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Novel preparation method of moxifloxacin hydrochloride

A technology for moxifloxacin hydrochloride and salt formation, which is applied in chemical instruments and methods, compounds containing elements of Group 3/13 of the periodic table, organic chemistry, etc. Reaction steps, the effect of reducing the generation of impurities and shortening the reaction time

Active Publication Date: 2014-12-24
JIANGSU TIANYISHI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] On the basis of WO2005012285, this method directly uses hydrochloric acid to remove chelation, and the substitution reaction still uses a relatively high reaction temperature, reflux reaction, and high energy consumption, and the acidification must be carried out after the original solvent, acetonitrile, and alcohol must be evaporated. Operation, in addition, the amount of impurities increases significantly with the progress of the reaction

Method used

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  • Novel preparation method of moxifloxacin hydrochloride
  • Novel preparation method of moxifloxacin hydrochloride
  • Novel preparation method of moxifloxacin hydrochloride

Examples

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Embodiment 1

[0051] The preparation of embodiment 1 main ring chelate

[0052]Put 240g of acetic anhydride into a small reactor and heat to 70°C, slowly add 36g of boric acid between 70-90°C, heat up and reflux for 1 hour, then cool to 70°C, add 120g of 1-cyclopropyl-6,7-difluoro under stirring -Ethyl 1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate, heat up to 100-105°C for 1 hour, cool to 0°C, add 480ml of ice water slowly , then add 480ml of cold water at 0-5°C, keep it at 0-5°C for 2h, the product precipitates, filters, washes with 480ml of water, and vacuum-dries at 40°C until the water content is 2.1%, to obtain 156.6g of the main ring chelate.

Embodiment 2

[0053] The preparation of embodiment 2 main ring chelates

[0054] Put 120g of acetic anhydride into the reaction flask and heat to 70°C, slowly add 12g of boric acid between 70-90°C, heat up and reflux for 1h, then cool to 70°C, add 30g of 1-cyclopropyl-6,7-difluoro- Ethyl 1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate, heat up to 100-105°C for 1 hour, cool to 0°C, add 210ml of ice water slowly, Then add 210ml of cold water at 0-5°C, keep it at 0-5°C for 2 hours, the product precipitates, filters, washes with 210ml of water, and vacuum-dries at 50°C until the water content is 2.6%, to obtain 38.2g of the main ring chelate.

Embodiment 3

[0055] The preparation of embodiment 3 main ring chelates

[0056] Put 100g of acetic anhydride into the reaction flask and heat to 70°C, slowly add 10g of boric acid between 70-90°C, heat up and reflux for 1h, then cool to 70°C, add 20g of 1-cyclopropyl-6,7-difluoro- Ethyl 1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate, heat up to 100-105°C for 1 hour, cool to 0°C, add 200ml of ice water slowly, Then add 200ml of cold water at 0-5°C, keep it at 0-5°C for 2 hours, the product precipitates, filters, washes with 200ml of water, and vacuum-dries at 50°C until the water content is 3.9%, to obtain 26.0g of the main ring chelate.

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Abstract

The invention provides a method for preparing a moxifloxacin intermediate and moxifloxacin hydrochloride, which comprises the following steps: carrying out condensation reaction on main ring chelate disclosed as Formula (I) and (S,S)-2,8-diazabicyclo-[4.3.0]nonane in the presence of an acid acceptor in a solvent, acidifying for salification, crystallizing, filtering, washing and drying to obtain the moxifloxacin hydrochloride. The method is characterized in that the solvent in the condensation reaction is alcohol. The condensation reaction is carried out in the alcohol solvent at the controlled temperature of 30-80 DEG C (preferably lower temperature), so the method has the advantage of mild reaction conditions, greatly reduces the generation of impurities, saves the energy; the alcohol solvent can be directly acidified after sufficient reaction, thereby saving the complex step of removing acetonitrile by evaporation and greatly simplifying the steps; and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin hydrochloride is the fourth generation of fluoroquinolones developed by Bayer AG in Germany. Its chemical name is 1-cyclopropyl-6-fluoro-7-([S,S]-2,8-diazabicyclo[4.3 .0] Non-8-yl)-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate hydrochloride. This product was first launched in Germany in September 1999, and in the United States in December of the same year, for the treatment of acute sinusitis, acute exacerbation of chronic bronchitis, community-acquired pneumonia, and uncomplicated skin infections and skin and soft tissue infections; This product is characterized by almost no photosensitivity reaction, and is a better drug for treating respiratory tract infections. [0003] The synthesis of moxifloxacin hydrochloride reported in the literature mainly contains the following methods. [0004] The synthesis method of moxifloxacin...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07F5/04
CPCC07D471/04C07F5/04
Inventor 傅雪琦沈羽君
Owner JIANGSU TIANYISHI PHARMA
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