US3950333A
Expired / Lapsed
US
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Pharmacologically active guanidine compounds
Assignee: Smith Kline & French Laboratories Ltd
•
Filing: 1974-03-14
•
Granted: 1976-04-13
•
Expires: 1994-03-14
Abstract
Abstract The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-guanidines which are inhibitors of histamine activity.
Inventors
- 👤 Graham John Durant
- 👤 John Colin Emmett
- 👤 Charon Robin Ganellin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 17:07
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; A; A61; A61P; A61P29/00; C07D213/24; C07D213/28; C07D213/32; C07D213/36; C07D213/38; C07D213/63; C07D213/65; C07D213/72; C07D213/74; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/66; C07D233/84; C07D233/90; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/12; C07D261/00; C07D261/02; C07D261/06; C07D261/08; C07D263/00; C07D263/02; C07D263/30; C07D263/34; C07D263/46; C07D275/00; C07D275/02; C07D275/03; C07D277/00; C07D277/02; C07D277/20; C07D277/22; C07D277/26; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125; C07D285/135; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
146 words
A compound of the formula: ##SPC10## wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being an imidazole, pyrazole, pyrimidine, pyrazine or pyridazine ring; X 1 is hydrogen, lower alkyl, hydroxy, trifluoromethyl, benzyl, halogen, amino or ##EQU6## in which E' is NH or N-cyano; X 2 is hydrogen or when X 1 is lower alkyl, lower alkyl or halogen; k is 0 to 2 and m is 2 or 3, provided that the sum of k and m is 3 or 4; Y is oxygen, sulphur or NH; E is NR 2 ; R 1 is hydrogen, lower alkyl or di-lower alkylamino-lower alkyl; and R 2 is hydrogen, nitro or cyano, or a pharmaceutically acceptable addition salt thereof with the proviso that X 1 is ##EQU7## only when E is NH or N-cyano.
Claim 2
Dependent Claim
146 words
A compound of the formula: ##SPC10## wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being an imidazole, pyrazole, pyrimidine, pyrazine or pyridazine ring; X 1 is hydrogen, lower alkyl, hydroxy, trifluoromethyl, benzyl, halogen, amino or ##EQU6## in which E' is NH or N-cyano; X 2 is hydrogen or when X 1 is lower alkyl, lower alkyl or halogen; k is 0 to 2 and m is 2 or 3, provided that the sum of k and m is 3 or 4; Y is oxygen, sulphur or NH; E is NR 2 ; R 1 is hydrogen, lower alkyl or di-lower alkylamino-lower alkyl; and R 2 is hydrogen, nitro or cyano, or a pharmaceutically acceptable addition salt thereof with the proviso that X 1 is ##EQU7## only when E is NH or N-cyano.
Claim 3
Dependent Claim
11 words
A compound of claim 1 wherein Y is oxygen or sulphur.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein Y is NH.
Claim 5
Dependent Claim
24 words
A compound of claim 1 wherein said unsaturated heterocyclic nucleus is imidazole, pyrazole, pyrimidine pyrazine or pyridazine and R 2 is hydrogen or nitro.
Claim 6
Dependent Claim
13 words
A compound of claim 4 wherein k is 1 and m is 2.
Claim 7
Dependent Claim
12 words
A compound of claim 1 wherein said unsaturated heterocyclic nucleus is imidazole.
Claim 8
Dependent Claim
28 words
A compound of claim 6 wherein X 1 is hydrogen, methyl, bromo, hydroxyl or amino and X 2 is hydrogen; Y is sulphur and R 1 is methyl.
Claim 9
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidine.
Claim 10
Dependent Claim
10 words
A compound of claim 1, said compound being 2-(4-imidazolylmethylthio)ethyleneguanidine sulphate.
Claim 11
Dependent Claim
9 words
A compound of claim 1, said compound being N-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N'-nitroguanidine.
Claim 12
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-ethyl-N"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidine
Claim 13
Dependent Claim
9 words
A compound of claim 1, said compound being N-[2-((4-bromo-5-imidazolyl)methylthio)ethyl]-N'-cyano-N"-methylguanidine.
Claim 14
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine.
Claim 15
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-[2-(4-imidazolylmethylthio)ethyl]-N"-methylguanidine.
Claim 16
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)-ethyl]-N"-propylguanidine.
Claim 17
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-((1-methyl-2-imidazolyl)-methylthio)ethyl]guanidine.
Claim 18
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-[2-(2-imidazolylmethylthio)ethyl]-N"-methylguanidine.
Claim 19
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-((5-trifluoromethyl-4-imidazolyl)methylthio)ethyl]guanidine.
Claim 20
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-[2-(4-imidazolylmethoxy)ethyl]-N"-methylguanidine.
Claim 21
Dependent Claim
9 words
A compound of claim 1 said compound being N-cyano-N'-methyl-N"-[2-(3-pyrazolylmethylthio)-ethyl]guanidine.
Claim 22
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-(2-pyrazinylmethylthio)ethyl]guanidine.
Claim 23
Dependent Claim
9 words
A compound of claim 1, said compound being N-cyano-N'-methyl-N"-[2-(3-pyridazinylmethylthio)ethyl]guanidine.
References Cited (Backward Citations)
US3354174A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-04-13 | 1979-10-13 | 1980-04-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-13 | 1983-10-13 | 1984-04-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-13 | 1987-10-13 | 1988-04-13 | $7700.00 | Window Closed / Lapsed |