NO133448B

1316424 α - Hydroxyphenyl - α - (2 - piperidyl)- methanols MINNESOTA 3M LABORATORIES Ltd 19 May 1970 [20 May 1969] 25634/69 Heading C2C Novel α - hydroxyphenyl - α - (2 - piperidyl)- methanols of the general formula wherein R is a hydrogen atom or alkyl group; R1 is a hydrogen atom or a hydroxy or C 1-6 alkoxy group; and R2 is a hydrogen atom or an alkyl, phenyl, phenyl-alkyl, diphenyl-alkyl, phenoxy - alkyl or diphenoxy - alkyl group ("alkyl" meaning C 1-6 alkyl or C 3-6 cycloalkyl in these definitions); and pharmaceutically acceptable acid addition and quaternary ammonium salts thereof are prepared (a) by hydrogenating in the presence of a catalyst a compound of the general formula wherein B is CO or CHOH. Polyhydroxyphenyl 2-pyridyl ketones of the second general formula above wherein B is CO and R2 is a hydrogen atom or alkyl group are prepared by condensing a poly-C 1-6 alkoxybenzaldehyde with a picolinic acid, oxidizing the resulting α-(poly-C 1-6 alkoxyphenyl)-α-(2- pyridyl)-methanol and dealkylating the resulting poly-C 1-6 alkylphenyl 2-pyridyl ketone. α - (C 1-6 alkoxy - p - hydroxyphenyl) - α- (2-pyridyl)-methanols of the second general formula above wherein B is CHOH and R2 is a hydrogen atom or alkyl group are prepared by treating a C 1-6 alkoxy-p-benzyloxybenzaldehyde with a 2-pyridyllithium and hydrogenating the resulting α - (C 1-6 alkoxy - p - benzyloxy - phenyl)- α - (2 - pyridyl) - methanol. They may be oxidized to give the corresponding ketones (B is CO). Polyhydroxyphenyl 2 - pyridyl ketones of the second general formula above wherein B is CO and R2 is a phenethyl or dibenzylmethyl group are prepared by condensing a poly-C 1-6 alkoxy-phenyl methyl-2-pyridyl ketone and 1,3- propanediol in the presence of p-toluenesulphonic acid, treating the resulting 2-(poly- C 1-6 alkoxy - phenol) - 2 - (methyl - 2 - pyridyl)- 1,3-dioxane with phenyllithium and then benzyl chloride and treating the resulting mixture of a 2 - (poly - C 1-6 alkoxy - phenyl) - 2 - (phenethyl- 2 - pyridyl) - 1,3 - dioxane and a 2 - (poly- C 1-6 alkoxy - phenyl) - 2 - (dibenzylmethyl - 2- pyridyl)-1,3-dioxane with HBr. Pharmaceutical compositions having bronchodilatory activity comprise, as active ingredient, an α - hydroxy - phenyl - α - (2 - piperidyl)- methanol of the first general formula above or a pharmaceutically acceptable acid addition or quaternary ammonium salt thereof, together with a pharmaceutical diluent or carrier.