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Compound for preventing or treating autoimmune diabetes and preparation method and application thereof

An autoimmune and compound technology, applied in the direction of steroids, allergic diseases, medical preparations containing active ingredients, etc., to achieve the effect of preventing or treating autoimmune diabetes

Inactive Publication Date: 2012-10-03
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no report on the preparation of diosgenin, ibuprofen or aspirin into twin drugs for the treatment of autoimmune diabetes

Method used

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  • Compound for preventing or treating autoimmune diabetes and preparation method and application thereof
  • Compound for preventing or treating autoimmune diabetes and preparation method and application thereof
  • Compound for preventing or treating autoimmune diabetes and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0037] Example 12 - Preparation of Diosgenin Acetoxybenzoate (Compound 2):

[0038] (1) Preparation of 2-acetoxybenzoyl chloride:

[0039]

[0040] In a 50ml reaction vial, add aspirin (4.50g, 25mmol), 2 drops of N,N'-dimethylformamide (DMF) and 3ml of thionyl chloride SOCl 2 (36mmol), quickly connect the spherical condenser (calcium chloride drying tube is installed on the top), and import the tail gas into the sodium hydroxide solution for absorption. Slowly heat up to 70°C under stirring, and keep this temperature constant until no bubbles emerge from the tail gas end. Remove excess thionyl chloride by suction filtration under reduced pressure to obtain light yellow oily liquid, namely 2-acetoxybenzoyl chloride. (TLC: chloroform:methanol=9:1, R f =0.83); Dissolve 2-acetoxybenzoyl chloride in tetrahydrofuran THF to make 25ml of liquid, and seal it for later use.

[0041] (2) Preparation of diosgenin 2-acetoxybenzoate:

[0042]

[0043] Into a 150ml three-necked fl...

Embodiment 2

[0044] Example 2 Preparation of N-(2-acetoxybenzoyl)-glycine diosgenin ester (compound 3)

[0045] (1) Preparation of 2-acetoxybenzoyl chloride:

[0046]

[0047]In a 50ml reaction bottle, add 4.50g (25mmol) of aspirin, 2 drops of N,N'-dimethylformamide DMF and 3ml of thionyl chloride SOCl 2 (36mmol), quickly connect the spherical condenser (calcium chloride drying tube is installed on the top), and import the tail gas into the sodium hydroxide solution for absorption. Slowly heat up to 70°C under stirring, and keep this temperature constant until no bubbles emerge from the tail gas end. Excess thionyl chloride was removed by suction filtration under reduced pressure to obtain 2-acetoxybenzoyl chloride as an oily liquid. (Chloroform:methanol=9:1, Rf=0.83; dissolve 2-acetoxybenzoyl chloride in tetrahydrofuran THF to make 25ml of liquid, sealed for later use)

[0048] (2) Preparation of N-tert-butoxycarbonylglycine diosgenin ester

[0049]

[0050] In a 50ml reaction b...

Embodiment 32

[0057] Example 32- Preparation of (4-isobutylphenyl) diosgenin propionate (compound 4):

[0058]

[0059] 1.03g (5mmol) of ibuprofen, 2.07g (5mmol) of diosgenin, 1g of 4A molecular sieve, 122mg (1mmol) of 4-dimethylaminopyridine DMAP, 172mg (0.2mmol) of p-toluenesulfonic acid TsOH, 100ml of anhydrous dichloromethane, add dropwise N,N'-dicyclohexylcarbodiimide DCC 1.55g (7.5mmol, dissolved in 50ml of anhydrous dichloromethane) under stirring at room temperature, and check the progress of the reaction by TLC until the reaction is no longer Go, filter. After the filtrate was washed several times with 10g / L citric acid solution and saturated sodium chloride solution successively, it was washed with anhydrous sodium sulfate Na 2 SO 4 Dry and separate on a silica gel column to obtain diosgenin 2-(4-isobutylphenyl)propionate as a white solid, 2.14 g. (Petroleum ether: ethyl acetate=4:1, Rf=0.68) 1H NMR (400MHz, CDCl3) δ7.20(d, J=7.8Hz, 2H), 7.08(d, J=7.7Hz, 2H), 5.34 (dd,J=15....

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PUM

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Abstract

The invention discloses a compound for preventing or treating autoimmune diabetes, and the structure of the compound is shown in a general formula 1. The invention also discloses a preparation method and an application of the compound. The twin drug compound of diosgenin and ibuprofen or aspirin provided by the invention not only can effectively prevent or treat autoimmune diabetes caused by the damage of beta cells of pancreas islet, but also has better effects of anti-inflammation, analgesia and the like, and a new choice is provided for clinical medication.

Description

technical field [0001] The invention relates to a compound for preventing or treating autoimmune diabetes and its preparation method and application, belonging to the field of medicine. Background technique [0002] Autoimmune diabetes mainly includes type 1 diabetes mellitus (T1DM) and latent autoimmune diabetes of adults (LADA). Among them, type 1 diabetes is an autoimmune disease mediated by T cells. It is based on genetics. Under the action of certain environmental factors, it induces the autoimmune response of pancreatic β cells with the pathological characteristics of insulitis, and damages β cells. It loses the function of synthesizing and secreting insulin, causing glucose metabolism disorder. Latent autoimmune diabetes in adults, its initial clinical manifestations are similar to type 2 diabetes, but the pathogenesis and outcome are the same as those of T1DM, and the difference from T1DM is that the immune damage of the islet β cells of LADA develops slowly. After...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61K31/625A61K31/58A61P29/00A61P3/10A61P37/02
Inventor 黄文何杨吴晓华陆燕蓉程惊秋
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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