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Production method of moxifloxacin hydrochloride

A technology for moxifloxacin hydrochloride and its production method, which is applied in the production field of moxifloxacin hydrochloride, can solve the problems of being unsuitable for large-scale industrial production, difficult nucleophilic substitution reaction, and low electron cloud density, and is easy for industrial production and recycling. Convenience and low price effect

Inactive Publication Date: 2015-08-26
INNER MONGOLIA NORTHEAST NO 6 PHARMA GRP CO LTD
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But DCC is a strong carcinogen, DBU is expensive and not suitable for industrialized mass production
[0027] The synthesis of moxifloxacin hydrochloride is essentially the mother core C 7 nucleophilic substitution reaction with branched (S,S)-2,8-diazacyclobicyclo[4,3,0]nonane, although C 7 Located at the para-position of the 4-position carbonyl, the electron cloud density is relatively low, and nucleophilic substitution reactions have occurred, but C 8 The forced electronic effect of the methoxy group lowers the C 7 The leaving activity of -F is not easy to react with nucleophilic substitution reaction; in addition, C 7 -F and C 6 There is also competing substitution between -F, thus further reducing C 7 The role of electron cloud density in this step is very important

Method used

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  • Production method of moxifloxacin hydrochloride
  • Production method of moxifloxacin hydrochloride
  • Production method of moxifloxacin hydrochloride

Examples

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preparation example Construction

[0051] 2) Preparation of moxifloxacin hydrochloride: Add 800g of acetonitrile, 160g of chelate, and 50g of triethylamine into the reaction flask, and drop (S,S)-2,8-diazacyclobicyclo[4, 3,0]nonane in acetonitrile solution ((S,S)-2,8-diazacyclobicyclo[4,3,0]nonane 47g, acetonitrile 100g), after the dropwise addition, react at 25°C for 3 hour, the reaction is complete. Turn on the vacuum pump and concentrate under reduced pressure (vacuum degree -0.04~-0.09MPa). After concentration, add 800g of ethanol, stir to dissolve, add concentrated hydrochloric acid dropwise at a temperature of 25°C, adjust to pH=2, and crystallize at 25°C for 3 hours. Filter, wash with ethanol, and dry under normal pressure at 60°C to obtain 125 g of yellow crystalline solid, yield 75.5%, specific rotation [a] D 20 -126° (standard is -125° to -138°).

[0052] The second embodiment:

[0053] 1) Preparation of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate chelate: t...

experiment example

[0068] In order to investigate the quality of the moxifloxacin hydrochloride produced by the present invention, we have carried out a large number of comparative experiments with various processes, all of which prove that the present invention has advantages in quality or production cost. Especially compared with the relatively close chelation process, positive results have been obtained. Here is just one example:

[0069] The moxifloxacin hydrochloride product of the present invention is compared with the moxifloxacin hydrochloride product of the patent WO2005012285. Analyze by high performance liquid chromatography (HPLC), obtain the description of the accompanying drawings figure 2 and image 3 . in, figure 2 It is the moxifloxacin hydrochloride HPLC spectrogram produced by the present invention; Its experimental data are as table 1:

[0070] Table 1

[0071] Peak table

[0072] Detector A Ch1 293nm

[0073] Peak#

[0074] image 3 It is the HPLC spectr...

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Abstract

The invention discloses a production method of moxifloxacin hydrochloride. The method comprises the following steps: with an intermediate 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester of gatifloxacin and (S,S)-2,8-diazacyclo bicycle[4,3,0] nonane as initial materials, chelating, condensing, and salifying to prepare the moxifloxacin hydrochloride. The production method has the beneficial effects that the production technology is relatively mild, easy to operate, free of a special requirement on equipment, relatively high in yield, and suitable for industrialized mass production.

Description

technical field [0001] The invention relates to a pharmaceutical method, namely a production method of moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin hydrochloride chemical name: 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4aS,7aS)-octahydro-6H-pyrrolo[3,4 -b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid hydrochloride [0003] Structural formula: [0004] [0005] Molecular formula: C 21 h 24 FN 3 o 4 ·HCl [0006] Molecular weight: 437.89 [0007] Moxifloxacin hydrochloride (Moxinoxacin) is a new 8-methoxy fluoroquinolone broad-spectrum antibacterial drug. Its chemical structure is obviously different from other fluoroquinolone varieties. methoxy group. The drug is a new class of drug developed by Bayer Company of Germany. It was launched in Germany for the first time in 1999. It was launched and applied in the United Kingdom, the United States, Mexico and other countries successively. It was launched in China in 2002. This product...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 杨景垣张晓颖沙德福
Owner INNER MONGOLIA NORTHEAST NO 6 PHARMA GRP CO LTD
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