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Oxadiazole compounds and their application in the preparation of drugs 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: 2019-07-26
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 compounds and their application in the preparation of drugs for preventing and/or treating type 2 diabetes
  • Oxadiazole compounds and their application in the preparation of drugs for preventing and/or treating type 2 diabetes
  • Oxadiazole compounds and their application in the preparation of drugs 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-hydroxyl

[0020]

[0021] 15.4 g (0.1 mol) of 3,4-dihydroxybenzoic acid and 200 mL of absolute ethanol were added to a 500 mL flask, and 5 mL of 98% concentrated sulfuric acid was slowly added dropwise with constant stirring. The mixture was heated to reflux, 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, the aqueous layer was extracted with 300 mL of ethyl acetate, the organic layers were combined, and saturated NaHCO was added. 3 Aqueous solution, washed with saturated brine, anhydrous Na 2 SO 4 Dry, filter, and remove the solution 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 Structural Identification of p-Tolyl-2-((5-(3,4-Dihydroxyphenyl)-1,3,4-oxadiazole-2-substituted)mercapto)acetate

[0031]

[0032] 15.4 g (0.1 mol) of 3,4-dihydroxybenzoic acid and 200 mL of absolute ethanol were added to a 500 mL flask, and 5 mL of 98% concentrated sulfuric acid was slowly added dropwise with constant stirring. The mixture was heated to reflux, the reaction was followed by TLC, 80% of the solvent was evaporated under reduced pressure, diluted with 30 mL of ethyl acetate and 25 mL of water, the aqueous layer was extracted with ethyl acetate, the organic layers were combined and washed with saturated NaHCO 3 Aqueous solution, washed with saturated brine, anhydrous Na 2 SO 4 Dry, filter, and remove the solution 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, hea...

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] 15.4 g (0.1 mol) of 3,4-dihydroxybenzoic acid and 200 mL of absolute ethanol were added to a 500 mL flask, and 5 mL of 98% concentrated sulfuric acid was slowly added dropwise with constant stirring. The mixture was heated to reflux, the reaction was followed by TLC, 80% of the solvent was evaporated under reduced pressure, diluted with 30 mL of ethyl acetate and 25 mL of water, the aqueous layer was extracted with 300 mL of ethyl acetate, the organic layers were combined and washed with saturated NaHCO 3 Aqueous solution, washed with saturated brine, anhydrous Na 2 SO 4 Dry, filter, and remove the solution 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 ab...

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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 present invention relates to a new class of oxadiazole-type PTP1B inhibitors and their synthesis methods, pharmacological activities and pharmaceutical uses. The derivatives can enhance the sensitivity of insulin receptors by inhibiting the activity of PTP1B, so that the physiological function of insulin can be exerted normally, thereby regulating blood sugar, and achieving the therapeutic effect on insulin resistance type 2 diabetes mellitus. 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 347 million people with diabetes worldwide. Diabetes is divided into insulin-dependent (type 1) and insulin-resistant (type 2), with type 2 diabetes accounting for more than 90% of diabetes cases. At present, the oral drugs for the treatment o...

Claims

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Application Information

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Patent Type & Authority Patents(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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