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Edaravone A-type crystal and preparation method thereof

A technology of edaravone and crystal, which is applied in the new crystal form of 1-phenyl-3-methyl-5-pyrazolone and the field of preparation thereof, can solve the problem of large pollution, few reports of crystal form patents, and high yield. problems such as low rate, to achieve the effect of improving purity, reducing risk, and increasing reaction yield

Active Publication Date: 2014-11-05
JIANGSU CHIA TAI FENGHAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the yield in the preparation process is low and the pollution is large
[0006] Domestic patents on Edaravone mainly focus on process preparation, preparations and indications, and there are few reports on related crystal form patents

Method used

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  • Edaravone A-type crystal and preparation method thereof
  • Edaravone A-type crystal and preparation method thereof
  • Edaravone A-type crystal and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: Preparation of Edaravone type A crystal

[0025] Add 96ml ethanol, 16ml n-hexane, and 32.2g of Edaravone crude product with HPLC purity of 99.0% by ethanol: n-hexane 6:1 ratio in the reaction flask, keep the stirring speed of 300 rev / min, control the solution to be stable to Reflux started at 65°C and the solid dissolved. After stirring for about 30 minutes, start to cool down, increase the stirring speed to 500 rpm, solids start to precipitate at 45°C, stir and crystallize at 10°C for 1 hour, filter, wash the filter cake with ethanol and n-hexane, and dry under reduced pressure at 90°C for 9 hours. 25.6 g of white crystalline product was obtained with a purity of 99.9% and a yield of 79.5%.

[0026] Infrared (IR) spectrum data are: 3456, 3129, 1805, 1601, 1580, 1522, 1497, 1457, 1389, 1367, 1344, 1314, 1303, 1236, 1197, 1153, 1045, 1028, 1016, 917, 804, 766 and 752cm -1 .

[0027] Measure under the following experimental conditions to obtain the powde...

Embodiment 2

[0032] Embodiment 2: Preparation of Edaravone type A crystal

[0033] Add 72ml ethanol, 12ml petroleum ether, and 25.0g of Edaravone crude product with HPLC purity of 99.0% by ethanol: the ratio of petroleum ether 6:1 in the reaction bottle, keep the stirring speed of 300 rev / min, control the solution to be stable to Reflux started at 70°C and the solid dissolved. After stirring for about 30 minutes, start to cool down, increase the stirring speed to 500 rpm, solids start to precipitate at 40°C, stir and crystallize at 10°C for 1 hour, filter, wash the filter cake with a mixture of ethanol and petroleum ether, and dry under reduced pressure at 90°C After 9 hours, 19.0 g of a white crystalline product was obtained with a purity of 99.8% and a yield of 76.2%. Infrared (IR) spectrum and X-powder diffraction pattern are the same as in Example 1.

Embodiment 3

[0034] Embodiment 3: Preparation of Edaravone type A crystal

[0035] Add 150ml of ethanol, 25ml of ether, and 50.0g of Edaravone crude product with a HPLC purity of 99.0% in the reaction flask according to the ratio of ethanol:ether 6:1, keep the stirring speed at 300 rpm, and control the solution to stabilize at 70°C Reflux was initiated and the solid dissolved. After stirring for about 30 minutes, start to lower the temperature, increase the stirring speed to 500 rpm, and start to precipitate solids at 40°C, stir and crystallize at 10°C for 1 hour, filter, wash the filter cake with a mixture of ethanol and ether, and dry under reduced pressure at 90°C for 9 hours, 38.4 g of a white crystalline product was obtained, with a purity of 99.8% and a yield of 76.8%. Infrared (IR) spectrum and X-powder diffraction pattern are the same as in Example 1.

[0036] EFFECT EXAMPLES Properties of Edaravone Form A

[0037] 1. Solubility

[0038] Accurately weigh an appropriate amount o...

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Abstract

The invention discloses an edaravone A-type crystal and a preparation method thereof. The X-ray diffraction pattern of the crystal is basically shown in the figure 1. According to the crystal and the method thereof, related substance of the product can be effectively reduced, the purity is improved, and the reaction yield is increased. The crystal has strengthened stability, and is suitable for storing particularly in high-temperature high-humidity conditions. The crystal has excellent solubility due to its better chemical property and stable crystal distribution. When medicine is prepared, satisfactory dosage accuracy can be achieved, so as to improve the safety of the product and reduce the patient's risk. Therefore, the crystal provided by the invention is suitable for preparing stable medicinal preparation.

Description

technical field [0001] The invention belongs to the field of medicines, and in particular relates to a new crystal form of edaravone whose chemical name is 1-phenyl-3-methyl-5-pyrazolone and a preparation method thereof. Background technique [0002] Edaravone is a brain protective agent (free radical scavenger) in medicine, which is used to treat neuropathy caused by cerebral infarction. Its chemical structural formula is as follows: [0003] [0004] Edaravone (Edaravone, 1-phenyl-3-methyl-5-pyrazolone) is a powerful free radical scavenger and antioxidant. This product is a lipophilic compound and can easily pass through the blood-brain barrier. absorbed. 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 s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/26
Inventor 朱永强丁俊杜柳辉杨杨朱勇
Owner JIANGSU CHIA TAI FENGHAI PHARMA
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