Impurities obtained from the preparation of pidotimod ethyl ester and its quality detection method

A quality detection method, the technology of Domodex ethyl ester, applied in the direction of measuring devices, instruments, scientific instruments, etc., can solve the problems such as impurities, and achieve accurate and efficient results

Active Publication Date: 2020-05-22
CHANGZHOU YINSHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 from the preparation of pidotimod ethyl ester and its quality detection method
  • Impurities obtained from the preparation of pidotimod ethyl ester and its quality detection method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In the quality detection method for the preparation of pidotimod ethyl ester in this embodiment, L-thioproline ethyl ester hydrochloride (500g, 2.53mol) and 1500g of dichloromethane were added to a 3L reaction flask, cooled to 0~ 5°C, dropwise add 20% sodium hydroxide solution (531.16g, 2.66mol), keep the internal temperature at 0-10°C during the dropwise addition, after the dropwise addition, the pH value is 8-9, continue to stir for 5min, and separate the phases , wash the organic phase with 500g of saturated sodium chloride, then add 500g of anhydrous sodium sulfate to the organic phase to dry for 1-2 h, filter, wash the filter cake with 500g of dichloromethane, and pour the filtrate into another 5L reaction flask , add L-pyroglutamic acid (326.56g, 2.53mol), stir for 30min, cool to 0-5°C, add dropwise a mixed solution of dicyclohexylcarbodiimide (521.88g, 2.53mol) and dichloromethane 1000g , keep the temperature at 0-10°C during the dropwise addition, return to 15-2...

Embodiment 2

[0039] The quality detection method of the preparation pidotimod ethyl ester of the present embodiment, the rest is the same as embodiment 1, the difference is: dicyclohexylcarbodiimide adopts the N of equimolar amount, N'-diisopropyl Instead of carbodiimide, the pH value of sodium dihydrogen phosphate phosphoric acid solution and methanol is 2.5, wherein the volume ratio of methanol to sodium dihydrogen phosphate phosphoric acid solution is 60:40. The reaction product was detected by high performance liquid chromatography. The peak area of ​​compound A was 5.1123%, and the peak area of ​​compound B was 1.8637%, which met the requirements.

Embodiment 3

[0041] The quality detection method of the preparation pidotimod ethyl ester of the present embodiment, all the other parts are identical with embodiment 1, difference is: dicyclohexylcarbodiimide adopts the 1-(3-dimethylaminopropane of equimolar amount) Base)-3-ethylcarbodiimide hydrochloride instead, the pH value of sodium dihydrogen phosphate phosphoric acid solution and methanol is 3.5, wherein the volume ratio of methanol to sodium dihydrogen phosphate phosphoric acid solution is 80:20. The reaction product was detected by high performance liquid chromatography. The peak area of ​​compound A was 5.9822%, and the peak area of ​​compound B was 1.5061%, which met the requirements.

[0042]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 preparing pidotimod ethyl ester. The quality detection method for preparing pidotimod ethyl ester comprises the following steps: taking L-thioproline ethyl ester hydrochloride and L-pyroglutamic acid as reactants, performing free and condensation reactions successively to obtain a reaction product containing pidotimod ethyl ester, wherein thepeak area of a compound A contained in the reaction product measured by the high performance liquid chromatography is not more than 6.5% and the peak area of a compound B contained in the reaction product measured by the high performance liquid chromatography is not more than 2.0%; the compound A has the structure as shown in the formula V, and the compound B has the structure as shown in the formula VI. The quality detection method for preparing pidotimod ethyl ester disclosed by the invention is favorable for controlling the drug quality during the production process.

Description

technical field [0001] The invention provides an impurity produced during the preparation of pidotimod ethyl ester and a method for using the impurity in mass analysis, belonging to the technical field of chemical synthesis. Background technique [0002] Pidotimod (Pidotimod) was developed by the Italian company Poli industria chimca S.P.A in the 1980s and was approved for clinical use in 1993. It is a synthetic immune booster, its structure is similar to dipeptide, and 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 such as Asia, Europe, and the Americas, and is mainly used to treat bacteria (pneumococcus, Escherichia coli, Pseudomonas aeruginosa, Proteus, etc.) and viruse...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N30/06G01N30/74
CPCG01N30/06G01N30/74
Inventor 游新雨潘利俊蒋燕华焦丹丹蒋吕菊
Owner CHANGZHOU YINSHENG PHARMA
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