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US 2023/0406900 A1Published application
Process for preparing glucagon-like peptide-1
AssigneeScinoPharm Taiwan, Ltd.
InventorsMing-Chih Wu, Meng-Fen Ho, Tsung-Yu Hsiao
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Abstract
The present disclosure provides an improved process for the preparation of glucagon-like peptide-1 agonist peptide. Specifically, it relates to a manufacturing process useful for reducing impurities and increasing the yields and the balance of cost in the preparation of liraglutide or semaglutide.
Claims19
A process for the preparation of glucagon-like peptide-1 agonist peptide represented by formula (1),
- (1)
- H-His1-X2-Glu3-Gly4-Thr5-Phe6-Thr7-Ser8-Asp9-Val10-
- Ser11-Ser12-Tyr13-Leu14-Glu15-Gly16-Gln17-Ala18-Ala19-
- Lys20(R)-Glu21-Phe22-Ile23-Ala24-Trp25-Leu26-Val27-
- Arg28-Gly29-Arg30-Gly31-OH
- wherein:
- X is Ala or Aib;
- R is -γ-Glu-Hexadecanoic acid or -AEEA-AEEA-γ-Glu-Octadecanedioic acid;
- comprising steps of:
- (a) synthesizing a protected peptide on a solid phase by stepwise coupling of a protected amino acid and a protected dipeptide, the protected dipeptide comprising a pseudoproline dipeptide and a non-pseudoproline dipeptide;
- (b) cleaving the protected peptide from the solid phase, and deprotecting the protected peptide to obtain the peptide.
8 more elements
A glucagon-like peptide-1 agonist peptide represented by formula (1),
- (1)
- H-His1-X2-Glu3-Gly4-Thr5-Phe6-Thr7-Ser8-Asp9-Val10-
- Ser11-Ser12-Tyr13-Leu14-Glu15-Gly16-Gln17-Ala18-Ala19-
- Lys20(R)-Glu21-Phe22-Ile23-Ala24-Trp25-Leu26-Val27-
- Arg28-Gly29-Arg30-Gly31-OH
- wherein:
- X is Ala or Aib;
- R is -γ-Glu-Hexadecanoic acid or -AEEA-AEEA-γ-Glu-Octadecanedioic acid;
- and
- a content of deletion of X at position 2 of the glucagon-like peptide-1 agonist peptide is less than 0.10%.
7 more elements
Dependencies are inferred from the claim text.