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Preparation method of moxifloxacin hydrochloride

A technology of moxifloxacin hydrochloride and concentrated hydrochloric acid is applied in the field of preparation of moxifloxacin hydrochloride, and can solve the problems of restricting the industrial production of moxifloxacin hydrochloride, affecting the cost of moxifloxacin hydrochloride, requiring chiral fractionation and the like, and achieving the reaction conditions Mild and easy to control, low cost, not easy to solvent residue effect

Active Publication Date: 2012-05-23
JIANGSU CHIA TAI FENGHAI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] There are problems such as low yield and need for chiral fractionation in the above-mentioned method, which seriously affects the cost of moxifloxacin hydrochloride and restricts the industrial production of moxifloxacin hydrochloride

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of moxifloxacin

[0035] In a 500 mL three-neck round bottom flask, add 300 mL of acetonitrile, and then add 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro -3-quinolinecarboxylic acid 59.0 g (0.2 mol), S,S-2,8-diazabicyclo[4.3.0]nonane 27.8 g (0.22 mol), triethylamine 4.0 g (0.04 mol), Gradually raise the temperature to 80°C, stop heating after reflux reaction for 5 hours, continue to stir and cool to room temperature, stir and crystallize at 0°C for 12 hours, filter, wash the filter cake with 10 mL×3 acetonitrile, at a pressure of 1.33 to 3.33 kpa and a temperature of 50 The crude product moxifloxacin was dried at ℃ to obtain 73.2 g, with a yield of 91.2% and a purity of 98.46% by HPLC.

Embodiment 2

[0036] Embodiment 2: the preparation of moxifloxacin

[0037] In a 2000 mL three-necked round bottom flask, add 1180 mL of tetrahydrofuran, and then add 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro -3-quinolinecarboxylic acid 118.1 g (0.4 mol), S,S-2,8-diazabicyclo[4.3.0]nonane 55.5 g (0.44 mol), N,N-diisopropylethylamine 25.8 g (0.2 mol), gradually warm up to 80°C, stop heating after reflux reaction for 7 hours, continue to stir and cool to room temperature, stir and crystallize at 0°C for 12 hours, filter, wash the filter cake with 20 mL×3 acetonitrile, at a pressure of 1.33 ~3.33 KPa, the temperature was 50°C, and the crude product moxifloxacin was dried to obtain 144.2 g, the yield was 89.8%, and the purity by HPLC was 98.79%.

Embodiment 3

[0038] Embodiment 3: the preparation of moxifloxacin hydrochloride

[0039] In a 3 L three-neck round bottom flask, add 1.46 L of absolute ethanol, add 73.2 g (0.182 mol) of crude product moxifloxacin under stirring at room temperature, gradually raise the temperature to reflux, add 18.5 g (0.182 mol) of concentrated hydrochloric acid, stop heating, After continuing to stir and cool to room temperature, stir and crystallize at 0°C for 12 hours, filter, wash the filter cake with 50 mL×3 absolute ethanol, and dry at a pressure of 1.33 to 3.33 kpa and a temperature of 50°C to obtain the crude product moxifloxacin hydrochloride 72.4 g, the yield is 90.8%, and the HPLC detection purity is 99.87%.

[0040] 1 H-NMR (500MHz, DMSO-d6) δ(ppm): 0.88~0.90 (m,1H), 1.00~1.06 (m,1H), 1.08~1.13 (m,1H), 1.16~1.22 (m,1H) , 1.69~1.84 (m,4H), 2.64~2.66 (m,1H), 2.90~2.94 (m,1H), 3.17-3.19 (m,1H), 3.59 (s,3H), 3.62 (s,1H) , 3.73~3.77 (m,1H), 3.85~3.90 (m,2H), 4.05~4.09 ...

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Abstract

The invention discloses a preparation method of moxifloxacin hydrochloride, comprising the steps of: reacting the 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid and the S,S-2,8-diazabicyclo[4.3.0]nonane to prepare the moxifloxacin in the presence of organic base in organic solvent under the reaction temperature of 60 to 85 DEG C; separating the moxifloxacin, processing the moxifloxacin by concentrated hydrochloric acid in organic solvent under the reaction temperature of 60 to 85 DEG C to obtain the moxifloxacin hydrochloride.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin hydrochloride, 1-cyclopropyl-7-(S,S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluoro-8-methoxy Base-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid hydrochloride) is the fourth generation of fluoroquinolone antibacterial drugs. It has a broad-spectrum antibacterial effect and has been used as an antibacterial drug for humans and animals. It can effectively treat infections caused by various bacteria. Its structural formula is as follows: [0003] [0004] Moxifloxacin is a highly potent antibacterial agent and was first described in patent EP0350733. EP0550903 discloses the (S,S) structure of moxifloxacin, which is shown to be more effective than sparfloxacin and ciprofloxacin against Gram-positive bacteria, including streptococcal pneumonia, Staphylococcus aureus, and Strep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
Inventor 杨杨朱永强王凌燕朱勇
Owner JIANGSU CHIA TAI FENGHAI PHARMA
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