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Method for preparing chiral azelnidipine and acceptable salt thereof

A technology of azeldipine and azela, which is applied in the field of preparing chiral azeldipine and can solve the problems of small processing capacity, inability to use large-scale production activities, expensive instruments and equipment, etc.

Active Publication Date: 2009-12-02
北京华禧联合科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It requires expensive equipment and low throughput, and cannot be used in large-scale production activities

Method used

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  • Method for preparing chiral azelnidipine and acceptable salt thereof
  • Method for preparing chiral azelnidipine and acceptable salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Example 1: Preparation of R-(-)-Azedipine-semi-D(-)-tartrate monosalt

[0012] Dissolve 0.29 g (0.5 mmol) of Azedipine in 5 ml of DMSO, add 0.04 g (0.5 mmol) of D-(-)-tartaric acid under heating and stirring, stir at 60°C for 1-4 hours, and filter out the solid , washed and dried with anhydrous acetone to obtain 0.11 g of R-(-)-azendipine-semi-D(-)-tartrate monosalt salt, chiral HPLC assay 99.0% d.e.

Embodiment 2

[0013] Example 2: Preparation of R-(-)-Azedipine-D(+)-camphorsulfonate monoDMSO solvate

[0014] Dissolve 0.29 g (0.5 mmol) of Azedipine in 5 ml of DMSO, add gram (mol) of D(+)-camphorsulfonic acid under stirring conditions, stir for 1-4 hours, and filter out the solid, wash and dry with n-hexane , to obtain gram R-azendipine-semi-D(+)-camphorsulfonate monoDMSO solvate, chiral HPLC assay 99.3% d.e.

Embodiment 3

[0015] Example 3: Preparation of R-(-)-Azeldipine-Semi-D(-)-Camphorsulfonate MonoDMSO Solvate

[0016] Dissolve R-(-)-azendipine-semi-D(-)-tartrate monoDMSO solvate in 20 mL of ethanol / acetone / methanol / water and add 15 mL of sodium bicarbonate / hydroxide with stirring Sodium solution, TLC detection, until the reaction is complete, ethyl acetate / n-hexane / benzene extraction 3 times, combined organic phase and vacuum distillation to obtain a solid, add methanol to dissolve, crystallize, filter to obtain R-(-)-A Zedipine, determined by chiral HPLC 99.1%, []20D=-68.2 (C=1, MeOH).

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Abstract

The invention relates to a method for preparing (S)-(+)-azelnidipine and (R)-(-)-azelnidipine as well as benzene sulfonic acid, paratoluenesulfonic acid, D-(+)-camphorsulfonic acid, L-(-)-camphorsulfonic acid, taurine and high taurine salt thereof by economically and effectively resoluting racemic azelnidipine. Compared with the prior method for preparing optically active azelnidipine and salt thereof by a high performance liquid chromatography which needs expensive instruments and equipment and has less treatment amount, the method adopts a recrystallization resolution method of the prior chiral resolution reagent and a cheap and easily-obtained solvent, has large sample treatment amount and simple operation, does not need special instruments, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing chiral azelnidipine, using commonly used chiral resolution reagents (S)-(+)-mandelic acid, D-(-)-tartaric acid, D-(+)-malic acid, D- (+)-Camphoric acid, D-(+)-Camphorsulfonic acid, L-(-)-Camphorsulfonic acid, form a salt with Azelnidipine, select a suitable chiral auxiliary such as DMSO, crystallize, separate, add The base liberates the optically active azelnidipine. [0002] [0003] R-(-)-Azedipine S-(+)-Azedipine Background technique [0004] Azedipine is a dihydropyridine calcium channel blocker, which is the first-line drug for the treatment of hypertension. It has a mild and long-lasting antihypertensive effect and has the characteristics of less stimulation to the heart. It is a highly soluble lipid, which is retained on the blood vessel wall after being cleared from the blood and continues to exert its antihypertensive effect. The effect and curative effect are good, and the incidence of sid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
Inventor 王玉莉毕华
Owner 北京华禧联合科技发展有限公司
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