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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 ingredients, medical preparations of non-active ingredients, non-effective ingredients of polymer compounds, etc., can solve the problem of cyclosporin A's poor water solubility, dosage form and curative effect Unsatisfactory, strong nephrotoxicity and other problems, to achieve excellent immunosuppressive effect

Inactive Publication Date: 2012-05-23
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 1

[0028] Example 1 Preparation of Boc-Asp(OBzl)-Gly-OBzl

[0029] 8.08g (25.00mmol) Boc-Asp (OBzl) was dissolved in 200ml dry THF, 3.38g (25.00mmol) N-hydroxybenzotriazole (HOBt) was added to the resulting solution under ice bath, and 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. Under ice bath, 8.43g (25.00mmol) TosH·Gly-OBzl was suspended in 20ml anhydrous THF, and then 1ml N-methylmorpholine (NMM) was added to adjust the pH to 8-9. Stir for 35 minutes to obtain reaction solution (II), which is set aside. The reaction solution (I) was added to the reaction solution (II) in an ice bath, and the mixture was 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 ...

Embodiment 2

[0030] Example 2 Preparation of HCl·Asp(OBzl)-Gly-OBzl

[0031] 11.04g (23.50mmol) Boc-Asp(OBzl)-Gly-OBzl was dissolved in 250ml of 4mol / l hydrogen chloride-ethyl acetate solution, stirred at room temperature for 2 hours, TLC (chloroform: methanol, 5:1) showed that the starting material point disappeared , Concentrate under reduced pressure to remove ethyl acetate, and add a small amount of ether to the residue repeatedly and concentrate under reduced pressure to remove hydrogen chloride. Finally, a small amount of ether was added to grind the residue into 9.17 g (96%) of the title compound, which was a colorless solid powder, which was directly used in the next reaction. ESI-MS(m / z): 371[M+H] + .

Embodiment 3

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

[0033] According to the method of Example 1, from 7.61 g (22.56 mmol) Boc-Glu (OBzl) and 9.17 g (22.56 mmol) HCl·Asp(OBzl)-Gly-OBzl, a beige oil was obtained. The obtained compound was purified by silica gel column chromatography to obtain 10.73 g of a colorless oily target. Purification conditions: 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 acid tripeptide amides, in particular to a series of saturated fatty acid Glu-Asp-Gly tripeptide amides with immunosuppressive activity, and also relates to the preparation method of these saturated fatty acid tripeptide amides and their use as immune The application of inhibitors belongs to the field of biomedicine. Background technique [0002] According to statistics, as of the end of 2002, a total of 935,792 organ transplants were performed globally, including 585,877 kidney transplants, 112,153 liver transplants, and 66,559 heart transplants. In addition, organ transplants such as pancreas, lungs, and small intestines, as well as multiple organ transplants such as heart-lung, pancreas-kidney, liver-kidney, liver-intestine, etc., have also been successful and applied clinically. At present, the 1-year human / kidney survival rate of kidney transplantation reaches 90%-95%, and the 5-year survival rate excee...

Claims

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Application Information

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Patent Type & Authority Patents(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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