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Preparation method for edaravone

A technology of edaravone and protonic acid, which is applied in the field of preparation of brain protective agent edaravone, can solve the problems of unfavorable industrial production, cumbersome operation process, long reaction time, etc., and achieve the reduction of heating and cooling steps and safe operation Convenience and good product quality

Active Publication Date: 2014-02-19
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The technical problem to be solved by the present invention is that, in order to overcome defects such as the need for high-temperature reflux, longer reaction time, lower yield, more impurities, cumbersome operation process, and unfavorable industrialized production in the existing preparation method of Edaravone, The invention provides a preparation method of Edaravone

Method used

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  • Preparation method for edaravone
  • Preparation method for edaravone
  • Preparation method for edaravone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add phenylhydrazine (490ml, 4.98mol) dropwise into the mixture of ethyl acetoacetate (636ml, 4.98mol) and acetic acid (28.5ml, 0.498mol), stir, control the rate of addition, keep the reaction temperature at 40-45°C, and complete the dropwise addition Afterwards, the reaction was continued for 20 min, water (2000 ml) was added, solids were precipitated, filtered, and dried to obtain 840 g of crude product Edaravone, with a yield of 96.8%, and a product purity of 98.6% through HPLC analysis.

[0034] mp: 127.1-127.9°C.

Embodiment 2

[0036] Add phenylhydrazine (490ml, 4.98mol) dropwise into the mixture of ethyl acetoacetate (636ml, 4.98mol) and acetic acid (285ml, 4.98mol), stir, control the rate of addition, and keep the reaction temperature at 40-45°C. , continued to react for 20min, added water (2000ml), precipitated solid, filtered, and dried to obtain crude product Edaravone 833g, yield 96.0%, product purity 98.8% through HPLC analysis.

[0037] mp: 127.2-128.1°C.

Embodiment 3

[0039]Phenylhydrazine (490ml, 4.98mol) was added dropwise into a mixture of ethyl acetoacetate (636ml, 4.98mol) and hydrochloric acid (500ml, 5.98mol), stirred, and the rate of addition was controlled to keep the reaction temperature at 70°C. After the addition was complete, continue After reacting for 50 minutes, water (2000ml) was added to precipitate a solid, which was filtered and dried to obtain 810g of crude Edaravone with a yield of 93.3%. The purity of the product was analyzed by HPLC to be 97.2%.

[0040] mp: 127.0-128.0°C.

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Abstract

The invention discloses a preparation method for edaravone. The preparation method comprises a step of subjecting hydrazinobenzene and ethyl acetoacetate to a cyclization reaction under a solvent-free condition and action of an acid so as to prepare edaravone, wherein the usage amount of the acid is 0.02 to 10 equivalent of the molar weight of hydrazinobenzene. The preparation method provided by the invention has the advantages of mild conditions, fast reaction, safety, reliability, easy and convenient operation, low cost, almost quantitative completion of the reaction, capacity of obtaining a high purity (greater than 98%) crude product which accords with medicinal standards after simple recrystallization, and suitability for industrial production.

Description

technical field [0001] The invention relates to a preparation method of medicine, in particular to a preparation method of brain protectant edaravone. Background technique [0002] Edaravone (Edaravone), chemical name is 3-methyl-1-phenyl-2-pyrazolin-5-one, and its structural formula is as shown in formula (I): [0003] [0004] Edaravone is a brain protectant developed by Japan's Mitsubishi Pharmaceutical Company, i.e. a free radical scavenger. Clinically, it is mainly used to improve neurological symptoms, activities of daily living and dysfunction caused by acute cerebral infarction. [0005] Studies on the mechanism of action of Edaravone show that it can scavenge free radicals and inhibit lipid peroxidation, thereby inhibiting the oxidative damage of brain cells, vascular endothelial cells, and nerve cells. Preclinical studies have shown that the use of edaravone can prevent the progression of cerebral edema and cerebral infarction, relieve the accompanying neurolo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/26
CPCC07D231/26
Inventor 张福利裘鹏程潘林玉高峰陈梦柯蒋敏王健
Owner SHANGHAI INST OF PHARMA IND CO LTD
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