MXPA99001527A - Neuraminic acid compounds - Google Patents

Abstract

Constitution:Neuraminic acid compounds represented by general formula (1) or pharmacologically acceptable salts thereof, wherein R1 represents an optionally halogenated C1-C4 group;R2, R3 and R4 represent each independently hydrogen or C3-C25 aliphatic acyl;and W represents hydrogen or an ester residue, provided the case where R1 represents methyl and each of R2, R3, R4 and W represents hydrogen is excluded. Effect:These compounds are excellent in the sialidase inhibitory activity in vivo and so are useful as a remedy or preventive for influenza virus infections.

Description

COMPOSITE OF NEURAMINIC ACID TECHNICAL FIELD The present invention relates to a neuraminic acid compound or its pharmacologically acceptable salts, excellent in sialidase inhibitory activity in vivo; to compositions for the treatment or prevention or viral infections of influenza containing them as active ingredients; to its use for preparing a pharmaceutical product for treating or preventing viral infections of influenza, a method of treatment or a method of preventing viral influenza infections, by administering pharmacologically effective amounts thereof to warm-blooded animals; or to a procedure for its preparation.

THE BACKGROUND TECHNIQUE Influenza is a disease that is caused by a viral infection. As one of the methods by which this virus proliferates, subviruses have sprung up on the surface of the cells, dissociated from the cell. Said subviruses are coupled to sialic acid on the surface of the cell, by means of hemagglutinin on the surface of the subvirus. The subviruses dissociate from the cell as a result that the sialidase present on the surface of the subvirus is broken down to sialic acid, which results in secondary infection of the surrounding cells. Thus, the inhibition of sialidase would make it possible to inhibit the dissociation of the subviruses from the surface of the cells, thereby preventing secondary infection. Consequently, a substance that has the effect of inhibiting sialidase is considered to be effective in treating or preventing (but preferably treating) influenza. The known compounds having sialidase inhibitory activity and the sialic acid backbone (neuraminic acid) are described in WO 91/16320 (Japanese application of TCP (Kokai) No. Hei 5-507068). Among them, compound A (GG-167), represented by the following formula, is being developed as a drug for the treatment of influenza: Compound A (GG-167) DESCRIPTION OF THE INVENTION The inventors of the present carried out a meticulous investigation on the synthesis of a derivative having therapeutic effects on influenza infection, superior to those of compound A (GG-167), described in WO 91/16320 (Japanese patent application of TCP (Kokai) No. Hei 5-507068), and on its pharmacological activity. As a result, they found that the acyl derivatives of the hydroxyl group in positions 7 and 8 and / or position 9, and the ester derivatives of the carboxyl group in position 1, of compound A, exhibit excellent viral reproduction inhibitory activity in live and sialidase inhibitory activity similar to compound A, but also exhibit therapeutic effects for infection, superior to compound A when administered to mice infected with the influenza virus; therefore, they are useful as anti-influenza drug, and obtained the present invention. The present invention provides a neuraminic acid compound or pharmacologically acceptable salts thereof, which have excellent sialidase inhibitory activity; compositions for treating or preventing viral infections of influenza that contain them as active ingredients; its use to prepare a pharmaceutical product to treat or prevent viral infections of influenza; a method of treatment or a method of preventing viral infections of influenza; by administering pharmacologically effective amounts thereof to warm-blooded animals; or a procedure for its preparation. The neuraminic acid of the present invention has the formula: [wherein R represents an alkyl group having from 1 to 4 carbon atoms, which may be substituted with a halogen atom; R, R 3 and R A- are the same or different and each represents a hydrogen atom or an aliphatic acyl group having from 3 to 25 carbon atoms; and W represents a hydrogen atom or an ester residue; provided that the case in which R 1 is a methyl group and each of R is excluded? , R 3, R 4 - and W is a hydrogen atom]. In general formula (1) above: "The alkyl group having 1 to 4 carbon atoms" of "the alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom" of R includes , for example: the methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl and tert-butyl group, preferably a methyl group. "The halogen atom" of "the alkyl group having from 1 to 4 carbon atoms, which may be substituted with a halogen atom" of R includes, for example, the fluorine, chlorine and bromine atom, preferably a fluorine atom. "The alkyl group having 1 to 4 carbon atoms, substituted with a halogen atom" of "the alkyl group having 1 to 4 carbon atoms which may be substituted with a halogen atom "of R1 includes, for example, the monofluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 4-fluorobutyl, monochloromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl, 2-chloroethyl, 1-chloropropyl, 2-chloropropyl, 3-chloropropyl, 4-chlorobutyl, monobromomethyl, 1-bromoethyl, 2-bromoethyl, 1-bromopropyl, 2-bromopropyl, 3-bromopropyl, 4 - bromobutyl and fluorochloromethyl, preferably a methyl group substituted with a fluorine atom, the monofluoromethyl and difluoromethyl groups being more preferred, hence the "alkyl group having from 1 to 4 carbon atoms which may be substituted with a halogen atom" of R, as a whole, preferably includes a methyl group which may be substituted with a fluorine atom, more preferably, the methyl, monofluoromethyl and difluoromethyl group, most preferably, the methyl group. "The aliphatic acyl group e has from 3 to 25 carbon atoms "of R, R and R includes, for example, an alkylcarbonyl group, such as the propionyl, butyryl, isobutyryl, pentanoyl, pivaloyl, valeryl, isovaleryl, octanoyl, nonylcarbonyl, decylcarbonyl groups; -methylnonylcarbonyl, 8-methylnonylcarbonyl, 3-ethylctylcarbonyl, 3,7-dimethyloctylcarbonyl, undecylcarbonyl, dodecylcarbonyl, tridecylcarbonyl, tetradecylcarbonyl, pentadecylcarbonyl, hexadecylcarbonyl, 1-methylpentadecylcarbonyl, 14-methylpentadecylcarbonyl, 13,13-dimetiltetradecilcarbonilo, heptadecylcarbonyl, 15-metilhexadecilcarbonilo, octadecilcarbonilo, 1-metilheptadecilcarbonilo, nonadecylcarbonyl, eicosilcarbonilo, tricosilcarbonilo and tetracosilcarbonilo, preferably an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably an aliphatic acyl group having from 6 to 20 carbon atoms, with a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group being particularly preferred. R, R 3 and R 4 - as a whole, preferably are each a hydrogen atom or an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably a hydrogen atom or an aliphatic acyl group having 6 to 20 carbon atoms, in particular, preferably a hydrogen atom or a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group. As the combination of R9, R3 and R4. (a) the combination wherein R is an aliphatic acyl group having from 3 to 25 carbon atoms (preferably an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably an aliphatic acyl group having 6 to 20 carbon atoms, particularly preferably a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group), and each of R and R is a hydrogen atom; (b) the combination wherein R is an aliphatic acyl group having from 3 to 25 carbon atoms (preferably an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably, an aliphatic acyl group having 6 to 20 carbon atoms, in particular a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl,? Palmitoyl or stearoyl group is preferred and each of R and R is a hydrogen atom; (c) the combination wherein R is an aliphatic acyl group having from 3 to 25 carbon atoms (preferably an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably, an aliphatic acyl group having 6 to 20 carbon atoms, in particular a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, p palmito or stearoyl group) and each of R and R is a hydrogen atom; p (d) the combination in which each of R and R is an aliphatic acyl group having from 3 to 25 carbon atoms (preferably an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably an aliphatic acyl group having from 6 to 20 carbon atoms, with a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl), and R is a hydrogen atom; p A (e) the combination in which each of R and R is an aliphatic acyl group having from 3 to 25 carbon atoms (preferably an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably an aliphatic acyl group having from 6 to 20 carbon atoms, with particular preference being given to a hexanoyl, octanoyl, decanoyl, dodecanoyl, mipsto lo, palmitoyl group or stearoyl), and R is a hydrogen atom; (f) the combination in which each of R and R is an aliphatic acyl group having from 3 to 25 carbon atoms (preferably an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably an aliphatic acyl group having from 6 to 20 carbon atoms, with particular preference being given to a hexanoyl, octanoyl, decanoyl, dodecanoyl, p-mipstoyl, palmitoyl group or stearoyl), and R is a hydrogen atom; (g) the combination in which each of R -? , R 3 and R4 is an aliphatic acyl group having from 3 to 25 carbon atoms (preferably an aliphatic acyl group having from 6 to 25 carbon atoms, more preferably an aliphatic acyl group having from 6 to 20 carbon atoms, with particular preference being given to a hexanoyl, octanoyl, decanoyl, dodecanoyl, miristoyl, palmitoyl, or stearoyl group); and 4 (h) the combination in which each of R, R and R is a hydrogen atom. Of these combinations, the combination of (a) or (h) is preferred. "The ester residue" of W includes, for example, "a alkyl group ", such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, n- groups hexyl, isohexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3, 3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 2-ethylbutyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-propyl-butyl, 4,4-dimethylpentyl, octyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-propylpentyl, 2-ethylhexyl, 5,5-dimethylhexyl, nonyl, 3-methyl-octyl, 4-methyl-octyl, 5-methyl-octyl, 6-methyl-octyl, 1- propylhexyl, 2-ethylheptyl, 6,6-dimethylheptyl, decyl, 1-methylnonyl, 3-methylnonyl, 8-methylnonyl, 3-ethylctyl, 3,7-dimethyloxyethyl, 7,7-dimethyloctyl, undecyl, 4,8-dimethylnonyl, dodecyl, tridecyl, tetradecyl, pentadecyl, 3, 7, 11-trimethyldodecyl, h exadecyl, 4, 8, 12-trimethyltridecyl, 1-methylpentadecyl, 14-methylpentadecyl, 13, 13-dimethyltetradecyl, heptadecyl, 15-methylhexadecyl, octadecyl, 1-methylheptadecyl, nonadecyl, Icosyl, 3,7,11,15-tetramethylhexadecyl, heneicosyl, docosyl, trichosyl and tetracosyl; "an alkenyl group" such as ethenyl, 1-propenyl, 2-propynyl, 1-methyl-2-propenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, -ethyl-2-propenyl, 1-butenyl, 2-butenyl, l-methyl-2-butenyl, 1-methyl-l-butenyl, 3-methyl-2-butenyl, l-ethyl-2-butenyl, 3- butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, l-ethyl-3-butenyl, 1-pentenyl, 2-pentenyl, l-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 4-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 1-hexenyl, 2-hexenyl, 3 - hexenyl, 4-hexenyl and 5-hexenyl; "an alkynyl group" such as ethynyl, 2-propynyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-ethyl-2-propynyl, 2-butynyl, 1-methyl-2-butynyl, -methyl-2-butynyl, l-ethyl-2-butynyl, 3-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, l-ethyl-3-butynyl, 2-pentynyl, l-methyl -2-pentinyl, 2-methyl-2-pentynyl, 3-pentynyl, l-methyl-3-pentynyl, 2-methyl-3-pentynyl, 4-pentynyl, l-methyl-4-pentynyl, 2-methyl-4 -pentinyl, 2-hexynyl, 3-hexynyl, 4-hexynyl and 5-hexynyl; "a lower halogenoalkyl group", such as trifluoromethyl, trichloromethyl, difluoromethyl, dichloromethyl, dibromomethyl, fluoromethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2-bromoethyl, 2-chloroethyl, 2-fluoroethyl, -iodoethyl, 3-chloropropyl, 4-fluorobutyl, 6-iodohexyl and 2,2-dibromoethyl; "a lower hydroxyalkyl group", such as 2-hydroxyethyl, 2, m3-dihydroxypropyl, 3-hydroxypropyl, 3,4-dihydroxybutyl and 4-hydroxybutyl; "an aliphatic acyl-lower alkyl group", such as acetylmethyl; "a lower alkyl group substituted with from 1 to 3 atyls", such as benzyl, phenethyl, 3-phenylpropyl, a-naphthyldiphenylmethyl and 9-anthrylmethyl; "an aralkyl group whose aryl ring is substituted with lower alkyl, lower alkoxy, nitro, halogen, cyano or alkoxycarbonyl ", such as 4-methylbenzyl, 2,4,6-trimethylbenzyl, 3,4,5-trimethylbenzyl, 4-methoxybenzyl, 4-methoxyphenyldiphenylmethyl, 2-nitrobenzyl, 4-nitrobenzyl, 4-chlorobenzyl, 4-bromobenzyl, -cyanobenzyl, 4-cyanobenzyldiphenylmethyl, bis (2-nitrophenyl) methyl, piperonyl and 4-methoxycarbonylbenzyl; "a tri (alkyl and / or phenyl) silyl group", such as trimethylsilyl, triethylsilyl, isopropyldimethylsilyl, tert-butyldimethylsilyl, methyldiiso-propylsilyl , methyldi-tert-butylsilyl, triisopropylsilyl, methyldiphenylsilyl, isopropyldiphenylsilyl, butyldiphenylsilyl and phenyldiisopropylsilyl; "a protecting group which is capable of being decomposed, according to a biological method such as hydrolysis in a living body", ie, an ester that produces a free acid or a salt thereof when hydrolyzed in the human body, for example, "a lower alkoxy-lower alkyl group", such as methoxymethyl, 1-ethoxyethyl, 1-methyl-l-methoxyethyl, 1- (isopropoxy) ethyl, 2-methoxyethyl, 2-e Toxiethyl, 1,1-dimethyl-l-methoxymethyl, ethoxymethyl, n-propoxymethyl, Oisopropoxymethyl, n-butoxymethyl and tert-butoxymethyl; "a lower alkoxylated lower alkoxy-lower alkyl group", such as 2-methoxyethoxymethyl; "an aryloxy-lower alkyl group", such as phenoxymethyl; "a halogenated lower alkoxy-lower alkyl group", such as 2,2,2-trichloroethoxymethyl and bis (2-chloroethoxy) methyl; "a lower alkoxycarbonyl-lower alkyl group", such as methoxycarbonylmethyl; "a lower cyanoalkyl group", such as cyanomethyl and 2-cyanoethyl; "a lower alkylthiomethyl group ", such as methylthiomethyl and ethylthiomethyl;" an arylthiomethyl group ", such as phenylthiomethyl and naphththiomethyl;" a lower alkylsulfonyl-lower alkyl group which may be substituted by halogen ", such as 2-methanesulfonylethyl and 2-trifluoromethanesulfonylethyl; an arylsulfonyl-lower alkyl group, such as 2-benzenesulfonylethyl and 2-toluenesulfonylethyl; "an aliphatic acyloxy-lower alkyl group", such as formyloxymethyl, acetoxymethyl, propionyloxymethyl, butyryloxymethyl, pivaloyloxymethyl, valeryloxymethyl, isovalethyloxymethyl, hexanoyloxymethyl, 1-formyloxyethyl, 1-acetoxyethyl, 1-propionyloxyethyl, 1-butyryloxyethyl, 1-pivaloyloxyethyl, 1-valeryloxyethyl, 1-isovaleryloxyethyl, 1-hexanoyloxyethyl, 2-formyloxyethyl, 2-acetoxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-pivaloyloxyethyl, 2- valeryloxyethyl, 2-isovaleryloxyethyl, 2-hexanoyloxyethyl, 1-formyloxypropyl, 1-acetoxypropyl, 1-propionyloxypropyl, 1-butyryloxypropyl, 1- pivaloyloxypropyl, 1-valeryloxypropyl, 1-isovaleryloxypropyl, 1-hexanoyloxypropyl, 1-ethoxybutyl, 1-propionyloxybutyl, 1-butyryloxybutyl, 1-pivaloyloxybutyl, 1-acetoxypentyl, 1-propionyloxypentyl, 1-butyryloxypentyl, 1-pivaloyloxypentyl and 1-pivaloyloxyhezyl; "a cycloalkylcarbonyloxy-lower alkyl group" such as cyclopentanoyloxymethyl, cyclohexanedioxymethyl, 1-cyclopentanoyloxyethyl, 1-cyclohexanedioxyethyl, 1-cyclopentanoyloxypropyl, 1-cyclohexanedioxypropyl, 1- cyclopentanoyloxybutyl and 1-cyclohexanedioxybutyl; "an aromatic acyloxy-lower alkyl group" such as benzoyloxymethyl; "An (alkoxycarbonyloxy) alkyl" as methoxycarbonyloxymethyl, ethoxycarbonyloxymethyl, propoxycarbonyloxymethyl, isopropoxy-carbonyloxymethyl, butoxycarbonyloxymethyl, isobutoxycarbonyl-oxymethyl, pentyloxycarbonyloxymethyl, hexyloxycarbonyloxy methyl, cyclohexyloxycarbonyloxymethyl, ciciohexiloxi-carbonyloxy (cyclohexyl) methyl, 1- (methoxycarbonyloxy) ethyl, 1- (ethoxycarbonyloxy) ethyl, 1-propoxycarbonyloxyethyl, 1- (isopropoxycarbonyloxy) ethyl, 1-butoxycarbonyloxyethyl, 1-isobutoxycarbonyloxyethyl, 1- (tert-butoxycarbonyloxy) ethyl, 1-pentyloxycarbonyloxyethyl, 1-hexyloxycarbonyloxyethyl, 1-cyclopentyloxycarbonyloxyethyl, 1-cyclopentyloxycarbonyloxy-propyl , 1-cyclohexyloxycarbonyloxypropyl, 1-cyclopentyl-oxycarbonyloxybutyl, 1-cyclohexyloxycarbonyloxybutyl, 1- (cyclohexyloxycarbonyloxy) ethyl, 1- (ethoxycarbonyloxy) propyl, 2-methoxycarbonyloxyethyl, 2-ethoxycarbonyloxyethyl, 2-propoxycarbonyloxyethyl, 2-ixopropoxicarboniloxietilo, 2-butoxycarbonyloxyethyl, 2-isobutoxicarboniloxietilo, 2-pentiloxicarboniloxietilo, 2-hexiloxicarboniloxietilo, 1-metoxicarboniloxipropilo, 1-etoxicarboniloxipropilo, 1-propoxicarboniloxipropilo, 1-isopropoxicarboniloxipropilo, 1- butoxycarbonyloxypropyl, 1-oxybutoxycarbonyloxypropyl, 1-pentyloxycarbonyloxypropyl, 1-hexyloxycarbonyloxypropyl, 1-methoxycarbonyloxybutyl, 1-ethoxycarbonyloxybutyl, 1-propoxycarbonyloxybutyl, 1-hydroxycarbonyloxybutyl, 1- butoxycarbonyloxybutyl, 1-oxybutoxycarbonyloxybutyl, 1-methoxycarbonyloxypentyl, 1-ethoxycarbonyloxypentyl, 1-methoxycarbonyloxyhexyl and 1-ethoxycarbonyloxyhexyl; "an oxodioxolenylmethyl group" such as (5-phenyl-2-oxo-l, 3-dioxolen-4-ylmethyl, [5- (4-methylphenyl) -2-oxo-l, 3-dioxolen-4-yl] methyl, [5- (4-methoxyphenyl) -2-oxo-l, 3-dioxolen-4-yl] methyl, [5- (4-fluorophenyl) -2-oxo-l, 3-dioxolen-4-yl] methyl, [5- (4-methoxyphenyl) -2-oxo-l, 3-dioxolen-4-yl] methyl, [5- (4-chlorophenyl) -2-oxo-1,3-dioxolen-4-yl] methyl, [5- (4-methoxyphenyl) -2-oxo-l, 3-dioxolen-4-yl] methyl, (2-oxo-l, 3-dioxolen-4-yl) methyl, (5-methyl-2-oxo -l, 3-dioxolen-4-yl) methyl, ((5-ethyl-2-oxo-l, 3-dioxolen-4-yl) methyl, (5-propyl-2-oxo- 1, 3-dioxolen- 4-yl) methyl, (5-isopropyl-2-oxo-l, 3-dioxolen-4-yl) methyl and (5-butyl-2-oxo-1,3-dioxolen-4-yl) methyl; "a phthalidyl group", such as phthalidyl, dimethylphthalidyl and dimethoxyphthalidyl; "an aryl group" such as phenyl and indanyl; and "a carboxyalkyl group," such as carboxymethyl, preferably "an alkyl group", more preferably an alkyl group having from 1 to 18 carbon atoms. In the case where at least one of R "?, R 3 and R 4 is an aliphatic acyl group having from 3 to 25 carbon atoms," the ester residue "of W is preferably an alkyl group having 1 to 3 carbon atoms. In this case, W is, in its entirety, preferably a hydrogen atom or an alkyl group having from 1 to 18 carbon atoms, more preferably, a hydrogen atom.

In the case where each of R 0, R 3 and R 4 is a hydrogen atom, "the ester residue" of W is preferably an alkyl group having from 1 to 18 carbon atoms, more preferably an alkyl group which It has 6 to 18 carbon atoms. In that case, W as a whole, preferably is an ester residue, more preferably an alkyl group having from 6 to 18 carbon atoms. "Its pharmacologically acceptable salt" includes the alkali metal salts, such as the sodium, potassium and lithium salts; alkaline earth metal salts, such as calcium and magnesium salts; metal salts, such as the salts of aluminum, iron, zinc, copper, nickel and cobalt; the inorganic amine salts, such as the ammonium salts; organic amine salts, such as the salts of tert-octylamine, dibenzylamine, morpholine, glucosamine, phenyl glycolyl ester, ethylenediamine, N-methylglucamine, guanidine, diethylamine, triethylamine, dicyclohexylamine, N, N'-dibenzylethylenediamine, chloroprocaine, procaine, diethanolamine ,? -benzylphenethylamine, piperazine, tetramethylamminium and tris (hydroxymethyl) aminomethane; halogenated hydroacid salts, such as hydrofluoride, hydrochloride, hydrobromide and iodide; salts of inorganic acid, such as nitrate, perchlorate, sulfate and phosphate; the salts of organic acid, including the lower alkanesulfonates, such as methanesulfonate, trifluoromethanesulfonate and ethanesulfonate; arylsulfonates such as benzenesulfonate and p-toluenesulfonate; acetate, trifluoroacetate, malate, fumarate, succinate, citrate, tartrate, oxalate and maleate; and the amino acid salts such as glycine salt, lysine salt, arginine salt, ornithine salt, glutamate and aspartate, preferably the alkali metal salts, such as the sodium, potassium and lithium salts; and organic acid salts, such as acetate and trifluoroacetate; and salts of inorganic acid, such as hydrochloride and sulfate. Of the compounds of the present invention, preferred ones include the following: (1) compounds wherein R is a methyl group which may be substituted with a fluorine atom; (2) the compounds wherein R is a methyl, monofluoromethyl or difluoromethyl group; (3) the compounds wherein R is a methyl group; (4) compounds wherein R is a hydrogen atom or an aliphatic acyl group having from 6 to 25 carbon atoms; (5) compounds wherein R is a hydrogen atom or an aliphatic acyl group having from 6 to 20 carbon atoms; (6) compounds in which R is a hydrogen atom or a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group; (7) the compounds wherein R3 is a hydrogen atom or an aliphatic acyl group having from 6 to 25 atoms of carbon; (8) the compounds wherein R is a hydrogen atom or an aliphatic acyl group having from 6 to 20 carbon atoms; (9) compounds in which R is a hydrogen atom or a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group; (10) the compounds wherein R is a hydrogen atom or an aliphatic acyl group having from 6 to 25 carbon atoms; (11) compounds in which R is a hydrogen atom or an aliphatic acyl group having from 6 to 20 carbon atoms; (12) the compounds in which R 4 is a hydrogen atom or a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group; p (13) compounds wherein R is an aliphatic acyl group having from 3 to 25 carbon atoms and each of R and R is a hydrogen atom; p (14) compounds wherein R is an aliphatic acyl group having from 6 to 25 carbon atoms and each of R and R is a hydrogen atom; p (15) compounds wherein R is an aliphatic acyl group having from 6 to 20 carbon atoms and each of R and R is a hydrogen atom; p (16) the compounds in which R is a group hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl and each of R and R is a hydrogen atom; (17) compounds wherein W is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms; (18) compounds in which W is a hydrogen atom; (19) the compounds in which W is an ester residue; (20) the compounds in which it is an alkyl group having from 6 to 18 carbon atoms. Additionally, the compounds obtained by combining the substituents R, R, R, R4 and W selected in the compounds of (1) to (20) above, are more preferable and include, for example, the following compounds: (21) the compounds in each of R, R3 and R is a hydrogen atom and W is an ester residue; p -} (22) the compounds in which each of R, R and R is a hydrogen atom and W is an alkyl group having from 6 to 18 carbon atoms; (23) the compounds wherein R is a methyl group p which may be substituted with a fluorine atom; R is an aliphatic acyl group having from 3 to 25 carbon atoms; each of R and R is a hydrogen atom; and W is a hydrogen atom or an ester residue; (24) the compounds wherein R is a methyl group; R is an aliphatic acyl group having from 6 to 25 carbon atoms; each of R and R is a hydrogen atom; and W is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms; (25) the compounds wherein R is a methyl group; R is an aliphatic acyl group having from 6 to 20 carbon atoms; each of R, R and W is a hydrogen atom; (26) the compounds wherein R is a methyl group which may be substituted with a fluorine atom, each of R 0, R 3 and R 4 is a hydrogen atom, and W is an ester residue; And (27) the compounds in which R is a methyl group, each of R 0, R 3 and R 4. is a hydrogen atom and W is an alkyl group having from 6 to 18 carbon atoms. In the following, the compounds of the present invention are exemplified but the present invention is not limited thereto.

