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US4097579A
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5-(2-Pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid derivatives and process for the production thereof
Assignee: Syntex USA LLC
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Filing: 1977-03-31
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Granted: 1978-06-27
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Expires: 1997-03-31
Abstract
Abstract Novel 5-(2-pyrroyl) and 5-(N-lower alkyl-2-pyrroyl)-1,2-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 each of R and R1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms and process for the production of such compounds; 5-(N-methyl-2-pyrroyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid is representative of the class. These compounds are useful as anti-inflammatory analgesic and anti-pyretic agents and as smooth muscle relaxants.
Inventors
- 👤 Joseph Martin Muchowski
- 👤 Arthur Frederick Kluge
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 13:49
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A61; A61P; A61P13/00; A61P13/02; A61P15/00; A61P25/00; A61P25/04; A61P29/00; C07D207/00; C07D207/02; C07D207/30; C07D207/34
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
60 words
A compound selected from the group of those represented by the formula ##STR8## and the individual (l)-acid and (d)-acid isomers thereof and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 2
Dependent Claim
60 words
A compound selected from the group of those represented by the formula ##STR8## and the individual (l)-acid and (d)-acid isomers thereof and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein R is hydrogen.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein R is methyl.
Claim 5
Dependent Claim
16 words
The carboxylic acid compound of claim 2 wherein R 1 is hydrogen, 5-(2-pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a! pyrrole-1-carboxylic acid.
Claim 6
Dependent Claim
12 words
The isopropyl ester of the compound of claim 4, isopropyl 5-(2-pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylate.
Claim 7
Dependent Claim
15 words
The carboxylic acid compound of claim 2 wherein R 1 is methyl, 5-(N-methyl-2-pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid.
Claim 8
Dependent Claim
13 words
The isopropyl ester of the compound of claim 6, isopropyl 5-(N-methyl-2-pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylate acid.
Claim 9
Dependent Claim
15 words
The carboxylic acid compound of claim 3 wherein R 1 is hydrogen, 5-(2-pyrroyl)-1,2-dihydro-6-methyl-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid.
Claim 10
Dependent Claim
12 words
The isopropyl ester of the compound of claim 8, isopropyl 5-(2-pyrroyl)-1,2-dihydro-6-methyl-3H-pyrrolo 1,2-a!pyrrole-1-carboxylate.
Claim 11
Dependent Claim
15 words
The carboxylic acid compound of claim 3 wherein R 1 is methyl, 5-(N-methyl-2-pyrroyl)-1,2-dihydro-6-methyl-3H-pyrrolo 1,2-a!pyrrole-1-carboxylic acid.
Claim 12
Dependent Claim
12 words
The isopropyl ester of the compound of claim 10, isopropyl 5-(N-methyl-2-pyrroyl)-1,2-dihydro-6-methyl-3H-pyrrolo 1,2-a!pyrrole-1-carboxylate.
Claim 13
Dependent Claim
16 words
A sodium, potassium or calcium salt of the compounds according to Formula (A) of claim 1.
Claim 14
Dependent Claim
19 words
The sodium salt compound of claim 12 wherein R is hydrogen and R 1 is methyl, sodium 5-(N-methyl-2-pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylate.
Claim 15
Dependent Claim
9 words
An (l)-acid isomer of Formula (A) of claim 1.
Claim 16
Dependent Claim
17 words
The compound of claim 14 wherein R is hydrogen and R 1 is methyl, (l)-5-(N-methyl-2-pyrroyl)-1,2-dihydro-3H-pyrroyl 1,2-a!pyrrole-1-carboxylic acid.
Claim 17
Dependent Claim
16 words
A sodium, potassium or calcium salt of an (l)-acid isomer of Formula (A) of claim 1.
Claim 18
Dependent Claim
19 words
The sodium salt compound of claim 16 wherein R is hydrogen and R 1 is methyl, sodium (l)-5-(N-methyl-2-pyrroyl)-1,2-dihydro-3H-pyrrolo 1,2-a!pyrrole-1-carboxylate.
Claim 19
Dependent Claim
77 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 represented by the formula ##STR9## or the (l)-acid isomers of Formula (A), and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 20
Dependent Claim
77 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 represented by the formula ##STR9## or the (l)-acid isomers of Formula (A), and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 21
Independent Claim
76 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 represented by the formula ##STR10## or the (l)-acid isomer of Formula (A), and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 22
Independent Claim
76 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 represented by the formula ##STR10## or the (l)-acid isomer of Formula (A), and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 23
Dependent Claim
80 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 thereapeutically effective amount of a compound represented by the formula ##STR11## or the (l)-acid isomers of Formula (A), and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 24
Dependent Claim
80 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 thereapeutically effective amount of a compound represented by the formula ##STR11## or the (l)-acid isomers of Formula (A), and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 25
Independent Claim
78 words
A method comprising administering to a pregnant mammal to delay the onset of parturition a pharmaceutically effective amount of a compound selected from the group of compounds represented by the formula ##STR12## or the (l)-acid isomers of Formula (A), and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 26
Independent Claim
78 words
A method comprising administering to a pregnant mammal to delay the onset of parturition a pharmaceutically effective amount of a compound selected from the group of compounds represented by the formula ##STR12## or the (l)-acid isomers of Formula (A), and the pharmaceutically acceptable, non-toxic alkyl esters having from one to twelve carbon atoms and salts thereof, wherein each of R and R 1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms.
Claim 27
Dependent Claim
21 words
The method of claim 21 wherein said pregnant mammal is a woman who is not suffering from inflammation, pyrexia, or pain.
Claim 28
Dependent Claim
33 words
The method of claim 22 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 29
Dependent Claim
71 words
The method of claim 21 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)
US3206470A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-26 | 1981-12-26 | 1982-06-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-26 | 1985-12-26 | 1986-06-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-26 | 1989-12-26 | 1990-06-27 | $7700.00 | Window Closed / Lapsed |