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Saturated fatty chain acid Glu-Asp-Gly tripeptide amide, synthetic method and application thereof

A technology of glu-asp-gly and fatty chain acid, which is applied in the direction of tripeptide components, peptide preparation methods, chemical instruments and methods, etc., can solve cyclosporine A's poor water solubility, dosage form or unsatisfactory curative effect, kidney disease, etc. Strong toxicity and other issues, to achieve excellent immunosuppressive effect

Inactive Publication Date: 2010-12-01
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the extremely poor water solubility and strong nephrotoxicity of cyclosporin A, neither the dosage form nor the curative effect is satisfactory

Method used

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  • Saturated fatty chain acid Glu-Asp-Gly tripeptide amide, synthetic method and application thereof
  • Saturated fatty chain acid Glu-Asp-Gly tripeptide amide, synthetic method and application thereof
  • Saturated fatty chain acid Glu-Asp-Gly tripeptide amide, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1B

[0028] The preparation of embodiment 1Boc-Asp(OBzl)-Gly-OBzl

[0029] 8.08g (25.00mmol) Boc-Asp (OBzl) was dissolved in 200ml anhydrous THF, and 3.38g (25.00mmol) N-hydroxybenzotriazole (HOBt) was added to the solution obtained under ice-cooling, and made completely dissolved. After 10 minutes, 6.20 g (30 mmol) of dicyclohexylcarbodiimide (DCC) was added to obtain the reaction solution (I), which was set aside. Suspend 8.43g (25.00mmol) TosH·Gly-OBzl in 20ml anhydrous THF under ice-cooling, then add 1ml N-methylmorpholine (NMM) to adjust the pH to 8-9. Stir for 35 minutes to obtain the reaction solution (II), which is ready for use. The reaction solution (I) was added to the reaction solution (II) under ice bath, stirred for 1 h under ice bath, and then stirred at room temperature for 12 h. TLC (chloroform / methanol, 10:1) showed that Boc-Asp(OBzl)-OH disappeared. Dicyclohexylurea (DCU) was filtered off and THF was removed under reduced pressure. The residue was dissolved w...

Embodiment 2

[0030] The preparation of embodiment 2HCl Asp (OBzl)-Gly-OBzl

[0031] Dissolve 11.04g (23.50mmol) Boc-Asp(OBzl)-Gly-OBzl in 250ml 4mol / l hydrogen chloride-ethyl acetate solution, stir at room temperature for 2 hours, TLC (chloroform:methanol, 5:1) shows that the raw material point disappears , concentrated under reduced pressure to remove ethyl acetate, and the residue was repeatedly added with a small amount of ether for concentration under reduced pressure to remove hydrogen chloride gas. Finally, a small amount of diethyl ether was added to triturate the residue to obtain 9.17 g (96%) of the title compound as a colorless solid powder, which was directly used in the next reaction. ESI-MS(m / z): 371[M+H] + .

Embodiment 3B

[0032] Embodiment 3 Preparation of Boc-Glu(OBzl)-Asp(OBzl)-Gly-OBzl

[0033] According to the method of Example 1, a beige oil was obtained from 7.61 g (22.56 mmol) Boc-Glu (OBzl) and 9.17 g (22.56 mmol) HCl·Asp (OBzl)-Gly-OBzl. The obtained compound was purified by silica gel column chromatography to obtain 10.73 g of a colorless oily product, the purification condition: chloroform:methanol=100:1, and the yield was 69%. ESI-MS(m / z): 690[M+H] + , [α] 20 D =-24.4 (c=1.0, CH 3 OH).

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Abstract

The invention relates to 6 saturated fatty chain acid Glu-Asp-Gly tripeptide amide conjugates with immunosuppressive activity in a general formula CH3 (CH2)n-CO-Glu-Asp-Gly I. In saturated fatty chain acid, n is equal to 6, 8, 10, 12, 14 or 16. The invention also relates to a preparation method and application of the conjugates as an immunosuppressant. An experimental result of the saturated fatty chain acid Glu-Asp-Gly tripeptide ester which has the inhibition effects of splenic lymphocyte mitogen breeder reaction and macrophage phagocytosis activity indicates that the conjugates of the invention have excellent immunosuppressive action and can be clinically used as an immunosuppressant.

Description

technical field [0001] The present invention relates to saturated fatty chain acid tripeptide amides, especially to a series of saturated fatty chain acid Glu-Asp-Gly tripeptide amides with immunosuppressive activity, and also to the preparation method of these saturated fatty chain acid tripeptide amides and their use as immune The application of the inhibitor belongs to the field of biomedicine. Background technique [0002] According to statistics, by the end of 2002, a total of 935,792 cases of various organ transplants had been performed in the world, including 585,877 cases of kidney transplants, 112,153 cases of liver transplants, and 66,559 cases of heart transplants. In addition, pancreas, lung, small intestine and other organ transplants, as well as multi-organ transplants such as heart-lung, pancreas-kidney, liver-kidney, and liver-intestine, have also been successfully applied in clinical practice. Currently, the 1-year human / kidney survival rate of kidney trans...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K5/093C07K1/06C07K1/02A61K38/06A61P37/06A61K47/42A61K9/107A61K9/127A61K47/64A61K47/69
CPCY02P20/55
Inventor 赵明彭师奇赵淑锐
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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