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A kind of method for preparing moxifloxacin hydrochloride

A technology of moxifloxacin hydrochloride and ethyl quinoline carboxylate, which is applied in the field of drug synthesis and can solve the problems of low product yield and cumbersome steps

Active Publication Date: 2017-03-22
刘婷婷
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the defects of cumbersome steps and low product yield in the existing method for preparing moxifloxacin hydrochloride, and provide a method suitable for industrial scale production with high yield and simple preparation of moxifloxacin hydrochloride

Method used

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  • A kind of method for preparing moxifloxacin hydrochloride
  • A kind of method for preparing moxifloxacin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A preparation method for moxifloxacin hydrochloride, comprising the following steps:

[0026] Under nitrogen protection, the CuCl 2 6.1g (40mmol), ethylene glycol 6.4g (110mmol), isobutylamine 12.4g (170mmol) and 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy- Add 32.3g (100mmol) of ethyl 4-oxo-3-quinolinecarboxylate into a reaction kettle containing 320mL of methanol, contact and react at 50°C for 3 hours, then raise the temperature to 68°C, add (S,S)- 13.9g (110mmol) of 2,8-diazabicyclo[4.3.0]nonane continued to react for 4 hours, filtered off the insoluble matter by hot filtration (at a temperature of 58°C), added concentrated hydrochloric acid dropwise at room temperature, and adjusted the pH value to 2 , stirred for 2 hours, cooled to -5°C to crystallize, filtered with suction, washed with cold ethanol, and dried in vacuo. Moxifloxacin hydrochloride was 40.7 g of white solid, with a yield of 93.0% and a purity of 99.82% (HPLC area normalization method).

Embodiment 2

[0028] A preparation method for moxifloxacin hydrochloride, comprising the following steps:

[0029] Under nitrogen protection, the CuCl 2 4.6g (30mmol), ethylene glycol 6.4g (110mmol), isobutylamine 14.6g (200mmol) and 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy- Add 32.3g (100mmol) of ethyl 4-oxo-3-quinolinecarboxylate into a reaction kettle containing 320mL of methanol, contact and react at 48°C for 3 hours, then raise the temperature to 70°C, add (S,S)- 2,8-Diazabicyclo[4.3.0]nonane 15.1g (120mmol) continue to react for 4 hours, hot filter (temperature is 60 ℃) to filter out insoluble matter, add concentrated hydrochloric acid dropwise at room temperature, adjust the pH value to 2 , stirred for 2 hours, cooled to -10°C to crystallize, suction filtered, washed with cold ethanol, and dried in vacuo to obtain 40.5 g of moxifloxacin hydrochloride as a white solid with a yield of 92.4% and a purity of 99.79% (HPLC area normalization method).

Embodiment 3

[0031] A preparation method for moxifloxacin hydrochloride, comprising the following steps:

[0032] Under nitrogen protection, the CuCl 2 5.3g (35mmol), ethylene glycol 7g (120mmol), isobutylamine 11.7g (160mmol) and 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4 - 32.3g (100mmol) of ethyl oxo-3-quinolinecarboxylate was added to a reaction kettle containing 320mL of methanol, contacted and reacted at 45°C for 3 hours, then heated to 72°C, and (S,S)-2 , 13.3g (105mmol) of 8-diazabicyclo[4.3.0]nonane continued to react for 4 hours, filtered off the insolubles by hot filtration (at a temperature of 55°C), added dropwise concentrated hydrochloric acid at room temperature, and adjusted the pH value to 2, After stirring for 2 hours, cool down to -5°C to crystallize, filter with suction, wash with cold ethanol, and dry in vacuo to obtain 40.2 g of moxifloxacin hydrochloride as a white solid with a yield of 91.7% and a purity of 99.74% (HPLC area normalization method).

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Abstract

The invention discloses a method for preparing moxifloxacin hydrochloride. The method includes the following steps: in the presence of shielding gas, adding CuCl2, glycol, iso-butylamine and 1-cyclopropyl-6, 7-difluoro-1, 4-dihydro-8-methoxyl-4-oxo-3-quinoline carboxylic ethyl ester into a reaction kettle containing methyl alcohol, performing contact reaction at the temperature of 45-55 DEG C for 3 hours, then heating up to the temperature of 65-80 DEG C, adding (S,S)-2, 8-diazabicyclo [4.3.0] nonane for continuous reaction for 4 hours, performing hot filtration to filter out insoluble matter, dropwise adding concentrated hydrochloric acid at room temperature, regulating the pH value to 2, stirring, cooling to minus 10-minus 5 DEG C prior to devitrification, and performing suction filtration, cold ethanol rinsing and vacuum drying to obtain the moxifloxacin hydrochloride. The method is particularly suitable for industrial scale production, simple in step and high in yield.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a method for preparing moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin hydrochloride (moxifloxacin hydrochloride), is a broad-spectrum and antibacterial activity of 8-methoxy fluoroquinolone antibacterial drugs, can effectively treat the infection caused by a variety of bacteria, showing that it is effective against Gram-positive bacteria and atypical pathogens Has good activity. The chemical name is 1-cyclopropyl-7-(S,S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-8-methoxy-4-oxo Dai-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride, its specific structural formula is as follows: [0003] [0004] Chemical and medical workers have carried out extensive research on the method of synthesizing moxifloxacin hydrochloride, for example, EP0550903 discloses the use of 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4 -Dihydro-3-quinolinecarboxylic a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 许士娜夏昌玲高霞
Owner 刘婷婷