Improvements in or relating to Basic Tertiary Alcohols

摘要

1,173,147. Basic tertiary alcohols; ketones. SANDOZ Ltd. 2 Dec., 1966 [6 Dec., 1965; 26 April 1966], No. 54155/66. Heading C2C. Novel compounds of the general formula (wherein R represents H or Me, A and A1 each represent Ph optionally carrying one or two F, Cl, Br, C 1-4 alkyl or alkoxy, or CF 3 substituents, or one or two NH 2 (in A) or NO 2 (in A1) substituents, and Z represents a C 2-8 tertiary amino group, which may be in the form of a mono- or bi-cyclic heterocyclic radical having at most 8 carbon atoms the nucleus of which may contain an O atom or a second N atom optionally substituted by a C 1-4 alkyl radical) are prepared by reacting a compound A1-CO-CH 2 -Z with 2-pyridyl lithium in an open-chain or cyclic ether at or below - 20‹ C. and hydrolysing the product to a compound (II), and, if desired, hydrogenating this, either alone to form a compound (I) in which R = H, or in the presence of formaldehyde to form a compound (I) in which R = Me. In the hydrogenation step, any NO 2 groups in A1 are reduced to NH 2 , and any aromatic groups in Z may be reduced to cycloaliphatic groups. Compounds (I) and (II) may be converted into addition salts by reaction with inorganic or organic acids, whilst compounds I may also be converted into quaternary ammonium salts by reaction with alkyl bromides or iodides. Ketones of the formula A1-CO-CH 2 -Z, wherein A1 and Z have the above significance, are prepared by treating the correspondingly substituted acetophenone with bromine and treating the resulting ketone A1-CO-CH 2 -Br with HZ. Pharmaceutical compositions having an effect on the central nervous system and a dimetric and hypoglycerric effect contain as the active ingredients the above novel compounds and may be administered orally or parenterally.