Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthetic method for milbemycin oxime

A synthesis method and technology of mirbe oxime are applied in the synthesis field of semi-synthetic macrolide anthelmintic drug mirbe oxime, can solve the problems of toxic chromium trioxide, heavy metal pollution, many side reactions and the like, and achieve low cost, Less side effects and milder effects

Active Publication Date: 2015-11-18
HUBEI HONCH PHARMA
View PDF3 Cites 7 Cited by
  • Summary
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method for milbemycin oxime
  • Synthetic method for milbemycin oxime
  • Synthetic method for milbemycin oxime

Examples

Experimental program
Comparison scheme
Effect test

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-tetramethylpyridine-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 dropw...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a synthetic method for milbemycin oxime. The method comprises the following steps that 1, an oxidation reaction is performed, wherein milbemycins is used as raw materials, pypocholoride or chlorite is used as an oxidizing agent, piperidines free radical of nitroxide is used as a catalyst, a halide is used as a promoter, all the materials are subjected to the reaction in a dichloromethane solvent at the temperature being minus 5-15 DEG C for 0.5-4 h, and postprocessing is performed on a reaction product to obtain an intermediate product of milbemycin ketone; 2, an oximation reaction is performed, wherein methyl alcohol and 1,4-dioxane are used as a reactive solvent, hydroxylamine hydrochloride is used as an oximation reagent, the reaction is performed at the temperature being 25-35 DEG C for 10-16 h, and postprocessing and purification are performed to obtain milbemycin oxime. According to the method, industrial production of the milbemycin oxime is achieved in China for the first time, and the yield of the obtained product is higher than that of similar products both at home and abroad. Due to the fact that the pypocholoride is used as the oxidizing agent, pyridine nitroxide free radical is used as a catalyst, conditions are mild, few side reactions exist, the yield is high, and the cost is low.

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/22
CPCC07D493/22
Inventor 付光明何福彪张文凯
Owner HUBEI HONCH PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com