US4232038A
Expired / Lapsed
US
⏱️ 0.0 years remaining
5-Alkylsulfinylbenzoyl- and 5-alkylsulfonylbenzoyl-1,2-dihydro-3H-pyrrolo[1,]pyrrole-1-carboxylic acids
Assignee: Syntex USA LLC
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Filing: 1979-08-31
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Granted: 1980-11-04
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Expires: 1999-08-31
Abstract
Abstract Novel 5-alkylsulfinylbenzoyl- and 5-alkylsulfonylbenzoyl,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid compounds represented by the formula <IMAGE> and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein n is 1 or 2, R is hydrogen or a lower alkyl group containing from 1-4 carbon atoms and R1 is a lower alkyl group having from 1-4 carbon atoms at the ortho, meta or para postions of the benzoyl group and process for the production of such compounds. These compounds are useful as anti-inflammatory, analgesic and antipyretic agents and as smooth muscle relaxants.
Inventors
- 👤 Arthur F. Kluge
- 👤 Joseph M. Muchowski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 06:01
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/33; C07D207/335; C07C; C07C323/00; C07D207/337; C07D207/34; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
76 words
A compound selected from the group of those represented by the formula: ##STR14## and the pharmaceutically acceptable, non-toxic alkyl esters having from one to 12 carbon atoms and salts thereof, wherein n is 1 or 2, R represents hydrogen or a lower alkyl group having from 1 to 4 carbon atoms and R 1 represents lower alkyl group having from 1 to 4 carbon atoms at the ortho, meta or para positions of the aroyl group.
Claim 2
Dependent Claim
76 words
A compound selected from the group of those represented by the formula: ##STR14## and the pharmaceutically acceptable, non-toxic alkyl esters having from one to 12 carbon atoms and salts thereof, wherein n is 1 or 2, R represents hydrogen or a lower alkyl group having from 1 to 4 carbon atoms and R 1 represents lower alkyl group having from 1 to 4 carbon atoms at the ortho, meta or para positions of the aroyl group.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein R is hydrogen.
Claim 4
Dependent Claim
10 words
A compound of claim 2 wherein R 1 is methyl.
Claim 5
Dependent Claim
23 words
A compound of claim 3 wherein R 1 is methyl, n is 1 and the R 1 S(O) substituent is at the p-position.
Claim 6
Dependent Claim
10 words
A carboxylic acid compound of claim 4, namely 5-(p-methylsulfinyl)benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid.
Claim 7
Dependent Claim
12 words
A methyl ester of the compound of claim 4, namely methyl 5-(p-methylsulfinyl)benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 8
Dependent Claim
16 words
A carboxylic acid of the compound of claim 3 wherein n is 2, namely isopropyl 5-(p-methylsulfonyl)-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 9
Dependent Claim
20 words
A compound of claim 1 wherein the R 1 S(O) n substituent is at the para-position of the phenyl ring.
Claim 10
Dependent Claim
10 words
A compound of claim 8 wherein R 1 is methyl.
Claim 11
Dependent Claim
9 words
The compound of claim 9 wherein R is methyl.
Claim 12
Dependent Claim
13 words
A carboxylic acid of claim 10 wherein n is 1, namely 5-(p-methylsulfinyl)benzoyl-6-methyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid.
Claim 13
Dependent Claim
15 words
A carboxylic acid of the compound of claim 10 wherein n is 2, namely methyl-5-(p-methylsulfonyl)-benzoyl-6-methyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 14
Dependent Claim
29 words
A composition for treating inflammation, pain or pyrexia in mammals consisting essentially of a pharmaceutically acceptable non-toxic excipient and a therapeutically effective amount of a compound of claim 1.
Claim 15
Dependent Claim
28 words
A method of treating inflammation, pain or pyrexia in mammals which comprises administering to a mammal suffering therefrom a therapeutically effective amount of a compound of claim 1.
Claim 16
Dependent Claim
32 words
A composition for administration to a pregnant mammal to delay onset of parturition consisting essentially of a pharmaceutically acceptable non-toxic excipient and a therapeutically effective amount of a compound of claim 1.
Claim 17
Dependent Claim
24 words
A method comprising administering to a pregnant mammal to delay the onset of parturition a therapeutically effective amount of a compound of claim 1.
Claim 18
Dependent Claim
21 words
The method of claim 16 wherein said pregnant mammal is a woman who is not suffering from inflammation, pyrexia, or pain.
Claim 19
Dependent Claim
33 words
The method of claim 17 wherein said pregnant woman has had a previous spontaneous abortion, miscarriage or premature delivery, which occurred prior to the time for normal parturition at or about full term.
Claim 20
Dependent Claim
72 words
The method of claim 16 wherein said pregnant mammal is a woman who is not suffering from inflammation, pyrexia or nonparturition-causing pain but who is experiencing uterine muscle contractions, said compound being administered in a therapeutically effective amount adapted to reduce the intensity or duration of the uterine muscle contractions or stop the uterine muscle contractions altogether, whereby termination of the pregnancy is postponed from the time it otherwise would have happened.
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) | 1983-11-04 | 1984-05-05 | 1984-11-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-04 | 1988-05-05 | 1988-11-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-04 | 1992-05-05 | 1992-11-04 | $7700.00 | Window Closed / Lapsed |