TABLE 1 1 R2 R3 R4 W CHs H H CH3CO H CH3 H H CH3 (CH2) 5CO H CH3 H H CH3 (CH2) I3CO H CH3 H CH3CO H H CH3 H CH3 (CH2) 3CO H H TABLE 1 (CONTINUED) CH3 H CH3 (CH2) 4CO H H CH3 H CH3 (CH2) gCO H H CHs H CH3 (CH2) l0CO H H CH3 H CH3 (CH2)? 6CO H H CH3 H CH3 (CH2)? 8CO H H CH3 H CH3 (CH2 2oCO H H CH3 H CH3 (CH2) 4CO CH3CO H CH3 H CH3 (CH2) 4CO CH3 (CH2) 5CO H CH3 H CH3 (CH2) «CO CH3 (CH2)? OCO H CH3 H CH3 (CH2) 4CO CH3 (CH2)? 3CO H CH3 H CH3 (CHa)? 2CO CH3CO H CH3 H CH3 (CH2) 12CO CHsCCH sCO H CH3 H CH3 (CH2 i2CO CH3 (CH2)? 0CO H CH3 H CH3 (CH2)? 2CO CH- (CH2)? 3CO H CH3 CH3CH2CO H H H CH3 CH3 (CH2) 2CO H H H CH3 CH- (CH2) 4CO H H H CH3 CH3 (CH2) 8CO H H H to CH3 H H H TABLE 1 1 [CONTINUED] 1 CHa CH3 (CH2)? 0CO H H H CHa CH3 (CH2) 12CO H H H a CHa CH3 (CH2)? 3CO H H H CHs CH3 (CH2) I4CO H H H CHa CH3 (CH2)? 6CO H H H a CHs CHa (CH2)? 7CO H H H to CH3 CH3 (CH2) 19CO H H H CH3 CHaíC? zoCO H H H a CHa CH3 (CH2) 2? CO H H H CHa CH3 (CH2) * CO H CH3CO H CH3 CH3 (CH2) 4CO H CH3 (CH2) 5CO H CH3 CH3 (CH2) CO H CH3 (CH2)? OCO H CH3 CHa (CH2) 4CO H CH3 (CH2) i3CO H CH3 CH3 (CH2)? 2CO H CH3CO H CH3 CH3 (CH2) i2CO H CH3 (CH2) 3CO H CHa CH3 (CH2) 12CO H CH3 (CH2), oCO H CHa CH3 (CH2) i2CO H CHa (CH2)? ACO H CH3 CH3CO CHACO H H CH3 CH3CH2CO CH3CH2CO H H CH3 CH3 (CH2) 2CO CH3 (CH2) 2CO H H CH3 CH3 (C? 2) 3CO CH3 (CH2) 3CO H H CH3 CH3 (CHj) 4CO CH3 (CH2) 4CO H H CH3 CH3 (CH2) 5CO CH3 (CH2) 3CO H H CH3 CHaCCH sCO H H TABLE 1 (CONTINUED) CHa CH (CH2) gCO CH3 (CH2) gCO HH CH3 CHa (CH2)? OCO CH3 (CH2)? OCO HH CHa CH3 (CH2) i2CO CH3 (CH2) i2CO HH CH3 CH3 (CH2) - 4CO CHa (CH2) i4CO HH CH3 CH3 (CH2) -6CO CH3 (CH2) iOCO HH CHa CH2 (CH2)? 8CO CHa (CH2)? 8CO HH CHa (CH2) 2oCO CH3 (CH2) 2? CO HH CHa CH3 (CH2) 22CO CH3 (CH2) 22CO HH CHa CH3 (CH2)? 2CO CH3 (CH2) 6CO HH CHa CH3 (CH2) 4CO CHa (CH2) i2CO HH CHa CH3 (CH2) 4CO CH3 (CH2) 4CO CH3CO H CHa CH3 (CH2) 4CO CHa (CH2) 4CO CH3 (CH2) 5COH CHa CH3 (CH2) »CO CH3 (CH2) * CO CH3 (CH2)? 0CO H CH3 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2) ? aCO H CHa CHa (CH2)? 2CO CH3 (CH2) 12CO CHaCO H CH3CH3 (CH2) i2CO CH3 (CH2) i2CO CH3 (CH2) 5COH CH3C? 3 (CH2) i2CO CH3 (CH2) i2CO CH3 (CH2 )? oCO H CH a CH 3 (CH 2) 12 CO CH 3 (CH 2) CO CH 3 (CH 2)? 3 CO H CH a CH 3 (CH 2) 4 CO CH 3 (CH 2), 2 CO CH 3 COO H CH a CH 3 (CH 2) 4 CO CH 3 (CH 2)? 2 CO CHa ( CH 5CO H CH 3 CH a (CH 2) 4 CO CHa (CH 2) i CO CH 3 (CH 2)? O CO H CH a CH a (CH 2 4 CO CH 3 (CH 2) i 2 CO CH 3 (CH 2)? A CO H CH a CH 3 (CH 2) i 2 CO CH 3 (CH 2) 4 CO CH3CO H CHa CHa (CH2) I2CO CH3 (CH2) 4CO CH3 (CH2) sCO H CH3 CH3 (CH2) i2CO CH3 (CH2) 4CO CH3 (CH2)? OCO H CH3 CH3 (CH2) i2CO CH3 (CH2) 4CO CH3 (CH2) i3CO H CH3 H H H (CH2) 3CH3 to CH3 H H H TABLE 1 (CONTINUED) 87f CH3 H H H (CH2) "CH3 87g CHs H H H (CH2) 12CH3 88 CH3 H H H (CH2)? 3CH3 88a CH3 H H H (CH wCHa 89 CH3 H H H (CH2)? SCHa 94 CH3 H H H (CH2) 2? CH3 94a CH3 H H H (CH2) 22CH3 95 CH3 H H CH3 (CH2) 3CO (CH2) 3CH3 96 CHaH H CH3 (CH2)? OCO (CH2)? 3CH3 97 CH3 H H CH3 (CH2) i3CO (CH2) sCHa 98 CHs H H CH3 (CH2)? SCO (CH2) i3CH3 99 CH3 H H CH3 (CH2) 17CO (C? 2) 5CH3 100 CHa H H CH 3 (CH 2) 2? CO (CH 2)? A CH 3 101 CHa H CH3CO H (CH2) 3CH3 102 CH3 H CHaCHzCO H (CH2)? 3CH3 103 CH3 H CH3 (CH2) 2CO H (CH2) 3CH3 104 CH3 H CH3 (CH2) 3CO H (CH2) 13CH3 105 CH3 H CH3 (CH-2) 4CO H (CH2) 5CH3 106 CH- H CH3 (CH) 5CO H (CH2)? 3CH3 107 CH- H CH3 (CH2) 6CO H (CH2) 3CH3 TABLE 1 (CONTINUED) 108 CH3 H CH3 (CH2) sCO H (CH2) i3CH3 109 CH3 H CH3 (CH2) 10CO H (CH2) 3CH3 110 CH3 H CH3 (CH2) i2CO H (CH2) i3CH3 111 CH3 H CH3 (CH2)? 4CO H (CH2) 5CH3 112 CHa H CHaCCH isCO H (CH2)? 3CH3 113 CHa H CH3 (CH2)? 8CO H (CH2) 5CH3 114 CH3 H CH3 (CH2) 20CO H (CH2) 13CH3 115 CHa H CH3 (CH2) 22CO H (CH2) 5CH3 116 CH3 H CH3 (CH2) 4CO CHsCO (CH2)? 3CH3 117 CH3 H CH3 (CH2) 4CO CH3 (CH2) iCO (CH2) iCH3 118 CHa H CH3 (CH2) 4CO CHa (CH2)? OCO (CH2) i3CHa 119 CHa H CH3 (CH2) 4CO CH3 (CH2)? 3CO (CH2) 5CH3 120 CH3 H CH3 (CH2) i2CO CH3CO (CH2)? 3CH3 121 CH3 H CH3 (CH2)? 2CO CH3 (CH2 3CO (CH2) 3CH3 122 CHa H CH3 (CH2) i2CO CH3 (CH2) 10CO (CH2)? 3CH3 123 CH3 H CH3 (CH2) i2CO C? 3 (CH2)? 3CO (CH2) 5CH3 124 CH3 CHACO H H (CH2)? 3CHa 125 CH3 CH3CH2CO H H (CH) 5CH3 126 CH3 CHa (CH2) 2CO H H (CH2)? 3CH3 127 CH3 CH3 (CH2) 3CO H H (CH2) 3CH3 128 CHa CHa (CH2) 4CO H H (CH2) i3CH3 129 CH3 CH3 (CH2) 5C0 H H (CH2) 5CH3 130 CH3 CH3 (CH2) 6CO H H (CH2) jaCHa 131 CH3 CH3 (CH2) 8CO H H (CH2) iCH3 132 CH3 CH3 (CH2) 10CO H H (CH2)? 3CH3 133 CHa CH3 (CH2) i2CO H H (CH2) 5CH3 134 CH3 CH3 (CH2) i4C? H H (C? 2)? 3CH3 135 CH3 CH3 (CH2)? 6CO H H (CH2) 5CHa 136 CHa CH3 (CH2) i8CO H H (CH2)? 3CH3 TABLE 1 (CONTINUED) 137 CHs CHJÍCH OCO H H (CH2) 3CH3 138 CHa CH3 (CH2) 4CO H CH3CO (CH2), 3CH3 139 CHa CH3 (CH2) CO H CH3 (CH2) 5CO (CH2) 5CH3 140 CHa CHa (CH2) 4CO H CH3 (CH2)? OCO (CH2) i3CH3 141 CHa CH3 (CH2) 4COH CH3 (CH2)? ACO (CH2) 5CH3 142 CH3 CH3 (CH2) i2CO H CH3CO (CH2)? 3CH3 143 CHa CH3 (CH2) i2CO H CH3 (CH2) 5CO (CH2) 3CHa 144 CH3 CHa (CH2) 12COH CH3 (CH2)? OCO (CH2)? 3CHa 145 CH3 CHa (CH2) i2CO H CH3 (CH2)? ACO (CH2) 5CH3 146 CH3 CHACO CH3CO H (CH2)? 3CHa 147 CH3 CH3CH2CO CH3CH-CO H CHa 148 CH3 CH3 (CH2) 2CO CHa (CH2) 2CO H (CH2) 3CH3 149 CHa CHaíCH ^ CO CHa (CH2) 3CO H (CH2)? OCH3 150 CH3 CH3 (CH2) 4CO CH3 (CH2) 4CO H (CH2) 13CH3 151 CH3 CH3 (CH2) 5CO CH3 (CH2) 3COH (CH2)? 3CH3 152 CHa CH3 (CH2) 6CO CH3 (CH2) 6CO H (CH2) i7CH3 153 CH3 CH3 (CH2) gCO CHa (CH2) 8C? H (CH 21CH3 154 CH3 CHa (CH2)? OCO CHa (CH2) j0CO H CH3 155 CHa CHa (C? A) -2CO CH3 (CH2)? 2CO H (CH2) 5CH3 156 CH3 CHa (CH2), 4CO CH3 (CH2) i4CO H (CH2)? OCH3 157 CH3 CH3 (CH2)? 6CO CH3 (CH2) i6CO H (CH2) 13CH3 158 CH3 CH3 (CH2)? 8CO CH3 (CH2) CO H (CH2) iCH3 159 CH3 CH3 (CH2) 20CO CH3 (CH2) 20CO H (CH2) 17CH3 160 CH3 CH3 (CH2) 22CO CH3 (CH2) 22COH (CH2) 2? CH3 161 CH3 CH3 (CH2)? 2CO CH3 (CH2) 6COH CH3 162 CH3 CH3 (CH2) 4CO CH3 (C? 2) 12C0 H (CH2) 3CH3 163 CHa CH3 (CH2) 4CO CH3 (CH2) -. CO CHaCO (CH2), oCH3 164 CH3 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2) 5CO (CHz)? ACH3 165 CHa CH3 (CHz) 4CO CH3 (CH2) 4CO CHa (CH2)? OCO (CH- ^ CHa TABLE 1 (CONTINUED) 166 CH3 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2)? ACO (CHa)? TCH3 167 CH3 CHa (CH2) i2CO CHa (CH2) i2CO CH3CO (CH2) 2iCH3 168 CHa CH3 (CH2) i2CO CH3 (CH2) i2CO CH3 (CH2) sCO CH3 169 CHa CH3 (CH2)? 2CO CH3 (CH2) l2CO CH3 (CH2)? OCO (CH2) 5CH3 170 CHs CH3 (CH2)? 2CO CH3 (CH2)? 2CO CH3 (CH2)? 3CO (CH2) 10CH3 171 CH3 CH3 (CH2) 4CO CHaCCH ^ CO CH3COO (CHa)? 3CHb 172 CHa CH3 (CH2) 4CO CH3 (CH2)? 2CO CH3 (CH2) sCO (CH2)? 5CH3 173 CHa CH3 (CH2) 4CO CH3 (CH2)? 2CO CHa (CH2)? OCO (CH2)? CH3 174 CHa CH3 (CH2) 4CO CH3 (CH2)? 2CO CH3 (CH2) I3CO (CH2) 2iCHa 175 CH3 CH3 (CH2) i2CO CH3 (CH2) 4CO CH3CO CH3 176 CHa CHa (CH2)? 2CO CH3 (CH2 4CO CH3 (CH2) 5CO (CH2) 3CH3 177 CH3 CH3 (CH2) 12CO CHa (CH2) 4CO CHa (CH2) 10CO (CH2)? OCH3 178 CH3 CH3 (CH2)? 2CO CH- (CH2) 4CO CHa (CH2) i3CO (CH2)? ACH3 179 CH2F HHHH 180 CTfeF HH CHACO H 181 CH2F HH CH3 (CH2) 3CO H 182 CHzF HH CH3 (CH2)? OCO H 183 CH2F HH CH3 (CH2)? ACO H 184 CH2F HH CHa (CH2)? SCO H 185 CH2F HH CH 3 (CH 2) 17 CO H 186 CH 2 F H H CH 3 (CH 2) iCO H 187 CH 2 F H CH 3 CO H H 189 CH2F H CH3 (CH2) 2CO HH 190 CH2F H CH3 (CH2) 3CO HH 191 CH2F H CHa (CH2) 4CO HH 192 CH2F H CHa (CH2) 5CO HH 193 CH2F H CHa (CH2) fcCO HH 194 CH2F H CH3 ( CH2) gCO HH TABLE 1 (CONTINUED) 195 CH2F H CH3 (CH2) .oCO H H 196 CH2F H CH3 (CH2)? 2CO H H 197 CH2F H CHa (CH2) i4CO H H 198 CH2F H CH3 (CH2)? ECO H H 199 CH2F H CH3 (CH2)? 8CO H H 200 CH2F H CH3 (CH2) 20CO H H 201 CH2F H CH3 (CH2) 22CO H H 202 CH2F H CH3 (CH) 4CO CH3CO H 203 CH2F H CH3 (CH2) 4CO CH3 (CH2) 5CO H 204 CH2F H CH3 (CH2) 4CO CHa (CH2)? OCO H 205 CH2F H CH3 (CH2) 4CO CH3 (CH2)? ACO H 206 CH2F H CH3 (CH2) i2CO CH3CO H 207 CH2F H CH (CH2)? 2CO CH3 (CH2) 3CO H 208 CH2F H CH3 (CH2) i2CO CH3 (CH2) -. OCO H 209 CH2F H CH3 (CH2) i2CO CH3 (CH2) 13CO H 210 CH2F CH3CO H H H 211 CHzF CH3CH2CO H H H 212 CH2F CHa (CH2) 2CO H H H 213 CH2F CHa (CH2) 3CO H H H 214 CH2F CH3 (CH2) 4C? H H H 215 CH2F CHa (CHa) 5CO H H H 216 CH2F CHa (CH2) < sCO H H H 217 CH2F CH3 (CH2) sCO H H H 218 CH2F CH3 (CH2)? OCO H H H 219 CH2F CH3 (CH2) i2CO H H H 220 CH2F CHa (C? 2) i4CO H H H 221 CH2F CH3 (CH2)? 6CO H H H 222 CH2F CHa (CH2)? 8CO H H H 223 CH2F CH3 (CH2) 2? CO H H H * tf Tj I Ti "TI TI •? * j * t * tl * tj í t? t? T] Tl ti l 1 Ti Ti - 't- l í j' tí ^ t 53 ÍS -S ffi 53 ÍS! S ÍS ÍS ÍS 53 53 33 -S -S W -? tS W tS tC ffi tS ÍS -S tS 33 ÍS tS TABLE 1 (CONTINUED) 253 CH2F CH3 (CH2) i2CO CH3 (CH2)? 2CO CHaCO H 254 CH2F CHa (CH2)? 2CO CH3 (CH2)? 2CO CH3 (CH2) iCO H 255 CH2F CH3 (CH2) i2CO CHa (CH2) )? 2CO CH3 (CH2), oCO H 256 CH2F CH3 (CH2) -2CO CH3 (CH2) 12C? CH3 (CH2)? 3CO H 257 CH2F CH3 (CH2) 4CO CH3 (CH2) i2CO CH3COH 258 CH2F CHa (CH2) 4CO CH3 (CH2)? 2CO CH3 (CH2) 3COH 259 CH2F CH3 (CH2) 4CO CH3 (CH2 ) 12CO CH3 (CH2)? OCO H 260 CH2F CH3 (CH2) 4C0 CH3 (CH2)? 2CO CH3 (CH2), 3CO H 261 CH2F CH3 (CH2) i2CO CH3 (CH2) 4C? CH3CO H 262 CH2F CH3 (CH2) i2CO CH3 (CH2) 4CO CHa (CH2) 3CO H 263 CH2F CHa (CH2) i2CO CH3 (CH2) 4CO CH3 (CH2) 10CO H 264 CH2F CH3 (CH2)? 2CO CH3 (CH2) 4CO CH3 (CH2)? 3CO H 265 CH2F HHH (CH2) SCH3 266 CH2F H H H (CH2)? 3CHa 269 CH2F H H H (CH2)? TCH3 270 CHzF H H H (CH2)? 8CH3 273 CHJ H H CHsCO (CH2) i3CHa 274 CH2F H H CH3 (CH2) 3CO (CH2) 5CH3 275 CH2F H H CH3 (CH2)? OCO (CH) l3CHs 276 CH2F H H CH3 (CH2) l3CO (CH2) 5CH3 278 CHJF H H CH3 (CH2) l7CO (CH2) 3CH3 280 CH2F H CH3CO H (CH2) 5CH3 281 CH2F H CH3CH2CO H (CH2)? 3CH3 TABLE 1 (CONTINUED: ION) 282 CH2F H CH3 (CH2) 2CO H (CH2) 5CH3 283 CH2F H CH3 (CH2) 3CO H (CH2)? 3CH3 284 CH2F H CH3 (CH2) CO H (CH2) 5CH3 285 CH2F H CH3 (CH2) ICO H (CH2) 13CH3 286 CH2F H CH3 (CH2) 6CO H (CH2) 3CH3 287 CH? F H CH3 (CH2) 8CO H (CH2) nCH3 288 CH2F H CH3 (CHa)? OCO H (CH2) 5CH3 289 CH2F H CHa (CH2)? 2C? H (CH2) 13CH3 290 CH2F H CH3 (CH2) MCO H (CH2) 5CH3 291 CH2F H CH3 (CH2) I6CO H (CH2) I3CH3 292 CH2F H CH3 (CH2)? 8CO H (CH2) 3CH3 293 CH2F H CH3 (CH2) 20CO H (CH2) 13CHa 294 CH2F H CH3 (CH2) 22CO H (CH2) 3CH3 295 CH2F H CH3 (CH2) 4CO CH3CO (CH2)? 3CH3 296 CH2F H CH3 (CH2) 4CO CHa (C? 2) -5CO (CH2) 5CH3 297 CH2F H CH3 (CH2) 4CO CHa (CH2)? 0CO (CH2) 13CHa 298 CH2F H CHa (CH2) 4CO CH3 (CH2) 13CO (CH2) 5CH3 299 CH2F H CH3 (CH2) j2CO CH3CO (CH2) i3CH3 300 CH2F H CH3 (CH2) 12CO CH3 (CH2) 3CO (CH2) 3CH3 301 CH2F H CH3 (CH2)? 2CO CH3 (CH2)? OCO (CH2)? 3CHa 302 CH2F H CH3 (CH2)? 2CO CH3 (CH2) 13CO (CH2) 5CHa 303 CH2F CH3CO H H (CH2)? 3CH3 304 CH2F CH3CH2CO H H (CH2) 5CH3 305 CH? F CH3 (CH2) 2CO H H (CH2) l3CHa 306 CH2F CH3 (CH2) 3CO H H (CH2) 3CH3 307 CH2F CH3 (CH2) 4CO H H (CH isCHa 308 CH2F CH3 (CH2) 3CO H H (CH2) 5CH3 309 CH? F CHa (CH2) ßCO H H (CH2)? 3CH3 310 CH2F CHa (CH2) 8CO H H (CH2) 3CH3 TABLE 1 (CONTINUED) 311 CH2F CH3 (CH2) 10CO H H (CH iaCH-- 312 CH2F CH3 (CH2) i2C0 H H (CH2) 3CH3 313 CH2F CH3 (CH2) i4CO H H (CH2) 13CH3 314 CH2F CH3 (CH2) i6CO H H (CH2) SCH3 315 CH2F CH3 (CH2)? 8C0 H H (CH2) 13CH3 316 CH2F CH3 (CH2) 2oCO H H (CH2) 3CH3 317 CH2F CHa (CH2) -, CO H CHaCO (CH2) 13CH3 318 CH2F CH3 (CH2) 4COH CH3 (CH2) 5CO (CH2) 5CHa 319 CH2F CHa (CH2) 4COH CH3 (CH2)? OCO (CH2)? 3CH3 320 CH2F CH3 (CH2) 4COH CH3 (CH2)? 3CO (CH2) 3CH3 321 CH2F CH3 (CH2) i2CO H CH3CO (CH2)? ACH3 322 CH2F CH3 (CH2)? 2COH CH3 (CH2) 3CO (CH2) 3CH3 323 CH2F CH3 (CH2) 12COH CHa (CH2) 10CO (CH2)? ACH3 324 CH2F CH3 (CH2)? 2COH CH3 (CH2) I3CO (CH2) 5CH3 325 CH2F CH3CO CH3CO H (CH2) l3CH3 326 CH2F CH3CH2CO CH3CH2CO H CH3 327 CH-F CHa (CH2) 2CO CH3 (CH2) 2CO H (CH) 5CH3 328 CH2F CH3 (CH2) 3CO CH3 (CH2) 3CO H (CH2) 10CH3 329 CH2F CH3 (CH2) 4CO CH3 (CH2) 4COH (CH2)? 3CH3 330 CH2F CH3 (CH2) jCO CH3 (CH2) iCO H (CH2)? 3CH3 331 CH2F CH3 (CH2) ßCO CH3 (CH2) 6CO H (CH2)? 7CH3 332 CHTF CH3 (CH2) 8CO CH3 (CH2) iCO H (CH2) 2-CH3 333 C? 2F CH3 (CH2) IOCO CH3 (CH2)? OCO H CHJ 334 CH2F CH (CH2) l2CO CH3 (CH2) nCO H (CH2) 5CH3 335 CH2F CH3 (CH2)? 4CO CH3 (CH2)? 4CO H (CH2) 10CH3 336 CH2F CH3 (CH2)? ECO CH3 (CH2)? ßCO H (CH2) 13CH3 337 CH? F CHa (CH2)? ACO CH3 (CH2)? ACO H (CH2)? 3CH3 338 CH2F CH3 (CH2) 2oCO CH3 (CH2) 2? CO H (CH2) 17CH3 339 CH2F CH3 (CH2) 22CO CH3 (CH2) 22CO H (CH2) 2? CH3 TABLE 1 (CONTINUED) 340 CH2F CH3 (CH2) i2CO CH3 (CH2) 6C0 H CHa 341 CH2F CH3 (CH2) 4CO CH3 (CH2)? 2CO H (CH2) 5CH3 342 CH2F CH3 (CH2) 4CO CH3 (CH2) 4C0 CHaCO 343 CH2F CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2) 5CO (CH2) 13CH3 344 CH2F CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2)? 0CO (CH2)? 5CH3 345 CH2F CH3 (CH2) 4CO CH3 (C2) 4CO CH3 (CH2) 13CO (CH2) 17CH3 346 CH2F CH3 (CH2)? 2C? CH3 (CH2)? 2CO CH3CO 347 CH2F CH3 (CH2) 12CO CH3 (CH2)? 2CO CH3 (CH2) sCO CH3 348 CH2F CH3 (CH2), 2CO CH3 (CH2)? 2C? CH3 (CH2) 10CO (CH2) 3CH3 349 CH2F CHa (CH2) i2CO CH3 (CH2) 12CO CH3 (CH2)? 3CO (CH2)? OCH3 350 CH2F CHa (CH2) 4CO CH3 (CH2) 12CO CH3CO (CH2) 13CH3 351 CH2F CH3 (CH2) 4CO CH3 (CH2) i2CO CH3 (CH2 5CO (CH2)? 3CHa 352 CH2F CH3 (CH2) 4CO CH3 (CH2) i2CO CH3 (CH2)? OCO (CH2)? 7CH3 353 CH2F CH3 (CH2) 4CO CH3 (CH2) 12CO CH3 (CH2) 13CO (CH2) 2lCH3 354 CH2F CH3 (CH2) i2C? CH3 (CH2) 4CO CH3CO CH3 355 CH2F CH3 (CH2) 12CO CH3 (CH2) 4CO CH3 (CH2) sCO (CH2) 3CH3 356 CH2F CH3 (CH2) i2CO CH3 (CH2) 4CO CH3 (CH2)? OCO (CH? OCHa 357 CH2F CH3 (CH2)? 2CO CH3 (CH2) 4CO CH3 (CH2)? 3CO (CH2 13CH3 358 CHF2 HHHH 359 CHF2 HH CHACO H 360 CHF2 HH CH3 (CH2) 5CO H 361 CHF2 HH CH3 (CH2) l0CO H 362 CHF2 HH CH3 (CH2) 13CO H 363 CHF2 HH CH3 (CH2)? 5CO H 364 CHF2 HH CH3 ( CH2) J7CO H 365 CHF2 HH CH3 (CH2) 21CO H 368 CHF2 H CH3 (CH2) 2CO H H TABLE 1 (CONTINUED) 369 CHF2 H CH3 (CH2) 3CO H H 370 CHF2 H CH3 (CH2) 4CO H H 371 CHF2 H CH3 (CH2) 5CO H H 372 CHF2 H CH3 (CH2) 6CO H H 374 CHF2 H CH3 (CH2)? OCO H H 375 CHF2 H CH3 (CH2), 2CO H H 376 CHF2 H CH3 (CH2) j4CO H H 377 CHF2 H CH3 (CH2) l6CO H H 37 * CHF2 H CH3 (CH2)? ßCO H H 379 CHF2 H CH3 (CH2) 20CO H H 380 CHF2 H CH3 (CH2) 22CO H H 381 CHF2 H CH3 (CH2) 4CO CH3CO H 382 CHF2 H CH3 (CH2) 4CO CH3 (CH2) 3CO H 383 CHF2 H CH3 (CH2) 4CO CH3 (CH2)? OCO H 384 CHF2 H CH3 (CH2) 4CO CH3 (CH2)? ACO H 385 CHF2 H CH3 (CH2) i2CO CHsCO H 386 CHF2 H CH3 (CH2) i2CO CH3 (CH) 3CO H 387 CHF2 H CH3 (CH2) l2CO CH3 (CH2)? OCO H 388 CHF2 H CH3 (CH2)? 2CO CH- (CH2) .3CO H 389 CHF2 CH3CO H H H 391 CHF2 CH3 (CH2) 2CO H H H 392 CHF2 CH3 (CH2) 3CO H H H 393 CHF2 CH3 (CH2) 4CO H H H 394 CHF2 CH3 (CH2) 3CO H H H 395 CHF2 CH- (CH2) 6CO H H H 396 CHF2 CH3 (CH2) CO H H H 397 CHF2 CH3 (CH2)? OCO H H H TABLE 1 (CONTINUED: N) 398 CHF2 CH CH pCO H H H 399 CHF2 CH3 (CH2)? 4CO H H H 400 CHF2 CH3 (CH2)? 6CO H H H 401 CHF2 CH3 (CH2)? 8CO H H H 402 CHF2 CH3 (CH2) 2oCO H H H 403 CHF2 CH3 (CH2) 4CO H CH3CO H 404 CHF2 CH3 (CH2) 4CO H CH3 (CH2) 3CO H 405 CHFZ CH3 (CH2) 4CO H CH3 (CH2)? OCO H 406 CHF2 CH3 (CH2) 4CO H CH3 (CH2 I3CO H 407 CHF2 CH3 (CH2) 12CO H CH3CO H 408 CHF2 CH3 (CH2), 2CO H CH3 (CH2) 3CO H 409 CHF2 CHa (CH2)? 2CO H CH3 (CH2) IOCO H 410 CHF2 CH3 (CH2), 2CO H CH3 (CH2), 3CO H 411 CHF2 CH3CO CH3CO H H 412 CHF2 CH3CH2CO CHaCH2CO H H 413 CHF2 CH3 (CH2) 2CO CH3 (CH2) 2CO H H 414 CHF2 CH3 (CH2) 3CO CH3 (CH2) 3CO H H 415 CHF2 CH3 (CH2) CO CH3 (CH2) 4CO H H 416 CHF2 CH3 (CH2) 5CO CH3 (CH2) 3CO H H 417 CHF2 CH3 (CH2) aCO CH3 (CH2) 6CO H H 418 CHF2 CH3 (CH2) 8CO CH3 (CH2) ßCO H H 419 CHF2 CH- (CH2) I0CO CH3 (CH2)? OCO H H 420 CHF2 CH3 (CH2) i2CO CHa (CH2) i2CO H H 421 CHF2 CHa (CH2) i4CO CH3 (CH2) 14CO H H 422 CHF2 CH3 (CH2)? <; CO CH3 (CH2) i6CO H H 423 CHF2 CH3 (CH2), gCO CH3 (CH2) 18CO H H 424 CHF2 CH3 (CH2) 2oCO CH3 (CH2) 2QCO H H 425 CHF2 CH3 (CH2) 22CO C? 3 (CH2) 22CO H H 426 CHF2 CH3 (CH2)? 2CO CH3 (CH2) 6CO H H TABLE 1 (CONTINUED) 427 CHF2 CH3 (CH2) 4CO CH3 (CH2) 12CO HH 428 CHF2 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3CO H 429 CHF2 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2) 5CO H 430 CHF2 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2)? OCO H 431 CHF2 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2)? 3CO H 432 CHF2 CH3 (CH2) 12CO CH3 (CH2)? 2CO CH3CO H 433 CHF2 CH3 (CH2) V2CO CH3 (CH2) 12C0 CH3 (CH2) 3CO H 434 CHF2 CH3 (CH2)? 2CO CH3 (CH2)? 2CO CH3 (CH2)? OCO H 435 CHF2 CH3 (CH2)? 2CO CH3 (CH2) i2CO CH3 (CH2)? 3CO H 436 CHF2 CH3 (CH2) 4CO CH3 (CH2)? 2CO CH3CO H 437 CHF2 CH3 (CH2) 4CO CH3 (CH2) i2CO CH3 (CH2) 5CO H 438 CHF2 CH3 (CH2 ) 4CO CH3 (CH2)? 2CO CH3 (CH2), 0CO H 439 CHF2 CH3 (CH2) 4CO CH3 (CH2)? 2CO CH (CH2) i3CO H 440 CHF2 CH3 (CH2) 12CO CH3 (CH2) 4CO CH3CO H 441 CHF2 CH3 (CH2)? 2CO CH3 (CH2) 4CO CH3 (CH2) 5CO H 442 CHF2 CH3 (CHz) i2CO CH3 (CH2) 4CO CH3 (CH2)? OCO H 443 CHF2 CH3 (CH2)? 2CO CH3 (CH2) 4CO CH3 (CH2)? 3CO H 444 CHF2 HHH (CH2) 3CH3 445 CHF2 H H H (CHaJiaCHa 446 CHF2 H H H (CH2) liCH3 447 CHF2 H H H (CH2)? 6CH3 449 CHF2 H H H (CH2) l8C? 3 452 CHF2 H H CH3CO (CH2)? 3CH3 453 CHF2 H H CH3 (CH2) iCO (CH2) iCH3 454 CHF2 H H CH3 (CH2)? 0CO (CH2)? 3CH3 455 CHF2 H H CH3 (CH2)? 3CO (CH2) 5CH3 TABLE 1 (CONTINUED: ION) 456 CHF2 H H CH3 (CH2) l5CO (CH2)? 3CH3 457 CHF2 H H CH3 (CH2)? TCO (CH2) 3CH3 458 CHF2 H H CH3 (CH2) 2? CO (CH2)? 3CH3 459 CHF2 H CH3CO H (CH2) 3CH3 460 CHF2 H CH3CH2CO H (CH2) 13CH3 461 CHF2 H CHa (C? 2) 2CO H (CH2) 5CH3 462 CHF2 H CH3 (CH2) 3CO H (CH2)? 3CH-, 463 CHF2 H CH3 (CH2) 4CO H (CH2) 5CH3 464 CHF2 H CH3 (CH2) 5CO H (CH2) 13CH3 465 CHF2 H CH3 (CH2) fiCO H (CH2) 5CH3 466 CHF2 H CHa (CH2) sC? H (CH2) 13CH3 467 CHF2 H CH3 (CH2), oCO H (CH2) 5CH3 468 CHF2 H CH3 (CH2)? 2CO H (CH2) i3CH3 469 CHF2 H CH3 (CH2) 14CO H (CH2) 3CH3 470 CHF2 H CH3 (CH2)? 6CO H (CH2) i3CH3 471 CHF2 H CHa (CH2)? ACO H (CH2) 5CH3 472 CHF2 H CH3 (CH2) 20CO H (CH2) i3CH3 473 CHF2 H CH3 (CH2) 22CO H (CH2) 3CH3 474 CHF2 H CH3 (CH2) 4CO CH3CO (CH2)? 3CH3 475 CHF2 H CH3 (CH) 4CO CH3 (CH2) 5CO (CH2) 5CH3 476 CHF2H CH3 (CH2) 4CO CH3 (CH2)? OCO (CH2)? 3CH3 477 CHF2H CH3 (CH2) 4CO CH3 (CH2)? 3CO (CH2) 3CH3 478 CHF2 H CH3 (CH2)? 2CO CHaCO (CH2)? 3CH3 479 CHF2H CH3 (CH2)? 2CO CH3 (CH2) 5CO (CH2) 5CH3 480 CHF2H CH3 (CH2)? 2CO CH3 (CH2)? 0CO (CH2)? 3CH3 481 CHF2H CHJ (CH2) I2CO CH3 (CH2) 13CO (CH2) 5CH-. 482 CHF2 CHACO H H (CH2)? 3CH3 483 CHF2 CH3CH2CO H H (CHdsCH- 484 CHF2 CH3 (CH2) 2COH H (CH2)? 3CH3 TABLE 1 (CONTINUED) 485 CHF2 CH3 (CH2) 3CO H H (CH2) 3CH3 486 CHF2 CH3 (CH2) 4CO H H (CH2)? ACH3 487 CHF2 CH3 (CH2) 5CO H H (CH2) 5CH3 488 CHF2 CH3 (CH2) 6CO H H (CH2)? 3CH3 489 CHF2 CH3 (CH2) gCO H H (CH2) 3CH3 490 CHF2 CH3 (CH2)? OCO H H (CH2) 13CH3 491 CHF2 CH3 (CH2)? 2CO H H (CH2) SCH3 492 CHF2 CH3 (CH2)? 4CO H H (CH2) 13CH3 493 CHF2 CH3 (CH2) 16CO H H (CH2) 3CH3 494 CHF2 CH3 (CH2) _aCO H H (CH2) I3CHa 495 CHF2 CH3 (CH2) ZoCO H H (CH2) 3CHa 496 CHF2 CH3 (CH2) 4CO H CH3CO (CH2) 13CHa 497 CHF2 CH3 (CH2) 4COH CH3 (CH2) 3CO (CH2) 3CHa 498 CHF 2 CH 3 (CH 2) 4 CO H CH 3 (CH 2) 10 CO (CH 2) 13 CH 3 499 CHF2 CH3 (CH2) 4COH CH3 (CH2) -3CO (CH2) 3CH3 500 CHF2 CH3 (CH2) i2CO H CH3CO (CH2) l3CH3 501 CHF2 CHa (CH2) i2CO H CH3 (CH2) 3CO (CH2) 5CH3 502 CHF2 CH3 (CH2) -2COH CH3 (CH2)? OCO (CH2) 13CH3 503 CHF2 CH3 (CH2) 12COH CH3 (CH2)? 3CO (CH2) 3CHa 504 CHF2 CH3CO CH3CO H (CH2) 13CH3 505 CHF2 CHaCHjCO CH3CH2CO H CH3 506 CHF2 CH3 (CH2) 2CO CH3 (CH2) 2CO H (CH2) 5CH3 507 CHF2 CH3 (CH2) 3CO CH3 (CH2) 3CO H (CH2)? OCH3 508 CHF 2 CH 3 (CH 2) 4 CO CH 3 (CH 2) 4 CO H (CH 2) 13 CH 3 509 CHF2 CH3 (CH2) 3CO CH3 (CH2) 3CO H (CH2)? 3CH3 510 CHF2 CH3 (CH2) 6CO CH3 (CH2) 6CO H (CH2) l7CH3 511 CHF2 CH3 (CH2) 8CO CH3 (CH2) aCO H (CH2) 2lCH3 512 CHF2 CH3 (CH2)? 0CO CHa (CH2)? 0CO H CH3 513 CHF2 CH3 (CH2) 12CO CH3 (CH2) l2CO H (CH2) sCH3 TABLE 1 (CONTINUED) 514 CHF2 CH3 (CH2)? 4CO H (CH2) 10CH3 515 CHF2 CH3 (CH2) t6CO CH3 (CH2)? 6CO H (CH2)? 3CH3 516 CHF2 CH3 (CH2) 18C? CH3 (CH2) 18CO H (CH2)? 5CH3 517 CHF2 CH3 (CH2) 20CO CHsCCH ^ oCO H (CH2) pCH3 518 CHF 2 CH 3 (CH 2) 22 CO CH 3 (CH 2) 22 CO H (CH 2) 2, CH 3 519 CHF 2 CH 3 (CH 2) 12 CO CH 3 (CH 2) 6 CO H CHs 520 CHF 2 CH 3 (CH 2) 4 CO CH 3 (CH 2) 2 CO 2 (CH 2) 5 CH 3 521 CHF2 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3CO (CH2) 10CH3 522 CHF2 CH3 (CH2) 4CO CH3 (CH2) 4CO CHa (CH2) 3CO (CH2)? 3CH3 523 CHF2 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2)? OCO (CH)? - CH3 524 CHF2 CH3 (CH2) 4CO CH3 (CH2) 4CO CH3 (CH2) 13CO (CH2) 17CH3 525 CHF2 CH3 (CH2) 12CO CH3 (CH2)? 2CO CH3CO (CH2) 2? CH3 526 CHF2 CH3 (CH2)? 2CO CH3 (CH2) j2CO CH3 (CH2) 5CO CH3 527 CHF2 CH3 (CH2) i2CO CH3 (CH2)? 2CO CH3 (CH2)? OCO (CH2) 3CH3 528 CHF2 CH3 (CH2)? 2CO CHa (CH2) i2CO CH3 (CH2)? 3CO (CH2)? OCH3 529 CHF2 CH3 (CH2) 4CO CH3 (CH2) 12CO CHaCO (CH2)? 3CH3 530 CHF2 CH3 (CH2) 4CO CH3 (CH2)? 2CO CH3 (CH2) 3CO (CH2)? 5CH3 531 CHF2 CH3 (CH2) 4CO CH3 (CH2)? 2CO CH3 (CH2)? OCO (CH2)? 7CH3 532 CHF2 CH3 (CH2) 4CO CH3 (CH2) l2CO CH3 (CH2)? 3CO (CH2) 2? CH3 533 CHF2 CH3 (CH2) i2CO CHa (CH 4CO CH3CO CH3 534 CHF2 CH3 (CH2) i2CO CH3 (CH2) 4CO CHa (CH2) 5CO (CH2) 3CH3 535 CHF2 CH3 (CH2) i2CO CH3 (CH2) 4CO CH3 (CH2)? OCO (CH ^ .oCHa 536 CHF2 CH3 (CH2) i2CO CH3 (CH2) 4CO CH3 (CH2)? 3CO (CH2) l3CH3 Of the above exemplary compounds, compounds 36, 37, 38, 38a, 39, 39a, 40, 40a, 41, 41a, 42, 42a, 43, 43a, 44, 44a, 45, 45a, 45b, 45c are preferred, 87, 87a, 87b, 87c, 87d, 87e, 87f, 87g, 88, 88a, 89, 90, 91, 92, 92a, 93, 94, 94a, 94b, 214, 215, 216, 217, 218, 219, 220, 221, 222, 223, 265, 266, 267, 268, 269, 270, 271, 272, 393, 394, 395, 396, 397, 398, 399, 400, 401, 402, 444, 445, 446, 447, 448, 449, 450 and 451. Compounds 36, 37, 38, 38a, 39, 39a, 40, 40a, 41, 41a, 42, 42a, 43, 43a, 44, 44a, 45, 45a are more preferred. , 45b, 45c, 87, 87a, 87b, 87c, 87d, 87e, 87f, 87g, 88, 88a, 89, 90, 91, 92, 92a, 93, 94, 94a, 94b, 219, 220, 221, 222, 269, 270, 271, 272, 398, 399, 400, 401, 448, 449, 450 and 451. The most preferred are the following compounds: 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9- O acid -hexanoyl-D-glycero-D-galac or -non-2-enopyranosoic (exemplary compound No. 36), - 5-acetamido-2, 3,4,5-tetradeoxy-4-guanidino-9-O-octanoyl acid -D-glycero-D-galacto-non-2-enopyranosoic (exemplary compound No. 38); 5-acetamido-2, 3,4,5-tetradeoxy-4-guanidino-9-O-decanoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (exemplary compound No. 39); 5-acetamido-2, 3,4,5-tetradeoxy-4-guanidino-9-O-dodecanoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (exemplary compound No. 40); -Acetamido-2, 3,4,5-tetradeoxy-4-guanidino-9-O-myristoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (exemplary compound No. 41); 5-acetamido-2, 3,4,5-tetradeoxy-4-guanidino-9-O-palmitoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (exemplary compound? or 42); 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-stearoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (exemplary compound? 43); 5-acetamido-2, 3,4, 5-tetradeoxy-4-guanidino-D-glycero-D-galacto-non-2-hexyl enopyranosoate (exemplary compound? 87); 5-acetamido-2, 3,4, 5-tetradeoxy-4-guanidino-D-glycero-D-galacto-non-2-enopyranosoate myristyl (exemplary compound? 88); 5-acetamid 5-acetamido-2, 3,4,5-tetradeoxyglycer-D-galacto-non-2-enopyranosoate cetyl (exemplary compound? 89); Stearyl 5-acetamido-2, 3,4,5-tetradeoxy-4-guanidino-D-glycero-D-galacto-non-2-enopyranosoate (exemplary compound No. 91). In the following, the process for preparing the compound (1) of the present invention will be described. The compound (1) of the present invention can be prepared according to the process described in process A, B or C, which appears later.

