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A technology of moxifloxacin hydrochloride and a synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of increased amount of impurities and high energy consumption, and achieve the effects of reducing the generation of impurities, saving energy, and mild reaction conditions
Active Publication Date: 2014-12-24
JIANGSU TIANYISHI PHARMA
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[0012] On the basis of WO2005012285, this method directly uses hydrochloric acid to remove chelation, and the substitution reaction still uses a higher reaction tem
Method used
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Embodiment 1
[0033] The preparation of embodiment 1 main ring chelate
[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-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 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%, 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 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
[0037] The preparation of embodiment 3 main ring chelates
[0038] 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 280ml of ice water slowly, Then add 280ml of cold water at 0-5°C, keep it at 0-5°C for 2 hours, 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...
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