A kind of synthetic method of milbexime

A synthesis method, the technology of milbexime, which is applied in the field of synthesis of semi-synthetic macrolide anthelmintic drug milbexime, can solve the problems of chromium trioxide toxicity, heavy metal pollution, and many side reactions, and achieve low cost, Less side effects and mild conditions

Active Publication Date: 2016-06-22
HUBEI HONCH PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN103896961A discloses a method for preparing mirbe oxime compounds, which uses pyridinium chlorochromate as an oxidant for oxidation reaction, has many side reactions, and the yield is low, and the chromium trioxide used in the process is toxic
Easy to cause heavy metal pollution

Method used

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  • A kind of synthetic method of milbexime
  • A kind of synthetic method of milbexime
  • A kind of synthetic method of milbexime

Examples

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Embodiment 1

[0023] Contain 5Kg milbemycin (C 31 h 43 o 7 or C 32 h 45 o 7 ) of the raw material 24.7Kg is placed in the reactor, and the spectrogram obtained by the milbemycin liquid chromatography detection used in the present embodiment is as follows figure 1 as shown, figure 1 Among them, the peak at 11.11min is Milbemycin A 3 , the peak at 13.92min is Milbemycin A 4 .

[0024] Add 300g of 2,2,6,6-tetramethylpiperidine-N-oxyl radical into the reaction kettle, add 100L of dichloromethane to dissolve, set the temperature of the refrigeration equipment to 5°C, turn on the refrigeration, and turn on the stirring. Weigh 200g of sodium bromide, dissolve it in 1000ml of deionized water and add it to the reaction solution;

[0025] (2), take by weighing 3.57Kg sodium bicarbonate and 11.76Kg sodium carbonate, add 100L water to dissolve, add 81Kg20% sodium hypochlorite solution, stir well, adjust pH to 10 ± 0.5;

[0026] (3), the oxidant solution is divided into 5 batches and added dro...

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Abstract

The present invention provides a method for synthesizing Milbemycin oxime. The method comprises the following steps. (1) Oxidizing reaction: oxidizing Milbemycin, using hypochlorite or chlorite as oxidizers and piperidine nitrogen oxygen free radicals as the catalyst and halide as the catalyst promoter. The oxidation reaction is conducted in a dichloromethane solvent for 0.5-4 hours at −5-15° C. to produce the intermediate product Milbemycin ketone. (2) Oximation reaction: reacting the Milbemycin ketone with a hydroxylamine hydrochloride oximation agent in a 1,4-dioxane reaction solvent for 10-16 hours at 25-35° C. to obtain Milbemycin oxime. The method provided by the present invention realized the industrial production of Milbemycin oxime for the first time domestically. Moreover, the yield of the prepared product is higher than competing products both at home and abroad.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing a semi-synthetic macrolide anthelmintic drug milbexime. Background technique [0002] Milbemycin Oxime (MilbemycinOxime) is a macrolide anti-endoparasite drug, and it is an oxime derivative of Milbemycin A3 and A4. Milbexime has a broad-spectrum anti-parasitic effect, and has a good killing effect on internal and external parasites, especially nematodes and arthropods. Lee et al. studied the neuropharmacological mechanism of milbexime on the viability of Bloodstrongylus cantonensis and Dirofilaria imimaginum in vitro, and showed that the inhibitory and stimulatory effects of milbexime on the two worms were achieved through gabergic and cholinergic mechanisms . The drug binds to the specific high-affinity site on the target worm cells, which affects the permeability of the cell membrane to Cl-, and then causes the inhibitory neurotransmitte...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/22
CPCC07D493/22
Inventor 付光明何福彪张文凯
Owner HUBEI HONCH PHARMA
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