Patent US4544654A successfully refreshed from Google Patents.
US4544654A
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Substituted sulfonamidobenzamides, antiarrhythmic agents and compositions thereof
Assignee: Bayer Pharma AG
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Filing: 1984-03-20
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Granted: 1985-10-01
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Expires: 2004-03-20
Abstract
Abstract Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.
Inventors
- 👤 David D. Davey
- 👤 William C. Lumma, Jr.
- 👤 Ronald A. Wohl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 17:49
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/12; C07D295/125; C07D295/13; A; A61; A61P; A61P9/00; A61P9/06; C07C; C07C255/00
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
274 words
A compound according to the formula: ##STR7## wherein R=lower alkyl, cycloalkyl, cycloalkyl(lower)alkyl, benzyl, or benzyl substituted by halogen, loweralkyl, loweralkoxy, or lower alkyl substituted by hydroxy, lower alkoxy, carbamoyl, N-loweralkylcarbamoyl, N,N-diloweralkylcarbamoyl and sulfamoyl; X,X 1 =hydrogen and halogen; R 1 =hydrogen, loweralkyl, unsaturated loweralkyl, loweralkoxyloweralkyl, or collectively with R 2 is an alkylene chain forming an azetidine, pyrrolidine, piperidine, or hexahydroazepine ring, or collectively with R 3 is a bond or an alkylene chain forming an azetidine, pyrrolidine, piperidine or a hexahydroazepine ring, or collectively with R 5 may produce a piperazine or a hexahydro-1,4-diazepine ring system; R 2 =hydrogen, loweralkyl or collectively with R 3 is a bond or an alkylene chain to form a saturated carbocyclic ring of from 4 to 8 ring carbon atoms. R 3 ,R 4 =hydrogen, loweralkyl or collectively is an alkylene chain forming a saturated carbocyclic ring of from 4 to 6 ring carbon atoms; R 5 ,R 6 =unsaturated loweralkyl, C 1 -C 12 straight or branched chain alkyl, C 3 -C 6 cycloalkyl, cycloalkyl(lower)alkyl, or when taken together form a saturated heterocyclic ring of from 4 to 8 ring members which may be substituted by one or more methyl groups or optionally contains a --O--, or ##STR8## linkage wherein p is the integer 0, 1 or 2; R 6 =loweralkyl substituted by phenyl which may be substituted by up to 3 substituents selected from hydroxy or methoxy groups; n=0, 1, 2; and the pharmaceutically acceptable salts thereof; with the proviso that: (a) when any of R 1 , R 5 or R 6 is unsaturated loweralkyl, the unsaturation cannot be alpha to the nitrogen atom.
Claim 2
Dependent Claim
274 words
A compound according to the formula: ##STR7## wherein R=lower alkyl, cycloalkyl, cycloalkyl(lower)alkyl, benzyl, or benzyl substituted by halogen, loweralkyl, loweralkoxy, or lower alkyl substituted by hydroxy, lower alkoxy, carbamoyl, N-loweralkylcarbamoyl, N,N-diloweralkylcarbamoyl and sulfamoyl; X,X 1 =hydrogen and halogen; R 1 =hydrogen, loweralkyl, unsaturated loweralkyl, loweralkoxyloweralkyl, or collectively with R 2 is an alkylene chain forming an azetidine, pyrrolidine, piperidine, or hexahydroazepine ring, or collectively with R 3 is a bond or an alkylene chain forming an azetidine, pyrrolidine, piperidine or a hexahydroazepine ring, or collectively with R 5 may produce a piperazine or a hexahydro-1,4-diazepine ring system; R 2 =hydrogen, loweralkyl or collectively with R 3 is a bond or an alkylene chain to form a saturated carbocyclic ring of from 4 to 8 ring carbon atoms. R 3 ,R 4 =hydrogen, loweralkyl or collectively is an alkylene chain forming a saturated carbocyclic ring of from 4 to 6 ring carbon atoms; R 5 ,R 6 =unsaturated loweralkyl, C 1 -C 12 straight or branched chain alkyl, C 3 -C 6 cycloalkyl, cycloalkyl(lower)alkyl, or when taken together form a saturated heterocyclic ring of from 4 to 8 ring members which may be substituted by one or more methyl groups or optionally contains a --O--, or ##STR8## linkage wherein p is the integer 0, 1 or 2; R 6 =loweralkyl substituted by phenyl which may be substituted by up to 3 substituents selected from hydroxy or methoxy groups; n=0, 1, 2; and the pharmaceutically acceptable salts thereof; with the proviso that: (a) when any of R 1 , R 5 or R 6 is unsaturated loweralkyl, the unsaturation cannot be alpha to the nitrogen atom.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein R is loweralkyl.
Claim 4
Dependent Claim
13 words
A compound of claim 1 wherein X and X 1 are both hydrogen.
