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Synthesis and preparation process of eptifibatide

A preparation process and fibatide technology are applied in the field of eptifibatide synthesis and preparation technology, which can solve the problems of waste of hexapeptide raw materials, pressure of large-scale production costs, low yield and the like, and achieve higher yield and lower cost. reduced effect

Inactive Publication Date: 2010-06-23
SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] A large amount of expensive peptide resins are required in solid-phase synthesis, which puts cost pressure on large-scale production of enterprises
However, in the liquid phase method mentioned in the world patent WO2005100381, the yield in the final cyclization and coupling steps is not high, resulting in a serious waste of hexapeptide raw materials that do not participate in the reaction

Method used

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  • Synthesis and preparation process of eptifibatide
  • Synthesis and preparation process of eptifibatide
  • Synthesis and preparation process of eptifibatide

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0079] 1. Mpr(X)-Har(R) with side chain protection 4 )-Gly-Asp(R 2 )-Trp(R 3 )-Pro-Cys(Y)-NH 2 Synthesis of Linear Peptides

[0080] Route 1:

[0081] 1. Boc-Pro-Cys(acm)-NH 2 Synthesis

[0082] In a 50 ml round bottom flask was added Boc-Pro-OH (1.076g), NH 2 -Cys(acm)-NH 2 (0.960g), HOSU (N-hydroxysuccinimide) (0.575g), dissolved with 40ml of anhydrous DMF, after adding DCC (1.030g) under ice-water bath, stirred at room temperature for 2 hours, and detected that the reaction was complete. The precipitate produced by the reaction was removed by suction filtration, concentrated under reduced pressure to remove DMF, and then dissolved with a large amount of ethyl acetate, followed by 10% NaHCO 3 , 15% dilute hydrochloric acid, and saturated brine, dried over anhydrous sodium sulfate, and spin-dried ethyl acetate to obtain 1.760 g of solid. HPLC purity: greater than 92%, yield 90.5% MS=389 (M+1).

[0083] 2. Boc-Trp-Pro-Cys(acm)-NH 2 Synthesis

[0084] Weigh Boc-Pro-...

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Abstract

The invention provides synthesis and preparation process of eptifibatide, which includes the following steps: (1) liquid-phase synthesis of peptide segment 1: Mpr(x)-Har(R4)-Gly-OH; (2) liquid-phase synthesis of peptide segment 2: R1-Asp(R2)-Trp(R3)-Pro-Cys(Y)-NH2; (3) condensation of the peptide segment 1 and the peptide segment 2 to prepare fully protected peptide segment 3: Mpr(X)-Har(R4)-Gly-Asp(R2)-Trp(R3)-Pro-Cys(Y)-NH2; (4) deprotection of the peptide segment 3 to get linear peptide: Mpr(X)-Har-Gly-Asp-Trp-Pro-Cys(Y)-NH2; and (5) oxidation of the linear peptide to synthetize disulfide bridges to produce cyclic peptide. Through the method of firstly synthesizing linear peptide and then cyclizing the linear peptide, the invention substantially improves the yield, the product is obtained finally through purification, the cost is reduced, and the synthesis and preparation process is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a synthesis and preparation process of eptifibatide, which belongs to the field of biotechnology. (2) Background technology [0002] Coronary heart disease is the number one cause of death in western developed countries, and millions of people get sick every year. Although the incidence rate in my country is not as good as that of western developed countries, there are about 1 to 2 million people every year, and there is a rising trend. Although modern technology can Plastic surgery or bypass surgery is used for treatment, but the chance of getting sick again after surgery is relatively high, and drug treatment is also required. Eptifibatide is a highly efficient platelet polypeptide antagonist. This drug should be able to directly block the binding of platelet glycoprotein receptors and ligands, so that the heart can be supplied with blood, and the symptoms of coronary heart disease can be alleviated or eliminated. [0003...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/06C07K1/02
CPCC07K7/06C07K5/1021C07K5/0823Y02P20/55
Inventor 路杨徐峰杨东晖穆斌
Owner SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD
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