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Preparation process of optically pure ondansetron and its derivative salts

A technology of pure ondansetron and preparation process is applied in the field of preparation technology of optically pure ondansetron and its derivative salts, and achieves the effects of cheap reagents, simple operation and low requirements for production equipment

Active Publication Date: 2017-02-22
NANCHANG CITY BOZEKANG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the preparation method of ondansetron by ultrasonic resolution in the domestic and foreign materials, but it is foreseeable that the method of obtaining optically pure ondansetron by ultrasonic resolution will become the chiral improvement and clinical application of this type of antiemetic drugs in the future. Efficient industrial preparation technology developed

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Weigh 0.147g of ondansetron racemate and 0.18g of O,O'-dibenzoyl-D-tartaric acid resolving agent into a 50ml round-bottomed flask, add 10ml of methanol, ultrasonic for 30 minutes, then suction filter, 0.189g of white powdery solid-O,O'-dibenzoyl-D-tartrate salt of dexondansetron was obtained, the optical purity was 85.7%ee, and the yield was 57.8%.

Embodiment 2

[0032]Weigh 0.147g of ondansetron racemate and 0.18g of O,O'-dibenzoyl-D-tartaric acid resolving agent into a 50ml round-bottomed flask, add 15ml of acetone and 3ml of water, ultrasonically assisted heating and reflux for 1 hour, the solid dissolves quickly, the solution is clear, let stand or stir for cooling for three hours, and filter with suction to obtain 0.180g of white powdery solid - O, O'-dibenzoyl-D-tartrate of dexondansetron , the optical purity was 88.3%ee, and the yield was 55.0%.

Embodiment 3

[0034] Weigh 0.147g of ondansetron racemate and 0.193g of O,O'-di-p-toluyl-D-tartaric acid resolving agent into a 50ml round bottom flask, add 25ml of butyl acetate, and ultrasonicate for 30 minutes After that, suction filtration gave 0.184g white powdery solid-O, O'-di-p-methylbenzoyl-D-tartrate of dexondansetron, the optical purity was 85.7% ee, and the yield was 54.1% .

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Abstract

The invention discloses a preparation process of optically pure ondansetron and its derivative salts, comprising: ultrasonically resolving ondansetron raceme by using a chiral tartrate compound as a resolving agent under ultrasonic condition to obtain its diastereomer salt, crystallizing and purifying the diastereomer salt, extracting by alkalization to obtain optically pure levorotatory ondansetron or dextrotatory ondansetron, and optically pure ondansetron salts are prepared with the optically pure levorotatory ondansetron or dextrotatory ondansetron and related acids. The preparation process of optically pure ondansetron and its derivative salts is simple and feasible and high in speed and efficiency, reagents required herein are cheap, the resolving agent is easy to acquire, nontoxic and easy to recycle, and the preparation process is suitable for industrial preparation.

Description

technical field [0001] The invention relates to a preparation process of optically pure ondansetron and its derivative salts, belonging to the field of pharmaceutical synthesis. [0002] technical background [0003] Ondansetron is a derivative of tetrahydrocarbazolone, and its finished product often exists in the form of hydrochloride dihydrate. The chemical name is 1,2,3,9-tetrahydro-9-methyl-3-[(2 -Methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one hydrochloride dihydrate, molecular formula C 18 h 19 N 3 O·HCl·2H 2 O, there is a chiral carbon atom in the molecule, and it has two configurations of R and S. It is the main component of the drug of choice for the treatment of nausea and vomiting after cytotoxic chemotherapy and radiotherapy. Ondansetron hydrochloride is highly selective to 5-hydroxytryptamine 3 receptor antagonists, and can effectively inhibit nausea and vomiting caused by chemotherapy and radiotherapy. It has no antagonistic effect on dopamine receptors, s...

Claims

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Application Information

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IPC IPC(8): C07D403/06C07B57/00
CPCC07B2200/07C07D403/06
Inventor 胡昱刘志金刘菡龙艳吴雪莹温静袁忠义孙晓霞张玉爱
Owner NANCHANG CITY BOZEKANG PHARMA CO LTD
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