US4724235A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-(arylthioalkyl)-N'-(aminoalkyl)ureas useful in the treatment of arrhythmia
Assignee: Wyeth LLC
•
Filing: 1986-03-31
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Granted: 1988-02-09
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Expires: 2006-03-31
Abstract
Abstract N-(Arylthioalkyl)-N'-(aminoalkyl)ureas and thioureas and oxidation derivatives having the formula ##STR1## wherein B is thio, sulfinyl or sulfonyl; R 1 and R 2 are hydrogen, loweralkyl, cycloalkyl, 2-furanyl, phenyl, substituted phenyl or phenyl-loweralkyl and R 3 and R 4 are hydrogen, loweralkyl, phenyl or phenyl-loweralkyl wherein phenyl is optionally substituted, or R 3 and R 4 taken with the adjacent nitrogen form a heterocyclic residue. The compounds are useful in the treatment of cardiac arrhythmia.
Inventors
- 👤 James R. Shanklin, Jr.
- 👤 Christopher P. Johnson, III
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 04:48
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07C; C07C255/00; C07C317/00; C07C317/26; C07C317/28; C07C323/00; C07C323/23; C07C323/39; C07C323/43; C07C323/44; C07C335/00; C07C335/04; C07C335/06; C07C335/08; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 58
Claim 1
Independent Claim
232 words
A method of treating cardiac arrhythmia which comprises internally admimistering to a living animal an antiarrhythmic effective amount of a compound having the formula: ##STR28## wherein; Ar is selected from the group consisting of 1 and 2-naphthyl, 2,3-dihydro-1H-inden-4(or 5)yl, 2-furanyl, phenyl or phenyl substituted by 1-3 radicals which may be the same or different selected from the group consisting of loweralkyl, loweralkoxy, halogen, trifluoromethyl, nitro, cyano, hydroxy, amino, dimethylamino or ##STR29## wherein R 5 and R 6 are selected from hydrogen or loweralkyl, and Ar may include one or two intervening methylene groups attached to B, R 1 and R 2 are selected from the group consisting of hydrogen, loweralkyl, cycloalkyl, phenyl or phenyl-loweralkyl wherein phenyl may be substituted by halogen, loweralkyl, loweralkoxy, allyl or loweralkoxy (1-8 C)-loweralkyl (2-8 C), X is selected from oxygen or sulfur, B is selected from the group consisting of --S--, ##STR30## R 3 and R 4 are selected from the group consisting of hydrogen, loweralkyl, phenyl and phenyl-loweralkyl wherein phenyl may be substituted by halogen, loweralkyl or loweralkoxy and may be the same or different, or R 3 and R 4 taken together with the adjacent nitrogen form a heterocyclic residue, alk 1 and alk 2 are selected from the group consisting of loweralkylene or loweralkylene-loweralkyl and may be the same or different, the pharmaceutically acceptable addition salts and hydrates of the salts and free bases.
Claim 2
Independent Claim
232 words
A method of treating cardiac arrhythmia which comprises internally admimistering to a living animal an antiarrhythmic effective amount of a compound having the formula: ##STR28## wherein; Ar is selected from the group consisting of 1 and 2-naphthyl, 2,3-dihydro-1H-inden-4(or 5)yl, 2-furanyl, phenyl or phenyl substituted by 1-3 radicals which may be the same or different selected from the group consisting of loweralkyl, loweralkoxy, halogen, trifluoromethyl, nitro, cyano, hydroxy, amino, dimethylamino or ##STR29## wherein R 5 and R 6 are selected from hydrogen or loweralkyl, and Ar may include one or two intervening methylene groups attached to B, R 1 and R 2 are selected from the group consisting of hydrogen, loweralkyl, cycloalkyl, phenyl or phenyl-loweralkyl wherein phenyl may be substituted by halogen, loweralkyl, loweralkoxy, allyl or loweralkoxy (1-8 C)-loweralkyl (2-8 C), X is selected from oxygen or sulfur, B is selected from the group consisting of --S--, ##STR30## R 3 and R 4 are selected from the group consisting of hydrogen, loweralkyl, phenyl and phenyl-loweralkyl wherein phenyl may be substituted by halogen, loweralkyl or loweralkoxy and may be the same or different, or R 3 and R 4 taken together with the adjacent nitrogen form a heterocyclic residue, alk 1 and alk 2 are selected from the group consisting of loweralkylene or loweralkylene-loweralkyl and may be the same or different, the pharmaceutically acceptable addition salts and hydrates of the salts and free bases.
