Azithromycin production technology

A technology of azithromycin and production process, applied in the field of drug synthesis, can solve the problems of low final yield, difficult to control the reaction, long process, etc., and achieve the effects of high yield, increased yield, and complete crystallization

Inactive Publication Date: 2015-09-09
HUANGSHI SHIXING PHARMA
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Problems solved by technology

[0004] The current production of azithromycin is to obtain erythromycin 6,9-imine ether through Beckmann rearrangement reaction of erythromycin oxime, and then undergo

Method used

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Embodiment Construction

[0013] The invention provides a kind of azithromycin production process, its step comprises:

[0014] (1) Synthesis of erythromycin oxime: react erythromycin thiocyanate and hydroxylamine at 30-60°C for 10-36 hours, then neutralize with alkali to obtain erythromycin oxime;

[0015] (2) Synthesis of erythromycin A-6,9-imine ether: dissolve the erythromycin oxime obtained in step (1) in the acetone-water system so that the mass ratio of acetone to water is 0.5~0.8:2~2.5 , add methanesulfonyl chloride and sodium hydroxide, react at pH 9.7-10.5, 3-5°C for 3-4 hours, and centrifuge;

[0016] (3) Synthesis of 9-deoxy-9a-aza-9a-homoerythromycin: add the product obtained in step (2) to water, adjust the pH to 5.5-6.5 at 0-5°C, and add potassium borohydride after completely dissolving After 2-4 hours of reaction, add dichloromethane, adjust the pH to 9.5-10.0 and separate the liquid, keep the organic layer, add the organic layer to water and hydrolyze it at pH 1.0-1.5, and adjust the ...

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PUM

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Abstract

The invention provides an azithromycin production technology. The azithromycin production technology comprises (1), erythromycin oxime synthesis, (2), erythromycin A-6,9-iminoether synthesis, (3), 9-deoxo-9a-aza-9a-homoerythromycin synthesis, (4), azithromycin synthesis and (5), refining. The azithromycin production technology realizes strict control of an acetone-water ratio in erythromycin A-6,9-iminoether synthesis, guarantees dispersibility of erythromycin oxime in a system, is convenient for reaction control, improves a yield and can be industrialized easily. In 9-deoxo-9a-aza-9a-homoerythromycin synthesis, pH is controlled in a range of 1.0-1.5 in reduction product acidolysis so that reduction product hydrolysis is thorough, a yield is improved and post-treatment troubles are reduced. In a methylation reaction for azithromycin synthesis, a crystallization water dropwise addition rate and a dropwise addition total amount are strictly controlled so that crystallization is complete, granularity is uniform and an azithromycin yield is improved.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a production process of azithromycin. Background technique [0002] In recent years, due to the rise of β-lactamase strains produced by common respiratory pathogens such as influenza bacillus, pneumococcus, and Moraxella catarrhalis, the increase of other pathogenic microorganisms such as mycoplasma, chlamydia, and Legionella infections, as well as the increase in immunodeficiency patients Mycobacterium avium, The emergence of Toxoplasma infection has brought attention to the clinical application of macrolide antibiotics. [0003] Azithromycin is one of the modified macrolide derivatives. It is a broad-spectrum macrolide antibiotic obtained after modifying the structure of erythromycin. It mainly binds to the bacterial 50S ribosomal subunit to block The translocation of peptides prevents the synthesis of bacterial peptides and achieves antibacterial effects. Azithromycin has the a...

Claims

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Application Information

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IPC IPC(8): C07H17/00C07H1/00
CPCC07H17/00C07H1/00C07H1/06
Inventor 卢元东汪寅华金建平
Owner HUANGSHI SHIXING PHARMA
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