US4454151A
Expired / Lapsed
US
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Use of pyrrolo pyrroles in treatment of ophthalmic diseases
Assignee: Syntex USA LLC
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Filing: 1982-03-22
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Granted: 1984-06-12
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Expires: 2002-03-22
Abstract
Abstract Certain known pyrroles have been found to be useful in the topical treatment of various ophthalmic diseases in mammals; especially those originating from or associated with inflammation such as, for example, cystoid macular edema, glaucoma, conjunctivitis, uveitis, diabetic retinopathy and eye surgery or trauma.
Inventors
- 👤 L. David Waterbury
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 00:06
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/40; A61P; A61P27/00; A61P27/02; A61P27/06
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
151 words
A method for treating inflammation of the eye in mammals which method comprises topical application to the eye of a mammal in need thereof a therapeutically effective amount of a pharmaceutical ophthalmic composition containing 0.005-1% wt/vol of a compound chosen from those represented by the formulas: ##STR8## and the individual (l-) and (d-)acid isomers thereof and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein R 1 represents hydrogen; lower alkyl group having from one to four carbon atoms; chloro or bromo; R 2 represents hydrogen, a lower alkyl group having from one to four carbon atoms, a lower alkoxy group having from one to four carbon atoms, chloro, bromo, fluoro; or R 4 S(O)n wherein R 4 is lower alkyl and n is the integer 0, 1 or 2; X represents oxygen or sulphur; and R 5 represents hydrogen or lower alkyl group having from one to four carbon atoms.
Claim 2
Independent Claim
151 words
A method for treating inflammation of the eye in mammals which method comprises topical application to the eye of a mammal in need thereof a therapeutically effective amount of a pharmaceutical ophthalmic composition containing 0.005-1% wt/vol of a compound chosen from those represented by the formulas: ##STR8## and the individual (l-) and (d-)acid isomers thereof and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein R 1 represents hydrogen; lower alkyl group having from one to four carbon atoms; chloro or bromo; R 2 represents hydrogen, a lower alkyl group having from one to four carbon atoms, a lower alkoxy group having from one to four carbon atoms, chloro, bromo, fluoro; or R 4 S(O)n wherein R 4 is lower alkyl and n is the integer 0, 1 or 2; X represents oxygen or sulphur; and R 5 represents hydrogen or lower alkyl group having from one to four carbon atoms.
Claim 3
Independent Claim
154 words
A method for treating corneal neovascularization, uveitis and cystoid macular edema in mammals which method comprises topical application to the eye of a mammal in need thereof a therapeutically effective amount of a pharmaceutical ophthalmic composition containing 0.005-1% wt/vol of a compound chosen from those represented by the formulas: ##STR9## and the individual (l-) and (d)acid isomers thereof and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein R 1 represents hydrogen; lower alkyl group having from one to four carbon atoms; chloro or bromo; R 2 represents hydrogen, a lower alkyl group having from one to four carbon atoms, a lower alkoxy group having from one to four carbon atoms, chloro, bromo, fluoro; or R 4 S(O)n wherein R 4 is lower alkyl and n is the integer 0, 1 or 2; X represents oxygen or sulphur; and R 5 represents hydrogen or lower alkyl group having from one to four carbon atoms.
Claim 4
Independent Claim
154 words
A method for treating corneal neovascularization, uveitis and cystoid macular edema in mammals which method comprises topical application to the eye of a mammal in need thereof a therapeutically effective amount of a pharmaceutical ophthalmic composition containing 0.005-1% wt/vol of a compound chosen from those represented by the formulas: ##STR9## and the individual (l-) and (d)acid isomers thereof and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein R 1 represents hydrogen; lower alkyl group having from one to four carbon atoms; chloro or bromo; R 2 represents hydrogen, a lower alkyl group having from one to four carbon atoms, a lower alkoxy group having from one to four carbon atoms, chloro, bromo, fluoro; or R 4 S(O)n wherein R 4 is lower alkyl and n is the integer 0, 1 or 2; X represents oxygen or sulphur; and R 5 represents hydrogen or lower alkyl group having from one to four carbon atoms.
Claim 5
Dependent Claim
9 words
The method of claim 2 for treating corneal neovascularization.
Claim 6
Dependent Claim
8 words
The method of claim 2 for treating uveitis.
