US4239908A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-aralkenyl-N'-cyano-N"-(heterocyclylthioalkyl)-guanidines
Assignee: GD Searle LLC
•
Filing: 1979-12-10
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Granted: 1980-12-16
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Expires: 1999-12-10
Abstract
Abstract N-aralkenyl-N'-cyano-N"-(heterocyclylthioalkyl)-guanidines and salts thereof which are pharmacologically active as inhibitors of gastric secretion and their preparation from isothioureas are disclosed.
Inventors
- 👤 Gilbert W. Adelstein
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 22:49
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/64; C07C; C07C217/00; C07C217/54; C07C217/56; C07C217/62; C07D233/00; C07D233/54; C07D233/66; C07D233/68; C07D233/88; C07D263/00; C07D263/02; C07D263/30; C07D263/32; C07D263/34; C07D263/48; C07D277/00; C07D277/02; C07D277/20; C07D277/22; C07D277/26; C07D307/38; C07D307/52; C07D319/00; C07D319/10; C07D319/14; C07D319/16; C07D319/18
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
303 words
A compound of the formula ##STR37## or a pharmacologically acceptable salt thereof, wherein A is of the formula: ##STR38## wherein R 1 and R 2 can be the same or different and each represents hydrogen, halogen, hydroxy, trifluoromethyl, alkoxy containing 1 to 7 carbon atoms and either unsubstituted or substituted by aryl or cycloalkyl, or amino either unsubstituted or substituted with at least one acyl or alkyl, each containing 1 to 7 carbon atoms, the alkyl being unsubstituted or substituted by aryl or cycloalkyl; or R 1 and R 2 are interconnected forming a group having terminal oxygen atoms which are separated by methylene or ethylene and which are attached to adjacent carbon atoms on the phenyl ring; X represents --O--, --S--, or --N--; R 3 represents hydrogen, halogen or alkyl containing 1 to 7 carbon atoms: R 4 represents hydrogen or alkyl containing 1 to 7 carbon atoms when X is --S-- or ##STR39## and represents hydrogen when S is O; R 5 is alkylene of 1 to 6 carbon atoms; R 6 and R 7 can be the same or different and each represents hydrogen, cycloalkyl or alkyl, each containing 1 to 7 carbon atoms, the alkyl ether unsubstituted or substituted by aryl; or R 6 and R 7 are interconnected forming with the nitrogen atom in formula 3 a 5- or 6- membered ring which can include oxygen; and d is 0, 1 or 2 and e is 2 or 3 when A is of formula 1 or 3; d is 1 or 2 and e is 2 or 3 when A is of formula 2 and X is --S-- or ##STR40## d is 1 and e is 2 when A is of formula 2 and X is --O--; and the sum of d and e is 3 or 4.
Claim 2
Dependent Claim
303 words
A compound of the formula ##STR37## or a pharmacologically acceptable salt thereof, wherein A is of the formula: ##STR38## wherein R 1 and R 2 can be the same or different and each represents hydrogen, halogen, hydroxy, trifluoromethyl, alkoxy containing 1 to 7 carbon atoms and either unsubstituted or substituted by aryl or cycloalkyl, or amino either unsubstituted or substituted with at least one acyl or alkyl, each containing 1 to 7 carbon atoms, the alkyl being unsubstituted or substituted by aryl or cycloalkyl; or R 1 and R 2 are interconnected forming a group having terminal oxygen atoms which are separated by methylene or ethylene and which are attached to adjacent carbon atoms on the phenyl ring; X represents --O--, --S--, or --N--; R 3 represents hydrogen, halogen or alkyl containing 1 to 7 carbon atoms: R 4 represents hydrogen or alkyl containing 1 to 7 carbon atoms when X is --S-- or ##STR39## and represents hydrogen when S is O; R 5 is alkylene of 1 to 6 carbon atoms; R 6 and R 7 can be the same or different and each represents hydrogen, cycloalkyl or alkyl, each containing 1 to 7 carbon atoms, the alkyl ether unsubstituted or substituted by aryl; or R 6 and R 7 are interconnected forming with the nitrogen atom in formula 3 a 5- or 6- membered ring which can include oxygen; and d is 0, 1 or 2 and e is 2 or 3 when A is of formula 1 or 3; d is 1 or 2 and e is 2 or 3 when A is of formula 2 and X is --S-- or ##STR40## d is 1 and e is 2 when A is of formula 2 and X is --O--; and the sum of d and e is 3 or 4.
Claim 3
Dependent Claim
9 words
The compound of claim 1 wherein d is 1.
Claim 4
Dependent Claim
9 words
The compound of claim 1 wherein e is 2.
Claim 5
Dependent Claim
9 words
The compound of claim 1 wherein A is imidazol-4-yl.
Claim 6
Dependent Claim
22 words
The compound of claim 1 wherein R 1 is hydrogen, hydroxy, halogen, methoxy, phenylmethoxy or amino substituted with acetyl, methyl, or phenylmethyl.
Claim 7
Dependent Claim
22 words
The compound of claim 1 wherein R 2 is hydrogen, hydroxy, halogen, methoxy, phenylmethoxy or amino substituted with acetyl, methyl or phenylmethyl.
Claim 8
Dependent Claim
23 words
The compound of claim 1 wherein R 1 and R 2 are interconnected forming a group having terminal oxygen atoms separated by methylene.
Claim 9
Dependent Claim
18 words
The compound of claim 1 wherein A is of formula 1 and R 3 is hydrogen or methyl.
Claim 10
Dependent Claim
18 words
The compound of claim 1 wherein A is of formula 2 and R 4 is hydrogen or methyl.
Claim 11
Dependent Claim
16 words
The compound of claim 1 wherein A is of formula 3 and R 5 is methylene.
Claim 12
Dependent Claim
18 words
The compound of claim 1 wherein A is of formula 3 and R 6 is hydrogen or methyl.
Claim 13
Dependent Claim
18 words
The compound of claim 1 wherein A is of formula 3 and R 7 is hydrogen or methyl.
Claim 14
Dependent Claim
20 words
The compound of claim 1 wherein A is of formula 3, R 6 is methyl and R 7 is hydrogen.
Claim 15
Dependent Claim
20 words
The compound of claim 1 wherein A is of formula 3 and R 6 and R 7 are each methyl.
Claim 16
Dependent Claim
23 words
The compound of claim 1 wherein A is of formula 3 and R 6 and R 7 are interconnected forming tetramethylene or pentamethylene.
Claim 17
Dependent Claim
8 words
The compound of claim 1 being N-cyano-N'-[2-(((5-methyl-1H-imidazol-4-yl)methyl)thio)ethyl]-N"-(3-phenyl-2-propen-1-yl)guanidine hydrochloride.
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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) | 1983-12-16 | 1984-06-16 | 1984-12-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-12-16 | 1988-06-16 | 1988-12-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-12-16 | 1992-06-16 | 1992-12-16 | $7700.00 | Window Closed / Lapsed |