US4439435A
Expired / Lapsed
US
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Isoureas and isothioureas
Assignee: Smith Kline & French Laboratories Ltd
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Filing: 1981-08-06
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Granted: 1984-03-27
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Expires: 2001-08-06
Abstract
Abstract The compounds are isoureas and isothioureas which have an O- or S- alkylpyrimidone substituent and which are histamine H2-antagonists and antiinflammatory agents. A specific compound of this invention is 2-[5-(O-isoureido)pentylamino]-5-(6-methyl-3-pyridyl-methyl)-4-pyrimid one.
Inventors
- 👤 Charon R. Ganellin
- 👤 Robert J. Ife
- 👤 David A. A. Owen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:59
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/46; C07D239/47; A; A61; A61P; A61P43/00; C07D239/42; C07D239/52; C07D239/54; C07D239/545
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
191 words
A compound of the formula ##STR10## ##STR11## in which R 1 and R 2 are hydrogen or lower alkyl; Y is sulphur or oxygen; n is from 3 to 8; X is oxygen or sulphur; Z is hydrogen or lower alkyl; A is straight or branched C 1 -C 5 alkylene or --(CH 2 ) p W(CH 2 ) q -- where W is oxygen or sulphur and the sum of p and q is 1 to 4; and B is methyl, C 3 -C 6 cycloalkyl, a heteroaryl group selected from furyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, imidazolyl, thiadiazolyl, benzimidazolyl and benzthiazolyl, said heteroaryl being optionally substituted by one or more lower alkyl, lower alkoxy, halo, hydroxy or amino groups or B is a naphthyl, 5- or 6-(2,3-dihydro-1,4-benzodioxinyl) or 4- or 5-(1,3-benzodioxolyl) group, or a phenyl group optionally substituted with one or more lower alkyl, lower alkoxy, halogen, phenyl(lower alkoxy), hydroxy, lower alkoxy-lower alkoxy, trifluoromethyl, di(lower alkyl)amino, phenoxy, halophenoxy, lower alkoxyphenoxy, phenyl, halophenyl or lower alkoxyphenyl group, or, provided A is alkylene, B can be hydrogen, in the form of the free base or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
191 words
A compound of the formula ##STR10## ##STR11## in which R 1 and R 2 are hydrogen or lower alkyl; Y is sulphur or oxygen; n is from 3 to 8; X is oxygen or sulphur; Z is hydrogen or lower alkyl; A is straight or branched C 1 -C 5 alkylene or --(CH 2 ) p W(CH 2 ) q -- where W is oxygen or sulphur and the sum of p and q is 1 to 4; and B is methyl, C 3 -C 6 cycloalkyl, a heteroaryl group selected from furyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, imidazolyl, thiadiazolyl, benzimidazolyl and benzthiazolyl, said heteroaryl being optionally substituted by one or more lower alkyl, lower alkoxy, halo, hydroxy or amino groups or B is a naphthyl, 5- or 6-(2,3-dihydro-1,4-benzodioxinyl) or 4- or 5-(1,3-benzodioxolyl) group, or a phenyl group optionally substituted with one or more lower alkyl, lower alkoxy, halogen, phenyl(lower alkoxy), hydroxy, lower alkoxy-lower alkoxy, trifluoromethyl, di(lower alkyl)amino, phenoxy, halophenoxy, lower alkoxyphenoxy, phenyl, halophenyl or lower alkoxyphenyl group, or, provided A is alkylene, B can be hydrogen, in the form of the free base or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
11 words
A compound according to claim 1 in which X is oxygen.
Claim 4
Dependent Claim
11 words
A compound according to claim 2 in which Z is hydrogen.
Claim 5
Dependent Claim
22 words
A compound according to any one of claims 1, 2 or 3 in which R 1 and R 2 are both hydrogen.
Claim 6
Dependent Claim
11 words
A compound according to claim 1 in which Y is oxygen.
Claim 7
Dependent Claim
13 words
A compound according to claim 1 in which n is 5 or 6.
Claim 8
Dependent Claim
11 words
A compound according to claim 1 in which A is methylene.
Claim 9
Dependent Claim
17 words
A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable diluent or carrier.
Claim 10
Dependent Claim
20 words
A method of blocking histamine H 2 -receptors which comprises administering to an animal a compound according to claim 1.
Claim 11
Dependent Claim
26 words
A method of simultaneously blocking histamine H 1 -receptors and histamine H 2 -receptors which comprises administering to an animal a compound according to claim 1.
Claim 12
Dependent Claim
18 words
A method of producing antiinflammatory activity which comprises administering to an animal a compound according to claim 1.
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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) | 1987-03-27 | 1987-09-26 | 1988-03-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-27 | 1991-09-26 | 1992-03-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-27 | 1995-09-26 | 1996-03-27 | $7700.00 | Window Closed / Lapsed |