Method of preparation of the new derivatives of the phenylisopropylamine

摘要

The invention relates to phenylisopropylamine derivatives of the general formula FORM:1121857/C2/1 in which X1 and X2 each represent a hydrogen atom, a halogen atom, or a halogenomethyl group, at least one of them being other than hydrogen and R represents an unsaturated aliphatic hydrocarbon radical containing from 3 to 8 carbon atoms, e.g. an allyl, methylallyl, butenyl, propargyl or 3-butynyl radical. Preferably at least one of X1 and X2 represents a trifluoromethyl group. Isopropylamines claimed per se are those of:- N - (2 - propyne 1 - yl) beta - (m - trifluoromethylphenyl); N - (2 - propyne 1 - yl)beta(p - fluorophenyl); N - (2 - propyne 1 - yl) beta - (3,4 - dichlorophenyl); N - (2 - propyne 1 - yl)beta - (2 - trifluoromethyl - 4 - fluorophenyl); N - (2 - propyne 1 - yl)beta - (3,5-bis - trifluoromethylphenyl); d-N-(2-propyne 1 - yl)beta - (m - trifluoromethylphenyl); 1 - N - (2 - propyne 1 - yl)beta - (m - trifluoromethylphenyl); N - (2 - propene 1 - yl)beta-(m - trifluoromethylphenyl); d - N - (2 - propene 1 - yl)beta - (m - trifluoromethylphenyl); 1 - N - (2 - propene 1 - yl)beta - (m - trifluoromethylphenyl); N - (2 - butene 1 - yl)beta(m - trifluoromethylphenyl); N - (2 - methylpropene 1 - yl)beta - (m - trifluoromethylphenyl); N - (3 - methyl - 2 - butene 1 - yl) beta - (m - trifluoromethylphenyl); N - (2-propene 1 - yl)beta - (3,4 - dichlorophenyl) and N - (4 - pentyne 1 - yl)beta - (m - trifluoromethylphenyl). The compounds may be prepared by refluxing an appropriately substituted primary phenylisopropylamine with a haloalkene or haloalkyne containing 3 to 8 carbon atoms, in an inert solvent, if desired in the presence of a hydrohalic acid acceptor. The optical isomers may be obtained by using the corresponding d or 1 phenylisopropylamine as starting material or by resolving the racemic derivative of the compound by means of an optically active acid. Many examples are given.ALSO:A pharmaceutical preparation comprises as active ingredient a phenylisopropylamine derivative of the general formula: FORM:1121857/A5-A6/1 in which X1 and X2 each represent a hydrogen atom, a halogen atom, or a halogenomethyl group, at least one of them being other than hydrogen, and R represents an unsaturated aliphatic hydrocarbon radical containing from 3 to 8 carbon atoms, e.g. an allyl, methylallyl, butenyl, propargyl or 3-butynyl radical. In admixture or conjunction with a pharmaceutically suitable carrier. Preferably at least one of X1 and X2 is a trifluoromethyl group and the composition preferably contains from 10 to 100 milligrammes of active ingredient in dosage unit form. The preparations are useful as analgesics, anorexitenics, metabolism and central nervous system activity regulators or as hypotensives.