US4450166A
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N-(4,5-Dihydro-thiazol-2-yl)-3-quinoline-carboxamides having anxiolytic activity
Assignee: Sanofi Aventis France
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Filing: 1982-06-09
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Granted: 1984-05-22
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Expires: 2002-06-09
Abstract
Abstract Novel N-(4,5-dihydro-thiazol-2-yl)-4-hydroxy-3-quinoline-carboxamides of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R 1 is selected from the group consisting of hydrogen, halogen, linear alkyl of 1 to 4 carbon atoms, branched alkyl of 3 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, CF 3 --, CF 3 O--, CF 3 S-- and CH 3 S-- in the 6- or 7-position and their non-toxic, pharmaceutically acceptable acid addition salts having a strong anxiolytic activity and a remarkable affinity for benzodiapines receptors and their preparation.
Inventors
- 👤 Francois Clemence
- 👤 Peter F. Hunt
- 👤 Odile Le Martret
- 👤 Daniel Humbert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 20:25
CPC Classifications
C; C07; C07D; C07D417/00; C07D417/02; C07D417/12; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
92 words
A compound selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-4-hydroxy-3-quinoline-carboxamides of the formula ##STR4## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R 1 is selected from the group consisting of hydrogen, halogen, linear alkyl of 1 to 4 carbon atoms, branched alkyl of 3 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, CF 3 --, CF 3 O--, CF 3 S-- and CH 3 S-- in the 6- or 7-position and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
92 words
A compound selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-4-hydroxy-3-quinoline-carboxamides of the formula ##STR4## wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 4 carbon atoms and R 1 is selected from the group consisting of hydrogen, halogen, linear alkyl of 1 to 4 carbon atoms, branched alkyl of 3 to 5 carbon atoms, alkoxy of 1 to 4 carbon atoms, CF 3 --, CF 3 O--, CF 3 S-- and CH 3 S-- in the 6- or 7-position and their non-toxic, pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
11 words
A compound of claim 1 wherein R is hydrogen or methyl.
Claim 4
Dependent Claim
14 words
A compound of claim 1 or 2 wherein R 1 is chlorine or methoxy.
Claim 5
Dependent Claim
30 words
A compound of claim 1 or 2 wherein R 1 is the 6-position and is selected from the group consisting of fluorine, methyl, ethyl, isopropyl, methylthio and CF 3 --.
Claim 6
Dependent Claim
9 words
A compound of claim 2 wherein R is hydrogen.
Claim 7
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 8
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-6-ethyl-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 9
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-6-chloro-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 10
Dependent Claim
20 words
A compound of claim 1 selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-2-methyl-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 11
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 12
Dependent Claim
11 words
A composition of claim 10 wherein R is hydrogen or methyl.
Claim 13
Dependent Claim
12 words
A composition of claim 10 wherein R 1 is chlorine or methoxy.
Claim 14
Dependent Claim
29 words
A composition of claim 10 wherein R 1 is in the 6-position and is selected from the group consisting of fluorine, methyl, ethyl, isopropyl, methylthio and CF 3 --.
Claim 15
Dependent Claim
9 words
A composition of claim 10 wherein R is hydrogen.
Claim 16
Dependent Claim
25 words
A composition of claim 10 wherein the active compound is selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 17
Dependent Claim
25 words
A composition of claim 10 wherein the active compound is selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-6-ethyl-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 18
Dependent Claim
25 words
A composition of claim 10 wherein the active compound is selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-6-chloro-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 19
Dependent Claim
25 words
A composition of claim 10 wherein the active compound is selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-2-methyl-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 20
Dependent Claim
26 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 claim 1.
Claim 21
Dependent Claim
11 words
A method of claim 19 wherein R is hydrogen or methyl.
Claim 22
Dependent Claim
12 words
A method of claim 19 wherein R 1 is chlorine or methoxy.
Claim 23
Dependent Claim
29 words
A method of claim 19 wherein R 1 is in the 6-position and is selected from the group consisting of fluorine, methyl, ethyl, isopropyl, methylthio and CF 3 --.
Claim 24
Dependent Claim
9 words
A method of claim 19 wherein R is hydrogen.
Claim 25
Dependent Claim
25 words
A method of claim 19 wherein the active compound is selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 26
Dependent Claim
25 words
A method of claim 19 wherein the active compound is selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-6-ethyl-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 27
Dependent Claim
25 words
A method of claim 19 wherein the active compound is selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-6-chloro-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 28
Dependent Claim
25 words
A method of claim 19 wherein the active compound is selected from the group consisting of N-(4,5-dihydro-thiazol-2-yl)-2-methyl-4-hydroxy-3-quinoline-carboxamide and its non-toxic, pharmaceutically acceptable acid addition salts.
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) | 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 |