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Method for synthesizing pidotimod

A technology of pidotimod and a synthesis method, applied in the field of preparation of pharmaceutical compounds, can solve the problems of low yield and high production cost in the synthesis process, and achieve the effects of low price, low cost and reduced decomposition

Active Publication Date: 2011-11-09
QINGDAO VLAND BIOTECH INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The purpose of the present invention is to provide a synthetic process of pidotimod, which solves the problems of low yield and high production cost in the existing synthetic process

Method used

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  • Method for synthesizing pidotimod
  • Method for synthesizing pidotimod

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Embodiment 1

[0029] Embodiment 1, preparation method of the present invention

[0030] Step 1, weigh 100g of L-thiazolidine-4-carboxylic acid and add it into 400mL of acetone, then add 114g of potassium carbonate and stir for 0.5h.

[0031] Step 2, dissolve 122g of L-pyroglutamyl chloride in 300mL of acetone, then dropwise add it to the solution obtained in step a and stir for 2h.

[0032] Step 3, filter, dissolve the filter cake in 500mL of water, ice-bath to 0-10 degrees, acidify the above solution with concentrated hydrochloric acid to PH = 2, a white precipitate is formed, continue to stir for 1 hour.

[0033] Step 4, filtering and drying. The crude product of pidotimod was obtained.

[0034] Step 5, the crude product of pidotimod is recrystallized with water, filtered, dried, and weighed to obtain 165g of refined pidotimod with a yield of 90%

Embodiment 2

[0035] Embodiment 2. preparation method of the present invention

[0036] Step 1, weigh 100g of L-thiazolidine-4-carboxylic acid and add it into 500mL of acetone, then add 96g of sodium carbonate and stir for 0.5h.

[0037] Step 2, dissolve 166g of L-pyroglutamyl chloride in 400mL of acetone, then dropwise add it to the solution obtained in step a and stir for 2h.

[0038] Step 3, filter, dissolve the filter cake in 500mL of water, ice-bath to 0-10 degrees, acidify the above solution with concentrated hydrochloric acid to PH = 2, a white precipitate is formed, continue to stir for 1 hour.

[0039] Step 4, filtering and drying. The crude product of pidotimod was obtained.

[0040] In step 5, the crude product of pidotimod was recrystallized with water, filtered, dried, and weighed to obtain 163g of refined pidotimod with a yield of 89%.

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Abstract

The invention relates to a method for synthesizing pidotimod, which comprises the following steps of: mixing L-thiazolidine-4-carboxylic acid and an acid binding agent in anhydrous acetone; dripping an anhydrous acetone solution of L-pyroglutamic acyl chloride; after the reaction is finished, filtering; dissolving a filter cake in water, acidifying, and filtering to obtain a coarse product; and drying the coarse product, and recrystallizing to obtain the pidotimod.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical compound, in particular to a synthesis method of an immune enhancer pidotimod. Background technique [0002] Pidotimod (pidotimod) was developed by the Italian company Poli industria chimica S.P.A in the 1980s and was approved for clinical use in 1993. It is a synthetic immune booster with a structure similar to that of a dipeptide. Its chemical name is For (R)-3-(S)-(5-oxo-2-pyrrolidinyl)carbonyl]-tetrahydrothiazole-4-carboxylic acid. It has the advantages of rapid distribution and excretion, no accumulation in the body, and good tolerance. It can not only promote non-specific immune responses, but also promote specific immune responses. At present, it has been listed in many countries in Asia, Europe, America, etc., and is mainly used to treat bacteria (pneumococcus, Escherichia coli, Pseudomonas aeruginosa, Proteus, etc.) and viruses (influenza virus) by promoting the body's immune f...

Claims

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Application Information

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IPC IPC(8): C07K5/078
Inventor 林扬姚德勇郝智慧贾德强王艳玲
Owner QINGDAO VLAND BIOTECH INC
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