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Gemifloxacin intermediate preparation method

A technology for gemifloxacin and intermediates, applied in the field of preparation of gemifloxacin intermediates, can solve the problems of high cost, difficult operation, few successful production and development, etc., to achieve increased yield, cost saving, and cheap raw materials Effect

Active Publication Date: 2016-05-18
HUAREN PHARMACEUTICAL CO LTD
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Problems solved by technology

[0003] Gemifloxacin is synthesized by "mother core" and "branches". There are many reports on the mother core, and large-scale production has been done in China. The research on the synthesis of gimifloxacin branch chains is still in its infancy in China, and few people have successfully produced and developed them. At present, all intermediates in foreign production processes are purified by column chromatography, which is not easy to operate in industrial production, and the cost is relatively high

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Embodiment 1

[0023] A preparation method of gemifloxacin intermediate, comprising the steps of:

[0024] 1. Synthesis of 4-cyano-1-(N-tert-butoxycarbonyl)pyrrolidin-3-one (3)

[0025] Add 16.8g (0.12mol) of glycine ethyl ester hydrochloride, 150mL of methanol, and 4.9g (0.12mol) of sodium hydroxide into a 500mL three-neck flask, heat and stir at 55-60°C, and add propylene dropwise to the reaction solution Nitrile 8.9mL (0.132mol), after 0.5h dropwise, continue to stir and react at the same temperature for 8h. Heating was stopped, and the resulting compound was not treated. After cooling to room temperature, 26.2 g (0.12 mol) of di-tert-butyl dicarbonate was added, and the reaction was stirred for 1.5 h. The solvent was evaporated under reduced pressure, and the residue was dissolved in 100 mL of ethyl acetate, washed with water (75 mL*2), dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to obtain 29.5 g of light yellow oil 2. Yield: ...

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Abstract

The invention relates to medicine and related fields, and especially relates to a gemifloxacin intermediate preparation method. According to the invention, acrylonitrile and ethyl glycinate hydrochloride are adopted as initial raw materials; through the processes of a nucleophilic addition reaction, amino protection, condensation, reduction protection, oxidation, oximation and deprotection, the gemifloxacin branched-chain intermediate 4-aminomethylpyrrolidin-3-one-O-methyloxime dihydrochloride is obtained. The route is simple; two steps of reactions are eliminated; raw materials are cheap and easy to obtain; and product yield is high. The route does not need column chromatography separation. The method provides a feasible synthesis route for industrial production.

Description

technical field [0001] The invention relates to medicine and related fields, in particular to a preparation method of a gemifloxacin intermediate. Background technique [0002] Gemifloxacin mesylate is the first antibiotic approved for community-acquired pneumonia caused by multidrug-resistant Streptococcus pneumoniae strains (MDRSP). For the treatment of acute bronchitis, chronic bronchitis, upper respiratory tract infection caused by Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus, Haemophilus influenzae or Moraxella catarrhalis and pneumococcus, and Chlamydia pneumoniae Community-acquired pneumonia is also used for urinary system, reproductive system, digestive system, skin and soft tissue infections caused by anaerobic bacteria. Similar to most quinolones, its function is to inhibit the synthesis of bacterial cells and DNA helicase, resulting in the uncontrollable synthesis of mRNA and protein, so that cells no longer divide, thus killing bacteria....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/22
Inventor 郭进冯新光韩泳姜明李继仁邹姗姗
Owner HUAREN PHARMACEUTICAL CO LTD
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