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Purification method of erythromycin 6,9 imine ether

A purification method, imino ether technology, applied in the field of intermediate erythromycin 6.

Active Publication Date: 2013-09-25
TOPFOND PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the purified azithromycin is of higher purity, there is still a strong urge in the industry to prepare a higher purity product

Method used

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  • Purification method of erythromycin 6,9 imine ether

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] (1) In a 500ml reaction bottle, add 200g chloroform, 50g erythromycin 6,9 imine ether crude product (HPLC purity 89.6%), add 200ml water, and cool down to 5°C.

[0016] (2) Add sodium hydroxide solution, adjust the pH to 10, add 200ml methanol, stir for 5 minutes, let stand to separate the layers, and discard the methanol and water layers.

[0017] (3) Add 400ml of water and 200ml of acetone to the dichloromethane layer, cool down to 1°C, adjust the pH to 3.0 with acetic acid, let the layers stand, discard the dichloromethane layer, add sodium hydroxide solution to the water layer to adjust the pH= 11.2, filtered, and dried at 80°C for 5 hours to obtain 44 g of 6,9 imino ether with a purity of 98.6% by HPLC.

Embodiment 2

[0019] (1) In a 500ml reaction bottle, add 200ml of dichloroethane, 50g of crude erythromycin 6,9 imine ether (HPLC purity 89.6%), add 200ml of deionized water, and cool down to 10°C.

[0020] (2) Add sodium hydroxide solution to adjust the pH to 11, add 200ml of ethanol, stir for 8 minutes, let stand to separate the layers, and discard the ethanol and water layers.

[0021] (3) Add 400ml of water and 200ml of acetone to the dichloroethane layer, lower the temperature to 0-15°C, adjust the pH to 2.0 with acetic acid, let the layers stand, discard the dichloroethane layer, and add sodium hydroxide to the water layer The solution was adjusted to pH=9.5, filtered, and dried at 70° C. for 5 hours to obtain 42 g of 6,9 imino ether with an HPLC purity of 98.7%.

Embodiment 3

[0023] (1) In a 500ml reaction flask, add 100ml of dichloromethane, 100ml of toluene, 50g of crude erythromycin 6,9 imine ether (HPLC purity 89.6%), add 200ml of distilled water, and cool down to 3°C.

[0024] (2) Add sodium hydroxide solution to adjust the pH to 10, add 200ml of acetone, stir for 5 minutes, let stand to separate the layers, and discard the acetone and water layers.

[0025] (3) Add 400ml of water, 100ml of ethanol, and 100ml of acetone to the dichloromethane layer, lower the temperature to 7°C, adjust the pH to 4.0 with acetic acid, let the layers stand, discard the dichloromethane layer, and add sodium hydroxide solution to the water layer Adjust the pH to 12.0, filter, and dry at 90°C for 3 hours to obtain 41 g of 6,9 imino ether with an HPLC purity of 99.1%.

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Abstract

The invention discloses a purification method of erythromycin 6,9 imino ether. The method comprises the following steps: dissolving crude products of erythromycin 6,9 imino ether in water-immiscible low-polar organic solvents, adding water to adjust the mixture to be alkalescence, adding water-miscible high-polar organic solvents, allowing the mixture to stand to stratify, then adding water and water-miscible high-polar organic solvents into the low-polar organic solvents, adjusting the mixture to be acidic, allowing the mixture to stand, removing a low-polar organic layer, adjusting the pH of the water layer to between 9 and 12, and filtering and drying the mixture to generate high-purity erythromycin 6,9 imino ether. The HPLC purity of erythromycin 6,9 imino ether prepared by the technology provided by the invention can achieve more than 98%.

Description

technical field [0001] The invention relates to the technical field of medicine manufacture, in particular to a method for purifying an intermediate erythromycin 6.,9 imine ether of the antibiotic azithromycin. Background technique [0002] Erythromycin 6,9 imine ether, chemical name: (3R, 4R, 5S, 6R, 9R, 10S, 11S, 12R, 13R, 15R)-10-[2,6-dideoxy-3-C-3 -0-methyl--α-L-nucleo-hexapyranosyl)oxy]-6-ethyl-4,5-dihydroxy-3,5,9,11,13,15-hexamethyl- 12-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xyl-hexapyranosyl]oxy]-7,16-dioxa-2-azacyclo [11,2,1]hexadecan-1-en-8-one, American Chemical Abstracts registration number CAS: 99290-97-8, its structural formula is: [0003] [0004] The red pigment 6,9 imine ether is the key precursor for the synthesis of azithromycin. At present, the HPLC purity of the red pigment 6,9 imine ether synthesized by ordinary techniques is about 90%, the purity of azithromycin prepared therefrom is generally about 96%, and the purity of azithromycin after refin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/00C07H1/06
Inventor 王俊臣陈彦龙张卫民王媛焦国华孟利沙藏文生任清华王振兵
Owner TOPFOND PHARMA CO LTD
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