Patent CA-2061629-A1 (CA)
Title: 5-(substituted amino)-1,2,4- triazolo¬1,5-a|pyrimidine derivatives
Inventor: REITER JOZSEF
IPC: C07D487/04
Filed: 1992-02-21
Abstract: 5-(SUBSTITUTED AMINO)-1, 2, 4-TRIAZOLO[1,5-a]PYRIMIDINE    DERIVATIVES     A b s t r a c t The invention relates to new 5-(substituted amino)--1,2,4-triazolo[1,5-3]pyrimidine derivatives and a process for the preparation thereof. The invention also relates to pharmaceutical compositions comprising the said compounds and to the use thereof for the treatment of diseases.          The 5-(substituted amino)-1,2,4-triazolo[1,5-a]-pyrimidines according to the invention correspond to the general Formula (I),                  (I) wherein Q     represents hydrogen or a 6-membered heterocyclic group containing one or more nitrogen and/or oxygen atom(s) optionally carrying a C1-4 alkyl substituent, or a group of the Formula S(O)pR3, wherein p  stands for 0, 1 or 2, and R3 denotes straight or branched chained C1-8 alkyl, C2-6 alkenyl or phenyl-(C1-4 alkyl), which latter may optionally carry one or more halogen or nitro substituent(s), or phenyl optionally substituted by one or more nitro or trifluoromethyl;     or a group of the Formula NR4R5, wherein R4 and R5 each represent hydrogen, straight or branched C1-12 alkyl, C2-6 alkenyl, phenyl-(C1-4 alkyl) or di-(C1-4 alkyl)-amino-(C1-6 alkyl);    R1 and R2 each represent hydrogen or straight or branched chained C1-4 alkyl, or R1 and R2 together form a group of the Formula (CH2)n-Y-(CH2)m, wherein Y stands for a CH2 group, a sulfur atom or a group of the Formula NR6, wherein R6 denotes phenyl-(C1-4 alkyl), n and m each represent 0, 1, 2, 3, 4 or 5;    Z     stands for a group of the Formula NR7R8, wherein R7 and R8 each represent hydrogen, C2-6 alkenyl, C3-8 cycloalkyl, adamantyl or phenyl-(C1-4 alkyl), which latter may optionally carry one or more substituent(s) selected from the group consisting of halogen, hydroxy, C1-4 alkyl, C1-4 alkoxy, amino and nitro; (C1-4 alkyl)-amino-(C1-6 alkyl), di-(C1-4 alkyl)-amino-(C1-6 alkyl) or C1-6 alkyl, which latter may optionally be substituted by a hydroxy, amino, carboxy, morpholinocarbonyl, [4-(2-hydroxy-ethyl)-piperazin-1-yl]-carbonyl, (C1-4 alkoxy)-car-bonyl or a 5- or 6-membered saturated or unsaturated heterocyclic group containing one or more nitrogen and/or oxygen atom(s) and being optionally condensed with a benzene ring; or R7 and R8 together form a group of the Formula (CH2)j-W-(CH2)k , wherein j and k each represent 1, 2 or 3, and W stands for oxygen or a CH2 or CHOH group or a group of the Formula NR10, wherein R10 denotes hydrogen, C1-4 alkoxycarbonyl or C1-4 alkyl, which latter may optionally carry a substituent selected from the group consisting of hydroxy or phenyl; or a group of the Formula SR9, wherein R9 stands for C1-4 alkyl substituted by a (C1-4 alkoxy)-carbonyl group, with the proviso that if Q represents hydrogen or a group of the Formula S(O)pR3, R1 and R2 are other than hydrogen or C1-4 alkyl, and possess valuable positive inotropic and antianginal effects which are complemented by acute antiinflammatory, ulcus and gastric acid secretion inhibiting, furthermore by weaker tranquillant, spasmolytic and analgesic properties.