6-Benzyl-2H-pyridazin-3-one derivatives,their preparation and their use as inhibitors of prostaglandin G/H synthase I and II (COX I and COX II)

摘要

Compounds of formula I: <CHEM> where: the dashed line denotes an optional bond; R1 is H, halo, alkyl, alkyloxy, amino, alkylamino, dialkylamino, or acylamino; R3 and R4 are independently H, halo, alkyl, alkyloxy, or hydroxy; R5 is H, halo, alkyl, alkylthio, alkyloxy, alkenyloxy, alkynyl, or alkenyl; provided that at least one of R1, R3, R4, and R5 is H; R7 is H, alkyl, cyano, or amido; R10 is a group represented by formula (A), (B), or (C); <CHEM> where: X is O or S; R12, R13, R15, and R16 are independently H, halo, alkyl, alkyloxy, or alkylthio; and R14 is H, halo, alkyl, alkylthio, alkyloxy, alkenyloxy, alkynyl, alkenyl, or -SO2R17 where R17 is alkyl, or -SO2NR18R19 where R18 and R19 are independently H or alkyl; provided that at least two of R12, R13, R14, R15, and R16 are H, and that if only two of R12, R13, R15, and R16 are H, the non-hydrogen substituents are not all adjacent; and at least one of R12 and R16 is H when neither R1 nor R3 are H; and R20 is H, alkyl, haloalkyl, hydroxyalkyl, or alkenyl; and their pharmaceutically acceptable salts are inhibitors of prostaglandin G/H synthase and are anti-inflammatory and analgesic agents.