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US 4,906,654 AGranted
Cyclohept[b]indoleakanoic acids, pharmaceutical compositions and use
AssigneeMerck Frosst Canada, Inc.
InventorsJohn W. Gillard, Howard E. Morton, Yvan Guindon, Yves Girard, Christiane Yoakim
Life of this patent
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Abstract
Cyclohept[b]indolealkanoic acids and acid derivatives 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, dysmenorrhea and nephrotoxicity caused by cyclosporin A and as cytoprotective agents.
Claims10
A compound of the formula:
- ##STR33## wherein:
- A is --(CR.sup.9 R.sup.10).sub.r R.sup.11 ;
- R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each independently selected from:
- (1) hydrogen;
- (2) alkyl having 1 to 6 carbon atoms;
- (3) alkenyl having 2 to 6 carbon atoms;
- (4) --(CH.sub.2).sub.n M wherein n is 0 to 3 and M is
- (a) --C(O)R.sup.15 ;
- (b) --C(O)NR.sup.17 R.sup.17 ;
- (c) --CN;
- (d) --C(O)R.sup.16 ;
- (e) --C(O)CH.sub.2 OH (hydroxymethyl ketone);
- (f) --CF.sub.3 ;
- (g) --R.sup.14 ;
- (i) --OR.sup.12 ;
- (j) --OC(O)R.sup.16 ;
- (k) --OC(O)NR.sup.17 R.sup.17 ;
- (l) --OC(O)OR.sup.18 ;
- (m) --S(O).sub.2 NR.sup.17 R.sup.17 ;
- (n) --NR.sup.17 R.sup.17 ;
- (o) --NHC(O)R.sup.16 ;
- (p) --NHS(O).sub.2 R.sup.13 ;
- (q) --N.sub.3 ;
- (r) --NO.sub.2 ;
- or
- (s) -halogen;
- each R.sup.7 is independently H or C.sub.1 to C.sub.6 alkyl;
- each R.sup.8 is independently H or C.sub.1 to C.sub.6 alkyl;
- each R.sup.9 is independently H or C.sub.1 to C.sub.6 alkyl;
- each R.sup.10 is independently H, OH, C.sub.1 to C.sub.4 alkoxy, or C.sub.1 to C.sub.4 alkyl;
- R.sup.11 is --C(O)OR.sup.19 ;
- each R.sup.12 is independently H, C.sub.1 to C.sub.6 alkyl, benzyl, or R.sup.14 ;
- each R.sup.13 is independently C.sub.1 to C.sub.6 alkyl, CF.sub.3, or R.sup.14 ;
- each R.sup.14 is independently phenyl, mono-substituted phenyl, or di-substituted phenyl wherein the substituents are independently, C.sub.1 to C.sub.3 alkyl, C.sub.1 to C.sub.3 perfluoroalkyl, C.sub.1 to C.sub.3 alkoxy, halogen, CN, --C(O)OR.sup.15, or --CH.sub.2 --C(O)OR.sup.15 ;
- each R.sup.15 is independently H, phenyl, benzyl or C.sub.1 to C.sub.6 alkyl;
- each R.sup.16 independently is H, R.sup.13 or (CH.sub.2).sub.m C(O)OR.sup.15 ;
- each R.sup.17 is independently R.sup.12
- each R.sup.18 is independently C.sub.1 to C.sub.6 alkyl, benzyl or phenyl;
- each R.sup.19 is H, C.sub.1 to C.sub.6 alkyl, R.sup.14, R.sup.21, or R.sup.22 ;
- R.sup.21 is --CH.sub.2 --R.sup.14 ;
- R.sup.22 is --CH.sub.2 --CH.sub.2 --R.sup.14
- m is 0 to and
- r is 0 to 6.
40 more elements
Dependencies are inferred from the claim text.