US4730004A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Analgesic and anti-inflammatory 1-acyl-2-oxindole-3-carboxamides
Assignee: Pfizer Inc
•
Filing: 1987-02-02
•
Granted: 1988-03-08
•
Expires: 2007-02-02
Abstract
Abstract Certain new 2-oxindole-3-carboxamide compounds having an acyl substituent at the 1-position are inhibitors of the cyclooxygenase (CO) and lipoxygenase (LO) enzymes, and are useful as analgesic and anti-inflammatory agents in mammalian subjects. In particular, the compounds of the invention are useful for acute administration for ameliorating or eliminating pain in human subjects recovering from surgery or trauma, and also for chronic administration for alleviating the symptoms of chronic diseases, such as rheumatoid arthritis and osteoarthritis, in human subjects.
Inventors
- 👤 Saul B. Kadin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 18:50
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/12; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/42; C07D409/00; C07D409/02; C07D409/12; C07D417/00; C07D417/02; C07D417/12
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
100 words
A 1-acyl-2-oxindole-3-carboxamide compound of formula ##STR10## and the pharmaceutically-acceptable base salts thereof; wherein X and Y are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl and alkyl having 1 to 4 carbons; R 1 is selected from the group consisting of alkyl having from 1 to 6 carbons, cycloalkyl having from 3 to 7 carbons and groups of the formula ##STR11## wherein R 3 and R 4 are each selected from the group consisting of hydrogen, fluoro, chloro, alkyl having 1 to 4 carbons and trifluoromethyl; and R 2 is alkyl having 1 to 6 carbons.
Claim 2
Dependent Claim
100 words
A 1-acyl-2-oxindole-3-carboxamide compound of formula ##STR10## and the pharmaceutically-acceptable base salts thereof; wherein X and Y are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl and alkyl having 1 to 4 carbons; R 1 is selected from the group consisting of alkyl having from 1 to 6 carbons, cycloalkyl having from 3 to 7 carbons and groups of the formula ##STR11## wherein R 3 and R 4 are each selected from the group consisting of hydrogen, fluoro, chloro, alkyl having 1 to 4 carbons and trifluoromethyl; and R 2 is alkyl having 1 to 6 carbons.
Claim 3
Dependent Claim
12 words
A compound according to claim 1, wherein R 1 is said ##STR12##
Claim 4
Dependent Claim
11 words
A compound according to claim 2, wherein R 2 is methyl.
Claim 5
Dependent Claim
13 words
A compound according to claim 3, wherein X and Y are each hydrogen.
Claim 6
Dependent Claim
11 words
The compound according to claim 4, wherein R 1 is phenyl.
Claim 7
Dependent Claim
14 words
A compound according to claim 3, wherein X is 5-chloro and Y is hydrogen.
Claim 8
Dependent Claim
11 words
The compound according to claim 6, wherein R 1 is 4-fluorophenyl.
Claim 9
Dependent Claim
11 words
The compound according to claim 6, wherein R 1 is 2,4-dichlorophenyl.
Claim 10
Dependent Claim
14 words
A compound according to claim 3, wherein X is 5-chloro and Y is 6-fluoro.
Claim 11
Dependent Claim
11 words
The compound according to claim 9, wherein R 1 is phenyl.
Claim 12
Dependent Claim
11 words
The compound according to claim 9, wherein R 1 is 4-chlorophenyl.
Claim 13
Independent Claim
129 words
A method of eliciting an analgesic response in a mammalian subject, which comprises administering to said subject an analgesic response eliciting amount of a 1-acyl-2-oxindole-3-carboxamide compound of the formula ##STR13## or a pharmaceutically-acceptable base salt thereof; wherein X and Y are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl and alkyl having 1 to 4 carbons; R 1 is selected from the group consisting of alkyl having from 1 to 6 carbons, cycloalkyl having from 3 to 7 carbons groups of the formula ##STR14## wherein R 3 and R 4 are each selected from the group consisting of hydrogen, fluoro, chloro, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons and trifluoromethyl; and R 2 is alkyl having 1 to 6 carbons.
Claim 14
Independent Claim
129 words
A method of eliciting an analgesic response in a mammalian subject, which comprises administering to said subject an analgesic response eliciting amount of a 1-acyl-2-oxindole-3-carboxamide compound of the formula ##STR13## or a pharmaceutically-acceptable base salt thereof; wherein X and Y are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl and alkyl having 1 to 4 carbons; R 1 is selected from the group consisting of alkyl having from 1 to 6 carbons, cycloalkyl having from 3 to 7 carbons groups of the formula ##STR14## wherein R 3 and R 4 are each selected from the group consisting of hydrogen, fluoro, chloro, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons and trifluoromethyl; and R 2 is alkyl having 1 to 6 carbons.
