PHENETHANOLAMINE ETHERS

摘要

1,260,521. Phenylethanolamine derivatives. ALLEN & HANBURYS Ltd. 23 Jan., 1970 [6 Feb., 1969], No. 6379/69. Heading C2C. Compounds of the general formula (R1 = C 1-6 alkyl, C 2-6 alkenyl or aralkyl, each optionally substituted by one or more OH or alkoxy groups; R2 = H, C 1-6 alkyl optionally substituted by one or more OH, amino or heterocyclic groups, or cycloalkyl, aralkyl or aroxyalkyl each optionally substituted by one or more OH or alkoxy groups; R3=H, PhCH 2 ; X= -CONR4R5; R4,5 = H, C 1-6 alkyl; provided that when R2=tert.-butyl and R1=PhCH 2 , R3=H) and their acid addition salts are prepared by (a) reacting a compound of the formula or (Hal=halogen) with NHR2R3, with subsequent reduction of the keto group where the starting material is a ketone, (b) reacting R1Hal with a compound of the formula or with subsequent reduction of the keto group where the starting material is a ketone (the benzyl group(s) may also be removed) or (c) alkylation of compounds in which R2,3=H by condensation with a carbonyl compound and reduction of the azomethine, optionally followed in each case by salt formation and/or resolution. The preparation of 5-(N-benzyl-N-tert.-butylglycyl)-o-anisic acid methyl ester hydrochloride 5- (2-tert.-butylamino-1-hydroxyethyl)-o-anisic acid methyl ester hydrochloride, 2-benzyloxy-5-[1-hydroxy-2-isopropylaminoethyl] benzoic acid methyl ester hydrochloride and 5-[N-benzyl-N-(1,1-dimethyl-3-phenylpropyl)glycyl]-o-anisicacid methyl ester hydrochloride is described. These compounds are #-adrenergic blocking agents, and some of them also antagonize α- adrenergic receptors. They may be administered in the form of pharmaceutial preparations containing them in association with a carrier.