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OA12372A - Phenoxybenzylamine derivatives as selective seotonin re-uptake inhibitors. - Google Patents

Phenoxybenzylamine derivatives as selective seotonin re-uptake inhibitors. Download PDF

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Publication number
OA12372A
OA12372A OA1200300056A OA1200300056A OA12372A OA 12372 A OA12372 A OA 12372A OA 1200300056 A OA1200300056 A OA 1200300056A OA 1200300056 A OA1200300056 A OA 1200300056A OA 12372 A OA12372 A OA 12372A
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methyl
mhz
compounds
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formula
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OA1200300056A
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Inventor
Mavis Diane Adam
Mark David Andrew
Mark Leonard Elliot
Geoffrey Edward Gymer
David Hepworth
Howard Harry Ralph Jr
Donald Stuart Moddleton
Alan Stobie
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Pfizer
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Priority claimed from GB0021593A external-priority patent/GB0021593D0/en
Priority claimed from GB0107116A external-priority patent/GB0107116D0/en
Application filed by Pfizer filed Critical Pfizer
Publication of OA12372A publication Critical patent/OA12372A/en

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
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    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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    • A61K31/39—Heterocyclic compounds having sulfur as a ring hetero atom having oxygen in the same ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P25/00—Drugs for disorders of the nervous system
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
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    • A—HUMAN NECESSITIES
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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    • C07D327/06—Six-membered rings
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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    • C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
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    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

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  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Hydrogenated Pyridines (AREA)
  • Quinoline Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Claims (1)