Additionally, compound (1) can also be prepared according to procedure J described below. The compound (2), raw material used in processes A and B, can be prepared according to the procedures described in processes D, E, F or G which appear later. In addition, the compound (5), raw material used in process C, can be prepared according to the process described in process H shown below. The meanings of R1, R2, R2a, R2b, R3, R3a, R4, R4a, R6, R7, R8, W, Wa, Me, Ac and Boc, used in the steps of procedures A to J, are shown below. That is, R1, R, R3, R4 and W have the same meanings that were defined further back; R a has the same meaning as defined for p R above or represents a protecting group of the hydroxyl group (preferably a tert-butyldimethylsilyl group or an isopropylidene group, taken together with the protecting group of the hydroxyl group of R 3a); R represents a protecting group of the hydroxyl group (preferably a tert-butyldimethylsilyl group); R has the same meaning that was defined for R above or represents a protective group of the hydroxyl group (preferably a tert-butyldimethylsilyl group or an isopropylidene group taken together with the protecting group of the hydroxyl group of R2a); R has the same meaning as defined for R above or represents a protecting group of the hydroxyl group (preferably a tert-butyldimethylsilyl group); R, R7 and R8 can be the same or different and each represents an aliphatic acyl group having from 3 to 25 carbon atoms; Wa has the same meaning as defined for W above, or represents a protecting group of the carboxyl group (preferably a methyl, ethyl, benzyl, allyl, methoxymethyl, methylthiomethyl, 2- (trimethylsilyl) ethoxymethoxy or diphenylmethyl group, more preferably a methyl, benzyl or diphenylmethyl group); Ac represents an acetyl group; Boc represents a tert-butoxycarbonyl group; and Me represents a methyl group. In the following, each procedure will be described in detail.

PROCEDURE A (3) Process A is a process for preparing the compound (1) of the present invention, by removing the protecting group of the compound (3) obtained by reacting the compound (2) raw material, which can be obtained easily according to the method described below , with N, N'-di-tert-butoxycarbonylthiourea.

STEP A-l The present step is to prepare the compound (3) by reacting the compound (2) with N, N'-di-tert-butoxycarbonyl thiourea in an inert solvent in the presence of a base and mercuric chloride. The solvent that can be used is not particularly limited as long as it does not affect the reaction, and includes the aromatic hydrocarbons, such as benzene, toluene and xylene; the ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; and the amides such as N,. -dimethylacetamide and dimethylformamide, preferably the amides (in particular N, N-dimethylacetamide and dimethylformamide). The bases included herein include preferably organic bases such as triethylamine and dimethylaminopyridine. The reaction temperature is usually from -10 to 50 ° C, preferably from 10 to 30 ° C. The reaction time varies depending on the material used, the base, the reaction temperature, etc., and will usually be from 1 to 24 hours, preferably from 5 to 10 hours. After the reaction, the desired compound is obtained, for example, by filtering the reaction mixture under reduced pressure to remove the insolubles, by adding an organic solvent immiscible with water, such as ethyl acetate, washing the mixture with water, separating the layer organic material containing the desired compound, drying the layer over anhydrous magnesium sulfate and removing the solvent by distillation. If necessary, the desired compound can be purified by recrystallization or various kinds of chromatography.

STEP A-2 The present step is to prepare the compound (1) of the present invention by reacting the compound (3) with a reagent to remove the tert-butoxycarbonyl group, in an inert solvent. The solvent that can be used is not particularly limited as long as it does not affect the reaction, and preferably includes alcohols, such as methanol and ethanol, water and a mixture thereof. The reagent for the elimination of preference is an acid, and the acid is not particularly limited at all times and when used as an acid catalyst in the usual reaction and includes Bronsted acids, such as inorganic acids, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, perchloric acid and phosphoric acid; and the organic acids, for example, acetic acid, formic acid, oxalic acid, methanesulfonic acid, paratoluenesulfonic acid, trifluoroacetic acid and trifluoromethanesulfonic acid; Lewis acids such as zinc chloride, tin tetrachloride, boron trichloride, boron trifluoride and boron tribromide; acid ion exchange resins, preferably organic acids (in particular acetic acid and trifluoroacetic acid). The reaction temperature is usually from -10 to 50 ° C, preferably from 10 to 30 ° C. The reaction time varies depending on the material, the base, the reaction temperature, etc., and is usually from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by neutralizing the reaction mixture, distilling off the solvent under reduced pressure and purifying the residue by column chromatography on silica gel. Additionally, in the case where R2a, R3a and R a are a protecting group of a hydroxyl group, or a protective group of a carboxyl group, these are eliminated. additionally to obtain the compound (1) of the present invention. The method for removing the protecting group varies depending on the class of the protecting group, and can be carried out according to the methods usually employed, for example, by the methods described in Protective Groups in Organic Synthesis, Second Edition (1991, Green and co-authors). In the case where the protecting group of a hydroxyl group is a trialkylsilyl group, such as the tert-butyldimethylsilyl group, preferably acetic acid is used in a mixture of water and tetrahydrofuran or tetrabutylammonium fluoride in tetrahydrofuran is used. In the case that the protecting group of a hydroxyl group is an isopropylidene group, the method of step E-2 or E-4 described below is used. In the case where the protecting group of a carboxyl group is a diphenylmethyl group, catalytic reduction is carried out, an acid such as acetic acid or trifluoroacetic acid is used or a trifluoroborane-diethyl ether complex is used. in the case that the protecting group of a carboxyl group is a benzyl group, catalytic reduction is carried out, and in the event that the protective group is the methyl group, a hydrolysis is carried out.

PROCEDURE B Process B is a process for preparing the compound (1) of the present invention by reacting the compound (2), a raw material, which can be obtained easily according to the method described below, with a cyanating agent, by reacting the compound resulting with ammonia and, if necessary, further eliminating the protecting group.

STEP B-l The present step is to prepare a compound (4) by reacting the compound (2) with a cyanating agent in an inert solvent. The solvent that can be used is not particularly limited, as long as it does not affect the reaction, and includes alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, alcohol isoamyl, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve; the amides such as formamide, N, n-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphoric triamide; and sulfoxides, such as dimethyl sulfoxide and sulfolane, preferably alcohols (in particular methanol). The cyanating agent that can be used preferably includes cyanogen bromide and is used simultaneously as a sodium acetate base. The reaction temperature will usually be from -10 to 50 ° C, preferably from 10 to 40 ° C. The reaction time varies depending on the material used, the base, the reaction temperature, etc., and will usually be from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by distilling off the solvent and then purifying the residue by recrystallization or by silica gel column chromatography.

STEP B-2 The present step is to prepare the compound (1) of the present invention by reacting the compound (4) with ammonia in the presence of an inert solvent. The solvent that can be used is not limited in particular as long as it does not affect the reaction and preferably includes alcohols (in particular methanol). Usually, the reaction temperature will be from -10 to 50 ° C, preferably from 10 to 40 ° C. The reaction time varies depending on the material used, the base, the reaction temperature, etc., and will usually be from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by distilling off the solvent and then purifying the residue by recrystallization or by column chromatography on silica gel. Incidentally, in the case where R, R or R a is a protecting group of a hydroxyl group, or a protective group of a carboxyl group, the compound of the present invention is obtained by removing the protecting group in a manner similar to the process TO.

PROCEDURE C Process C is a process for preparing the compound (1) of the present invention by partially or wholly acylating the hydroxyl groups of the compound (5) raw material which can be obtained easily according to the method described below, and then removing the protecting group of the resulting compound.

STEP C-1 The present step is to prepare the compound (6) by introducing a desired acyl group into the compound (5), in an inert solvent. The acylation method comprises the following acylation methods and a 3.

