Heterocyclic Derivatives of Triphenylethylenes, Triphenylethanes and Triphenylethanols including Salts and Derivatives Thereof

• Main Authors: FRANCES GERTRUDE FALLON, EDWARD MCCREERY ROBERTS, GEORGE PHILIP CLAXTON
• Format: Patent
• Language: English
• Published: 15.10.1969
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

1,167,613. Heterocyclic derivatives of triphenylethylenes, triphenylethanes and triphenylethanols. RICHARDSON-MERRELL Inc. 25 Jan., 1967, No. 3834/67. Heading C2C. Novel therapeutically active compounds I, II and III (including acid addition salts, quaternary ammonium salts and N-alkyl-N-oxides thereof) wherein R and R1 are each H, Cl or MeO, Z is pyridyl or a partially or completely saturated pyridyl ring which is attached to Y through a ring carbon atom, the nitrogen of the reduced pyridyl ring bearing H or C 1-4 alkyl, andYsignifies, in Formula (I) -CHOR-, -CHOH.CH 2 - (III) -CHOH- or -CHOH.CH 2 - and in which the carbon bearing oxygen is always attached to the phenyl ring, are prepared by reacting a nitrile IV with an organometallic compound containing the pyridine or piperidine nucleus to give a compound II; compounds I are obtained by hydrogenating corresponding compounds II and compounds III are prepared from compounds II utilizing hydroboration and subsequent oxidative hydrolysis. Standard methods are used, usually among compounds to -CHOH-, for introducing an N-methyl group and for hydrogenating the pyridine nucleus; tertiary alcohol groups may be formed by alkylative reduction. 1 - [p - (#,# - Diphenylvinyl) phenyl - 2 - (1- methyl - 2 - pyridino) - ethenolate is obtained by treating 1,1 - diphenyl - 2 - [p - (2 - pyridylacetyl) - phenyl] - ethylene methiodide with aqueous sodium hydroxide.