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N-aryl-2-thiophene amide derivative, method for preparing same and application of N-aryl-2-thiophene amide derivative

A technology of thiophene carboxylic acid and carboxyl, which is applied in the field of medicine and can solve problems such as unsatisfactory patients, attenuation of pancreatic β-cell function, and substandard blood sugar of patients.

Active Publication Date: 2017-08-11
广州南方医大科技园有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Type 2 diabetes accounts for more than 90% of the total number of diabetics. Although there are many traditional drugs such as metformin, sulfonylurea and non-sulfonylurea insulin secretagogues, thiazolidinediones, α-glucosidase inhibitors, insulin and Incretin-based therapy developed in the past ten years, including glucagon-like peptide-1 (GLP-1) agonist and dipeptidyl peptidase-4 (DPP-4) inhibitor, etc. , but the blood sugar of most patients still does not reach the target
The main reason is that with the progress of the disease, the function of pancreatic β-cells is attenuated, and the current treatment methods still cannot meet the needs of patients.

Method used

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  • N-aryl-2-thiophene amide derivative, method for preparing same and application of N-aryl-2-thiophene amide derivative
  • N-aryl-2-thiophene amide derivative, method for preparing same and application of N-aryl-2-thiophene amide derivative
  • N-aryl-2-thiophene amide derivative, method for preparing same and application of N-aryl-2-thiophene amide derivative

Examples

Experimental program
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Embodiment 1

[0028] The synthetic method of embodiment 1N-(2-(4-chlorobenzoyl) phenyl)-5-bromothiophene-2-carboxamide Y1

[0029] Add 5-bromo-2-thiophenecarboxylic acid (1mmol, 206mg), 3mL thionyl chloride, and 3 drops of pyridine into a 50mL round-bottomed flask, stir and heat and add flow (80°C). After 2 hours, stop the reaction and rotate The solvent was removed by evaporation to obtain 5-bromo-2-thienyl chloride, which was added to 5 mL of dry dichloromethane for later use. Add 2-amino-4'-chlorobenzophenone (1 mmol, 232 mg), 5 mL of dichloromethane, and 1 mL of triethylamine into a 50 mL round bottom flask, stir to dissolve, and cool to 0° C. in an ice-water bath. Under stirring, a dichloromethane solution of 5-bromo-2-thiophene acid chloride was added dropwise (dropped within 10 minutes), and after the dropwise addition was completed, the stirring reaction was continued for 2 hours. Stop the reaction, remove the solvent under reduced pressure with a rotary evaporator, and separate an...

Embodiment 2

[0031] Example 2 Detection of insulin secretion-stimulating activity of N-(2-(4-chlorobenzoyl)phenyl)-5-bromothiophene-2-carboxamide Y1

[0032] Insulin-stimulating activity was detected by rat insulinoma cells INS-832 / 13 cells. INS-832 / 13 cells were cultured in RPMI1640 medium containing 10% fetal bovine serum, 10mM hydroxyethylpiperazine ethanesulfonic acid, 2mM L-glutamate, 1mM sodium pyruvate, 0.05mM mercaptoethanol, placed Contains 5% CO 2 cultured in a cell culture incubator.

[0033] INS-832 / 13 cells take 10 5 Plate / well in 24-well plate, 37°C, 5% CO 2 Incubate for 48 hours. When the cells grow well, suck out the RPMI1640 medium, add sugar-free buffer solution (115mM sodium chloride, 5mM potassium chloride, 24mM sodium bicarbonate, 2.5mM calcium chloride, 1mM magnesium chloride, 10mM hydroxyethylpiperazine ethylsulfur acid, 0.1% bovine serum albumin, pH7.2) for 2 hours, and then replaced with buffer solutions containing 2.5mM and 16.7mM glucose concentrations and 1...

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Abstract

The invention discloses an N-aryl-2-thiophene amide derivative, a method for preparing the same and application of the N-aryl-2-thiophene amide derivative, and particularly discloses a compound and pharmaceutically acceptable salt of the compound. The structure of the N-aryl-2-thiophene amide derivative is shown as a formula I. The compound and the pharmaceutically acceptable salt of the compound can be used for treating or preventing hyperglycemia, diabetes mellitus, impaired glucose tolerance and insulin resistance.

Description

technical field [0001] The invention relates to the field of medicine, in particular to an N-aryl-2-thiophene amide derivative used for treating type 2 diabetes. Background technique [0002] Diabetes is a worldwide prevalent chronic disease that seriously threatens human health. In 2015, there were 415 million diabetics in the world, and it is expected to reach 642 million by 2040, and the number of deaths from diabetes will reach 4.9 million. On average, one diabetic will die every 7 seconds, and more than 612 billion US dollars will be spent on the prevention and treatment of diabetes. global economic burden. my country is a big country with diabetes. There are 114 million diabetic patients in the country, accounting for about 1 / 4 of the global total. This has a huge impact on my country's population health and social and economic development. Therefore, there is an urgent need to develop effective means for treating diabetes. [0003] Type 2 diabetes accounts for more...

Claims

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Application Information

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IPC IPC(8): C07D333/38A61P3/10A61P3/08A61P5/50
CPCC07D333/38
Inventor 姚新刚陈之朋吴文玉刘叔文
Owner 广州南方医大科技园有限公司
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