METHOD 1 Method 1 serves to react a compound of the general formula: RCO-Hal or a compound of the general formula: RCO-O-COR wherein: R represents an alkyl group, Hal represents a group to be eliminated, and the group to be removed is not particularly limited as long as it is a group that is eliminated as a nucleophilic residue, and preferably includes a halogen atom, such as chlorine, bromine and iodine; a lower alkoxycarbonyloxy group, such as methoxycarbonyloxy and ethoxycarbonyloxy; a halogenated alkylcarbonyloxy group, such as chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy and trifluoroacetyloxy; a lower alkanesulfonyloxy group such as methanesulfonyloxy and ethanesulfonyloxy; a lower halogeno-alkanesulfonyloxy group, such as trifluoromethanesulfonyloxy and pentafluoroethanesulfonyloxy; and an arylsulfonyloxy group such as benzenesulfonyloxy, p-toluenesulfonyloxy and p-nitrobenzenesulfonyloxy; more preferably, a halogen atom, a halogeno-lower alkanesulfonyloxy group and an arylsulfonyloxy group] with the compound (5) in a solvent in the presence or absence of a base. The solvent that can be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to a certain degree, and preferably includes aliphatic hydrocarbons such as hexane and heptane.; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene; the esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; the ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; and the amides like formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphoric triamide. The base that can be employed is not particularly limited in particular as long as it is used as a base in a usual reaction and preferably includes organic bases, such as N-methylmorpholine, triethylamine, tributylamine, diisopropylethylamine, dicyclohexylamine, N-methylpiperidine, pyridine. , 4-pyrrolidinopyridine, picoline, 4- (N, N-dimethylamino) pyridine, 2,6-di (tert-butyl) -4-methylpyridine, quinoline, N, N-dimethylaniline and N, N-diethylaniline. Incidentally, 4- (N, N-dimethylamino) pyridine and 4-pyrrolidinopyridine can be used in a catalytic amount, by combining it with other bases and additionally quaternary ammonium salts, such as benzyltriethylamminium chloride and tetrabutylamminium chloride, and ethers can also be added of corona, such as dibenzo-18-corona-6-, in order to effectively carry out the reaction. The reaction is usually carried out at temperatures from -20 ° C to the reflux temperature of the solvent used, preferably from 0 ° C to the reflux temperature of the solvent used. The reaction time varies depending mainly on the reaction temperature, the raw material, the base used and the kind of solvent used; Y usually it will be from 10 minutes to 3 days, preferably from 1 to 6 hours.

METHOD 2 Method 2 is to react a compound of the general formula: RCOOH [wherein R has the same meaning as defined above], with the compound (5) in a solvent, in the presence or absence of an "esterifying agent" , and of a catalytic amount of base. The "esterifying agent" that can be employed includes a condensing agent, halogenated formates such as methyl chloroformate and ethyl chloroformate, and diesters of cyanophosphoric acid, such as diethyl cyanophosphate. Said "condensing agents" include the N-hydroxy derivatives, such as N-hydroxysuccinimide, 1-hydroxybenzotriazole and N-hydroxy-5-norbornene-2,3-dicarboxyimide; the disulfide compounds such as 2,2 '-dipyridyl disulfide; succinic acid compounds, such as N, N '-disuccinimidyl carbonate; phosphinic chloride compounds such as N, N'-bis (2-oxo-3-oxazolidinyl) phosphinic chloride; oxalate derivatives such as N, N'-disuccinimidyl oxalate (DSO), N, N'-dipthalimide oxalate (DPO), N, N'-bis (norbornenyl-succinimidyl) oxalate (BNO), oxalate of 1, 1'-bis (benzotriazolyl) (BBTO), 1,1'-bis (6-chlorobenzotriazolyl) oxalate (BCTO) and 1,1'-bis (6-trifluoromethylbenzotriazolyl) oxalate (BTBO); triarylphosphines, such as triarylphosphines, for example, triphenylphosphine and di-lower alkyl triarylphosphines of azodicarboxylic acid, such as triphenylphosphine of diethyl azodicarboxylate; 3'-N-lower alkyl-5-arylisoxazolium sulfonates, such as 3'-N-ethyl-5-phenylisoxazolium sulfonate; carbodiimide derivatives, such as N ', N' -dicycloalkylcarbodiimides, for example, N ', N' -diiocyclohexylcarbodiimide (DCC) and l-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDAPC); diheteroaryl-diselenides such as di-2-pyridyldiselenide; arylsulfonyl triazolides such as p-nitrobenzenesulfonyltriazolide; halides of 2-hals-l-lower alkyl-pyridinium such as 2-chloro-1-methylpyridinium iodide; diarylphosphorylazides such as diphenylphosphorylazide (DPPA); and imidazole derivatives, such as 1,1 '-oxazolidilimidazole and N, N' -carbonyldiimidazole, preferably diarylphosphoryl azides. The solvent that can be used is not particularly limited, as long as it does not inhibit the reaction and dissolves the starting material to some extent; and preferably includes aliphatic hydrocarbons, such as hexane and heptane; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene; the esters, such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate and diethyl carbonate; the ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and dimethyl ether diethylene glycol; nitriles such as acetonitrile and isobutyronitrile; amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphoric triamide. As a basis to be used, bases similar to those described in "method 1" above can be used. The reaction is carried out from -20 ° C to 80 ° C, preferably from 0 ° C to room temperature. The reaction time varies depending mainly on the reaction temperature, the raw material compound, the reaction reagent and the kind of solvent used, and will usually be 10 minutes to 3 days, preferably 30 minutes to a day.

METHOD 3 Method 3 is for reacting the compound of the general formula: RCOOH [wherein R has the same meaning as defined above] with the compound (5) in a solvent, in the presence of the dialkyl ester of the halogenated phosphoric acid, as dichlorophosphate of diethyl, and of a base. The solvent that can be employed is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent and preferably includes the aliphatic hydrocarbons, such as hexane and heptane; the aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene; the esters, such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate and diethyl carbonate; the ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; nitriles such as acetonitrile and isobutyronitrile; amides such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphoric triamide. As the base used, bases similar to those described in "method 1" above can be used. The reaction is carried out at temperatures of 0 ° C to the reflux temperature of the solvent used, preferably at room temperature to 50 ° C. The reaction time varies depending mainly on the reaction temperature, the raw material, the reaction reagent and the kind of solvent used, and will usually be 10 minutes to 3 days, preferably 30 minutes to a day. In the above "method 1", "method 2" and "method 3", the compound (6) into which 1 to 3 acyl groups are introduced to the compound (5), can be obtained by appropriately controlling an equivalent amount of the agent acylating used with respect to the compound (5).

After the reaction, the desired compound (6) of the present reaction, of the reaction mixture, is collected according to the conventional method. For example, the desired compound can be obtained by properly neutralizing the reaction mixture, eliminating the insolubles by filtration, if they exist, and adding an organic solvent immiscible with water, such as ethyl acetate, washing it with water, separating the organic layer containing the desired compound, drying the layer over anhydrous magnesium sulfate and removing the solvent by distillation. The compound thus obtained can be separated and purified, if necessary, by appropriately combining conventional methods, for example, recrystallization, reprecipitation or a method that can be commonly employed to separate and purify organic compounds, for example, adsorption column chromatography, using carriers such as silica gel, alumina, Florisil or magnesium-silica gel system; a method using a synthesized adsorber agent, such as partition column chromatography, using carriers such as Sphadex LH-20 (manufactured by Pharmacia Co. Ltd.), Amberlite XAD-11 (manufactured by Rohm &Haas Co., Ltd.) and Diaion HP-20 (Mitsubishi Chemical Corp.) or normal-phase column chromatography-reverse phase, using silica gel or alkylated silica gel (preferably high performance liquid chromatography) and eluting with appropriate elution solutions.

STEP C-2 The present step is to prepare the compound (1) of the present invention by removing the tert-butoxycarbonyl group in the compound (6) in an inert solvent. The present step can be carried out in a manner similar to the procedures of step A-2. Additionally, in the case that Wa is a protecting group of a carboxyl group, the compound (1) of the present invention can be obtained by further eliminating them in a manner similar to the procedures of step A-2.

PROCEDURE D D'Z "HO., .._, 0 --_ COOMe 0-3 'CNH OR N3 (9) Procedure D is to prepare the compound • (2a), which is one of the starting compounds in the Procedures A and B, using the starting compound (7), easily obtainable according to the method described below.

STEP D-1 The present step is to prepare the compound (8) by reacting the compound (7) with a base in an inert solvent. The solvent that can be used is not particularly limited as long as it does not inhibit the reaction and dissolve the starting material to some extent; and preferably includes aliphatic hydrocarbons such as hexane, heptane, logroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene; the ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; and methanol, preferably halogenated hydrocarbons and methanol. The base that can be used is not particularly limited as long as it does not affect the other functional groups (for example, methyl ester) and includes the alkali metal methoxides, preferably, such as sodium methoxide and potassium methoxide.

The reaction temperature will usually be from -10 to 50 ° C, preferably from 10 to 30 ° C. The reaction time varies depending on the material used, the base, the reaction temperature, etc., and will usually be from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by neutralizing the reaction mixture by hydrochloric acid / dioxane solution, distilling off the solvent under reduced pressure and then purifying the residue by silica gel column chromatography.

STEP D-2 The present step is to prepare the compound (9) by reacting the compound (8) with a reagent to introduce an isopropylidene group in an inert solvent. The solvent that can be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, and includes the aliphatic hydrocarbons such as hexane, heptane, attainin and petroleum ether; aromatic hydrocarbons such as benzene, toluene and xylene; the ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; and ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone and cyclohexanone, preferably ketones (in particular acetone). The reagent that can be used preferably includes 2,2-dimethoxypropane and acids such as p-toluenesulfonic acid are used as a catalyst. The reaction temperature will usually be from -10 to 50 ° C, preferably from 10 to 30 ° C. The reaction time varies depending on the material used, the base, the reaction temperature, etc., and is usually from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by adding a water-immiscible solvent, such as ethyl acetate and an aqueous solution of sodium bicarbonate to the reaction mixture, extracting the desired compound with ethyl acetate and removing by distillation the solvent. The desired compound can be further purified, if necessary, by recrystallization or various kinds of chromatographies.

STEP D-3 If necessary, the present step: (1) replaces the methyl group of the methyl carboxylate moiety with another ester residue; (2) hydrolyzes the methyl carboxylate moiety; or (3) introduces a protecting group of the carboxyl group or the ester residue, after the hydrolysis of (2).

CHANGE OF ESTER The present step is to prepare the compound (10), by reacting the compound (9) with an alcohol which can give the desired ester group in an inert solvent, in the presence of a base. The solvent that can be used is not particularly limited, as long as it does not inhibit the reaction and includes, for example, the aliphatic hydrocarbons, such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons, such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene; the ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; and alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve. Preferably, an alcohol forming the desired ester group can be used as the solvent. The base that can be used preferably includes organic bases, such as pyridine, triethylamine, diethylamine and N, N-dimethylaminopyridine. After the reaction, the compound can be obtained desired, for example, by neutralizing the reaction mixture with an acid, adding a solvent immiscible with water, such as ethyl acetate, to the mixture, extracting the desired compound with ethyl acetate, etc., washing it with water and removing by distillation the solvent. The desired compound can be further purified, if desired, by recrystallization or various kinds of chromatographies.

THE DIFENYMETILATION The present step is to prepare the compound (10) by reacting the compound (9) with diphenyldiazomethane in an inert solvent in the presence of a Lewis acid. The solvent that can be used is not particularly limited so long as it does not inhibit the reaction and dissolves the starting material to some extent, and preferably includes the aliphatic hydrocarbons, such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons, such as benzene, toluene and xylene; halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane and chlorobenzene; the ethers, such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and ethylene glycol dimethyl ether; and alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methyl cellosolve. More preferable, alcohols (particularly methanol), halogenated hydrocarbons (dichloromethane) and mixtures thereof. The Lewis acid that can be used preferably includes the boron trifluoride ether complex. Usually the reaction temperature is from 0 to 50 ° C, preferably room temperature. The reaction time varies depending on the starting material, the Lewis acid and the reaction temperature, and is usually from 10 minutes to 5 hours, preferably 1 to 3 hours. After the reaction, the solvent is distilled off and the purification is carried out by recrystallization or chromatography to obtain the desired compound.

THE HYDROLYSIS The present step is to prepare the compound (10), wherein Wa is a hydrogen atom, hydrolyzing the compound (9) in an inert solvent, in the presence of a base. The solvent that can be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, and preferably includes aromatic hydrocarbons, such as benzene and, toluene; the ethers, such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as dichloromethane and chloroform; ketones, such as acetone and methyl ethyl ketone; water and mixtures of these solvents and water. The base that can be used includes the alkali metal hydroxides, such as lithium hydroxide, sodium hydroxide and potassium hydroxide; and alkali metal bicarbonates, such as sodium bicarbonate and potassium bicarbonate. Usually the temperature of the reaction is from -10 to 50 ° C, preferably from 10 to 30 ° C. The reaction time varies depending on the raw material used, the base, the reaction temperature, etc., and is usually from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by cooling the reaction mixture, making it weakly acidic by the use of dilute hydrochloric acid, adding a solvent immiscible with water, such as ethyl acetate, to the reaction mixture, extracting the desired compound with ethyl acetate and distilling off the solvent. The desired compound can be further purified by recrystallization or various kinds of chromatography.

INTRODUCTION OF THE PROTECTIVE GROUP OF THE CARBOXILO GROUP OR THE ESTER RESIDUE The present step is to prepare the compound (10) introducing the protecting group or the ester residue to the carboxyl group in the 1-position of the compound (9) in which a is a hydrogen atom. The introduction of the protective group or the ester residue varies, depending on the class of the ester residue or the protecting group, and can be carried out according to methods generally used in the field of organic synthesis chemistry, for example, the methods described in Protective Groups in Organic Synthesis, Second Edition (1991, Green and co-authors).

STEP D-4 The present step is to prepare the compound (2a) from the compound (10), using a reducing agent in an inert solvent. The solvent that can be used is not particularly limited so long as it does not inhibit the reaction and dissolves the starting material to some extent, and preferably includes the aliphatic hydrocarbons, such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons, such as benzene, toluene and xylene; the ethers, such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, isoamyl alcohol, diethylene glycol, glycerin, octanol, cyclohexanol and methylcellosolve; ketones, such as methyl ethyl ketone, methyl xyl butyl ketone, isophorone and cyclohexanone; nitriles, such as acetonitrile and isobutyronitrile; the amides, such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphoric triamide; sulfoxides, such as dimethyl sulfoxide and sulfolane; the aliphatic carboxylic acids, such as acetic acid; and mixtures of these organic solvents and water; preferably the alcohols (in particular methanol), the ethers such as tetrahydrofuran and dioxane, the aliphatic carboxylic acids such as acetic acid, and mixtures of these organic solvents and water. As the reducing agent used, a catalyst of palladium on carbon, platinum and Raney nickel can be used in the presence of hydrogen gas, and a Lindlar catalyst (Pd-BaSO4 or dCaCO3 and quinoline is used in particular). or lead acetate in combination). Usually the temperature of the reaction is from -10 ° C to 50 ° C, preferably from 10 to 30 ° C. The reaction time varies depending on the raw material used, the base, the temperature of the reaction, etc., and will usually be from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example by filtering the reaction mixture under reduced pressure to remove the catalyst and removing the solvent by distillation under reduced pressure. The desired compound can be further purified, if necessary, by recrystallization or various kinds of chromatography.

PROCEDURE E Process E is a process for preparing compound (2b) or (2c) which is one of the starting compounds in processes A and B, using the starting compound (10), which can be obtained easily in accordance with previous method.

STEP E-l The present step is to prepare the compound (12) by introducing the desired acyl group to the compound (10) in an inert solvent. Additionally, the present step can be carried out in a manner similar to the procedures of step C-1 above.

STEP E-2 The present step is to prepare the compound (13) by treating the compound (12) with a reagent to remove the isopropylidene group in an inert solvent. The solvent that can be used is not particularly limited, as long as it does not inhibit the reaction and dissolves the starting material to some extent, and preferably includes halogenated hydrocarbons, such as methylene chloride and chloroform. As the reagent for removal, an acid is preferred, and the acid is not particularly limited as long as it is used as an acid catalyst in the usual reaction, and includes Bronsted acids, such as inorganic acids, for example, hydrochloric acid , hydrobromic acid, sulfuric acid, perchloric acid and phosphoric acid; and organic acids such as formic acid, acid oxalic, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid and trifluoromethanesulfonic acid; and Lewis acids, such as zinc chloride, tin tetrachloride, boron trichloride, boron trifluoride and boron tribromide; and the acid ion exchange resins; preferably organic acids (in particular trifluoroacetic acid). The reaction temperature is usually from -10 to 50 ° C, preferably from 10 to 30 ° C. The reaction time varies depending on the raw material used, the base, the reaction temperature, etc., and will usually be from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by neutralizing the reaction mixture, distilling off the solvent under reduced pressure and then purifying the residue by chromatography on silica gel. Additionally in the present step, the acyl group (R) in position 7 is transferred to position 9.

STEP E-3 The present step is to prepare the desired raw material or starting compound (2b) from the compound (13), using a reducing agent in an inert solvent. The present step is carried out in a similar way to the procedures of step D-4 above.

STEP E-4 The present step is to prepare the compound (14) of the present invention by treating the compound (12) with a reagent to remove the isopropylidene group in an inert solvent in the presence of an acid catalyst. The solvent that can be employed is not particularly limited, as long as it does not inhibit the reaction and dissolves the starting material to some extent, and preferably includes a mixture of acetic acid (which is used simultaneously as the acid catalyst) and water. The reaction temperature is usually 10 to 70 ° C, preferably 30 to 60 ° C. The reaction time varies depending on the raw material used, the base, the reaction temperature, etc .; and usually it is from 15 minutes to 24 hours, preferably from 10 to 20 hours. After the reaction, the desired compound can be obtained, for example, by distilling off the solvent under reduced pressure, by adding to the reaction mixture a solvent immiscible with water, such as ethyl acetate and an aqueous solution of sodium bicarbonate, extracting the desired compound with ethyl acetate and distilling off the solvent. The desired compound can be further purified, if necessary, by recrystallization or various kinds of chromatography.

STEP E-5 The present step is to prepare the desired starting material or starting material (2c) from the compound (14) using a reducing agent in an inert solvent. The present step can be carried out in a manner similar to the procedures of step D-4 above.

PROCEDURE F F-2 (17) (16) F-4 F-6 F-5 Process F is a process for preparing compound (2d) or (2c), which is one of the starting materials or starting material in processes A and B using the starting compound (14), which can be obtained easily according to the previous method.

STEP F-1 The present step is to prepare the compound (15) by reacting the compound (14) with a reagent to prepare the hydroxyl compound in an inert solvent. The protecting group is not particularly limited and preferably includes a tert-butyldimethylsilyl group and a tert-butyldiphenylsilyl group. Silylation can be carried out according to usual methods. For example, silylation can be carried out by reacting tert-butyldimethylsilyl halide (particularly the chloride) in dimethylformamide in the presence of a base such as triethylamine and 4- (N, N-dimethylamino) pyridine. The reaction temperature is usually from -10 to 50 ° C, preferably from 10 to 40 ° C. The reaction time varies depending on the raw material used, the base, the reaction temperature, etc., and is usually from 15 minutes to 24 hours, preferably from 10 to 20 hours.

After the reaction, the desired compound can be obtained, for example, by adding a solvent immiscible with water, such as ethyl acetate, and an aqueous solution of sodium bicarbonate to the reaction mixture; extracting the desired compound with ethyl acetate and distilling off the solvent. The desired compound can be further purified, if necessary, by recrystallization or various kinds of chromatography.

STEP F-2 The present step is to prepare the compound (16) by introducing the desired acyl group to the compound (15) in an inert solvent. The present step can be carried out in a manner similar to the procedures of step C-1.

STEP F-3 The present step is to prepare the compound (17) by reacting the compound (16) with a reagent to remove the protecting group (preferably a tert-butyldimethylsilyl group or a tert-butyldiphenylsilyl group) of the hydroxyl group, in an inert solvent. The solvent that can be used includes alcohols, preferably, such as methanol and ethanol, water and mixtures thereof.

The acids are preferably used as reagents for elimination, and the acid is not particularly limited as long as it is used as an acid catalyst in the usual reactions, and includes Bronsted acids, such as inorganic acids, for example, hydrochloric acid. , hydrobromic acid, sulfuric acid, perchloric acid and phosphoric acid; and the organic acids, for example, acetic acid, formic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid and trifluoromethanesulfonic acid; and Lewis acids, such as zinc chloride, tin tetrachloride, boron trichloride, boron trifluoride and boron tribromide; and acid ion exchange resins; preferably organic acids (in particular, acetic acid and trifluoroacetic acid). Reagents that produce a fluoride ion, such as tetrabutylammonium fluoride, can also be used, if desired. The reaction temperature is usually -10 to 50 ° C, preferably 10 to 30 ° C. The reaction time varies depending on the raw material used, the base, the reaction temperature, etc .; and usually it is from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by neutralizing the reaction mixture, by distilling off the solvent under reduced pressure and purifying the residue by chromatography, on silica gel. In the present step, the acyl group (R) is transferred from position 8 to position 9.

STEP F-4 The present step is to prepare the compound (18): (1) protecting the hydroxyl group from the 8-position in the compound (17); or (2) introducing the desired acyl group, when desired.

THE INTRODUCTION OF THE ACILO GROUP The present step can be carried out in a manner similar to the procedures of step C-1.

INTRODUCTION OF THE PROTECTOR GROUP The tert-butyldimethylsilyl group is preferred as protective group, and the protective group is introduced using tert-butyldimethylsilyl triflate and lutidine in methylene chloride.

STEP F-5 The present step is to prepare the desired starting compound (2b) from the compound (18), using a reducing agent in an inert solvent. The present step can be carried out in a manner similar to the procedures of step D-4.

STEP F-6 The present step is to prepare the desired starting compound (2e) from the compound (16) using a reducing agent in an inert solvent. The present step can be carried out in a manner similar to the procedures of step D-4.

PROCEDURE G Process G is a process for preparing compound (2f) or (2g) which is one of the starting compounds in processes A and B, using the above compound (13) or (14), described above.

STEP G-1 The present step is to prepare the compound (19) by introducing the desired acyl group to the compound (13), in an inert solvent. The present step can be carried out in a manner similar to the procedures of step C-1.

STEP G-2 The present step is to prepare the starting compound (2f) from the compound (19), using a reducing agent in an inert solvent. The present step can be carried out in a manner similar to the procedures of step D-4.

STEP G-3 The present step is to prepare the compound (20) by introducing the desired acyl group to the compound (14) in an inert solvent. The present step can be carried out in a manner similar to the procedures of step C-1.

STEP G-4 The present step is to prepare the desired starting compound (2g) from the compound (20), using a reducing agent in an inert solvent. The present step can be carried out in a manner similar to the procedures of step D-4.

PROCEDURE H Process H is a process for preparing compound (5), which is a starting material or raw material in process C, using the well-known compound (26) described in Carbohydrate Research, 83, 163-169 (1980) or in WO 95/32955.

STEP H-l The present step is to prepare the compound (27) by reacting the known compound (26) with an azidating agent, in an inert solvent. The solvent that can be employed is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, and preferably includes aromatic hydrocarbons, such as benzene, toluene and xylene; halogenated hydrocarbons such as methylene chloride and chloroform; the ethers such as diethyl ether, tetrahydrofuran, dioxane and dimethoxyethane; and nitriles, such as acetonitrile. The reagent that can be used is not particularly limited so long as it is usually used for azidation and preferably includes diarylphosphoric azide derivatives, such as diphenylphosphoric azide; trialkylsilylazides, such as trimethylsilylazide and triethylsilylazide; and alkali metal salts azidated, such as sodium azide and potassium azide, preferably sodium azide.

The reaction temperature is usually from -10 to 50 ° C, preferably from 10 to 30 ° C. The reaction time varies depending on the raw material used, the base, the reaction temperature, etc., and is usually from 15 minutes to 10 hours, preferably from 1 to 5 hours. After the reaction, the desired compound can be obtained, for example, by neutralizing the reaction mixture with a solution of hydrochloric acid / dioxane and purifying the residue obtained by distilling off the solvent under reduced pressure, or by chromatography on silica gel.

STEP H-2 The present step is to prepare the compound (28) by reacting the compound (27) with a tert-butoxycarbonylating agent in an inert solvent. The tert-butoxycarbonylation can be carried out by reacting di-tert-butyl dicarbonate or 2- (tert-butoxycarbonyloxyimino) -2-phenylacetonitrile in an inert solvent (for example, aromatic hydrocarbons such as benzene and toluene); halogenated hydrocarbons such as methylene chloride and chloroform; ethers such as diethyl ether, tetrahydrofuran and dioxane; and amides such as dimethylformamide) in the presence of a base (e.g., 4- (N, N-dimethylamino) pyridine). After the reaction, the compound can be obtained desired, for example, by neutralizing the reaction mixture, distilling off the solvent under reduced pressure, adding a solvent immiscible with water, such as ethyl acetate, extracting the desired compound with ethyl acetate and distilling off the solvent. The compound can be further purified, if necessary, by recrystallization or various kinds of chromatography.

STEP 3 The present step is to prepare the compound (29) by reacting the compound (28) with a base in an inert solvent. The present step can be carried out in a manner similar to the procedures of step D-1.

STEP H-4 The present step is to acetylate the compound (29) in an inert solvent. Acylation is carried out according to the usual method to protect a hydroxyl group. For example, acetylation can be carried out: (1) by reacting with acetic anhydride in pyridine; or (2) by reacting with acetyl halide (particularly chloride) in methylene chloride, in the presence of a basic catalyst (e.g., triethylamine and 4-N, N- dimethylaminopyridine). After the reaction, the desired compound can be obtained by distilling off the solvent under reduced pressure, adding a solvent immiscible with water, such as ethyl acetate, and an aqueous solution of sodium bicarbonate to the residue, extracting the desired compound with ethyl acetate. ethyl and removing the solvent by distillation. The desired compound can be further purified, if necessary, by recrystallization or various kinds of chromatography.

STEP H-5 The present step is to prepare the compound (30) by treating the compound obtained in step H-4 with a reagent that removes a tert-butoxycarbonyl group in an inert solvent. The elimination of the tert-butoxycarbonyl group is carried out according to the usual methods. The solvent that can be used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent and preferably includes the aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons, such as benzene, toluene and xylene; halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene and dichlorobenzene; the esters, like ethyl formate, ethyl acetate, propyl acetate, butyl acetate or diethyl carbonate; the ethers, such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether; the amides, such as formamide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylpyrrolidinone and hexamethylphosphoric triamide; and sulfoxides, such as dimethyl sulfoxide and sulfolane; preferably the halogenated hydrocarbons (in particular, methylene chloride). The reagent that can be used is not particularly limited as long as it is used regularly and includes hydrochloric acid, preferably. The reaction temperature is usually -10 to 50 ° C, preferably 10 to 30 ° C. The reaction time varies depending on the raw material used, the base, the reaction temperature, etc., and is usually from 15 minutes to 24 hours, preferably from 1 to 10 hours. After the reaction, the desired compound can be obtained, for example, by distilling off the solvent under reduced pressure, adding a solvent immiscible with water, such as ethyl acetate, and an aqueous solution of sodium bicarbonate, to the reaction mixture; extracting the desired compound with ethyl acetate and distilling off the solvent. The desired compound can be further purified, if necessary, by recrystallization or various kinds of chromatographies STEP H-6 The present step is to prepare the compound (7) by introducing the desired acyl group into the compound (30) in an inert solvent. The present step can be carried out in a manner similar to the procedures of step C-1.

