US4299831A
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2-Trifluoromethyl-3-quinoline carboxamides, analgesic and anti-inflammatory compositions and methods employing them
Assignee: Sanofi Aventis France
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Filing: 1979-11-27
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Granted: 1981-11-10
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Expires: 1999-11-27
Abstract
Abstract Novel 3-quinoline carboxamides of the formula ##STR1## wherein X' is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, halogen, straight or branched alkyl and alkoxy of 1 to 5 carbon atoms, --CF 3 , --SCF 3 and --OCF 3 , R 1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R 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 optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 4 carbon atoms, --CF 3 , --NO 2 and halogen and their non-toxic, pharmaceutically acceptable acid addition salts having analgesic and anti-inflammatory activity and novel intermediates and process for their preparation.
Inventors
- 👤 Francois Clemence
- 👤 Roger Deraedt
- 👤 Andre Allais
- 👤 Odile Le Martret
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:22
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
109 words
A compound selected from the group consisting of 3-quinoline carboxamides of the formula ##STR11## wherein X' is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, halogen, straight or branched alkyl and alkoxy of 1 to 5 carbon atoms, --CF 3 , --SCF 3 and --OCF 3 , R 1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R 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 their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
109 words
A compound selected from the group consisting of 3-quinoline carboxamides of the formula ##STR11## wherein X' is in the 5,6,7 or 8-position and is selected from the group consisting of hydrogen, halogen, straight or branched alkyl and alkoxy of 1 to 5 carbon atoms, --CF 3 , --SCF 3 and --OCF 3 , R 1 is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms, R 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 their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
53 words
A compound of claim 1 wherein X' is selected from the group consisting of halogen, --CF 3 , --SCF 3 and --OCF 3 and R 2 ' is selected from the group consisting of thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl and pyrimidyl, all optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 4
Dependent Claim
11 words
A compound of claim 1 wherein X' is --CF 3 .
Claim 5
Dependent Claim
11 words
A compound of claim 1 wherein X' is 8--CF 3 .
Claim 6
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is hydrogen.
Claim 7
Dependent Claim
11 words
A compound of claim 1 wherein R 2 ' is thiazolyl.
Claim 8
Dependent Claim
11 words
A compound of claim 1 wherein R 2 ' is oxazolyl.
Claim 9
Dependent Claim
21 words
A compound of claim 1 wherein R 2 ' is isoxazolyl optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 10
Dependent Claim
11 words
A compound of claim 8 wherein R 2 ' is 5-methylisoxazolyl.
Claim 11
Dependent Claim
11 words
A compound of claim 1 wherein R 2 ' is pyrimidyl.
Claim 12
Dependent Claim
21 words
A compound of claim 1 wherein R 2 ' is imidazolyl optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 13
Dependent Claim
11 words
A compound of claim 11 wherein R 2 ' is 1-methyl-1H-imidazolyl.
Claim 14
Dependent Claim
21 words
A compound of claim 1 wherein R 2 ' is tetrazolyl optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 15
Dependent Claim
28 words
A compound of claim 1 selected from the group consisting of 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(oxazol-2-yl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(5-methyl-isoxazol-3-yl)-3-quinoline-carboxamide 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(2-pyridinyl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1-methyl-1H-imidazol-2-yl)-3-quinoline-carboxamide 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1H-tetrazol-5-yl)-3-quinoline-carboxamide, 2,7-bis-(trifluoromethyl)-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-6-isopropyl-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-6-methoxy-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 16
Dependent Claim
10 words
A compound of claim 1 which is the 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(2-thiazolyl)-3-quinoline carboxamide.
Claim 17
Dependent Claim
23 words
An anti-inflammatory and analgesic composition comprising an analgesically and anti-inflammatorily effective amount of at least one compound of claim 1 and an excipient.
Claim 18
Dependent Claim
53 words
A composition of claim 16 wherein X' is selected from the group consisting of halogen, --CF 3 , --SCF 3 and --OCF 3 and R 2 ' is selected from the group consisting of thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl and pyrimidyl, all optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 19
Dependent Claim
11 words
A composition of claim 16 wherein X' is --CF 3 .
Claim 20
Dependent Claim
11 words
A composition of claim 16 wherein X' is 8--CF 3 .
Claim 21
Dependent Claim
10 words
A composition of claim 16 wherein R 1 is hydrogen.
