Collect. Czech. Chem. Commun. 1984, 49, 2649-2660

Potential antiparkinsonic agents: Synthesis and pharmacology of some 4-fluoro-4'-halogen'benzhydryl 2-(N,N-disubstituted amino)ethyl ethers

Zdeněk Vejdělek, Jan Metyš, Jiří Holubek, Emil Svátek and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Reactions of 4,4'-dihalogenated benzhydrols and 1,1-diphenylethanols Xab and XIab with sodium hydride and 2-dimethylaminoethyl chloride and 2-pyrrolidinoethyl chloride afforded the ethers Vab-VIIIab. 2-Bromoethyl ethers IXab, obtained from the benzhydrols Xab and 2-bromoethanol by treatment with sulfuric acid, were subjected to substitution reactions with 4-phenylpiperidin-4-ol, 4-(2-tolyl)piperidin-4-ol (XVI), 4-(4-fluorophenyl)piperidin-4-ol and 4-(2-oxobenzimidazolin-1-yl)piperidine (XVII) and gave the amino ethers XIIab-XIVab and XIXab. The products were evaluated as potential antiparkinsonic agents and compared with flunamine (III). The ethers Va, Vb and VIa disclosed anticataleptic activity of a similar degree like that of flunamine (III).