Patent US4018931A successfully refreshed from Google Patents.
US4018931A
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Pharmacologically active thiourea and urea compounds
Assignee: Smith Kline & French Laboratories Ltd
•
Filing: 1975-12-04
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Granted: 1977-04-19
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Expires: 1995-12-04
Abstract
Abstract The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-thioureas and ureas 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
2026-11-04 10:32
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; C07D233/84; 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: 13
Claim 1
Independent Claim
189 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: ##STR28## 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 or pyrazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR29## 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 oxygen or sulphur; and R 1 is hydrogen, lower alkyl, benzoyl or di-lower alkylamino-lower alkyl or a pharmaceutically acceptable addition salt thereof with the proviso that X 1 is ##STR30## only when Y and E are sulphur and R 1 is methyl and with the proviso that when X 1 is other than hydrogen or lower alkyl and X 2 is other than hydrogen, X 1 and X 2 are attached at carbon atoms.
Claim 2
Dependent Claim
189 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: ##STR28## 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 or pyrazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR29## 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 oxygen or sulphur; and R 1 is hydrogen, lower alkyl, benzoyl or di-lower alkylamino-lower alkyl or a pharmaceutically acceptable addition salt thereof with the proviso that X 1 is ##STR30## only when Y and E are sulphur and R 1 is methyl and with the proviso that when X 1 is other than hydrogen or lower alkyl and X 2 is other than hydrogen, X 1 and X 2 are attached at carbon atoms.
Claim 3
Dependent Claim
13 words
A pharmaceutical composition of claim 1 in which the heterocyclic compound is N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea.
Claim 4
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 5
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 6
Independent Claim
196 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: ##STR31## 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 or pyrazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR32## 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 oxygen or sulphur; and R 1 is hydrogen, lower alkyl, benzoyl or di-lower alkylamino-lower alkyl or a pharmaceutically acceptable addition salt thereof with the proviso that X 1 is ##STR33## only when Y and E are sulphur and R 1 is methyl and with the proviso that when X 1 is other than hydrogen or lower alkyl and X 2 is other than hydrogen, X 1 and X 2 are attached at carbon atoms.
Claim 7
Independent Claim
196 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: ##STR31## 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 or pyrazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR32## 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 oxygen or sulphur; and R 1 is hydrogen, lower alkyl, benzoyl or di-lower alkylamino-lower alkyl or a pharmaceutically acceptable addition salt thereof with the proviso that X 1 is ##STR33## only when Y and E are sulphur and R 1 is methyl and with the proviso that when X 1 is other than hydrogen or lower alkyl and X 2 is other than hydrogen, X 1 and X 2 are attached at carbon atoms.
Claim 8
Dependent Claim
12 words
A method of claim 5 in which the heterocyclic compound is N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]thiourea.
Claim 9
Dependent Claim
13 words
A method of claim 5 in which the heterocyclic compound is administered orally.
Claim 10
Dependent Claim
26 words
A method of claim 5 in which the heterocyclic compound is administered in a daily dosage regimen of from about 150 mg. to about 1000 mg.
Claim 11
Independent Claim
198 words
A method of inhibiting gastric acid secretion which comprises administering to an animal in need of inhibition of gastric acid secretion in an effective amount to inhibit gastric acid secretion a heterocyclic compound of the formula: ##STR34## 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 or pyrazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR35## 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 oxygen or sulphur; and R 1 is hydrogen, lower alkyl, benzoyl or di-lower alkylamino-lower alkyl or a pharmaceutically acceptable addition salt thereof with the proviso that X 1 is ##STR36## only when Y and E are sulphur and R 1 is methyl and with the proviso that when X 1 is other than hydrogen or lower alkyl and X 2 is other than hydrogen, X 1 and X 2 are attached at carbon atoms.
Claim 12
Independent Claim
198 words
A method of inhibiting gastric acid secretion which comprises administering to an animal in need of inhibition of gastric acid secretion in an effective amount to inhibit gastric acid secretion a heterocyclic compound of the formula: ##STR34## 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 or pyrazole ring; X 1 is hydrogen, lower alkyl, hydroxyl, trifluoromethyl, benzyl, halogen, amino or ##STR35## 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 oxygen or sulphur; and R 1 is hydrogen, lower alkyl, benzoyl or di-lower alkylamino-lower alkyl or a pharmaceutically acceptable addition salt thereof with the proviso that X 1 is ##STR36## only when Y and E are sulphur and R 1 is methyl and with the proviso that when X 1 is other than hydrogen or lower alkyl and X 2 is other than hydrogen, X 1 and X 2 are attached at carbon atoms.
Claim 13
Dependent Claim
12 words
A method of claim 9 in which the heterocyclic compound is N-methyl-N'-[2-((5-methyl-4-imidazolyl)methylthio)-ethyl]thiourea.
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) | 1980-04-18 | 1980-10-18 | 1981-04-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-18 | 1984-10-18 | 1985-04-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-18 | 1988-10-18 | 1989-04-19 | $7700.00 | Window Closed / Lapsed |