US5288735A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Treatment of glaucoma
Assignee: Individual
•
Filing: 1992-06-15
•
Granted: 1994-02-22
•
Expires: 2012-06-15
Abstract
Abstract Method of treating glaucoma in a mammal, comprising administering to the mammal an effective amount of an active water-soluble carbonic anhydrase inhibitor having the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of H, --OH, --CN and --OCH 3 , R 2 is methyl or a lower alkyl having from two to about 5 carbon atoms, R 3 is selected from the group consisting of NHCHR 4 --, R 5 NHCHR 4 --, R 5 NHCHR 4 --, ##STR2## R 4 is selected from lower alkyl having from one to about five carbon atoms, or a naturally occurring amino acid side-chain, and R 5 is selected from the group consisting of H, CH 3 --, HCO--, CH 3 CO-- and X--CH 2 CO-- wherein X is a halogen atom and stereoisomers thereof.
Inventors
- 👤 Seymour F. Trager
- 👤 G. Michael Blackburn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 14:46
CPC Classifications
C; C07; C07D; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125; C07D285/135; C07D417/00; C07D417/02; C07D417/12
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
119 words
A compound of the formula: ##STR17## or a pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of H, --OH, --CN and --OCH 3 ; R 2 is a methyl or a lower alkyl having from two to five carbon atoms; R 3 is selected from the group consisting of HNHCHR 4 --, R 5 NHCHR 4 --, R 5 NHCH 2 CHR 4 --, ##STR18## R 4 is a lower alkyl having two or five carbon atoms, or a naturally occurring amino acid side chain; R 5 is selected from the group consisting of CH 3 --, HCO--, CH 3 CO--, and X--CH 2 CO-- wherein X is a halogen atom; and stereoisomers thereof.
Claim 2
Dependent Claim
119 words
A compound of the formula: ##STR17## or a pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of H, --OH, --CN and --OCH 3 ; R 2 is a methyl or a lower alkyl having from two to five carbon atoms; R 3 is selected from the group consisting of HNHCHR 4 --, R 5 NHCHR 4 --, R 5 NHCH 2 CHR 4 --, ##STR18## R 4 is a lower alkyl having two or five carbon atoms, or a naturally occurring amino acid side chain; R 5 is selected from the group consisting of CH 3 --, HCO--, CH 3 CO--, and X--CH 2 CO-- wherein X is a halogen atom; and stereoisomers thereof.
Claim 3
Dependent Claim
15 words
A compound according to claim 1, which is 2-(glycylimino)-3-methyl-1,3,4-thiadiazoline-5-sulphonamide or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
18 words
A compound according to claim 1, which is 2-(L-alanylimino)-3-ethyl-1,3,4-thiaiazoline-5-sulphonamide or its enantiomer or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
18 words
A compound according to claim 1, which is 2-(L-phenylalanylimino)-3-methyl-1,3,4-thiadiazoline-5-sulphonamide or its enantiomer or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
18 words
A compound according to claim 1 which is 2-(L-valylimino)-3-methyl-1,3,4-thiadiazoline-5-sulphonamide or its enantiomer or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
18 words
A compound according to claim 1, in the form of a salt produced by reaction with hydrobromic acid.
Claim 8
Dependent Claim
18 words
A compound according to claim 1, in the form of a salt produced by reaction with hydrochloric acid.
Claim 9
Dependent Claim
18 words
A compound according to claim 1, in the form of a salt produced by reaction with citric acid.
Claim 10
Dependent Claim
138 words
Method of treating glaucoma in a mammal, comprising administering to the mammal an effective amount of an active water-soluble carbonic anhydrase inhibitor having the formula: ##STR19## or a pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of H, --OH, --CN and --OCH 3 ; R 2 is methyl or a lower alkyl having from two to about 5 carbon atoms; R 3 is selected from the group consisting of HNHCHR 4 --, R 5 NHCHR 4 --, R 5 NHCHR 4 --, ##STR20## R 4 is selected from lower alkyl having two or five carbon atoms, or a naturally occurring amino acid side-chain; and R 5 is selected from the group consisting of CH 3 --, HCO--, CH 3 CO-- and X--CH 2 CO-- wherein X is a halogen atom; and stereoisomers thereof.
Claim 11
Dependent Claim
138 words
Method of treating glaucoma in a mammal, comprising administering to the mammal an effective amount of an active water-soluble carbonic anhydrase inhibitor having the formula: ##STR19## or a pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of H, --OH, --CN and --OCH 3 ; R 2 is methyl or a lower alkyl having from two to about 5 carbon atoms; R 3 is selected from the group consisting of HNHCHR 4 --, R 5 NHCHR 4 --, R 5 NHCHR 4 --, ##STR20## R 4 is selected from lower alkyl having two or five carbon atoms, or a naturally occurring amino acid side-chain; and R 5 is selected from the group consisting of CH 3 --, HCO--, CH 3 CO-- and X--CH 2 CO-- wherein X is a halogen atom; and stereoisomers thereof.
Claim 12
Dependent Claim
11 words
The method of claim 9, wherein said inhibitor is administered topically.
Claim 13
Dependent Claim
11 words
The method of claim 9, wherein said inhibitor is administered systemically.
Claim 14
Dependent Claim
19 words
The method of claim 10, wherein said inhibitor is administered in the form of a pharmaceutically acceptable ophthalmic formulation.
Claim 15
Dependent Claim
14 words
The method of claim 12, wherein said formulation contains 0.01-5% by weight active inhibitor.
