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Synthesizing method of moxifloxacin hydrochloride

A technology of moxifloxacin hydrochloride and a synthesis method, applied in the field of medicinal chemistry, can solve the problems of difficulty in realizing industrialized production, cumbersome post-processing operations, product loss, etc., and achieve the effects of reducing operation steps, process optimization, and improving selectivity.

Inactive Publication Date: 2011-02-16
河南省健康伟业生物医药研究股份有限公司
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Problems solved by technology

Existing literature has reported the synthetic method (EP550903, EP603887) of moxifloxacin hydrochloride, but yield is not high, and literature description is 80%, but the maximum yield of actual operation can reach 50%, and aftertreatment operation is loaded down with trivial details, causes a large amount of Product loss, only suitable for laboratory synthesis, difficult to achieve industrial production

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  • Synthesizing method of moxifloxacin hydrochloride

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Embodiment Construction

[0016] For a better description of the present invention, examples are as follows:

[0017] 1. Synthesis of quinoline carboxylic acid borane chelate

[0018] Take 86g of acetic anhydride and add it to a three-necked flask, add 3g of zinc chloride as a catalyst, stir at room temperature and slowly add 17.3g of boric acid to keep the temperature stable. After the addition, raise the temperature to 100°C for 3 hours. After the reaction was completed, the temperature was lowered to 70°C, and 83g (1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid) was added and stirred After 10 minutes, the temperature was raised to 100°C and the reaction was stirred for 3 hours. After the reaction was completed, the temperature was lowered to 40° C., then poured into 600 ml of frozen purified water and vigorously stirred. A large amount of solids precipitated, filtered, washed twice with ice water, dried and weighed: 89.5g.

[0019] 2. Synthesis of borane chelate...

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Abstract

The invention belongs to the technical field of pharmaceutical chemistry, relates to the novel preparation method of quinolone medicaments and disclosesa novel synthesizing method of moxifloxacin hydrochloride. The method comprises the following steps of: preparing boric acid ester from boric acid, and reacting the boric acid ester and 8-methoxyquinoline carboxylic acid to form an intermediate I; and in a polar solvent, reacting the intermediate I and (s,s)-octahydro-6H-pyrrole[3,4-b] pyrrole at certain temperature, removing the reaction product from the solvent and curing the reaction product to obtain an intermediate II, hydrolyting the intermediate II in a mixed solvent at certain temperature with the aqueous solution of an inorganic alkali, treating the product with diluted hydrochloric acid to obtain the rough moxifloxacin hydrochloride, and recrystallizing the rough moxifloxacin hydrochloride to obtain the refined moxifloxacin hydrochloride. The method improves the reaction selectivity, avoids the generation of impurity at another selected position, effectively increases the yield of the main product, optimizes the technique and increases the yield to 87 percent. Therefore, the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a new method for preparing quinolones, in particular to a new method for synthesizing moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin hydrochloride is a broad-spectrum and 8-methoxyfluoroquinolone antibacterial drug with antibacterial activity. Moxifloxacin has shown broad-spectrum antibacterial activity in vitro against Gram-positive bacteria, Gram-negative bacteria, anaerobes, acid-fast bacteria and atypical microorganisms such as Mycoplasma, Chlamydia and Legionella. The antibacterial mechanism is to interfere with II and IV topoisomerases. Topoisomerases are key enzymes in the control of DNA topology and in DNA replication, repair and transcription. Existing literature reports the synthetic method (EP550903, EP603887) of moxifloxacin hydrochloride, but yield is not high, and literature description is 80%, but actual operation maximum yield c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
Inventor 张红雨张俊杰于振艳叶乾堂张静芳
Owner 河南省健康伟业生物医药研究股份有限公司
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