US4070475A
Expired / Lapsed
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Pharmacologically active guanidine compounds as H-2 histamine receptor inhibitors
Assignee: Smith Kline & French Laboratories Ltd
•
Filing: 1977-02-02
•
Granted: 1978-01-24
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Expires: 1997-02-02
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
2026-11-07 08:36
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; 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; C07D233/68; C07D233/84; C07D233/90; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D241/00; C07D241/02; C07D241/10; C07D241/12; 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; C07D277/32; C07D277/36; C07D277/38; C07D277/40; C07D285/00; C07D285/01; C07D285/02; C07D285/04; C07D285/12; C07D285/125; C07D285/135; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
145 words
A pharmaceutical composition to inhibit H-2 histamine receptors comprising a pharmaceutical carrier and in an effective amount to inhibit said receptors a heterocyclic compound of the formula: ##STR15## wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being a thiazole, isothiazole, oxazole or isoxazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR16## 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.
Claim 2
Dependent Claim
145 words
A pharmaceutical composition to inhibit H-2 histamine receptors comprising a pharmaceutical carrier and in an effective amount to inhibit said receptors a heterocyclic compound of the formula: ##STR15## wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being a thiazole, isothiazole, oxazole or isoxazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR16## 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.
Claim 3
Dependent Claim
13 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is N-cyano-N'-methyl-N"-[2-(2-thiazolylmethylthio)ethyl]guanidine.
Claim 4
Dependent Claim
13 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is N-cyano-N'-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine.
Claim 5
Dependent Claim
13 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is N-cyano-N'-[2-(3-isoxazolylmethylthio)ethyl]-N"-methylguanidine.
Claim 6
Dependent Claim
20 words
A pharmaceutical composition of claim 1 in which the pharmaceutical composition is in the form of a tablet or capsule.
Claim 7
Dependent Claim
25 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is present in an amount of from about 50 mg. to about 250 mg.
Claim 8
Independent Claim
152 words
A method of inhibiting H-2 histamine receptors which comprises administering to an animal in need of inhibition of said receptors in an effective amount to inhibit said receptors a heterocyclic compound of the formula: ##STR17## wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being a thiazole, isothiazole, oxazole or isoxazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR18## 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.
Claim 9
Independent Claim
152 words
A method of inhibiting H-2 histamine receptors which comprises administering to an animal in need of inhibition of said receptors in an effective amount to inhibit said receptors a heterocyclic compound of the formula: ##STR17## wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being a thiazole, isothiazole, oxazole or isoxazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR18## 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.
Claim 10
Dependent Claim
12 words
A method of claim 7 in which the heterocyclic compound is N-cyano-N'-methyl-N"-[2-(2-thiazolylmethylthio)ethyl]guanidine.
Claim 11
Dependent Claim
12 words
A method of claim 7 in which the heterocyclic compound is N-cyano-N'-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine.
Claim 12
Dependent Claim
12 words
A method of claim 7 in which the heterocyclic compound is N-cyano-N'-[2-(3-isoxazolylmethylthio)ethyl]-N"-methylguanidine.
Claim 13
Dependent Claim
13 words
A method of claim 7 in which the heterocyclic compound is administered orally.
Claim 14
Dependent Claim
26 words
A method of claim 7 in which the heterocyclic compound is administered in a daily dosage regimen of from about 150 mg. to about 1000 mg.
Claim 15
Independent Claim
149 words
A method of inhibiting gastric acid secretion which comprises administering to an animal in need thereof in an effective amount to inhibit gastric acid secretion a heterocyclic compound of the formula: ##STR19## wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being a thiazole, isothiazole, oxazole or isoxazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR20## 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.
Claim 16
Independent Claim
149 words
A method of inhibiting gastric acid secretion which comprises administering to an animal in need thereof in an effective amount to inhibit gastric acid secretion a heterocyclic compound of the formula: ##STR19## wherein A is such that there is formed together with the carbon atom shown an unsaturated heterocyclic nucleus, said unsaturated heterocyclic nucleus being a thiazole, isothiazole, oxazole or isoxazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR20## 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.
Claim 17
Dependent Claim
12 words
A method of claim 13 in which the heterocyclic compound is N-cyano-N"-methyl-N"-[2-(2-thiazolymethylthio)ethyl]guanidine.
Claim 18
Dependent Claim
12 words
A method of claim 13 in which the heterocyclic compound is N-cyano-N"-[2-(3-isothiazolylmethylthio)ethyl]-N"-methylguanidine.
Claim 19
Dependent Claim
12 words
A method of claim 13 in which the heterocyclic compound is N-cyano-N'-[2-(3-isoxazolylmethylthio)ethyl]-N"-methylguanidine.
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) | 1981-01-23 | 1981-07-25 | 1982-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-23 | 1985-07-25 | 1986-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-23 | 1989-07-25 | 1990-01-24 | $7700.00 | Window Closed / Lapsed |