Benzimidazole derivatives

Details Benzimidazole derivatives Benzimidazole derivatives

C - Chemistry, Metallurgy

07

D

C07D 235/02 (2006.01) A61K 31/41 (2006.01) A61K 31/435 (2006.01) A61K 31/495 (2006.01) A61K 31/535 (2006.01) C07C 211/52 (2006.01) C07C 233/65 (2006.01) C07C 309/65 (2006.01) C07C 309/66 (2006.01) C07C 309/72 (2006.01) C07D 235/06 (2006.01) C07D 235/08 (2006.01) C07D 235/10 (2006.01) C07D 235/18 (2006.01) C07D 235/28 (2006.01) C07D 401/04 (2006.01) C07D 401/12 (2006.01) C07D 403/12 (2006.01) C07D 413/12 (2006.01) C07D 417/04 (2006.01) C07F 9/6506 (2006.01)

Patent

CA 2050908

ABSTRACT Compounds of general formula I: Image I wherein: each of R1 and R2 represents independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, halogen, CN, CO2H, CO2(C1-C6 alkyl), CO2(C3-C8)cycloalkyl, CONH2, CHO, CH2OH, CF3, C1-C6 alkoxy, C1-C6 alkylthio, SO(C1-C6)- alkyl, SO2(C1-C6 alkyl), SO3H, NH2, NHCOMe, or NO2 or R1 and R2 together with the carbon atoms to which they are attached form a fused phenyl ring; R3 represents a hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkoxy (C1-C6 alkyl), C1-C6 alkylthio (C1-C6 alkyl), SO(C1-C6 alkyl), SO2(C1-C6 alkyl), CF3, phenyl (C1-C6 alkyl), thiophenyl, thiazole, pyridyl or a Image group where.in R4 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, halogen, OH, SH, CN, CO2H, CO2(C1-C6 alkyl), CONH2, CHo, CH20H, CF3, C1 C6 alkoxy, 1 6 alkylthio, SO(C1-C6 alkyl), SO2(C1-C6 alkyl), NH2, NHCOMe, or No2; each of R5 and R6 represents independently hydroyen, C1-6 alkyl, C2-C6 alkenyl, CO2(C1-C6 alkyl), C1-C6 alkylthio, SO(C1 C6 alkyl), SO2(C1-C6 alkyl), C1-C6 alkylthio (C1 C6 alkyl), C1-C6 alkoxy (Cl-C6 alkyl) phenyl (C1-C6 alkyl) and thiophenyl; k is an integer from 0 to 2; each of R7 and R8 independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenYl, C1-C6 alkoxy, C16 alkylthio, C1-C6 alkoxy (C1-C6 alkyl), C1-C6 alkylthio (C1-C6 alkyl), halogen, CF3, CN, OH, SH, CH2OH, CH2SH or CONH2; Image V represents a) a YNR9R10 group wherein Y is SO2, PO2, CO or CS and each of R9 and R10 is independently hydrogen, C1-C18 alkyl, C2-C18 alkenyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, phenyl (C1-C6 alkyl), adamantyl, decalynyl, naphthyl, C3-C8 cycloalkyl (C1-C6 alkyl), C4-C8 cycloalkenyl (Cl-C6 alkyl) or a group G wherein G represents a group: Image or a group: Image wherein n is an integer of from 1 to 6 and each of R11, R12 and R13 is independently hydrogen, halogen, C1-C18 alkyl, C2-C18 alkenyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, phenyl (C1-C6 alkyl), C3-C8 cycloalkyl (C1-C6 alkyl), C4-C8 cycloalkenyl (C1-C6 alkyl) or a C1-C6 alkoxy, benzoxy, C1-C6 alkylthio, benzthio or benzoyl; or b) a group Image group wherein 1 is an integer from 1 to 3, Y represents SO2, PO2, CO or CS, each of R14 and R15 independently represents hydrogen, C1-C18 alkyl, C2-C18 alkenyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, phenyl (C1-C6 alkyl), C3-C8 cycloalkyl (C1-C6 alkyl), C4-C8 cycloalkenyl (C1-C6 alkyl) or a group G as defined above, T represents O, S, NR16, or CH2R16 wherein R16 represents hydrogen, C1-C18 alkyl, C2-C18 alkenyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, phenyl (C1-C6 alkyl), C3-C8 cycloalkyl (C1-C6 alkyl), C4-C8 cycloalkenyl (C1-C6 alkyl) or a group G as defined above; c) a group Image or a group Image wherein h is an integer from 1 to 2, m is an integer from 0 to 2, Y represents SO2, PO2, CO or CS, each of R17 and R18 independently represents hydrogen, halogen, C1-C18 alkyl, C2-C18 alkenyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, phenyl (C1-C6 alkyl), C3-C8 cycloalkyl (C1-C6 alkyl), C4-C8 cycloalkenyl (C1-C6 alkyl), C1-C6 alkoxy, benzoxy, C1-C6 alkylthio, benzthio or benzoyl; d) a ZR19 group wherein Z represents tetrazole, co, CO2, NR20CO, NR20CO2, SO2, NR20SO2, O2C, or OCONR20 and each of R19 and R20 independently represents hydrogen, C1-C18 alkyl, C2-C18 alkenyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, adamantyl, decalynyl, phenyl (C1-C6 alkyl), C3-C8 cycloalkyl (C1-C6 alkyl), C4-C8 cycloalkenyl (C1-C6 alkyl), naphthyl, or a group G as defined above; e) an NR21POR22R23 group wherein each of R21, R22 and R23 independently represents hydrogen, C1-C18 alkyl, C2-C18 alkenyl, C3-C8 cycloalkyl, C4-C8 cycloalkenyl, adamantyl, decalynyl, phenyl (C1-C6 alkyl), C3-C8 cycloalkyl (C1-C6 alkyl), C4-C8 cycloalkenyl (C1-C6 alkyl), naphthyl or a group G as defined above; and their pharmaceutically and veterinarily acceptable acid addition salts and hydrates are antagonists of platelet activating factor (PAF) and as such are useful in the treatment or amelioration of various diseases or disorders mediated by PAF.

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