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Method for preparing high-purity moxifloxacin hydrochloride

A moxifloxacin hydrochloride, high-purity technology, applied in the field of drug synthesis, can solve the problems of complicated steps, many materials, difficult to control, etc., and achieve the effect of simple operation and post-processing, energy saving, and simple route

Inactive Publication Date: 2015-11-25
SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] The above routes are complicated in steps, require many materials, and are not suitable for industrialized production. In addition, moxifloxacin hydrochloride is prone to explosive crystallization in the process of crystal formation, and a large amount of crystals are precipitated rapidly, which is difficult to control and wraps a large amount of impurities such as inorganic salts. Requires repeated washing and filtration, resulting in low yield
The filtration process cannot be filtered, so it is difficult to realize industrialization

Method used

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  • Method for preparing high-purity moxifloxacin hydrochloride
  • Method for preparing high-purity moxifloxacin hydrochloride

Examples

Experimental program
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Effect test

Embodiment 1

[0028]1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid-O 3 ,O 4 -Preparation of boron diacetate

[0029] Add 93g of boric acid, 3.3g of anhydrous aluminum trichloride and 500ml of acetic anhydride into the reaction flask, stir evenly, slowly heat up to 85-90°C, stir and react for 1 hour, cool in a water bath, and lower the temperature to 50°C-60°C, Add 323.3 g of ethyl quinolinecarboxylate, and continue to stir and react at a temperature of 85° C. to 90° C. for 3 hours. Followed by HPLC until the reaction was completed (ethyl quinolinecarboxylate was reduced to below 5%), the solvent was evaporated under reduced pressure to obtain an oily substance, the oily substance was slowly added to 8.08L ice water, stirred for 30 minutes to precipitate the crude product, filtered, and the filter cake was watered After washing until neutral, the filter cake was dried under reduced pressure at 60° C. in a drying oven for 8 hours to obtain 402 g of an off-...

Embodiment 2

[0036] 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid-O 3 ,O 4 -Preparation of boron diacetate

[0037] Add 95g of boric acid, 3.3g of anhydrous aluminum trichloride and 500ml of acetic anhydride into the reaction flask, stir evenly, slowly heat up to 85-90°C, stir and react for 1 hour, cool in a water bath, and lower the temperature to 50°C-60°C, Add 323.3 g of ethyl quinolinecarboxylate, and continue to stir and react at a temperature of 85° C. to 90° C. for 3 hours. Followed by HPLC until the reaction is complete (ethyl quinolinecarboxylate is reduced to below 5%), the solvent is evaporated under reduced pressure to obtain an oily substance, the oily substance is slowly added to 8.8L ice water, stirred for 30 minutes to separate out the crude product, filtered, and the filter cake was watered After washing until neutral, the filter cake was dried under reduced pressure at 60° C. in a drying oven for 8 hours to obtain 389 g of off-white s...

Embodiment 3

[0044] 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid-O 3 ,O 4 -Preparation of boron diacetate

[0045] Add 92g of boric acid, 3.2g of anhydrous aluminum trichloride and 500ml of acetic anhydride into the reaction flask, stir evenly, slowly heat up to 85-90°C, stir and react for 1 hour, cool in a water bath, and lower the temperature to 50°C-60°C, Add 323.3 g of ethyl quinolinecarboxylate, and continue to stir and react at a temperature of 85° C. to 90° C. for 3 hours. Followed by HPLC until the reaction is complete (ethyl quinolinecarboxylate is reduced to below 5%), the solvent is evaporated under reduced pressure to obtain an oily substance, the oily substance is slowly added to 7.8L ice water, stirred for 30 minutes to separate out the crude product, filtered, and the filter cake was watered After washing until neutral, the filter cake was dried in a drying oven at 60°C under reduced pressure for 8 hours to obtain 404 g of off-white sol...

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Abstract

The invention discloses a method for preparing high-purity moxifloxacin hydrochloride. The method includes the following steps: boric acid and acetic anhydride are adopted and subjected to a catalytic heating reaction at the presence of aluminium trichloride to generate B(OAc)3; B(OAc)3 and 1-cyclopropyl-6, 7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester are subjected to a heating reaction to obtain chelate; chelate and S,S-2,8-diazabicyclo[4.3.0] nonane are subjected to a nucleophilic substitution reaction at the presence of Et3N; after the reaction, a mixed solvent of petroleum ether, ethyl acetate and N, N-dimethyl formamide is used to remove impurities, and ethyl alcohol and chlorhydric acid treatments are carried out; cooling crystallization is carried out to obtain the moxifloxacin hydrochloride crude product; ethyl alcohol and an aqueous solution are used for crystallization according to the fact that the volume ratio of ethyl alcohol to the aqueous solution is 1:3, so that the high-purity moxifloxacin hydrochloride is obtained. According to the invention, the route is simple and convenient, the operation and post-treatment are simple, the yield is relatively high, the purity is high, and the method is suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a preparation method of high-purity moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin hydrochloride (moxifloxacinhydrochloride), chemical name: 1-cyclopropyl-7-(S,S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro- 8-Methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride is the fourth generation of fluoroquinolone antibacterial drugs. It was first described in the patent EP0350733 that it has a broad-spectrum antibacterial effect. It has been used as an antibacterial drug for humans and animals, and can effectively treat infections caused by various bacteria. The structural formula is as follows: [0003] [0004] The final step in the synthesis of moxifloxacin is the parent core C 7 nucleophilic substitution reaction with branched chain S,S-2,8-diazabicyclo[4.3.0]nonane, in which C 7 -F and C 6 Competitive substitution of -F; in additi...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 孙运贝曲宝慧杨晓晴
Owner SHANDONG LUOXIN PARMACEUTICAL GROUP STOCK CO LTD
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