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Oxadiazole compound and application thereof to preparation of medicament for preventing and/or treating type 2 diabetes

A technology of type 2 diabetes and oxadiazoles, which is applied in the field of oxadiazole compounds and their application in the preparation of drugs for the prevention and/or treatment of type 2 diabetes, and can solve the problems of low cell permeability and bioavailability, Problems such as high hydrophilicity and electronegativity

Inactive Publication Date: 2017-05-10
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since most of these compounds contain phosphate or carboxylic acid groups, their high hydrophilicity and electronegativity lead to their cell permeability and bioavailability are too low

Method used

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  • Oxadiazole compound and application thereof to preparation of medicament for preventing and/or treating type 2 diabetes
  • Oxadiazole compound and application thereof to preparation of medicament for preventing and/or treating type 2 diabetes
  • Oxadiazole compound and application thereof to preparation of medicament for preventing and/or treating type 2 diabetes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Synthesis and structural identification of 4-(5-(benzylthio)-1,3,4-oxadiazole-2-substituted)benzene-1,2-hydroxy

[0020]

[0021] Add 15.4g (0.1mol) of 3,4-dihydroxybenzoic acid and 200mL of absolute ethanol into a 500mL flask, and slowly add 5mL of concentrated sulfuric acid with a mass fraction of 98% dropwise under continuous stirring. The mixture was heated to reflux, and the reaction was followed by TLC. 80% of the volume of the solvent was evaporated under reduced pressure, diluted with 30 mL of ethyl acetate and 25 mL of water, and the aqueous layer was extracted with 300 mL of ethyl acetate. The combined organic layers were washed with saturated NaHCO 3 aqueous solution, saturated brine washing, anhydrous Na 2 SO 4 Dry, filter, and desolvate under reduced pressure to obtain 15.8 g of ethyl 3,4-dihydroxybenzoate with a yield of 86.8%.

[0022] Take 15.8g of the solid ethyl 3,4-dihydroxybenzoate from the previous step, add it to 100mL of absolute e...

Embodiment 2

[0030] Example 2: Synthesis and structure identification of p-tolyl-2-((5-(3,4-dihydroxyphenyl)-1,3,4-oxadiazole-2-substituted) mercapto) acetate

[0031]

[0032] Add 15.4g (0.1mol) of 3,4-dihydroxybenzoic acid and 200mL of absolute ethanol into a 500mL flask, and slowly add 5mL of concentrated sulfuric acid with a mass fraction of 98% dropwise under continuous stirring. The mixture was heated to reflux, followed by TLC, 80% of the solvent was evaporated under reduced pressure, diluted with 30mL ethyl acetate and 25mL water, the aqueous layer was extracted with ethyl acetate, the combined organic layers were washed with saturated NaHCO 3 aqueous solution, saturated brine washing, anhydrous Na 2 SO 4 Dry, filter, and desolvate under reduced pressure to obtain 15.8 g of ethyl 3,4-dihydroxybenzoate with a yield of 86.8%.

[0033]Take 15.8g of the solid ethyl 3,4-dihydroxybenzoate from the previous step, add it to 100mL of absolute ethanol, heat at 60°C, slowly add 37.5g (0....

Embodiment 3

[0041] Example 3: Synthesis and structure of 3-ethoxybenzene 2-((5-(3,4-dihydroxyphenyl)-1,3,4-oxadiazole-2-substituted) mercapto) acetate identification

[0042]

[0043] Add 15.4g (0.1mol) of 3,4-dihydroxybenzoic acid and 200mL of absolute ethanol into a 500mL flask, and slowly add 5mL of concentrated sulfuric acid with a mass fraction of 98% dropwise under continuous stirring. The mixture was heated to reflux, followed by TLC, 80% of the solvent was evaporated under reduced pressure, diluted with 30 mL ethyl acetate and 25 mL water, the aqueous layer was extracted with 300 mL ethyl acetate, the combined organic layers were washed with saturated NaHCO 3 aqueous solution, saturated brine washing, anhydrous Na 2 SO 4 Dry, filter, and desolvate under reduced pressure to obtain 15.8 g of ethyl 3,4-dihydroxybenzoate with a yield of 86.8%.

[0044] Take 15.8g of the solid ethyl 3,4-dihydroxybenzoate from the previous step, add it to 100mL of absolute ethanol, heat at 60°C, s...

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Abstract

The invention relates to a total chemical synthesis method for novel oxadiazole PTP1B (protein tyrosine phosphatase 1B) and application of the novel oxadiazole PTP1B to a medicament for treating type 2 diabetes. The structural formula of the oxadiazole compound is shown in the description. The activity of PTP1B is inhibited, and the sensitivity of an insulin receptor is enhanced, so that the compound has good treatment effects on insulin resistance type 2 diabetes.

Description

technical field [0001] The invention relates to a new class of oxadiazole PTP1B inhibitors and its synthesis method, pharmacological activity and pharmaceutical application. The derivatives inhibit the activity of PTP1B, enhance the sensitivity of insulin receptors, make the physiological function of insulin normally play, and then regulate blood sugar, so as to achieve the therapeutic effect on insulin-resistant type 2 diabetes. Background technique [0002] Diabetes mellitus is a chronic metabolic disease caused by insufficient insulin secretion or decreased sensitivity of target tissues to insulin. According to data released by the World Health Organization (WHO) in November 2014, there are as many as 347 million diabetic patients worldwide. Diabetes is divided into insulin-dependent (type 1) and insulin-resistant (type 2), of which type 2 diabetes patients account for more than 90% of diabetes cases. Oral drugs currently on the market for the treatment of type 2 diabet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/113A61K31/4245A61P3/10
CPCC07D271/113
Inventor 史大永李祥乾王立军江波
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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