  1. 012372 97 Claims A compound of general formula (I), pharmaceutically acceptable salts, solvatésor polymorphs thereof; NR1R2
    10 15 20 wherein; R1 and R2, which may be the same or different, are H, Ci-C6alkyl or (CH2)d(C3-C6cycloalkyl) wherein d = 0, 1, 2 or 3; or R1and R2 togetherwiththe nitrogen to which they are attached form an azetidine ring; Z or Y is -SR3 and the other Z or Y is halogen or -R3; wherein R3 is independentlyC.,-C4 alkyi optionally substituted with fluorine; except that R3 is not CF3; or Z and Y are linked so that, togetherwith the interconnecting atoms, Z and Yform a fused 5 to 7-membered carbocyclic or heterocyclic ring which maybe saturated, unsaturated or aromatic, and wherein when Z and Y form aheterocyclic ring, in addition to carbon atoms, the iinkage contains one ortwo heteroatoms independently selected from oxygen, sulfur and nitrogen;with the proviso that when R5 is fluorine and R2 is methyl thsn the fusedring is not 1,3-dioxaiane and Z and Y together do not form a fused phenyiring; R4 and R5, which may be the same or different, are: A-X, wherein A = -CH=CH- or -(CH2)P- where p is 0, 1 or 2; X is hydrogen, F, Ci,Br, l, ÇONR6R7, SO2NR6R7, SO2NHC(=O)RE, OH, CMalkoxy, NR6SO2RS,NO2, NR6R11, CN, CO2R10, CHO, SR10, S(O)RS or SO2R10; R6, R7, R8 andR10 which may be the same or different, are hydrogen or C-j_ealkyioptionally substituted independently by one or more R12; Rs is Cv6 alkyioptionally substituted independently by one or more R12; R11 is hydrogen,0,.6 alkyi optionally substituted independently by one or more R12, C(O)R6,CO2R9, C(O)NHR6 or SO2NR6R7; R12 is F, OH, CO2H, C^cycioaikyi, NH2,CONHj, C^alkoxy, C^alkoxycarbonyi or a 5- or 6-membered heterocyclic 25 012372 98 ring containing 1, 2 or 3 heteroatoms selected from N, S and O optionallysubstituted independently by one or more R13; or R6 and R7, together withthe nitrogen to which they are attached, form a 4-, 5- or 6-memberedheterocyclic ring optionally substituted independently by one or more R13; 5 or 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selectedfrom N, S and O, optionally substituted independently by one or more R13; wherein R13 is hydroxy, C1-C4alkoxy, F, CrCgalkyl, haloalkyl, haloalkoxy, -NH2,-NH(CrCsalkyl) or -N(CrC6alkyl)2. 10 2 A compound according to claim 1, pharmaceutically acceptable salts, solvatés orpolymorphs thereof, wherein R1 and R2, which may be the same or different, are ihydrogen or CrC6alkyl. 15 3 A compound according to daims 1 or 2, pharmaceutically acceptable salts, solvatés or polymorphs thereof, wherein when Z or Y is -SR3, R3 is methyl orethyl. 4 A compound according to daims 1 or 2, pharmaceutically acceptable salis, 20 solvatés or polymorphs thereof, wherein when Z and Y are iinked to form a fused ring, the ring is a heterocyclic ring. 5 A compound according to daim 4, pharmaceutically acceptabie salts, solvatés orpolymorphs thereof, wherein in addition to carbon atoms, the linkage contains 25 one or two suifur atoms. 6 A compound according to any preceding daim, pharmaceutically acceptabiesalts, solvatés or polymorphs thereof, wherein R6 and R7, which may be the sameor different, are hydrogen, C^Csalkyl optionally substituted by hydroxy, -CONH2 30 or C1-C3alkoxy. 7 A compound according to any preceding claim, pharmaceutically acceptable salts, solvatés or polymorphs thereof, wherein R8 is hydrogen, hydroxyethyl ormethyl. 35 01237^ 99 8 A compound according to any preceding ciaim, pharmaceutically acceptablesalts, solvatés or polymorphs thereof, wherein R9 is methyl, ethyl, isopropyl,trifluoromethyl or methoxyethyl. 5 9 A compound according to any preceding daim, pharmaceutically acceptable salts, soivates or polymorphs thereof, wherein p is 1 or 0. 