Method for preparing high-purity 5-oxy(p-nitrobenzoyl)-nemadectin

A technology for nitrobenzoyl and nitrobenzoyl chloride is applied in the field of pharmaceutical chemical synthesis, and can solve the problems of high cost, many separation and purification steps, large solvent consumption and the like, and achieves low cost, improved purity and short production cycle. Effect

Active Publication Date: 2015-08-26
XINYU PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has many separation and purification steps, involves the use of expe

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Put crude 5-oxo(p-nitrobenzoyl)-nimoctine (20 g, purity 88.7%) and 20 mL of methanol into a 250 mL round bottom flask, raise the temperature to 60°C, and stir until it dissolves. 120 mL of deionized water was added dropwise, and then the temperature was lowered by a program of 6 °C per hour, and the temperature was lowered to 15 °C, filtered, and the filter cake was rinsed with 15 °C deionized water. The filter cake was vacuum-dried at 80°C for 20 h to obtain 15 g of high-purity 5-oxo(p-nitrobenzoyl)-nimoctine with a purity of 94.5%.

Embodiment 2

[0027] Put crude 5-oxo(p-nitrobenzoyl)-nimoctine (20 g, purity 88.7%) and 20 mL of n-propanol into a 250 mL round bottom flask, heat up to 80°C, and stir until dissolved. 100 mL of deionized water was added dropwise, and then the temperature was lowered by program, 4 °C per hour, and the temperature was lowered to 10 °C, filtered, and the filter cake was rinsed with 10 °C deionized water. The filter cake was vacuum-dried at 80°C for 20 h to obtain 14.4 g of high-purity 5-oxo(p-nitrobenzoyl)-nimoctine with a purity of 95.4%.

Embodiment 3

[0029] Put crude 5-oxo(p-nitrobenzoyl)-nimoctine (20g, purity 88.7%) and 14mL isopropanol into a 250 mL round bottom flask, heat up to 80°C, and stir until dissolved. 140 mL of deionized water was added dropwise, and then the temperature was lowered by 6 °C per hour, and the temperature was lowered to 10 °C, filtered, and the filter cake was rinsed with 10 °C deionized water. The filter cake was vacuum-dried at 80°C for 20 hours to obtain 16.7 g of high-purity 5-oxo(p-nitrobenzoyl)-nimoctine with a purity of 92.6%.

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Abstract

The invention discloses a method for preparing high-purity 5-oxy(p-nitrobenzoyl)-nemadectin. According to the invention, nemadectin is adopted as a reaction initial raw material, and p-nitrobenzoyl chloride is adopted as an -OH protecting reagent, such that a 5-oxy(p-nitrobenzoyl)-nemadectin crude product is prepared; the 5-oxy(p-nitrobenzoyl)-nemadectin crude product is adopted as a raw material and is mixed with a solvent, such that a solution is prepared; an eluting agent is added, and cooling crystallization is carried out, such that 5-oxy(p-nitrobenzoyl)-nemadectin with higher purity is obtained. The method provided by the invention has the advantages of short crystallization time, low cost, high product purity and high yield. With the method, a basis is provided for the preparation of high-purity moxidectin.

Description

technical field [0001] The invention relates to the field of chemical synthesis of medicines, in particular, it provides a method for preparing high-purity 5-oxygen (p-nitrobenzoyl)-nimoctine. Background technique [0002] Moxidectin is a semi-synthetic macrolide antibiotic produced by the fermentation of Streptomyces blue gray, and it is a derivative of nimoctine. Compared with ivermectin and avermectin, moxidectin has wider anthelmintic activity, long-term effect and safety characteristics due to its single component. [0003] The synthetic route of moxictine is to use nimoctine as the starting material, after 5-OH protection, 23-OH oxidation, removal of protective group and oximation reaction or oximation reaction and removal of protective group Preparation of moxictine. The synthetic route of moxictine is not very complicated, but the main reason why this product is difficult to produce on a large scale is that there is a certain difficulty in the purification of the p...

Claims

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Application Information

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IPC IPC(8): C07D493/22
CPCC07D493/22
Inventor 肖静静丁振东王珍刘思远刘瑞华李为全
Owner XINYU PHARM CO LTD
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