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Preparation method of gamithromycin or 13-descladinosylation compound serving as precursor of gamithromycin

A technology of gamimycin and precursors, applied in the direction of preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., to achieve the effect of simple process, high selectivity and high yield

Active Publication Date: 2015-06-10
QILU SYNVA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the productive rate that this inventive process prepares declardinose compound only has 44.4%-52.0%

Method used

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  • Preparation method of gamithromycin or 13-descladinosylation compound serving as precursor of gamithromycin
  • Preparation method of gamithromycin or 13-descladinosylation compound serving as precursor of gamithromycin
  • Preparation method of gamithromycin or 13-descladinosylation compound serving as precursor of gamithromycin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a 250ml autoclave, add gamimycin 7.8g (10mmol) and methanol 20ml, stir to dissolve, add 4mol / L aqueous hydrochloric acid dropwise, adjust the pH between 1.5-2.0, and inject N into the autoclave 2 , keep the pressure at 0.3Mpa, control the temperature at 25°C, stir for 8 hours, add 50ml of dichloromethane and 50ml of water each, adjust the pH=9.8 with 4mol / L sodium hydroxide solution, separate the liquids to obtain the organic phase concentration, add 35ml of acetone to the concentrated residue Stir and crystallize and filter. The filter cake was vacuum-dried at 50°C and white solid B was 5.4g, with a yield of 86.0% and a purity of 99.5%.

Embodiment 2

[0028] In a 250ml autoclave, add 7.4g (10mmol) of 9-deoxy-8α-aza-8α-homoerythromycin A and 20ml of methanol, stir to dissolve, add dropwise 4mol / L hydrochloric acid aqueous solution, and adjust the pH at 1.5 Between -2.0, N 2 , keep the pressure at 0.5Mpa, control the temperature at 30°C, stir for 5 hours, add 50ml of dichloromethane and 50ml of water each, adjust the pH to 9.6 with 4mol / L sodium hydroxide solution, separate the liquids to obtain the organic phase concentration, and add 35ml of ethanol to the concentrated residue Stir and crystallize and filter. The filter cake was 5.0 g of white solid B dried under vacuum at 50°C, with a yield of 83.7% and a purity of 98.4%.

Embodiment 3

[0030] In a 250ml autoclave, add gamimycin 7.8g (10mmol) and acetone 70ml, add 4mol / L sulfuric acid dropwise, adjust the pH between 2.5-3.0, and put N into the autoclave 2 , control the temperature at 30°C, keep the pressure at 0.4Mpa, add 50ml of dichloromethane and 50ml of water after stirring for 8 hours, adjust the pH=9.8 with 4mol / L sodium hydroxide solution, separate the liquids to obtain the organic phase concentration, and add 35ml of ethanol to the concentrated residue Stir and crystallize and filter. The filter cake was vacuum-dried at 50°C and white solid B was 5.1 g, with a yield of 82.0% and a purity of 99.6%.

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PUM

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Abstract

The invention discloses a preparation method of gamithromycin or a 13-descladinosylation compound serving as a precursor of gamithromycin, belonging to the field of chemical synthesis. The method comprises the steps of adding a reaction substrate and a solvent into a high-pressure kettle, wherein the reaction substrate is gamithromycin or the precursor thereof, and the solvent is low-grade amide, low-grade ketone or low-grade alcohol; adding acid, and controlling the pH value of a reaction system at 0.5-5; introducing nitrogen gas to the high-pressure kettle, and keeping the pressure at 0.1-0.8Mpa; and controlling the reaction temperature at 0-35 DEG C and stirring for 1-12 hours. The preparation method is simple in process and high in selectivity, and the yield of gamithromycin or the 13-descladinosylation compound serving as the precursor of gamithromycin is high. Gamithromycin or the precursor thereof contains hydroxyls, ester groups and a plurality of ether bonds; and the reaction substrate of gamithromycin and the precursor thereof in the method disclosed by the invention selectively breaks the ether bonds at the juncture of cladinose and a matrix under an acid condition, but the hydroxyls and the ester groups are unchanged under the reaction condition, so that the selectivity is high.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of gamimycin or its precursor 13-desclardinose compound. Background technique [0002] Gamithromycin CAS: 145435-72-9 The molecular structural formula is: [0003] [0004] Gamithromycin is a new type of second-generation macrolide veterinary antibiotic drug. The synthetic gamithromycin intermediate is the same as the azithromycin synthetic intermediate, which is a ring-expanded derivative obtained after ring-expansion of erythromycin A oxime, except that the two are isomers. Gamithromycin is mainly used to treat bovine infectious diseases caused by bacterial pathogens such as Pasteurella hemolytica, Pasteurella multocida, and histophilia. [0005] In recent years, with the popularization of new equipment and the increase of investment in scientific research in my country, the improvement of drug standards in my country has become more and more in-dep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/00C07H1/00
CPCC07H1/00C07H17/00
Inventor 王秀龙苏玉辉刘全才孔梅吴连勇
Owner QILU SYNVA PHARMA
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