Carboxylic acid derivatives, process for producing the same and drugs containing the same as the active ingredient

A carboxylic acid derivative of formula (1)

• 72
• wherein
• R1 is COOH, COOR6, CH2OH, CONHSO2R7 or CONR8R9,
• R6 is C1-6 alkyl, (C1-4 alkylene)-R16,
• R7 is (1) C1-4 alkyl, or (2) substituted by 1-2 of substitutes selected form C1-4 alkyl, C1-4 alkoxy and halogen atom or unsubstituted (2-1) C6-12 mono- or bi-carbocyclic ring or (2-2) 5-15 numbered mono- or bi-heterocyclic ring containing at least one of hetero atom selected from nitrogen, oxygen and sulfur, or (3) C1-4 alkyl substituted by the above substituents or unsubstituted carbocyclic ring or heterocyclic ring,
• R8 and R9 each independently, is hydrogen or C1-4 alkyl,
• R16 is hydroxy, C1-4 alkoxy, COOH, C1-4 alkoxycarbonyl, CONR8R9,
• A is C1-6 alkylene or —(C1-3 alkylene)w-G-(C1-3 alkylene)-,
• w is 0 or 1,
• G is oxygen, sulfur or NR10,
• R10 is hydrogen or C1-4 alkyl,
• R2 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, halogen atom, CFa, cyano, nitro, hydroxy, NR11R12, CONR11R12, SO2NR11R12, or —S(O)x—(C1-6)alkyl,
• m is 0, 1 or 2, when m is 2, then two R2 may be same or difference,
• R11 and R12 each independently, hydrogen or C1-4 alkyl,
• x is 0, 1 or 2,
• B ring is C5-7 mono-carbocyclic ring or 5-7 membered mono-heterocyclic ring containing at least one of nitrogen, oxygen and sulfur,
• R3 is hydrogen or C1-4 alkyl,
• R4 is (1) C1-8 alkyl, (2) C2-8 alkenyl, (3) C2-8 alkynyl, (4) C3-6 cycloalkyl, (5) hydroxy, (6) C1-4 alkoxy, (7) C1-4 alkoxy(C1-4)alkoxy, or (8) C1-8 alkyl substituted by 1-2 of substitutes selected from halogen atom, hydroxy, C1-6 alkoxy, C1-4 alkoxy(C1-4)alkoxy, phenyl and C3-6 cycloalkyl,
• R5 is substituted by 1-2 of R13 or unsubstituted C5-10 mono- or bi-carbocyclic ring or 5-10 membered mono- or bi-heterocyclic ring containing at least one of nitrogen, oxygen and sulfur,
• R18 is C1-6 alkyl, C1-6 alkoxy, halogen atom, CF3, cyano, C1-4 alkoxy(C1-4)alkyl, phenyl, phenyl(C1-6)alkyl, —(C1-4 alkylene)y-J-(C1-8 alkylene)x-R14, benzoyl or thiophenecarbonyl and two R18 may be same or difference,
• y is 0 or 1,
• z is 0 or 1,
• R14 is phenyl or pyridyl,
• J is oxygen, S(O)t or NR15,
• t is 0, 1 or 2,
• R15 is hydrogen, C1-4 alkyl or acetyl;
• or non-toxic salts.