3-Alkylamino-2-hydroxy-propoxy-benzyl cyanide cpds. - with beta-adrenolytic and hypotensive activity

摘要

4-(3-Alkylamino-2-hydroxypropoxy)benzyl cyanides of formula (I) and their optical isomers and acid-addn. salts are new. In (I), R1 is i-Pr or t-Bu; R2 is H, Cl, Me, OMe or COMe; R3 and R4 are H or Me, or R3+R4 is (CH2)4 or CH2CH2OCH2CH2. (I) have beta-adrenolytic and hypotensive activity and are useful for treating angina pectoris, hypertension and arrhythmia. In an example, a mixt. of 35g 3-chloro-4-(2,3-epoxypropoxy)benzyl cyanide, 20ml t-BuNH2 and 50 ml i-PrOH was refluxed for 22 hr, cooled, and evapd. The residue was taken up in aq. HCl, filtered, washed with ether, and extracted with CHCl3. The extract was dried and evapd. and the residue recrystd. from EtOAc/MeOH to give 19g of (I; R1=t-Bu, R2=Cl, R3=R4=H).HCl, m.pt. 91-93 deg.C.