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New synthetic process for vinpocetine semisynthesis

A technology of vinpocetine and vincamine, applied in the field of vinpocetine, which can solve the problems of lengthy steps, many by-products, and high price of vincamine, and achieve the effects of simple equipment, large economic and social benefits, and green production procedures

Active Publication Date: 2014-06-25
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The second route has short reaction steps, simple operation, and better control of the process flow. However, the current price of vincamine raw materials is relatively high, resulting in high production costs of vinpocetine by this process for various manufacturers.
[0004] To sum up the preparation process, the first route has lengthy steps, low yield of vinpocetine, many by-products, heavy pollution and complicated operation, which makes the final product cost high and has no market competitiveness
The second route, due to the high price of vincamine, the total yield is not high, which also makes the final cost of vinpocetine too high

Method used

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  • New synthetic process for vinpocetine semisynthesis

Examples

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Effect test

Embodiment 1

[0012] Example 1 Synthesis of Vinpocetine

[0013] In a 500 L reactor, add 200 L of absolute ethanol as a solvent, 50 kg of vincamine as a reaction raw material, and 3.0 kg of sodium ethoxide as a catalyst in the reactor to make the pH of the system around 14, slowly raise the temperature to 70°C, and react for 3 h. Thin-layer chromatography monitors the complete reaction of the raw material vincamine, which is regarded as the completion of the hydrolysis reaction, and the generated product is a mixture of vincine and dehydrovincine. Continue in the same reaction kettle, stir and lower the temperature below 10°C, add glacial acetic acid to adjust the pH value to about 12, then raise the temperature to reflux, react for 2-4 hours, and monitor the vincine point by thin-layer chromatography to be no more than 5%. The dehydration reaction is complete. The product mainly composed of anhydrovincine was obtained. Continue in the same reactor, stirring and lowering the temperature b...

Embodiment 2

[0014] Example 2 Separation and purification of vinpocetine

[0015] The vinpocetine ethanol solution obtained in the synthesis steps is transferred to a concentrator, concentrated under reduced pressure to recover ethanol. Then add 200 L of dichloromethane and 200 L of water, transfer to an extraction tank for extraction and separation, extract and separate the dichloromethane twice, combine the organic phases, and dry with anhydrous sodium sulfate. Then transfer to a stirring concentrator to recover dichloromethane to dryness to obtain crude vinpocetine. Then add 450 L of absolute ethanol and heat to dissolve, fine filter, and the filtrate is transferred to a crystallization tank with a concentrator. After concentrating 300 L of ethanol under reduced pressure, the mixture was stirred and cooled to below 10 °C for 2 h to crystallize, filtered and dried to obtain 43.2 kg of fine vinpocetine with a weight yield of 86.4%. The purity by HPLC is 99.3%, and the content is 99.5% b...

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Abstract

The invention provides a vinpocetine semisynthesis process. The vinpocetine is obtained through hydrolysis, dehydration and esterification reactions by a one-pot method, and after the reactions are finished, extraction separation, purification and crystallization are performed, and finally, the high-content and high-purity product can be obtained. The method is few in reaction steps, simple in process flow, high in vinpocetine yield, simple in equipment, and green and environment-friendly in production procedure, and has tremendous economic and social benefits.

Description

technical field [0001] The invention relates to the semi-synthesis of vinpocetine, an indole alkaloid drug with good physiological activity, in particular to the synthesis of vincamine as the raw material, the reaction including hydrolysis and esterification, and the one-pot method to prepare vinpocetine. Background technique [0002] Vinpocetine, the English name Vinpocetine, namely apovincine ethyl ester, is a polycyclic indole active alkaloid, and is currently the first-line drug for the treatment of cardiovascular and cerebrovascular diseases in China. At present, there are two dosage forms of tablets and injections in China. Vinpocetine for injection has the best sales volume and the best effect in China. As a cerebral vasodilator, vinpocetine can inhibit the activity of phosphodiesterase, increase the effect of c-GMP, the messenger of vascular smooth muscle relaxation, and selectively increase cerebral blood flow. In addition, it can also inhibit platelet aggregation, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D461/00
CPCC07D461/00
Inventor 彭学东张梅赵金召闫勇义
Owner ZHANG JIA GANG VINSCE BIO PHARM
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