Synthesis of optically active 2-(N-benzyl-N-methylamino)ethyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (nicardipine).
- 1 January 1980
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 28 (9) , 2809-2812
- https://doi.org/10.1248/cpb.28.2809
Abstract
(+)- and (-)-2-(N-benzyl-N-methylamino)ethylmethyl-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (6) (nicardipine) were synthesized from (-)- and (+)-1-ethoxymethyl-5-methoxycarbonyl-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (3), respectively. Resolution of 3 was carried out using cinchonidine and cinchonine as resolving agents. The vertebral vasodilating activity of (+)-YC-93 [2-(N-benzyl-N-methylamino)ethylmethyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride] was .apprx. 3 times that of (-)-YC-93 in dogs.This publication has 1 reference indexed in Scilit:
- Synthesis of new water-soluble dihydropyridine vasodilators.CHEMICAL & PHARMACEUTICAL BULLETIN, 1979