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Method of preparing tetradecapeptide somatostatin

A technology of somatostatin and fourteen peptides, which is applied in the field of preparation of fourteen peptides somatostatin, can solve the problems of no discovery of the preparation method of fourteen peptides somatostatin, achieve simple and easy purification, complete peptide linking, and yield high rate effect

Inactive Publication Date: 2009-08-19
吴永平
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] But there is no bibliographical report on the preparation method that is specially used to improve the yield of fourteen peptide somatostatin

Method used

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  • Method of preparing tetradecapeptide somatostatin
  • Method of preparing tetradecapeptide somatostatin
  • Method of preparing tetradecapeptide somatostatin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of intermediate a: under the condition of using DMF, DCC and 3-(diethoxyphosphoryl)-1,2,3,-benzotriazin-4-one as the condensing agent, the reaction temperature is controlled at 25°C, and the reaction 5 hours. After the reaction is completed, add 20wt% liquid NaOH to carry out saponification reaction to obtain intermediate a.

[0050] Using DCC, ethyl acetate or benzyl chloroformate as a solvent, controlling the reaction temperature at 20°C, and reacting for 5 hours, after the reaction is completed, adding 20wt% liquid NaOH for saponification reaction to obtain intermediate b.

[0051] DMF, DCM or ethyl acetate was used as solvent, the reaction temperature was 15°C, and the reaction was carried out for 5 hours. The following two compounds were used for addition reaction to obtain intermediate c.

[0052] Fmoc-Cys-Ome Compound 1

[0053] Compound 2

[0054] Intermediate b and intermediate c use azidophosphoric acid diphenyl ester as a condensing agent...

Embodiment 2

[0057] Preparation of intermediate a: under the condition of using DMF, DCC and 3-(diethoxyphosphoryl)-1,2,3,-benzotriazin-4-one as the condensing agent, the reaction temperature is controlled at 25°C, and the reaction 2 hours. After the reaction is completed, add 20wt% liquid NaOH to carry out saponification reaction to obtain intermediate a.

[0058] Use DCC, ethyl acetate or benzyl chloroformate as solvent, control the reaction temperature at 20°C, and react for 2 hours. After the reaction is completed, add 20wt% liquid NaOH for saponification reaction to obtain intermediate b.

[0059] DMF, DCM or ethyl acetate was used as solvent, the reaction temperature was 30°C, and the reaction was carried out for 0.5 hours. The following two compounds were added for addition reaction to obtain intermediate c.

[0060] Fmoc-Cys-Ome Compound 1

[0061] Compound 2

[0062] Intermediate b and intermediate c use azidophosphoric acid diphenyl ester as a condensing agent, react in ...

Embodiment 3

[0065] Preparation of intermediate a: under the condition of using DMF, DCC and 3-(diethoxyphosphoryl)-1,2,3,-benzotriazin-4-one as the condensing agent, the reaction temperature is controlled at 25°C, and the reaction 8 hours. After the reaction is completed, add 20wt% liquid NaOH to carry out saponification reaction to obtain intermediate a.

[0066] DCC, ethyl acetate or benzyl chloroformate were used as solvents, the reaction temperature was controlled at 20°C, and the reaction was carried out for 8 hours. After the reaction was completed, 20 wt% liquid NaOH was added for saponification to obtain intermediate b.

[0067] DMF, DCM or ethyl acetate was used as solvent, the reaction temperature was 0°C, and the reaction was carried out for 8 hours. The following two compounds were used for addition reaction to obtain intermediate c.

[0068] Fmoc-Cys-Ome compound 1

[0069] Compound 2

[0070] Intermediate b and intermediate c use diphenylphosphoryl azido as a cond...

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Abstract

The invention discloses a preparation method of tetradecapeptide somatostatin. The method comprises the following steps: DCC and 3-(diethoxyphosphoryl)-1,2,3,-phentriazine-4-ketone are taken as condensing agents for preparing an intermediate a, the DCC is taken as a condensing agent for preparing an intermediate b, and the intermediate b and an intermediate c are condensed by taking diphenylphosphorylazide as a condensing agent to obtain an intermediate d; and the intermediate a and the intermediate b are condensed to obtain the tetradecapeptide somatostatin. The preparation method has the advantages of complete peptide linkage, mild operating condition, simple and practical purification, high yield, high optical activity and high chemical purity of the target product tetradecapeptide somatostatin. The yield of the target product tetradecapeptide somatostatin is 8-10% based on tyrosine methyl ester.

Description

technical field [0001] The present invention relates to the preparation method of medicine, specifically, the present invention is a kind of fourteen peptide somatostatin preparation method. Background technique [0002] Fourteen peptide somatostatin is a biologically active polypeptide amino acid product composed of fourteen amino acid residues. It is suitable for the treatment of acute gastric ulcer bleeding, bleeding caused by erosive and hemorrhagic gastritis, severe acute esophageal variceal bleeding, pancreaticobiliary and gastrointestinal Lou and acute pancreatitis, and the prevention of complications after pancreatic vein surgery. [0003] Fourteen peptide somatostatin has the following structural formula and simplified structural formula: [0004] [0005] Chinese patent application No. 03128951.7 (application date: May 29, 2003, publication date: December 8, 2004) discloses a synthetic method for a somatostatin polypeptide. The synthetic method uses Wang resin ...

Claims

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Application Information

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IPC IPC(8): C07K7/08A61P1/04A61P1/18A61P7/04
Inventor 吴永平刘留王思回刘纯
Owner 吴永平
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