ES264470A1 - New phenylpiperazine compounds - Google Patents

Abstract

The invention comprises compounds of general formula <FORM:0971041/C1/1> wherein X represents a straight saturated hydrocarbon chain of two to four carbon atoms which, when the chain contains four carbon atoms, may be substituted by an oxo group on the carbon atom adjacent to the phenyl groups, Ar represents a phenyl group optionally substituted by a haloalkyl (e.g. CF3-) group or halogen atom, R1 represents a meta- or para-group from amino, monoalkylamino, acylamido (including alkanesulphonamido), N-alkylacylamido, carbamoylamino, alkoxycarbonylamino, chloroalkoxycarbonylamino and N-oxazolidone groups, R2 represents a group in any unoccupied position and is a nitro group or any group within the definition of R1 except an N-oxazolidone group (alkyl, haloalkyl, acylamido and alkoxy groups have 1-4 carbons) and their acid addition salts and their preparation by reacting a compound of formula <FORM:0971041/C1/2> with a compound of formula <FORM:0971041/C1/3> wherein Y represents the acid residue of a reactive ester, and if desired converting by known methods R1 and/or R2 into different groups within those definitions. Conversions described are reduction of nitro and hydrolysis and reduction of acylamido groups to form amino and alkylamino compounds and the treatment of amino groups to yield alkylamino, acylamido, carbamoylamino, alkoxycarbonylamino and chloroalkoxycarbonylamino derivatives, forming from the last-named an N-oxazolidone derivative. Phenalkyl halides III prepared are 2-p-aminophenylethyl bromide by hydrogenation of the nitro derivative) which on acetylation and nitration yields 2-(4-acetamido-2 and 3-nitrophenyl)-ethyl bromides and on treatment with methane-sulphonyl chloride yields 2-p-methane-sulphonamido-phenylethyl bromide from which the 3-nitro-derivative is obtained also 4-p-acetamidophenyl-4-oxobutyl chloride (from acetanilide and 4-chlorobutyryl chloride) from which the 3-nitro-derivative is obtained. Pharmaceutical compositions comprise comprise compounds I or non-toxic acid addition salts thereof with a pharmaceutical carrier. Forms (tablets, pills, powders, granules, capsules, syrups, elixirs, solutions, suspensions, emulsions) are described for oral and parenteral administration. The compounds have psychotropic properties.