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Preparation method for edaravone

An Edaravone and non-alcoholic technology, which is applied in the field of preparation of Edaravone, can solve problems such as waste of energy consumption, corrosion of equipment, and unsuitability for industrialized production, so as to avoid waste of energy consumption, low cost, and avoid corrosion of equipment Effect

Active Publication Date: 2011-09-14
JIANGSU CHIA TAI FENGHAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Due to the relatively high boiling point and strong acidity of acetic acid, the use of such a process will cause huge waste of energy consumption and equipment corrosion, and is not suitable for industrial production

Method used

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  • Preparation method for edaravone
  • Preparation method for edaravone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the preparation of Edaravone

[0024] In a 1L four-neck round-bottom flask, add 200ml of ethanol, add 100g (0.9247mol) of phenylhydrazine (0.9247mol), 120.3g (0.9247mol) of ethyl acetoacetate and 10ml of acetic acid successively under stirring at room temperature, protect the temperature with nitrogen, and gradually raise the temperature to 75-80 ℃, stop heating after reacting for 1h, continue stirring and cooling to 60℃, add 50ml of n-hexane, cool to 10℃, keep stirring and crystallizing at the temperature for 1h, filter under reduced pressure, wash and filter with 100ml of ethanol, 100ml of n-hexane and 100ml of ethanol in turn The cake was dried under reduced pressure for 3 hours at a pressure of 1.33-3.33kpa and a temperature of 90°C to obtain 151.7g of crude Edaravone with a yield of 94.2% and a purity of 99.39% by HPLC.

Embodiment 2

[0025] Embodiment 2: the preparation of Edaravone

[0026] In a 1L four-neck round-bottom flask, add 150ml of methanol, and then add 100g (0.9247mol) of phenylhydrazine (0.9247mol), 120.3g (0.9247mol) of ethyl acetoacetate and 20g of tartaric acid under stirring at room temperature. ℃, stop heating after reacting for 1h, continue to stir and cool to 60°C, add 80ml of methyl tert-butyl ether, cool to 10°C, keep stirring and crystallizing for 1h at the temperature, filter under reduced pressure, use ethanol 100ml, methyl tert-butyl ether successively Wash the filter cake with 100ml of base ether and 100ml of ethanol, and dry under reduced pressure for 3 hours at a pressure of 1.33-3.33kpa and a temperature of 90°C to obtain 148.4g of crude product Edaravone, with a yield of 92.1% and a purity of 99.55% by HPLC. .

Embodiment 3

[0027] Embodiment 3: the preparation of Edaravone

[0028] In a 5L four-neck round bottom flask, add 1L isopropanol, add 500g (4.624mol) of phenylhydrazine (4.624mol), 601.7g (4.624mol) of ethyl acetoacetate and 50g of tartaric acid successively under stirring at room temperature, protect the temperature with nitrogen, and gradually heat up to 75 ~80°C, stop heating after reacting for 1h, continue to stir and cool to 60°C, add 300ml of methyl tert-butyl ether, cool to 10°C, keep stirring and crystallizing for 1h at the temperature, filter under reduced pressure, use ethanol 500ml, methyl 500ml of tert-butyl ether and 500ml of ethanol washed the filter cake, and at a pressure of 1.33 to 3.33kpa and a temperature of 90°C, dried under reduced pressure for 3h to obtain 753.1g of crude product Edaravone, with a yield of 93.5%. The HPLC detected purity was 99.32%.

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Abstract

The invention discloses a preparation method for edaravone. The preparation method comprises the following steps of: reacting phenylhydrazine with ethyl acetoacetate in an alcohol solvent under the action of a catalyst to prepare the edaravone; and after the reaction, adding a non-alcohol solvent to cool and crystallize to obtain the edaravone crude product. The high-yield and high-purity edaravone is prepared from the phenylhydrazine and the ethyl acetoacetate which serve as the raw materials in the presence of acid serving as the catalyst. The quality of the edaravone product is high; the process is simple; the reaction condition is mild and easy to control; the aftertreatment is simple; the problem of three wastes is avoided; cost is low; and the preparation method is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of Edaravone. Background technique [0002] Edaravone (Edaravone, 3-methyl-1-phenyl-2-pyrazolin-5-one) is a powerful free radical scavenger and antioxidant. Absorbed across the blood-brain barrier. Edaravone is a brain protectant developed by Mitsubishi Chemical Corporation of Japan, which was launched in Japan on June 1, 2001. Its mechanism of action is to remove free radicals increased after ischemia, inhibit lipid peroxidation, and protect tissues. Clinically, this product can be used to improve symptoms such as nerves and daily life behaviors of patients in the acute stage of cerebral infarction, with mild side effects, significant curative effect and good prognosis. Its molecular structural formula is as follows: [0003] [0004] Edaravone was first described in patent US4857542. US4857542 discloses the structure of Edaravone, whic...

Claims

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Application Information

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IPC IPC(8): C07D231/26
Inventor 朱永强王凌燕杨杨黄跃朱勇
Owner JIANGSU CHIA TAI FENGHAI PHARMA
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