Method for preparing anti-inflammatory and anti-allergic drug deflazacort

A deflucolate, anti-allergic technology, applied in steroids, organic chemistry and other directions, can solve the problems of low 21-position iodine efficiency, cumbersome post-processing, difficult purification, etc., and achieves convenient post-processing, simple operation, and recovery. high rate effect

Inactive Publication Date: 2013-02-27
TIANJIN DERCHEMIST SCI TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The problem to be solved in the present invention: solves the problem of low iodination efficiency and difficult control of the 21-position, and provides an optimized preparation method with simple iodination reaction operation, stable reaction, convenient post-treatment and high yield
In addition, in the replacement reaction, the problems of cumbersome post-treatment and difficult purification are solved, a mild, environmentally friendly and practical preparation method is provided, and a product purification method that meets the standards of the Pharmacopoeia is given

Method used

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  • Method for preparing anti-inflammatory and anti-allergic drug deflazacort

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The first step: the preparation of the 21-position iodo product

[0021] 200g 11β-hydroxy-2'-methyl-5'βH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (1eq), 1600mlCH 2 Cl 2 , 20g anhydrous CaCl 2 +600ml anhydrous CH 3 OH was added to the system (calcium chloride was dissolved in methanol), stirred for 15 minutes, and the system was light yellow and transparent. Add calcium oxide (5eq) to the system, stir for 0.5h, use an ice-salt bath to control the system temperature T=-10℃~0℃, and then add iodine solution (1.2eq of iodine dissolved in 1200ml of Water CH 3 OH solution), slowly add dropwise at the beginning, continue to react at T=-10℃~0℃ for 20h after the dropwise addition, TLC tracking (developer: EA / PE=4), after the reaction is complete, add ammonium chloride solution (340g chloride Dissolve ammonium chloride in 2000ml of water), stir for 0.5h, filter with suction, wash the filter cake once with 500ml of methanol and dry it at 20-30°C to obtain 21-position iodide...

Embodiment 2

[0027] The first step: the preparation of the 21-position iodo product

[0028] 200g 11β-hydroxy-2'-methyl-5'βH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (1eq), 1600mlCH 2 Cl 2 , 15g anhydrous CaCl 2 +600ml anhydrous CH 3 OH was added to the system (calcium chloride was dissolved in methanol), stirred for 15 minutes, and the system was light yellow and transparent. Add calcium oxide (5eq) to the system, stir for 0.5h, use an ice-salt bath to control the temperature of the system T=10℃~15℃, and then add iodine solution (1.5eq iodine dissolved in 30gCaCl 2 +1200ml anhydrous CH 3 OH solution), slowly add dropwise at the beginning, continue to react at T=10℃~15℃ for 5h after the dropwise addition, TLC tracking (developer: EA / PE=4), after the reaction is complete, add ammonium chloride solution (340g chloride Ammonium dissolved in 2000ml of water), stirred for 0.5h, suction filtered, the filter cake was washed once with 500ml of methanol and then dried at 20-30°C to obtain t...

Embodiment 3

[0034] The first step: the preparation of the 21-position iodo product

[0035] 200g 11β-hydroxy-2'-methyl-5'βH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (1eq), 1600mlCH 2 Cl 2 , 15g anhydrous CaCl 2 +600ml anhydrous CH 3 OH was added to the system (calcium chloride was dissolved in methanol), stirred for 15 minutes, and the system was light yellow and transparent. Add calcium oxide (5eq) to the system, stir for 0.5h, use an ice-salt bath to control the system temperature T=10℃~15℃, and then add iodine solution (1.2eq iodine dissolved in 30gCaCl 2 +1200ml anhydrous CH 3 OH solution), slowly add dropwise at the beginning, continue to react at T=10℃~20℃ for 5h after the dropwise addition, TLC tracking (developer: EA / PE=4), after the reaction is complete, add ammonium chloride solution (340g chloride Ammonium dissolved in 2000ml of water), stirred for 0.5h, suction filtered, the filter cake was washed once with 500ml of methanol and then dried at 20-30°C to obtain the 21-p...

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Abstract

The invention relates to a method for preparing an anti-inflammatory and anti-allergic drug deflazacort. The method uses 11 beta-hydroxy-2'-methyl-5' beta H-pregnane-1, 4-diene [17, 16-d] oxazole-3, 20-diketone as a raw material, and comprises three steps of: a 21 site iodination reaction, a replacement reaction-esterification reaction and a post-processing purification. The preparation method provided by the invention solves problems of low 21 site iodination efficiency and uneasy control, and provides an optimal preparation method, in which the iodination reaction has simple operation, stable reaction, convenient post treatment and high yield. In addition, the replacement reaction solves problems of complex post treatment and difficult purification. Therefore, the invention provides a moderate, environment-friendly and feasible preparation method, and a drug purification method satisfying the standards of pharmacopoeia, and is conducive to smooth progress of industrialized green production.

Description

technical field [0001] The invention relates to an optimized preparation method of deflazacort, an anti-inflammatory and anti-allergic drug. Background technique [0002] Deflazacort, a highly effective anti-inflammatory and anti-allergic drug, has been reported at home and abroad, but a simple and efficient preparation method suitable for industrial production has not been reported. Method 1, in the iodation reaction, CaO and AIBN are used to catalyze the iodation reaction to complete, as shown in the literature: Journal of Medicinal Chemistry, 1967, vol.10, p.799-802. After comparative experiments, we found that the disadvantage of this method is that the initiation conditions of AIBN are relatively harsh, and it is difficult to grasp the timing of initiation, and it is closely related to the reaction raw materials, the amount of initiator, the stirring speed, and the dropping temperature, and it is prone to problems that the initiation does not proceed smoothly or the ini...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00
Inventor 张术兵谢延民
Owner TIANJIN DERCHEMIST SCI TECH
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