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Method for preparing quinolone derivative

A kind of derivative and quinolone technology, applied in the field of medicinal chemistry, can solve the problems of high price and difficult availability of dimethoxybenzoic acid, and achieve the effects of short synthetic route, simple operation and easy availability of raw materials

Inactive Publication Date: 2015-03-25
安徽美诺华药物化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As proposed in the document J Pharm Biomed Anal 2009, 117, the compound can be synthesized based on the preparation process of moxifloxacin, but the starting material 2,4-difluoro-3,5-dimethoxybenzoic acid used is expensive and not easy to get

Method used

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  • Method for preparing quinolone derivative
  • Method for preparing quinolone derivative
  • Method for preparing quinolone derivative

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preparation example Construction

[0021] A preparation method of compound B, comprising reacting the compound represented by formula I with sodium methoxide, and after the reaction is completed, compound B is obtained through post-processing.

[0022]

[0023] (I) Compound B

[0024] In the step, the reaction solvent is one or more of dimethylformamide, dimethyl sulfoxide, and methanol.

[0025] In said step, the reaction temperature is 80-160°C, more preferably 100°C

[0026] The present invention uses moxifloxacin and sodium methoxide as raw materials, and prepares an impurity (compound B) of moxifloxacin by substitution reaction. The synthetic route is short, the raw materials are easy to obtain, the operation is simple, and the obtained product has high purity, which is convenient to be used as a reference substance Research.

[0027] It should be understood that those skilled in the art can make various modifications and improvements to the present invention based on the contents disclosed h...

Embodiment 1

[0029] Example 1: 1-cyclopropyl-6,8-dimethoxy-1,4-dihydro-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridine Preparation of -6-yl]-4-oxo-3-quinolinecarboxylic acid

[0030] Moxifloxacin (purchased from Anhui Menovo Pharmaceutical Chemical Co., Ltd.) (10 g, 0.025 mol), 100 ml of methanol and sodium methoxide (9 g, 0.167 mol) were put into an autoclave, and the temperature was raised to a reaction temperature of 145° C. for 18 hours. The reaction solution was concentrated under reduced pressure, then 70ml of water was added to adjust the pH value of the solution to 7.5, and extracted with 200ml of dichloromethane. The extracted organic layer was dried with anhydrous sodium sulfate for 1 hour. After drying, the organic layer was concentrated under reduced pressure to obtain 7g of solid. The purity detected by HPLC was 98.5%.

Embodiment 2

[0031] Example 2: 1-cyclopropyl-6,8-dimethoxy-1,4-dihydro-7-[(4aS, 7aS)-octahydro-6H-pyrrolo[3,4-b]pyridine Preparation of -6-yl]-4-oxo-3-quinolinecarboxylic acid

[0032] Moxifloxacin (10 g, 0.025 mol), 100 ml of dimethyl sulfoxide and sodium methoxide (9 g, 0.167 mol) were put into the autoclave, and the temperature was raised to 130° C. for 7 hours. The reaction solution was concentrated under reduced pressure, then 70ml of water was added to adjust the pH value of the solution to 7.5, and extracted with 200ml of dichloromethane. The extracted organic layer was dried with anhydrous sodium sulfate for 1 hour. After drying, the organic layer was concentrated under reduced pressure to obtain 8g of solid. The purity detected by HPLC was 99.2%.

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Abstract

The invention discloses a method for preparing a quinolone derivative, namely a moxifloxacin known impurity compound B. The method comprises the following steps: enabling a compound of a formula I to react with sodium methylate in a polar organic solvent at the temperature of 80 to 160 DEG C, thereby obtaining the compound B. The method disclosed by the invention is short in synthetic route, readily available in raw materials and easy to operate, the prepared product is high in purity, and research of the chemical standard product is conveniently realized.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a quinolone derivative, more specifically a method for preparing moxifloxacin known impurity compound B. Background technique [0002] Moxifloxacin (moxifloxacin), the chemical name is 1-cyclopropyl-7-{(S,S)-2,8-diazo-bicyclo[4.3.0]non-8-yl}-6-fluoro- 8-methoxy-1,4-dihydro-4-oxo-3-quinoline carboxylic acid is a new type of fluoroquinolone antibacterial drug developed by Bayer in Germany. It was first listed in Germany and the United States in 1999, and in China Tablets, capsules and injections are available on the market. This product has the advantages of broad spectrum, high efficiency, low toxicity and no obvious phototoxicity. It is often used to treat respiratory infections (such as pneumonia, chronic sinusitis, chronic bronchitis, etc.). [0003] During the preparation of moxifloxacin, the quinoline skeleton is prone to substitution reactions at other posit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 石建祥邹清华亚罗米尔托曼龚道新
Owner 安徽美诺华药物化学有限公司
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