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Improvement of preparation method of moxifloxacin hydrochloride

A technology of moxifloxacin hydrochloride and concentrated hydrochloric acid, applied in the direction of organic chemistry and the like, can solve the problems of restricting the industrial production of moxifloxacin hydrochloride, requiring chiral separation, complicated operation, etc., and achieves reduction of labor intensity, production cost, optical high purity effect

Active Publication Date: 2012-10-17
SHANDONG NEWTIME PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The above method has disadvantages such as complicated operation, chiral resolution and high cost, which seriously restrict the industrialized production of moxifloxacin hydrochloride

Method used

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  • Improvement of preparation method of moxifloxacin hydrochloride
  • Improvement of preparation method of moxifloxacin hydrochloride
  • Improvement of preparation method of moxifloxacin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1 Preparation of Moxifloxacin Hydrochloride

[0035] In a 2000mL three-neck round bottom flask, add 150.00g of acetic anhydride, stir, heat up to 80°C, slowly add 28.00g of boric acid, stir evenly, slowly heat up to 110°C, and stir for 2 hours. Cool down to 60-70°C, add 100.00 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate, The temperature was controlled at 80-90° C. to continue the reaction for 2 hours. TLC detects that the reaction is complete, and it is lowered to room temperature. Add acetonitrile 650mL and trimethylamine 367mL to the reaction solution, stir for 30 minutes, add (S, S)-2,8-diazabicyclo[4.3.0]nonane 39.00g ( 1.00eq), heat to reflux for 3 hours, TLC detects that the reaction is complete, cool down to room temperature, add 400mL of methanol, stir for 30 minutes, add 91mL of concentrated hydrochloric acid dropwise under ice bath to control the temperature at 5-10°C, adjust the pH to 1.0, and continue ...

Embodiment 2

[0036] Embodiment 2 Preparation of Moxifloxacin Hydrochloride

[0037]In a 2000mL three-neck round bottom flask, add 150.00g of acetic anhydride, stir, heat up to 80°C, slowly add 28.00g of boric acid, stir evenly, slowly heat up to 110°C, and stir for 2 hours. Cool down to 60-70°C, add 100.00 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate, Control the temperature at 90-100° C. to continue the reaction for 3 hours. TLC detected that the reaction was complete, cooled to room temperature, added 650 mL of acetonitrile and 592 mL of triethylamine to the reaction solution, stirred for 30 minutes, and added 39.00 g of (S, S)-2,8-diazabicyclo[4.3.0]nonane (1.00eq), heated to reflux for 3 hours, TLC detected that the reaction was complete, lowered to room temperature, added 400mL of methanol, stirred for 30 minutes, added 90mL of concentrated hydrochloric acid dropwise under ice bath to control the temperature at 5-10°C, adjusted the pH to 1....

Embodiment 3

[0038] Example 3 Preparation of Moxifloxacin Hydrochloride

[0039] In a 2000mL three-neck round bottom flask, add 150.00g of acetic anhydride, stir, heat up to 80°C, slowly add 28.00g of boric acid, stir evenly, slowly heat up to 110°C, and stir for 2 hours. Cool down to 60-70°C, add 100.00 g of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylate, Control the temperature at 90-100° C. to continue the reaction for 3 hours. TLC detected that the reaction was complete, cooled to room temperature, added 650 mL of acetonitrile and 592 mL of triethylamine to the reaction solution, stirred for 30 minutes, and added 39.39 g of (S, S)-2,8-diazabicyclo[4.3.0]nonane (1.01eq), heat to reflux for 3 hours, TLC detects that the reaction is complete, cool down to room temperature, stir for 30 minutes, add 90mL of concentrated hydrochloric acid dropwise under ice bath to control the temperature at 5-10°C, adjust the pH to 1.2, continue to stir and crystallize ...

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Abstract

The invention belongs to the medicine synthesis field, which concretely relates to a method for preparing moxifloxacin hydrochloride by one-pot method. The method comprises is characterized in that 1-cyclopropyl-6,7- difluoro-1,4-dihydro-8-methoxyl-4-oxo-3-quinoline carboxylic acid ethyl ester is taken as a raw material, then subjected to a chelating reaction by boron, is subjected to nucleophilic substitution reaction with (S,S)-2,8-diazabicyclo[4.3.0]nonane and an acidifying step to prepare moxifloxacin hydrochloride, and the reaction products can be directly used for reaction in next step without post-treatment or separation. The improvement of the invention has the advantages that the reaction steps can be simplified, the operation is simple and the yield is high, and is adapted to more suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of pharmaceutical synthesis, and in particular relates to an improvement of a method for preparing moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin HydrocHloride, the chemical name is 1-cyclopropyl-7-{S,S-2,8-diazabicyclo[4.3.0]nonan-8-yl}-6-fluoro- 8-Methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride, the structural formula is as follows: [0003] [0004] It is an ultra-broad-spectrum fluoroquinolone antibacterial drug launched by Bayer Company in Germany. Moxifloxacin hydrochloride was first launched in Germany in 1999. It is used to treat upper and lower respiratory tract infections (such as: acute sinusitis, acute exacerbation of chronic bronchitis, etc.) , community-acquired pneumonia, and skin and soft tissue infections) have many advantages, such as strong antibacterial activity, broad antibacterial spectrum, not easy to produce drug resistance and effective against co...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 赵志全王秀娟郭彦玲
Owner SHANDONG NEWTIME PHARMA
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