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Method for purifying 3-hydroxyclarithromycin

A technology of hydroxy clarithromycin and a purification method, which is applied in the field of purification of 3-hydroxy clarithromycin, can solve the problems of inability to obtain hydrolyzed products and reduced yield, and achieve the effects of high yield, short reaction time and high purity

Inactive Publication Date: 2008-04-30
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Especially for the purification of 3-hydroxy clarithromycin by extraction with ethyl acetate, not only the yield will be greatly reduced but also ethyl acetate is slightly soluble to by-products, and a very pure hydrolyzate cannot be obtained

Method used

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  • Method for purifying 3-hydroxyclarithromycin
  • Method for purifying 3-hydroxyclarithromycin

Examples

Experimental program
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Effect test

Embodiment 1

[0027] 3g of clarithromycin, 80ml of water and 2.4m of 138% concentrated hydrochloric acid, stirred at 25°C for 120min; added dropwise ammonia water to adjust the pH value to 9.0, added sodium chloride until the solution was saturated, extracted with 30ml×3 ethyl acetate: washed with saturated saline; Filtration, distillation under reduced pressure; Recrystallization in acetone / petroleum ether system; Filtration, dry to obtain white needle-like crystal 2.12g (yield 89.7%, purity 95%) at last

Embodiment 2

[0029] 3g of clarithromycin, 80ml of water and 2.4ml of 38% concentrated hydrochloric acid, stirred at 25°C for 120min; added dropwise ammonia water to adjust the pH value to 9.0, white flocculent precipitates precipitated; added sodium chloride until the solution was saturated, and precipitated; suction filtered , washed the filter cake with saturated brine; dried the filter cake, dissolved in ethyl acetate, suction filtered, and dried over anhydrous magnesium sulfate for 12 hours; distilled under reduced pressure, and dried at 40°C to obtain 1.87g of white needle-shaped crystals (yield 79.0%, purity 96.5%)

Embodiment 3

[0031] Mix 2.0g of clarithromycin, 53ml of distilled water and 1.0ml of 38% hydrochloric acid, stir at 30°C for 90min; add dropwise ammonia water to adjust the pH value to 7.0, extract with 15ml ethyl acetate; add dropwise ammonia water to adjust the pH value of the extracted aqueous phase To 8.0, add sodium chloride to saturation, and extract again with 15ml of ethyl acetate × 3; wash twice with saturated sodium bicarbonate solution, twice with saturated sodium chloride solution; dry over anhydrous magnesium sulfate; filter with suction, and distill under reduced pressure; Recrystallize in acetone / petroleum ether system; filter and dry to obtain 1.39g of white needle-like crystals (yield 88%, purity 99.0%)

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Abstract

The invention relates to a novel purity method for 3-hydroxy clarithromycin, and belongs to the synthesis field of pharmaceutical intermediate. The 3-hydroxy clarithromycin can be gained by adopting clarithromycin as the raw material through acid hydrolysis. Through the analysis and the comparison to the physico-chemical properties of the principal product and the by product, the 3-hydroxy clarithromycin is purified by respectively adopting a one-time sedimentation method, a two-time sedimentation method, and a purge method. The invention has the advantages that a synthetic route of clarithromycin with simple operation, high productivity, and low cost is provided, the reaction time of the synthetic route is short, the product productivity is high, the subsequent process is simple and easy to be operated, and the productive efficiency of ketolide antibiotics can be greatly improved.

Description

technical field [0001] The invention relates to a new purification method of 3-hydroxy clarithromycin. 3-Hydroxy clarithromycin can be obtained by hydrolyzing clarithromycin with hydrochloric acid. Through the analysis and comparison of the physical and chemical properties of the main product and by-products, 3-hydroxy clarithromycin was purified by one-time precipitation method, two-time precipitation method and washing method. It belongs to the field of synthesis of pharmaceutical intermediates. Background technique [0002] Ketolide antibiotics have broad-spectrum antibacterial activity and low selection resistance, as well as cross-resistance with other macrolide antibiotics, especially have strong activity against common respiratory pathogens. Telithromycin, as the first clinically applied ketolide antibiotic, has been successfully marketed. However, due to its complex production process and low yield, the current market price is very high and it has not been widely u...

Claims

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Application Information

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IPC IPC(8): C07H17/08
Inventor 庞思平张立敏杨翠于永忠
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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