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glp-1 agonistic polypeptide compound and its salt, synthesis method and application

A GLP-1, 1. GLP-1 technology, applied in the preparation method of peptides, chemical instruments and methods, peptide/protein components, etc., can solve the problems of inability to achieve blood sugar control and weight loss, singleness, limitation, etc.

Active Publication Date: 2021-03-09
HANGZHOU ALLSINO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently commercially available incretin analogs or dipeptidyl peptidase IV (DPP-4) inhibitors only utilize a single mechanism of action for glycemic control; Peptide compound with excellent sugar activity and weight loss effect
[0004] Dosage of GLP-1 analogues has been found to be limited by side effects such as nausea and vomiting, and thus dosing often does not achieve full efficacy in glycemic control and weight loss. Natural GLP-1 is all consumed by ubiquitous proteolytic enzymes, especially Dipeptidyl peptidase-4 (DPP-4) rapidly inactivates and, therefore, should only be used for short-term metabolic control

Method used

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  • glp-1 agonistic polypeptide compound and its salt, synthesis method and application
  • glp-1 agonistic polypeptide compound and its salt, synthesis method and application
  • glp-1 agonistic polypeptide compound and its salt, synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] Embodiment 1, the synthesis of SEQ ID NO: 1 polypeptide compound:

[0125] HX 2 EGTFTSDVSSYLEX 2 QAAK(HOOC-(CH 2 ) 16 -CO-γ-Glu-AEEA-AEEA)EFIAWLVRGRG

[0126] 1. Synthesis of the peptide chain of the polypeptide compound of SEQ ID NO: 1

[0127] 1.1 Resin swelling

[0128] Weigh 10g of Wang-Resin (degree of substitution 0.53mmol / g), swell with 100mL of DCM for 30min, filter to remove DCM, then swell with 100mL of DMF for 30min, rinse with DMF and 100mL of DCM respectively.

[0129] 1.2 Synthesis of Fmoc-Gly-Wang-Resin

[0130] Dissolve Fmoc-Gly(tBu)-OH (15mmol), HOBT (18mmol) and DIC (18mmol) in 100mL of DMF, then add this solution to the resin obtained in the previous step to react for 2 hours, and filter the reaction solution after completion. The resin was washed 3 times with 100 mL each of DCM and DMF.

[0131] 1.3 Removal of Fmoc protecting group

[0132] Add 25% piperidine / DMF (V / V) solution containing 0.1M HOBt to the washed resin to remove Fmoc, and was...

Embodiment 2

[0141] Embodiment 2, the synthesis of SEQ ID NO:2 polypeptide compound:

[0142] HX 2 EGTFTSDVSSYLEX 1 QAAK(HOOC-(CH 2 ) 16 -CO-γ-Glu-AEEA-AEEA)EFIAWLVRGRG

[0143] The synthesis method was the same as in Example 1, and the purified sample solution was collected and freeze-dried to obtain 3.93 g of pure product.

Embodiment 3

[0144] Embodiment 3, the synthesis of SEQ ID NO:3 polypeptide compound:

[0145] HX 3 EGTFTSDVSSYLEX 3 QAAK(HOOC-(CH 2 ) 16 -CO-γ-Glu-AEEA-AEEA)EFIAWLVRGRG

[0146] The synthesis method was the same as in Example 1, and the purified sample solution was collected and freeze-dried to obtain 2.87 g of pure product.

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Abstract

The invention discloses a series of GLP-1 agonistic polypeptide compounds, belonging to the technical field of polypeptide medicinal chemistry; aiming at the in vivo stability, hypoglycemic and weight loss effects and side effects of existing compounds, a series of compounds utilizing dual action mechanisms with better GLP-1 agonist polypeptide compound with excellent hypoglycemic activity and weight loss effect. The amino acid sequence of this GLP-1 agonist polypeptide compound is: H Xaa 1 EGTFTSDVSSYLE Xaa 2 QAA Xaa 3 EFIAWLVRGRG, and the C-terminal amino acid of this type of polypeptide compound is a carboxyl group or a carboxyl group is amidated as the C-terminal. The invention also discloses the preparation method, pharmaceutically acceptable salt, pharmaceutical composition and medicament of the polypeptide compound. The polypeptide compound of the present invention has both hypoglycemic and weight loss effects, and can be used as an effective raw material for preparing a drug for treating or preventing diabetes or a slimming drug.

Description

technical field [0001] The invention relates to the field of polypeptide compounds, in particular to a series of polypeptide compounds with double incretin peptide analogues, which can stimulate the receptor of human glucagon-like peptide-1 (GLP-1), and can be used to treat type 2 diabetes. The present invention also relates to the pharmaceutically acceptable salt of the polypeptide compound, the polypeptide pharmaceutical composition, medicament, preparation method and application thereof. Background technique [0002] The cause of metabolic syndrome is abnormal metabolism of various substances such as protein, fat and carbohydrates. Overnutrition and reduced physical activity can lead to obesity and obesity-related diseases such as diabetes. In recent years, the incidence of type 2 diabetes and abnormal blood lipid metabolism has been increasing; type 2 diabetes is the most common form of diabetes, accounting for about 90% of all diabetes. Type 2 diabetes is characterize...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07K14/00C07K1/08C07K1/06C07K1/04A61K38/16A61P3/10A61P3/04
CPCC07K14/001A61P3/10A61P3/04A61K38/00C07K14/605
Inventor 赵呈青施国强李顺子王蔡典
Owner HANGZHOU ALLSINO CHEM
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