomethyl-benzoyl) -4- (naphthalen-1-yl) -lH -pyrrole (61), 1- (1H-imidazol-4-yl) methyl-3- [4- (2-methylthioethyl) benzoyl] -4- (naphthalen-1-yl) -lH-pyrrole (62), 1 - (1H-imidazol-4-yl) methyl-3- [4- (2-methylthioethoxy) benzoyl] -4- (naphthalen-1-yl) -lH-pyrrole (63), 1- (1H-imidazole-4) -yl) methyl-3- (3-methylthiomethyl-benzoyl) -4- (naphthalen-1-yl) -lH-pyrrole (64), 1- (1H-imidazol-4-yl) methyl-4- (naphthalene- 1-yl) -3- (3-phenyl-benzoyl) -lH-pyrrole (65), 1- (1H-imidazol-4-yl) methyl-4 - (naphthalen-1-yl) -3- (4-phenyl-benzoyl) -IH-pyrrole (66), 1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3 - (4-phenoxy-benzoyl) -lH-pyrrole (67), 3- (4-benzylbenzoyl) -1- (lH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (68), 1- (lH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (naphthalen-1-yl) carbonyl-lH-pyrrole (69), 1- (lH- imidazol-4-yl) methyl-3- (4-methylbenzoyl) -4 - (N-methyl-indol-3-yl) -lH-pyrrole (70), 5-n-butyl-3- (2,4-dichlorobenzoyl) -1- (lH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -IH-pyrrole (71), 5-benzyl -3- (2,4-dichlorobenzoyl) -1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (72), 1- [1- (4-cyanobenzyl) -lH-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -3- (thiophen-2-yl) carbonyl-lH-pyrrole (73), 1- [1- (4-cyanobenzyl-1H -imidazol-5-yl] methyl-4- (naphthalen-1-yl) -3- (thiophen-3-yl) carbonyl-lH-pyrrole (74), 3-benzoyl-l- [1- (4-cyanobenzyl -lH-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -lH-pyrrole (75), 3- (3-bromobenzoyl) -1- [1- (4-cyanobenzyl-1H-imidazole- 5-yl] methyl-4- (naphthalen-1-yl) -lH-pyrrole (76), 3- (4-bromobenzoyl) -1- [1- (4-cyanobenzyl-1H-imidazol-5-yl] methyl -4- (naphthalen-1-yl) -lH-pyrrole (77), 3- (4-fluobenzoyl) -1- (l-methyl-lH-imidazol-4-yl) methyl-4- (naphthalen-1- il) -lH-pyrrole (78), 1- (1-methyl-1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (4-phenoxybenzoyl) -lH-pyrrole (79 ), (S) -1- (1H-imidazol-4-yl) methyl-3- [N- (1-methoxycarbonyl-3-methylthio) propyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (80), (S) -3- [N- (l-hydroxycarbonyl-3-methylthio) propyl] carbamoyl-1- (lH-imidazole-4-) il) methyl-4- (naphthalen-1-yl) -1H-pyrrole (81), 1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (N-phenyl) -carbamoyl) -lH-pyrrole (82), 3- (N-benzylcarbamoyl) -1- (lH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (83), 1 - (lH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (piperidin-1-yl) carbonyl-lH-pyrrole (84), 1- (1H-imidazol-4-yl) ) methyl-3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (85), 1- (lH-imidazol-4-yl) methyl-4- (naphthalen-1) -yl) -3- (thio-morpholin-4-yl) carbonyl) -lH-pyrrole (86), 1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (S, S-dioxothiomorpholin-4-yl) carbonyl-lH-pyrrole (87), 1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (piperazin-1-) il) carbonyl-lH-pyrrole (88), 1- (lH-imidazol-4-yl) methyl-3- (4-methylpiperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (89), 1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (thiazolidi) n-3-yl) carbonyl-lH-pyrrole (90), 3- (4-hydroxypiperidin-l-yl) carbonyl-1- (lH-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (91), 1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -3- (4-oxo-piperidin-1-yl) carbonyl-lH-pyrrole ( 92), 3-N- (2-hydroxyethyl) carbamoyl-1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -IH-pyrrole (93), 3- [N- ( 2-hydroxyethyl) -N-methyl] carbamoyl-1- (1H-imidazol-4-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (94), 1- (1H-imidazole-4-) il) methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (95), 1- (1H-imidazol-4-yl) methyl -3- (morpholin-4-yl) carbonyl-4- (quinolin-4-yl) -lH-pyrrole (96), 4- (1,2-dihydroacenaphthylene-5-yl) -1- (lH-imidazol- 