Method for preparation of moxidectin

A reaction and solution technology, applied in organic chemistry and other directions, can solve the problems of large amount of polar organic solvent, high solvent recovery pressure, complicated operation steps, etc., and achieve the effect of reducing production cost, improving purity and increasing product content.

Active Publication Date: 2015-01-14
NEW FOUNDER HLDG DEV LLC +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in this patent document, there are two resin chromatography in the whole synthesis reaction, the operation steps are more complicated, the usage amount of polar organic solvent is large, and the solvent recovery pressure is relatively high

Method used

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  • Method for preparation of moxidectin

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] In a 1L three-necked reaction flask, put the solid content of Nimoctine (the weight percentage of Nimoctine is 80%, and the molar number is 0.098mol), 0.10mol of imidazole, and 300ml of dichloromethane and stir until dissolved at room temperature , and then dropwise added a solution of dichloromethane (400ml) containing tert-butyldimethylchlorosilane (0.26mol) while maintaining the temperature at 25°C, and stirred at room temperature for 9 hours after the dropwise addition was completed. TLC (thin plate chromatography) detection showed that the reaction of the raw materials was basically complete, and the resulting solution was washed with 1000 ml of purified water, and then dried and dehydrated with anhydrous sodium sulfate.

[0100] Add dimethylsulfoxide (0.11mol) and triethylamine (0.15mol) successively to the dehydrated solution, mix well and cool down to -30°C, add phenoxyphosphoryl dichloride (0.11mol) dropwise dichloromethane (39.56ml) solution, the reaction temp...

Embodiment 2

[0106] In a 1L three-necked reaction flask, put the solid matter of Nimoctine (the weight percentage of Nimoctine in it is 82.5%, and the molar number is 0.14mol), imidazole 0.14mol, and dichloromethane 425ml, and stir at room temperature until Dissolve, then add dropwise a solution of dichloromethane (550ml) containing tert-butyldimethylchlorosilane (0.37mol) while maintaining the temperature at 15°C, and stir at room temperature for 12 hours after the dropwise addition is completed. TLC (thin plate chromatography) detection showed that the reaction of the raw materials was basically complete, and the resulting solution was washed with 1420 ml of purified water, and then dried and dehydrated with anhydrous sodium sulfate.

[0107] Add dimethyl sulfoxide (0.15mol) and triethylamine (0.14mol) successively to the dehydrated solution, mix well and cool down to -30°C, add phenoxyphosphoryl dichloride (0.14mol) dropwise dichloromethane (52ml) solution, control the reaction temperat...

Embodiment 3

[0113] In a 1L three-necked reaction flask, put the solid matter of Nimoctine (the weight percentage of Nimoctine in it is 86%, and the molar number is 0.086mol), imidazole 0.091mol, and dichloromethane 265ml, and stir at room temperature until Dissolve, and then add dropwise a solution of dichloromethane (320ml) containing tert-butyldimethylchlorosilane (0.19mol) while maintaining the temperature at 20°C. After the dropwise addition, stir at room temperature for 8 hours. TLC (thin plate chromatography) detection showed that the reaction of the raw materials was basically complete, and the resulting solution was washed with 880 ml of purified water, and then dried and dehydrated with anhydrous sodium sulfate.

[0114] Add dimethylsulfoxide (0.096mol) and triethylamine (0.094mol) successively to the dehydrated solution, mix well and cool down to -30°C, add phenoxyphosphoryl dichloride (0.088mol) dropwise dichloromethane (25ml) solution, control the reaction temperature at -15°C...

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Abstract

The invention relates to a method for preparation of moxidectin. The method includes subjecting Nemadectin to protective reaction, oxidation reaction, oximation reaction and deprotection reaction in order, thus obtaining moxidectin. Specifically, the protective agent employed in the protective reaction is tert-butyl dimethylchlorosilane, and after the oximation reaction, the solid form crude product obtained by the oximation reaction is subjected to crystallization, and then the deprotection reaction is carried out on the obtained crystal. The method provided by the invention increases the product content, further reduces the difficulty for follow-up utilization of macroporous resin for purification, and improves the column loading amount, reduces the number of column chromatography, maintains or even improves the purity of the final product, and lowers the production cost.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for preparing moxictine. Background technique [0002] The molecular formula for Moxidectin is C 37 h 53 NO 8 , the molecular weight is 639.83, the CAS number is 113507-06-5, and its structural formula is: [0003] [0004] Moxidectin is a broad-spectrum, high-efficiency, new-type macrolide anthelmintic antibiotic widely used in veterinary clinics, especially for nematodes (adults and larvae) and arthropods. The same is true at very low doses. Moxictine has a good safety profile in animals. Moxictine can be obtained by fermenting streptomycin to produce nimoctine, and then using nimoctine as a raw material through a semi-synthetic reaction. [0005] Chinese patent application publication CN101372492A describes the synthesis of moxictine from nimoctine through chemical reaction. In the method, streptomycin is fermented to produce fermented liquid c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/22
CPCC07D493/22
Inventor 何勇崴文婧张洪兰
Owner NEW FOUNDER HLDG DEV LLC
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