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US4159329A Expired / Lapsed US ⏱️ 0.0 years remaining

4-Pyrimidones compositions, and methods of use

Assignee: Smith Kline & French Laboratories Ltd
•
Filing: 1977-12-15
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Granted: 1979-06-26
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Expires: 1997-12-15
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Abstract

Abstract The compounds are substituted isocytosines which are histamine H2-antagonists. Two specific compounds of the present invention are 2-[2-(5-methyl-4-imidazolylmethylthio)-ethylamino]-5-(3-methoxybenzyl) -4-pyrimidone and 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-6-benzyloxy-4-pyrimi done.

Inventors

  • 👤 Thomas H. Brown
  • 👤 Graham J. Durant
  • 👤 John C. Emmett
  • 👤 Charon R. Ganellin

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 15:50
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/60; C07D239/66; C07D239/68; C07D239/56

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 163 words
A compound of the formula: ##STR11## wherein Het' is a 2- or 4-imidazolyl ring optionally monosubstituted by lowr alkyl, halogen, trifluoromethyl or hydroxymethyl, a 2-pyridyl ring optionally monosubstituted by lower alkyl, lower alkoxy, halogen, amino or hydroxy, a 2-pyridyl ring which is disubstituted by lower alkoxy groups, or which has a phenyl, carbocyclic or cyclic either ring containing two oxygen atoms fused to it, a 2-thiazolyl ring, a 3-isothiazolyl ring optionally monosubstituted by chlorine or bromine, a 3-(1,2,5)-thiadiazolyl ring optionally monosubstituted by chlorine or bromine, a 2-(5-amino-1,3,4-thiadiazolyl)ring; Z is sulphur or a methylene group; X is oxygen or sulphur; W is methylene, oxygen or sulphur; m and n are such that their sum is from 1 to 4 when W is oxygen or sulphur, or from 0 to 4 when W is methylene; A is a 1- or 2-naphthyl ring or a phenyl ring substituted with one lower alkyl group; and Y 3 is hydrogen; or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim 163 words
A compound of the formula: ##STR11## wherein Het' is a 2- or 4-imidazolyl ring optionally monosubstituted by lowr alkyl, halogen, trifluoromethyl or hydroxymethyl, a 2-pyridyl ring optionally monosubstituted by lower alkyl, lower alkoxy, halogen, amino or hydroxy, a 2-pyridyl ring which is disubstituted by lower alkoxy groups, or which has a phenyl, carbocyclic or cyclic either ring containing two oxygen atoms fused to it, a 2-thiazolyl ring, a 3-isothiazolyl ring optionally monosubstituted by chlorine or bromine, a 3-(1,2,5)-thiadiazolyl ring optionally monosubstituted by chlorine or bromine, a 2-(5-amino-1,3,4-thiadiazolyl)ring; Z is sulphur or a methylene group; X is oxygen or sulphur; W is methylene, oxygen or sulphur; m and n are such that their sum is from 1 to 4 when W is oxygen or sulphur, or from 0 to 4 when W is methylene; A is a 1- or 2-naphthyl ring or a phenyl ring substituted with one lower alkyl group; and Y 3 is hydrogen; or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim 18 words
A compound of claim 1 wherein Het' is a 2-thiazolyl, 5-methyl-4-imidazolyl, 5-bromo-4-imidazolyl, 3-bromo-2-pyridyl, 3-chloro-2-pyridyl, 3-methoxy-2-pyridyl or 3-hydroxy2-pyridyl ring.
Claim 4
Dependent Claim 9 words
A compound of claim 1 wherein Z is sulphur.
Claim 5
Dependent Claim 9 words
A compound of claim 1 wherein X is oxygen.
Claim 6
Dependent Claim 15 words
A compound of claim 1 wherein m and n are O and W is methylene.
Claim 7
Dependent Claim 16 words
A compound of claim 1 wherein m is O, n is 1 and W is methylene.
Claim 8
Dependent Claim 9 words
A compound of claim 1, said compound being 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(1-naphthylmethyl)-4-pyrimidone.
Claim 9
Dependent Claim 35 words
A compound of claim 1 wherein Het' is a 2-pyridyl ring which is disubstituted by lower alkoxy groups or which has a phenyl, carbocyclic or cyclic ether ring containing two oxygen atoms fused to it.
Claim 10
Dependent Claim 9 words
A compound of claim 8, said compound being 2-[2-(3,4-dimethoxy-2-pyridylmethylthio)ethylamino]-5-(4-methoxybenzyl)-4-pyrimidone.
