Alcohol derivatives as histamine h-2 receptor antagonists

C - Chemistry – Metallurgy – 07 – D

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C07D 231/38 (2006.01) C07D 213/76 (2006.01) C07D 231/40 (2006.01) C07D 239/28 (2006.01) C07D 239/42 (2006.01) C07D 239/46 (2006.01) C07D 239/48 (2006.01) C07D 241/20 (2006.01) C07D 249/04 (2006.01) C07D 249/06 (2006.01) C07D 249/14 (2006.01) C07D 277/48 (2006.01)

Patent

CA 1200550

ABSTRACT ALCOHOL DERIVATIVES This invention relates to alcohol derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I:- Image I in which R1 and R2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R1 and R2 is halogen-substituted, or R2 is hydrogen and R1 is R5-E-W- in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyl, E is O, S, SO, SO2 or NR6 in which R6 is H or 1-6C alkyl, R5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R5 and R6 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R2 is hydrogen and R1 is hydrogen or 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C arylalkyl or 7-11C aroyl, the aryl, arylalkyl and aroyl radicals being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene into which is optionally inserted one or two groups; D is oxygen or sulphur; R3, R4 and R5 are hydrogen or a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.

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