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A kind of synthetic method of pidotimod

A synthetic method, the technology of pidotimod, which is applied in the field of pidotimod synthesis, can solve the problems of reducing racemization, no racemization, etc., and achieve the effects of solving the racemization problem, increasing the yield, and shortening the synthesis cycle

Active Publication Date: 2021-03-09
SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are still many other methods, but they are all based on the original reaction mechanism, or reduce racemization, or simply avoid other synthetic routes to achieve the purpose of obtaining authorized patents or publishing articles. Solve the problem of racemization to achieve the purpose of improving product quality and reducing costs

Method used

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  • A kind of synthetic method of pidotimod
  • A kind of synthetic method of pidotimod
  • A kind of synthetic method of pidotimod

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1, a Synthesis of President: This method employs a carboxy R group-protected L-thiazolidine-4-carboxylic acid ester or L-thiazolin-4-carboxylic acid and nitrogen R1 protection Glutamic acid is a catalyst in which R2 substituted with boric acid, the condensation forms the target compound shown by the formula III:

[0031]

[0032] The R is selected from: H, OTBU, BN, CHX, MPE, 2-pH1Pr, TEGBN, DAMB, Al, PNB, PTMSE or DMNB;

[0033] The R1 is selected from: , IVDDE, FMOC *, MTT or Alloc;

[0034] The R2 is selected from the group consisting of each benzene ring, a substituted benzene ring, furan, thiophene, imidazole or diazole.

Embodiment 2

[0035] Example 2, a Synthesis of a President described in Example 1: The substituted benzene ring is selected from the group consisting of 3-bit fluoride substitution, 3,5-spin substitution, 3 chlorine substitution or trifluoromethyl substitution Benzene ring.

[0036] The specific steps are as follows:

[0037] (1) A nitrogen R1-protected cokeline, R2 substituted boric acid, activated molecular sieve, organic solvent together, uniform uniform; activated molecular sieve with a molecular sieve of a diameter of 4 å; the organic solvent is anhydrous chloride Ethyl methane or ethyl acetate;

[0038] (2) Add a carboxyl R group-protected L-thiazolidine-4-carboxylic acid ester or L-thiazolidine-4-carboxylic acid, continuing the stirring reaction;

[0039] (3) After the reaction is completed, the reaction liquid is filtered by filtrate;

[0040](4) When the raw material uses a carboxyl R group-protected L-thiazolidine-4-carboxylate, nitrogen-free protective pangular amine, the filtrate is...

Embodiment 3

[0048] Embodiment 3, in the synthesis method of a President described in Example 1:

[0049] Raw nitrogen R1 protected cokeline, carboxy R group protected L-thiazolin-4-carboxylic acid ester or L-thiazolidine-4-carboxylic acid, R2 substituted boric acid molar ratio is 1.5: 1: 0.3 ;

[0050] Organic Solvent Volume ML and Nitrogen R1ONBS, DNBS, Troc, DTS, PNZ, ONZ, NVOC, NPPOC, HFA, DDZ, BPOC, NPS, NSC, BSMOC, α-NSMOC, IVDE, FMOC *, MTT or Alloc;

[0051] The R2 is selected from the group consisting of each benzene ring, a substituted benzene ring, furan, thiophene, imidazole or diazole.

[0052] Example 2, a Synthesis of a President described in Example 1: The substituted benzene ring is selected from the group consisting of 3-bit fluoride substitution, 3,5-spin substitution, 3 chlorine substitution or trifluoromethyl substitution Benzene ring.

[0053] The specific steps are as follows:

[0054] (1) A nitrogen R1-protected cokeline, R2 substituted boric acid, activated molecular s...

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Abstract

The invention is a synthetic method of pidotimod. It belongs to pure liquid phase synthesis; this method uses carboxyl R group protected L-thiazolidine-4-carboxylate or L-thiazolidine-4-carboxylic acid and nitrogen R1 protected pyroglutamic acid in R2 substituted boronic acid Under the catalyst, condensation forms the target compound pidotimod shown in the general formula III. High-purity products can also be obtained by recrystallization. The invention also discloses the use of the R2 substituted boronic acid in the synthesis of pidotimod. The method of the present invention greatly shortens the synthesis period, avoids the mechanism of oxazolidinone formed by all traditional synthesis methods of polypeptides, completely solves the problem of racemization, and the catalyst can be reused, thereby greatly reducing costs, high yield, good product purity, suitable for in industrial production.

Description

Technical field [0001] The present invention relates to a synthesis method of a plural, belonging to the field of chemical synthesis. Background technique [0002] Pidotimod is chemically called (4R) -3 - [[(2S) -5-oxo-2-pyrrolidinyl] carbonyl] -4-thiazolidine acid, is a new chemical synthetic immunity Accelerator, with antivision, antioxidant, anti-irritability, anti-infectivity, etc. The original research company is the Italian POLI Chemical Industry Company, and in 1993, it was used as an oral preparation, which was mainly used to prevent respiratory infections (RRI), chronic bronchitis, etc., which were used to prevent children, and made satisfactory results, so the compound It has a very important role in pharmaceutical. [0003] There are many synthetic methods of the compound, but some have high cost, inconvenience operation, poor stability; some methods are strict, not easy to operate, low total yield; although simple, yield Higher, but the reaction process needs to be tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K5/078
CPCC07K5/06173Y02P20/55
Inventor 徐峰谷海涛孙美禄李杰陈守菊
Owner SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD
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