Preparation method and detection method for edaravone dimer and tautomer thereof

A technology of edaravone dimers and tautomers, applied in the field of edaravone dimers, can solve the problems of potential safety hazards in clinical use of drugs, poor solubility of dimers, etc., and achieve safety assurance, The effect of easy operation and easy availability of starting materials

Active Publication Date: 2011-09-14
NANJING CHANGAO PHARMA SCI & TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The dimer has very poor solubility and will precipitate when it reaches a certain concentration in the solution. The precipitated dimer crystals will form insoluble particles or visible foreign matter in the preparation. If injected into the human body, it will cause serious adverse reactions. The fact is that Eda Lavone injections and other preparations are generally subjected to high-temperature sterilization during the preparation process, and dimers are more likely to be produced during the sterilization process, which brings safety hazards to the clinical use of drugs, so it is necessary to The limit of daravone dimer is controlled

Method used

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  • Preparation method and detection method for edaravone dimer and tautomer thereof
  • Preparation method and detection method for edaravone dimer and tautomer thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: the preparation of Edaravone dimer

[0021] Weigh 5.0g of Edaravone and 3.0g of sodium bisulfite, dissolve them in 250ml of water, heat to about 100°C, keep stirring for 24 hours, a red solid gradually precipitates in the reaction solution, cool to room temperature, filter with ordinary filter paper, the solid is Wash with 5ml each of water, methanol, and ethyl acetate, and dry in vacuo at 60°C to obtain 0.2g of light brown powder.

[0022] Structural confirmation: MS (ESI): 347[M+H]+, 369[M+Na]+

[0023] 1H NMR: 11.49, s, 2H (5-OH, 5'-OH); 7.77, m, 4H (11-H, 7-H, 11'-H, 7'-H, J=7.6); 7.46, t, 4H (10-H, 8-H, 10'-H, 8'-H, J=7.6); 7.23, t, 2H (9-H, 9'-H, J=7.6); 2.20, s , 6H(3-CH3, 3'-CH3)

Embodiment 2

[0024] Embodiment 2: the preparation of Edaravone dimer

[0025] Weigh 5.0g of Edaravone and 0.5g of sodium bisulfite, suspend in 500ml of methanol, heat to about 65°C, keep stirring for 72h, a red solid gradually precipitates in the reaction solution, cool to room temperature, filter, and dissolve the solid with water , methanol, and ethyl acetate were washed separately, and after drying, 0.05 g of light brown powder was obtained.

[0026] Structure confirmation: MS (ESI) and 1H NMR data are the same as those in Example 1.

Embodiment 3

[0027] Embodiment 3: the preparation of Edaravone dimer

[0028] Weigh 5.0g of Edaravone and 3.5g of sodium thiosulfate, suspend in 200ml of ethanol, heat to about 80°C, keep stirring for 48h, a red solid gradually precipitates in the reaction solution, cool to room temperature, filter, and dissolve the solid with ethanol , water, methanol, and ethyl acetate were washed with 5ml each, and after vacuum drying, 0.13g of a light brown powder was obtained.

[0029] Structure confirmation: MS (ESI) and 1H NMR data are the same as those in Example 1.

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Abstract

The invention belongs to the pharmaceutical field, and specifically relates to a preparation method and a detection method for edaravone dimers and tautomers thereof. The preparation method is characterized in that edaravone is dissolved in a solvent; a catalyst is added; the mixture is heated and filtered to obtain an insoluble substance; the substance is washed and dried to obtain a product. The detection method adopts a high performance liquid chromatography method. The preparation method of the invention has convenient operation and easily available initial raw materials, and the detection method is applicable to the detection of edaravone dimers in edaravone raw materials and preparation samples.

Description

technical field [0001] The present invention relates to an Edaravone dimer 3,3'-dimethyl-1,1'-diphenyl-1H,1'H-[4,4'-dipyrazole]-5,5 'Diol or its tautomer 3,3'-dimethyl-1,1'-diphenyl-1H,1'H-[4,4'-dipyrazole]-5,5'( Preparation method of 4H, 4'H)-diketone, and detection method thereof. Background technique [0002] Edaravone is developed by Japan's Mitsubishi Tokyo Pharmaceutical Co., Ltd., a kind of brain protectant (free radical scavenger) listed in Japan in June 2001. Its indication is acute cerebral infarction, and it is mainly used to improve acute cerebral infarction. Neurological symptoms, activities of daily living and functional impairment. [0003] Clinical studies of edaravone suggest that N-acetylaspartic acid (NAA) is a marker of specific surviving nerve cells, and its content decreases sharply in the early stage of cerebral infarction. The administration of edaravone to patients in the acute stage of cerebral infarction can inhibit the reduction of local cerebr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/26G01N30/36
Inventor 李战储刚曾滢朱丽君叶海黄海燕李玮晁阳于丽丽
Owner NANJING CHANGAO PHARMA SCI & TECH CO LTD
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