10 A compound according to any preceding daim, pharmaceutically acceptablesalts, soivates or polymorphs thereof, wherein R4 and R5, which may be the 10 same or different, are -(CH2)P-X, where p is û, 1 or 2; X is hydrogen, hydroxy, CONR6R7, SO2NR6R7,NR8SO2R9, SR10, SOR9 or SO2R10 wherein Re, R7, R8, R8 and R10 are asdefmed in daim 1, or 5- or 6-membered heterocyclic ring containing 1, 2 or 3 heteroatoms selected15 from N, S and O. 11 A compound according to any preceding daim, pharmaceutically acceptablesalts, soivates or polymorphs thereof, wherein R4 and R5, which may be thesame or different, are: 20 -(CH2)p-X, where p is 0 or 1; X is hydrogen, hydroxy, CONR6R7, SO2NR5R7 or NR8SO2R9; wherein R6 and R7, which may be the same or different, arehydrogen or CrC3alkyl optionaily substituted by hydroxy, -CONH2 or C·,-C3alkoxy (preferably methoxy); Ra is hydrogen, hydroxyethyl or methyl; orR9 is methyl, ethyl, isopropyl, trifluoromethyl or methoxyethyl; or 25 triazolyl, imidazolyl or pyrazoiyl. 12 A compound according to any preceding daim, pharmaceutically acceptable salts, soivates or polymorphs thereof, wherein R4 and R5 are not both hydrogen. 30 13 A compound according to any preceding daim, pharmaceutically acceptable t salts, soivates or polymorphs thereof, wherein R4 is hydrogen. 14 A compound according to cîaim 1, pharmaceutically acceptable salts, soivates orpolymorphs thereof, selected from the group: 012372 100 4-(2,3-dihydro-1-benzothien-5-yloxy)-3-[(methytamino)methyi]- benzenesuifonamide (Example 2); 3- [(dimetbylamino)methyl]-4-[3-methyl-4-(methyisulfanyl)phenoxy]-benzenesulfonamide (Example 12); 4- (2,3-dihydro-1-benzothien-5-yloxy)-3-[(dimethyiamino)methyl]-benzenesulfonamide (Example 16); 4-[3-chioro-4-(methylsulfanyl)phenoxy]-3-[(dimethylamino)methyl]-benzenesulfonamide (Example 17); 3-[(dimethylamino)methyl]-4-[3-fluoro-4-(tnethylsulfanyl)phenoxy]-benzenesuifonamide (Example 18); W,/V-dirnethyl-/V-[2-(6-quinoiinyloxy)benzyl]amine (Example 29); 3- [(methylamino)methyl]-4-(6-quinolinyloxy)benzenesulfonamide (Exampie 35); 4- (2,3-dihydro-1-benzothien-5-yioxy)-3-[(methyiamino)methylîbenzamide(Example 60); 4-(2,3-dihydro-1-benzothien-5-yioxy)-/\/-methyl-3-[(methylamino)methyi]-benzamide (Example 62); W-{3-[(methyiamino)methyl]-4-[3-methyl-4-(methylsuifanyl)phenoxy]benzyl}methanesuifonamide (Exampie 75); 3- [(methyiamino)methyi]-4-[3-methyi-4-(methylsu!fanyi)phenoxy3benzamide(Example 79); 4- (2,3-dihydro-1,4-benzoxathiin-7-yloxy)-3-[(dimethylamino)methyl]benzamide(Exampie 88); {3-[(dimethy!amino)methyl]-4-[3-fluoro-4-(methyisulfanyl)phenoxy]phenyl}-methanol (Example 90); 3-[(dimethyiamino)methyl]-4-(6-quinolinyioxy)benzamide (Example 100);3-[(methylamino)methyl}-4-(6-quinoiinyloxy)benzarnide (Example 102);W-methyl-W-{3-[(methylamino)methyl]-4-[3-methyl-4-(methylsulfany!)phenoxy]-phenyljmethanesulfonamide (Example 116) and A/-{4-(2,3-dihydro-1,4-benzoxathiin-7-yioxy)-3-[{dimethyiamino)methyi]phenyl}-methanesulfonamide (Exampie 124). 15 A compound as defined in any preceding claim, pharmaceuiically acceptable saits, soivates or polymorphe thereof, for use as a pharmaceuticai. 16 16 5 17 5 17 10 18 10 18 1915 20 012372 101 1915 20 A pharmaceutical formulation containing a compound as defined in any one ofdaims 1 to 14, or pharmaceuticatly acceptable salts, solvatés or polymorphsthereof, and a pharmaceutically acceptable adjuvant, diluent or carrier. The use of a compound as defined in any of daims 1 to 14, pharmaceuticallyacceptable salts, solvatés or polymorphs thereof, in the manufacture of amédicament for the treatment or prévention of a disorder in which the régulationof monoamine transporter fonction is implicated. The use according to claim 17 wherein the disorder is dépréssion, attentiondéficit hyperactivity disorder, obsessive-compulsive disorder, post-traumaticstress disorder, substance abuse disorders or sexual dysfonction. The use according to claim 18 wherein the disorder is prématuré éjaculation. Use of a compound as defined in any one of daims 1-14, pharmaceuticallyacceptable salts, solvatés or polymorphs thereof, in the manufacture of a substanceto increase ejaculatory latency. 20 21 20 21 A process for the préparation of a compound of general formula (I); 25 Z (I) 30 012372 102 wherein R1, R2, R4, R5, X and Z are as defmed in any one of ciaims 1 to 14comprising reacting a compound of general formula la NR1R2
