hexobendine

Originator

Reoxyl,Hormonchemie,W. Germany,1966

The Uses of hexobendine

Vasodilator .

Background

Hexobendine is a medication used to cause vasodilation, to treat several conditions including angina pectoris. It has not been approved in the United States or the United Kingdom, but has been used widely in Austria and Germany .

Definition

ChEBI: Hexobendine is a trihydroxybenzoic acid.

Manufacturing Process

Methylacrylate and N,N'-dimethylethylenediamine are first reacted and that product reduced with lithium aluminum hydride to give a compound A.
To a solution of 13 parts of compound A and 12 parts by volume of absolute pyridine in 80 parts by volume of absolute dioxane there are added dropwise and under constant stirring 35 parts of 3,4,5-trimethoxybenzoyl chloride dissolved in 70 parts by volume of absolute dioxane in the course of 30 minutes. The mixture is stirred for a further 3 hours at a temperature of 100°C and the excess solvent is then evaporated in vacuo. The residue of the evaporation is treated with ethyl acetate and saturated sodium carbonate solution, whereafter the organic phase is separated, treated with water, dried with sodium sulfate and the solvent is removed in vacuo. The residue thus obtained is taken up in ether and separated from 4 parts of insoluble trimethoxybenzoic acid anhydride by filtration. After evaporation of the ether there are obtained 32.5 parts of N,N'-dimethyl-N,N'-bis-[3-(3,4,5- trimethoxybenzoxy)propyl]-ethylene diamine, corresponding to a yield of 86% of the theoretical. MP: 75°C to 77°C.
The di-tertiary base thus obtained is dissolved in ether and the solution is saturated with hydrogen chloride gas. After isolation and reprecipitation from methanol-ether there is obtained the dihydrochloride melting at 170°C to 174°C.

Therapeutic Function

Vasodilator

Metabolism

Not Available