US4677112A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1,2,3,4-tetrahydro-2-oxo-8-quinolineacetic and -propanoic acids and derivatives as cognition activators
Assignee: Warner Lambert Co LLC
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Filing: 1985-11-22
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Granted: 1987-06-30
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Expires: 2005-11-22
Abstract
Abstract Benzobicyclic lactam acids having a fused aromatic carbocyclic and a saturated lactam ring of five- or six-members, their salts, esters, and amides, are useful in the treatment of senility and for reversing amnesia. Pharmaceutical compositions including these compounds, a method of preparing the compounds, and a method of treating senility and reversing amnesia area also disclosed.
Inventors
- 👤 Donald E. Butler
- 👤 Michael R. Pavia
- 👤 Fred M. Hershenson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:35
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/227; C07C; C07C205/00; C07C205/49; C07C205/56; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/32; C07D209/34; C07D209/38; C07D401/00; C07D401/02; C07D401/12; C07D405/00; C07D405/02; C07D405/04; C07D455/00; C07D455/03; C07D455/04; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
201 words
A compound having the formula ##STR9## wherein y is zero or one; R is hydrogen, halogen, hydroxyl, --OR 1 where R 1 is alkyl of from one to six carbon atoms, phenyl, or phenylmethyl, --NR 2 R 3 where R 2 and R 3 are independently alkyl of from one to six carbon atoms; R 4 is selected from --OH and the pharmaceutically acceptable metal, ammonium, and amine acid addition salts thereof, --OR 1 where R 1 is as previously defined, ##STR10## --NHCH 2 CH 2 N[CH(CH 3 ) 2 ] 2 , and --NR 6 R 7 where R 6 and R 7 are independently hydrogen or alkyl of from one to six carbon atoms; and R 5 is hydrogen or ##STR11## where R 8 and R 9 are independently hydrogen, halogen, hydroxyl, --OR 1 where R 1 is as previously defined, --NR 10 R 11 where R 10 and R 11 are independently hydrogen, alkyl of from one to six carbon atoms, or where R 8 and R 9 are attached to adjacent carbon atoms, taken together are --OCH 2 O--; with the proviso that when R 5 is hydrogen, R 4 may not be H or lower alkyl.
Claim 2
Dependent Claim
201 words
A compound having the formula ##STR9## wherein y is zero or one; R is hydrogen, halogen, hydroxyl, --OR 1 where R 1 is alkyl of from one to six carbon atoms, phenyl, or phenylmethyl, --NR 2 R 3 where R 2 and R 3 are independently alkyl of from one to six carbon atoms; R 4 is selected from --OH and the pharmaceutically acceptable metal, ammonium, and amine acid addition salts thereof, --OR 1 where R 1 is as previously defined, ##STR10## --NHCH 2 CH 2 N[CH(CH 3 ) 2 ] 2 , and --NR 6 R 7 where R 6 and R 7 are independently hydrogen or alkyl of from one to six carbon atoms; and R 5 is hydrogen or ##STR11## where R 8 and R 9 are independently hydrogen, halogen, hydroxyl, --OR 1 where R 1 is as previously defined, --NR 10 R 11 where R 10 and R 11 are independently hydrogen, alkyl of from one to six carbon atoms, or where R 8 and R 9 are attached to adjacent carbon atoms, taken together are --OCH 2 O--; with the proviso that when R 5 is hydrogen, R 4 may not be H or lower alkyl.
Claim 3
Dependent Claim
54 words
A compound in accordance with claim 1 wherein R is selected from hydrogen; fluorine; chlorine; hydroxy; --OR 1 wherein R 1 is alkyl of from one to six carbon atoms, phenyl, or phenylmethyl; or --NR 2 R 3 where R 2 and R 3 are independently alkyl of from one to six carbon atoms.
Claim 4
Dependent Claim
18 words
A compound in accordance with claim 1 wherein R 4 is --OH, and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
28 words
A compound in accordance with claim 1 wherein R 4 is --OR 1 wherein R 1 is alkyl of from one to six carbon atoms, phenyl, or phenylmethyl.
Claim 6
Dependent Claim
46 words
A compound in accordance with claim 1 where R 4 is ##STR12## --NHCH 2 CH 2 N[CH(CH 3 ) 2 ] 2 ; or --NR 6 R 7 where R 6 and R 7 are independently hydrogen or alkyl of from one to six carbon atoms.
Claim 7
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 1-[4-(dimethylamino)benzoyl]-1,2,3,4-tertrahydro-2-oxo-8-quinolineactetic acid and the pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 1-[4-methoxy-3-(phenylmethoxy)benzoyl]-1,2,3,4-tetrahydro-2-oxo-8-quinolinepropanoic acid and the pharmaceutically acceptable salts thereof.
Claim 9
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 1-(1,3-benzodioxol-5-ylcarbonyl)-1,2,3,4-tetrahydro-2-oxo-8-quinolinepropanoic acid and the pharmaceutically acceptable salts thereof.
Claim 10
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 1-(4-methoxybenzoyl)-1,2,3,4-tetrahydro-2-oxo-8-quinolineacetic acid and the pharmaceutically acceptable salts thereof.
Claim 11
Dependent Claim
14 words
A compound in accordance with claim 1 having the name 1,2,3,4-tetrahydro-2-oxo-8-quinolineacetic acid phenylmethyl ester.
Claim 12
Dependent Claim
14 words
A compound in accordance with claim 1 having the name 1,2,3,4-tetrahydro-2-oxo-8-quinolinepropanoic acid phenylmethyl ester.
Claim 13
Dependent Claim
14 words
A compound in accordance with claim 1 having the name 1-(2-fluorobenzoyl)-6-methoxy-1,2,3,4-tetrahydro-2-oxo-8-quinolineacetic acid phenyl ester.
Claim 14
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 1-(2-methoxybenzoyl)-1,2,3,4-tetrahydro-2-oxo-6-phenoxy-8-quinolinepropanoic acid and the pharmaceutically acceptable salts thereof.
Claim 15
Dependent Claim
14 words
A compound in accordance with claim 1 having the name 1-(2-methoxybenzoyl)-1,2,3,4-tetrahydro-2-oxo-6-phenoxy-8-quinolinepropanoic acid phenylmethyl ester.
Claim 16
Dependent Claim
34 words
A pharmaceutical composition useful for reversing the effects of electroconvulsive shock-induced amnesia in a mammal comprising an effective amount of a compound in accordance with claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 17
Dependent Claim
27 words
A method of reversing electroconvulsive shock-induced amnesia in mammals comprising administering to said mammal an effective amount of of a pharmaceutical composition in accordance with claim 15.
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) | 1990-06-29 | 1990-12-29 | 1991-06-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-06-29 | 1994-12-29 | 1995-06-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-06-29 | 1998-12-29 | 1999-06-30 | $7700.00 | Window Closed / Lapsed |