US4276298A
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2-Aryl-1,2-benzisothiazolinone-1,1-dioxides and their use as selective protease inhibitors
Assignee: Merck and Co Inc
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Filing: 1979-09-06
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Granted: 1981-06-30
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Expires: 1999-09-06
Abstract
Abstract The invention concerns novel 2-aryl-1,2-benzisothiazolinone-1,1-dioxide compounds; methods for their preparation; pharmaceutical compositions containing them as an active ingredient; and methods of inhibiting proteases, especially elastase, and of treating emphysema, rheumatoid arthritis, and various inflammatory diseases, for example, bronchial inflammation.
Inventors
- 👤 Howard Jones
- 👤 Robert L. Clark
- 👤 Morris Zimmerman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 11:16
CPC Classifications
C; C07; C07D; C07D275/00; C07D275/04; C07D275/06
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
96 words
A compound of the formula: ##STR24## wherein R is ##STR25## where n is 1 or 2, except where X is fluoro, n may also be up to and including 5; and X is independently selected from (1) fluoro; (2) nitro, except that where X is only nitro, n must be 2 and X must be 2,4- or 3,5-dinitro; (3) trifluoromethyl; (4) cyano; (5) C 1-3 alkoxycarbonyl; (6) C 1-3 alkylcarbonyl (7) carboxyl; (8) carbamoyl; (9) C 1-3 alkylacylamino; (10) C 1-3 alkylsulfonyl; (11) N,N-di(C 1-3 alkyl) sulfamyl; (12) trifluoromethoxy; (13) trifluoromethylthio; (14) trifluoromethylsulfonyl; and (15) trifluoromethylsulfinyl.
Claim 2
Dependent Claim
96 words
A compound of the formula: ##STR24## wherein R is ##STR25## where n is 1 or 2, except where X is fluoro, n may also be up to and including 5; and X is independently selected from (1) fluoro; (2) nitro, except that where X is only nitro, n must be 2 and X must be 2,4- or 3,5-dinitro; (3) trifluoromethyl; (4) cyano; (5) C 1-3 alkoxycarbonyl; (6) C 1-3 alkylcarbonyl (7) carboxyl; (8) carbamoyl; (9) C 1-3 alkylacylamino; (10) C 1-3 alkylsulfonyl; (11) N,N-di(C 1-3 alkyl) sulfamyl; (12) trifluoromethoxy; (13) trifluoromethylthio; (14) trifluoromethylsulfonyl; and (15) trifluoromethylsulfinyl.
Claim 3
Dependent Claim
24 words
A compound of claim 1 wherein n is 2 and X is nitro, trifluoromethyl, or cyano; or n is 5 and X is fluoro.
Claim 4
Dependent Claim
8 words
The compound of claim 1 which is 2-(2,4-dinitrophenyl)-1,2-benzisothiazolinone-1,1-dioxide.
Claim 5
Dependent Claim
8 words
The compound of claim 1 which is 2-(2,3,4,5,6-pentafluorophenyl)-1,2-benzisothiazolinone-1,1-dioxide.
Claim 6
Dependent Claim
8 words
The compound of claim 1 which is 2-(2-cyano-4-nitrophenyl)-1,2-benzisothiazolinone-1,1-dioxide.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is 2-(2,4-dicyanophenyl)-1,2-benzisothiazolinone-1,1-dioxide.
Claim 8
Independent Claim
112 words
A method of selectively inhibiting proteases, especially elastase, comprising the administraion to a patient of a therapeutically effective amount of a compound of the formula: ##STR26## wherein R is ##STR27## where n is 1 or 2, except where X is fluoro, n may also be up to and including 5; and X is independently selected from (1) fluoro; (2) nitro, except that where X is only nitro, n must be 2 and X must be 2,4- or 3,5-dinitro; (3) trifluoromethyl; (4) cyano; (5) C 1-3 alkoxycarbonyl; (6) C 1-3 alkylcarbonyl; (7) carboxyl; (8) carbamoyl; (9) C 1-3 alkylacylamino; (10) C 1-3 alkylsulfonyl; (11) N,N-di(C 1-3 alkyl) sulfamyl; (12) trifluoromethylsulfonyl; and (15) trifluoromethylsulfinyl.
Claim 9
Independent Claim
112 words
A method of selectively inhibiting proteases, especially elastase, comprising the administraion to a patient of a therapeutically effective amount of a compound of the formula: ##STR26## wherein R is ##STR27## where n is 1 or 2, except where X is fluoro, n may also be up to and including 5; and X is independently selected from (1) fluoro; (2) nitro, except that where X is only nitro, n must be 2 and X must be 2,4- or 3,5-dinitro; (3) trifluoromethyl; (4) cyano; (5) C 1-3 alkoxycarbonyl; (6) C 1-3 alkylcarbonyl; (7) carboxyl; (8) carbamoyl; (9) C 1-3 alkylacylamino; (10) C 1-3 alkylsulfonyl; (11) N,N-di(C 1-3 alkyl) sulfamyl; (12) trifluoromethylsulfonyl; and (15) trifluoromethylsulfinyl.
Claim 10
Dependent Claim
24 words
The method of claim 7 wherein n is 2 and X is nitro, trifluoromethyl, or cyano; or n is 5 and X is fluoro.
Claim 11
Dependent Claim
117 words
A pharmaceutical composition for selectively inhibiting proteases, especially elastase, comprising a non-toxic pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of the formula: ##STR28## wherein R is ##STR29## where n is 1 or 2, except where X is fluoro, n may also be up to and including 5; and X is independently selected from (1) fluoro; (2) nitro, except that where X is only nitro, n must be 2 and X must be 2,4- or 3,5-dinitro; (3) trifluoromethyl; (4) cyano; (5) C 1-3 alkoxycarbonyl; (6) C 1-3 alkylcarbonyl; (7) carboxyl; (8) cabamoyl; (9) C 1-3 alkylacylamino; (10) C 1-3 alkylsulfonyl; (11) N,N-di(C 1-3 alkyl) sulfamyl; (12) trifluoromethoxy; (13) trifluoromethylthio; (14) trifluoromethylsulfonyl; and (15) trifluoromethylsulfinyl.
Claim 12
Dependent Claim
117 words
A pharmaceutical composition for selectively inhibiting proteases, especially elastase, comprising a non-toxic pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of the formula: ##STR28## wherein R is ##STR29## where n is 1 or 2, except where X is fluoro, n may also be up to and including 5; and X is independently selected from (1) fluoro; (2) nitro, except that where X is only nitro, n must be 2 and X must be 2,4- or 3,5-dinitro; (3) trifluoromethyl; (4) cyano; (5) C 1-3 alkoxycarbonyl; (6) C 1-3 alkylcarbonyl; (7) carboxyl; (8) cabamoyl; (9) C 1-3 alkylacylamino; (10) C 1-3 alkylsulfonyl; (11) N,N-di(C 1-3 alkyl) sulfamyl; (12) trifluoromethoxy; (13) trifluoromethylthio; (14) trifluoromethylsulfonyl; and (15) trifluoromethylsulfinyl.
Claim 13
Dependent Claim
24 words
The composition of claim 9 wherein n is 2 and X is nitro, trifluoromethyl, or cyano; or n is 5 and X is fluoro.
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) | 1984-06-29 | 1984-12-29 | 1985-06-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-29 | 1988-12-29 | 1989-06-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-29 | 1992-12-29 | 1993-06-30 | $7700.00 | Window Closed / Lapsed |