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Gamithromycin related substance and synthesis and separation method thereof

A technology of gamycin and related substances, applied in the field of gamycin related substances and synthesis and separation thereof, can solve problems such as lack of gamycin structure confirmation, and achieve the effect of improving product purity

Pending Publication Date: 2020-08-14
AMICOGEN CHINA BIOPHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The problem to be solved by the present invention is to provide a kind of related substance of gamimycin in order to overcome the lack of structure confirmation and corresponding synthesis and separation methods of the related substances produced by gamimycin in the synthesis process in the prior art And its synthesis and separation method, the gamimycin related substance (i.e. N-propyl azithromycin) of the present invention is a necessity for the quality control of gamimycin, and the material obtained by the synthesis separation method of the present invention can reach the gram level, to satisfy the market's needs

Method used

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  • Gamithromycin related substance and synthesis and separation method thereof
  • Gamithromycin related substance and synthesis and separation method thereof
  • Gamithromycin related substance and synthesis and separation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] In a 250mL autoclave, add 50mL of ethanol to 5g of demethylated azithromycin, dropwise add 15mL of propionaldehyde, add 3g of 5% Pd / C, replace the air with nitrogen three times, then replace the nitrogen with hydrogen three times, control the hydrogen pressure to 0.3MPa, The hydrogen pressure range is 0.1-0.6Mpa, the temperature of the temperature control system is 35-45°C, and the reaction is 4h;

[0030] Stop the reaction, cool to room temperature, replace the gas in the reactor with nitrogen for three times, filter, wash the filter cake with ethanol 2x10mL; evaporate the ethanol to dryness under reduced pressure, add 50mL DCM and 50mL water, adjust the pH to 10.56 with 1M aqueous sodium hydroxide solution, divide layer; the organic phase was washed with 50 mL of water, and evaporated to dryness to obtain 4.84 g of an oily substance, namely N-propyl azithromycin crude product, with a purity of 84%;

[0031] Separation with a conventional silica gel column: dissolve th...

Embodiment 2

[0033] In a 250mL autoclave, add 25mL of methanol to 5g of demethylated azithromycin, dropwise add 5mL of propionaldehyde, add 2.5g of 10% Pd / C, replace the air with nitrogen three times, then replace the nitrogen with hydrogen three times, and control the hydrogen pressure to 0.1MPa , the temperature of the temperature control system is 20-35°C, and the reaction is 6h;

[0034] Stop the reaction, cool to room temperature, replace the gas in the reactor with nitrogen three times, filter, wash the filter cake with methanol 2x10mL; evaporate the methanol to dryness under reduced pressure, add 50mL DCM and 50mL water, adjust the pH to 9 with 1M aqueous sodium hydroxide solution, divide layer; the organic phase was washed with 50 mL of water, and evaporated to dryness to obtain 4.32 g of an oily substance, namely, the crude product of N-propyl azithromycin with a purity of 73%;

[0035] Separation with a conventional silica gel column: dissolve the crude N-propyl azithromycin obta...

Embodiment 3

[0037] In a 250mL autoclave, add 75mL of isopropanol to 5g of demethylazithromycin, dropwise add 25mL of propionaldehyde, add 5g of 5% Pd / C, replace the air with nitrogen three times, then replace the nitrogen with hydrogen three times, and control the hydrogen pressure to 0.6 MPa, the temperature of the temperature control system is 45-50°C, and the reaction is 10h;

[0038] Stop the reaction, cool to room temperature, replace the gas in the reactor with nitrogen three times, filter, wash the filter cake with isopropanol 2x10mL; evaporate the isopropanol to dryness under reduced pressure, add 50mL DCM and 50mL water, adjust the pH with 1M aqueous sodium hydroxide solution =10.95, separate layers; the organic phase was washed with 50 mL of water, and evaporated to dryness to obtain 4.93 g of an oily substance, namely N-propyl azithromycin crude product, with a purity of 84%;

[0039]Separation with a conventional silica gel column: dissolve the crude N-propyl azithromycin obta...

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Abstract

The invention relates to a gamithromycin related substance, and belongs to the field of chemical synthesis. The substance is characterized in that: the gamithromycin related substance is a compound with a structure shown as a formula I or a salt thereof, and the synthesis method takes demethylated azithromycin as a reaction substrate and lower alcohol as a solvent, puts the reaction substrate andthe solvent into a high-pressure reaction kettle, adds propionaldehyde and palladium carbon, keeps hydrogen pressure under a hydrogen protection condition, controls reaction temperature and performs stirring reaction. The product is a necessary product for gamithromycin quality control, the substance prepared by the synthesis and separation method can reach gram grade, and a foundation is laid forgamithromycin quality control and research of unknown impurities.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a substance related to gamithromycin and its synthesis and separation method. Background technique [0002] Gamithromycin is a second-generation macrolide aza7α antibiotic with a structure shown in formula II. [0003] [0004] Gamithromycin is white to off-white, insoluble in water, stable at high temperature and insensitive to light. The veterinary antibiotic injection ZACTRAN (EMEA CVMP, 2008) developed by France Merial Co., Ltd. was approved by the European Union in September 2007. Used in animals, it has the advantages of fast absorption, low residue in the body, wide distribution in the body, safety and high efficiency, and no adverse reaction reports. Gamithromycin is an azamacrolide with a single propyl group substitution at the 7α position. This special structure is conducive to rapid absorption under physiological pH conditions and long-term action in the target t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/00C07H1/00
CPCC07H17/00C07H1/00
Inventor 陈强许留群杨申永李建国王玲
Owner AMICOGEN CHINA BIOPHARM CO LTD
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