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Preparation method of moxidectin impurities

A technology for moxidectin and impurities, applied in the field of drug synthesis, can solve problems such as no reports yet, and achieve the effects of reasonable route design, strong reaction controllability and simple post-processing

Active Publication Date: 2020-07-03
TLC NANJING PHARMA RANDD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the control of impurity levels has been paid more and more attention by medical workers in the process of drug development and research, but the research on the preparation method of moxidectin impurities has not yet been reported

Method used

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  • Preparation method of moxidectin impurities
  • Preparation method of moxidectin impurities
  • Preparation method of moxidectin impurities

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A preparation method for moxidectin impurities, comprising the following steps:

[0021] (1) Dissolve 5 g of moxidectin in 30 mL of tetrahydrofuran, add 3 g of potassium carbonate, and react the mixture at 100° C. for 1 hour. Thin-layer chromatography shows that the reaction is complete. Concentrate the reaction solution to remove tetrahydrofuran, and purify on a silica gel column to obtain 4.5 g of compound B, yield 90%; MS: 662.3[M+Na]; 1H NMR (400MHz, CDCl 3 ):δ0.72(dd,1H),0.91(d,3H),0.97(d,3H),0.99(d,3H),1.05(d,3H),1.22(d,3H),1.46(s, 3H), 1.63(s, 3H), 1.8(m, 3H), 1.9(d, 1H), 2.07(dd, 1H), 2.2(m, 4H), 2.3~2.4(m, 2H), 2.5~2.7 (m,2H),3.28(d,1H),3.5~3.7(m,3H),3.84(s,3H),4.05(d,1H),4.53(dd,2H),4.79(s,1H), 4.90(t,1H),5.17(d,1H),5.34(dd,2H),5.70(dd,1H),6.10(dt,1H),6.15(s,1H);

[0022] (2) Dissolve 4g of compound B in 70mL of dichloromethane, add 3g of triethylamine and 3.2g of benzoic anhydride at room temperature, react at 25°C for 2 hours, thin layer chromatography sh...

Embodiment 2

[0025] A preparation method for moxidectin impurities, comprising the following steps:

[0026] (1) Dissolve 15.0 g of moxidectin in 30 mL of tetrahydrofuran, add 6.0 g of triethylamine, and react the mixture at 100° C. for 2 hours. Thin layer chromatography shows that the reaction is complete. Purified to obtain 14.2g of compound B, yield 93.3%;

[0027] (2) Dissolve 10 g of compound B in 70 mL of dichloromethane, add 3 g of triethylamine and 4.5 g of methanesulfonyl chloride at room temperature, and react at 40 ° C for 2 hours. Thin layer chromatography shows that the reaction is complete, and water is added to separate the organic After phase, silica gel column purification to obtain 9.5g of compound C, yield 89.20%;

[0028] (3) Dissolve 5.2g of compound C in acetonitrile, add 4.1g of potassium carbonate at room temperature and react at 40°C for 2 hours, thin-layer chromatography shows that the reaction is complete, after concentration to remove tetrahydrofuran, silica ge...

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Abstract

The invention discloses a preparation method of moxidectin impurities, belonging to the field of drug synthesis. The preparation method has the advantages of reasonable reaction route design, accessible raw materials and high operability. According to the method, moxidectin is used as an initial raw material, alkali is added for rearrangement to obtain an EP impurity E, the EP impurity E is subjected to acylation, and elimination is conducted to obtain an EP impurity H, so two EP impurities are obtained through a three-step reaction. The whole route of the invention is reasonable in design, post-treatment is simple, and raw materials are cheap and easy to obtain; the purity of the prepared target products can reach 99.5% or above, and the target products can be used for pharmacological andtoxicological research of moxidectin and used as reference standards for impurity control in the process of medicine production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, in particular to a method for preparing moxidectin impurities. Background technique [0002] Moxidectin (Moxidectin, MXD) is a kind of Streptomyces (Streptomyces. Moxidectin is different from other macrolide antiparasitic drugs ivermetin (IVM) and avermectin (Avermectin, AVM) in that it is a single component with a wider repellent effect. Anthelmintic activity, long-acting, safe and other characteristics, and it has strong anti-parasite activity such as nematodes and arthropods at very low doses. In the mid-1980s, it began to be used as an anthelmintic for animals, and it has been commercialized in Japan. [0003] The English name of Moxidectin is Moxidectin, and its chemical name is [6R,23E,25S(E)]-5-O-DeMethyl-28-deoxy-25-(1,3-diMethyl-1-butenyl)-6, 28-epoxy-23-(MethoxyiMino)MilbeMycinB, with the progress of the times and the improvement of science and technology, people have a fuller understan...

Claims

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Application Information

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IPC IPC(8): C07D493/20
CPCC07D493/20
Inventor 宋化丰王韬胡永铸李君
Owner TLC NANJING PHARMA RANDD CO LTD
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