STEP H-7 The present step is to prepare the compound (32) from the "compound (7), using a reducing agent in an inert solvent.The present step can be carried out in a manner similar to the procedures in step D-4.

STEP H-8 The present step is to prepare the compound (33) by reacting the compound (32) with N, N'-di-tert-butoxycarbonyl thiourea in an inert solvent in the presence of a base and mercuric chloride. The present step can be carried out in a manner similar to the procedures of step A-1.

STEP H-9 The present step is to prepare the compound (34) by reacting the compound (33) with a base in an inert solvent. The present step can be carried out in a manner similar to the procedures of step D-1.

STEP H-10 Ester change, hydrolysis, protection or esterification The present step is: (1) to replace the methyl group of the methyl carboxylate moiety with another ester residue; (2) to hydrolyze the methyl carboxylate moiety; or (3) to introduce a protecting group of the carboxyl group or an ester residue after the hydrolysis in (2), as desired. The present step can be carried out in a manner similar to the procedures of step D-3. The compound (1) of the present invention can also be prepared according to procedures different from those described above. In particular, it is possible to prepare the compound (1) of the present invention by changing the order of the steps of the processes A to H described above, depending on the situations. For example, the compound (1) of the present invention can be prepared according to method J shown below, using the compound (10) obtained as an intermediary in procedure D.

PROCEDURE J J-2 J-4 STEP J- 1 The present step is carried out, if necessary, and is to prepare the compound (35) by introducing the desired acyl group to the compound (10), in an inert solvent. The present step can be carried out in a similar to the procedures of step C-1 described above.

STEP J-2 The present step is to prepare the compound (36) by reacting the compound (35) with a reducing agent in an inert solvent. The present step can be carried out in a manner similar to the procedures of step D-4 described above.

STEP J-3 The present step is to prepare the compound (37) by reacting the compound (36) with N, N'-di-tert-butoxycarbonyl thiourea in an inert solvent in the presence of a base and mercuric chloride. The present step can be carried out in a manner similar to the procedures of step A-l described above.

STEP J-4 The present step is carried out, if necessary, and is to prepare the compound (38) eliminating the group protecting the carboxyl group of the compound (37). The method of removing the protecting group varies depending on the kind of protecting group and can be carried out according to the methods usually used, for example, the methods described in Protective Groups in Organic Synthesis, Second Edition (1991, Green and co-authors). In case the protective group is a diphenylmethyl group, catalytic reduction is carried out; acids such as acetic acid and trifluoroacetic acid are used, or a complex of boron trifluoride diethyl ether is used. If the protecting group of the carboxyl group is a benzyl group, the catalytic reduction is carried out and in case the protective group is an alkyl group, such as methyl and ethyl, the hydrolysis is carried out.

STEP J-5 The present step is to prepare the compound (lj) of the present invention, by reacting the compound (38) with a reagent to remove the tert-butoxycarbonyl group and the isopropylidene group in an inert solvent. The next step can be carried out in a manner similar to the procedures in step E-2. The compound (1) of neuraminic acid thus obtained, or its salt, can be converted, if necessary, to other pharmacologically acceptable salts.

The neuraminic acid compound (1) of the present invention is subjected to hydrolysis by the hydrolase present in a living body and exhibits excellent viral reproduction inhibiting activity and excellent sialidase inhibitory activity. In addition, if the neuraminic acid compound (1) is administered to mice infected with the influenza virus, the compound exhibits therapeutic effects against infection, superior to those of the compound A (GG-167) described in WO 91/16320 ( Japanese patent application of the TCP (Kokai) No. Hei 5-507068). Thus, the neuraminic acid compound (1) of the present invention is useful as a therapeutic agent or as a prevention agent (preferably as a therapeutic agent) for viral infections (preferably infections by influenza viruses). The administration form of the neuraminic acid compound of the present invention includes, for example, oral administration or intranasal administration by solutions, such as liquid agents, aqueous cosolvents, etc., aerosols, powders, etc. From these preparations the solutions are prepared, as liquid agents and as aqueous cosolvents, by well known methods using purified water, pharmacologically acceptable organic solvents (for example, ethanol, propylene glycol, PEG 400, etc.) and stabilizers (for oxybenzoates, such as methylparaben and propylparaben, alcohols such as chlorobutane, benzyl alcohol and phenylethyl alcohol, benzalkonium chloride, phenols as phenol and cresol; thimerosal; dehydroacetic acid, etc.). The aerosols are prepared by well-known methods using a propellant, for example, the various kinds of Freon gases and nitrogen gas, and a surfactant, such as lecithin. The powders are prepared by well-known methods, using excipients (for example, organic excipients such as sugar, for example, lactose, sucrose, glucose, mannitol and sorbitol; starches, for example, corn starch, potato starch, α-starch, dextrin and carboxymethyl starch, celluloses, for example, crystalline cellulose, substituted hydroxypropylcellulose, lower substituent, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylcellulose, calcium carboxymethylcellulose and sodium carboxymethylcellulose, with internal bridge, gum arabic, dextran and pullulan, as well as inorganic excipients such as silicates , for example, light silicic anhydride, synthesized aluminum silicate and magnesium aluminate metasilicate, phosphates, eg, calcium phosphate, carbonates, eg, calcium carbonate, and sulfates, eg, calcium sulfate); lubricants (for example, stearic acid, metallic salts of stearic acid, such as calcium stearate and magnesium stearate, talc, colloidal silica, waxes, such as bee gum and spermaceti, boric acid, adipic acid, sulfates, for example, sulphate sodium, glycol, furmalic acid, sodium benzoate, DL-leucine, sodium salt of fatty acid, lauryl sulfates such as sodium lauryl sulfate and magnesium lauryl sulfate; silicic acid and silicic anhydride, as well as silicic acid hydrate; and the previous starches); stabilizers (paraoxybenzoates, such as methyl paraben and propylparaben, alcohols such as chlorobutanol, benzyl alcohol and phenylethyl alcohol, benzalkonium chloride, phenols such as phenol and cresol, thimerosal, dehydroacetic acid and sorbic acid), corrigents (eg, sweeteners, vinegars, perfumes, etc.) ., usually employees); diluents, etc. Although the dose of the active ingredients will vary depending on the conditions of the disease, the age of the patient, the methods of administration, etc., for example, in the case of solutions, it is convenient to administer the active ingredient in an amount of 0.1. mg (preferably 1 mg) as the lower limit and 1000 mg (preferably 500 mg) as the upper limit; in the case of dry powders, it is convenient to administer the active ingredients in an amount of 0.1 mg (preferably 1 mg) as the lower limit and 1000 mg (preferably 500 mg) as the upper limit; and in the case of aerosols, it is convenient to administer the active ingredient in an amount of 0.1 mg (preferably 1 mg) as the lower limit and 1000 mg (preferably 500 mg) as the upper limit; once or several times a day, in the previous administration methods, depending on the condition of the disease.

THE BEST WAY TO PUT THE INVENTION INTO PRACTICE The present invention will be described in greater detail by way of examples. The preparation examples and the test examples that follow are merely examples and do not limit the scope of the present invention to them.

EXAMPLE 1 Salt of trifluoroacetic acid of 5-acetamido-2,3,4-tetradeoxy-4-quanidino-d-cricer-d-cralacto-non-2-enopyranosoate myristyl (E8) (exemplary compound No. 88) (i) 5-Acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-O-isopropyl-iden-D-cricer-D-cralacto-non-2-enopiranosoate methyl (E3) dissolved 1.3 g (2.8 mmol) of 5-acetamido-7, 8, 9-tri-0-acetyl-4-azido-2, 3,4, 5-tetradeoxy-D-glycero-D-galacto-non-enopyranosonate from methyl (El) (which was synthesized according to the procedures described in Mark von Itzstein and coauthors, Carbohydr., Res., 244, 181-185 (1993) and Carbohyd, Res. 259, 293-299 (1993)) in 26 ml (20 times the volume), at room temperature; and a catalytic amount of sodium methoxide was added to the system, under the same conditions, and then the mixture was further stirred for 1 hour. After confirming that the reaction was completed, Dowex-50x8 (H +) was added to neutralize the mixture. The reaction mixture was filtered and the filtered product was washed with methanol. The filtrate and washing water were distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60, 100 g, methylene chloride: methanol = 5: 1) to obtain 620 mg (yield 66%) of compound (E2) as pale yellow solid. Rf value: 0.3 (methylene chloride: methanol = 5: 1) 580 mg (1.8 mmol) of the resulting compound (E2) was dissolved in 29 ml (50 times the volume) of acetone, at room temperature; and subsequently 0.7 ml (5.2 mmol) of 2,2-dimethoxypropane and 42 mg (0.18 mmol) of DL-10-alkylphosphonic acid were added to the system, while cooling with ice, and then the mixture was stirred at room temperature during 1 hour. After confirming that the reaction was complete, triethylamine was poured into the system to neutralize the mixture. The reaction mixture was distilled under reduced pressure and the residue was purified by column chromatography on silica gel (60 Kiesel gel, 60 g, benzene: ketonitrile = 1: 1) to obtain 540 mg (yield 84%) of the title (E3), as a white solid. Rf value: 0.76 (benzene: acetonitrile = 1: 1) NMR with (270 MHz, CDC13, TMS): d (ppm) 5.97 (ΔH, d, J = 2.4 Hz), 5.63 (HH, d, J = 7.1 Hz), 4.36 (HH, ddd, J = 7.9, 6.4, 4.8 Hz), 4.30-4.00 (6H, m), 3.81 (3H, s), 3.57 (HH) , dd, J = 7.9, 5.3 Hz), 2.12 (3H, s), 1.40 (3H, s), 1.3 (3H, s). [at 24 D = + 122.4 ° (c = 1.0 CHC13) (ii) 5-Acetamido-4-azido-2, 3, 4, 5-tetradeoxy-8, 9-O-iso-propylidene-D-glycero-D-galacto-non-2-enopyranosoic acid (E4) It was dissolved 460 mg (1.2 mmol) of the compound (E3) in 24 ml (30 times the volume) of methanol at room temperature, and subsequently 2.9 ml (1.4 mmol) of 1 molar aqueous solution of sodium hydroxide was added to the system, the ambient temperature, and then the mixture was stirred at room temperature for 1 hour. After confirming that the reaction was complete, it was added to the Dowex-50W system to neutralize the mixture. The reaction mixture was filtered and the filtrate was washed with water. The filtrate and the washing solution were combined and distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel gel 60, 60 g, ethyl acetate: 2-propanol: water = 2: 2: 1) to obtain 0.44 g (100% yield) of the title compound (E4), as a white solid. Rf value: 0.25 (ethyl acetate: 2-propanol: water = 2: 2: 1) NMR with (270 MHz, CDCl 3, TMS): d (ppm) 5.72 (H, d, J = 2.1 Hz), 4.37 ( HH, dt, J = 8.8, 5.5 Hz), 4.27 (HH, dd, J = 6.9, 1.4 Hz), 4.20-4.04 (3H, m), 4.00 (HH, dd, J = 8.8, 5.0 Hz), 3.54 (ÍH, d, J = 8.8 Hz), 2.03 (3H, s), 1.37 (3H, s), 1.32 (3H, s); MD24 = + 43.4 ° (c = 0.53 MeOH) (iii) 5-acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-O-iso-propylidene-D-cricer-D-qalacto-non-2-enistiranosoate myristyl (E5) dissolved 460 mg (1.2 mmol) d- = 1 compound (E4), 530 mg (2.5 mmol) of myristyl alcohol and 510 mg (1.9 mmol) of 2-bromo-l-ethylpyridinium tetrafluoroborate, in 22 ml (50 times the volume) of formamide. Subsequently, 0.9 ml (3.8 mmol) of tri-n-butylamine was poured into the system, and the mixture was stirred in an oil bath at 50 ° C for 6 hours. The reaction mixture was separated with ethyl acetate and a saturated aqueous solution of sodium chloride, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered, after which it was subjected to distillation under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel 60 gel, 100 g, benzene: ethyl acetate = 1: 1) to obtain 0.19 g (28% yield) of the title compound (E5), as a solid. White. Rf value: 0.4 (benzene: ethyl acetate = 1: 1) NMR with (270 MHz, CDC13, TMS): d (ppm) 5.95 (ΔI, d, J = 2.4 Hz), 5.60 (1H, d, J = 7.0 Hz), 4.36 (HH, dt, J = 7.7, 5.7 Hz), 4.30-4.00 (8H, m), 3.58 (HH, d, J = 7.7 Hz), 2.12 (3H, s), 1.69 (2H, quintuple band, J = 6.3 Hz), 1.40 (3H, s), 1.35 (3H, s), 1.26 (22H, broad s), 0.88 (3H, t, J = 6.3 Hz). [a.] D24 = +83. 3 ° (c = 0. 54 CHCI3) (iv) 5-acetamido-4-amino-2,3,4,5-tetradeoxy-8,, 9--0- -iso-propyl: Lden- -D- -ql. icero-D-cralacto- -non- 2 - enop. myristosium myristosate (E6) 134 mg (0.24 mmol) of the compound (E5) was dissolved in 6.7 ml (50 times by volume) ethanol at room temperature, and subsequently 47 mg (0.35 times the volume) was added to the system of Lindlar catalyst, at room temperature, and then the mixture was stirred at room temperature under a hydrogen atmosphere, under pressure of one atmosphere, for 2 hours. After it was confirmed that the reaction was complete, the reaction mixture was filtered and the filtrate was washed with ethanol. The filtrate and wash solution were combined and subjected to distillation under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (60 Kiesel gel, 60 g, ethyl acetate: 2-propanol.-Water = 5: 2: 1) to obtain 0.11 g (88% yield) of the compound of the title (E6), as a white solid. Rf value: 0.28 (ethyl acetate: 2-propanol: water = 8: 2: 1) NMR with ^ -H (270 MHz, CD3OD, TMS): d (ppm) 5.93 (H, d, J = 2.6 Hz) , 4.31 (ÍH, quintuple band, J = 6.9 Hz), 4.23-3.93 (5H, m), 3.88 (1H, t, J = 9.0 Hz), 3.67-3.50 (2H, m), 2.05 (3H, s) , 1.68 (2H, quintuple band, J = 8.1 Hz), 1.37 (3H, s), 1.27 (22H, broad s), 0.88 (3H, t, J = 8.1 Hz). (v) 5-Acetamido-4- (N, N * -bis-tert-butoxycarbonyl c-Rriadino-2,3,4,5-tetradeoxy-8, 9-O-isopropylidene-D-glycero-D-cralacto- myristyl non-2-enopyranosoate (E7) 110 mg (0.21 mmol) of the compound (E6), 72 mg (0.26 mmol) of N, N'-bis-tert-butoxycarbonyl thiourea and 80 ml were dissolved (0.57 mmol) of triethylamine in 22 ml (50 times the volume) of dimethylformamide, at room temperature. Subsequently, 70.5 mg (0.26 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and the mixture was filtered using Celite, and the filtrate was washed with ethyl acetate. The filtrate thus obtained and the wash solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added to the mixture and then separated. The organic layer was dried over magnesium sulfate and filtered, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel 60 gel, 100 g, hexane-ethyl acetate = 3: 2) to obtain 120 mg (71% yield) of the title compound (E7), as a solid white. Rf value: 0.65 (hexane: ethyl acetate = 3: 2) NMR with U (270 MHz, CDC13, TMS): d (ppm) 11.4 (OH, s), 8.63 (OH, d, J = 7.8 Hz), 7.99 (1H, d, J = 4.8 Hz), 5.78 (ΔI, d, J = 2.4 Hz), 5.32 (1H, d, J = 4.4 Hz), 5.14 (ΔI, tt, J = 7.8, 1.6 Hz), 4.40 (ÍH, dt, - 1 = 10.6, 4.8 Hz), 4.33-3.90 (6H, m), 3.52 (ÍH, dd, J = 8.7, 3.9 Hz), 2.02 (3H, s), 1.64 (2H, m), 1.52 (9H, s), 1.49 (9H, s), 1.43 (3H, s), 1.36 (3H, s), 1.26 (22H, broad s), 0.88 (3H, t, J = 6.7 Hz); [QÍ] D24 = -20.9 ° (c = 0.58 CHC13). (vi) Trifluoroacetic acid salt of 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-D-glycero-D-galacto-non-2-enopyran-myristyl-soato (E8) 84 mg was dissolved (0.11 mmol) of the compound (E7) eh 4.7 ml (50 times the volume) of methylene chloride at room temperature, and 0.85 ml (10 times the volume) of trifluoroacetic acid was subsequently added to the system, at room temperature, after which the mixture was stirred at room temperature for 22 hours. After it was confirmed that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel gel 60, 15 g, ethyl acetate: 2-propanol: water = 8: 2: 1) to obtain 82 mg (88% yield) of the title compound ( E8) as a white solid. Rf value: 0.66 (ethyl acetate: 2-propanol: water = 8: 2: 1) 1 H NMR (270 MHz, CD3OD): d (ppm) 5.83 (ΔH, d, J = 2.7 Hz), 4.44 (1H , dd, J = 9.0, 2.7 Hz), 4.38 (HH, dd, J = 9.0 <1H), 4.18 (2H, t, J = 6.2 Hz), 4.17 (HH, t, J = 9.0 Hz), 3.90 -3.74 (2H, m), 3.68 (1H, dd, J = 12.0, 4.5 Hz), 3.65 (HI, d, J = 9.0 Hz), 1.99 (3H, s), 1.67 (2H, quintuple band, J = 6.2 Hz), 1.26 (24H, s broad), 0.87 (3H, t, J = 6.2 Hz); FAB-MS (positive): 529 (M + H) + HR-MS: calculated for C26H49N4O7 529.3597, found: 529. 3605 (M + H) +.

EXAMPLE 2 Salt of trifluoroacetic acid of 5-acetamido-2,3, 4,5-tetradeoxy-4-quanidino-d-qicero-d-qalacto-non-2-enopyranosoate hexyl (E12) (exemplary compound No. 87) (i) 5-acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-O-iso-propylidene-D-cricer-Dg-alacto-non-2-hexyl enopyranosoate (E9) dissolved 940 mg (2.6 mmol) of compound (E4), 0.66 ml (5.3 mmol) of 1-hexanol and 1.1 g (4.0 mmol) of 2-bromo-l-ethylpyridinium tetrafluoroborate, in 47 ml (50 times the volume) of dimethylformamide, at room temperature. Subsequently, 1.9 ml (8.0 mmol) of tri-n-butylamine was poured into the system, and the mixture was stirred in an oil bath at 50 ° C for 6 hours. To the reaction mixture was added ethyl acetate and a saturated aqueous solution of sodium chloride, and the mixture was separated. The layer was dried organic medium thus obtained over magnesium sulfate and filtered, after which it was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel 60 gel, 150 g, benzene: acetonitrile = 2: 1) to obtain 560 mg (44% yield) of the title compound (E9), as a pale brown solid. . Rf value: 0.43 (benzene: acetonitrile = 2: 1) NMR with ΔR (270 MHz, CDC13, TMS): d (ppm) 6.53 (ΔH, d, J = 6.9 Hz), 5.92 (HH, d, J = 2.5 Hz), 4.48 (HH, broad), 4.41-4.29 (2H, m), 4.24-4.00 (7H, m), 3.63 (1H, broad d, J = 7.3 Hz), 1.70 (2H, quintuple band, J = 6.5 Hz), 1.40 (3H, s), 1.35 (9H, broad s), 1.30 (3H, s), 0.89 (3H, t, J = 6.5 Hz). [Q.] D24 = + 8 ° (c = 0.4 CHCI3). (ii) 5-Acetamido-4- (N, N'-bis-tert-butoxycarbonyl) -cucanidino-2,3,4,5-tetradeoxy-8, 9-O-isopropylidene-D-cricer-D-qalacto-non -2-hexyl enopyranosoate (Eli) 533 mg (1.1 mmol) of compound (E9) was dissolved in 25 ml (50 times the volume) of ethanol, at room temperature, and 190 mg (0.35 times) was subsequently added to the system. the volume) of Lindlar catalyst, at room temperature, after which the mixture was stirred at room temperature under a hydrogen atmosphere, under a pressure of 1 atmosphere, for 2.5 hours. After confirming that the reaction was complete, the reaction mixture was filtered. The filtered product was washed with ethanol and combined the filtrate and wash solution, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 50 g, ethyl acetate: 2-propanol: water = 5: 2: 1) to obtain 303 mg (yield 60%) of the title compound ( E10), like a pale coffee foamy solid. Rf value: 0.44 (ethyl acetate: 2-propanol: water = 5: 2: 1) 290 mg (0.63 mmol) of the resulting compound (E10), 210 mg (0.75 mmol) of N, N '-bis- was dissolved. tert-butoxycarbonyl thiourea and 22 ml (1.6 mmol) of triethylamine in 152 ml (50 times the volume) of dimethyl ormamide, at room temperature. Subsequently, 220 mg (0.8 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and filtered using Celite, and the filtered product was washed with ethyl acetate. The filtrate thus obtained and the washing solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added to the mixture to separate the mixture, after which the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 75 g, hexane: ethyl acetate = 1: 1) to obtain 273 mg (66% yield) of the title compound (Eli), as a solid White.

Rf value: 0.38 (benzene: ethyl acetate = 5: 1) NMR with XH (270 MHz, CDC13, TMS): d (ppm) 11.4 (1H, s), 8.64 (HH, d, J = 7.7 Hz), 7.99 (HH, d, J = 4.7 Hz), 5.78 (HH, d, J = 2.4 Hz), 5.33 (HH, d, J = 4.4 Hz), 5.14 (HH, tt, J = 7.9, 1.6 Hz), 4.40 (HH, dt, J = 7.8, 5.7 Hz), 4.23-3.90 (7H, m ), 3.51 (ÍH, dd, J = 8.2, 4.5 Hz), 2.01 (3H, s), 1.68 (2H, quintuple band, J = 6.4 Hz), 1.51 (9H, s), 1.49 (9H, s), 1.43 (3H, s), 1.36 (3H, s), 1. 35-1.20 (6H, m), 0.89 (3H, t, J = 6.4 Hz). [a;] D24 = -22.0 ° (c = 0.5 CHCI3). (iii) Trifluoroacetic acid salt of 5-acetamido-2,3,4,5-tetradeoxy-4-a / uanidino-D-cricer-Da: hexyl-alato-non-2-enopyran-soato (E12) It was dissolved 158 mg (0.24 mmol) of the compound (Eli) in 8.0 ml (50 times the volume) of methylene chloride at room temperature, and subsequently added to the system 1.6 ml (10 times the volume) of trifluoroacetic acid, at the temperature environment, after which the mixture was stirred at room temperature for 18 hours. After it was confirmed that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel gel 60, 15 g, ethyl acetate: 2-propanol: water = 5: 2: 1) to obtain 155 mg (100% yield) of the title compound ( E12) as a white solid. Rf value: 0.8 (ethyl acetate: 2-propanol: water = 5: 2: 1) NMR with (270 MHz, CD3OD): d (ppm) 5.9-4 (ΔI, d, J = 2.4 Hz), 4.46 (1H, dd, J = 9.3, 2.4 Hz), 4.38 (ΔI, dd, J = 10.4 , 1.3 Hz), 4.20 (2H, t, J = 9.3 Hz), 4.20 (2H, t, J = 6.2 Hz), 3.91-3.76 (2H, m), 3.66 (ÍH, broad d, J = 9.3 Hz) , 3.61 (ÍH, dd, J = 12.5, 6.3 Hz), 1.97 (3H, s), 1.63 (2H, quintuple band, J = 6.3 Hz), 1.40-1.10 (6H, m), 0.80 (3H, t, J = 6.3 Hz). [Q.] D24 = + 18.1 ° (c = 0.48 CHCI3).

