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Pyrazolone derivative, amd application and preparation method of pyrazolone derivative

A preparation and compound technology, applied in the application field of quality control methods, can solve the problems of public reports without compound structure confirmation, quality decline of pharmaceutical preparations, and no method for preparing compounds

Inactive Publication Date: 2013-01-23
NANJING ZHENGFENG INFORMATION TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Because Edaravone may produce impurities in the process of preparation production, storage and use, thereby causing the quality of pharmaceutical preparations to decline, an effective impurity inspection method for Edaravone and related preparations is very important for the control of Edaravone preparations. The quality and guarantee of its clinical efficacy are of great significance
[0005] The prior art does not provide any information related to the new pyrazolone derivatives provided by the present invention, there is neither a public report on the compound and its structural confirmation, nor a report on the method for preparing the compound

Method used

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Embodiment 1

[0019] Embodiment 1: Preparation of the present invention compound 4-(1-nitro-1-sulfonic acid group) ethyl-3-methyl-1-phenyl-2-pyrazolin-5-one

[0020] Weigh 10 g of edaravone, 20 g of cysteine ​​hydrochloride, and 10 g of sodium bisulfite into 4 L of water, and heat in a water bath at 98-100° C. for 24 hours. The reaction was completed, concentrated, filtered, and the filtrate was separated from the compound of the present invention by preparative liquid chromatography, the separated liquid containing the compound of the present invention was collected, and the separated liquid was concentrated to obtain 0.3 g of the compound of the present invention, with a yield of 3%.

[0021] The structure of the product is identified by nuclear magnetic resonance and single crystal X-ray diffraction. The results of nuclear magnetic resonance are as follows:

[0022]

[0023] NMR (DMSO-d 6 )

[0024]

[0025]

Embodiment 2

[0026] Embodiment 2: Determination of 4-(1-nitro-1-sulfonic acid group) ethyl-3-methyl-1-phenyl-2-pyrazolin-5 in Edaravone preparation by high performance liquid chromatography - ketone content

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Abstract

The invention relates to a new pyrazolone derivative of 4-(1-nitro-1-sulfonic group)ethyl-3-methyl-1-phenyl-2-pyrazol-5-ketone. The invention further relates to a method for preparing the new pyrazolone derivative and application of the pyrazolone derivative in an edaravone and related preparation quality control method as an impurity reference substance.

Description

Technical field: [0001] The invention relates to a new pyrazolone derivative, its preparation method, and its application in a quality control method related to a cranial neuroprotective agent edaravone and related preparations. Background technique: [0002] Edaravone is one of pyrazolone derivatives, its chemical name is 3-methyl-1-phenyl-2-pyrazolin-5-one, and its chemical structure is as follows: [0003] [0004] Because Edaravone may produce impurities in the process of preparation production, storage and use, thereby causing the quality of pharmaceutical preparations to decline, an effective impurity inspection method for Edaravone and related preparations is very important for the control of Edaravone preparations. It is of great significance to ensure the quality of the drug and ensure its clinical efficacy. [0005] The prior art does not provide any information related to the new pyrazolone derivatives provided by the present invention, and there is neither a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/26G01N30/02
Inventor 史美耿钱世祥石海云
Owner NANJING ZHENGFENG INFORMATION TECH CO LTD
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