Tetrahydrocarbazole 1-alkanoic acids

Details Tetrahydrocarbazole 1-alkanoic acids Tetrahydrocarbazole 1-alkanoic acids

C - Chemistry, Metallurgy

07

D

167/233, 260/318

C07D 209/82 (2006.01) A61K 31/40 (2006.01) C07D 403/00 (2006.01)

Patent

CA 1299577

TITLE OF THE INVENTION TETRAHYDROCARBAZOLE 1-ALKANOIC ACIDS ABSTRACT OF THE DISCLOSURE Tetrahydrocarbazole 1-alkanoic acids are disclosed. The compounds act as prostaglandin and thromboxane antagonists and are useful in treating asthma, diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion and dysmenorrhea and as cytoprotective agents, and have the following general formula: Image I wherein: R1, R2, R3, R4, R5 and R6 are each independently selected from: (1) hydrogen; (2) alkyl having 1 to 6 carbon atoms; (3) alkenyl having 2 to 6 carbon atoms; (4) -(CH2)nM wherein n is O to 3 and M is a) OR13; b) halogen; c) CF3; d) SR13; e) phenyl or substituted phenyl wherein substituted phenyl i s as defined below in the definition of R13; 5012P/5011A 17323IA f) COOR14; g) -?-R15; h) -NH-?-R16 wherein R16 is C1 to C6 alkyl, benzyl or phenyl; i) -NR14R14; j) -NHSO2R17 wherein R17 is C1 to C6 alkyl, 4-methylphenyl, phenyl, or CF3; k) -?-CH2OH; l) -SOR13; CONR14R14; n) -SO2NR14R14; o) -SO2R13; p) NO2 ; q) -O-?-R15; r) -O-?-NR14R14; s) - O-?-OR16; t) CN; u) N3; R7 is H or alkyl of 1 to 6 carbons; R8 is H or alkyl of 1 to 6 carbon atoms; each R9 is independently H, OH, C1 to C4-O-alkyl or alkyl of 1 to 4 carbons; 5012P/5011A 17323IA R10 is COOH; CH2OH; CHO; NHSO2R11 wherein R11 is OH, alkyl or alkoxy of 1 to 6 carbons, perhaloalkyl of 1 to 6 carbons, phenyl or phenyl substituted by alkyl or alkoxy groups of 1 to 3 carbons, halogen, hydroxy, COOH, CN, formyl or acyl to 1 to 6 carbons; CONHSO2R11; hydroxymethylketone; CN; or CON(R9)2; r is 1 to 6; each R13 independently is H; C1 to C6 alkyl; benzyl; phenyl or substituted phenyl wherein the substituents are C1 to C3 alkyl, halogen, CN, CF3, COOR14, CH2COOR14, C1 to C3 alkoxy, or C1 to C4 perfluoroalkyl; each R14 is independently H, phenyl, benzyl or C1 to C6 alkyl; and, each R15 independently is H, (CH2)mCOOR14 wherein m is 0 to 4, C1 to C6 alkyl, CF3, phenyl, or substituted phenyl wherein substituted phenyl is as defined above in the definition of R13; or a pharmaceutically acceptable salt thereof.

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