Claims
- 1. A compound selected from the group consisting of a compound of the formula ##STR29## 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 optionally 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 either ##STR30## 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 and aryl, R.sub.5 is selected from the group consisting of phenyl, naphthyl, pyridinyl, alkyl of 1 to 4 carbon atoms, alkyl substituted with --NH.sub.2, --NHAlk or ##STR31## alkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms substituted with phenyl or naphthyl, Alk and Alk' are alkyl of 1 to 6 carbon atoms or, when R.sub.1 is hydrogen, A is ##STR32## R.sub.4a, R.sub.2a and R.sub.3a are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, phenyl, naphthyl, ##STR33## or R.sub.2a and R.sub.3a together form acetonide, R.sub.4a is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and aryl, R.sub.5a is selected from the group consisting of alkyl of 1 to 4 carbon atoms and aryl with the proviso that when X is 8--CF.sub.3, R.sub.1 and R.sub.3 are hydrogen, R.sub.2 is 2-thiazolyl, R.sub.4 is methyl, R.sub.5 is not methyl 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.2a and R.sub.3a are hydrogen and R.sub.4a is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms phenyl and naphthyl.
- 7. A compound of claim 1 wherein R.sub.1 is hydrogen.
- 8. A compound of claim 1 wherein R.sub.3 is hydrogen.
- 9. A compound of claim 1 wherein R.sub.2 is thiazolyl.
- 10. A compound of claim 1 selected from the group consisting of 2-(1,2-dihydroxy-ethyl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable salts with acids and bases.
- 11. A compound of claim 1 selected from the group consisting of 2-(1,2-dihydroxy-propyl)-4-hyroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable salts with acids and bases.
- 12. A compound of claim 1 selected from the group consisting of 2-[1,2-bis-(1-oxopropoxy)-ethyl]-4-hydroxy-N-(2-thiiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its 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 its salts 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.2a and R.sub.3a are hydrogen and R.sub.4a is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms phenyl and naphthyl.
- 19. A composition of claim 13 wherein in the compound R.sub.1 is hydrogen.
- 20. A composition of claim 13 wherein in the compound R.sub.3 is hydrogen.
- 21. A composition of claim 13 wherein in the compound R.sub.2 is thiazolyl.
- 22. A composition of claim 13 wherein the active ingredient is selected from the group consisting of 2-(1,2-dihydroxy-ethyl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable salts with acids and bases.
- 23. A composition of claim 13 wherein the active ingredient is selected from the group consisting of 2-(1,2-dihydroxy-propyl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable salts with acids and bases.
- 24. A composition of claim 13 wherein the active ingredient is selected from the group consisting of 2-/1,2-bis-(1-oxopropoxy)-ethyl/-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl 3-quinoline carboxamide and its non-toxic, pharmaceutically acceptable salts with acids and bases.
- 25. An analgesic and anti-inflammatory composition comprising an analgesically and anti-inflammatorily effective amount of B isomer of 4-hydroxy-2-(1-hydroxypropyl)-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts and an inert pharmaceutical carrier or excipient.
- 26. 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 and its salts.
- 27. A method of claim 26 wherein in the active compound X is in the 8-position.
- 28. A method of claim 27 wherein in the active compound X is --CF.sub.3.
- 29. A method of claim 26 wherein in the active compound X is in the 7-position.
- 30. A method of claim 29 wherein in the active compound X is chlorine.
- 31. A method of claim 26 wherein in the active compound R.sub.2a and R.sub.3a are hydrogen and R.sub.4a is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms phenyl and naphthyl.
- 32. A method of claim 26 wherein the active compound is selected from the group consisting of 2-(1,2-dihydroxyethyl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable salts with acids and bases.
- 33. A method of claim 26 wherein the active compound is selected from the group consisting of 2-(1,2-dihydroxypropyl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable salts with acids and bases.
- 34. A method of claim 26 wherein the active compound is selected from the group consisting of 2-/1,2-bis-(1-oxo-propoxy)-ethyl)-4-hydroxy-N-(2-thiazolyl)-8-trifluoromethyl 3-quinoline carboxamide and its non-toxic, pharmaceutically acceptable salts with acids and bases.
- 35. A method of claim 26 wherein in the active compound R.sub.1 is hydrogen.
- 36. A method of claim 26 wherein in the active compound R.sub.3 is hydrogen.
- 37. A method of claim 26 wherein in the active compound R.sub.2 is thiazolyl.
- 38. A method of relieving pain and inflammation comprising administering to warm-blooded animals an analgesically and anti-inflammatorily effective amount of the B isomer of 4-hydroxy-2-(1-hydroxypropyl)-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable salts.
- 39. A compound selected from the group consisting of the B isomer of 4-hydroxy-2-(1-hydroxypropyl)-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable salts.
- 40. A compound of claim 39 which is the B isomer of 4-hydroxy-2-(1-hydroxypropyl)-N-(2-thiazolyl)-8-trifluoromethyl-3-quinoline-carboxamide.
Priority Claims (2)
Number |
Date |
Country |
Kind |
84 16573 |
Oct 1984 |
FRX |
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85 11389 |
Jul 1985 |
FRX |
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PRIOR APPLICATIONS
This application is a continuation-in-part of U.S. patent application Ser. No. 831,356 filed Feb. 20, 1986 now abandoned which is a continuation-in-part of U.S. patent application Ser. No. 890,081 filed July 24, 1946 now abandoned and 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 |
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4636512 |
Clemence et al. |
Jan 1987 |
|
4735951 |
Clemence et al. |
May 1988 |
|
Foreign Referenced Citations (4)
Number |
Date |
Country |
3320102 |
Dec 1983 |
DEX |
2551437 |
Mar 1985 |
FRX |
2572404 |
May 1986 |
FRX |
2123817 |
Feb 1984 |
GBX |
Non-Patent Literature Citations (1)
Entry |
Clemence et al., J. Heterocycl. Chem., 21(5), pp. 1345-1353, (1984). |
Continuations (1)
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Number |
Date |
Country |
Parent |
890081 |
Jul 1946 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
831356 |
Feb 1986 |
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Parent |
790064 |
Oct 1985 |
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