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The preparation method of moxifloxacin intermediate

A technology of moxifloxacin and intermediates, applied in new preparation fields, can solve the problems of high price, high cost, complicated raw material preparation process, etc., and achieve the effect of short steps and simple operation

Active Publication Date: 2017-03-22
JIANGSU ALPHA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main problem of this process is that the raw material preparation process is complex and expensive, resulting in high cost of the target product MXC, and this route requires multiple hydrogenations, which is not suitable for industrial production
The most critical thing is that an impurity will be produced in the synthesis of MXC-5, which is not easy to remove, resulting in the low purity of the final product MXC

Method used

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  • The preparation method of moxifloxacin intermediate
  • The preparation method of moxifloxacin intermediate
  • The preparation method of moxifloxacin intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Preparation of MXC-2

[0024] Put 75g of compound MXC-1175g and 85g tetrahydropyrrole into the bottle, add 700ml of toluene and 10g of p-toluenesulfonic acid into the bottle, heat to reflux to separate water, TLC shows that the reaction is stopped after the reaction is completed, and the toluene is concentrated under reduced pressure to dryness. Add 200g of acrylamide, continue heating to 130-135°C and stir to react for 8-10 hours. After the reaction, cool down to 70°C, add 700ml of ethyl acetate, stir and cool down to crystallize, filter and dry to obtain about 152g of MXC-2, HPLC purity 98.6 %

Embodiment 2

[0025] Embodiment 2 MXC-3 ester preparation

[0026] Put 120ml of THF and 6g of sodium borohydride into the bottle, lower the temperature to below -5°C, slowly add 22g of boron trifluoride tetrahydrofuran dropwise, and drop it in about 30 minutes. After dropping, keep warm for 30 minutes below 10 degrees, slowly add 23g of compound MXC-2 dropwise, after dropping, stir at room temperature for 12-15 hours, stop the reaction, concentrate ethanol to dryness under reduced pressure, add 100ml of water to the residue, concentrate under reduced pressure and recover THF Extract with dichloromethane, wash the organic layer with 50ml of saturated brine, add 10g of anhydrous sodium sulfate to the organic layer, dry it with suction and filter, concentrate the filtrate to dryness under reduced pressure, then add 20.3g of MXC-3, which is directly put into the next step without purification.

Embodiment 3

[0027] Embodiment 3 MXC-4 ester preparation

[0028] Put 20g of the compound MXC-3 and 60 ethanol into the kettle, add 0.4g of 10% palladium on carbon, pass in hydrogen after N2 replacement, control the hydrogen pressure of 0.3-0.5MPa, heat to 40 degrees to react, after the end of the central control reaction, After N2 replacement, pressure filtration was performed, and the filtrate was concentrated to dryness under reduced pressure to obtain 11.1 g of MXC-4.

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Abstract

The invention discloses a preparing method for a moxifloxacin intermediate. The preparing method includes the steps that MXC-1 and nafoxidine are subjected to condensation and then react with acrylamide to prepare MXC-2, MXC-2 is subjected to a reduction reaction to prepare MXC-3, MXC-3 is hydrogenated to prepare MXC-4, and finally resolution is conducted to obtain the target product MXC. The method has short steps, and is easy to operate and suitable for industrial mass production.

Description

technical field [0001] The invention provides a new preparation method of a moxifloxacin intermediate, which belongs to the field of medicine and chemical industry. Background technique [0002] Moxifloxacin is a broad-spectrum and active 8-methoxyfluoroquinolone antibacterial drug. Moxifloxacin has shown broad-spectrum antibacterial activity in vitro against Gram-positive bacteria, Gram-negative bacteria, anaerobes, acid-fast bacteria, and atypical microorganisms such as Mycoplasma, Chlamydia, and Legionella. Moxifloxacin is also effective against bacteria resistant to β-lactam and macrolide antibiotics. Moxifloxacin has high activity in vivo as confirmed by experimental animal models of infection. It is precisely because of the good antibacterial effect of moxifloxacin that it has received more and more attention from everyone. The research on the synthesis of this product, especially the synthesis of its key intermediate MXC, has also attracted more and more attention....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 漆志文叶银梅陈立芳万新强徐春涛陈晓佩李兆亮
Owner JIANGSU ALPHA PHARM CO LTD
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