Patent EP0083020A2 successfully refreshed from Google Patents.
US4450167A
Expired / Lapsed
US
⏱️ 0.0 years remaining
3-Quinoline carboxamides having anxiolytic activity
Assignee: Sanofi Aventis France
•
Filing: 1982-07-15
•
Granted: 1984-05-22
•
Expires: 2002-07-15
Abstract
Abstract Novel 3-quinoline-carboxamides of the formula ##STR1## wherein R is in 6 or 7-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, --CF 3 , --SCF 3 and CH 3 S--, R 1 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, phenyl and benzyl, R 2 is --NHR 4 , R 4 is selected from the group consisting of alkyl of 2 to 6 carbon atoms, substituted aryl of 6 to 10 carbon atoms and substituted heterocycle of an aromatic character of 3 to 5 carbon atoms with the proviso that when R 4 is a mono substituted aryl or heterocycle, the substituent is different from R of the quinoline when it is a halogen and R 3 is selected from the group consisting of hydrogen and --OH and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable anxiolytic properties capable of lessening emotional reactions and diminishing states of psychic tension and their preparation.
Inventors
- 👤 Odile Le Martret
- 👤 Daniel Humbert
- 👤 Peter F. Hunt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 13:35
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D401/00; C07D401/02; C07D401/12; A; A61; A61P; A61P25/00; A61P25/20; C07D215/54; C07D215/56
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
87 words
A compound selected from the group consisting of 3-quinoline-carboxamides of the formula ##STR5## wherein R is in 6 or 7-position and is selected from the group consisting of hydrogen, halogen, and alkoxy of 1 to 6 carbon atoms R 1 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, phenyl and benzyl, R 2 is --NHR 4 , R 4 is alkyl of 2 to 6 carbon atoms, and R 3 is --OH and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
87 words
A compound selected from the group consisting of 3-quinoline-carboxamides of the formula ##STR5## wherein R is in 6 or 7-position and is selected from the group consisting of hydrogen, halogen, and alkoxy of 1 to 6 carbon atoms R 1 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, phenyl and benzyl, R 2 is --NHR 4 , R 4 is alkyl of 2 to 6 carbon atoms, and R 3 is --OH and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of 4-hydroxy-N-n-propyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 4
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of 4-hydroxy-N-n-butyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 5
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of 4-hydroxy-N-n-hexyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 6
Dependent Claim
20 words
An anxiolytic composition comprising an anxiolytically effective amount of at least one compound of claim 1 and a pharmaceutical carrier.
Claim 7
Dependent Claim
24 words
A composition of claim 5 wherein the compound is selected from the group consisting of 4-hydroxy-N-n-propyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 8
Dependent Claim
24 words
A composition of claim 5 wherein the compound is selected from the group consisting of 4-hydroxy-N-n-butyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 9
Dependent Claim
24 words
A composition of claim 5 wherein the compound is selected from the group consisting of 4-hydroxy-N-n-hexyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 10
Independent Claim
209 words
A method of inducing anxiolytic activity in warm-blooded animals comprising administering to warm-blooded animals an anxiolytically effective amount of at least one compound of 3-quinoline-carboxamides of the formula ##STR6## wherein R is in 6- or 7-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 atoms, --CF 3 , --SCF 3 and CH 3 S--, R 1 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, phenyl and benzyl, R 2 is --NHR 4 , R 4 is selected from the group consisting of alkyl of 2 to 6 carbon atoms, substituted aryl of 6 to 10 carbon atoms and substituted pyridyl, said substituents being at least one member of the group consisting of halogen, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethylthio, --OH, --NH 2 and alkylamino and dialkylamino of 1 to 6 alkyl carbon atoms with the proviso that when R 4 is a mono substituted aryl or heterocycle, the substituent is different from R of the quinoline when it is a halogen and R 3 is selected from the group consisting of hydrogen and --OH and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 11
Independent Claim
209 words
A method of inducing anxiolytic activity in warm-blooded animals comprising administering to warm-blooded animals an anxiolytically effective amount of at least one compound of 3-quinoline-carboxamides of the formula ##STR6## wherein R is in 6- or 7-position and is selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, alkoxy of 1 to 6 atoms, --CF 3 , --SCF 3 and CH 3 S--, R 1 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, phenyl and benzyl, R 2 is --NHR 4 , R 4 is selected from the group consisting of alkyl of 2 to 6 carbon atoms, substituted aryl of 6 to 10 carbon atoms and substituted pyridyl, said substituents being at least one member of the group consisting of halogen, methyl, methoxy, methylthio, trifluoromethyl, trifluoromethylthio, --OH, --NH 2 and alkylamino and dialkylamino of 1 to 6 alkyl carbon atoms with the proviso that when R 4 is a mono substituted aryl or heterocycle, the substituent is different from R of the quinoline when it is a halogen and R 3 is selected from the group consisting of hydrogen and --OH and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 12
Dependent Claim
14 words
The method of claim 9 wherein in the compound, R 4 is substituted aryl.
Claim 13
Dependent Claim
24 words
A method of claim 9 wherein the compound is selected from the group consisting of 4-hydroxy-N-(4-methoxyphenyl)-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 14
Dependent Claim
24 words
A method of claim 9 wherein the compound is selected from the group consisting of 4-hydroxy-N-(4-hydroxyphenyl)-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 15
Dependent Claim
24 words
A method of claim 9 wherein the compound is selected from the group consisting of 4-hydroxy-N-(3-methoxyphenyl)-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 16
Dependent Claim
24 words
A method of claim 9 wherein the compound is selected from the group consisting of 4-hydroxy-N-n-propyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 17
Dependent Claim
24 words
A method of claim 9 wherein the compound is selected from the group consisting of 4-hydroxy-N-n-butyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 18
Dependent Claim
24 words
A method of claim 9 wherein the compound is selected from the group consisting of 4-hydroxy-N-n-hexyl-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
References Cited (Backward Citations)
US2504896A
Cited
US2504875A
Cited
US2614121A
Cited
US2798070A
Cited
US3960868A
Cited
US3992540A
Cited
US4107310A
Cited
US4299831A
Cited
EP0012369A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-05-22 | 1987-11-21 | 1988-05-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-22 | 1991-11-21 | 1992-05-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-22 | 1995-11-21 | 1996-05-22 | $7700.00 | Window Closed / Lapsed |