GB1225216A - - Google Patents

Abstract

1,225,216. 1-aminoalkyl-1-arylvinylphthalans. AMERICAN CYANAMID CO. 13 June, 1969 [26 July, 1968], No. 30191/69. Heading C2C. The invention comprises compounds of formula and their non-toxic acid addition salts, wherein R 1 -R 3 and R 5 -R 7 are H or alkyl (or R 3 is alkoxycarbonyl); R 4 is alkyl (or NR 3 R 4 may be 4-morpholinyl, polymethyleneimino, 1-piperazinyl, 1-alkyl-4-piperazinyl or 1-alkoxycarbonyl-4-piperazinyl); R 8 is thienyl, furyl, indonyl, naphthyl, alkoxynaphthyl, or phenyl (possibly substituted by cycloalkyl, halogen, alkyl, phenyl or 1-3 methoxy groups); and n is 1-3. These compounds are prepared by (a) reacting a compound of formula with one of formula halogen-MgCH 2 CHR 5 (CH 2 ) n NR 3 R 4 ; (b) [to obtain compounds where R 3 is alkoxycarbonyl or NR 3 R 4 is 1 -alkoxycarbonyl-4-piperazinyl] reacting a corresponding compound where R 3 is methyl or NR 3 R 4 is 1-methyl-4 piperazinyl, with an alkoxycarbonyl halide; (c) [to obtain compounds where R 3 is H or NR 3 R 4 is 1-piperazinyl] saponification of the products of method (b); (d) [to obtain the compound where R 1 , R 2 and R 5 -R 7 are H and R 3 , R 4 are Me] treating 4-dimethytamino-1-(2- hydroxymethylphenyl) - 1 - styrylbutanol with HCl. Other starting materials and intermediates for which preparative details are given are:- 1 - ethyl - 1 - (2 - propionylphenyl) propanol; 1 - styrylphthalanol and its 3,3-dimethyl and α,3,3-trimethyl derivatives; and 1,1,3-trimethylisobenzofurylium perchlorate. Therapeutic compositions for oral or parenteral administration comprise compounds of the first general formula, above, which are C.N.S.-antidepressants, and pharmaceutically acceptable carriers or diluents.