Claim 16
Dependent Claim
14 words
The method of claim 13, wherein said formulation contains 1-3% by weight active inhibitor.
Claim 17
Dependent Claim
13 words
The method of claim 12, wherein said formulation is administered 1-5 times daily.
Claim 18
Dependent Claim
19 words
The method of claim 15, wherein said formulation is administered such that the daily dosage is from 0.1-20 mg.
Claim 19
Dependent Claim
19 words
The method of claim 11, wherein said inhibitor is administered in the form of a pharmaceutically acceptable systemic formulation.
Claim 20
Dependent Claim
14 words
The method of claim 17, wherein said formulation contains 0.01-5% by weight active inhibitor.
Claim 21
Dependent Claim
14 words
The method of claim 18, wherein said formulation contains 1-3% by weight active inhibitor.
Claim 22
Dependent Claim
13 words
The method of claim 17, wherein said formulation is administered 1-3 times daily.
Claim 23
Dependent Claim
22 words
The method of claim 20, wherein said formulation is administered such that the daily dosage of the inhibitor is from 125-1500 mg.
Claim 24
Dependent Claim
16 words
The method of claim 9, wherein said inhibitor is 2-(glycylimino)-3-methyl-1,3,4-thiadiazoline-5-sulphonamide or a pharmaceutically acceptable salt thereof.
Claim 25
Dependent Claim
19 words
The method of claim 9, wherein said inhibitor is 2-(L-alanylimino)-3-ethyl-1,3,4-thiadiazoline-5-sulphonamide or its enantiomer or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
19 words
The method of claim 9, wherein said inhibitor is 2-(L-phenylalanylimino)-3-methyl-1,3,4-thiadiazoline-5-sulphonamide or its enantiomer or a pharmaceutically acceptable salt thereof.
Claim 27
Dependent Claim
19 words
The method of claim 9, wherein said inhibitor is 2-(L-valylimino)-3-methyl-1,3,4-thiadiazoline-5-sulphonamide or its enantiomer or a pharmaceutically acceptable salt thereof.
Claim 28
Dependent Claim
34 words
The method of claim 9, wherein said inhibitor is administered topically in order to act as a prodrug through release of an aminoarylsulfonamide or a 2-amino-1,3,4-thiodiazole-5-sulfonamide as a result of enzymatic hydrolysis by aminopeptidase.
Claim 29
Dependent Claim
142 words
A pharmaceutically acceptable formulation useful in the treatment of glaucoma, comprising an effective amount of an active, water-soluble carbonic anhydrase inhibitor having the formula: ##STR21## or a pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of H, --OH, --CN and --OCH 3 ; R 2 is a methyl or a lower alkyl having from two to five carbon atoms; R 3 is selected from the group consisting of HNHCHR 4 --, R 5 NHCHR 4 --, R 5 NHCH 2 R 5 NHCH 2 CHR 4 --, ##STR22## R 4 is a lower alkyl having two or five carbon atoms, or a naturally occurring amino acid side chain; R 5 is selected from the group consisting of CH 3 --, HCO--, CH 3 CO--, and X--CH 2 CO-- wherein X is a halogen atom; and stereoisomers thereof.
Claim 30
Dependent Claim
142 words
A pharmaceutically acceptable formulation useful in the treatment of glaucoma, comprising an effective amount of an active, water-soluble carbonic anhydrase inhibitor having the formula: ##STR21## or a pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of H, --OH, --CN and --OCH 3 ; R 2 is a methyl or a lower alkyl having from two to five carbon atoms; R 3 is selected from the group consisting of HNHCHR 4 --, R 5 NHCHR 4 --, R 5 NHCH 2 R 5 NHCH 2 CHR 4 --, ##STR22## R 4 is a lower alkyl having two or five carbon atoms, or a naturally occurring amino acid side chain; R 5 is selected from the group consisting of CH 3 --, HCO--, CH 3 CO--, and X--CH 2 CO-- wherein X is a halogen atom; and stereoisomers thereof.
Claim 31
Dependent Claim
17 words
The formulation of claim 27, wherein the inhibitor is present in an amount of 0.01-5% by weight.
Claim 32
Dependent Claim
17 words
The formulation of claim 28, wherein the inhibitor is present in an amount of 1-3% by weight.
Claim 33
Dependent Claim
19 words
The formulation of claim 27, wherein said inhibitor is 2-(L-alanylimino)-3-ethyl-1,3,4-thiadiazoline-5-sulphonamide or its enantiomer or a pharmaceutically acceptable salt thereof.
Claim 34
Dependent Claim
19 words
The formulation of claim 27, wherein said inhibitor is 2-(L-phenylalanylimino)-3-methyl-1,3,4-thiadiazoline-5-sulphonamide or its enantiomer or a pharmaceutically acceptable salt thereof.
Claim 35
Dependent Claim
29 words
A compound of claim 1, wherein R 3 is HNHCHR 4 -- and R 4 is a naturally occurring amino acid side chain, or a pharmaceutically acceptable salt thereof.
Claim 36
Dependent Claim
20 words
A compound of claim 32, wherein R 4 is a side chain of L-phenylalanine, or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
US5010204A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1997-02-21 | 1997-08-23 | 1998-02-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-02-21 | 2001-08-23 | 2002-02-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-02-21 | 2005-08-23 | 2006-02-22 | $7700.00 | Window Closed / Lapsed |