Antisecretory branched chain heterocyclic derivatives,...

C - Chemistry – Metallurgy – 07 – D

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C07D 417/12 (2006.01) C07D 209/48 (2006.01) C07D 277/14 (2006.01) C07D 277/48 (2006.01)

Patent

CA 1140925

ABSTRACT OF THE DISCLOSURE The invention relates to a heterocyclic derivative of tho formula: Image I in which D io O, S or NH; E is CH or when D io O or S, E is N; Y is S, O, CH2, SO or a direct bond: P is a direct bond or C(1-4)unbranched alkylene optionally substituted by 1 or 2 C(1-4)alkyls and Q is C(1-4)unbranched alkylene optionally sub- stituted by 1 or 2 C(1-4)alkyls, provided total number of alkyls in F and Q is 1 or 2, that when Y is S, O or SO, P is alkylene and that when Y is O or SO, Q is C(2-4)alkylene; R1 is H or C(1-10)alkyl; A is 3,4-dioxocyclobuten-1,2-diyl or C=Z where Z is S, O, NCN, NNO2, CHNO2, NCONH2, C(CN)2, NCOR2, NCO2R2, NSO2R2 or NR3 where R3 is C(1-6)alkyl or C(6-12)- aryl and R3 is H or C(1-6)alkyl: B is C(1-6)alkoxy, C(1-6)alkyl- thio or NR4R5 where R4 and R5 are H, C(1-10)alkyl, C(3-6)alkenyl, C(3-6)alkynyl, C(2-6)(primary OH)alkyl, C(2-6)(primary NH2)- alkyl, C(3-6)cycloalkyl, or R4 and R5 together are 5- or 6- membered satured ring which may contain an additional O or NH; and the salts thereof. The compounds of the invention are histamine H-2 antagonists which inhibit gastric acid secretion. The compounds are particularly distinguished by the presence of branching in the side-chain together with a pendant guadidino group.

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