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Preparation method of Tirzepatide

A fmoc-tyr-ser, boc-tyr technology, applied in the field of peptide drug preparation, can solve the problems of unfavorable industrial production, low purity and yield, high cost, etc. Effect of material cost and purification cost

Active Publication Date: 2021-04-02
SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to solve the existing problems in the existing synthesis process, such as many impurities, low purity and yield, high cost, cumbersome operation steps, excessive waste liquid, and unfavorable industrial production, and provides a new preparation of Tirzepatide method, the method improves the purity of the crude peptide, greatly reduces the material cost and purification cost, and facilitates industrialized scale-up production

Method used

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  • Preparation method of Tirzepatide
  • Preparation method of Tirzepatide
  • Preparation method of Tirzepatide

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1: the preparation method of Tirzepatide

[0021] Synthesis of Tirzepatide Peptide Resin

[0022] Tirzepatide Peptide Resin:

[0023] Boc-Tyr(tBu)-Aib-Glu(OtBu)-Gly-Thr(tBu)-Phe-Thr(tBu)-Ser(tBu)-Asp(OtBu)-Tyr(tBu)-Ser(tBu)-Ile- Aib-Leu-Asp(OtBu)-Lys(Boc)-Ile-Ala-Gln(Trt)-Lys(AEEA-AEEA-γGlu-Eicosanedioicacid(mon-tBu))-Ala-Phe-Val-Gln(Trt)- Trp(Boc)-Leu-Ile-Ala-Gly-Gly-Pro-Ser(tBu)-Ser(tBu)-Gly-Ala-Pro-Pro-Pro-Ser(tBu)-Aminoresin.

[0024] Using Rink Amide MBHA resin as the starting resin, the Tirzepatide peptide resin was prepared by de-Fmoc protection and coupling reaction, followed by coupling with the protected amino acids in Table 1, Table 2, and Table 3. The protected amino acids or fragments corresponding to the protected amino acids used in this example are as follows:

[0025] Table 1

[0026]

[0027]

[0028]

[0029] Table 2

[0030]

[0031]

[0032]

[0033] table 3

[0034]

[0035]

[0036]

[0037]1. Insert th...

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Abstract

The invention discloses a preparation method of Tirzepatide, and belongs to the technical field of peptide synthesis. According to the method, amino resin is adopted as starting resin, a solid-phase polypeptide synthesis method is adopted for preparation, Tirzepatide peptide resin is obtained by a polypeptide solid-phase synthesis method, then Tirzepatide resin is subjected to acidolysis to obtaina Tirzepatide crude product, and finally, the Tirzepatide crude product is purified to obtain a Tirzepatide pure product. According to the method disclosed by the invention, special protective aminoacids, namely Boc-Tyr (tBu)-Aib-OH and Fmoc-Lys (AEEA-AEEA-gamma Glu (alpha-OtBu)-Eicosanedioicacid (mon-tBu))-OH, Fmoc-Tyr-Ser (pro-me-me)-OH and Fmoc-(Dmb)Gly-OH, are adopted. According to the method, the purity of the crude peptide is improved, the material cost and the purification cost are greatly reduced, and industrial large-scale production is facilitated.

Description

technical field [0001] The invention belongs to the technical field of polypeptide drug preparation methods, in particular to a preparation method of Tirzepatide. Background technique [0002] Tirzepatide is a GIP and GLP-1 dual agonist. The structure of Tirzepatide is as follows: Tyr-Aib-Glu-Gly-Thr 5 -Phe-Thr-Ser-Asp-Tyr 10 -Ser-Ile-Aib-Leu-Asp 15 -Lys-Ile-Ala-Gln-Lys 20 (Eicosanedioic acid-γ-Glu-AEEA-AEEA)-Ala-Phe-Val-Gln-Trp 25 -Leu-Ile-Ala-Gly-Gly 30 -Pro-Ser-Ser-Gly-Ala 35 -Pro-Pro-Pro-Ser 39 -NH 2 . [0003] Tirzepatide demonstrated its efficacy by improving β-cell function and increasing insulin sensitivity; Tirzepatide showed both efficacy and tolerability improvement in patients with lower initial doses and smaller subsequent dose escalations; treatment with Tirzepatide8 A week later, Japanese patients with type 2 diabetes showed significant reductions in A1C and body weight; Tirzepatide improved markers of nonalcoholic steatohepatitis (NASH, liver inflamm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/00C07K1/06C07K1/04
CPCC07K14/001Y02P20/55
Inventor 陈烨袁凤奎
Owner SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD
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