Cis-isomer of anisodamine and separation and detection method thereof

A technology of cis-isomers and anisodamine, which is applied in the field of drug separation and analysis, can solve the problems of low purity of optical isomers, and achieve the effects of improving purity, improving safety and effectiveness, and good peak shape

Pending Publication Date: 2022-08-09
CHENGDU FIRST PHARMACEDTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention provides the cis-isomer of anisodamine and its separation and detection method in order to solve the technical problem of defects such as the low purity of the separated optical isomer in the existing separation method in the above-mentioned background technology

Method used

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  • Cis-isomer of anisodamine and separation and detection method thereof
  • Cis-isomer of anisodamine and separation and detection method thereof
  • Cis-isomer of anisodamine and separation and detection method thereof

Examples

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Effect test

Embodiment 1

[0073] A kind of separation method of the cis isomer of anisodamine, comprising the following steps:

[0074] S1. Take 14 g of racemic anisodamine for separation by dynamic preparative HPLC to obtain cis-anisodamine containing 6R, 2'S and 6S, 2'R and trans-anisodamine containing 6R, 2'R and 6S, 2'S Alkali, 7g in total;

[0075] The chromatographic parameters that the preparative HPLC separates are as follows:

[0076] Chromatographic column: DAC80 dynamic preparation separation column;

[0077] Column packing: Huapu LD-2-C18;

[0078] Flow rate: 200ml / min;

[0079] Wavelength: 210nm;

[0080] When the elution time is 0-45min, the mobile phase is a mixture of 0.1% formic acid and methanol in a mass ratio of 95:5; when the elution time is 45-60min, the mobile phase is 0.1% formic acid and methanol according to 30:5 70 mass ratio mixed mixture. The resulting cis-anisodamine and trans-anisodamine split map such as figure 1 shown.

[0081] S2. After adjusting the pH of the ...

Embodiment 2

[0098] Get the anisodamine of 6R that step S3 obtains in embodiment 1, 2'S, adopt LCMS to detect, obtain the front peak of anisodamine cis-isomer as follows: Figure 5 shown, from Figure 5 It can be proved in Example 1 that the anisodamine of 6R, 2'S was successfully isolated, and the parameters of LCMS are as follows:

[0099] Chromatographic column: Waters X Bridge C18 column (50mm*4.6mm*3.5um);

[0100] Mobile phase: mobile phase A is 0.01mol / L NH 4 HCO 3 , mobile phase B is acetonitrile;

[0101] The flow rate is 2mL / min, the column temperature is 40℃, when the elution time is 0~1.6min, the mobile phase B is 5%~95%, and when the elution time is 1.6~3min, the mobile phase B is 95%.

Embodiment 3

[0103] Get the anisodamine of 6S that step S3 obtains in embodiment 1, the anisodamine of 2'R, adopt LCMS to detect, obtain the back peak of anisodamine cis-isomer as follows: Image 6 shown, from Image 6 It can be proved that the anisodamine of 6S and 2'R was successfully separated in Example 1, and the parameters of LCMS are as follows:

[0104] Chromatographic column: Waters X Bridge C18 column (50mm*4.6mm*3.5um);

[0105] Mobile phase: mobile phase A is 0.01mol / L NH 4 HCO 3 , mobile phase B is acetonitrile;

[0106] The flow rate is 2mL / min, the column temperature is 40℃, when the elution time is 0~1.6min, the mobile phase B is 5%~95%, and when the elution time is 1.6~3min, the mobile phase B is 95%.

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Abstract

The invention belongs to the field of medicine separation and analysis, and particularly relates to a cis-isomer of anisodamine and a separation and detection method of the cis-isomer. Through combination of HPLC and supercritical chromatography, the cis-isomer of racanisodamine can be effectively separated, and then through creative chromatographic parameter selection in HPLC and supercritical chromatography, the separation degree is improved, so that the purity of the two finally obtained cis-isomer monomers of anisodamine is high, and the purity of the two obtained cis-isomer monomers is high. And a foundation is laid for large-scale industrial application.

Description

technical field [0001] The invention belongs to the field of drug separation and analysis, in particular to a cis isomer of anisodamine and a separation and detection method thereof. Background technique [0002] Anisodamine can compete with acetylcholine to antagonize M receptors, and is used to treat smooth muscle spasm, neuralgia, fulminant meningitis, coccal meningitis, toxic dysentery and circulatory disorders caused by vasospasm. Racemic anisodamine is a synthetic product of anisodamine (654-2), including four optical isomers, which are 6R, 2'S, 6S, 2'R, 6R, 2'R, 6S, 2'S configurations. Relevant animal experiments have shown that the 6S, 2'S isomer exhibits the strongest pharmacological activity in terms of the relaxation effect of isolated rat trachea. The 6R,2'S isomer showed the strongest pharmacological activity in the relaxation effect of isolated rat small intestinal smooth muscle. Therefore, racemic anisodamine is separated into four optical isomers by the met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D451/10G01N30/02G01N30/32G01N30/34G01N30/54G01N30/60
CPCC07D451/10G01N30/02G01N30/34G01N30/32G01N30/54G01N30/6052G01N2030/324C07B2200/09C07B2200/07Y02P20/54
Inventor 刘昭华杨美刘武何杰罗斌王恒
Owner CHENGDU FIRST PHARMACEDTICAL CO LTD
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