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Preparation method of clarithromycin-N-oxide

A technology for clarithromycin and clarithromycin is applied in the field of preparation of clarithromycin-N-oxide, and achieves the effects of cost reduction, easily controllable conditions and high purity

Inactive Publication Date: 2013-06-26
SHANDONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Patent No. 201110030762.2, a Chinese invention patent named "Preparation Method of Levofloxacin-N-Oxide", discloses a preparation of Levofloxacin-N-Oxide Although the methods are all N-oxides, due to the different structures of the oxidized objects, the types of side reactions that may occur are also completely different. The preparation has no reference significance

Method used

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  • Preparation method of clarithromycin-N-oxide
  • Preparation method of clarithromycin-N-oxide
  • Preparation method of clarithromycin-N-oxide

Examples

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Effect test

Embodiment 1

[0040] (1) Take 0.015 mol of clarithromycin raw material with a mass of 11.2 g, put it into a reaction bottle equipped with a condenser, add 500 mL of 50% acetonitrile solution, and stir at a temperature of 80-100 °C until clarithromycin dissolves;

[0041] (2) Add 40mL of 10% hydrogen peroxide solution to the reaction bottle under the condition of 50~60℃, react for 2 hours, add 80mL of 10% hydrogen peroxide solution, react for 2h, add 80mL of 10% hydrogen peroxide solution, and react for 2h, get the reaction solution;

[0042] (3) Evaporate the reaction solution to dryness in a water bath at 100°C, and remove residual H 2 o 2 11.4 g of the residue was obtained, and the residue was recrystallized with 50% acetonitrile as a solvent to obtain clarithromycin-N-oxide.

[0043] The steps of recrystallization are as follows:

[0044] (1) Crystallization: Add 100 times the weight of the residue to 50% acetonitrile, heat to 80°C, stir to dissolve the residue, filter, concentrate th...

Embodiment 2

[0049] Compared with Example 1, the hydrogen peroxide solution with a mass concentration of 10% was added twice, 100 mL each time, and the rest of the operation steps were exactly the same as in Example 1. How many 9.4g crystals are obtained, and the productive rate is 82%. The HPLC method is used to detect the clarithromycin-N-oxide compound obtained by the method of the present invention. figure 2 . The purity of the clarithromycin-N-oxide obtained by the method of the present invention reached 95.8% using the peak area normalization method.

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Abstract

The invention relates to the technical field of medicaments clarithromycin, and particularly relates to a preparation method of clarithromycin-N-oxide. The method comprises the following steps: mixing clarithromycin with a 50% acetonitrile solution, and dissolving the obtained object; adding 40mL of a hydrogen peroxide solution with a mass concentration of 10% under 50-60 DEG C, after reacting for 2 h, adding 80 ml of the hydrogen peroxide solution with a mass concentration of 10%, reacting for 2 h, adding 80 ml of the hydrogen peroxide solution with a mass concentration of 10%, and reacting for 2 h so as to obtain a reaction solution; and carrying out water-bath drying on the reaction solution, removing residual H2O2 so as to obtain residues, and carrying out recrystallization on the residues by taking water as a solvent so as to obtain clarithromycin-N-oxide. No new impurity is introduced, thereby facilitating the follow-up separation operation; through the step-by-step addition of the hydrogen peroxide solution, the progress of the reaction is controlled, the generation of by-products is reduced, the transformation rate of clarithromycin-N-oxide is improved, and the production of impurities is reduced; the productivity is 88.5%, and the cost is reduced; and the product purity is high.

Description

technical field [0001] The invention relates to the technical field of clarithromycin, in particular to a preparation method of clarithromycin-N-oxide. Background technique [0002] Clarithromycin is a macrolide antibiotic, which is the second-generation erythromycin product. It is formed by replacing the 6-hydroxyl in the erythromycin molecule with a methoxyl group. Its antibacterial effect is 1 to 2 times that of erythromycin, and it has inhibitory effect on Gram-positive bacteria such as Staphylococcus aureus, Streptococcus, and Pneumococcus. In addition, clarithromycin also has a significant inhibitory effect on mycobacteria, and is the drug of choice for the treatment of mycobacterium infection in AIDS patients. Compared with erythromycin, clarithromycin is more stable to gastric acid and reduces adverse reactions in the gastrointestinal tract. It has the advantages of high bioavailability, strong tissue penetration, broad antibacterial spectrum and long half-life. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00
Inventor 王维剑李军李海芳谢元超王波王坤张中湖
Owner SHANDONG UNIV
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