Claim 5
Dependent Claim
17 words
A compound of claim 1 wherein R 1 ,R 2 ,R 3 and R 4 are hydrogen.
Claim 6
Dependent Claim
22 words
A compound of claim 1 wherein R 5 and R 6 are are C 1 -C 12 straight or branched chain alkyl.
Claim 7
Dependent Claim
16 words
A compound of claim 1 wherein R 1 collectively with R 5 produces a piperazine ring.
Claim 8
Dependent Claim
38 words
A compound of claim 1 wherein R is loweralkyl, R 5 and R 6 are C 1 -C 12 straight or branched chain alkyl and X,X 1 ,R 1 ,R 2 ,R 3 and R 4 are hydrogen.
Claim 9
Dependent Claim
34 words
A compound of claim 1 wherein R is loweralkyl, X, X 1 , R 2 , R 3 , R 4 , are hydrogen and R 1 with R 5 forms a piperazine ring.
Claim 10
Dependent Claim
8 words
A compound of claim 7 which is N-[2-(diethylamino)ethyl]-4-[(methylsulfonyl)amino]benzamide.
Claim 11
Dependent Claim
8 words
A compound of claim 7 which is N-[3-(diethylamino)propyl]-4-[(methylsulfonyl)amino]benzamide.
Claim 12
Dependent Claim
8 words
A compound of claim 7 which is 4-[(butylsulfonyl)amino-N-[2-(diethylamino)ethyl]benzamide.
Claim 13
Dependent Claim
8 words
A compound of claim 7 which is N-[2-(diethylamino)ethyl]-4-[(ethylsulfonyl)amino]benzamide.
Claim 14
Dependent Claim
8 words
A compound of claim 7 which is N-[4-(diethylamino)butyl]-4-[(methylsulfonyl)amino]benzamide.
Claim 15
Dependent Claim
8 words
A compound of claim 7 which is N-[2-(dimethylamino)ethyl]-4-[(methylsulfonyl)amino]benzamide.
Claim 16
Dependent Claim
8 words
A compound of claim 7 which is N-[2-(dipropylamino)ethyl]-4-[(methylsulfonyl)amino]benzamide.
Claim 17
Dependent Claim
8 words
A compound of claim 7 which is N-[2-(diisopropylamino)ethyl]-4-[(methylsulfonyl)amino]benzamide.
Claim 18
Dependent Claim
8 words
A compound of claim 1 which is (4-[(methylsulfonyl)amino]-N-[2-(4-morpholinyl)ethyl]benzamide.
Claim 19
Dependent Claim
8 words
A compound of claim 8 which is 4-methyl-1-[4-[(methylsulfonyl)amino]benzoyl]piperazine.
Claim 20
Dependent Claim
9 words
A compound of claim 1 which is 4-[(methylsulfonyl)amino]-N-[2-(1- piperidinyl)ethyl]benzamide.
Claim 21
Dependent Claim
8 words
A compound of claim 1 which is 4-[(methylsulfonyl)amino]-N-[2-(1-pyrrolidinyl)ethyl]benzamide.
Claim 22
Dependent Claim
8 words
A compound of claim 1 which is N-[2-(diethylamino)ethyl]-N-methyl-4-[(methylsulfonyl)amino]benzamide.
Claim 23
Dependent Claim
8 words
A compound of claim 1 which is 4-[(methylsulfonyl)amino]-N-[2-(2,2,6,6-tetramethylpiperidino)ethyl]benzamide.
Claim 24
Dependent Claim
9 words
A compound of claim 1 which is 4-[(methylsulfonyl)amino]-N-[2-(thiomorpholin-B 4-yl)ethyl]benzamide.
Claim 25
Dependent Claim
8 words
A compound of claim 1 which is 4-[(methylsulfonyl)amino]-N-[2-(1-oxothiomorpholin-4-yl)ethyl]benzamide.
Claim 26
Dependent Claim
8 words
A compound of claim 1 which is N-[4-[[2-(diethylamino)ethyl]aminocarbonyl]phenyl]benzenemethanesulfonamide.
Claim 27
Dependent Claim
8 words
A compound of claim 7 which is N-[2-(ethyl(heptyl)amino)ethyl-4-[(methylsulfonyl)amino]benzamide.
Claim 28
Dependent Claim
28 words
The method of treating arrhythmias in a mammalian subject in need thereof comprising administering to said subject an antiarrhythmically effective dose of a compound according to claim 1.
Claim 29
Dependent Claim
24 words
A pharmaceutical composition for treating arrhythmias comprising an antiarrhythmic effective amount of a compound of claim 1 together with a non-toxic pharmaceutically acceptable carrier.
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-30 | 1989-04-01 | 1989-10-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-30 | 1993-04-01 | 1993-10-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-30 | 1997-04-01 | 1997-10-01 | $7700.00 | Window Closed / Lapsed |