83200-10-6

Anipamil,Onbio Inc.

A long-acting analog of Verapamil (V125000) with antiarrhythmic and antihypertensive activity.

1,7-Bis-(3-ethoxyphenyl)-3-methylaza-7-cyano-nonadecane:
0.06 mole of 1-cyano-1-(3-methoxyphenyl)tridecane (prepared by phase transfer-catalyzed alkylation of 3-methoxyphenylacetonitrile with 1- bromododecane) and 0.06 mole of 1-chloro-4-methylaza-6-(3- methoxyphenyl)hexane [prepared from N-methyl-β-(3- methoxyphenyl)ethylamine and 1-bromo-3-chloropropane by a method similar to that described in Arzneim.-Forsch. 28 (II) (1978), 2048] were dissolved in 100 ml of dry toluene in a three-necked flask provided with a stirrer, dropping funnel, reflux condenser and thermometer. 9.3 g (0.07 mole) of a 30% strength suspension of sodium amide in toluene were then added dropwise at from 100° to 110°C, with stirring, and stirring was continued under reflux for a further 90 minutes.
The resulting reaction solution was poured into 200 ml of ice water, and the toluene phase was separated off and washed twice with water. The required amount of hydrochloric acid was added to the toluene solution, the toluene was distilled off under reduced pressure and the residue, which remained was recrystallized from acetone to give 1,7-bis-(2-methoxyphenyl)-3-methylaza-7- cyanononadecane hydrochloride or α-dodecyl-3-methoxy-α-[3-[[2-(3- methoxyphenyl)ethyl]methylamino]propyl]benzene-acetonitrile (anipamil); MP: 60°-69.5°C.

Coronary vasodilator, Antihypertensive

This novel, orally active phenylalkylamine derivative (FW = 520.79 g/mol; CAS 83200-10-6; IUPAC: 2- (3-methoxyphenyl) -2-[3-[2- (3-methoxy- phenyl) ethylmethylamino]-propyl]tetradecanenitrile, exhibits calcium channel-blocking activity that is confined peculiarly to myocardial muscle.