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Synthetic method of moxifloxacin hydrochloride

A synthesis method and technology of moxifloxacin hydrochloride, applied in organic chemistry and other directions, can solve the problems of difficult industrialization, borate ester pollution, harsh reaction conditions, etc., and achieve the effects of eliminating environmental pollution, mild conditions and simple operation.

Inactive Publication Date: 2020-06-23
SHANGYU JINGXIN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In the above condensation reaction process, in order to increase the reaction yield, the boron derivatives were basically chelated to form chelate active reactive functional groups to promote the reaction and improve the yield. However, the reaction conditions after chelation are harsh, and it is still necessary to Removal of chelating groups, long reaction route, cumbersome operation, and difficult industrialization
In addition, there are also some reports of reactions catalyzed by other Lewis acids, but there are problems such as harsh reaction conditions and high temperature. At the same time, industrialization is extremely difficult. The main defect is the great pollution caused by the reaction by-product borate or the by-product is aluminum hydroxide. colloid

Method used

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  • Synthetic method of moxifloxacin hydrochloride
  • Synthetic method of moxifloxacin hydrochloride
  • Synthetic method of moxifloxacin hydrochloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Weigh 8.850g gaticarboxylic acid in a 100mL two-necked flask, replace with argon, add 50mL isopropanol as solvent, then add 3.7857g (S,S)-2,8-diazabicyclo [4.3.0] Nonane, 4.2 mL of triethylamine and 4.2633 g of tetraisopropyl titanate. After the addition was complete, the temperature of the reaction liquid was raised to 100° C. for reaction. After the raw materials were completely consumed, the reaction was terminated, the reaction liquid was cooled to room temperature, transferred to a 100 mL single-necked flask, and the solvent isopropanol was distilled off under reduced pressure to obtain an oily substance. Add 100mL of 10% sodium hydroxide solution, shake, dissolve and continue to stir at 70°C for 2 hours, cool, filter, collect the filtrate, slowly adjust the pH of the filtrate to neutral conditions with dilute hydrochloric acid, and precipitate moxifloxacin monomer. Filter to collect moxifloxacin monomer.

[0039] Take another 250mL beaker, add moxifloxacin monom...

Embodiment 2

[0044]Weigh 8.850g of gaticarboxylic acid in a 100mL two-necked flask, replace with argon, add 50mL of ethanol as a solvent, and then add 3.7857g of (S,S)-2,8-diazabicyclo[4.3 .0] nonane, 4.2 mL triethylamine and 3.42 g tetraethyl titanate. After the addition was complete, the temperature of the reaction liquid was raised to 100° C. for reaction. After the raw materials were completely consumed, the reaction was terminated, the reaction liquid was cooled to room temperature, transferred to a 100 mL single-necked flask, and the solvent isopropanol was distilled off under reduced pressure to obtain an oily substance. Add 100mL of 10% sodium hydroxide solution, shake, dissolve and continue to stir at 70°C for 2 hours, cool, filter, and collect the filtrate. The filter cake is titanium solid waste, and the filtrate is slowly adjusted to a neutral condition with dilute hydrochloric acid. Moxifloxacin monomer was precipitated. Filter to collect moxifloxacin monomer.

[0045] Take...

Embodiment 3

[0047] Weigh 8.850g gaticarboxylic acid in a 100mL two-necked flask, replace with argon, add 50mL isopropanol as solvent, then add 3.7857g (S,S)-2,8-diazabicyclo [4.3.0] Nonane, 4.2 mL of triethylamine and 2.84 g of titanium tetrachloride. After the addition was complete, the temperature of the reaction liquid was raised to 100° C. for reaction. After the raw materials were completely consumed, the reaction was terminated, the reaction liquid was cooled to room temperature, transferred to a 100 mL single-necked flask, and the solvent isopropanol was distilled off under reduced pressure to obtain an oily substance. Add 100mL of 10% sodium hydroxide solution, shake, dissolve and continue to stir at 70°C for 2 hours, cool, filter, collect the filtrate, slowly adjust the pH of the filtrate to neutral conditions with dilute hydrochloric acid, and precipitate moxifloxacin monomer. Filter to collect moxifloxacin monomer.

[0048] Take another 250mL beaker, add moxifloxacin monomer ...

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Abstract

The invention discloses a synthetic method of moxifloxacin hydrochloride. The synthetic method comprises the following steps: under the protection of argon, taking gatifloxacin carboxylate and (S,S)-2,8-diazabicyclo[4.3.0]nonane as raw materials; taking an organic alkali or an inorganic alkali as an acid-binding agent and a Lewis acid as a catalyst; reacting in a certain solvent at a proper temperature; concentrating, processing by alkali liquor, separating out moxifloxacin monomers at an isoelectric point, reacting moxifloxacin monomers with an acid to form salt, concentrating to obtain a moxifloxacin hydrochloride crude product, re-crystallizing, filtering, washing and drying to obtain a refined moxifloxacin hydrochloride finished product. The preparation method is mild in reaction conditions, simple to operate, less in pollution, and high in yield and industrial production can be realized easily.

Description

technical field [0001] The invention relates to medicines in the field of medicine, in particular to a method for synthesizing moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin is the fourth-generation fluoroquinolone drug developed by Bayer in Germany. It is a substance that is almost white crystal powder. It is mainly used in the treatment of upper and lower respiratory tract infections clinically. It has the advantages of producing drug resistance and being effective against common drug-resistant bacteria, with long half-life and less adverse reactions. Its chemical name is 1-cyclopropyl-7-{(S,S)-2,8-diazo-bicyclo[4.3.0]non-8-yl}-6-fluoro-8-methoxy-1 ,4-Dihydro-4-oxo-3-quinolinecarboxylic acid, the molecular formula is C 21 h 24 FN 3 o 4 . [0003] At present about the synthetic method of moxifloxacin hydrochloride mainly contains: [0004] A method for synthesizing moxifloxacin hydrochloride disclosed in European Patent EP550903 "Quinolone-and...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 范锦敏汪平中郑飞顾晋文
Owner SHANGYU JINGXIN PHARMA
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