4-yl) methyl-3- (morpholin-4-yl) carbonyl-lH-pyrrole (97), 3-N- (4-cyanobenzylcarbamoyl-1- (lH-imidazol-4-yl) methyl-4- (naphthalene -1-yl) -lH-plrrol (98), 1- (l-methyl-lH-imidazol-5-yl) methyl-3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (99), (S) -1- [1- (4-cyanobenzyl-lH-irrtidazol-5-yl] m ethyl-3- [N- (1-methoxycarbonyl-3-methylthio) propyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (100), (S) -1- [1- (4-cyanobenzyl -lH-imidazol-5-yl] methyl-3- [N- (1-hydroxycarbonyl-3-methylthio) propyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (101), (S) - 1- [1- (4-Cyanobenzyl-lH-imidazol-5-yl] methyl-3- [N- (1-methoxycarbonyl-3-methyl) butyl] carbamoyl-4- (naphthalen-1-yl) -1H- pyrrole (102), (S) -1- [1- (4-cyanobenzyl-1H-imidazol-5-yl] methyl-3- [N- (1-hydroxycarbonyl-3-methyl) butyl] carbamoyl-4- ( naphthalen-1-yl) -1H-pyrrole (103), 1- [1- (4-cyanobenzyl-1H-imidazol-5-yl] methyl-3- (orpholin-4-yl) carbonyl-4- (naphthalene- 1-yl) -lH-pyrrole (104), 1- [1- (4-cyanobenzyl-lH-imidazol-5-yl] methyl-3- (4-methyl-pi? Erazin-1-yl) carbonyl-4 - (naphthalen-1-yl) -IH-pyrrole (105), 1- [2- (lH-imidazol-1-yl) ethyl] -3- (morpholin-4-yl) carbonyl-4- (naphthalen-1) -yl) -lH-pyrrole (106), (S) -1- [3- (1H-imidazol-4-yl) propyl] -3- [N- (1-methoxy-carbonyl-3-methylthio) propyl] carbamoyl-4- (naphthalen-1-yl) -1H-pyrrole (107), (S) -3- [N- (l-hydroxycarbonyl-3-methylthio) propyl] carbamoyl-1- [3- (lH-imidazol-4-yl) propyl] -4- (naphthalen-1-yl) -lH-pyrrole (108), 1- [3- (1H-imidazol-4-yl) propyl] -3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -IH-pyrrole (109), 1- [1 - (4-Cyanobenzyl-lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (110), 1- [1- (4-bromobenzyl-lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (111), 1- [1- (4-bromobenzyl-1H-imidazol-5-yl] methyl-3- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (112 ), 1- [1- (4-cyanobenzyl-1H-imidazol-5-yl] methyl-3- (morpholin-4-yl) thiocarbonyl-4- (naphthalen-1-yl) -lH-pyrrole (113), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1- (1-methyl-lH-imidazol-5-yl) methyl-4- (naphthalen-1-yl) -lH-pyrrole (114) 1- (l-Isobutyl-lH-imidazol-5-yl) ethyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (115 ), 1- (1-cyclohexylmethyl-1H-imidazol-5-yl) methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole ( 116), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1) -yl) -1- (l-pentyl-lH-imidazol-5-yl) methyl-lH-pyrrole (117), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalene- 1-yl) -1- (l-octyl-lH-imidazol-5-yl) methyl-lH-pyrrole (118), 1- (l-decyl-lH-im? Dazol-5-yl) methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (119), 3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-1 - [1- (3-methyl-butyl) -lH-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -lH-pyrrole (120), 1- [1- (2-methoxyethyl) - lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (121), 3- [N- ( 2-methoxyethyl) -N-methyl] carbamoyl-1- [1- (3-methoxy-propyl) -lH-imidazol-5-yl] methyl-4- (naphthalen-1-yl) -lH-pyrrole (122) 1- [1- (3-ethoxypropyl) -lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH -pyrrole (123), 1- [1- (3-isopropoxypropyl) -lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1) -yl) -1H-pyrrole (124), 1- [1- (4-bromobenzyl-1H-imidazol-5-yl] methyl-3- [4-methyl-pipera] zin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (125), 1- [1- (4-chlorobenzyl-1H-imidazol-5-yl] methyl-3- [4- methyl-piperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (126), 1- [1- (4-fluobenzyl-lH-im? dazol-5-yl] methyl-3 - [N- (2-methoxy-ethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (127), 1- [1- (4-fluobenzyl-1H-imidazole-5 -yl] methyl-3- [4-methyl-piperazin-1-yl] carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (128), 