Azaspiroalkanediones, process for preparing the same and Pharmaceutical Compositions comprising the same

摘要

1,164,503. Azaspiroalkanedione derivatives. MEAD JOHNSON & CO. 26 Jan., 1967 [1 Feb., 1966], No. 4000/67. Heading C2C. Novel compounds of general formula and acid addition salts thereof; wherein n is 4 or 5, R1 and R2 are H or CH 3 , R3, R4 and R6 are H, C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio, amino, halogen, CF 3 , NO 2 , alkanamido or alkylsulphonamido and A is C 2-6 alkylene or C 4-6 oxyalkylene in which the oxygen atom is not linked to either of the N atoms which A joins; are prepared either by reaction of an anhydride of Formula II and an amine of Formula III or by reaction of an azaspiroalkanedione derivative of Formula IV wherein X is a reactive ester group and a N- phenylpiperazine of Formula V optionally followed by reduction of NO 2 to NH 2 , acylation of an NH 2 group and/or salt formation. 1 - (# - Aminoalkyl) - 4 - phenylpiperazines of Formula III above are prepared by reduction of the corresponding nitriles which are obtained by reaction of a phenyl piperazine and a haloalkylnitrile. Reactive ester derivatives of Formula IV above are prepared from the corresponding alcohols (IV, X = OH) which are prepared by reaction of amino alcohols with the spiro anhydrides of Formula II. 1 - Alkylsulphonamidophenyl) piperazine is prepared by decarboxylation of the 1-(alkylsulphonamidophenyl)- 4 - carbethoxy - piperazine obtained by acylation of the corresponding aminophenyl compound which is prepared by reduction of the nitro compound which is obtained by condensation of a nitrohalobenzene and a N-carbethoxypiperazine. Pharmaceutical compositions in conventional forms for oral, rectal and parenteral administration comprise an above novel compound or a salt thereof and an excipient and are psychotropic, anti-allergic or anti-inflammatory agents, anti-emetics, capillary protectants, analgetics and centrally acting muscle relaxants.