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1409865 Dihydropyridine derivatives SCIENCE UNION ET CIE SOC FRANCAISE DE RECHERCHE MEDICALE 12 Feb 1974 [13 Feb 1973] 7037/73 Heading C2C Novel compounds of Formula I R 1 and R 2 , which may be the same or different, each is a lower alkyl radical which may carry one or more substituents selected from halogen atoms, hydroxyl, lower alkoxy, lower alkoxylower alkoxy, amino, lower alkylamino, dilower alkylamino and N,N-alkyleneamino radicals, each R 3 is a lower alkyl radical, R 4 is a hydrogen atom or an alkyl radical containing from 1 to 3 carbon atoms which may be substituted by one or more hydroxy and/or optionally substituted amino groups, and X is a radical of the Formula II in which the Hal substituents, which may be the same or different, each is a fluorine chlorine, bromine or iodine atom, or X is a radical of the Formula III in which R 5 is a cyclopropyl radical, a lower alkenyl radical, a lower alkynyl radical or a radical of the formula in which A is selected from cyclopropyl, lower alkenyl, lower alkynyl, cyclopropyl-lower alkyl, aryl-lower alkenyl and halo-lower alkenyl radicals a lower alkyl-amino alkyl radical of the formula in which R 6 is hydrogen or a lower alkyl radical, R 7 is hydrogen or a lower alkyl radical, and R 8 is hydrogen or a lower alkyl radical, or R 6 and R 7 together are an alkylene chain having from 2 to 6 carbon atoms, or R 7 and R 8 together are an alkylene chain, which may include another hetero atom, having from 2 to 6 carbon atoms, with the proviso that R 7 and R 8 cannot both be hydrogen atoms, n is zero, 1 or 2, and n<SP>1</SP> is zero or an integer from one to three and " lower " denotes groups containing up to 6 carbon atoms, are prepared by one of the following methods (a) a compound X-CHO is reacted with a compound R 3 COCH 2 COOR 2 and a compound R 4 NH 2 ; (b) reacting a compound R 3 COCH 2 COOR 2 with R 4 NH 2 and then with XCHO; (c) reacting a compound XCHO with R 3 COCH 2 COOR 2 and then with or (d) by transesterification. Intermediates XCHO are prepared by etherification of salicylaldehyde. The ethylene ketal of salicylaldehyde is reacted with epichlorohydrin to give 1-(ethylendioxymethyl) - 2 - (1<SP>1</SP>,2<SP>1</SP> - epoxypropyloxy)- benzene which is reacted with t-butylamine to give 1 - (ethylenedioxymethyl) - 2 - (1<SP>1</SP> - t - butylamino - 2<SP>1</SP> - hydroxypropyloxy) - benzene which is hydrolysed to the corresponding aldehyde. Pharmaceutical compositions in conventional forms for oral, parenteral, sublingual, percutaneous or rectal administration and having anti-hypertensive, coronarodilator and vasodilator activities comprise an above novel compound and a carrier or diluent. |