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Impurities obtained by preparation of pidotimod and quality detection method thereof

A quality detection method, Pidotimod's technology, applied in measuring devices, material separation, instruments, etc., can solve problems such as impurities, and achieve accurate and efficient results

Inactive Publication Date: 2018-06-22
CHANGZHOU YINSHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When pidotimod is synthesized by the above-mentioned process method, some impurities will inevitably be produced

Method used

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  • Impurities obtained by preparation of pidotimod and quality detection method thereof
  • Impurities obtained by preparation of pidotimod and quality detection method thereof
  • Impurities obtained by preparation of pidotimod and quality detection method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In the quality detection method for preparing pidotimod in this embodiment, L-thioproline ethyl ester hydrochloride (500g, 2.53mol) and dichloromethane 1500g suspension were cooled to 0-5°C, and added dropwise Concentration is 20% sodium hydroxide solution (531.16g, 2.66mol), continue to stir for 5min after dropwise addition, separate the phases, add L-pyroglutamic acid (326.56g, 2.53mol) in the organic phase, cool to 0~5 ℃, dropwise add a mixed solution of dicyclohexylcarbodiimide (521.88g, 2.53mol) and dichloromethane 1000g, keep the temperature at 0-10℃ during the dropwise addition, stir for 0.5-1h after dropping, filter, and use 500g The filter cake was rinsed with dichloromethane, and the dichloromethane solution containing pidotimod ethyl ester was cooled to 0-5°C, and a 7.5% sodium hydroxide solution (1281.53g, 2.41mol) was added dropwise. Always keep the internal temperature at 0-5°C, after the dropwise addition, the pH value is 9-10, keep stirring at the intern...

Embodiment 2

[0037] The quality detection method for the preparation of pidotimod in this embodiment, the rest is the same as in Example 1, except that dicyclohexylcarbodiimide uses N, N'-diisopropylcarbodiimide in equimolar amounts Imine instead, sodium dihydrogen phosphate phosphoric acid solution and methanol at a pH of 2.5, where the volume ratio of methanol to phosphoric acid is 60:40. The reaction product was detected by high performance liquid chromatography, the peak area of ​​compound A was 0.0793%, and the peak area of ​​compound B was 0.0862%, which met the requirements.

Embodiment 3

[0039] The quality detection method of the preparation pidotimod of the present embodiment, all the other parts are the same as embodiment 1, the difference is: dicyclohexylcarbodiimide adopts 1-(3-dimethylaminopropyl) in an equimolar amount -3-Ethylcarbodiimide hydrochloride instead, sodium dihydrogen phosphate phosphoric acid solution and methanol have a pH of 3.5, where the volume ratio of methanol to phosphoric acid is 80:20. The reaction product was detected by high performance liquid chromatography, the peak area of ​​compound A was 0.0882%, and the peak area of ​​compound B was 0.0906%, which met the requirements.

[0040] The reagents used in the present invention are all purchased products unless otherwise specified, and the concentrations are all chemically pure.

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Abstract

The invention relates to a quality detection method for preparation of pidotimod. A pidotimod-containing reaction product is prepared by performing ionization, condensation and hydrolysis reaction insequence on L-sulfur-proline ethyl ester hydrochloride and L-pyroglutamic acid which are used as reactants. The quality detection method is characterized in that high-performance liquid chromatography-based measurement for the reaction product shows that a peak area of a compound A included in the reaction product is no more than 0.1 percent, and a peak area of a compound B included in the reaction product is no more than 0.1 percent. The compound A is of a structure as shown in Formula V, and the compound B is of a structure as shown in Formula VI. The quality detection method for preparationof the pidotimod is favorable for controlling the drug quality in a production process.

Description

technical field [0001] The invention provides an impurity produced during the preparation of pidotimod and a method for using the impurity in mass analysis, belonging to the technical field of chemical synthesis. Background technique [0002] Pidotimod was developed by the Italian company Poli industria chimca S.P.A in the 1980s. It was approved for clinical use in 1993. It is a synthetic immune booster. Its structure is similar to dipeptide. Its chemical name is For (R)-3-(S)-[(5-oxo-2-pyrrolidinyl)carbonyl]-tetrahydro-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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/02G01N30/06C07K5/072C07D513/04
CPCG01N30/02C07D513/04C07K5/06104G01N30/06G01N2030/067
Inventor 韩加齐刘会丽王娟娟孙园园沙成扬
Owner CHANGZHOU YINSHENG PHARMA
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