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Octapeptide modified dexamethasone, preparation, nano-structure and application thereof

A technology of dexamethasone and -his-gly-glu, which is applied in the field of biomedicine and can solve the problems of no obvious improvement in curative effect and the like

Active Publication Date: 2016-05-18
北京恒润泰生医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there is no significant improvement in efficacy, the side effects of osteoporosis and thrombosis no longer occur

Method used

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  • Octapeptide modified dexamethasone, preparation, nano-structure and application thereof
  • Octapeptide modified dexamethasone, preparation, nano-structure and application thereof
  • Octapeptide modified dexamethasone, preparation, nano-structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation of Boc-Gly-Glu(OBzl)-OBzl

[0027] Weigh (30.0mmol) Boc-Gly5.294g, 4.353g (32.5mmol) HOBt, dissolve in dry tetrahydrofuran (THF), stir under ice bath, add 7.406g (35.9mmol) DCC dissolved in THF dropwise, stir and activate for 30 Minutes later, 15.572g (31.3mmol) TosH·Glu(OBzl)-OBzl was added, adjusted to pH=8 by NMM, reacted at room temperature for 12 hours, TLC (CH 2 Cl 2 / MeOH=20 / 1), showing that the raw material point disappeared. DCU was removed by filtration, the filtrate was concentrated under reduced pressure, the residue was dissolved in 200 mL of ethyl acetate, and the obtained ethyl acetate solution was sequentially washed with 50 mL of saturated aqueous sodium bicarbonate, 50 mL of saturated aqueous sodium chloride, 50 mL of saturated aqueous potassium hydrogensulfate, and 50 mL of saturated aqueous chlorine Aqueous sodium chloride solution, 50 mL saturated aqueous sodium bicarbonate solution, and 50 mL saturated aqueous sodium chlorid...

Embodiment 2

[0028] Example 2 Preparation of HCl Gly-Glu(OBzl)-OBzl

[0029] Add 200mL4M hydrogen chloride ethyl acetate solution to 13.0g (26.9mmol) Boc-Gly-Glu(OBzl)-OBz under ice bath, after reacting for 2 hours, TLC (CH 2 Cl 2 / MeOH=20 / 1) showed disappearance of starting point. Concentrate under reduced pressure. The residue was dissolved in anhydrous ethyl acetate and concentrated under reduced pressure. This operation was repeated 3 times. The residue was dissolved in anhydrous ether and concentrated under reduced pressure. This operation was also repeated 3 times. Yield 12.5 g (96.1%) of the title compound.

Embodiment 3

[0030] Example 3 Preparation of Boc-His(Boc)-Gly-Glu(OBzl)-OBzl

[0031] Weigh 1.400g (3.9mmol) Boc-His (Boc), 0.561g (4.0mmol) HOBt, dissolve in dry tetrahydrofuran (THF), stir under ice bath, add dropwise 0.975g (4.7mmol) DCC dissolved in THF, After stirring and activating for 30 minutes, add 2.0g (4.8mmol) HCl Gly-Glu(OBzl)-OBzl, adjust the pH to 8 with NMM, react at room temperature for 12 hours, TLC (CH2 Cl 2 / MeOH=20 / 1), showing that the raw material point disappeared. Remove DCU by filtration, concentrate the filtrate under reduced pressure, dissolve the residue with 100mL ethyl acetate, and successively wash the obtained ethyl acetate solution with saturated sodium bicarbonate 20mL saturated aqueous sodium bicarbonate, saturated 20mL aqueous sodium chloride, 20mL saturated aqueous potassium bisulfate , 20mL saturated aqueous sodium chloride solution, 20mL saturated aqueous sodium bicarbonate solution, washed 3 times with 20mL saturated aqueous sodium chloride solution...

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PUM

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Abstract

The invention discloses octapeptide Lys(AA-Asp-Gly-Arg)-His-Gly-Glu modified dexamethasone shown as the formula, wherein the AA is L-Val or L-Phe. The invention also discloses a preparation method, a nano-structure thereof, and an inhibitory effect of the compound on mouse retroauricular cardiac transplantation immunological rejective reaction and xylene induced inflammation reaction, and further discloses that the compound does not generate osteoporosis and thrombus side effects like dexamethasone. Therefore, the octapeptide modified dexamethasone disclosed by the invention has definite application prospect in preparation of immunosuppressive and anti-inflammatory drugs. (formula of the compound).

Description

technical field [0001] The invention relates to dexamethasone modified by octapeptide Lys(AA-Asp-Gly-Arg)-His-Gly-Glu, wherein AA in the octapeptide is L-Val or L-Phe residue. It relates to their preparation method, to their nanostructure, to their inhibitory effect on immune rejection of mouse myocardium transplantation behind the ear, to their inhibitory effect on xylene-induced inflammatory response, and to their further involvement that they do not Produce osteoporosis and thrombosis side effects. Therefore, the present invention relates to the application prospect of the octapeptide modified dexamethasone of the following formula in the preparation of immunosuppressive and anti-inflammatory drugs. The invention belongs to the field of biomedicine. Background technique [0002] Replacing obsolete organs through organ transplantation has become a routine treatment in clinical surgery. Immune rejection in organ transplantation is the most important factor for organ tran...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K7/06C07K1/06C07K1/02B82Y30/00A61K38/08A61P37/06A61P29/00
CPCY02P20/55
Inventor 彭师奇赵明王玉记吴建辉于化龙
Owner 北京恒润泰生医药科技有限公司
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