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Method for preparing trimetazidine hydrochloride

A technology of trimetazidine hydrochloride and piperazine, applied in the field of medicinal chemistry, to achieve high yield, overcome low product purity and good quality

Active Publication Date: 2012-07-11
WUHAN WUYAO SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] We carry out experiment according to above-mentioned technique, but we find by experiment, impurity (formula 2 compound) content is as high as 1.4% in the trimetazidine obtained by this method, needs to just can remove through repeated recrystallization

Method used

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  • Method for preparing trimetazidine hydrochloride
  • Method for preparing trimetazidine hydrochloride
  • Method for preparing trimetazidine hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 196 grams (1.0 moles) of 2,3,4-trimethoxybenzaldehyde, 344 grams (4.0 moles) of anhydrous piperazine, 10 grams of 10% palladium carbon catalyst, 2700 milliliters of water and 300 milliliters of ethanol are dropped into hydrogenation kettle, Airtight, after purging the system with nitrogen, keep the hydrogen pressure at 0.8~1.2MPa, stir the reaction at 70-75°C, after absorbing hydrogen for 1.5 hours, the reactant no longer absorbs hydrogen, cool down, release the pressure, filter to remove palladium carbon, and the filtrate After concentration, add 500 ml of dichloromethane, filter to remove piperazine, and concentrate the filtrate under reduced pressure to obtain a light yellow oil, then add 2000 ml of ethanol, hydrochloric acid to adjust the pH to 1-2, and filter to obtain the crude product of trimetazidine hydrochloride, a mixed solvent of ethanol and water After recrystallization, 275.2 g (0.81 mol) of trimetazidine hydrochloride was obtained, with a yield of 81% and ...

Embodiment 2

[0044] 196 grams (1.0 moles) of 2,3,4-trimethoxybenzaldehyde, 172 grams (2.0 moles) of anhydrous piperazine, 10 grams of 10% palladium carbon catalyst, 2040 milliliters of water and 360 milliliters of ethanol are dropped into the hydrogenation kettle, The hydrogenation and post-treatment methods were the same as in Example 1 to obtain 247.3 g (0.73 moles) of the product, with a yield of 73% and a purity of 99.59% (HPLC).

Embodiment 3

[0046] 196 grams (1.0 moles) of 2,3,4-trimethoxybenzaldehyde, 258 grams (3.0 moles) of anhydrous piperazine, 10 grams of 10% palladium carbon catalyst, 2560 milliliters of water and 240 milliliters of ethanol are dropped into the hydrogenation kettle, The hydrogenation and post-treatment methods were the same as in Example 1 to obtain 264.9 g (0.78 moles) of the product, with a yield of 78% and a purity of 99.63% (HPLC).

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Abstract

The invention relates to a method for preparing trimetazidine hydrochloride. In the method, 2,3,4-trimethoxybenzaldehyde and piperazine are used as raw materials, palladium carbon is used as a catalyst for catalytic hydrogenation so as to salify to generate the trimetazidine hydrochloride, and a solvent used in the hydrogenation is mixed solution of water and ethanol. The solution ensures the complete reaction, cannot cause partial excess of the 2,3,4-trimethoxybenzaldehyde and can reduce impurities.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for preparing an antiangina drug trimetazidine hydrochloride. Background technique [0002] Trimetazidine hydrochloride (Trimetazidine hydrochloride), chemical name: 1-[(2,3,4-trimethoxyphenyl) methyl]-piperazine hydrochloride, structural formula as shown in formula 1: [0003] [0004] Formula 1 [0005] Trimetazidine hydrochloride was originally developed by the French company Servier in the 1970s. It is a strong anti-anginal drug. Its onset is slower than that of nitroglycerin, but its duration of action is longer. Trimetazidine prevents the decrease of intracellular ATP level by protecting the energy metabolism of cells under hypoxic or ischemic conditions, thereby ensuring the normal function of the ion pump and the normal operation of the transmembrane sodium-potassium flow, maintaining the intracellular environment of stability. Controlled expe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/096
Inventor 朱墨张波郭亚兵
Owner WUHAN WUYAO SCI & TECH
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