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Novel method used for preparing N-methyl moxifloxacin

A technology of moxifloxacin methyl and moxifloxacin hydrochloride, which is applied in organic chemistry and other fields, can solve the problems of high price and achieve the effects of simple operation, cost reduction and mild reaction conditions

Inactive Publication Date: 2015-04-15
YAOPHARMA CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this preparation method also uses a one-step method to obtain the impurity, the methylation reagent methyl iodide it uses is a highly toxic reagent and is expensive, so it is not an ideal preparation method

Method used

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  • Novel method used for preparing N-methyl moxifloxacin
  • Novel method used for preparing N-methyl moxifloxacin
  • Novel method used for preparing N-methyl moxifloxacin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] At room temperature, mix and stir 43.8g of moxifloxacin hydrochloride and 150ml of formic acid, heat up to about 70°C to dissolve, add 40ml of formaldehyde solution with a concentration of 37%, and continue to heat up to 100°C to react until the TLC monitoring raw material point disappears. After the reaction solution was concentrated under reduced pressure, 120ml of 2N hydrochloric acid was added to dissolve it, extracted three times with 80ml of dichloromethane each time, the organic layer was discarded, and the pH value of the aqueous layer was adjusted to 10-11 with 40% sodium hydroxide solution. Cool to 0~5°C, keep warm and crystallize for 0.5h, then filter. The filter cake was dried under reduced pressure at 50-80°C to obtain the target compound. Yield is 86.7%, and purity is 99.1% (HPLC area normalization method), and mass spectrogram sees figure 1 .

Embodiment 2

[0039] At room temperature, mix and stir 43.8g of moxifloxacin hydrochloride and 87.6ml of formic acid, heat up to about 70°C to dissolve, then add 6g of paraformaldehyde, continue to heat up to 100°C to react until the TLC monitoring raw material point disappears. After the reaction solution was filtered, the filtrate was concentrated under reduced pressure and dissolved in 120ml of 2N hydrochloric acid, extracted three times with 80ml of dichloromethane each time, the organic layer was discarded, and the pH value of the aqueous layer was adjusted to 10 with 40% sodium hydroxide solution. ~11. Cool to 0~5°C, keep warm and crystallize for 0.5h, then filter. The filter cake was dried under reduced pressure at 50-80°C to obtain the target compound. The yield was 84.4%, and the purity was 98.9% (HPLC area normalization method).

Embodiment 3

[0041] At room temperature, mix and stir 43.8g of moxifloxacin hydrochloride, 7.5g of ammonium formate and 219ml of formic acid, heat up to about 70°C to dissolve, add 40ml of formaldehyde solution with a concentration of 37%, continue to heat up to 100°C for reaction, and react until TLC monitoring until the raw material point disappears. After the reaction solution was concentrated under reduced pressure, 120ml of 2N hydrochloric acid was added to dissolve it, extracted three times with 80ml of dichloromethane each time, the organic layer was discarded, and the pH value of the aqueous layer was adjusted to 10-11 with 40% sodium hydroxide solution. Cool to 0~5°C, keep warm and crystallize for 0.5h, then filter. The filter cake was dried under reduced pressure at 50-80°C to obtain the target compound. The yield was 88.5%, and the purity was 99.4% (HPLC area normalization method).

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Abstract

The invention relates to a novel method used for preparing N-methyl moxifloxacin. According to the novel method, N-methyl moxifloxacin is obtained via direct methylation of moxifloxacin hydrochloride II. Starting materials of the novel method are cheap and easily available; reaction conditions are mild; and the object product can be obtained via one-step reaction. The novel method is used for preparation of moxifloxacin hydrochloride impurity comparison products, is capable of realizing effective quantification control of the impurities, and is beneficial for increasing of quality of moxifloxacin hydrochloride bulk drug and preparations.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for synthesizing N-methyl impurities of a broad-spectrum antibacterial drug moxifloxacin hydrochloride. Background technique [0002] Moxifloxacin hydrochloride was developed by Bayer and first launched in Germany in September 1999, followed by other European countries, the United States, Japan (2005), and South Korea (2006). Due to the widespread clinical application of quinolone antibiotics in recent years, the problem of bacterial resistance to quinolones has become increasingly serious, and the market is eagerly looking forward to the continuous development of new antibacterial drugs with better efficacy. The listing of moxifloxacin meets this demand. Moxifloxacin is a new generation of fluoroquinolone antibacterial drugs, which has high activity against Gram-positive bacteria and low selectivity for drug-resistant mutations. Quinolone-resistant Gram-p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 裴东游伟张毅张宇
Owner YAOPHARMA CO LTD
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