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A kind of chiral separation method of four isomers in racemic anisodamine

An anisodamine and chiral separation technology, applied in the field of medicine, can solve the problems of being unable to be suitable for industrialized large-scale production, small preparation amount, long time-consuming and the like

Active Publication Date: 2021-04-09
HARBIN MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The patent application with the publication number CN107991367A tries to use capillary electrophoresis to separate the four optical isomers of anisodamine, but due to the defects of long time consumption and small preparation amount, the method is limited to laboratory preparation and cannot be applied to industrial mass production

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  • A kind of chiral separation method of four isomers in racemic anisodamine
  • A kind of chiral separation method of four isomers in racemic anisodamine
  • A kind of chiral separation method of four isomers in racemic anisodamine

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Embodiment 1

[0026] The chiral resolution of four isomers in embodiment 1 racemic anisodamine

[0027] 1. Sample preparation

[0028] The racemic anisodamine sample (sample concentration: 100 mg / mL) was completely dissolved in an aqueous solution containing 45% (v / v) methanol, passed through a 0.22 μm microporous membrane for use.

[0029] 2. HPLC chromatographic separation

[0030] Mobile phase: a mixed solution of methanol, water and diethylamine, wherein the volume ratio of methanol:water:diethylamine=45:55:0.02.

[0031] Chromatographic conditions: the detection wavelength is 210nm, the chromatographic column is an Agilent Prep C18 column (250mm×9.4mm), the column temperature is 20°C, the injection volume is 1mL, and the flow rate is 5mL / min.

[0032] The separated product was analyzed by HPLC under the following conditions: the mobile phase methanol: water: diethylamine volume ratio was 50:50:0.02, the chromatographic column was a cosmosil MS-II C18 column, the column temperature wa...

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Abstract

The invention discloses a chiral resolution method for four isomers in racemic anisodamine. The present invention uses D or L-p-methyldibenzoyl tartaric acid as a resolving agent, and adopts a preparative HPLC combined chemical resolution method to resolve racemic anisodamine. The method is reasonable in design, practical, high in product yield and high in purity, and the obtained anisodamine four optical isomers 6R, 2'R, 6R, 2'S, 6S, 2'S, 6S, and 2'R have the same purity. It is more than 95%, which is a relatively effective method for the industrial production of the four optical isomers of anisodamine. The method successfully realizes the resolution of four optical isomers, can effectively reduce the cost of resolution of the four optical isomers of anisodamine, and produces extensive social benefits, huge economic benefits, and broad application prospects.

Description

technical field [0001] The invention relates to a chiral resolution method for four isomers in racemic anisodamine, through which the chiral resolution of four optical isomers in racemic anisodamine can be realized. The invention belongs to the technical field of medicine. Background technique [0002] Anisodamine can compete with acetylcholine to antagonize M receptors, and is used for the treatment of smooth muscle spasm, neuralgia, fulminant meningitis, bacterial meningitis, toxic dysentery and circulatory disorders caused by vasospasm. Racemic anisodamine is a synthetic product of anisodamine (654-2), which contains four optical isomers, respectively 6R, 2'S, 6S, 2'R, 6R, 2'R, 6S, 2'S configurations. Relevant animal experiments have proved that the 6S, 2'S isomer exhibits the strongest pharmacological activity in terms of the relaxation effect of the isolated rat trachea. On the relaxation effect of isolated rat small intestinal smooth muscle, 6R, 2'S isomer showed the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D451/10
CPCC07D451/10
Inventor 杨宝峰李畅朱久新王立波韩维娜黄健王金辉
Owner HARBIN MEDICAL UNIVERSITY
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