Optisch aktive,basisch substituierte Phenylacetonitrile

摘要

1377209 Basically substituted-d-phenylacetonitriles KNOLL AG CHEMISCHE FABRIKEN 2,9 Nov 1971 [5 Dec 1970] 55258/71 Heading C2C The invention comprises a process for the preparation of dextro-rotatory phenyl acetylenes of Formula I: wherein A=OCH 3 or CF 3 ; B=H or OCH 3 ; D=H or OCH 3 ; E=H, OCH 2 C 6 H 5 , CF 3 or OCH 3 ; G=H, Cl or OCH 3 and K=H or OCH 3 , or wherein E and G each represents an OC 2 H 5 group and K represents H, by (a) reacting a compound of Formula II: with a compound of Formula III: or (b) reacting a compound of Formula IV: with a compound of Formula V: The invention also comprises novel dextrorotatory phenyl acetonitriles of Formula I1: wherein A1 represents OCH 3 ; B1, D1 and K1 independently represent H or OCH 3 ; E1 represents H, OCH 3 or O-benzyl; G1 represents H, OCH 3 or Cl; or wherein E1 and G1 each represents OC 2 H 5 and K1 represents hydrogen. The dextrorotatory isomers of γ-cyano-γ-3,4- dimethoxy phenyl-γ-isopropylbutyric acid, γ- cyano - γ - 3 - trifluoromethylphenyl - γ - isopropyl butyric acid and 4-cyano-4-(3,4,5-trimethoxyphenyl)-5-methyl hexanoic acid are obtained by resolution of the corresponding racemic acids with brucine and these acids are reduced with sodium borohydride or lithium aluminium hydride to obtain the corresponding d-3-cyano- 3 - (substituted phenyl) - 2 - methyl - hexan - 1 - ols which are in turn reacted with thienyl chloride to obtain the corresponding d-1-chloro-3-cyano- 3 - (substituted phenyl) - 2 - methyl hexanes. d - 4 - Cyano - 4 - (3,4 - dimethoxyphenyl) - 4- isopropyl - N - methylbutylamine and d - 4- cyano - 4 - isopropyl - 4 - (3 - trifluoromethylphenyl) - N - methylbutylamine are prepared by reacting the corresponding halides with methyl amine. 4 - Cyano - 4 - (3,4,5 - trimethoxyphenyl) - 5- methylhexanoic acid is prepared by partial saponification of 1,3-dicyano-3-(3,4,5-trimethoxyphenyl) - 4 - methylpentane with aqueous alcoholic NaOH. Pharmaceutical compositions comprise a compound of Formula I1 and a therapeutically acceptable carrier.