Claim 15
Dependent Claim
12 words
The method according to claim 12, wherein R 1 is said ##STR15##
Claim 16
Dependent Claim
11 words
The method according to claim 13, wherein R 2 is methyl.
Claim 17
Dependent Claim
13 words
The method according to claim 14, wherein X and Y are each hydrogen.
Claim 18
Dependent Claim
11 words
The method according to claim 15, wherein R 1 is phenyl.
Claim 19
Dependent Claim
14 words
The method according to claim 14, wherein X is 5-chloro and Y is hydrogen.
Claim 20
Dependent Claim
11 words
The method according to claim 17, wherein R 1 is 4-fluorophenyl.
Claim 21
Dependent Claim
11 words
The method according to claim 17, wherein R 1 is 2,4-dichlorophenyl.
Claim 22
Dependent Claim
14 words
The method according to claim 14, wherein X is 5-chloro and Y is 6-fluoro.
Claim 23
Dependent Claim
11 words
The method according to claim 20, wherein R 1 is phenyl.
Claim 24
Dependent Claim
11 words
The method according to claim 20, wherein R 1 is 4-chlorophenyl.
Claim 25
Independent Claim
131 words
A method of treating an inflammatory disease in a mammalian subject, which comprises administering to said mammalian subject an inflammatory disease treating amount of a 1-acyl-2-oxindole-3-carboxamide compound of the formula ##STR16## or a pharmaceutically-acceptable base salt thereof; wherein X and Y are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl and alkyl having 1 to 4 carbons; R 1 is selected from the group consisting of alkyl having from 1 to 6 carbons, cycloalkyl having from 3 to 7 carbons, and groups of the formula ##STR17## wherein R 3 and R 4 are each selected from the group consisting of hydrogen, fluoro, chloro, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons and trifluoromethyl; and R 2 is alkyl having 1 to 6 carbons.
Claim 26
Independent Claim
131 words
A method of treating an inflammatory disease in a mammalian subject, which comprises administering to said mammalian subject an inflammatory disease treating amount of a 1-acyl-2-oxindole-3-carboxamide compound of the formula ##STR16## or a pharmaceutically-acceptable base salt thereof; wherein X and Y are each selected from the group consisting of hydrogen, fluoro, chloro, bromo, trifluoromethyl and alkyl having 1 to 4 carbons; R 1 is selected from the group consisting of alkyl having from 1 to 6 carbons, cycloalkyl having from 3 to 7 carbons, and groups of the formula ##STR17## wherein R 3 and R 4 are each selected from the group consisting of hydrogen, fluoro, chloro, alkyl having 1 to 4 carbons, alkoxy having 1 to 4 carbons and trifluoromethyl; and R 2 is alkyl having 1 to 6 carbons.
Claim 27
Dependent Claim
12 words
The method according to claim 23, wherein R 1 is said ##STR18##
Claim 28
Dependent Claim
11 words
The method according to claim 24, wherein R 2 is methyl.
Claim 29
Dependent Claim
13 words
The method according to claim 25, wherein X and Y are each hydrogen.
Claim 30
Dependent Claim
11 words
The method according to claim 26, wherein R 1 is phenyl.
Claim 31
Dependent Claim
14 words
The method according to claim 25, wherein X is 5-chloro and Y is hydrogen.
Claim 32
Dependent Claim
11 words
The method according to claim 28, wherein R 1 is 4-florophenyl.
Claim 33
Dependent Claim
11 words
The method according to claim 28, wherein R 1 is 2,4-dichlorophenyl.
Claim 34
Dependent Claim
14 words
The method according to claim 25, wherein X is 5-chloro and Y is 6-fluoro.
Claim 35
Dependent Claim
11 words
The method according to claim 31, wherein R 1 is phenyl.
Claim 36
Dependent Claim
11 words
The method according to claim 31, wherein R 1 is 4-chlorophenyl.
Claim 37
Dependent Claim
37 words
A pharmaceutical composition, which comprises a pharmaceutically-acceptable carrier and a 1-acyl-2-oxindole-3-carboxamide compound according to claim 1, and wherein the weight ratio of the pharmaceutically-acceptable carrier to the 1-acyl-2-oxindole-3-carboxamide compound is in the range from 1:4 to 4:1.
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) | 1991-03-08 | 1991-09-07 | 1992-03-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-03-08 | 1995-09-07 | 1996-03-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-03-08 | 1999-09-07 | 2000-03-08 | $7700.00 | Window Closed / Lapsed |