Patent ES-253916-A1 (ES)
Title: 9-(propene-3-ylidene-1), and 9-[3'-(nu-hydrox-yalkylpiperazino-nu)-propylidene], xanthenes and thiaxanthenes, and processes for their preparation
IPC: C07D311/90
Filed: 1959-12-03
Abstract: The invention comprises: (a) compounds of the general formula <FORM:0932494/IV(a)/1> (wherein X represents an oxygen or sulphur atom, R and Y may be the same or different and each represents a hydrogen or halogen atom or a lower-alkoxy or lower-alkylmercapto group, and Z represents a hydrogen atom or a lower alkanoyl radical, the term "lower" indicating a maximum of 8 carbon atoms in the radicals so qualified) and their acid addition salts (b) the preparation of compounds of the general formula <FORM:0932494/IV(a)/2> (wherein X, R and Y have the meanings given in (a) and <FORM:0932494/IV(a)/3> is a methylamino, dimethylamino, morpholino, thiamorpholino, pyrrolidino, piperidino, piperazino, N1-lower-alkylpiperazino, N1-hydroxy-lower-alkylpiperazino or N1-lower-alkanoyloxy-lower-alkylpiperazino radical), or their acid addition salts, by reacting a compound of the general formula <FORM:0932494/IV(a)/4> with an amine HNR1R2 (c) the combination of process (b) with the preparation of the starting materials by treating a compound of the general formula <FORM:0932494/IV(a)/5> with a dehydrating agent and (d) treatment of compounds obtained according to (c), when <FORM:0932494/IV(a)/6> is an N1-unsubstituted piperazino group, with a lower-alkylating, hydroxy-lower-alkylating or lower-alkanoyloxyalkylating agent. Reference is also made to esterification of the hydroxyalkylated compounds. Some of the products may be separated into cis- and trans-isomers. The products, especially compounds (a), are useful in pharmacy (see Group VI). Xanthenols and thiaxanthenols of the last general formula above are prepared by reacting the corresponding xanthones or thiaxanthones with an allyl magnesium halide in ether and hydrolysing the resulting magnesium complex. 2-Methylmercapto- and 2-n-butylmercaptothiaxanthone are prepared by warming o,o1-diphenyl disulphide dicarboxylic acid with thioanisole or n-butyl phenyl sulphide in concentrated sulphuric acid. 2,7-Dichlorothiaxanthone is prepared by chlorinating 2-chlorothiaxanthone in glacial acetic acid. Specifications 829,763, 862,200, 896,036 and 896,037 are referred to.ALSO:Xanthene and thiaxanthene derivatives of the general formula <FORM:0932494/VI/1> (wherein X represents an oxygen or sulphur atom, R and Y may be the same or different and each represents a hydrogen or halogen atom or a lower-alkoxy or lower-alkylmercapto group, and <FORM:0932494/VI/2> represents a methylamino, dimethylamino, morpholino, thiamorpholino, pyrrolidino, piperidino, piperazino, N1 - lower - alkylpiperazino or especially an N1-hydroxy-lower-alkylpiperazino or N1-lower-alkanoyloxy-lower-alkylpiperazino radical) and their acid addition salts are useful as central nervous system depressants, antiemetic, sedative hypothermic, hypotensive and spasmolytic agents, and for potentiating and prolonging the action of barbiturates and analgesics. Specified salts include ascorbates. Specifications 829,763, 862,200, 896,036 and 896,037 are referred to.