1- [1- (4-methoxy-benzyl-1H-imidazole -5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -IH-pyrrole (129), 1- [1- (4-methoxybenzyl -lH-imidazol-5-yl] methyl-3- (4-methyl-piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (130), 1- [1- (3 -chlorobenzyl-lH-imidazol-5-yl] methy1-3- (4-methyl-piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (131), 1- [1- (3-chlorobenzyl-lH-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (132), 1 - [1- (2-chlorobenzyl-lH-imidazol-5-yl] methyl-3- (4-methyl-piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (133), 1- [1- (2-chlorobenzyl-1H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) - N-methyl] carbamoyl-4- (naphthalen-1-yl) -lH-pyrrole (134), 1- [1- (2-fluobenzyl-1H-imidazol-5-yl] methyl-3- (4-methyl- piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (135), 1- [1- (4-methylbenzyl-1H-imidazol-5-yl] methyl-3- (4- methyl-piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -IH-pyrrole (136), 1- [1- (4-methylbenzyl-1H-imidazol-5-yl] methyl-3- ( morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (137), 1- [1- (3-methylbenzyl-1H-imidazol-5-yl] methyl-3- (4- methyl-piperazin-1-yl) carbonyl-4- (naphthalen-1-yl) -lH-pyrrole (138), 1- [1- (4-cyanobenzyl-1H-imidazol-5-yl] methyl-3- ( naphthalen-1-yl) carbonyl-lH-pyrrole (139), 1- [1- (4-bromobenzyl-1H-imidazol-5-yl] ethyl-3- (naphthalen-1-yl) carbonyl-lH-pyrrole ( 140), 1- [1- (4-bromobenzyl-1H-imidazol-5-yl] methyl-3- [N- (2-methoxyethyl) -N-methyl] carbamoyl-4- (naphthalen-1-yl) carbonyl -lH-pi rrol (141), 4-ethoxycarbonyl-2- (lH-imidaz) ol-5-ylmethyl) -5- (naphthalen-1-yl) oxazole (142)2- (lH-imidazol-5-ylmethyl) -4- (morpholin-4-yl) carbonyl-5- (naphthalen-1-yl) oxazole (143), 4-ethoxycarbonyl-2- (lH-imidazole-5) -ylmethyl) -5- (naphthalen-1-yl) thiazole (144), 2- [1- (4-chlorobenzyl-lH-imidazol-5-ylmethyl] -4-methoxy-carbonyl-5- (naphthalen-1- il) thiazole (145), 2- [1- (4-chlorobenzyl-lH-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-5- (naphthalen-1-yl) thiazole (146) 2- [1- (4-chlorobenzyl-lH-imidazol-5-ylmethyl] -4- [N- (2-methoxy) ethyl-N-methylcarbamoyl] -5- (naphthalen-1-yl) thiazole (147) , 2- [1- (4-chlorobenzyl-lH-imidazol-5-ylmethyl] -5-methoxy-carbonyl-4- (naphthalen-1-yl) thiazole (148), 2- [1- (4-chlorobenzyl- lH-imidazol-5-ylmethyl] -5- (morpholin-4-yl) carbonyl-4- (naphthalen-1-yl) thiazole (149), 2- { 1- [1- (benzyloxycarbonyl) piperidin-4 -ylmethyl] -1H-imidazol-5-ylmethyl] -5-methoxycarbonyl-4- (naphthalen-1-yl) thiazole. {150), 2- { l- [1- (benzyloxycarbonyl) piperidin- 4-ylmethyl] -1H-imidazol-5-ylmethyl] -5- [N- (2-methoxy) ethyl-N-methylcarbamoyl] -4- (naphthalen-1-i) l) thiazole (151), 1- [1- (1-benzyloxycarbonyl-piperidin-4-ylmethyl) -1H-imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) -N-methyl] carbamoyl- 3- (naphthalen-1-yl) -lH-pyrazole (152), 1- [1- (1-methoxycarboniIpiperidin-4-ylmethyl) -lH-imidazol-5-ylmethyl] -4- [N- (2-methoxyethyl) ) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (153), 1- [1- (4-bromobenzyl-1H-imidazol-5-ylmethyl] -4- [N- ( 2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (154), 1- [1- (4-chlorobenzyl-1H-imidazol-5-ylmethyl] -4- [ N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (155), 1- [l- (4-cyanobenzyl-lH-imidazol-5-ylmethyl] - 4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (156), 1- [l-methyl-lH-imidazol-5-ylmethyl] - 4- [N- (2-methoxyethyl) -N-methyl] carbamoyl-3- (naphthalen-1-yl) -lH-pyrazole (157), 1- [1- (1-benzyloxycarbonyl-piperidin-4-ylmethyl) -1H-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole (158), 1- [1- (l-methoxycarbonylpiperi din-4-ylmethyl) -lH-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -1H-pyrazole (159), 1- [1- ( 4-bromobenzyl-lH-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole (160), 1- [1- (4-chlorobenzyl -lH-imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole (161), 1- [1- (4-cyanobenzyl-1H- imidazol-5-ylmethyl] -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole (162), and 1- (1-methyl-1H-imidazol-5-ylmethyl) ) -4- (morpholin-4-yl) carbonyl-3- (naphthalen-1-yl) -lH-pyrazole (163).
