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Cinepazide maleate compound with novel route

A kind of technology of cinepazide maleate and compound, which can be applied in the field of medicine and can solve the problems of strong toxicity of solvent anhydrous benzene and the like

Inactive Publication Date: 2010-07-14
HAINAN MEILAN SMITH KLINE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Reaction of trans 3,4,5-trimethoxycinnamoyl chloride with 1-piperazine acetylpyrrolidine, NaHCO 3 The acid-binding agent is reacted in anhydrous benzene to prepare cinepazide, which is then salted with maleic acid; the solvent anhydrous benzene used in this method is highly toxic and has been restricted in the pharmaceutical industry.

Method used

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  • Cinepazide maleate compound with novel route
  • Cinepazide maleate compound with novel route
  • Cinepazide maleate compound with novel route

Examples

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Effect test

Embodiment 1

[0047] The preparation of embodiment 1 cinepazide maleate

[0048](1) Add 22.2g of chloroacetyl chloride into 90mL of chloroform, stir and cool down to -10°C, slowly add 36ml of a chloroform solution of 14g tetrahydropyrrole and 21g triethylamine dropwise, during which the temperature is not higher than 0°C, and the dropwise Afterwards, stir to return to room temperature, continue to react for 1 hour, add water to wash three times, 30ml each time, dry with anhydrous sodium sulfate, distill off the solvent to obtain a brown liquid, place it at room temperature to solidify, and obtain 24g of the product;

[0049] (2) Suspend 9.6 g of 3,4,5-trimethoxycinnamic acid in 30 g of dichloromethane, add 30 g of bis(trichloromethyl) carbonate under stirring, stir at room temperature for 3 hours, then distill under reduced pressure Chloromethane, under ice-cooling, add piperazine 8.2g and 25% potassium hydroxide aqueous solution 50ml, stir at 0°C for 2 hours, solid precipitates, filter to ...

Embodiment 2

[0052] The preparation of embodiment 2 cinepazide maleate

[0053] (1) Add 44.3g of chloroacetyl chloride into 200mL of chloroform, stir and cool down to -5°C, slowly add 36ml of a chloroform solution of 28.4g of tetrahydropyrrole and 45g of triethylamine dropwise, during which the temperature is not higher than 0°C, dropwise After completion, stir to return to room temperature, continue to react for 1 hour, add water to wash three times, 50ml each time, dry with anhydrous sodium sulfate, distill off the solvent to obtain a brown liquid, place it at room temperature to solidify, and obtain 48.5g of the product;

[0054] (2) Suspend 19.3 g of 3,4,5-trimethoxycinnamic acid in 60 g of dichloromethane, add 60 g of bis(trichloromethyl) carbonate under stirring, stir at room temperature for 3 hours, then distill under reduced pressure Chloromethane, under ice-cooling, add 16.5g of piperazine and 100ml of 25% aqueous potassium hydroxide solution, stir at 0°C for 2 hours, a solid prec...

Embodiment 3

[0060] The refining of embodiment 3 cinepazide maleate

[0061] Take 10 g of cinepazide maleate salt, add 140 mL of absolute ethanol for recrystallization, and obtain 9.5 g of the product with a yield of 95% and a melting point of 172°C.

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PUM

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Abstract

The invention provides a cinepazide maleate compound with a novel route. Concretely, the method comprises the step of making 3, 4, 5-trimethoxy cinnamic acid and piperazidine take reaction in the existence of dichloromethyl (trichloromethyl) carbonic ether for producing 3, 4, 5-trimethoxy cinnamoyl piperazine. Through using the dichloromethyl (trichloromethyl) carbonic ether as acid activated groups, the invention simplifies the reaction steps, and reduces the environment pollution, in addition, the superfluous piperazidine is separated through the reaction with the piperazidine at first, and the processing steps are simplified, so the subsequent purification becomes easy.

Description

technical field [0001] The invention relates to a new route of cinepazide maleate compound, which belongs to the technical field of medicine. Background technique [0002] Cinepazide Maleate, chemical name (E)-1-{4-[(3,4,5'-trimethoxycinnamoyl)]-1-piperazine}acetylpyrrolidine maleene dihydrochloride , molecular formula: C 22 h 31 N 3 o 5 ·C 4 h 4 o 4 , molecular weight: 533.58, chemical structural formula: [0003] [0004] Cinepazide maleate is a calcium ion channel blocker, by blocking Ca 2+ Transmembrane into vascular smooth muscle cells, relax vascular smooth muscle, dilate cerebral blood vessels, coronary blood vessels and peripheral blood vessels, thereby relieving vasospasm, reducing vascular resistance, and increasing blood flow. By increasing the blood flow of the cerebral vessels and improving the metabolism of the brain, it is clinically applicable to the treatment of cerebrovascular diseases, cardiovascular diseases and peripheral vascular diseases. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185C07C57/145
Inventor 杨明贵
Owner HAINAN MEILAN SMITH KLINE PHARMA
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