Synthetic method for semaglutide

A synthesis method and technology of semaglutide are applied in the field of synthesis of semaglutide, which can solve the problems of low synthesis yield of semaglutide, difficult product purification and high production cost, so as to reduce the research scope of impurities and facilitate purification. , Easy to enlarge the effect of production

Active Publication Date: 2019-03-12
CHENGDU SINTANOVO BIOTECHNOLOGV CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the technical problems of low synthetic yield of semaglutide, high production cost and difficult product purification, the pres

Method used

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  • Synthetic method for semaglutide
  • Synthetic method for semaglutide
  • Synthetic method for semaglutide

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Experimental program
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Effect test

Embodiment 1

[0061] Such as figure 1 Shown, a kind of synthetic method of semaglutide of the present invention comprises the following steps:

[0062] 1. Synthesis of the first peptide fragment sequence to the sixth peptide fragment sequence

[0063] 1.1 Preparation of Boc-His(Trt)-Aib–OH in liquid phase:

[0064] Boc-His(Trt)-OH (5.01g, 10.07mmol) with side chain protection, HOBT (2.72g, 20.14mmol), DIEA (3.90g, 30.21mmol), methyl 2-aminoisobutyrate hydrochloride (1.55g, 10.07mmol) was dissolved in 100ml of DMF, HATU (6.54g, 17.20mmol) was added, stirred at room temperature for 4 hours, the reaction solution was poured into ice water, and a white solid was precipitated, filtered to obtain a white solid, and then washed with saturated saline Beating and washing three times, finally beating and washing once with clear water, put into a vacuum drying oven to dry to obtain 5.98g, filter and concentrate to dryness, the product obtained is dissolved in THF (50ml), water (30ml) is added, and l...

Embodiment 2

[0089] A synthetic method for semaglutide, comprising the following steps:

[0090] (1) Synthesis of 6 side chain protected peptide fragment sequences;

[0091] (2) Stepwise coupling of each peptide fragment sequence in a solid phase to obtain a fully protected semaglutide linear polypeptide.

[0092] Wherein, in the step (1), the sequences of the peptide fragments protected by the 6 side chains are specifically as follows:

[0093] The first peptide fragment sequence is the 7th-10th amino acid in the semaglutide sequence,

[0094] The second peptide fragment sequence is the 11th-15th amino acid in the semaglutide sequence,

[0095] The third peptide fragment sequence is the 16th-22nd amino acid in the semaglutide sequence,

[0096] The fourth peptide fragment sequence is the 23rd-28th amino acid in the semaglutide sequence,

[0097] The fifth peptide fragment sequence is the 29th-32nd amino acid in the semaglutide sequence,

[0098] The sixth peptide fragment sequence is...

Embodiment 3

[0127] A synthetic method for semaglutide, comprising the following steps:

[0128] (1) Synthesis of 6 side chain protected peptide fragment sequences;

[0129] (2) Stepwise coupling of each peptide fragment sequence in a solid phase to obtain a fully protected semaglutide linear polypeptide.

[0130] Wherein, in the step (1), the sequences of the peptide fragments protected by the 6 side chains are specifically as follows:

[0131] The first peptide fragment sequence is the 7th-11th amino acid in the semaglutide sequence,

[0132] The second peptide fragment sequence is the 12th-17th amino acid in the semaglutide sequence,

[0133] The third peptide fragment sequence is the 18th-21st amino acid in the semaglutide sequence,

[0134] The fourth peptide fragment sequence is the 22nd-26th amino acid in the semaglutide sequence,

[0135] The fifth peptide fragment sequence is the 27th-31st amino acid in the semaglutide sequence,

[0136] The sixth peptide fragment sequence is...

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Abstract

The invention discloses a synthetic method for semaglutide. The synthetic method for the semaglutide comprises the following steps of (1) synthesizing peptide segment sequences protected by 6 side chains; and (2) gradually coupling various peptide segment sequences in a solid phase to obtain a fully protected semaglutide straight-chain polypeptide. The semaglutide synthesized by utilizing the method is high in purity and yield and low in synthesis cost.

Description

technical field [0001] The invention relates to the field of pharmacy, in particular to a method for synthesizing semaglutide. Background technique [0002] Semaglutide, English name Semaglutide, is a glucagon-like peptide-1 (GLP-1) analogue, the sequence is H-His-Aib-Glu-Gly-Thr-Phe-Thr-Ser-Asp- Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Lys(AEEA-AEEA-r-Glu-Otc)-Glu-Phe-Ile-Ala-Trp-Leu-Val-Arg-Gly -Arg-Gly-OH, molecular formula: C187H291N45O59, as a long-acting GLP-1 receptor agonist, only needs to be injected once a week, and can be used to assist diet control and exercise to improve blood sugar control in patients with type 2 diabetes, At the same time, it can reduce the patient's weight. [0003] At present, the synthetic methods of semaglutide are as patented: CN106928343A, CN101133082A, CN106478806A adopt Fmoc strategy solid phase stepwise coupling to synthesize semaglutide. The amino acid stepwise coupling synthesis cycle of this method is long, the reaction is incomp...

Claims

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Application Information

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IPC IPC(8): C07K14/605C07K1/20C07K1/06C07K1/04C07K1/02
CPCC07K14/605Y02P20/55
Inventor 高剑李元波钟国庆徐彬左成孙玲唐智勇张佳丽
Owner CHENGDU SINTANOVO BIOTECHNOLOGV CO LTD
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