Abstract:
4-PHENYL-8-AMINO TETRAHYDROISOQUINOLINES HAVING CENTRALLY STIMULATING AND THYMOLEPTIC ACTION. METHODS FOR THEIR MANUFACTURE BY RING CLOSURE, ACYLATION, OR REDUCTION. PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS.
IN WHICH R AND R1 ARE HYDROGEN, CHLORINE, BROMINE, HYDROXYL, ALKYL OF 1 TO 3 CARBON ATOMS, OR ALKOXY OF 1 TO 3 CARBON ATOMS, AND R4 IS HYDROGEN OR METHOXY HAVING BENEFICIAL PHYSIOLOGICAL ACTIVITY IN THE TREATMENT OF HEART AND CIRCULATORY DISEASES.
Abstract:
1,193,657. Substituted phenylacetamides. FARBWERKE HOECHST A.G. 11 Aug., 1967 [13 Aug., 1966], No. 37048/67. Heading C2C. Novel substituted phenylacetamides of the formula in which R 1 , R 2 and R 3 each represent an identical or different, saturated or unsaturated aliphatic hydrocarbon radical containing up to 4 carbon atoms are prepared by one of the following methods (a) Hydrolysis of an appropriately substituted phenylacetonitrile. (b) Reaction of ammonia on a suitably substituted phenylacetic acid or derivative thereof. (c) Dehydration of an ammonium salt of an appropriately substituted phenylacetic acid. (d) Hydrogenolysis of a suitably substituted N-benzyl- or N,N-dibenzyl-phenylacetamide. (e)Alkylation or alkenylation of an appropriately substituted 3-hydroxy-phenylacetamide. 3 - Hydroxyphenyldiethylacetamide is made by treating 3 - methoxyphenyldiethylacetamide with hydrobromic acid. 3 - Methoxyphenyldipropylacetonitrile is obtained by treating 3-methoxybenzyl cyanide with propyl bromide in the presence of sodium amide. Similarly using sec. butyl bromide, 3 - methoxyphenyl - ethyl - sec. butyl - acetonitrile is obtained from 3 - methoxy - phenyl - ethyl - acetonitrile which is in turn, obtained from 3- methoxybenzyl cyanide and ethyl bromide. Therapeutic compositions, having sedative properties and suitable for oral or parenteral administration, contain the above novel compounds as the active ingredient and pharmaceutically acceptable carriers.