Pyrazolines compound as well as application and preparation method thereof

A compound, sodium metabisulfite technology, applied in the direction of organic chemistry, etc., can solve problems such as drug quality decline, and achieve the effect of simple method and high yield

Active Publication Date: 2010-08-18
JIANGSU SIMCERE PHARMA +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] As a commonly used clinical drug, Edaravone may produce impurities during its production, storage, and use due to the existence of high-temperature processes such as sterilization, resulting in a decrease in the quality of the drug.
[0006] Most domestic reports on related substances in Edaravone injection are reaction raw mat...

Method used

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  • Pyrazolines compound as well as application and preparation method thereof
  • Pyrazolines compound as well as application and preparation method thereof
  • Pyrazolines compound as well as application and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Weigh 4g of Edaravone, 5g of sodium metabisulfite, 50g of 1,2-propanediol, and 50mL of water, respectively, and place them in an open container.

[0030] The suspension was placed in an oil bath at 50°C for heating and stirring, and was taken out after 96 hours, allowed to cool to room temperature, filtered, and the filtrate was set aside.

[0031] The above-mentioned compound A solution was separated by reverse-phase medium-pressure liquid chromatography, and 103 mg of compound A was prepared, with a yield of 1.4%.

Embodiment 2

[0033] Weigh 100 mg of Edaravone, 50 mg of sodium metabisulfite, 500 mg of 1,2-propanediol, and 1 mL of DMSO, respectively, and place them in an open container.

[0034] The solution was placed in an oil bath at 40°C for heating and stirring. After 168 hours, it was taken out, allowed to cool to room temperature, filtered, and the filtrate was set aside.

[0035] The above compound A solution was separated by reverse-phase high performance liquid chromatography, and 5 mg of compound A was prepared with a yield of 2.7%.

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PUM

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Abstract

The invention relates to a compound having a structure as shown in a specification as well as a preparation method and application thereof. The preparation method comprises the steps of: reacting edaravone, sodium pyrosulfite and 1,2-propylene glycol; placing the solution of the reaction under an environment with the temperature of 35-55 DEG C for 96-168 hours and filtering for later use; and separating the edaravone solution by using a reversed phase high performance liquid chromatography method for preparing 4-(1-hydroxy-2-sulfo-propane-2-yl)-3-methyl-1-phenyl-2-pyrazoline-5-ketone. The compound can be used a comparison product of edaravone impurities and is convenient for controlling edaravone and the content of the edaravone in relevant preparations.

Description

field of invention [0001] The present invention relates to 4-(1-hydroxyl-2-sulfonic acid group-propan-2-yl)-3-methyl-1-phenyl-2-pyrazolin-5-one and its preparation method and use. Background technique [0002] 3-Methyl-1-phenyl-2-pyrazolin-5-one, common name: Edaravone, is a medicine for ischemic stroke, and belongs to free radical scavenger neuroprotective agent, and its structural formula is as shown in formula I Show: [0003] [0004] Formula I [0005] As a commonly used clinical drug, Edaravone may produce impurities during its production, storage, and use due to the existence of high-temperature processes such as sterilization, resulting in a decrease in the quality of the drug. [0006] Most domestic reports on related substances in Edaravone injection are reaction raw materials ethyl acetoacetate and phenylhydrazine, but there are few research reports on related substances in Edaravone injection due to the interaction between Edaravone and excipients. There ar...

Claims

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Application Information

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IPC IPC(8): C07D231/26
Inventor 黄鑫杨士豹周春燕
Owner JIANGSU SIMCERE PHARMA
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