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A kind of synthetic 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 low yield, high cost, expensive reagents and the like, and achieve the effects of high yield, mild conditions and simple operation

Active Publication Date: 2016-03-16
CHENGDU CLIMB PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The yields of the preparation methods of moxifloxacin hydrochloride in the prior art are all low, and some experimental methods have the problems of expensive reagents used, high toxicity, and high costs such as chiral resolution. The preparation method with high yield, high purity and suitable for industrial production is very important

Method used

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  • A kind of synthetic method of moxifloxacin hydrochloride
  • A kind of synthetic method of moxifloxacin hydrochloride
  • A kind of synthetic method of moxifloxacin hydrochloride

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Effect test

Embodiment 1

[0026] Embodiment 1: Moxifloxacin hydrochloride synthetic new method, it comprises the following steps:

[0027] Add 280g of acetic anhydride and 120g of glacial acetic acid to the reaction kettle in turn, stir and add 5g of anhydrous zinc chloride; heat up, add 80g of triethyl borate dropwise when the temperature in the reaction kettle is 40°C, and continue to maintain the temperature after the dropwise addition is completed Stir for 3 hours, add 150g gatiy cyclization ester after completion, heat up to 70°C, follow the reaction with TLC until the gatiy cyclization ester is completely converted; The crystalline solid was beaten twice with purified water for 20 minutes each time, the slurry was filtered, then beaten with ethanol for 20 minutes, and centrifuged again, and the obtained solid was dried with hot air at 55°C for 3 hours to obtain the intermediate 1-cyclopropyl- 6,7-Difluoro-8-methoxy-1,4-dihydro-4-oxoquinolinyl-3-carboxylic acid-O3,O4-diacetate borate 137g, yield 8...

Embodiment 2

[0030] Embodiment 2: Moxifloxacin hydrochloride synthetic new method, it comprises the following steps:

[0031] Add 280g of acetic anhydride and 120g of glacial acetic acid in sequence in the reaction kettle, stir and add 5g of anhydrous zinc chloride, raise the temperature, add 120g of triethyl borate dropwise when the temperature in the reaction kettle is 50°C, and continue stirring for 5h after the dropwise addition is completed After the completion, add 150g gatiy cyclization ester, raise the temperature to 75°C, follow the reaction with TLC until the gatiy cyclization ester is completely converted; after the reaction is completed, lower the temperature in the kettle to 25°C and stir for crystallization for 25 hours, then centrifugally filter with a centrifuge, The obtained crystalline solid was beaten twice with purified water for 30 minutes each time, and the slurry was filtered, then beaten with ethanol for 30 minutes, and centrifuged again, and the obtained solid was d...

Embodiment 3

[0034] Embodiment 3: moxifloxacin hydrochloride synthetic new method, it comprises the following steps:

[0035]Add 300g of acetic anhydride and 120g of glacial acetic acid in the reaction kettle in turn, stir and add 5g of anhydrous zinc chloride; heat up, when the temperature in the reaction kettle is 58°C, add 150g of triethyl borate dropwise, and continue stirring for 3.5 h, after the completion, add 150g gatiy cyclization ester, raise the temperature to 90°C, follow the reaction with TLC until the conversion of gatiy cyclization ester is complete; after the reaction is completed, lower the temperature in the kettle to 18°C ​​and stir for crystallization for 28h, centrifuge filtration, and the obtained crystallization Slurry the solid with purified water for 2 times, each time for 23 minutes, filter the slurry, and then use ethanol to make a slurry for 25 minutes, then centrifuge again, and dry the obtained solid with hot air at 58°C for 4 hours to obtain the intermediate 1...

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Abstract

The invention discloses a novel synthesis method of moxifloxacin hydrochloride, belonging to the field of pharmaceutical chemistry. The synthesis method comprises the following steps: sequentially adding acetic anhydride and glacial acetic acid into a reaction kettle, adding anhydrous zinc chloride while stirring, dropwisely adding triethyl borate, stirring to react after finishing the dropwise addition, adding gatifloxacin intermediate, and carrying out after-treatment on the obtained solid to obtain a moxifloxacin hydrochloride intermediate; and in the presence of an organic solvent, reacting the moxifloxacin hydrochloride intermediate with (S,S)-2,8-diazabicyclo[4.3.0]nonane, dropwisely adding concentrated hydrochloric acid, reacting to obtain a moxifloxacin hydrochloride crude product, and recrystallizing with ethanol to obtain the high-purity moxifloxacin hydrochloride. The single impurity content of the moxifloxacin hydrochloride is lower than 0.05%, and the total impurity content is lower than 0.1%; and the method is simple to operate, has the advantages of mild conditions and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a new method for synthesizing moxifloxacin hydrochloride. Background technique [0002] Moxifloxacinhydrochloride (Moxifloxacinhydrochloride), as shown in formula (Ⅴ), chemical name is 1-cyclopropyl-7-(S,S-2,8-diazabicyclo[4.3.0]nonane-8 -yl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinoline carboxylic acid hydrochloride, is the fourth generation of quinolone spectrum antibacterial drugs. Moxifloxacin hydrochloride has shown spectrum antibacterial activity against Gram-positive bacteria, Gram-negative bacteria, anaerobic bacteria, acid-fast bacteria, and atypical microorganisms (such as mycoplasma, chlamydia) in vitro. Moxifloxacin hydrochloride was first launched in Germany in 1999, and in the United States in December of the same year. The dosage forms currently on the market in my country include injections and tablets, which are mainly used to treat patients wit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 叶丁曾同建王晓玲唐锐刘华英
Owner CHENGDU CLIMB PHARMA TECH
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