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Isoureas and isothioureas

Assignee: Smith Kline & French Laboratories Ltd
•
Filing: 1981-08-06
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Granted: 1984-03-27
•
Expires: 2001-08-06
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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 01:10
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.

References Cited (Backward Citations)

US3980781A Cited
GB1223686A Cited
US3932644A Cited
US4145546A Cited
US4218452A Cited
US4084001A Cited
US4154834A Cited
US4234588A Cited
US4305945A Cited

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

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