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US4960786A
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Excitatory amino acid antagonists
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1989-04-24
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Granted: 1990-10-02
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Expires: 2009-04-24
Abstract
Abstract The present invention is directed to the discovery of a new use for a group of known 2-carboxylic indole derivatives. The compounds are excitatory amino acid antagonists.
Inventors
- 👤 Francesco G. Salituro
- 👤 Boyd L. Harrison
- 👤 Bruce M. Baron
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 05:14
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/40; A61K31/403; A61K31/404; A61K31/405; A61P; A61P25/00; A61P25/04; A61P25/08; A61P25/20; A61P25/28; A61P9/00; A61P9/10
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
182 words
A method for antagonizing the effects of excitatory amino acids upon the NMDA receptor complex comprising administering to a patient in need thereof, an antagonistic amount of a compound of the formula: ##STR2## in which X is represented by a C 1-4 alkylene, Z is represented by H, C 1-4 alkyl, phenyl, substituted phenyl, or an alkylphenyl substituent in which the phenyl ring may be optionally substitued; R is represented by a substituent selected from the group consisting of hydrogen, halogen, C 1-4 alkyl, C 1-4 alkoxy, CF 3 , OCF 3 , OH, NO 2 , and CN; R 1 and R 2 are each independently represented by --OH, --OR 3 in which R 3 is represented by a C 1-4 alkyl, phenyl, substituted phenyl or an alkylphenyl substituent in which the phenyl ring may be optionally substituted, NR 4 R 5 in which R 4 and R 5 are each independently represented by hydrogen or a C 1-4 alkyl, or OCH 2 OR 3 in which R 3 is as defined above, and a pharmaceutically acceptable basic addition salt thereof.
Claim 2
Independent Claim
182 words
A method for antagonizing the effects of excitatory amino acids upon the NMDA receptor complex comprising administering to a patient in need thereof, an antagonistic amount of a compound of the formula: ##STR2## in which X is represented by a C 1-4 alkylene, Z is represented by H, C 1-4 alkyl, phenyl, substituted phenyl, or an alkylphenyl substituent in which the phenyl ring may be optionally substitued; R is represented by a substituent selected from the group consisting of hydrogen, halogen, C 1-4 alkyl, C 1-4 alkoxy, CF 3 , OCF 3 , OH, NO 2 , and CN; R 1 and R 2 are each independently represented by --OH, --OR 3 in which R 3 is represented by a C 1-4 alkyl, phenyl, substituted phenyl or an alkylphenyl substituent in which the phenyl ring may be optionally substituted, NR 4 R 5 in which R 4 and R 5 are each independently represented by hydrogen or a C 1-4 alkyl, or OCH 2 OR 3 in which R 3 is as defined above, and a pharmaceutically acceptable basic addition salt thereof.
Claim 3
Dependent Claim
14 words
A method according to claim 1 wherein X is represented by a ethylene group.
Claim 4
Dependent Claim
16 words
A method according to claim 1 wherein R 1 and R 2 are represented by OH.
Claim 5
Dependent Claim
27 words
A method according to claim 1 in which R is represented by a monosubstitution occurring at position 6, or a disubstitution occurring at positions 4 and 6.
Claim 6
Dependent Claim
25 words
A method for the treatment of epilepsy comprising administering to a patient in need therof an anti-epileptic amount of a compound according to claim 1.
Claim 7
Dependent Claim
26 words
A method for the treatment of neurodegenerative diseases comprising administering to a patient in need thereof an effective amount of a compound according to claim 1.
Claim 8
Dependent Claim
27 words
A method for preventing ischemic/hypoxic/hypoglycemic damage to cerebral tissue comprising administering to a patient in need thereof an effective amount of a compound according to claim 1.
Claim 9
Dependent Claim
26 words
A method for the treatment of anxiety comprising administering to a patient in need thereof an anxiolytically effective amount of a compound according to claim 1.
Claim 10
Dependent Claim
25 words
A method for producing an analgesic effect comprising administering to a patient in need thereof an analgesic amount of a compound according to claim 1.
Claim 11
Dependent Claim
12 words
A method according to claim 4 wherein X is represented by ethylene.
Claim 12
Dependent Claim
13 words
A method according to claim 10 wherein said R is a 4,6-dichloro substituent.
Claim 13
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-6-methoxyindol-3-yl)propionic acid.
Claim 14
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-6-chloroindol-3-yl)propionic acid.
Claim 15
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-4,6-dichloroindol-3-yl)propionic acid.
Claim 16
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-6-trifluoromethoxyindol-3-yl)propionic acid.
Claim 17
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-4-trifluoromethylindol-3-yl)propionic acid.
Claim 18
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-6-trifluoromethylindol-3-yl)propionic acid.
Claim 19
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-4-fluoroindol-3-yl)propionic acid.
Claim 20
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-4-nitroindol-3-yl)propionic acid.
Claim 21
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-6-nitroindol-3-yl)propionic acid.
Claim 22
Dependent Claim
13 words
A method according to claim 1 wherein said compound is ethyl 3-(2-carboxyethyl-4,6-dichloroindol-3-yl) propionate.
Claim 23
Dependent Claim
13 words
A method according to claim 1 wherein said compound is benzyl 3-(2-carboxybenzyl-4,6-dichloroindol-3-yl) propionate.
