Patent US4539207A successfully refreshed from Google Patents.
US4539207A
Expired / Lapsed
US
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Pyrimidine compounds
Assignee: Smith Kline & French Laboratories Ltd
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Filing: 1980-06-04
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Granted: 1985-09-03
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Expires: 2000-06-04
Abstract
Abstract The compounds are substituted pyrimidine compounds which are histamine H 2 -antagonists. A specific compound of the present invention is 2-[2-(5-dimethylaminomethyl)-2-furylmethylthio)ethylamino]-5-(3-pyridylmethyl)-4-pyrimidone.
Inventors
- 👤 Thomas H. Brown
- 👤 Robert J. Ife
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:44
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/40; C07D213/54; C07D213/55; C07D213/60; C07D213/61; C07D213/62; C07D213/63; C07D213/64; C07D213/78; C07D213/84; C07D213/85; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/56; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/18; C07D333/20
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
222 words
A compound of the formula: ##STR7## in which D is hydrogen or R 1 R 2 N(CH 2 ) m --, R 1 and R 2 are hydrogen, lower alkyl, phenyl(lower alkyl) or R 1 and R 2 taken together with the nitrogen atom shown can form a pyrrolidino or piperidino group, m is from 1 to 6, X is oxygen or sulphur, Y is sulphur, oxygen or methylene, n is 2 or 3, Z is hydrogen or lower alkyl, A is C 1 -C 5 alkylene or --(CH 2 ) p W(CH 2 ) q -- where W is oxygen or sulphur and p and q are such that their sum is from 1 to 4, and B is hydrogen, methyl, C 3 -C 6 cycloalkyl, a heteroaryl group selected from furyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, imidazolyl, thiadiazolyl, benzimidazolyl and benzthiazolyl, said heteroaryl group being optionally substituted by one or more of the groups lower alkyl, lower alkoxy, halo, hydroxy and amino, or B is a naphthyl, or a 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 alkoxylower alkoxy, trifluoromethyl, di(lower alkyl)amino, phenoxy, halophenoxy, lower alkoxyphenoxy, phenyl, halophenyl or lower alkoxyphenyl groups, in the form of the free base or its pharmaceutically acceptable acid addition salts.
Claim 2
Dependent Claim
222 words
A compound of the formula: ##STR7## in which D is hydrogen or R 1 R 2 N(CH 2 ) m --, R 1 and R 2 are hydrogen, lower alkyl, phenyl(lower alkyl) or R 1 and R 2 taken together with the nitrogen atom shown can form a pyrrolidino or piperidino group, m is from 1 to 6, X is oxygen or sulphur, Y is sulphur, oxygen or methylene, n is 2 or 3, Z is hydrogen or lower alkyl, A is C 1 -C 5 alkylene or --(CH 2 ) p W(CH 2 ) q -- where W is oxygen or sulphur and p and q are such that their sum is from 1 to 4, and B is hydrogen, methyl, C 3 -C 6 cycloalkyl, a heteroaryl group selected from furyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, imidazolyl, thiadiazolyl, benzimidazolyl and benzthiazolyl, said heteroaryl group being optionally substituted by one or more of the groups lower alkyl, lower alkoxy, halo, hydroxy and amino, or B is a naphthyl, or a 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 alkoxylower alkoxy, trifluoromethyl, di(lower alkyl)amino, phenoxy, halophenoxy, lower alkoxyphenoxy, phenyl, halophenyl or lower alkoxyphenyl groups, in the form of the free base or its pharmaceutically acceptable acid addition salts.
Claim 3
Dependent Claim
38 words
A compound of claim 1 in which R 1 and R 2 are hydrogen, lower alkyl or 2-phenylethyl or R 1 and R 2 taken together with the nitrogen atom shown can form a pyrrolidino or piperidino group.
Claim 4
Dependent Claim
15 words
A compound of claim 2 in which R 1 and R 2 are both methyl.
Claim 5
Dependent Claim
15 words
A compound of claims 1, 2 or 3 in which m is 1 to 3.
