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Edaravone derivative and preparation and detection methods and application thereof

A compound and aqueous solution technology, applied in the field of edaravone derivatives, achieves the effects of simple preparation method, high product purity, and simple detection method

Inactive Publication Date: 2019-01-04
JIANGSU SIMCERE PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are few reports on the related substances produced during the storage of Edaravone raw materials

Method used

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  • Edaravone derivative and preparation and detection methods and application thereof
  • Edaravone derivative and preparation and detection methods and application thereof
  • Edaravone derivative and preparation and detection methods and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation of compound A

[0030] Take 10g of edaravone raw material drug and add methanol 200ml to dissolve, slowly add 50ml of hydrogen peroxide with a mass fraction of 30%, stir at room temperature 20°C for 48 hours, spin off part of the solvent at 10°C, and prepare the solution for later use.

[0031] Then adopt reverse-phase high-performance liquid chromatography to separate above-mentioned solution, chromatographic condition is: chromatographic column is Waters Nova-Pak C18, 6 μm, 190*300mm, mobile phase a is methanol: water: glacial acetic acid=45:55:0.1 , mobile phase b is methanol, flow rate: 20ml / min, column temperature: 20°C, detection wavelength: 244nm, injection volume: 0.5ml. Gradient elution is as follows:

[0032] time (min)

Proportion of mobile phase a (%)

Proportion of mobile phase b (%)

0

100

0

22

100

0

52

36

64

72

36

64

80

100

0

[0033] The prepara...

Embodiment 2

[0045] Embodiment 2: the preparation of compound A

[0046] Take 10 g of Edaravone raw material drug and add 200 ml of acetonitrile to dissolve, slowly add 50 ml of hydrogen peroxide with a mass fraction of 30%, stir at room temperature 20°C for 48 hours, spin off part of the solvent at 10°C, and prepare the solution for later use.

[0047] Then adopt reverse-phase high performance liquid chromatography to separate above-mentioned solution, chromatographic condition is: chromatographic column is Waters Nova-Pak C18, 6 μm, 190*300mm, mobile phase a is water: glacial acetic acid=99.9:0.1, mobile phase b Acetonitrile, flow rate: 20ml / min, column temperature: 20°C, detection wavelength: 244nm, injection volume: 0.5ml. Gradient elution is as follows:

[0048] time (min)

[0049] The preparation solution with a relative retention time of 2.3-2.9 was collected, and the solvent was spin-dried at 10° C. to obtain 5 mg of compound A with a yield of 0.07%.

Embodiment 3

[0050] Embodiment 3: the detection of compound A

[0051] The preparation of sample: precision takes by weighing edaravone crude drug 10mg, is placed in 50ml volumetric flask, dissolves and constant volume with methanol: water: the mixed solution of glacial acetic acid=45:55:0.1, is configured to the content of edaravone The sample is 0.2mg / ml, the temperature is controlled at 4°C, and it is prepared and prepared within half an hour.

[0052] Chromatographic conditions and detection:

[0053] Instrument: Agilent 1200 HPLC

[0054] Chromatographic column: Agilent Eclipse XDB-C18, 4.6*150mm (3.5μm);

[0055] Mobile phase a is methanol:water:glacial acetic acid=45:55:0.1, mobile phase b is methanol, flow rate: 0.8ml / min, column temperature: 20°C, detection wavelength: 244nm, injection volume: 20ml. Gradient elution is as follows:

[0056] time (min)

[0057] Test results: The peak eluting time of compound A was 17.3 min, and the peak eluting time of raw material pheny...

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Abstract

The invention relates to a compound which is shown in the following structure and preparation and detection methods and application of the compound. The preparation method is characterized by comprising the steps that edaravone is dissolved in an organic solvent and then reacts with an aqueous hydrogen peroxide solution, the reversed-phase high-performance liquid chromatography is used for separating an edaravone reaction liquid, and (Z)-2-(3-methy-5-oxygen-1-phenyl-4,5-dihydro-1H-pyrazol-4-radical)-3-[(E)-phenylazo]-2-butenoic acid is prepared. In addition, the invention further provides thedetection method of the compound. The compound can be applied to an edaravone impurity reference substance, and the amount of edaravone raw material medicine and the amount of the compound of the related preparation are conveniently controlled. The compound is shown in the description.

Description

[0001] This application is a divisional application of an invention patent application with an application date of "April 3, 2013" and an application number of "201310116354.8" titled "Edaravone derivatives and their preparation methods, detection methods and uses". field of invention [0002] The present invention relates to an Edaravone derivative, namely (Z)-2-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl) -3-[(E)-phenylazo]-2-butenoic acid, its preparation method, detection method and use. Background technique [0003] Edaravone (compound of formula I) is a neuroprotective agent. The administration of edaravone to patients in the acute stage of cerebral infarction can inhibit the reduction of local cerebral blood flow around the infarction, and make the NAA content in the brain significantly higher than that of the glycerol control group on the 28th day after the onset. Edaravone can scavenge free radicals and inhibit lipid peroxidation, thereby inhibiting the ox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/26G01N30/02
CPCC07D231/26G01N30/02
Inventor 刘雯雯廖明毅张斐许向阳
Owner JIANGSU SIMCERE PHARMA
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