Claim 24
Dependent Claim
11 words
A method according to claim 1 wherein said compound is 3-(2-Carboxamide-4,6-dichloroindol-3-yl)propionamide.
Claim 25
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 2-(2-Carboxy-6-chloroindol-3-yl)acetic acid.
Claim 26
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 4-(2-Carboxy-6-chloroindol-3-yl)butyric acid.
Claim 27
Dependent Claim
12 words
A method according to claim 1 wherein said compound is 5-(2-Carboxy-6-chloroindol-3-yl)pentanoic acid.
Claim 28
Dependent Claim
11 words
A method according to claim 1 wherein said compound is 3-(2-Carboxy-4,6-dichloro-1-methylindol-3-yl).
Claim 29
Dependent Claim
171 words
A pharmaceutical composition comprising an antagonistically effective amount of a compound of the formula: ##STR3## in which X is represented by a C 1-4 alkylene, Z is represented by H, C 1-4 alkyl, phenyl, substituted phenyl, or an alkylphenyl substituent in which the phenyl ring may be optionally substituted; R is represented by a substituent selected from the group consisting of hydrogen, halogen, C 1-4 alkyl, C 1-4 alkoxy, CF 3 , OCF 3 , OH, NO 2 , and CN; R 1 and R 2 are each independently represented by --OH, --OR 3 in which R 3 is represented by a C 1-4 alkyl, phenyl, substituted phenyl or an alkylphenyl substituent in which the phenyl ring may be optionally substituted, --NR 4 R 5 in which R 4 and R 5 are each independently represented by hydrogen or a C 1-4 alkyl, or --OCH 2 OR 3 in which R 3 is as defined above, and a pharmaceutically acceptable basic addition salt thereof; in admixture with a pharmaceutically acceptable carrier.
Claim 30
Dependent Claim
171 words
A pharmaceutical composition comprising an antagonistically effective amount of a compound of the formula: ##STR3## in which X is represented by a C 1-4 alkylene, Z is represented by H, C 1-4 alkyl, phenyl, substituted phenyl, or an alkylphenyl substituent in which the phenyl ring may be optionally substituted; R is represented by a substituent selected from the group consisting of hydrogen, halogen, C 1-4 alkyl, C 1-4 alkoxy, CF 3 , OCF 3 , OH, NO 2 , and CN; R 1 and R 2 are each independently represented by --OH, --OR 3 in which R 3 is represented by a C 1-4 alkyl, phenyl, substituted phenyl or an alkylphenyl substituent in which the phenyl ring may be optionally substituted, --NR 4 R 5 in which R 4 and R 5 are each independently represented by hydrogen or a C 1-4 alkyl, or --OCH 2 OR 3 in which R 3 is as defined above, and a pharmaceutically acceptable basic addition salt thereof; in admixture with a pharmaceutically acceptable carrier.
Claim 31
Dependent Claim
14 words
A pharmaceutical composition according to claim 28 wherein X is represented by an ethylene.
Claim 32
Dependent Claim
17 words
A pharmaceutical composition according to claim 28 wherein R 1 and R 2 are represented by OH.
Claim 33
Dependent Claim
13 words
A pharmaceutical composition according to claim 29 wherein said R is a 4,6-dichloro-substituent.
Claim 34
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-6-methoxyindol-3yl)propionic acid.
Claim 35
Dependent Claim
14 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-6-chloroindol-3 yl)propionic acid.
Claim 36
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-4,6-dichloroindol-3-yl)propionic acid.
Claim 37
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-6-trifluoromethoxyindol-3-yl)propionic acid.
Claim 38
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-4-trifluoromethylindol-3-yl)propionic acid.
Claim 39
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-6-trifluoromethylindol-3-yl)propionic acid.
Claim 40
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-4-fluoroindol-3-yl)propionic acid.
Claim 41
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-4-nitroindol-3-yl)propionic acid.
Claim 42
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-6-nitroindol-3-yl)propionic acid.
Claim 43
Dependent Claim
14 words
A pharmaceutical composition according to claim 28 wherein said compound is ethyl 3-(2-carboxyethyl-4,6-dichloroindol-3-yl) propionate.
Claim 44
Dependent Claim
14 words
A pharmaceutical composition according to claim 28 wherein said compound is benzyl 3-(2-carboxybenzyl-4,6-dichloroindol-3-yl) propionate.
Claim 45
Dependent Claim
12 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxamide-4,6-dichloroindol-3-yl)propionamide.
Claim 46
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 2-(2-Carboxy-6-chloroindol-3-yl)acetic acid.
Claim 47
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 4-(2-Carboxy-6-chloroindol-3-yl)butyric acid.
Claim 48
Dependent Claim
13 words
A pharmaceutical composition according to claim 28 wherein said compound is 5-(2-Carboxy-6-chloroindol-3-yl)pentanoic acid.
Claim 49
Dependent Claim
12 words
A pharmaceutical composition according to claim 28 wherein said compound is 3-(2-Carboxy-4,6-dichloro-1-methylindol-3-yl).
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-10-01 | 1994-04-02 | 1994-10-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-10-01 | 1998-04-02 | 1998-10-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-10-01 | 2002-04-02 | 2002-10-02 | $7700.00 | Window Closed / Lapsed |