    (la) 10 under suitable réaction conditions to form the compound of formula I, wherein thesuitable reaction conditions are: i) where R4/Rs are halogen, by réaction of (la) with a suitable haiogenatingagent in an inert solvent which does not adversely affect the reaction;- ii) where R4/R5 are -NO2, by reaction of (la) with a suitable nitrating agent inan inert solvent which does not adversely affect the reaction at, or below,room température; or ii) where R4/R5 is -SO2NR6R7 by reaction of an intermediate sulfonyl chloridewith the requisite amine of formula HNR6R7 in a suitable solvent. A process according.to cîaim 23 for preparing a compound of formula (iq), i.e. acompound of formuia I where R5 is -SO,NR6R7 and R4 is hydrogen, 15 22 012372 103
    comprising a) reacting a compound of formuia la, optionally in a suitable solvent, withchlorosulfonic acid to give a compound of formula XVIII
    followed by b) reacting with HNR6R7 to give the compound of formula (iq>. 23 A process according to claim 22 wherein the compound of formula XVIII is 10 generated in situ and reacted with HNR6R7 without isolation. 24 A process according to any one of daims 21 to 23 which further comprises thestep of preparing compounds of formuia (ia), by reacting compounds of formula(Ha) 012372 104
    «· with a compound of formula HNR1R2, or with a suitable sait form thereof, togetherwith a hydride reducing agent in a suitable solvent, to form the compound offormula (la). 25 An intermediate compound of formula (lia) or (XVIII) as defined in daims 21 to24, with the proviso that (1 la) may not be 2 ( (31, 41 - Methylenedioxy) phenoxy)benzaldehyde.
    wherein R1, R2, R4, R5, X and Z are as defined in any one of daims 1 to 14,comprising reacting compounds of formula II
    15 (II) 012372 105 with a compound of formula HNR’R2 or with a suitable sait form thereof, together with a hydride reducing agent in a suitable solvent. 27 A process according to ciaim 2é which further comprises coupling unaer suitable5 reaction conditions a compound of formula fil,
    wherein L is a suitable leaving group such as haiogen or a suifonate ester suchas trifluoromethanesulfonate or methanesulfonate, with a compound of formulaIV
    to give the compound of formula 11. 28 An intermediate compound of formula II as defined in ciaim 26, with the proviso15 that (11) may not be 2 - ( (31, 41 - Methylenedioxy) phenoxy) benzaldehyde or 2 ( (31,41 - Methylenedioxy) phenoxy) 5-fluorobenzaldehyde. 29 A compound of general formula (1), or pharmaceutically acceptable salts,solvatés or polymorphe thereof, wherein R1, R2, Y and Z are as defined in ciaim1; and R4 and Rs, which may be the same or different, are -(CH2)P-A’, wherein p is0, 1 or 2 and A’ is a polar group. 30 A compound according to ciaim 21, wherein the polar group has a δ-value morenégative than -0.1.
OA1200300056A 2000-08-31 2001-08-22 Phenoxybenzylamine derivatives as selective seotonin re-uptake inhibitors. OA12372A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0021593A GB0021593D0 (en) 2000-08-31 2000-08-31 Diphenyl ether compounds useful in therapy
GB0107116A GB0107116D0 (en) 2001-03-21 2001-03-21 Novel compounds

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OA12372A true OA12372A (en) 2006-04-17

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EP (1) EP1313701A1 (fr)
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IL154343A0 (en) 2003-09-17
HRP20030141A2 (en) 2003-04-30
DZ3414A1 (fr) 2002-03-07
AR031867A1 (es) 2003-10-08
TNSN01131A1 (fr) 2005-11-10
PL360743A1 (en) 2004-09-20
DOP2001000242A (es) 2002-05-15
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WO2002018333A1 (fr) 2002-03-07
EP1313701A1 (fr) 2003-05-28
UY26924A1 (es) 2002-03-22
PA8526701A1 (es) 2003-07-28
HUP0303385A2 (hu) 2004-03-01
MA26945A1 (fr) 2004-12-20
KR20030029889A (ko) 2003-04-16
CZ2003467A3 (cs) 2004-04-14
CA2420969A1 (fr) 2002-03-07
AP2001002265A0 (en) 2001-09-30
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