Claim 6
Dependent Claim
10 words
A compound of claim 1 in which D is hydrogen.
Claim 7
Dependent Claim
10 words
A compound of claim 1 in which X is oxygen.
Claim 8
Dependent Claim
12 words
A compound of claim 1 in which Y is sulphur or methylene.
Claim 9
Dependent Claim
10 words
A compound of claim 1 in which Y is sulphur.
Claim 10
Dependent Claim
10 words
A compound of claim 1 in which n is 2.
Claim 11
Dependent Claim
10 words
A compound of claim 1 in which Z is methyl.
Claim 12
Dependent Claim
10 words
A compound of claim 1 in which Z is hydrogen.
Claim 13
Dependent Claim
11 words
A compound of claim 1 in which A is α,ω-straight alkylene.
Claim 14
Dependent Claim
10 words
A compound of claim 12 in which A is methylene.
Claim 15
Dependent Claim
29 words
A compound of claim 1 in which A is --(CH 2 ) p W(CH 2 ) q -- where p is 0, W is oxygen and q is 1.
Claim 16
Dependent Claim
31 words
A compound of claim 1 in which B is a 2-furyl, 2-thienyl, 2-thiazolyl or 2-imidazolyl group, which group is optionally substituted by one or more lower alkyl or lower alkoxy groups.
Claim 17
Dependent Claim
14 words
A compound of claim 1 in which B is a 5-(1,3-benzodioxolyl) or 1-naphthyl group.
Claim 18
Dependent Claim
20 words
A compound of claim 1 in which B is a phenyl group substituted by one or more lower alkoxy groups.
Claim 19
Dependent Claim
13 words
A compound of claim 17 in which B is 3-methoxyphenyl, 4-methoxyphenyl or 3,4-dimethoxyphenyl.
Claim 20
Dependent Claim
9 words
The compound of claim 16, said compound being 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-[5-(1,3-benzodioxolyl)methyl]-4-pyrimidone.
Claim 21
Dependent Claim
31 words
A pharmaceutical composition having histamine H 2 -receptor blocking activity comprising in an effective amount to block said receptors a compound of claim 1 and a pharmaceutically acceptable diluent or carrier.
Claim 22
Dependent Claim
30 words
A method of blocking histamine H 2 -receptors which comprises administering to an animal in need thereof in an effective amount to block said receptors a compound of claim 1.
Claim 23
Dependent Claim
36 words
A method of simultaneously blocking histamine H 1 -receptors and histamine H 2 -receptors which comprises administering to an animal in need thereof in an effective amount to block said receptors a compound of claim 5.
Claim 24
Dependent Claim
42 words
A compound of claim 1 in which B is a heteroaryl group selected from furyl, thienyl, thiazolyl, oxazolyl, isothiazolyl, imidazolyl, thiadiazolyl, benzimidazolyl or benzthiazolyl, which group is optionally substituted by one or more lower alkyl, lower alkoxy, halo, hydroxy or amino groups.
Claim 25
Dependent Claim
3 words
The compound 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(4-chlorophenylmethyl)-4-pyrimidone.
Claim 26
Dependent Claim
3 words
The compound 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-5-(4-chlorophenylmethyl)-4-pyrimidone.
Claim 27
Dependent Claim
42 words
A compound of the formula: ##STR8## in which: R 1 R 2 N is a methylamino or dimethylamino group; m is from 1 to 4; Y is sulphur or methylene; and B is 5-(1,3-benzodioxolyl) or phenyl substituted by lower alkoxy or halogen.
Claim 28
Dependent Claim
42 words
A compound of the formula: ##STR8## in which: R 1 R 2 N is a methylamino or dimethylamino group; m is from 1 to 4; Y is sulphur or methylene; and B is 5-(1,3-benzodioxolyl) or phenyl substituted by lower alkoxy or halogen.
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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) | 1988-09-02 | 1989-03-04 | 1989-09-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-02 | 1993-03-04 | 1993-09-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-02 | 1997-03-04 | 1997-09-03 | $7700.00 | Window Closed / Lapsed |