EXAMPLE 3 Salt of trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-0-myristoyl-d-qlycero-d-qalacto-non-2-enopyranosoic acid (E17) (compound copy No. 41) (i) 5-Acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-O-iso-propylidene-7-0-myristoyl-D-cricer-D-qalacto-non-2-enopyranosoate of methyl (E13) 61 mg (0.16 mmol) of the compound (E3) was dissolved in 3.0 ml (50 times the volume) of methylene chloride, at room temperature, and subsequently 54 ml (0.2 mmol) of myristoyl chloride and 24.1 mg (0.2 mmol) of 4-dimethylaminopyridine, while cooling with ice, after which the mixture was stirred at room temperature for 30 minutes. Then, 27 ml (0.2 mmol) of triethylamine was poured into the reaction mixture at room temperature, and then the mixture was further stirred for 6 hours. After confirming that the reaction was complete, methanol was poured into the system and the mixture was then stirred for 30 minutes. Then, ethyl acetate and a saturated aqueous solution of sodium chloride were added to the reaction mixture to separate the mixture. The organic layer thus obtained was dried over magnesium sulfate and filtered and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 15 g, benzene: ethyl acetate = 1: 1) to obtain 70 mg (yield 74%) of the desired compound (E13), as a clear syrup colorless. Rf value: 0.42 (benzene: ethyl acetate = 2: 1) 1 H NMR (270 MHz, CDC13, TMS): d (ppm) 5.95 (ΔH, d, J = 2.7 Hz), 5.88 (ÍH, d, J = 7.9 Hz), 5.35 (1H, dd, J = 6.0, 1.8 Hz), 4.80 (1H, dd, J = 9.1, 2.7 Hz), 4.71 (ÍH, dd, J = 10.5, 1.8 Hz), 4.39 (HH, c, J = 6.0 Hz), 4.14 (1H, dd, J = 8.8, 6.0 Hz), 4.71 (HH, dd, J = 10.5, 1.8 Hz), 4.39 (1H, c, J = 6.0 Hz) , 4.14 (HH, dd, J = 8.8, 6.0 Hz), 3.945 (1H, dd, J = 8.8, 6.0 Hz), 3.81 (3H, s), 3.45 (HH, ddd, J = 10.5, 9.1, 7.9 Hz ), 2.41 (HH, t, J = 7.5 Hz), 2.39 (HH, t, J = 7.5 Hz), 2.02 (3H, s), 1.63 (2H, quintuple band, J = 7.5 Hz), 1.37 (3H, s), 1.35 (3H, s), 1.26 (20H, s =, 0.88 (3H, t, J = 7.5 Hz). (ii) 5-acetamido-4-amino-2, 3,4,5-tetradeoxy-8, 9-0-iso-propylidene-7-Q-myristoyl-Dq, licero-D-cfalacto-non-2-enopiranosoate of methyl (E14) 70 mg (0.12 mmol) of the compound (E13) was dissolved in 3.5 ml (50 times the volume) of ethanol, at room temperature, and subsequently 25 mg (0.35 times the volume) of the mixture was added to the system. Lindlar catalyst, at room temperature, after which the mixture was stirred at room temperature under a hydrogen atmosphere, under a pressure of 1 atmosphere, for 1.5 hours. After confirming that the reaction was complete, the reaction mixture was filtered. The filtrate was washed with ethanol and the filtrate and washing solution were combined, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 15 g, ethyl acetate: 2-propanol: water = 5: 2: 1) to obtain 57 mg (yield 84%) of the title compound ( E14), as a white solid. Rf value: 0.49 (methylene chloride: methanol = 10: 1) 1 H NMR (270 MHz, CD3OD, TMS): d (ppm) 5.94 (ΔI, d, J = 2.4 Hz), 5.42 (HH, dd, J = 4.7, 1.8 Hz), 4.39 (HH, dt, J = 7.1, 6.0 Hz), 4.18 (HH, dd, J = 9.5, 1.6 Hz), 4.14 (HH, dd, J = 8.7, 6.4 Hz), 3.93 (1H, dd, J = 8.7, 6.4 Hz), 3.87 (ÍH, t, J = 9.5 Hz), 3.78 (3H, s), 3.44 (1H, dd, J = 9.5, 2.4 Hz), 2.35 (2H, c, J = 7.3 Hz), 1.94 (3H, s), 1.60 (2H, quintuple band, J = 7.3 Hz ), 1.32 (3H, s), 1.31 (3H, s), 1.27 (20H, s), 0.88 (3H, t, J = 7.3 Hz). (iii) 5-acetamido-4- (N, N'-bis-tert-butoxycarbonyl) quanidino-2,3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-myristoyl-D-qlicero -D-galacto-non-2-enopyranosoate methyl (E15) 57 mg (0.1 mmol) of compound (E14), 34 mg (0.12 mmol) of N, N '-bis-tert-butoxycarbonyl thiourea and 35 ml was dissolved (0.25 mmol) of triethylamine in 28 ml (50 times the volume) of dimethylformamide, at room temperature. Subsequently, 35 mg (0.13 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and the mixture was filtered using Celite. The filtrate was washed with ethyl acetate. The filtrate thus obtained and the washing solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added to the mixture to separate it. The organic layer was dried over magnesium sulfate and filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (60 Kiesel gel, 15 g, hexane: ethyl acetate = 2: 1) to obtain 75 mg (100% yield) of the title compound, as a clear, colorless syrup. . Rf value: 0.33 (hexane: ethyl acetate = 2: 1) NMR with (270 MHz, CDC13, TMS): d (ppm) 11.4 (1H, s), 8.46 (H, d, J = 8.7 Hz), 6.06 (HH, d, J = 8.7 Hz), 5.88 (HH, d, J = 2.4 Hz), 5.37 (HH, dd, J = 6.4, 1.5 Hz), 5.15 (HH, dt, J = 8.7, 2.4 Hz) , 4.38 (H, c, J = 6.4 Hz), 4.28 (H, d, J = 8.7, 1.5 Hz), 4.23 (HH, t, J = 8.7 Hz), 4.10 (HH, dd, J = 9.6, 6.4 Hz), 3.95 (HH, dd, J-9.6, 6.4 (Hz), 3.80 (3H, s), 2.453 (HH, dt, J = 16.0, 7.5 Hz), 2.33 (HH, dt, J = 16.0, 7.5 Hz), 1.87 (3H, s), 1.61 (2H, quintuple band, J = 7.5 Hz), 1.49 (9H , s), 1.48 (9H, s), 1.38 (3H, s), 1.35 (3H, s), 1.25 (20H, broad s), 0.88 (3H, t, J = 7.5 Hz). (iv) 5-Acetamido-4- (N, N * -bis-tert-butoxycarbonyl) guanidino-2, 3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-myristoyl-D- acid glycero-D-galacto-non-2-enopyranosoic (El) 51 mg (0.07 mmol) of the compound (E15) was dissolved in a mixture of 2 ml (40 times the volume) of methanol and 0.5 ml (10 times the volume) of water, and subsequently 3.3 mg (0.078 mmol) of lithium hydroxide monohydrate was added to the system at room temperature, and then the mixture was stirred at room temperature for 8 hours. After confirming that the reaction was completed, Dowex-50W was added to the system to neutralize the mixture. The reaction mixture was filtered and the filtered product was washed with methanol. The filtrate and wash solution were combined and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 60 g, ethyl acetate: 2-propanol: water = 10: 2: 1) to obtain 33 mg (66% yield) of the desired compound (E16) as a white solid. Rf value: 0.45 (methylene chloride: methanol = 10: 1) 1 H-NMR (270 MHz, CDCl 3, TMS): d (ppm) 11.4 (1H, s), 8.48 (ÍH, d, J = 8.0 Hz), 6.31 (ÍH, s mate), 5.90 (ÍH, s broad), 5.30 (ÍH, s broad), 5.10 (ÍH, s broad), 4.60-3.30 (7H, m ), 2.48 (ΔI, dt, J = 13.5, 6.5 Hz), 2.32 (ΔI, dt, J = 13.5, 6.5 Hz), 1.88 (3H, s), 1.60 (2H, quintuple band, J = 6.5 Hz), 1.48 (18H, s), 1.39 (3H, s), 1.37 (3H, s), 1.25 (20H, broad s), .0.88 (3H, t, J = 6.5 Hz). (v) Salt of the trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-0-myristoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (El7) dissolved 33 mg (0.046 mmol) of the compound (E16) in 1.6 ml (50 times the volume) of methylene chloride at room temperature and subsequently 60 ml (10 times the volume) of trifluoroacetic acid was added to the system at the temperature environment, and then the mixture was stirred at room temperature for 22 hours. After confirming that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60.5 g, 2-propanol: water = 5: 1) to obtain 30 mg (yield 84%) of the title compound (E17) as a yellow solid. pale. Rf value: 0.4 (2-propanol: water = 5: 1) 1 H NMR (270 MHz, CD3OD): d (ppm) 5.63 (ΔI, d, J = 2.3 Hz), 4.49 (ΔI, dd, J = 9.3 , 2.3 Hz), 4.39 (ÍH, d, J = 10.6 Hz), 4.25-4.00 (4H, m), 3.77 (? H, d, J = 9.3 Hz), 2.36 (2H, t, J = 7.4 Hz) , 1.92 (3H, s), 1.70-1.50 (2H, m), 1.30 (20H, broad S), 0.90 (3H, t, J = 7.4 Hz); FAB-MS (positive): 543 (M + H) +; HR-MS calculated for C26H47? 8N 543.3378, found: 543.3412 (M + H) +; [allo24 = + 25 ° (c = 0.12, MeOH).

EXAMPLE 4 Salt of trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-o-hexanoyl-d-qlycero-d-qalacto-non-2-enopyranosoic acid (E22) (compound copy No. 36) (i) 5-acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-O-isopropyl-iden-7-0-hexanoyl-D-qlicero-D-galacto-non-2-enopiranosoate of methyl (E18) 270 mg (0.73 mmol) of compound (E3) was dissolved in 13.5 ml (50 times the volume) of methylene chloride and subsequently 0.14 ml (1.0 mmol) of hexanoyl chloride and 110 mg were added to the system. (0.9 mmol) of 4-dimethylaminopyridine, while cooling with ice, and then the mixture was stirred at room temperature for 30 minutes. Then 0.13 ml (0.9 mmol) of triethylamine was poured into the reaction mixture at the temperature environment, and then the mixture was further stirred for 19 hours. After it was confirmed that the reaction was complete methanol was poured into the system, and then the mixture was stirred for 30 minutes. Then, ethyl acetate and an aqueous solution of sodium chloride were added to the reaction mixture to separate the mixture. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (Kiesel gel 60, 75 g, benzene: ethyl acetate = 1: 1) to obtain 220 mg (yield 74%) of the title compound (E18) as a transparent syrup, colorless. Rf value: 0.45 (benzene: ethyl acetate = 1: 1) NMR with (270 MHz, CDCl3, TMS): d (ppm) 6.11 (ΔI, d, J = 8.0 Hz), 5.95 (ΔI, d, J = 2.6 Hz), 5.38 (ÍH, d, J = 5.3, 2.0 Hz), 4.69 (HH, dd, J = 9.2, 2.6 Hz), 4.65 (HH, dd, J = 10.6, 2.0 Hz), 4.38 (ÍH, c, J = 5.5 Hz), 4.14 (ÍH, dd, J = 9.5, 5.5 Hz), 3.95 (ÍH, dd, J = 9.5, 5.4 Hz), 3.81 (3H, s), 3.59 (ÍH, ddd, J = 10.6, 9.2, 8.0 Hz), 2.44 (HH, dt, J = 15.9, 7.4 Hz), 2.36 (HH, dt, J = 15.9, 7.4 Hz), 2.01 (3H, s), 1.64 (2H, quintuple band, J = 7.4 Hz) , 1.37 (3H, s), 1.35 (3H, s), 1.35-1.30 (4H, m), 0.90 (3H, t, J = 7.4 Hz); [a.] D24 = + 94.3 ° (c = 0.35, CHCI3). (ii) 5-acetamido-4- (N, N'-bis-tert-butoxycarbonyl) guanidino-2,3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-hexanoyl-D-qlicero -D-galacto-non-2-enopyranosoate methyl (E20) 190 mg (0.41 mmol) of the compound (E18) was dissolved in 9.3 ml (50 times the volume) of ethanol, at room temperature, and subsequently added to the 70 mg system (0.38 times the volume) of Lindlar catalyst, at room temperature, after which the mixture was stirred at room temperature under a hydrogen atmosphere, at a pressure of 1 atmosphere, for 2.5 hours. After confirming that the reaction was complete, the reaction mixture was filtered. The filtrate was washed with ethanol and the filtrate and washing solution were combined, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (60 Kiesel gel, 60 g, ethyl acetate: 2-propanol.-Water = 5: 2: 1) to obtain 140 mg (yield 80%) of the title compound (E19), as a pale yellow foamy solid. Rf value: 0.4 (ethyl acetate: 2-propanol = 5: 2: 1) 140 mg (0.3 mmol) of the resulting compound (E19), 120 mg (0.43 mmol) of N, N'-bis-ter- was dissolved. butoxycarbonyl thiourea and 0.12 ml (0.86 mmol) of triethylamine in 7 ml (50 times the volume). of dimethylformamide, at room temperature. Subsequently, 110 mg (0.41 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature. for 1.5 hours. The reaction mixture was diluted with ethyl acetate and the mixture was filtered using Celite, after which the filtered product was washed with ethyl acetate. The filtrate and wash solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added thereto to separate it. The organic layer was dried over magnesium sulfate and filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (60 Kiesel gel, 50 g, benzene: ethyl acetate = 3: 1) to obtain 220 mg (100% yield) of the title compound (E20), as a white foamy solid. Rf value: 0.5 (benzene: ethyl acetate = 3: 1) NMR with (270 MHz, CDCl 3, TMS): d (ppm) 11.4 (OH, s), 8.46 (1H, d, J = 8.7 Hz), 5.97 (H, D, J = 8.7 Hz), 5.88 (H, D, J = 2.3 Hz), 5.37 (HH, dd, J = 6.3, 1.6 Hz), 5.15 (HH, dt, J = 8.7, 2.3 Hz), 4.37 (H, c, J = 6.4 Hz), 4.29 (H, d, J = 8.7, 1.5 Hz), 4.24 (H, t, J = 8.7 Hz), 4.11 (H, d, J = 8.8 , 6.4 Hz), 3.96 (ÍH, dd, J = 8.8, 6.4 (Hz), 3.81 (3H, s), 2.46 (IH, dt, J = 15.9, 7.4 Hz), 2.33 (IH, dt, J = 15.9, 7.4 Hz), 1.88 (3H, s) , 1.70-1.50 (2H, m), 1. 49 (9H, s), 1.48 (9H, s), 1.38 (3H, s), 1.37 (3H, s), 1.40-1.25 (4H, m), 0.89 (3H, t, J = 7.4 Hz). [a;] D24 = -28.3 ° (c = 0.4, CHCl3). (iii) 5-Acetamido-4- (N, N'-bis-tert-butoxycarbonyl) quanidino-2, 3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-hexanoyl-D- acid q-glycero-D-galacto-non-2-enopyranosoic acid (E21) 180 mg (0.26 mmol) of the compound (E20) was dissolved in a mixture of 10.8 ml (60 times the volume) of methanol and 1.8 ml (10 times the volume) of water, and 12 mg was added to the system (0.29 mmol) of lithium hydroxide monohydrate, at room temperature, and then the mixture was stirred at room temperature for 17 hours. After confirming that the reaction was complete, Dowex-50W was added to the system to neutralize the mixture. The reaction mixture was filtered and the filtered product was washed with methanol. The filtrate and wash solution were combined and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (60 Kiesel gel, 50 g, methylene chloride: methanol = 10: 1) to obtain 0.13 g (yield 75%) of the desired compound (E21) as a white foamy solid. Rf value: 0.24 (methylene chloride: methanol = 10: 1) NMR with 1H (270 MHz, CDC13, TMS): d (ppm) 11.4 (H, broad), 8.52 (H, broad), 5.95 (2 H) , broad), 5.32 (wide), 5.15 (wide), 4.60-4.10 (3H, m), 3.95 (1H, broad), 2.70-2.20 (2H, m), 1.89 (3H , s), 1.75-1.00 (28H, m), 0.85 (3H, m). (iv) Salt of the trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-0-hexanoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (E22) dissolved 95 mg (0.15 mmol) of the compound (E21) in 4.8 ml (50 times the volume) of methylene chloride and subsequently 0.95 ml (10 times the volume) of trifluoroacetic acid was added to the system, at room temperature, and then the mixture was stirred at room temperature for 4.5 hours. After confirming that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 20 g, ethyl acetate: 2-propanol: water = 4: 2: 1) to obtain 54 mg (yield 57%) of the desired compound as a white solid. Rf value: 0.3 (ethyl acetate: 2-propanol: water = 4: 2: 1) NMR with ^ -H (270 MHz, CD3OD): d (ppm) 5.53 (1H, d, J = 2.2 Hz), 4.50 -4.00 (6H, m), 3.59 (HH, d, J = 9.2 Hz), 2.35 (2H, t, J = 7.5 Hz), 2.01 (-3H, s), 1.70-1.50 (2H, m), 1.40 -1.20 (4H, m), 0.91 (3H, t, J = 7.5 Hz); IR (KBr) (CM-1) 333, 1665, 1617, 1401, 1385, 1176; FAB-MS (positive): 431 (M + H) +; HR-MS calculated for Cig ^ iOgNi 431.2165, found: 431.2125 (M + H) +; [a-] D24 = + 29 ° (c = 0.2, MeOH).

EXAMPLE 5 Salt of trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-o-octanoyl-d-qicers-d-qalacto-non-2-enopyranosoic acid (E22) (compound copy No. 36) (i) 5-acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-0-isopropyl-iden-7-0-myristoyl-D-qlicero-D-galacto-non-2-enopyranosoate of methyl (E23) 185 mg (0.5 mmol) of the compound (E3) was dissolved in 5.0 ml of methylene chloride, at room temperature, and subsequently 132 μl (0.75 mmol) of octanoyl chloride and 91 mg were added to the system. (0.75 mmol) of 4-dimethylaminopyridine, while cooling with ice, and then the mixture was stirred at room temperature for 30 minutes. Then 104 μl (0.75 mmol) of triethylamine was poured into the reaction mixture at room temperature, and then the mixture was further stirred for 6 hours. After it was confirmed that the reaction was complete methanol was poured into the system, and then the mixture was stirred for 30 minutes. Then, ethyl acetate and an aqueous solution of sodium chloride were added to the reaction mixture to separate the mixture. The layer was dried organic medium thus obtained over magnesium sulfate and filtered and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, methylene chloride: methanol = 50: 1) to obtain 150 mg (64% yield) of the title compound (E23) as a clear, colorless syrup. Rf value: 0.50 (methylene chloride: methanol = 20: 1); NMR with ^ -H (270 MHz, CDC13, TMS): d (ppm) 5.95 (H, d, J = 2.7 Hz), 5.88 (H, d, J = 7.9 Hz), 5.35 (H, d, J) 6.0, 1.8 Hz), 4.80 (H, d, J = 9.1, 2.7 Hz), 4.71 (H, d, J = 10.5, 1.8 Hz), 4.39 (1 H, c, J = 6.0 Hz), 4.14 (H, dd, J = 8.8, 6.0 Hz), 4.71 (HH, dd, J = 10.5, 1.8 Hz), 4.39 (HH, c, J = 6.0 Hz), 4.14 (HH, dd, J = 8.8, 6.0 Hz), 3.945 (HH, dd, J = 8.8, 6.0 Hz), 3.81 (3H, s), 3.45 (HH, ddd, J = 10.5, 9.1, 7.9 Hz), 2.41 (HH, t, J = 7.5 Hz), 2.39 (ÍH, t, J = 7.5 Hz), 2.02 (3H, s), 1.63 (2H, quintuple band, J = 7.5 Hz), 1.37 (3H, s), 1.35 (3H, s), 1.26 (8H, s ), 0.88 (3H, t, J = 7.5 Hz); (ii) 5-acetamido-4-amino-2, 3,4,5-tetradeoxy-8, 9-O-isopropyl-iden-7-0-octanoyl-D-qlicero-D-qalacto-non-2-enopiranosoate of methyl (E24) 130 mg (0.28 mmol) of the compound (E23) was dissolved in 6. 0 ml of ethanol, at room temperature, and subsequently 46 mg (0.35 times the volume) of Lindlar's catalyst was added to the system, at room temperature, after which the mixture was stirred at room temperature under hydrogen atmosphere, at a pressure of 1 atmosphere, for 1.5 hours. After confirming that the reaction was complete, the reaction mixture was filtered. The filtrate was washed with ethanol and the filtrate and washing solution were combined, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 15 g, ethyl acetate: 2-propanol: water = 5: 2: 1) to obtain 95 mg (yield 77%) of the title compound ( E24), as a white solid. Rf value: 0.35 (n-hexane: ethyl acetate = 2: 1) NMR with 1H (270 MHz, CD3OD, TMS): d (ppm): 5.94 (1H, d, J = 2.4 Hz), 5.42 (1H, dd, J = 4.7, 1.8 Hz), 4.39 (HH, dt, J = 7.1, 6.0 Hz), 4.18 (HH, dd, J = 9.5, 1.6 Hz), 4.14 (HH, dd, J = 8.7, 6.4 Hz ), 3.93 (HH, dd, J = 8.7, 6.4 Hz), 3.87 (HH, t, J = 9.5 Hz), 3.78 (3H, s), 3.44 (HH, dd, J = 9.5, 2.4 Hz), 2.35 (2H, c, J = 7.3 Hz), 1.94 (3H, s), 1.60 (2H, quintuple band, J = 7.3 Hz), 1.32 (3H, s), 1.31 (3H, s), 1.27 (8H, s ), 0.88 (3H, t, J = 7.3 Hz). (iii) 5-acetamido-4- (N, N'-bis-tert-butoxycarbonyl) guanidino-2,3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-octanoyl-D-glycero - D-galacto-non-2-enopyranosoate methyl (E25) 90 mg (0.2 mmol) of the compound (E24), 83 mg (0.30 mmol) of N, N'-bis-tert-butoxycarbonyl thiourea and 84 μl were dissolved. (0.25 mmol) of triethylamine in 5 ml of dimethylformamide, at room temperature. Subsequently, 82 mg (0.30 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and the mixture was filtered using Celite. The filtered product was washed with ethyl acetate. The filtrate thus obtained and the washing solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added thereto to separate it. The organic layer was dried over magnesium sulfate and filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel gel 60, 15 g, hexane: ethyl acetate = 2: 1) to obtain 120 mg (88% yield) of the title compound (E25), as a syrup. colorless transparent; Rf value: 0.30 (hexane: ethyl acetate = 2: 1) NMR with (270 MHz, CDC13, TMS): d (ppm) 11.4 (1H, s), 8.46 (H, d, J = 8.7 Hz), 6 . 06 (HH, d, J = 8.7 Hz), 5.88 (HH, d, J = 2.4 Hz), 5.37 (ÍH, dd, J = 6.4, 1.5 Hz), 5.15 (ÍH, dt, J = 8.7, 2.4 Hz), 4.38 (HH, c, J = 6.4 Hz), 4.28 (HH, dd, J = 8.7, 1.5 Hz), 4.23 (HH, t, J = 8.7 Hz), 4.10 (1H, dd, J = 9.6, 6.4 Hz), 3.95 (HH, dd, J = 9.6, 6.4 (Hz), 3.80 (3H, s), 2.453 (ΔI, dt, J = 16.0, 7.5 Hz), 2.33 (ΔI, dt, J = 16.0, 7.5 Hz), 1.87 (3H, s) , 1.61 (2H, quintuple band, J = 7.5 Hz), 1.49 (9H, s), 1.48 (9H, s), 1.38 (3H, s), 1.35 (3H, s), 1.25 (8H, s broad), 0.88 (3H, t, J = 7.5 Hz). (iv) 5-Acetamido-4- (N, N'-bis-tert-butoxycarbonyl) guanidino-2, 3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-octanoyl-D- acid glycero-D-galacto-non-2-enopyranosoic (E26) 100 mg (0.15 mmol) of the compound (E25) was dissolved in a mixture of 4 ml (40 times the volume) of methanol and 1 ml (10 times the volume) of water, and 7.0 mg (0.165 mmol) of lithium hydroxide monohydrate was added to the system at room temperature, and then the mixture was stirred at room temperature for 8 hours. After confirming that the reaction was complete, Dowex-50W was added to the system to neutralize the mixture. The reaction mixture was filtered and the filtered product was washed with methanol. The filtrate and wash solution were combined and concentrated under reduced pressure.

The residue was purified by column chromatography on silica gel (Kiesel 60 gel, ethyl acetate: 2-propanol: water = 10: 2: 1) to obtain 56 mg (56% yield) of the desired compound (E26) as a white solid. Rf value: 0.35 (methylene chloride: methanol = 10: 1) NMR with (270 MHz, CDC13, TMS): d (ppm) 11.4 (H, s), 8.48 (H, d, J = 8.0 Hz), 6.31 (ÍH, s mate) 5.90 (ÍH, s broad), 5.30 (ÍH, s broad), 5.10 (ÍH, s broad), 4.60-3.30 (7H, m), 2.48 (ÍH, dt, J = 13.5, 6.5 Hz), 2.32 (1H, dt, J = 13.5, 6.5 Hz <), 1.88 (3H, s), 1.60 (2H, quintuple band, J = 6.5 Hz), 1.48 (18H, s), 1.39 (3H, s), 1.25 (8H, broad s), 0.88 (3H, t, J = 6.5 Hz). (v) Salt of the trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-octanoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (E27) dissolved 50 mg (0.075 mmol) of the compound (E26) in 3 ml (50 times the volume) of methylene chloride, at room temperature and subsequently. it added to the system 1 ml (10 times the volume) of trifluoroacetic acid, at room temperature, and then the mixture was stirred at room temperature for 22 hours. After confirming that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60.5 g, 2-propanol: water = 5: 1) to obtain 38 mg (88% yield) of the title compound (E27) as a yellow solid. pale. Rf value: 0.3 (2-propanol: water = 5: 1) NMR with 1H (270 MHz, CD3OD): d (ppm) 5.55 (H, broad), 4.40-4.10 (7H, m), 3.65 (H, d, J = 9.0 Hz), 2.36 (2H, t, J = 7.0 Hz), 2.00 (3H, s), 1.70-1.50 (2H, m), 1.30 (8H, broad s), 0.90 (3H, t, J = 7.0 Hz); FAB-MS (positive): 459 (M + H) +; [a] D24 = +19. 2 ° (c = 0.26, MeOH).

