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US4344943A
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6-Chloro- or 6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]-pyrrole-1-carboxylic acids and derivatives thereof
Assignee: Syntex USA LLC
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Filing: 1980-06-09
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Granted: 1982-08-17
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Expires: 2000-06-09
Abstract
Abstract Novel 5-aroyl-6-chloro- or 6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-7-carboxylic acids represented by the formula <IMAGE> and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein Y is chloro or bromo and Ar is an optionally substituted phenyl, 2-furyl, or 2-thienyl ring or a 3-furyl, 3-thienyl, 2-pyrrolyl or 1-alkyl-2-pyrrolyl ring. These compounds are useful as anti-inflammatory, analgesic and antipyretic agents and as smooth muscle relaxants.
Inventors
- 👤 Joseph M. Muchowski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 16:44
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/30; C07D207/32; C07D207/33; C07D207/337; A; A61; A61P; A61P13/00; A61P13/02; A61P15/00; A61P25/00; A61P25/04; A61P29/00; C07D207/34; C07D487/00; C07D487/02; C07D487/04
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
114 words
A compound selected from the group of those represented by the formula ##STR11## and the pharmaceutically acceptable, non-toxic alkyl esters having from 1 to 12 carbon atoms and salts thereof, wherein Y is chloro or bromo and Ar has the formula ##STR12## in which X is sulfur or oxygen; L is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, Br, Cl, F, CN, CF 3 or S(O) n R 3 wherein R 3 is alkyl having 1 to 4 carbon atoms and n is 0, 1 or 2; M is hydrogen, methyl, Cl or Br; and Q is hydrogen or alkyl having 1 to 4 carbon atoms.
Claim 2
Dependent Claim
114 words
A compound selected from the group of those represented by the formula ##STR11## and the pharmaceutically acceptable, non-toxic alkyl esters having from 1 to 12 carbon atoms and salts thereof, wherein Y is chloro or bromo and Ar has the formula ##STR12## in which X is sulfur or oxygen; L is hydrogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, Br, Cl, F, CN, CF 3 or S(O) n R 3 wherein R 3 is alkyl having 1 to 4 carbon atoms and n is 0, 1 or 2; M is hydrogen, methyl, Cl or Br; and Q is hydrogen or alkyl having 1 to 4 carbon atoms.
Claim 3
Dependent Claim
14 words
A compound of claim 1 selected from the group in which Ar is ##STR13##
Claim 4
Dependent Claim
18 words
A compound of claim 2 wherein Y is chloro and L is methyl, methoxy, methylthio, chloro or fluoro.
Claim 5
Dependent Claim
34 words
A compound of claim 3 in which Y is chloro and L is p-methyl, namely 5-p-toluoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 6
Dependent Claim
12 words
The methyl ester of the compound of claim 4, namely methyl 5-toluoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 7
Dependent Claim
34 words
A compound of claim 3 in which Y is chloro and L is p-fluoro, namely 5-p-fluorobenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 8
Dependent Claim
12 words
The methyl ester of the compound of claim 6, namely methyl 5-p-fluorobenzyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 9
Dependent Claim
34 words
A compound of claim 3 in which Y is chloro and L is p-methylthio, namely 5-p-methylthiobenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 10
Dependent Claim
12 words
The methyl ester of the compound of claim 8, namely methyl 5-p-methylthiobenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 11
Dependent Claim
34 words
A compound of claim 3 in which Y is chloro and L is p-methoxy, namely 5-p-methoxybenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 12
Dependent Claim
12 words
The methyl ester of the compound of claim 10, namely methyl 5-p-methoxybenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 13
Dependent Claim
34 words
A compound of claim 3 in which Y is chloro and L is p-chloro, namely 5-p-chlorobenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic akyl esters having from one to twelve carbon atoms and salts thereof.
Claim 14
Dependent Claim
12 words
The methyl ester of the compound of claim 12, namely methyl 5-p-chlorobenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 15
Dependent Claim
34 words
A compound of claim 2 in which Y is chloro and L is hydrogen, namely 5-benzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 16
Dependent Claim
12 words
The methyl ester of the compound of claim 4, namely methyl 5-benzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 17
Dependent Claim
34 words
A compound of claim 2 in which Y is chloro, and L is p-methylsulfonyl, namely 5-p-methylsulfonylbenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 18
Dependent Claim
12 words
The methyl ester of the compound of claim 16, namely methyl 5-p-methylsulfonylbenzoyl-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 19
Dependent Claim
34 words
A compound of claim 3 in which Y is bromo and L is p-fluoro, namely 5-p-fluorobenzoyl-6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 20
Dependent Claim
12 words
The methyl ester of the compound of claim 6, namely methyl 5-p-fluorobenzoyl-6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 21
Dependent Claim
34 words
A compound of claim 2 in which Y is bromo and L is hydrogen, namely 5-benzoyl-6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 22
Dependent Claim
12 words
The methyl ester of the compound of claim 4, namely methyl 5-benzoyl-6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate.
Claim 23
Dependent Claim
14 words
A compound of claim 1 selected from the group in which Ar is ##STR14##
Claim 24
Dependent Claim
10 words
A compound of claim 22 in which X is oxygen.
Claim 25
Dependent Claim
10 words
A compound of claim 22 in which X is sulfur.
Claim 26
Dependent Claim
32 words
A compound of claim 24 wherein Y is chloro, and M is hydrogen, 5-(2-thenoyl)-6-chloro-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof.
Claim 27
Dependent Claim
14 words
A compound of claim 1 selected from the group in which Ar is ##STR15##
Claim 28
Dependent Claim
14 words
A compound of claim 1 selected from the group in which Ar is ##STR16##
Claim 29
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 30
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 31
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 32
Dependent Claim
25 words
A method which comprises administering to a pregnant mammal to delay the onset of parturition a pharmaceutically effective amount of a compound of claim 1.
Claim 33
Dependent Claim
21 words
The method of claim 31 wherein said pregnant mammal is a woman who is not suffering from inflammation, pyrexia, or pain.
Claim 34
Dependent Claim
33 words
The method of claim 31 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 35
Dependent Claim
71 words
The method of claim 31 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, 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) | 1985-08-16 | 1986-02-15 | 1986-08-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-16 | 1990-02-15 | 1990-08-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-16 | 1994-02-15 | 1994-08-17 | $7700.00 | Window Closed / Lapsed |