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Preparation method of GLP-1 analogue fragment activated ester

A technology of GLP-1 and analogues, which is applied in the field of peptide pharmaceuticals, can solve the problems of unfavorable industrial scale-up production in the preparation of activated esters of GLP-1 analogue fragments, and achieve the effect of shortening the preparation time and avoiding decomposition

Pending Publication Date: 2022-02-22
SICHUAN KELUN PHARMA RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the problem that the preparation of activated esters of GLP-1 analog fragments is not conducive to industrial scale-up production, the present invention provides a method for preparing activated esters of GLP-1 analog fragments

Method used

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  • Preparation method of GLP-1 analogue fragment activated ester
  • Preparation method of GLP-1 analogue fragment activated ester
  • Preparation method of GLP-1 analogue fragment activated ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OSu

[0032]

[0033] Weigh 82.5g Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OH and 2.4g DMAP, add 25.6gDSC, then add 500mL DMF, stir and dissolve, control the reaction temperature 0-5℃, add 19.83ml of DIEA was reacted at 0-10°C for 0.5-1h to obtain Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OSu with a detection conversion rate of 84%.

Embodiment 2

[0034] Example 2: Synthesis of Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OSu

[0035] Weigh 82g of Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OH and 2.4g of DMAP, add 25g of DSC, then add 500ml of DMF, after stirring and dissolving, the reaction system is controlled by an ice-water bath at a temperature of 0 -5℃, add 16.73mlEt 3 N, control the reaction at 0-10° C. for 0.5-1 h to obtain Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OSu, and the detected conversion rate is 82%.

Embodiment 3

[0036] Example 3: Synthesis of Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OSu

[0037] Weigh 82.5g Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OH and 2.4g DMAP, add 25.6gDSC, then add 500ml DMF, after stirring and dissolving, the reaction system is controlled by an ice-water bath. -5°C, add 13.19ml NMM, control the reaction at 0-10°C for 0.5-1h, and obtain Boc-His(Trt)-Aib-Glu(O-tBu)-Gly-OSu, the detected conversion rate is 83%.

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Abstract

The invention provides a preparation method of GLP-1 analogue fragment activated ester. The preparation method comprises the following step: reacting a polypeptide fragment of a GLP-1 analogue with a condensing agent in a system of an organic solvent and alkali. According to the method disclosed by the invention, the activated ester is prepared by adopting a proper condensing agent and raw materials which are easy to commercially produce, so that the preparation time of the activated ester is effectively shortened, the product can be used for synthesizing the GLP-1 analogue without post-treatment, and the decomposition of the activated ester in the post-treatment process is avoided; the method is suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the field of polypeptide pharmacy, and in particular relates to a preparation method of GLP-1 analog fragment activated ester. Background technique [0002] GLP-1 receptor agonists can lower blood sugar, weight loss, lower blood pressure, and lower lipids at the same time, protect the function of islet β cells, and have cardiovascular benefits. It is the new mechanism hypoglycemic drug with the highest recommendation in the US guidelines, US guidelines Recommended for first-line treatment, second only to metformin. [0003] CN101910193A introduces a semi-recombinant method for producing GLP-1 analogs and derivatives containing non-protein amino acid terminals at the N-terminal part by combining recombinant expression technology and chemical peptide synthesis. In the instruction manual, the method of making N-hydroxysuccinimide ester is introduced, using Boc-His(Boc)-Aib-Glu(OtBu)-Gly-OH, Fmoc-His(Boc)-Aib-Glu(OtBu)- Gly-OH, F...

Claims

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Application Information

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IPC IPC(8): C07K14/605C07K1/02
CPCC07K14/605C07K1/026
Inventor 戚建英杨燕苹刘晨康艳萍王晶翼
Owner SICHUAN KELUN PHARMA RES INST CO LTD
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