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A kind of synthetic method of moxifloxacin hydrochloride

A technology of moxifloxacin hydrochloride and its synthesis method, which is applied in the direction of organic chemistry, can solve the problems of high energy consumption and increased amount of impurities, and achieve the effects of saving energy, reducing the generation of impurities, and mild reaction conditions

Active Publication Date: 2016-08-17
JIANGSU TIANYISHI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 higher reaction temperature (reflux) temperature, and the energy consumption is higher. In addition, the amount of impurities increases significantly with the progress of the reaction.

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

Examples

Experimental program
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Effect test

Embodiment 1

[0033] The preparation of embodiment 1 main ring chelates

[0034] 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-di Ethyl fluoro-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 slowly Water, then add 480ml of cold water at 0-5°C, keep at 0-5°C for 2 hours, the product precipitates, filters, washes with 480ml of water, and vacuum-dries at 40°C until the water content is 2%, to obtain 152.4g of the main ring chelate.

Embodiment 2

[0035] The preparation of embodiment 2 main ring chelates

[0036] Put 120g of acetic anhydride into the reaction bottle 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 , and then add 210ml of cold water at 0-5°C, keep it at 0-5°C for 2h, the product precipitates, filters, washes with 210ml of water, and vacuum-dries at 50°C until the water content is 2.6%, and 38.2g of the main ring chelate is obtained.

Embodiment 3

[0037] The preparation of embodiment 3 main ring chelates

[0038] Put 100g of acetic anhydride into the reaction bottle 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 280ml of ice water slowly , then add 280ml of cold water at 0-5°C, keep it at 0-5°C for 2h, the product precipitates, filters, washes with 280ml 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 synthetic method of moxifloxacin hydrochloride. The synthetic method comprises the following steps: by taking a primary ring chelate as shown in a formula (I) and (S, S)-2,8-diazabicyclo[4.3.0] nonane as raw materials and taking triethylamine as an acid absorber, carrying out condensation reaction in acetonitrile sufficiently; and concentrating, treating, then dissolving, carrying out acidolysis and salifying, crystallizing, filtering, washing and drying to obtain the moxifloxacin hydrochloride, wherein a weight ratio of the primary ring chelate to acetonitrile to triethylamine to (S, S)-2,8-diazabicyclo[4.3.0] nonane is 1 to (2-10) to (0.08-0.96) to (0.30-0.59). The synthetic method is characterized in that a condensation reaction temperature is larger than and equal to 30 DEG C and lower than 70 DEG C. The synthetic method has the following technical effects that nucleophilic substitution reaction is carried out in acetonitrile at a temperature not lower than 30 DEG C but lower than 70 DEG C, the reaction conditions are gentle, the production of impurities is greatly reduced and the energy resources are saved. After acetonitrile is evaporated, the treatment method is simple and rapid, acidification is carried out in alcohol to obtain moxifloxacin hydrochloride, and thus, the synthetic method is suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing 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. It is used 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 傅雪琦沈羽君
Owner JIANGSU TIANYISHI PHARMA