Tetrahydrocarbazole esters

Details Tetrahydrocarbazole esters Tetrahydrocarbazole esters

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 1330090

TITLE OF THE INVENTION TETRAHYDROCARBAZOLE ESTERS ABSTRACT OF THE DISCLOSURE Tetrahydrocarbazole esters 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. The compounds of the present invention have the 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 carbons; (3) alkenyl having 2 to 6 carbons; (4) -(CH2)nM wherein n is 0 to 3 and M is a) OR11; b) halogen; c) CF3; d) SR11; e) phenyl or substituted phenyl wherein the substituents are selected from the group consisting of C1-C3 alkyl, halogen, CN, CF3, COOR12, CH2COOR12 and C1-C3 alkoxy; f) COOR12; g) Image ; h) Image ; i) -NR12R12; j) -NRSO2R15; k) Image ; l) SOR11; m) -CONR12R12; n) -SO2NR12R12; o) -SO2R11; p) NO2; q) Image ; r) Image ; s) Image ; t) CN; u) N3; provided that when R1, R2, R3 or R4 is alkyl having 1 to 6 carbons, it is not located at position 6; R7 is H or alkyl of 1 to 6 carbons; R8 is H or alkyl of 1 to 6 carbons; each R9 is independently H, OH, C1 to C4-O- alkyl or alkyl of 1 to 4 carbons; R10 is lower alkyl, substituted or unsubstituted 2-phenethyl wherein the substituents are selected from the group consisting of C1-C3 alkyl, halogen, CN, CF3, COOR12, CH2COOR12 and C1-C3 alkoxy; substituted or unsubstituted benzyl wherein the substituents are selected from the group consisting of C1-C3 alkyl, halogen, CN, CF3, COOR12, CH2COOR12 and C1-C3 alkoxy; or substituted or unsubstituted phenyl wherein the substituents are as defined above; each R11 is independently H; C1 to C6 alkyl; benzyl; phenyl or substituted phenyl wherein the substituents are as defined above; each R12 is independently H, phenyl, benzyl or C1 to C6 alkyl; and, each R13 is independently H, (CH2)mCOOR12 wherein m is 0 to 4, C1 to C6 alkyl, CF3, phenyl, or substituted phenyl wherein the substituents are as defined above; each R14 is C1 to C6 alkyl, benzyl or phenyl; each R15 is C1 to C6 alkyl, 4-methylphenyl, phenyl, or CF3; r is 1 to 6 or a pharmaceutically acceptable salt thereof.

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