Claim 22
Dependent Claim
11 words
A composition of claim 16 wherein R 2 ' is thiazolyl.
Claim 23
Dependent Claim
11 words
A composition of claim 16 wherein R 2 ' is oxazolyl.
Claim 24
Dependent Claim
21 words
A composition of claim 16 wherein R 2 ' is isoxazolyl optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 25
Dependent Claim
11 words
A composition of claim 16 wherein R 2 ' is 5-methyl-isoxazolyl.
Claim 26
Dependent Claim
11 words
A composition of claim 16 wherein R 2 ' is pyrimidyl.
Claim 27
Dependent Claim
21 words
A composition of claim 16 wherein R 2 ' is imidazolyl optionally sbustituted with alkyl of 1 to 4 carbon atoms.
Claim 28
Dependent Claim
11 words
A compound of claim 16 wherein R 2 ' is 1-methyl-1H-imidazolyl.
Claim 29
Dependent Claim
21 words
A composition of claim 16 wherein R 2 ' is tetrazolyl optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 30
Dependent Claim
28 words
A composition of claim 16 selected from the group consisting of 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(oxazol-2-yl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(5-methyl-isoxazol-3-yl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(2-pyridinyl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1-methyl-1H-imidazol-2-yl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1H-tetrazol-5-yl)-3-quinoline-carboxamide, 2,7-bis-(trifluoromethyl)-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-6-isopropyl-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-6-methoxy-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 31
Dependent Claim
8 words
A composition of claim 16 comprising 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(2-thiazolyl)-3-quinoline carboxamide.
Claim 32
Dependent Claim
29 words
A method of relieving pain and inflammation in warm-blooded animals comprising administering to warm-blooded animals an analgesically and anti-inflammatorilly effective amount of at least one compound of claim 1.
Claim 33
Dependent Claim
53 words
The method of claim 31 wherein X' is selected from the group consisting of halogen, --CF 3 , --SCF 3 and --OCF 3 and R 2 ' is selected from the group consisting of thiazolyl, 4,5-dihydrothiazolyl, pyridinyl, oxazolyl, isoxazolyl, imidazolyl and pyrimidyl, all optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 34
Dependent Claim
11 words
The method of claim 31 wherein X' is --CF 3 .
Claim 35
Dependent Claim
11 words
The method of claim 31 wherein X' is 8--CF 3 .
Claim 36
Dependent Claim
10 words
The method of claim 31 wherein R 1 is hydrogen.
Claim 37
Dependent Claim
11 words
The method of claim 31 wherein R 2 ' is thiazolyl.
Claim 38
Dependent Claim
11 words
The method of claim 31 wherein R 2 ' is oxazolyl.
Claim 39
Dependent Claim
21 words
The method of claim 31 wherein R 2 ' is isoxazolyl optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 40
Dependent Claim
11 words
The method of claim 31 wherein R 2 ' is 5-methylisoxazolyl.
Claim 41
Dependent Claim
11 words
The method of claim 31 wherein R 2 ' is pyrimidyl.
Claim 42
Dependent Claim
21 words
The method of claim 31 wherein R 2 ' is imidazolyl optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 43
Dependent Claim
11 words
The method of claim 31 wherein R 2 ' is 1-methyl-1H-imidazolyl.
Claim 44
Dependent Claim
21 words
The method of claim 31 wherein R 2 ' is tetrazolyl optionally substituted with alkyl of 1 to 4 carbon atoms.
Claim 45
Dependent Claim
32 words
The method of claim 31 wherein the compound is selected from the group consisting of 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(oxazol-2-yl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(5-methyl-isoxazol-3-yl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(2-pyridinyl)-3-quinoline-carboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1-methyl-1H-imidazol-2-yl)-3-quinolinecarboxamide, 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1H-tetrazol-5-yl)-3-quinoline-carboxamide, 2,7-bis-(trifluoromethyl)-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-6-isopropyl-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide, 2-trifluoromethyl-6-methoxy-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 46
Dependent Claim
10 words
The method of claim 31 wherein the compound is 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(2-thiazolyl)-3-quinoline-carboxamide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-11-09 | 1985-05-11 | 1985-11-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-09 | 1989-05-11 | 1989-11-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-09 | 1993-05-11 | 1993-11-10 | $7700.00 | Window Closed / Lapsed |