Claim 3
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-[(4-chlorophenyl)thio]ethyl]-N'-[2-(dimethylamino)ethyl]-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(dimethylamino)ethyl]-N-(1-methylethyl)-N-[2-[(2-naphthylene)thio]ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-N'-[2-(dimethylamino)ethyl]-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-[(4-chlorophenyl)sulfonyl]-N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-N'-[2-(dimethylamino)ethyl]-N'-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-[(4-chlorophenyl)sulfonyl]ethyl]-N'-(dimethylamino)ethyl]-N-(1-methylethyl)thiourea or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-[(4-chlorophenyl)sulfinyl)ethyl]-N'-[2-(dimethylamino)ethyl]-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(dimethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(dimethylamino)ethyl]-N-(1-methylethyl)-N-[2-[(1-naphthalenesulfonyl)]ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]-N'-[2-(1-pyrrolidinyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-(2-aminoethyl)-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(dimethylamino)ethyl]-N-(1-methylethyl)-N-[2-(1-naphthalenylthio)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[2-[(4-methylphenyl)sulfonyl]ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-[(3,4-dichlorophenyl)sulfonyl]ethyl]-N'-(dimethylamino)ethyl]-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[3-(diethylamino)ethyl]-N-(1-methylethyl)-N-[2-[(4-methylphenyl)sulfinyl]ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[3-(diethylamino)propyl]-N-(1-methylethyl)-N-[3-(phenylsulfonyl)propyl]urea or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[3-(phenylsulfonyl)propyl]urea or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[3-(diethylamino)propyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-[2-[(4-fluorophenyl)sulfonyl]ethyl]-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 23
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(1-methylethyl)-N'-[2-[bis(1-methylethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 24
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(1-methylethyl)-N'-[2-[methyl-(2-phenylethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 25
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(1-methylethyl)-N-[2-[methyl(phenylmethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(ethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 27
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(hexahydro-1H-azepin-1-yl)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 28
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(1-methylethyl)-N'-[2-[(methyl)(phenyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 29
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(2-phenylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(-methylethyl)-N'-[2-(4-morpholinyl)ethyl]-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 31
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]-N'-[2-(1-piperidinyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 32
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-(diethylamino)ethyl]-N-ethyl-N'-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 33
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-(diethylamino)ethyl]-N-ethyl-N'-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 34
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-(diethylamino)ethyl]-N'-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 35
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-[2-[4-methoxyphenyl)sulfonyl]ethyl]-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 36
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[3-(diethylamino)propyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl] or a pharmaceutically acceptable salt thereof.
Claim 37
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-[2-[4-(1,1-dimethylethyl)phenyl]sulfonyl]ethyl-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 38
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylthio)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 39
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]thiourea or a pharmaceutically acceptable salt thereof.
Claim 40
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[2-[(phenylmethyl)sulfonyl]ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 41
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[3-(diethylamino)propyl]-N-(1-methylethyl)-N-[2-[(phenylmethyl)sulfonyl]ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 42
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-ethyl-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 43
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[4-(diethylamino)butyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 44
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)-1-methylethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 45
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]-N'-[3-(1piperidinyl)propyl]urea or a pharmaceutically acceptable salt thereof.
Claim 46
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[2-(phenylsulfinyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 47
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(phenylmethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 48
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 49
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[5-(diethylamino)pentyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 50
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-(1-methylethyl)-N'-[3-(4-methyl-1-piperazinyl)propyl]-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 51
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[1-methyl-2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 52
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N-[2-(diethylamino)ethyl]-N-methyl-N'-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 53
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[4-(phenylsulfonyl)butyl]urea or a pharmaceutically acceptable salt thereof.
Claim 54
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(1-methylethyl)-N-[5-(phenylsulfonyl)pentyl]urea or a pharmaceutically acceptable salt thereof.
Claim 55
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(3-ethoxypropyl)-N-[2-(phenylsulfonyl)ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 56
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-(2-methoxyethyl)-N-[2-(phenylsulfonyl)-ethyl]urea or a pharmaceutically acceptable salt thereof.
Claim 57
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-[2-[(4-ethoxyphenyl)sulfonyl]ethyl]-N-(1-methylethyl)urea or a pharmaceutically acceptable salt thereof.
Claim 58
Dependent Claim
17 words
The method of claim 1 wherein the compound administered is N'-[2-(diethylamino)ethyl]-N-[2-(phenylsulfonyl)ethyl]-N-(2-propenyl)urea or a pharmaceutically acceptable salt thereof.
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) | 1991-02-08 | 1991-08-10 | 1992-02-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-02-08 | 1995-08-10 | 1996-02-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-02-08 | 1999-08-10 | 2000-02-09 | $7700.00 | Window Closed / Lapsed |