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[曲哌立定(去甲金雀花碱):立体异构体的分离、稳定性及结构]

[Triperidin (Norakin): separation, stability and structure of stereoisomers].

作者信息

Pfeifer S, Haussner M, Gründemann E, Lücke L

机构信息

Sektion Chemie--Wissenschaftsbereich Pharmazie--der Humboldt-Universität zu Berlin.

出版信息

Pharmazie. 1988 Feb;43(2):102-5.

PMID:3393574
Abstract

The antiparkinsonian triperiden (1; as hydrochloride Norakin) is a mixture of the stereoisomers 1a and 1b. Their identification and separation by chromatographic methods or fractional crystallisation of the tartrates is described. By means of IR- und 13C-NMR spectral data structures of 1a and 1b are proposed. Under proton catalysis 1b racemizes to 1a. In acidic solution (heating in 0.1 mol.1-1 HCl or storage in gastric juice at 37 degrees C) hydrolysis of 1 takes place and four isomeric products were observed (Z1-Z4), which arise by cleavage of the cyclopropyl moiety. The main product Z2 was identified as the 2"-hydroxy derivative. The solid drug is stable at least for 5 years.

摘要

抗帕金森药物三乙哌啶(1;盐酸盐为诺拉金)是立体异构体1a和1b的混合物。文中描述了通过色谱法或酒石酸盐分步结晶对它们进行鉴定和分离的方法。借助红外光谱和13C核磁共振光谱数据,提出了1a和1b的结构。在质子催化下,1b外消旋化为1a。在酸性溶液中(在0.1 mol·L-1盐酸中加热或在37℃的胃液中储存),1会发生水解,观察到四种异构产物(Z1-Z4),它们是由环丙基部分的裂解产生的。主要产物Z2被鉴定为2”-羟基衍生物。固体药物至少稳定5年。

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