Claim 7
Dependent Claim
10 words
The method of claim 2 for treating cystoid macular edema.
Claim 8
Dependent Claim
14 words
The method of claim 2 wherein compounds are represented by those of Formula (A).
Claim 9
Dependent Claim
10 words
The method of claim 6 wherein R 1 is hydrogen.
Claim 10
Dependent Claim
13 words
The method of claim 6 wherein R 2 is hydrogen, namely 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid.
Claim 11
Dependent Claim
33 words
The method of claim 6 wherein R 2 is R 4 S where R 4 is methyl and the R 2 substituent is at the para-position of the phenyl ring, namely 5-(p-methylthio)benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid.
Claim 12
Dependent Claim
16 words
The method of claim 6 wherein R 2 is methoxy at the para-position, namely 5-(p-methoxy)-benzoyl-1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1-carboxylic acid.
Claim 13
Dependent Claim
10 words
The method of claim 6 wherein R 1 is methyl.
Claim 14
Dependent Claim
143 words
A topical ophthalmic pharmaceutical composition for the treatment of inflammation of the eye comprising an 99% to 99.995% wt/vol of ophthalmologically acceptable excipient in admixture with 0.005-1% wt/vol of a compound chosen from those represented by the formulas: ##STR10## and the individual (l-) and (d-)acid isomers thereof and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein R 1 represents hydrogen; lower alkyl group having from one to four carbon atoms; chloro or bromo; R 2 represents hydrogen, a lower alkyl group having from one to four carbon atoms, a lower alkoxy group having from one to four carbon atoms, chloro, bromo, fluoro; or R 4 S(O)n wherein R 4 is lower alkyl and n is the integer 0, 1 or 2; X represents oxygen or sulphur; and R 5 represents hydrogen or lower alkyl group having from one to four carbon atoms.
Claim 15
Dependent Claim
143 words
A topical ophthalmic pharmaceutical composition for the treatment of inflammation of the eye comprising an 99% to 99.995% wt/vol of ophthalmologically acceptable excipient in admixture with 0.005-1% wt/vol of a compound chosen from those represented by the formulas: ##STR10## and the individual (l-) and (d-)acid isomers thereof and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein R 1 represents hydrogen; lower alkyl group having from one to four carbon atoms; chloro or bromo; R 2 represents hydrogen, a lower alkyl group having from one to four carbon atoms, a lower alkoxy group having from one to four carbon atoms, chloro, bromo, fluoro; or R 4 S(O)n wherein R 4 is lower alkyl and n is the integer 0, 1 or 2; X represents oxygen or sulphur; and R 5 represents hydrogen or lower alkyl group having from one to four carbon atoms.
Claim 16
Dependent Claim
16 words
The topical pharmaceutical ophthalmic composition of claim 11 wherein the compound is represented by formula (A).
Claim 17
Dependent Claim
13 words
The topical pharmaceutical ophthalmic composition of claim 13 wherein R 1 is hydrogen.
Claim 18
Dependent Claim
16 words
The topical pharmaceutical ophthalmic composition of claim 14 wherein R 2 is hydrogen; namely, 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid.
Claim 19
Dependent Claim
36 words
The topical pharmaceutical ophthalmic composition of claim 14 wherein R 2 is R 4 S where R 4 is methyl and the R 2 substituent is at the para-position of the phenyl ring; namely, 5-(p-methylthio)benzoyl-1,2-dihydro-3H-pyrrolo-[1,2-a]-pyrrole-1-carboxylic acid.
Claim 20
Dependent Claim
19 words
The topical pharmaceutical ophthalmic composition of claim 14 wherein R 4 is methoxy at the para-position; namely, 5-(p-methoxy)-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid.
Claim 21
Dependent Claim
24 words
The topical pharmaceutical ophthalmic composition of claim 12 wherein the compound is chosen from those represented by formula (A) wherein R 1 is methyl.
References Cited (Backward Citations)
US4087539A
Cited
US4089969A
Cited
US4097579A
Cited
US4140698A
Cited
US4232038A
Cited
US4344943A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-06-12 | 1987-12-12 | 1988-06-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-06-12 | 1991-12-12 | 1992-06-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-06-12 | 1995-12-12 | 1996-06-12 | $7700.00 | Window Closed / Lapsed |