【结 构 式】 |
【药物名称】Rapacuronium bromide, Org-9487, Raplon 【化学名称】1-[3alpha-Acetoxy-2beta-(1-piperidinyl)-17beta-(propionyloxy)-5alpha-androsta-16beta-yl]-1-allylpiperidinium bromide 【CA登记号】156137-99-4 【 分 子 式 】C37H61BrN2O4 【 分 子 量 】677.81372 |
【开发单位】Organon (Originator) 【药理作用】Adjuncts to Anesthesia, ANALGESIC AND ANESTHETIC DRUGS, Neuromuscular Blockers |
合成路线1
The acetylation of (2beta,3alpha,5alpha,16beta)-3-hydroxy-2,16-bis(piperidin-1-yl)androstan-17-one (I) with acetyl chloride in dichloromethane gives the corresponding 3-acetoxy derivative (II), which is reduced with NaBH4 in methanol - THF yielding (2beta,3alpha,5alpha,16,beta,17beta)-3-acetoxy-17-hydroxy-2,6-bis (piperidin-1-yl)androstane (III). The acylation of (III) with propionyl chloride in dichloromethane as before affords the 3-acetoxy-17-propionyloxy derivative (IV), which is finally quaternized with allyl bromide in dichloromethane.
【1】 Sleigh, T.; Carlyle, I.C.; Muir, A.W. (Akzo Nobel N.V.); Monoquaternary 2,16-bispiperidinylandrostane derivs. EP 0571012; JP 1995267984; US 5418226 . |
【2】 Graul, A.; Prous, J.; Castañer, J.; Org-9487. Drugs Fut 1994, 19, 10, 916. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(I) | 16465 | (2S,3S,5S,8R,9S,10S,13S,14S,16S)-3-hydroxy-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-17H-cyclopenta[a]phenanthren-17-one | C29H48N2O2 | 详情 | 详情 | |
(II) | 16466 | (2S,3S,5S,8R,9S,10S,13S,14S,16S)-10,13-dimethyl-17-oxo-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C31H50N2O3 | 详情 | 详情 | |
(III) | 16467 | (2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-hydroxy-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C31H52N2O3 | 详情 | 详情 | |
(IV) | 16468 | (2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-(acetoxy)-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl propionate | C34H56N2O4 | 详情 | 详情 |