Claims
- 1. A compound selected from the group consisting of a compound of the formula ##STR22## wherein X is in the 5-, 6-, 7- or 8-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --SCF.sub.3 and --OCF.sub.3, R.sub.1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R.sub.2 is selected from the group consisting of thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl, pyrimidyl and tetrazolyl, all unsubstituted or substituted with alkyl of 1 to 4 carbon atoms and phenyl and phenyl substituted with at least one member of the group consisting of --OH, alkyl and alkoxy of 1 to 4 carbon atoms, --CF.sub.3, --NO.sub.2 and halogen, A is ##STR23## in which R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, phenyl and naphthyl, R.sub.5 is selected from the group consisting of pyridyl, indolyl, thienyl, oxazolyl, thiazolyl, pyrimidyl, benzo thienyl and benzothiazolyl unsubstituted or substituted with alkyl of 1 to 4 carbon atoms and their non-toxic, pharmaceutically acceptable salts with acids or bases.
- 2. A compound of claim 1 wherein X is in the 8-position.
- 3. A compound of claim 2 wherein X is --CF.sub.3
- 4. A compound of claim 1 wherein X is in the 7-position.
- 5. A compound of claim 4 wherein X is chlorine.
- 6. A compound of claim 1 wherein R.sub.1 is hydrogen.
- 7. A compound of claim 1 wherein R.sub.3 is hydrogen.
- 8. A compound of claim 1 wherein R.sub.2 is thiazolyl.
- 9. A compound of claim 1 wherein R.sub.4 is ethyl.
- 10. A compound of claim 1 wherein R.sub.5 is indolyl.
- 11. A compound of claim 1 wherein R.sub.5 is thiazolyl optionally substituted with alkyl of 1 to 5 carbon atoms.
- 12. A compound of claim 1 selected from the group consisting of 11H-indole-carboxylate and 12-propyl-5-thiazole-carboxylate in racemic or optically active form and their non-toxic, pharmaceutically acceptable salts with acids and bases.
- 13. An analgesic and anti-inflammatory composition comprising an analgesically and anti-inflammatorily effective amount of at least one compound selected from the group consisting of a compound of claim 1 and an inert pharmaceutical carrier.
- 14. A composition of claim 13 wherein in the compound X is in the 8-position.
- 15. A composition of claim 14 wherein in the compound X is --CF.sub.3.
- 16. A composition of claim 13 wherein in the compound X is in the 7-position.
- 17. A composition of claim 16 wherein in the compound X is chlorine.
- 18. A composition of claim 13 wherein in the compound R.sub.1 is hydrogen.
- 19. A composition of claim 13 wherein in the compound R.sub.3 is hydrogen.
- 20. A composition of claim 13 wherein in the compound R.sub.2 is thiazolyl.
- 21. A composition of claim 13 wherein in the compound R.sub.4 is ethyl.
- 22. A composition of claim 13 wherein in the compound R.sub.5 is indolyl.
- 23. A composition of claim 13 wherein in the compound R.sub.5 is thiazolyl optionally substituted with alkyl of 1 to 5 carbon atoms.
- 24. A composition of claim 13 wherein the active compound is selected from the group consisting of 1111-indole-carboxylate and 12-propyl-5-thiazole-carboxylate in racemic or optically active form and their non-toxic, pharmaceutically acceptable salts with acids and bases.
- 25. A method of relieving pain and inflammation in warm-blooded animals comprising administering to warm-blooded animals an analgesically and anti-inflammatorily effective amount of at least one compound selected from the group consisting of a compound of claim 1.
- 26. A method of claim 25 wherein in the active compound X is in the 8-position.
- 27. A method of claim 26 wherein in the active compound X is --CF.sub.3.
- 28. A method of claim 25 wherein in the active compound X is in the 7-position.
- 29. A method of claim 28 wherein in the active compound X is chlorine.
- 30. A method of claim 25 wherein in the active compound R.sub.1 is hydrogen.
- 31. A method of claim 25 wherein in the active compound R.sub.3 is hydrogen.
- 32. A method of claim 25 wherein in the active compound R.sub.2 is thiazolyl.
- 33. A method of claim 25 wherein in the active compound R.sub.4 is ethyl.
- 34. A method of claim 25 wherein in the active compound R.sub.5 is indolyl.
- 35. A method of claim 25 wherein in the active compound R.sub.5 is thiazolyl optionally substituted with alkyl of 1 to 5 carbon atoms.
- 36. A method of claim 25 wherein the active compound is selected from the group consisting of 1111-indole-carboxylate and 12-propyl-5-thiazole-carboxylate in racemic or optically active form and their non-toxic, pharmaceutically acceptable salts with acids and bases.
Priority Claims (2)
Number |
Date |
Country |
Kind |
8416573 |
Oct 1984 |
FRX |
|
8511389 |
Jul 1985 |
FRX |
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PRIOR APPLICATION
This application is a continuation-in-part of U.S. patent application Ser. No. 030,680 filed Mar. 24, 1987, now U.S. Pat. No. 4,845,105, which is a continuation-in-part of U.S. patent application Serial No. 831,356 filed Feb. 20, 1986, now abandoned, which is a continuation-in-part of U.S. patent application Ser. No.790,064 filed Oct. 22, 1985, now U.S. Pat. No. 4,735,951.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
4486438 |
Clemence et al. |
Dec 1984 |
|
4735951 |
Cleence et al. |
May 1988 |
|
4845105 |
Clemence et al. |
Jul 1989 |
|
Foreign Referenced Citations (3)
Number |
Date |
Country |
0214004 |
Mar 1987 |
EPX |
2551437 |
Mar 1985 |
FRX |
2572404 |
May 1986 |
FRX |
Continuation in Parts (3)
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Number |
Date |
Country |
Parent |
30680 |
Mar 1987 |
|
Parent |
831356 |
Feb 1986 |
|
Parent |
790064 |
Oct 1985 |
|