EXAMPLE 6 Salt of trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-o-decanoyl-d-qicero-d-qalacto-non-2-enopyranosoic acid (E32) (compound copy No. 39) (i) 5-Acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-O-isopropyl-iden-7-0-decanoyl-D-glycero-D-qalacto-non-2-enopiranosoate of methyl (E28) 214 mg (0.58 mmol) of the compound (E3) was dissolved in 6.0 ml of methylene chloride, at room temperature, and subsequently 152 μl (0.87 mmol) of decanoyl chloride and 106 mg were added to the system. (0.87 mmol) of 4-dimethylaminopyridine, while cooling with ice, and then the mixture was stirred at room temperature for 30 minutes. Then 106 μml (0.87 mmol) of trimethylamine was poured into the reaction mixture at room temperature, and then the mixture was further stirred for 6 hours. After it was confirmed that the reaction was complete methanol was poured into the system, and then the mixture was stirred for 30 minutes. Then, ethyl acetate and an aqueous solution of sodium chloride were added to the reaction mixture to separate the mixture. The layer was dried organic medium thus obtained over magnesium sulfate and filtered and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, methylene chloride: methanol = 50: 1) to obtain 180 mg (63% yield) of the desired compound (E28) as a clear, colorless syrup. Rf value: 0.56 (methylene chloride: methanol = 20: 1); 1 H NMR (270 MHz, CDC13, TMS): d (ppm) 5.95 (ΔI, d, J = 2.7 Hz), 5.88 (ΔI, d, J = 7.9 Hz), 5.35 (ΔI, dd, J = 6.0, 1.8 Hz), 4.80 (HH, dd, J = 9.1, 2.7 Hz), 4.71 (HH, dd, J = 10.5, 1.8 Hz), 4.39 (HH, c, J = 6.0 Hz), 4.14 (HH, dd, J = 8.8, 6.0 Hz), 3.945 (HH, dd, J = 8.8, 6.0 Hz), 3.81 (3H, s), 3.45 (ÍH, ddd, J = 10.5, 9.1, 7.9 Hz), 2.41 (HH, t, J = 7.5 Hz), 2.39 (HH, t, J = 7.5 Hz), 2.02 (3H, s), 1.63 (2H, quintuple band, J = 7.5 Hz), 1.37 (3H , s), 1.35 (3H, s), 1.26 (8H, s), 0.88 (3H, t, J = 7.5 Hz); (ii) 5-acetamido-4-amino-2, 3,4,5-tetradeoxy-8, 9-O-isopropyl-iden-7-0-decanoyl-D-glycero-D-galacto-non-2-enopiranosoate of methyl (E29) 170 mg (0.32 mmol) of the compound (E28) was dissolved in ml of ethanol, at room temperature, and subsequently 60 mg (0.35 times the volume) of Lindlar's catalyst was added to the system at room temperature, after which the mixture was stirred at room temperature under hydrogen atmosphere , at a pressure of 1 atmosphere, for 1.5 hours. After confirming that the reaction the reaction mixture was filtered. The filtrate was washed with ethanol and the filtrate and washing solution were combined, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 15 g, ethyl acetate: 2-propanol: water = 5: 2: 1) to obtain 120 mg (yield 80%) of the title compound ( E29), as a white solid. Rf value: 0.40 (n-hexane.-ethyl acetate = 2: 1) NMR with 2H (270 MHz, CD3OD, TMS): d (ppm): 5.94 (H, d, J = 2.4 Hz), 5.42 (OH) , dd, J = 4.7, 1.8 Hz), 4.39 (ΔH, dt, J = 7.1, 6.0 Hz), 4.18 (HH, dd, J = 9.5, 1.6 Hz), 4.14 (HH, dd, J = 8.7, 6.4 Hz), 3.93 (HH, dd, J = 8.7, 6.4 Hz), 3.87 (HH, t, J = 9.5 Hz), 3.78 (3H, s), 3.44 (ÍH, dd, J = 9.5, 2.4 Hz), 2.35 (2H, c, J = 7.3 Hz), 1. 94 (3H, s), 1.60 (2H, quintuple band, J = 7.3 Hz), 1.32 (3H, s), 1.31 (3H, s), 1.27 (8H, s), 0.88 (3H, t, J = 7.3 Hz). (iii) 5-acetamido-4- (N, N'-bis-tert-butoxycarbonyl) quanidino-2,3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-decanoyl-D-qlicero -D-galacto-non-2-enopyranosoate methyl (E30) 100 mg (0.21 mmol) of the compound (E29) was dissolved, 87 mg (0.31 mmol) of N, N'-bis-tert-butoxycarbonyl thiourea and 87 μl (0.63 mmol) of triethylamine in 5 ml of dimethylformamide, at room temperature. Subsequently, 84 mg (0.31 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature for 2 hours. The mixture was diluted with ethyl acetate reaction and the mixture was filtered using Celite. The filtered product was washed with ethyl acetate. The filtrate thus obtained and the washing solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added thereto to separate it. The organic layer was dried over magnesium sulfate and filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel 60 gel, hexane: ethyl acetate = 2: 1) to obtain 120 mg (87% yield) of the title compound (E30), as a colorless clear syrup; Rf value: 0.30 (hexane-ethyl acetate = 2: 1) NMR with (270 MHz, CDCl 3, TMS): d (ppm) 11.4 (H, s), 8.46 (H, d, J = 8.7 Hz), 6.06 (HH, d, J = 8.7 Hz), 5.88 (HH, d, J = 2.4 Hz), 5.37 (HH, dd, J = 6.4, 1.5 Hz), 5.15 (HH, dt, J = 8.7, 2.4 Hz ), 4.38 (HH, c, J = 6.4 Hz), 4.28 (HH, dd, J = 8.7, 1.5 Hz), 4.23 (HH, t, J = 8.7 Hz), 4.10 (HH, dd, J = 9.6, 6.4 Hz), 3.95 (HH, dd, J = 9.6, 6.4 (Hz), 3.80 (3H, s), 2.453 (ÍH, dt, J = 16.0, 7.5 Hz), 2. 33 (ÍH, dt, J = 16.0, 7.5 Hz), 1.87 (3H, s), 1.61 (2H, quintuple band, J = 7.5 Hz), 1.49 (9H, s), 1.48 (9H, s), 1.38 ( 3H, s), 1.35 (3H, s), 1.25 (12H, broad s), 0.88 (3H, t, J = 7.5 Hz). (iv) 5-Acetamido-4- (N, N'-bis-tert-butoxycarbonyl) guanidino-2, 3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-decanoyl-D- acid glycero-D-qalacto-non-2-enopyranosoic (E31) 100 mg (0.14 mmol) of the compound (E30) was dissolved in a mixture of 4 ml (40 times the volume) of methanol and 1 ml (10 ml). times the volume) of water, and 6.5 mg (0.154 mmol) of lithium hydroxide monohydrate was added to the system at room temperature, and then the mixture was stirred at room temperature for 8 hours. After confirming that the reaction was complete, Dowex-50W was added to the system to neutralize the mixture. The reaction mixture was filtered and the filtered product was washed with methanol. The filtrate and wash solution were combined and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, ethyl acetate: 2-propanol: water = 10: 2: 1) to obtain 53 mg (yield 55%) of the desired compound (E31) as a solid white. Rf value: 0.38 (methylene chloride: methanol = 10: 1) NMR with (270 MHz, CDCl 3, TMS): d (ppm) 11.4 (OH, s), 8.48 (OH, d, J = 8.0 Hz), 6.31 (ÍH, s mate) 5.90 (ÍH, s broad), 5.30 (ÍH, s broad), 5.10 (ÍH, s broad), 4.60-3.30 (7H, m), 2.48 (ÍH, dt, J = 13.5, 6.5 Hz), 2.32 (ÍH, dt, J = 13.5, 6.5 Hz), 1.88 (3H, s), 1.60 (2H, quintuple band, J = 6.5 Hz), 1.48 (18H, s), 1.39 (3H, s) , 1.25 (12H, broad s), 0.88 (3H, t, J = 6 .5 Hz). (v) Salt of the trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-decanoyl-D-qicero-D-galacto-non-2-enopyranosoic acid (E32) dissolved 40 mg (0.057 mmol) of the compound (E31) in 3 ml (50 times the volume) of methylene chloride, at room temperature and subsequently was added to the system 1 ml (10 times the volume) of trifluoroacetic acid, at room temperature, and then the mixture was stirred at room temperature for 22 hours. After confirming that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60.5 g, 2-propanol: gua = 5: 1) to obtain 30 mg (87% yield) of the title compound (E32) as a yellow solid. pale. Rf value: 0.3 (2-propanol. -water = 5: 1) NMR with (270 MHz, CD3OD): d (ppm) 5.55 (H, broad), 4.40-4.10 (7H, m), 3.65 (H, d, J = 9.0 Hz), 2.36 (2H, t, J = 7.0 Hz), 2.00 (3H, s), 1.70-1.50 (2H, m), 1.30 (8H, broad s), 0.90 (3H, t, J = 7.0 Hz), -FAB-MS (positive): 487 (M + H) +; [a] D24 = + 17.2 ° (c = 0.15, MeOH).

EXAMPLE 7 Salt of trifluoroacetic acid of 5-acetamido-2,3,4-tetradeoxy-4-quanidino-9-o-palmitoyl-d-glycero-d-qalacto-non-2-enopyranosoic acid (E37) (compound copy No. 42) (i) 5-acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-0-isopropyl-iden-7-0-palmitoyl-D-glycero-D-qalacto-non-2-enopiranosoate of methyl (E33) 1.35 g (3.66 mmol) of the compound (E3) was dissolved in 10 ml of methylene chloride, at room temperature, and subsequently 1.88 ml (6.22 mmol) of palmitoyl chloride and 759 mg were added to the system. (4.33 mmol) of 4-dimethylaminopyridine, while cooling with ice, and then the mixture was stirred at room temperature for 30 minutes. Then 104 μl (6.21 mmol) of triethylamine was poured into the reaction mixture at room temperature, and then the mixture was further stirred for 15 hours. After it was confirmed that the reaction was complete methanol was poured into the system, and then the mixture was stirred for 30 minutes. Then, ethyl acetate and an aqueous solution of sodium chloride were added to the reaction mixture to separate the mixture. The layer was dried organic medium thus obtained over magnesium sulfate and filtered and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, n-hexane: ethyl acetate = 2: 1) to obtain 1.42 g (64% yield) of the desired compound (E33) as a colorless foam. Rf value: 0.53 (n-hexane: ethyl acetate = 1: 1); NMR with H (270 MHz, CDC13, TMS): d (ppm) 5.95 (H, d, J = 2.7 Hz), 5.88 (H, d, J = 7.9 Hz), 5.35 (H, d, J = 6.0, 1.8 Hz), 4.80 (HH, dd, J = 9.1, 2.7 Hz), 4.71 (HH, dd, J = 10.5, 1.8 Hz), 4.39(1H, c, J = 6.0 Hz), 4.14 (HH, dd, J = 8.8, 6.0 Hz), 3.945 (HH, dd, J = 8.8, 6.0 Hz), 3.81 (3H, s), 3.45 (ÍH, ddd, J = 10.5, 9.1, 7.9 Hz), 2.41 (1H, t, J = 7.5 Hz), 2.39 (ÍH, t, J = 7.5 Hz), 2.02 (3H, s), 1.63 (2H, quintuple band, J = 7.5 Hz), 1.37 (3H , s), 1.35 (3H, s), 1.26 (24H, s), 0.88 (3H, t, J = 7.5 Hz); (ii) 5-acetamido-4-amino-2, 3,4,5-tetradeoxy-8, 9-O-isopropyl-iden-7-0-palmitoyl-D-glycero-D-qalacto-non-2-enopiranosoate of methyl (E34) 1.42 g (2.34 mmol) of the compound (E33) was dissolved in 15 ml of ethanol at room temperature, and subsequently 477 mg (0.34 times the volume) of Lindlar's catalyst was added to the system to the room temperature, after which the mixture was stirred at room temperature under a hydrogen atmosphere, under pressure of 1 atmosphere, for 2 hours. After confirming that the reaction the reaction mixture was filtered. The filtrate was washed with ethanol and the filtrate and washing solution were combined, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 15 g, ethyl acetate: methanol = 10: 1) to obtain 1.16 g (85% yield) of the title compound (E34), as a foam colorless Rf value: 0.18 (ethyl acetate: methanol = 5: 1) NMR with ^ -H (270 MHz, CD3OD, TMS): d (ppm): 5.94 (H, d, J = 2.4 Hz), 5.42 (H, dd, J = 4.7, 1.8 Hz), 4.39 (1H, dt, J = 7.1, 6.0 Hz), 4.18 (HH, dd, J = 9.5, 1.6 Hz), 4.14 (HH, dd, J = 8.7, 6.4 Hz), 3.93 (HH, dd, J = 8.7, 6.4 Hz), 3.87 (HH, t, J = 9.5 Hz), 3.78 (3H, s), 3.44 (ÍH, dd, J = 9.5, 2.4 Hz), 2.35 (2H, c, J = 7.3 Hz), 1. 94 (3H, s), 1.60 (2H, quintuple band, J = 7.3 Hz), 1.32 (3H, s), 1.31 (3H, s), 1.27 (24H, s), 0.88 (3H, t, J = 7.3 Hz). (iii) 5-acetamido-4- (N, N * -bis-tert-butoxycarbonyl) quanidino- 2,3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-palmitoyl-D-glycero -D-qalacto-non-2-enopyranosoate methyl (E35) 1.16 g (2.0 mmoles) of the compound (E34) was dissolved, 828 mg (2.99 mmol) of N, N'-bis-tert-butoxycarbonyl thiourea and 0.42 ml (3.03 mmol) of triethylamine in 12 ml of dimethylformamide, at room temperature. Subsequently, 813 mg (2.99 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature for 2 hours. It was diluted with acetate the reaction mixture and the mixture was filtered using Celite. The filtered product was washed with ethyl acetate. The filtrate thus obtained and the washing solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added thereto to separate it. The organic layer was dried over magnesium sulfate and filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel gel 60, 15 g, hexane: ethyl acetate = 2: 1) to obtain 1.0 g (61% yield) of the title compound (E35), as a foam colorless Rf value: 0.52 (hexane: ethyl acetate = 2: 1) NMR with XH (270 MHz, CDC13, TMS): d (ppm) 11.4 (H, s), 8.46 (HH, d, J = 8.7 Hz), 6.06 (HH, d, J = 8.7 Hz), 5.88 (HH, d, J = 2.4 Hz), 5.37 (HH, dd, J = 6.4, 1.5 Hz), 5.15 (HH, dt, J = 8.7, 2.4 Hz), 4.38 (HH, c, J = 6.4 Hz), 4.28 (HH, dd, J = 8.7, 1.5 Hz), 4.23 (HH, t, J = 8.7 Hz), 4.10 (HH, dd, J = 9.6, 6.4 Hz), 3.95 (HH, dd, J = 9.6, 6.4 (Hz), 3.80 (3H, s), 2.453 (ÍH, dt, J = 16.0, 7.5 Hz), 2. 33 (ÍH, dt, J = 16.0, 7.5 Hz), 1.87 (3H, s), 1.61 (2H, quintuple band, J = 7.5 Hz), 1.49 (9H, s), 1.48 (9H, s), 1.38 ( 3H, s), 1.35 (3H, s), 1.25 (24H, broad s), 0.88 (3H, t, J = 7.5 Hz). (iv) 5-Acetamido-4- (N, N'-bis-tert-butoxycarbonyl) quanidino-2, 3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-palmitoyl-D- acid glycero-D-galacto-non-2-enopyranosoic (E36) 61 mg (0.07 mmol) of the compound (E35) was dissolved in a mixture of 1.2 ml (40 times the volume) of methanol and 0.15 ml (10 times the volume) of water, and 3.4 mg (0.08 mmol) of lithium hydroxide monohydrate was added to the system, at room temperature, and then the mixture was stirred at room temperature for 3 hours. After confirming that the reaction was complete, Dowex-50W was added to the system to neutralize the mixture. The reaction mixture was filtered and the filtered product was washed with methanol. The filtrate and wash solution were combined and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, ethyl acetate: methanol = 10: 1) to obtain 33 mg (55% yield) of the desired compound (E36) as a colorless foam. Rf value: 0.61 (ethyl acetate: methanol = 5: 1) NMR with (270 MHz, CDC13, TMS): d (ppm) 11.4 (H, s), 8.48 (H, d, J = 8.0 Hz), 6.31 (ÍH, s mate) 5.90 (ÍH, s broad), 5.30 (ÍH, s broad), 5.10 (ÍH, s broad), 4.60-3.30 (7H, m), 2.48 (1H, dt, J = 13.5, 6.5 Hz), 2.32 (ÍH, dt, J = 13.5, 6.5 Hz), 1.88 (3H, s), 1.60 (2H, quintuple band, J = 6.5 Hz), 1.48 (18H, s), 1.39 (3H, s) , 1.25 (8H, broad s), 0.88 (3H, t, J = 6.5 Hz). (v) Salt of the trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-palmitoyl-D-qlicero-D-qalacto-non-2-enopyranosoic acid (E37) dissolved 289 mg (0.36 mmol) of compound (E36) in 3 ml (50 times the volume) of methylene chloride, at room temperature and subsequently added to system 1 ml (10 times the volume) of trifluoroacetic acid, at room temperature, and then the mixture was stirred at room temperature for 22 hours. After confirming that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60.5 g, ethyl acetate: 2-propanol: water = 5: 2: 1) to obtain 206 mg (yield 84%) of the title compound ( E37) as a colorless foam. Rf value: 0.44 (2-propanol: water = 5: 1) NMR with (270 MHz, CD30D): d (ppm) 5.55 (H, broad), 4.40-4.10 (7H, m), 3.65 (H, d) , J = 9.0 Hz), 2.36 (2H, t, J = 7.0 Hz), 2.00 (3H, s), 1.70-1.50 (2H, m), 1.30 (24H, broad s), 0.90 (3H, t, J = 7.0 Hz); FAB-MS (positive): 571 (M + H) +; [a] D24 = +18. 5 ° (c = 0.12, MeOH).

EXAMPLE 8 Salt of trifluoroacetic acid of 5-acetamido-2,3,4-tetradeoxy-4-quanidino-9-o-dodecanoyl-d-qlycero-d-qalacto-non-2-enopyranosoic acid (E42) (compound copy No. 40) (i) 5-Acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-O-isopropyl-iden-7-0-dodecanoyl-D-glycero-D-qalacto-non-2-enopiranosoate of methyl (E38) 1.70 g (2.89 mmol) of the compound (E3) was dissolved in 11 ml of methylene chloride, at room temperature, and subsequently 1.03 ml (4.33 mmol) of dodecanoyl chloride and 529 mg were added to the system. (4.33 mmol) of 4-dimethylaminopyridine, while cooling with ice, and then the mixture was stirred at room temperature for 30 minutes. Then 0.6 ml (4.33 mmoles) of triethylamine was poured into the reaction mixture at room temperature, and then the mixture was further stirred for 2.5 hours. After it was confirmed that the reaction was complete methanol was poured into the system, and then the mixture was stirred for 30 minutes. Then, ethyl acetate and an aqueous solution of sodium chloride were added to the reaction mixture to separate the mixture. The layer was dried organic medium thus obtained over magnesium sulfate and filtered and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, n-hexane: ethyl acetate = 2-1) to obtain 1.07 g (67% yield) of the desired compound (E38) as a colorless foam. Rf value: 0.44 (n-hexane: ethyl acetate = 1: 1); 1 H NMR (270 MHz, CDCl 3, TMS): d (ppm) 5.95 (ΔI, d, J = 2.7 Hz), 5.88 (ΔI, d, J = 7.9 Hz), 5.35 (1H, dd, J = 6.0, 1.8 Hz), 4.80 (1H, dd, J = 9.1, 2.7 Hz), 4.71 (1H, dd, J = 10.5, 1.8 Hz), 4.39 (1H, c, J = 6.0 Hz), 4.14 (HH, dd, J = 8.8, 6.0 Hz), 3.945 (HH, dd, J = 8.8, 6.0 Hz), 3.81 (3H, s), 3.45 (ÍH, ddd, J = 10.5, 9.1, 7.9 Hz), 2.41 (HH, t, J = 7.5 Hz), 2.39 (HH, t, J = 7.5 Hz), 2.02 (3H, s), 1.63 (2H, quintuple band, J = 7.5 Hz), 1.37 (3H , s), 1.35 (3H, s), 1.26 (16H, s), 0.88 (3H, t, J = 7.5 Hz); (ii) 5-acetamido-4-amino-2, 3,4, 5-tetradeoxy-8, 9-O-isopropyl-iden-7-0-dodecanoyl-D-qlicero-D-qalacto-non-2-enopiranosoate of methyl (E39) 1.06 g (1.92 mmol) of the compound (E38) was dissolved in 10 ml of ethanol, at room temperature, and subsequently 353 mg (0.33 times the volume) of Lindlar catalyst was added to the system, to the ambient temperature, after which the mixture was stirred at room temperature under a hydrogen atmosphere, at a pressure of 1 atmosphere, for 1.5 hours. After confirming that the reaction the reaction mixture was filtered. The filtrate was washed with ethanol and the filtrate and washing solution were combined, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 15 g, ethyl acetate: methanol = 5: 1) to obtain 871 mg (86% yield) of the title compound (E39), as a foam colorless Rf value: 0.36 (ethyl acetate: methanol = 5: 1) NMR with K (270 MHz, CD30D, TMS): d (ppm): 5.94 (ΔH, d, J = 2.4 Hz), 5.42 (ΔI, dd, J = 4.7, 1.8 Hz), 4.39 (ÍH, dt, J = 7.1, 6.0 Hz), 4.18 (1H, dd, J = 9.5, 1.6 Hz), 4.14 (ÍH, dd, J = 8.7, 6.4 Hz), 3.93 (1H, dd, J = 8.7, 6.4 Hz), 3.87 (ÍH, t, J = 9.5 Hz), 3.78 (3H, s), 3.44 (1H, dd, J = 9.5, 2.4 Hz), 2.35 (2H, c, J = 7.3 Hz), 1. 94 (3H, s), 1.60 (2H, quintuple band, J = 7.3 Hz), 1.32 (3H, s), 1.31 (3H, s), 1.27 (16H, s), 0.88 (3H, t, J = 7.3 Hz). (iii) 5-Acetamido-4- (N, N'-bis-tert-butoxycarbonyl) guanidino-2,3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-dodecanoyl-D-glycero -D-galacto-non-2-enopyranosoate methyl (E40) 868 mg (1.65 mmoles) of the compound (E39) was dissolved, 940 mg (3.4 mmol) of N, N'-bis-tert-butoxycarbonyl thiourea and 0.95 ml (6.90 mmol) of triethylamine in 10 ml of dimethylformamide at room temperature. Subsequently 926 mg (3.4 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature for 2 hours. It was diluted with acetate the reaction mixture and the mixture was filtered using Celite. The filtered product was washed with ethyl acetate. The filtrate thus obtained and the washing solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added thereto to separate it. The organic layer was dried over magnesium sulfate and filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel gel 60, 15 g, hexane: ethyl acetate = 2: 1) to obtain 1.3 g (100% yield) of the title compound (E40), as a foam colorless Rf value: 0.47 (hexane: ethyl acetate = 2: 1) NMR with ^ -H (270 MHz, CDCl 3, TMS): d (ppm) 11.4 (1H, s), 8.46 (HH, d, J = 8.7 Hz), 6.06 (HH, d, J = 8.7 Hz), 5.88 (HH, d, J = 2.4 Hz), 5.37 (HH, dd, J = 6.4, 1.5 Hz), 5.15 (HH, dt, J = 8.7, 2.4 Hz), 4.38 (HH, c, J = 6.4 Hz), 4.28 (HH, dd, J = 8.7, 1.5 Hz), 4.23 (HH, t, J = 8.7 Hz), 4.10 (1H, dd, J = 9.6, 6.4 Hz), 3.95 (HH, dd, J = 9.6, 6.4 (Hz), 3.80 ( 3H, s), 2.453 (ΔI, dt, J = 16.0, 7.5 Hz), 2.33 (ΔI, dt, J = 16.0, 7.5 Hz), 1.87 (3H, s), 1.61 (2H, quintuple band, J = 7.5 Hz), 1.49 (9H, s), 1.48 (9H, s), 1.38 (3H, s), 1.35 (3H, s), 1.25 (16H, broad s), 0.88 (3H, t, J = 7.5 Hz) . (iv) 5-Acetamido-4- (N, N * -bis-tert-butoxycarbonyl) guanidino-2, 3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-d? decanoyl- acid D-qlyco-D-qalacto-non-2-enopyranosoic acid (E41) 100 mg (0.15 mmol) of the compound (E40) was dissolved in a mixture of 4 ml (40 times the volume) of methanol and 1 ml (10 ml). times the volume) of water, and 7.0 mg (0.165 mmol) of lithium hydroxide monohydrate was added to the system at room temperature, and then the mixture was stirred at room temperature for 8 hours. After confirming that the reaction was complete, Dowex-5OW was added to the system to neutralize the mixture. The reaction mixture was filtered and the filtered product was washed with methanol. The filtrate and wash solution were combined and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, ethyl acetate: 2-propanol: water = 10: 2: 1) to obtain 56 mg (56% yield) of the desired compound (E41) as a solid white. Rf value: 0.35 (methylene chloride: methanol = 10: 1); 1 H NMR (270 MHz, CDC13, TMS): d (ppm) 11.4 (HH, s), 8.48 (1H, d, J = 8.0 Hz), 6.31 (HH, s mate) 5.90 (H, broad), 5.30 (ÍH, broad), 5.10 (ÍH, broad), 4.60-3.30 (7H, m), 2.48 (ÍH, dt, J = 13.5, 6.5 Hz), 2.32 (ÍH, dt, J = 13.5, 6.5 Hz), 1.88 (3H, s), 1.60 (2H, quintuple band, J = 6.5 Hz), 1.48 (18H, s), 1.39 (3H, s), 1.25 (8H, broad s), 0.88 (3H, t , J = 6.5 Hz). (v) Salt of the trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-0-dodecanoyl-D-glycero-D-qalacto-non-2-enopyranosoic acid (E42) dissolved 50 mg (0.075 mmol) of compound (E41) in 3 ml (50 times the volume) of methylene chloride, at room temperature and subsequently added to system 1 ml (10 times the volume) of trifluoroacetic acid, at room temperature, and then the mixture was stirred at room temperature for 22 hours. After confirming that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60.5 g, 2-propanol: water = 5: 1) to obtain 38 mg (88% yield) of the title compound (E42) as a yellow solid. pale. Rf value: 0.3 (2-propanol: water = 5: 1) NMR with ^ -H (270 MHz, CD3OD): d (ppm) 5.55 (H, broad), 4.40-4.10 (7H, m), 3.65 ( ÍH, d, J = 9.0 Hz), 2.36 (2H, t, J = 7.0 Hz), 2.00 (3H, s), 1.70-1.50 (2H, m), 1.30 (8H, broad s), 0.90 (3H, t, J = 7.0 Hz); FAB-MS (positive): 515 (M + H) +; [c-ÜD24 - + 20.5 ° (c = 0.08, MeOH).