5. 5. A process for preparing an imidazole derivative compound of formula (1), according to what is defined in claim 1, characterized in that: (a) a compound represented by the formula (2) that is detailed is reacted then: where neither is defined according to claim 1 and Tr represents trityl, in a solvent in the presence of a base with a compound represented by the formula (3) which is included below: where B, C, D and X are defined according to claim 1, then the trityl group in the product obtained in this manner is removed in the presence of trifluoroacetic acid to produce a compound represented by the formula (la) which is continuation; where ni, B, C, D and X are defined according to claim 1; or (b) a compound represented by the formula (4) which is detailed below is reacted: where ni and A are defined according to claim 1, in a solvent in the presence of a base with the compound of the formula (3) to produce a compound represented by the formula (lb) detailed below: where nx, A, B, C, D and X are defined according to claim 1; or (c) a compound represented by the formula (5) which is detailed below is reacted: in a solvent in the presence of a base with the compound of the formula (3), the trityl group in the product obtained in this manner is removed in the presence of trifluoroacetic acid to produce a compound represented by the formula (6) which is detailed continuation: where B, C, D and X are defined according to claim 1, and subsequently the hydrogenation reaction is carried out to produce a compound 15 represented by the formula (le) that is included below: where B, C, D and X are defined according to claim 1; or 5 (d) a compound represented by the formula (7) is hydrolyzed as detailed below: where ni, A, B and * C are defined according to claim 1, to produce a compound represented by the formula (8) which is detailed below: where nx, A, B and C _ are defined according to claim 1, and which is subsequently reacted with a compound represented by the formula (9) detailed below: wherein R16 and R17 are defined according to claim 1, in the presence of a coupling agent to produce a compound represented by the formula (Id) that is included below: where n1, A, B, C, R6 and Ri are defined according to claim 1; or (e) the carbonyl group of a compound represented by the formula (le) which is included below is converted: where ni, A, B, C and D are defined according to claim 1, in the thiocarbonyl group in the presence of a sulfiding agent to produce a compound represented by the formula (lf) which is detailed below: Where ni, A, B, C "and D are defined according to claim 1, or (f) a compound represented by the formula (Ig) is coupled as detailed below: where B, C, D and X are defined according to claim 1, in a solvent with a compound 15 represented by the formula (10) which is detailed below: Wherein R2 is defined according to claim 1 and T represents hydroxy or a reactive leaving group, to produce a compound represented by the formula (Ih) which is included below: where R2, B, C, D and X are defined according to claim 1; or • (g) a compound represented by the formula (11) which is detailed below is cyclized: where A, G and I are defined according to claim 1, in an inert solvent to produce a compound represented by the formula (li) which is included below: where A, G and I are defined according to claim 1; or • (h) the amide group is converted to the compound of the