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Method for preparing Setmelanotide

A technology of resin and amino resin, which is applied in the field of preparation of polypeptide drugs, can solve the problems of complex and cumbersome methods, inconvenient large-scale production, etc., and achieve the effect of simple process operation, high product yield, and simple preparation process operation

Pending Publication Date: 2020-09-29
CHENGDU SHENGNUO BIOPHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are few reports on the preparation method of Setmelanotide. Chinese patent CN201080051643 reports the liquid phase fragment condensation method. This method is complicated and cumbersome, and it is not convenient for large-scale production. The present invention provides a high-efficiency preparation method of Setmelanotide to meet the medical needs

Method used

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  • Method for preparing Setmelanotide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] The synthesis of embodiment 1 Setmelanotide peptide resin

[0029] Setmelanotide peptide resins are:

[0030] Ac-Arg(Pbf)-Cys(Trt)-D-Ala-His(Trt)-D-Phe-Arg(Pbf)-Trp(Boc)-Cys(Trt)-aminoresin

[0031] Using Rink Amide-MBHA resin as the starting resin, the Setmelanotide peptide resin was prepared by de-Fmoc protection and coupling reaction, followed by coupling with the protected amino acids shown in the table below.

[0032] The protected amino acids corresponding to the protected amino acids used in this example are shown in the table below:

[0033] The peptide sequence n= Protected Amino Acids 1 Fmoc-Cys(Trt) 2 Fmoc-Trp(Boc) 3 Fmoc-Arg(Pbf) 4 Fmoc-D-Phe 5 Fmoc-His(Trt) 6 Fmoc-D-Ala 7 Fmoc-Cys(Trt) 8 Fmoc-Arg(Pbf) 9 Ac 2 o

[0034] 1. Insert the first protected amino acid

[0035] Take 0.03 mol of the first protected amino acid and 0.03 mol of HOBt, and dissolve it with an appropriate amount of ...

Embodiment 2

[0040] The synthesis of embodiment 2 Setmelanotide peptide resin

[0041] Setmelanotide peptide resins are:

[0042] Ac-Arg(Pbf)-Cys(Trt)-D-Ala-His(Trt)-D-Phe-Arg(Pbf)-Trp-Cys(Trt)-amino resin

[0043] The preparation method of the peptide resin is the same as in Example 1.

[0044] The protected amino acids corresponding to the protected amino acids used in this example are shown in the table below:

[0045] The peptide sequence n= Protected Amino Acids 1 Fmoc-Cys(Trt) 2 Fmoc-Trp 3 Fmoc-Arg(Pbf) 4 Fmoc-D-Phe 5 Fmoc-His(Trt) 6 Fmoc-D-Ala 7 Fmoc-Cys(Trt) 8 Fmoc-Arg(Pbf) 9 Ac 2 o

Embodiment 3

[0046] The synthesis of embodiment 3 Setmelanotide peptide resin

[0047] Setmelanotide peptide resins are:

[0048] Ac-Arg(Pbf)-Cys(Acm)-D-Ala-His(Trt)-D-Phe-Arg(Pbf)-Trp-Cys(Acm)-amino resin

[0049] The preparation method of the peptide resin is the same as in Example 1.

[0050] The protected amino acids corresponding to the protected amino acids used in this example are shown in the table below:

[0051] The peptide sequence n= Protected Amino Acids 1 Fmoc-Cys(Acm) 2 Fmoc-Trp 3 Fmoc-Arg(Pbf) 4 Fmoc-D-Phe 5 Fmoc-His(Trt) 6 Fmoc-D-Ala 7 Fmoc-Cys(Acm) 8 Fmoc-Arg(Pbf) 9 Ac 2 o

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Abstract

The invention provides a method for preparing Setmelanotide. According to the method, amino resins are used as starting resins, corresponding protecting amino acids are sequentially inoculated according to the reverse direction of the amino sequence of the Setmelanotide, so that Setmelanotide peptide resins are obtained; the Setmelanotide protecting peptide resins are subjected to acidolysis and oxidative cyclization to obtain Setmelanotide crude products; and the Setmelanotide crude products are subjected to purification and freeze drying to obtain Setmelanotide pure products. The technologyis simple to operate, and the products are high in total yield, and suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of polypeptide drug preparation methods, in particular to a preparation method of Setmelanotide. Background technique [0002] Setmelanotide, an oligopeptide melanocortin-4 receptor (MC4R) agonist, found that once daily subcutaneous injection of setmelanotide reduced overeating and body weight in three LEPR-deficient obese patients. Setmelanotide was well tolerated, with no serious adverse events reported. [0003] Setmelanotide has the following structure: [0004] Ac-Arg-c(Cys-D-Ala-His-D-Phe-Arg-Trp-Cys)-NH2 [0005] There are few reports on the preparation method of Setmelanotide. Chinese patent CN201080051643 reports the liquid phase fragment condensation method. This method is complicated and cumbersome, and is not convenient for large-scale production. The present invention provides a high-efficiency preparation method of Setmelanotide to meet the medical use. Contents of the invention [0006] T...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/685C07K1/06C07K1/04C07K1/20
CPCC07K14/685Y02P20/55
Inventor 董华建郭德文文永均
Owner CHENGDU SHENGNUO BIOPHARM
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