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Synthesis and purification process of high chiral purity pidotimod

A pidotimod and purity technology, applied in the field of pidotimod, can solve problems such as deviation of results, save time, increase yield, and remove chiral impurities

Active Publication Date: 2022-02-15
BEIJING JINCHENG TAIER PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some chiral impurities are inevitably introduced and produced during the process
Although optical rotation is also used as an indicator of chiral purity in the existing process, the results may be biased due to some human factors or other factors in the detection of optical rotation

Method used

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  • Synthesis and purification process of high chiral purity pidotimod

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 100g of L-thioproline to a 500ml four-necked bottle, add 300ml of hydrochloric acid ethanol, stir and heat to 40°C, react for 5 hours, after the reaction is completed, cool down to 0°C, and filter to obtain L-thioproline ester hydrochloride.

[0033] Add 110 g of the obtained L-thioproline ethyl ester hydrochloride into a 1000 mL reaction flask, stir, add 420 g of ethanol, heat to dissolve, and then add 130 g of cyclohexane dropwise, after the dropwise addition is completed, slowly cool down, and add crystal Seed, stand still, crystallize at 10°C for 10 hours, filter, and dry to obtain L-thioproline ethyl ester hydrochloride with high chiral purity, which is ready for use.

[0034] Add 100g of L-pyroglutamic acid into a 1000ml four-neck flask, stir, add 450ml of methanol, heat to dissolve, after the dissolution is complete, add 450ml of dichloromethane, cool down to 20°C, and crystallize for 12 hours. After the crystallization is completed, L-pyroglutamic acid with...

Embodiment 2

[0038] Add 100g of L-thioproline to a 500ml four-necked bottle, add 300ml of hydrochloric acid ethanol, stir and heat to 40°C, react for 5 hours, after the reaction is completed, cool down to 0°C, and filter to obtain L-thioproline ester hydrochloride.

[0039] Add 109g of the obtained L-thioproline ethyl ester hydrochloride into a 1000mL reaction flask, stir, add 415g of ethanol, heat to dissolve, and then add 130g of cyclohexane dropwise, after the dropwise addition is completed, slowly cool down, add crystal Seed, stand still, crystallize at 25°C for 13 hours, filter, and dry to obtain L-thioproline ethyl ester hydrochloride with high chiral purity, which is ready for use.

[0040] Add 100g of L-pyroglutamic acid into a 1000ml four-necked flask, stir, add 450ml of methanol, heat to dissolve, after the dissolution is complete, add 450ml of dichloromethane, cool to 23°C, and crystallize for 12 hours. After the crystallization is completed, L-pyroglutamic acid with high chira...

Embodiment 3

[0044] Add 100g of L-thioproline to a 500ml four-necked bottle, add 300ml of hydrochloric acid ethanol, stir and heat to 40°C, react for 5 hours, after the reaction is completed, cool down to 0°C, and filter to obtain L-thioproline ester hydrochloride.

[0045] Add 112g of the obtained L-thioproline ethyl ester hydrochloride into a 1000mL reaction flask, stir, add 432g of ethanol, heat to dissolve, and then add 130g of cyclohexane dropwise. Seed, stand still, crystallize at 15°C for 10 hours, filter, and dry to obtain L-thioproline ethyl ester hydrochloride with high chiral purity, which is ready for use.

[0046] Add 100g of L-pyroglutamic acid into a 1000ml four-neck flask, stir, add 450ml of methanol, heat to dissolve, after the dissolution is complete, add 450ml of dichloromethane, cool to 0°C, and crystallize for 12 hours. After the crystallization is completed, L-pyroglutamic acid with high chiral purity is obtained by filtration, which is set aside.

[0047] Weigh 100...

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Abstract

The invention relates to pidotimod, in particular to a process for synthesizing and purifying pidotimod with high chiral purity. The synthesis and purification process is to add L-thioproline ethyl ester hydrochloride and L-pyroglutamic acid to the corresponding single crystal cultivation solution respectively to carry out single crystal cultivation, after condensation, hydrolysis, acidification, Chiral purification to obtain pidotimod with high chiral purity. In the present invention, L-thioproline containing D-thioproline and L-pyroglutamic acid containing D-pyroglutamic acid are cultivated as single crystals to achieve the purpose of separating chiral isomers, and then All chiral isomers present are completely removed by a chiral column. The invention overcomes the defect that the existing technology cannot completely remove the chiral impurities, and finds a simple, effective, safe and environment-friendly method.

Description

technical field [0001] The invention relates to pidotimod, in particular to a process for synthesizing and purifying pidotimod with high chiral purity. Background technique [0002] Pidotimod was developed by an Italian company and obtained a clinical immune booster in 1992, which can promote both non-specific and specific immune responses. Pidotimod can strengthen the phagocytic activity of macrophages and neutrophils, improve their chemotaxis; activate natural killer cells, promote the proliferation of lymphocytes caused by mitogens, and make helper T cells (CD4+) with low immune function Ratio to suppressor T cells (CD8+) increases and returns to normal; promotes cellular immune response by stimulating interleukin-a and r-interferon. In fact, pidotimod has no direct antibacterial and antiviral activity, but it exerts significant antibacterial and antiviral effects by promoting the immune function of the body. Clinically, it is mainly used for recurrent respiratory tract...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/078C07K1/14
CPCC07K5/06139
Inventor 孙滨徐小翠张彤张治中王萌于宇航
Owner BEIJING JINCHENG TAIER PHARMA CO LTD
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