Claim 11
Dependent Claim 10 words
A compound of claim 1, said compound being 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(4-methylbenzyl)-4-pyrimidone dihydrochloride.
Claim 12
Dependent Claim 9 words
A compound of claim 1, said compound being 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(3-methylbenzyl)-4-pyrimidone.
Claim 13
Dependent Claim 10 words
A compound of claim 1, said compound being 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(3-methylbenzyl)-4-pyrimidone dihydrochloride.
Claim 14
Dependent Claim 9 words
A compound of claim 1, said compound being 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(4-methylbenzyl)-4-pyrimidone.
Claim 15
Dependent Claim 30 words
A pharmaceutical composition to block histamine H 2 -receptors comprising, in an effective amount to block said receptors, a compound of claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 16
Independent Claim 216 words
A method of simultaneously blocking histamine H 1 -receptors and histamine H 2 -receptors which comprises administering to an animal in need thereof an effective amount of a compound of the formula: ##STR12## wherein Het' is a 2- or 4-imidazolyl ring optionally monosubstituted by lower alkyl, halogen, trifluoromethyl or hydroxymethyl, a 2-pyridyl ring optionally monosubstituted by lower alkyl, lower alkoxy, halogen, amino or hydroxy, a 2-pyridyl ring which is disubstituted by lower alkoxy groups, or which has a phenyl, carbocyclic or cyclic ether ring containing two oxygen atoms fused to it, a 2-thiazolyl ring, a 3-isothiazolyl ring optionally monosubstituted by chlorine or bromine, a 3-(1,2,5-)-thiadiazolyl ring optionally monosubstituted by chlorine or bromine, or a 2-(5-amino-1,3,4-thiadiazolyl)ring; Z is sulphur or a methylene group; X is oxygen or sulphur; W is methylene, oxygen or sulphur; m and n are such that their sum is from 1 to 4 when W is oxygen or sulphur, or from 0 to 4 when W is methylene; A is a 1- or 2-naphthyl ring, a phenyl ring substituted with one lower alkyl group and when --(CH 2 ) m --W(CH 2 ) n --is an alkylene group other than a methylene group, A may also be phenyl; and Y is hydrogen or lower alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 17
Independent Claim 216 words
A method of simultaneously blocking histamine H 1 -receptors and histamine H 2 -receptors which comprises administering to an animal in need thereof an effective amount of a compound of the formula: ##STR12## wherein Het' is a 2- or 4-imidazolyl ring optionally monosubstituted by lower alkyl, halogen, trifluoromethyl or hydroxymethyl, a 2-pyridyl ring optionally monosubstituted by lower alkyl, lower alkoxy, halogen, amino or hydroxy, a 2-pyridyl ring which is disubstituted by lower alkoxy groups, or which has a phenyl, carbocyclic or cyclic ether ring containing two oxygen atoms fused to it, a 2-thiazolyl ring, a 3-isothiazolyl ring optionally monosubstituted by chlorine or bromine, a 3-(1,2,5-)-thiadiazolyl ring optionally monosubstituted by chlorine or bromine, or a 2-(5-amino-1,3,4-thiadiazolyl)ring; Z is sulphur or a methylene group; X is oxygen or sulphur; W is methylene, oxygen or sulphur; m and n are such that their sum is from 1 to 4 when W is oxygen or sulphur, or from 0 to 4 when W is methylene; A is a 1- or 2-naphthyl ring, a phenyl ring substituted with one lower alkyl group and when --(CH 2 ) m --W(CH 2 ) n --is an alkylene group other than a methylene group, A may also be phenyl; and Y is hydrogen or lower alkyl; or a pharmaceutically acceptable acid addition salt thereof.
Claim 18
Dependent Claim 26 words
A method of blocking histamine H 2 -receptors which comprises administering to an animal in need thereof an effective amount of a compound of claim 1.

References Cited (Backward Citations)

BE814032A Cited
US3932644A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-06-25 1982-12-25 1983-06-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-06-25 1986-12-25 1987-06-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-06-25 1990-12-25 1991-06-26 $7700.00 Window Closed / Lapsed

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