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Pub. No.:    WO/1980/000966    International Application No.:    PCT/GB1979/000184
Publication Date: 15.05.1980 International Filing Date: 08.11.1979
C07D 239/46 (2006.01)
Priority Data:
7844260 13.11.1978 GB
Abstract: front page image
(EN)New histamine H2-antagonist compounds of structure 1 (FORMULA) in which R1 is hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen trifluoromethyl, nitro, amino, lower alkylamino, lower alkanoylamino, di (lower alkyl) amino or cyano; R2 is in the 3-, 4- or 5-position and is hydrogen, R2 is lower alkyl substituted by amino, lower alkylamino, di (lower alkyl) amino, N-piperidino or N-pyrollidino, or R2 is ethoxy or propoxy (Alpha)-substituted by amino, lower alkylamino, di (lower alkyl) amino, N-piperidino or N-pyrollidino; Y is methylene or oxygen and X is methylene or sulphur provided that one or two of the groups X and Y is methylene; Z is hydrogen or lower alkyl; A is C1-C5 alkylene or -(CH2)pW-(CH2)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, C3-C6 cycloalkyl, a heteroaryl group optionally substituted by one or more of the groups lower alkyl, lower alkoxy, halo, hydroxy and amino, or B is naphthyl, 6-(2,3-dihydro-1,4-benzodioxinyl), a4- or 5-(1,3-benzodioxolyl) group, or a phenyl group optionally substituted with one or more lower alkyl, lower alkoxy, halogen, aryl (lower alkoxy), hydroxy, lower alkoxy-lower alkoxy, trifluoromethyl, di (lower alkyl) amino, phenoxy, halophenoxy, lower alkoxyphenoxy, phenyl, halophenyl or lower alkoxyphenyl groups and pharmaceutical compositions containing them. A compound of structure 1 can be prepared by reacting a compound of structure 3 in which Q is nitroamino, loweralkylthio, benzylthio or halogen with an amine of structure 2, in which (FORMULA) R3 is in the 3-, 4- or 5-position and is hydrogen, lower alkyl substituted by a group R4, or is R4CH2CH2O-or R4CH2CH2CH2O-, where R4 is di(lower alkyl)amino, N-piperidino, N-pyrrollidino, a protected amino group or a protected lower alkylamino group, and where necessary any amino-protecting group present in the substituent R3 is removed.
(FR)Nouveaux composes antagonistes des recepteurs-H2 de l"histamine, de structure 1 (FORMULE) dans laquelle R1 represente l"hydrogene, un groupe alkyle inferieur, alkoxy inferieur, hydroxy, halogene, trifluoromethyle, nitro, amino, alkylamino inferieur alcanoylamino inferieur, di(alkyle inferieur) aminoe ou cyano; R2 se trouve en position 3-, 4-, ou 5- et represente l"hydrogene ou R2 represente un groupe alkyle inferieur substitue par amino, alkylamino inferieur, di(alkyle inferieur) amino, N-piperidino ou N-pyrrolidino, ou R2 represente un groupe ethoxy ou propoxy (Alpha)-substitue par amino, alkylamino inferieur, di(alkyle inferieur) amino, N-piperidino ou N-pyrrolidino; Y represente un groupe methylene ou l"oxygene et X represente un methylene; Z represente l"hydrogene ou un groupe alkyle inferieur; A represente un groupe alkylene en C1-C5 ou -(CH2)pW-(CH2)q dans lequel W represente l"oxygene ou le soufre et p et q sont tels que leur somme est de 1 a 4, et B represente l"hydrogene, un groupe methyle, cycloalkyle en C3-C6, un groupe heteroaryle facultativement substitue par un ou plus des groupes alkyle inferieurs, alkoxy inferieurs, halo, hydroxy et amino ou B represente un groupe naphtyle, 6-(2,3-dihydro-1,4-benzodioxinyl), un groupe 4- ou 5-(1,3-benzodioxolyl) ou un groupe phenyle facultativement substitue par un ou plus d"un groupe alkyle inferieur, alkoxy inferieur, halogene, aryl (alkoxy inferieur), hydroxy, alkoxy inferieur-alkoxy inferieur, trifluoromethyl, di(alkyle inferieur) amino, phenoxy, halophenoxy, alkoxy inferieur phenoxy, phenyle, alophenyl ou groupes alkoxy inferieur phenyle et les compositions pharmaceutiques les contenant. Un compose de structure 1 peut etre prepare en faisant reagir un compose de structure 3 dans laquelle Q represente un groupe nitroamino, thio-alkyle inferieur, benzylthio ou un halogene avec une amine de structure 2 dans laquelle (FORMULE) R3 est en position 3-, 4- ou 5- et represente l"hydrogene, un groupe alkyl inferieur substitue par un groupe R4 ou represente un groupe R4CH2CH2O- ou R4CH2CH2CH2O- dans lequel R4 represente un groupe di(alkyle inferieur) amino, N-piperidino, N-pyrrolidino, un groupe amino protege ou un groupe akylamino inferieur protege et si necessaire, tout groupe protecteur de groupe amine present dans le substituent R3 est elimine.
Designated States:
Publication Language: English (EN)
Filing Language: English (EN)