Neue heterocyclische AEther und Verfahren zu ihrer Herstellung

摘要

1320395 Heterocyclic ethers of 1-substituted- 4-hydroxyalkylpiperazines FARBWERKE HOECHST AG 14 Sept 1970 [12 Sept 1969] 43754/70 Heading C2C A novel heterocyclic ether of the general Formula I wherein R 1 is a pyrimidinyl (2), pyrimidinyl- (4), pyridyl-(2), pyridyl-(3), pyridyl-(4), pyrazinyl-(3), pyridazinyl-(6), quinolyl-(2), quinazolinyl-(4), quinoxalinyl-(3), 1,2-dihydro-phthalazinyl-(4), thiazolyl-(2) or a benzthiazolyl-(2) radical which may be substituted in the heterocyclic ring by one or more of the same or different substituent selected from C 1-6 alkyl, C 1 or C 2 alkoxy, phenyl, C 1-2 alkyl, phenyl, C 1-2 alkyl substituted phenyl and oxo groups; R 2 is phenyl optionally substituted by one or more of the same or different substituents selected from C 1-6 alkyl, C 1-2 alkoxy, chlorine or bromine and which optionally contains one or two nitrogen atoms in the ring; and A represents a C 2-6 alkylene radical and physiologically tolerable acid addition salts may be prepared by (a) reacting an R 1 halide with an appropriately substituted 1-hydroxyalkyl-piperidine, (b) reacting a metal salt of R 1 OH with a reactive ester of a suitably substituted 1-hydroxyalkyl piperidine, (c) reducing an acyl group to form A in I, (d) reacting YNH 2 with a compound VIII wherein one of Y and Z represents R 2 while the other represents R 1 OA-, (e) reacting with a reactive ester of ethylene glycol. The starting material of process (c) may be prepared by reacting R 2 substituted piperidine with a chloroalkyl carboxylic halide and condensing the product with a metallic salt of R 1 OH. The reactive ester in (b) may be formed from the free hydroxy compound. Pharmaceutical compositions of the compound I with the usual excipients show α-sympatholytic activity when administered orally or parenterally.