EXAMPLE 9 Salt of trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-o-octadecanoyl-d-qlycero-d-qalacto-non-2-enopyranosoic acid (E47) (compound copy No. 43) (i) 5-acetamido-4-azido-2, 3,4, 5-tetradeoxy-8, 9-O-isopropyl-iden-7-0-octadecanoyl-D-qlicero-D-qalacto-non-2-enopiranosoate of methyl (E43) 1.10 g (2.98 mmol) of the compound (E3) was dissolved in 11 ml of methylene chloride, at room temperature, and subsequently 1.70 ml (5.03 mmol) of stearoyl chloride and 620 mg were added to the system. (5.07 mmol) of 4-dimethylaminopyridine, while cooling with ice, and then the mixture was stirred at room temperature for 30 minutes. Then 0.70 ml (5.05 mmoles) of triethylamine was poured into the reaction mixture at room temperature, and then the mixture was further stirred for 15 hours. After it was confirmed that the reaction was complete methanol was poured into the system, and then the mixture was stirred for 30 minutes. Then, ethyl acetate and an aqueous solution of sodium chloride were added to the reaction mixture to separate the mixture. The layer was dried organic medium thus obtained over magnesium sulfate and filtered and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, n-hexane: ethyl acetate = 2: 1) to obtain 1.21 g (64% yield) of the desired compound (E43) as a colorless foam. Rf value: 0.51 (n-hexane: ethyl acetate = 1: 1); NMR with (270 MHz, CDC13, TMS): d (ppm) 5.95 (ΔI, d, J = 2.7 Hz), 5.88 (ΔI, d, J = 7.9 Hz), 5.35 (ΔI, dd, J = 6.0, 1.8 Hz), 4.80 (HH, dd, J = 9.1, 2.7 Hz), 4.71 (HH, dd, J = 10.5, 1.8 Hz), 4.39 (HH, c, J = 6.0 Hz), 4.14 (HH, dd, J = 8.8, 6.0 Hz), 3.945 (1H, dd, J = 8.8, 6.0 Hz), 3.81 (3H, s), 3.45 (ÍH, ddd, J = 10.5, 9.1, 7.9 Hz), 2.41 (ÍH, t, J = 7.5 Hz), 2.39 (1H, t, J = 7.5 Hz), 2.02 (3H, s), 1.63 (2H, quintuple band, J = 7.5 Hz), 1.37 (3H , s), 1.35 (3H, s), 1.26 (28H, s), 0.88 (3H, t, J = 7.5 Hz); (ü) 5-Acetamido-4-amino-2, -3, 4, 5-tetradeoxy-8,9-0-isopropyl-iden-7--0-octadecanoyl '-D-qlicero -D - Methyl qalacto-non-2 -enopyranosoate (E44) 1.20 g (1.88 mmoles) of the compound (E43) was dissolved in 12 ml of ethanol, at room temperature, and subsequently 399 mg (0.33 g) was added to the system. times the volume) of Lindlar catalyst, at room temperature, after which the mixture was stirred at room temperature under a hydrogen atmosphere, at a pressure of 1 atmosphere, for 3 hours. After confirming that the reaction the reaction mixture was filtered. The filtered product was washed with ethanol and the filtrate and washing solution were combined, then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60, 15 g, ethyl acetate, raetanol = 10: 1) to obtain 924 mg (80% yield) of the title compound (E44), as a foam colorless Rf value: 0.37 (ethyl acetate: methanol = 4: 1) NMR with R (270 MHz, CD3OD, TMS): d (ppm): 5.94 (ΔI, d, J = 2.4 Hz), 5.42 (ΔI, dd, J = 4.7, 1.8 Hz), 4.39 (ÍH, dt, J = 7.1, 6.0 Hz), 4.18 (HH, dd, J = 9.5, 1.6 Hz), 4.14 (HH, dd, J = 8.7, 6.4 Hz), 3.93 (HH, dd, J = 8.7, 6.4 Hz), 3.87 (HH, t, J = 9.5 Hz), 3.78 (3H, s), 3.44 (ÍH, dd, J = 9.5, 2.4 Hz), 2.35 (2H, c, J = 7.3 Hz), 1. 94 (3H, s), 1.60 (2H, quintuple band, J = 7.3 Hz), 1.32 (3H, s), 1.31 (3H, s), 1.27 (28H, s), 0.88 (3H, t, J = 7.3 Hz). (iii) 5-acetamido-4- (N, N * -bis-tert-butoxycarbonyl) quanidino-2,3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-octadecanoyl-D-qlicero -D-qalacto-non-2-enopyranosoate methyl (E45) 916 mg (1.50 mmoles) of the compound (E44) was dissolved, 539 mg (1.95 mmol) of N, N'-bis-tert-butoxycarbonyl thiourea and 0.27. ml (1.95 mmol) of triethylamine in 12 ml of dimethylformamide, at room temperature. Subsequently, 529 mg (1.95 mmol) of mercuric chloride was added to the system while cooling with ice, and then the mixture was stirred at room temperature for 4 hours. It was diluted with acetate the reaction mixture and the mixture was filtered using Celite. The filtered product was washed with ethyl acetate. The filtrate thus obtained and the washing solution were combined and ethyl acetate and a saturated aqueous solution of sodium chloride were added thereto to separate it. The organic layer was dried over magnesium sulfate and filtered, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Kiesel gel 60, 15 g, hexane: ethyl acetate = 2: 1) to obtain 750 mg (yield 59%) of the title compound (E45), as a foam colorless Rf value: 0.29 (hexane: ethyl acetate = 2: 1) NMR with E (270 MHz, CDC13, TMS): d (ppm) 11.4 (1H, s), 8.46 (1H, d, J = 8.7 Hz), 6.06 (IH, d, J = 8.7 Hz), 5.88 (IH, d, J = 2.4 Hz), 5.37 (HH, dd, J = 6.4, 1.5 Hz), 5.15 (HH, dt, J = 8.7, 2.4 Hz), 4.38 (HH, c, J = 6.4 Hz), 4.28 (HH, dd, J = 8.7, 1.5 Hz), 4.23 (HH, t, J = 8.7 Hz), 4.10 (HH, dd, J = 9.6, 6.4 Hz), 3.95 (HH, dd, J = 9.6, 6.4 (Hz), 3.80 (3H, s), 2.453 (ÍH, dt, J = 16.0, 7.5 Hz), 2. 33 (ÍH, dt, J = 16.0, 7.5 Hz), 1.87 (3H, s), 1.61 (2H, quintuple band, J = 7.5 Hz), 1.49 (9H, s), 1.48 (9H, s), 1.38 ( 3H, s), 1.35 (3H, s), 1.25 (28H, broad s), 0.88 (3H, t, J = 7.5 Hz). (iv) 5-Acetamido-4- (N, N'-bis-tert-butoxycarbonyl) guanidino-2, 3,4,5-tetradeoxy-8, 9-0-isopropylidene-7-0-octa-decanoyl- D-glycero-D-galacto-non-2-enopyranosoic (E46) 741 mg (0.87 mmol) of the compound (E45) was dissolved in a mixture of 15 ml of methanol and 1.5 ml of water, and was added to the 38 mg system (0.91 mmol) of lithium hydroxide monohydrate, at room temperature, and then the mixture was stirred at room temperature for 6 hours. After confirming that the reaction was complete, a solution of 4N HCl in dioxane was added to the system to neutralize the mixture and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel 60 gel, ethyl acetate: methanol = 10: 1) to obtain 430 mg (yield 59%) of the desired compound (E16) as a colorless foam. Rf value: 0.40 (methylene chloride: methanol = 5: 1); 1 H NMR (270 MHz, CDC13, TMS): d (ppm) 11.4 (HH, s), 8.48 (HH, d, J = 8.0 Hz), 6.31 (HH, s mate) 5.90 (HH, broad), 5.30 (ÍH, broad), 5.10 (ÍH, broad), 4.60-3.30 (7H, m), 2.48 (ÍH, dt, J = 13.5, 6.5 Hz), 2.32 (ÍH, dt, J = 13.5, 6.5 Hz), 1.88 (3H, s), 1.60 (2H, quintuple band, J = 6.5 Hz), 1.48 (24H, s), 1.39 (3H, s), 1.25 (28H, broad s), 0.88 (3H, t , J = 6.5 Hz). (v) Salt of the trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-9-0-octadecanoyl-D-glycero-D-galacto-non-2-enopyranosoic acid (E47) dissolved 422 mg (0.50 mmol) of the compound (E46) in 3 ml of methylene chloride, at room temperature and subsequently 1 ml of trifluoroacetic acid was added to the system, at room temperature, and then the mixture was stirred at room temperature for 22 hours.

After confirming that the reaction was complete, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (Kiesel gel 60.5 g, ethyl acetate: 2-propanol: water = 5: 2: 1) to obtain 300 mg (yield 84%) of the title compound ( E47) as a colorless foam. Rf value: 0.44 (2-propanol. -water = 5: 1) 1 H NMR (270 MHz, CD3OD): d (ppm) 5.55 (H, broad), 4.40-4.10 (7H, m), 3.65 (H) , d, J = 9.0 Hz), 2.36 (2H, t, J = 7.0 Hz), 2.00 (3H, s), 1.70-1.50 (2H, m), 1.30 (28H, broad s), 0.90 (3H, t, J = 7.0 Hz); FAB-MS (positive): 599 (M + H) +; [Q;] D24 = +19. 8 ° (c = 0.15, MeOH). EXAMPLE 10 Trifluoroacetic acid salt of 5-acetamido-2,3,4-tetradeoxy-4-quanidino-d-glycero-d-qalacto-non-2-enopyranosoate cetyl (E48) (exemplary composition No. 89) The procedures were carried out in a manner similar to those of Example 1, using cetyl alcohol instead of myristyl alcohol, to obtain the title compound. NMR with H (270 MHz, CD3OD): d (ppm): 5.83 (ΔI, d, J = 2.7 Hz),4. 44 (HH, dd, J = 9.0, 2.7 Hz), 4.38 (HH, dd, J = 9.0, < 1H), 4.18 (2H, t, J = 6.2 Hz), 4.17 (HH, t, J = 9.0 Hz), 3.90-3.74 (2H, m), 3. 68 (1H, dd, J = 12.0, 4.5 Hz), 3.65 (1H, d, J = 9.0 Hz), 1.99 (3H, s), 1.67 (2H, quintuple band, J = 6.2 Hz), 1.26 (28H, s broad), 0.87 (3H, t, J = 6.2 Hz).

EXAMPLE 11 Salt of trifluoroacetic acid of 5-acetamido-2,3,4,5-tetradeoxy-4-quanidino-d-qicero-d-qalacto-non-2- stearyl enopyranosoate (E49) (exemplary compound No. 91) The procedures were carried out in a manner similar to those of Example 1, using stearyl alcohol instead of myristyl alcohol, to obtain the title compound. 1 H NMR (270 MHz, CD3OD): d (ppm): 5.83 (ΔI, d, J = 2.7 Hz), 4.44 (ΔI, dd, J = 9.0, 2.7 Hz), 4.38 (ΔI, dd, J = 9.0, < 1H), 4.18 (2H, t, J = 6.2 Hz), 4.17 (H, t, J = 9.0 Hz), 3.90-3.74 (2H, m), 3.68 (1H, dd, J = 12.0, 4.5 Hz), 3.65 (ÍH, d, J = 9.0 Hz), 1.99 (3H, s), 1.67 (2H, quintuple band, J = 6.2 Hz), 1.26 (32H, broad s), 0.87 (3H, t, J = 6.2 Hz).

EXAMPLE OF PREPARATION 1 An aqueous solution was prepared in such a way that the compound of example 4 was present in 10% (w / w), banzalkonium chloride in 0.04% (w / w), phenylethyl alcohol in 0.40% (w / w / weight) and purified water in 89.56% (weight / weight).

EXAMPLE OF PREPARATION 2 A cosolvent aqueous solution was prepared, so that the compound of example 4 was present in 10% (w / w), banzalkonium chloride in 0.04% (w / w), polyethylene glycol 400 in 10.0% (w / w / weight), propylene glycol in 30% (in weight / weight) and purified water in 39.96% (in weight / weight).

EXAMPLE OF PREPARATION 3 A dry powder was prepared so that the compound of Example 4 was present in 40% (w / w) and lactose in 60% (w / w).

EXAMPLE OF PREPARATION 4 An aerosol agent was prepared in such a way that it contained 10% (w / w) of the compound of Example 4, 0.5% (in weight / weight) of lecithin, 34.5% Freon 11 and 55% Freon 12.

EXAMPLE OF TEST 1 Inhibitory activity of sialidase in the influenza virus A cannula was inserted into the trachea of BALB / C female mice, 5 to 6 weeks of age, with body weight of 20 g, under anesthesia, after which 0.5 ml of phosphate-regulated physiological saline solution was injected. Pulmonary washes were then obtained by collecting the liquid by aspiration, and repeating the procedure three times. 1 μmol of the test compound (sample), 10 μg of lung washings were mixed in terms of the amount of protein, and phosphate-regulated physiological saline and incubated at 37 ° C for 1 to 3 days, at a final volume of 100 μl. After sampling 10 μl of this reaction mixture, the sialidase reaction was carried out in 32.5 μmol of 2- (N-morpholino) ethanesulfonate buffer (pH 6.5) containing 40 mmoles of calcium chloride, using the influenza virus A / PR / 8/34 (equivalent to 5 x 10 plaque-forming units) such as the enzyme sialidase and 0.1 mmol of 4-methylumberiferyl-N-acetyl-a; -D-neuraminate ammonium, as a substrate. The fluorescence intensity of the 4-methylumbelliferone produced in the reaction mixture was measured at an excitation wavelength of 360 nm and a measurement length of 460 nm. On the other hand, prepared a concentration versus inhibition curve by performing similar reactions by using various concentrations of compound A (GG-167) as a sample. The amount of substance having sialidase inhibitory activity, formed in the lung washes, was determined quantitatively from the test compound, as the amount of compound A, using the above inhibition curve. While the compound of the present invention did not directly exhibit sialidase inhibitory activity in the influenza virus, when treated with biological fractions containing hydrolase (e.g., mouse lung washes), the compound of the present invention exhibited sialidase inhibitory activity. in the influenza virus, similar to that of compound A.

EXAMPLE OF TEST 2 Experiment 1 of treatment of infection in mice A solution containing 500 pfu (plaque forming units) of strain A / PR / 8/34 of influenza virus acclimated in mice was prepared in 50 μl of phosphate buffer containing 0.42% bovine serum albumin, which was then used to infect mice (BALB / C females, 5 to 6 weeks of age, 20 g), dripping into the nose for infection. The compounds of the present invention were prepared at a dose level of 0.6 μmol / kg / 50 μl, suspending in saline physiological and administering to the animals by drip in the nose, in a total of 3 occasions to 4 hours before, 4 hours later and 17 hours after the viral infection. The test was carried out in groups of 7 or 8 animals and the results indicated as number of surviving mice, divided by the number of test mice at 6, 8 and 10 days after infection. Incidentally, compound A (GG-167) was used as the comparative compound.

TABLE 2 Day 6 Day 8 Day 10 Physiological salt only 1/7 0/7 0/7 Compound A 7/7 3/7 0/7 Compound example 1 8/8 5/8 3/8 Compound example 2 8/8 2/8 1/8 Although all the animals of the group that received doses of compound A died on the 10th day after infection, three or one of the animals of the groups that received doses of the compounds of example 1 or of example 2 were still alive. These were found to indicate that the compound of example 1 or example 2 of the present infection has therapeutic effects against influenza infection superior to those of compound A.

EXAMPLE OF TEST 3 Experiment 2 of treatment of infection in mice A solution containing 500 pfu (plaque forming units) of strain A / PR / 8/34 of influenza virus acclimated in mice was prepared in 50 μl of phosphate buffer containing 0.42% bovine serum albumin, which was He then used to infect mice (BALB / C, females, 5 to 6 weeks of age, 20 g) dripping into the nose for infection. The compounds of the present invention were prepared at a dose level of 0.9 μmol / kg / 50 μl, suspending in physiological saline and administered to the animals by dripping into the nose, a total of three times to 4 hours before, 4 hours later and 17 hours after the viral infection. The test was carried out in groups of 4 to 12 animals, and the results were indicated as the number of surviving mice divided by the number of test mice at 8 and 10 days after infection. Incidentally, compound A (GG-167) was used as the comparative compound.

TABLE 3 Day 8 Day 10 Physiological salt only 0/4 0/4 Compound A 0/8 0/8 Compound example 1 4/12 2/12 Compound example 10 10/12 5/12 Compound example 11 11/11 5/11 Although all the animals that received doses of compound A died on the 10th day after infection, two of the 5 groups of animals that received doses with the compounds of example 1, example 10 or example 11 were still alive. This indicates that the compounds of example 1, example 10 or example 11 of the invention have therapeutic effects due to influenza infection higher than those of compound A.

EXAMPLE OF TEST 4 Experiment 3 of treatment of infection in mice A solution containing 500 pfu (plaque forming units) of strain A / PR / 8/34 of influenza virus acclimated in mouse was prepared in 50 μl of phosphate buffer containing 0.42% bovine serum albumin, and then it was used then to infect mice (BALB / C, females, 5 to 6 weeks of age, 20 g) dripping into the nose for infection. The compounds of the present invention were prepared at a dose level of 0.3 μmol / kg / 50 μl, suspended in physiological saline, and administered to the animals by drip in the nose, on a total of three occasions, at 4 hours before, 4 hours later and 17 hours after the viral infection. The test was carried out in groups of 10 or 11 animals and the results were indicated as the number of surviving mice divided by the number of test mice at 6 and 8 days after infection. Incidentally, compound A (GG-167) was used as a comparison compound.

TABLE 4 Day 6 Day 8 Physiological salt only 0/10 0/10 Compound A 10/10 1/10 Compound example 3 10/10 10/10 Compound example 4 10/10 6/10 Compound example 5 11/11 10/11 Example compound 6 11/11 10/11 Compound example 7 10/110 3/10 Compound example 8 11/11 2/11 Compound example 9 10/10 4/10 While only one of the animals that received doses of compound A survived on day 8 after infection, two to ten animals of the groups that received doses of the compounds of any of examples 3 to 9 were still alive. These results indicate that the compounds of examples 3 to 9 of the present invention have therapeutic effects against influenza infection superior to those of compound A.

INDUSTRIAL APPLICABILITY The neuraminic acid compound (1) of the present invention undergoes hydrolysis by the hydrolase present in the living body and exhibits excellent viral reproduction inhibiting activity and excellent sialidase inhibitory activity. In addition, if the neuraminic acid compound (1) is administered to mice infected with the influenza virus, the compound exhibits therapeutic effects of infection superior to that of compound A (GG-167) described in WO 91/16320 (Japanese patent application). of TCP (Kokai) No. Hei 5-507068. Thus, the neuraminic acid compound (1) of the present invention is useful as a therapeutic or preventive agent (preferably a therapeutic agent) for viral infections (preferably infections). viral infections)

Claims (31)

NOVELTY OF THE INVENTION CLAIMS

1. - A compound represented by the formula (1): or a pharmacologically acceptable salt thereof, characterized in that R-1 represents a ml group which may be substituted with a halogen atom; R 0, R 3 and R 4 may be the same or different and each represents a hydrogen atom or an aliphatic acyl group having from 3 to 25 carbon atoms; and W represents a hydrogen atom or an ester residue; subject to the fact that the compounds of the formula (1) in which each of R 0, R 3, R 4 and W is a hydrogen atom are excluded.

2. The compound or pharmacologically acceptable salt thereof according to claim 1, further characterized in that R is a ml group that can be substituted with a fluorine atom.

3. The compound or a pharmacologically acceptable salt thereof according to claim 1, further characterized in that R1 is a ml, monofluoroml or difluoroml group.

4. The compound or a pharmacologically acceptable salt thereof according to claim 1, further characterized in that R is a ml group.

5. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 4, further characterized in that R is a hydrogen atom or an aliphatic acyl group having from 6 to 25 carbon atoms.

6. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 4, further characterized in that R is a hydrogen atom or an aliphatic acyl group having from 6 to 20 carbon atoms.

7. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 4, further characterized in that R is a hydrogen atom or a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group.

8. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 7, further characterized in that R is a hydrogen atom or an aliphatic acyl group having from 6 to 25 carbon atoms.

9. The compound or its pharmacologically acceptable salt according to any of claims 1 to 7, further characterized in that R 3 is a hydrogen atom or an aliphatic acyl group having from 6 to 20 carbon atoms.

10. The compound or its pharmacologically acceptable salt according to any of the claims 1 to 7, characterized furthermore because RJ is a hydrogen atom or a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group.

11. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 10, further characterized in that R is a hydrogen atom or an aliphatic acyl group having 6 to 25 carbon atoms.

12. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 10, further characterized in that R is a hydrogen atom or an aliphatic acyl group having from 6 to 20 carbon atoms.

13. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 10, further characterized in that R4 is a hydrogen atom or a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group.

14. The compound or its pharmacologically acceptable salt according to any of claims 1 to 4, further characterized in that R is an aliphatic acyl group having from 3 to 25 carbon atoms and each of R and R is a carbon atom. hydrogen.

15. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 4, further characterized in that R is an aliphatic acyl group having from 6 to 25 carbon atoms and each of R and R is an atom of hydrogen.

16. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 4, further characterized in that R is an aliphatic acyl group having from 6 to 20 carbon atoms and each of R and R is a hydrogen atom.

17. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 4, further characterized in that R is a hexanoyl, octanoyl, decanoyl, dodecanoyl, myristoyl, palmitoyl or stearoyl group, and each of R and R is a hydrogen atom.

18. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 17, further characterized in that W is a hydrogen atom or an alkyl group having from 1 to 18 carbon atoms.

19. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 17, further characterized in that W is a hydrogen atom. 20.- The compound or a pharmacologically salt acceptable thereof according to any of claims 1 to 17, further characterized in that W is an ester residue. 21. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 17, further characterized in that W is an alkyl group having from 6 to 18 carbon atoms. 22. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 4, further characterized in that each of R 0, R 3 and R 4 - is a hydrogen atom and W is an ester residue. 23. The compound or a pharmacologically acceptable salt thereof according to any of claims 1 to 4, further characterized by each of p? R, R and R is a hydrogen atom and W is an alkyl group having from 6 to 18 carbon atoms. 24. The compound or a pharmacologically acceptable salt thereof according to claim 1, further characterized in that R is a methyl group that can be or be substituted with a fluorine atom; R is an aliphatic group having from 3 to 25 carbon atoms; each of R and R is a hydrogen atom and W is a hydrogen atom or an ester residue. 25. The compound or a pharmacologically acceptable salt thereof according to claim 1, further characterized in that R1 is a methyl group; R o is a aliphatic acyl group having from 6 to 25 carbon atoms; each of R and R is a hydrogen atom and W is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms. 26. The compound or a pharmacologically acceptable salt thereof according to claim 1, further characterized in that Ri is a methyl group; R o is an aliphatic acyl group having from 6 to 20 carbon atoms; each of R, R and W is a hydrogen atom. 27. The compound or a pharmacologically acceptable salt thereof, according to claim 1, further characterized in that R is a methyl group that can be substituted with a fluorine atom; each of R, R and R is a hydrogen atom and W is an ester residue. 28. The compound or a pharmacologically acceptable salt thereof, according to claim 1, further characterized in that R is a methyl group, each of R, R3 and R4 is a hydrogen atom and W is an alkyl group having from 6 to 18 carbon atoms. 29. The compound or a pharmacologically acceptable salt thereof according to claim 1, further characterized in that they are selected from the following group of compounds: 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9 acid -0-hexanoyl-D-glycero-D-galacto-non-2-enopyranosoic; 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-octanoyl-D-glycero-D-galacto-non-2- acid enopyranosoic; 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-decanoyl-D-glycero-D-galacto-non-2-enopyranosoic acid; 5-Acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-dodecanoyl-D-glycero-D-galacto-non-2-enopyranosoic acid; 5-acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-myristoyl-D-glycero-D-galacto-non-2-enopyranosoic acid; 5-Acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-palmitoyl-D-glycero-D-galacto-non-2-enopyranosoic acid; 5-Acetamido-2,3,4,5-tetradeoxy-4-guanidino-9-0-stearoyl-D-glycero-D-galacto-non-2-enopyranosoic acid; 5-Acetamido-2, 3,4, 5-tetradeoxy-4-guanidino-D-glycero-D-galacto-non-2-enopyranosoate hexyl; 5-acetamido-2, 3,4, 5-tetradeoxy-4-guanidino-D-glycero-D-galacto-non-2-enopyranosoate myristyl; 5-Acetamido-2,3,4,5-tetradeoxy-4-guanidino-D-glycero-D-galacto-non-2-enopyranosoate cetyl; 5-Acetamido-2,3,4,5-tetradeoxy-4-guanidino-D-glycero-D-galacto-non-2-enopyranosoate stearyl. 30. A pharmaceutical composition characterized in that it contains as an active ingredient the compound of the formula (1) or a pharmacologically acceptable salt thereof, as defined in any of claims 1 to 29. 31.- The use of the compound of Formula (1) or a pharmacologically acceptable salt thereof as defined in any of claims 1 to 29, for the manufacture of a drug for the treatment or prevention of viral infections.