GB1090609A — Substituted phenyl-acetonitriles

USPTO Abstract

The invention comprises compounds of the formula <FORM:1090609/C2/1> where R is an alkyl or alkenyl radical having 1 to 5 carbon atoms; R1 is an alkyl radical having 1 to 5 carbon atoms, a saturated or unsaturated, cyclic or bicyclic hydrocarbon radical, the benzyl or phenyl radical or the group <FORM:1090609/C2/2> where X is zero or one, and A, B, C, A1, B1, C1, A11, B11 and C11 represent hydrogen or halogen atoms, alkoxy or alkyl radicals having 1 to 3 carbon atoms, or wherein at least two of the adjacent substituents A to C1, A1 to C1 and A11 to C11 together form a methylene dioxy group with the proviso that at least one of these substituents A to C11 is the trifluoromethyl radical, and n is an integer from 2 to 4 and m is an integer from 1 to 3 with the further proviso that the trifluoromethyl radical is linked at a position other than the ortho position. The novel compounds may be made by reacting an appropriate phenyl acetonitrile (A)(B)(C)Ph.CH(R1)CN with <FORM:1090609/C2/3> where X is a reactive acid residue, preferably a halogen, in the presence of a basic condensation agent; by reacting a compound of same formula as the desired product but where R1 is hydrogen with a compound R1-X; by condensing (A)(B)(C)Ph.CH2CN with R1-X and with <FORM:1090609/C2/4> in any order; by reacting (A)(B)(C)Ph.C(R1)(CN).(CH2)n.X with HN(R)(CH2)m.Ph(A1(B1)(C1) or with H2N(CH2)mPh(A1(B1(C1) followed by alkylation to introduce R. The preparation of the following starting material is also described: a -isopropyl-3-trifluoromethyl phenyl acetonitrile from 3-trifluoromethylphenyl acetonitrile and isopropyl bromide; a - [(N - methyl - N - homoveratryl) - g -aminopropyl] - 3 - trifluoromethyl phenyl acetonitrile from 3-trifluoromethyl phenylacetonitrile and N-methyl-N-homoveratryl amino - g - chloropropane; a - isopropyl - a - (31-chloropropyl) - 3 - trifluoromethyl phenyl acetonitrile from 1-chloro-3-bromopropane or 1,3-dichloropropane with a -isopropyl-3-trifluoromethyl phenylacetonitrile. Pharmaceutical compositions comprise the compouds of Formula I and an inert carrier. The compositions may be used for the treatment of coronary disturbances and for combating bacterial protozoal, viral, helmintic or fungal pathogens. They may be administered orally in the form of tablets, pills, powders, capsules, solutions, emulsions, suspensions or dispersions; by intravenous or intramuscular injection or by rectal application in the form of suppositories.