formula (11) in the thioamide group to produce a compound represented by the formula (12) which is included below: where A, G and I are defined according to claim 1, which is subsequently cyclized in an inert solvent to produce a compound represented by 15 the formula (1)) that is included below: Wherein A, G and I are defined according to claim 1; or (i) a compound represented by the formula (13) which is detailed below is reacted: where A is defined according to claim 1, in a solvent with a compound represented by the formula (14a) which is detailed below: where G and I are defined according to claim 1, to produce the compound of the formula (Ij); or (j) the compound of the formula (13) is reacted 15 in a solvent with a compound represented by the formula (14b) which is detailed below: Wherein G and I are defined according to claim 1, to produce a compound represented by the formula (lk) which is detailed below: where A, G and I are defined according to claim 1; or (k) a compound represented by formula (11) is hydrolyzed as detailed below: where A and G are defined according to the claim le í 'represents lower alkoxy, in the presence of a base and the product thus obtained is reacted in a solvent in the presence of a coupling agent with a compound represented by the formula (15) which is detailed below: Where I "is identical to I except that lower alkoxy is not included, to produce a compound represented by the formula (lm) which is detailed below: where A and G are defined according to claim 1 and I "is defined according to the above, or (1) a compound represented by the formula (16) is reacted as detailed below: where A are defined according to claim 1, in a solvent in the presence of a base with a compound represented by the formula (17) which is detailed below: where G and L are defined - according to claim 1, to produce a compound represented by the formula where A, G and L are defined according to claim 1; or (m) a compound represented by the formula (18) which is detailed below is reacted: Where Cbz represents benzyloxycarbonyl, in a solvent in the presence of a base with the compound of the formula (17) and is deprotected to produce a compound represented by the formula (I) detailed below: where G and L are defined according to claim 1, which is subsequently coupled with a compound represented by the formula (19) which is detailed below: • T-E-F where E and F are defined according to claim 1, to produce a compound represented by the formula ip) which is detailed below: where E, F, G and L are defined according to claim 1.
6. 6. A compound represented by the formula (3) detailed below: where B, C, D and X are defined according to claim 1, with the characteristic that C is not hydrogen.
7. 7. Composite URI represented by the formula (8) detailed below: • wherein m, A, B and C are defined according to claim 1.
8. 8. A pharmaceutical composition, characterized in that it comprises as an active ingredient a therapeutically effective amount of a compound of the formula (1) according to claim 1 or a salt or a pharmaceutically acceptable isomer thereof together with a carrier 20 pharmaceutically acceptable.
9. 9. The pharmaceutical composition, according to claim 8, characterized in that it is useful in the prevention and treatment of cancer.
10. 10. The pharmaceutical composition, according to claim 8, characterized in that it is useful in the prevention and treatment of restenosis. • The pharmaceutical composition, according to claim 8, characterized in that it is useful in the prevention and treatment of atherosclerosis. 12. The pharmaceutical composition according to claim 8, characterized in that it is useful in the prevention and treatment of infections caused by hepatitis delta and related viruses. •