PROCEDIMIENTO PARA LA OBTENCION DE DERIVADOS DEL 2-HIDROXI-3-AMINOPROPANO DE ACTIVIDAD BETA-RECEPTORA.

摘要

1465946 Propanolamine derivatives CIBA GEIGY AG 13 Feb 1974 [20 Feb 1973 31 Jan 1974] 6518/74 Heading C2C Compounds of the general formula (I) (Het=optionally substituted pyridazinyl, pyrimidinyl, pyrazinyl or substituted pyridyl, R 1 = H or CH 3 and R 2 =C 1-7 alkyl, optionally substituted phenyl-(C 1-7 , alkyl), carboxy-(C 1-7 , alkyl) or functionally modified carboxy-(C 1-7 alkyl), provided that Het does not represent pyrazin-2 or 3-yl substituted at the 3- or 2-position respectively by C 1-5 alkyl or unsubstituted phenyl when R 1 R 2 CH 3 C- is C 3-6 alkyl or unsubstituted phenyl (C 3-6 ) alkyl, their condensation products with aldehydes, ketones and carbonic acid, and their N-oxides and salts are prepared by reacting (a) Het-O-CH 2 CHX 1 CH 2 Z 1 or an N-oxide thereof with Z 2 CCH 3 R 1 R 2 (one of Z 1,2 =NH 2 , the other=reactive esterified OH and X 1 =OH, or X 1 +Z 1 =O and Z 2 =NH 2 ), (b) Het-Z (Z= nucleophilically removable radical) with HOCH 2 CHOHCH 2 NHCCH 3 R 1 R 2 or the condensation product with an aldehyde, ketone or carbonic acid or (c) 3-hydroxypyridine with ZCH 2 CHX 1 CH 2 NHCCH 3 R 1 R 2 (Z = reactive esterified OH and X 1 = OH, or Z + X 1 = O) or the corresponding azetidine, optionally followed by introduction, modification or removal of substituents, conversion to a different compound of formula (I), isomer separation and/or salt formation. The preparation of starting materials for processes (a) and (b) and 2-allyloxy-3-morpholinopyrazine, 2-allyloxy-3-dimethylaminopyrazine, 2- allyloxy - 3 - isopropylaminopyrazine, 3 - chloro- 2-[21,21-dimethyl-11,31-dioxolanyl-(41)]methoxypyridine, 3 - chloro - 2 - (21,31 - dihydroxypropoxy)pyridine, 3 - (21,31 - dihydroxypropoxy)- 2 - methoxypyridine, 2 - [21,21 - dimethyl- 11,31 - dioxolanyl - (41)] - methoxypyrimidine, 2 - (21,31 - dihydroxypropoxy)pyrimidine, 5- hydroxymethyl-, chloromethyl-, cyanomethyl- and # - aminoethyl - 2,3 - dichloropyridine, 3 - benzylamino - 1,2 - propanediol, 3-benzyl - 5 - hydroxymethyl - 2 - phenyloxazolidine, 2 - (31 - benzylamino - 21 - hydroxypropoxy) - 3 - methylpyridine, 2 - hydroxy - 3 - chloropyridine - 5 - carboxylic acid, 5 - hexylcarbamoyl - 2,4(6) - dichloropyrimidine, 5 - (# - methoxyethyl)uracil, 5 - (# - methoxyethyl) - 2,4(6) - dichloropyrimidine, 5 - methylthiomethyluracil, 5 - methylthiomethyl - 2,4(6)- dichloropyrimidine and 5-ethyl-4-hydroxypyrimidine is described. Some of the above compounds are #-adrenergic blocking agents and some are stimulants. They may be administered in the form of pharmaceutical and veterinary preparations containing them in association with a carrier.