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2-Oxadiazole-3-aminothieno[2,3-b]pyridine derivative and its preparation method and use

A technology of aminothiophene and oxadiazole, which is applied in pharmaceutical formulations, medical preparations containing active ingredients, organic chemistry, etc., can solve the problem of long treatment cycle, chronic hepatitis C treatment level that has not reached the level of developed countries, and serious side effects And other issues

Active Publication Date: 2021-06-29
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The traditional standard regimen approved by the FDA for the treatment of chronic hepatitis C is the combined application of PEG-interferon-α and ribavirin, which has the following problems: ①. Low effective rate; ②. Long treatment cycle and high treatment cost ; ③. Toxic and side effects are more serious
[0007] In my country, the infection level of HCV is slightly higher than the world average level, but due to the long incubation period of HCV infection, most cases have developed into liver cirrhosis and liver cancer when they are diagnosed with chronic hepatitis C, so the treatment of chronic hepatitis C in my country far below the level of developed countries

Method used

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  • 2-Oxadiazole-3-aminothieno[2,3-b]pyridine derivative and its preparation method and use
  • 2-Oxadiazole-3-aminothieno[2,3-b]pyridine derivative and its preparation method and use
  • 2-Oxadiazole-3-aminothieno[2,3-b]pyridine derivative and its preparation method and use

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preparation example Construction

[0054] The preparation method of 2-oxadiazole-3-aminothieno[2,3-b]pyridine derivatives comprises the following steps: intermediate A and raw material B in the reaction formula are prepared by substitution reaction and ring closure reaction to obtain formula I compound.

[0055] In the above preparation method of 2-oxadiazole-3-aminothieno[2,3-b]pyridine derivatives, the molar ratio of the intermediate A to the raw material B is 1:1. The solvent of the substitution reaction is at least one of dichloromethane, THF, DMF or DMSO; the temperature of the substitution reaction is 0-30°C; the time of the substitution reaction is 0.5-2h. The reagents of the ring-closing reaction include POCl 3 , p-toluenesulfonyl chloride, triethylamine or N-methylpyrrolidone; the temperature of the ring-closing reaction is 20-100°C; the time of the ring-closing reaction is 1-12h.

[0056] In the preparation method of the above-mentioned 2-oxadiazole-3-aminothieno[2,3-b]pyridine derivatives, the desc...

Embodiment 1

[0067] Example 1 Synthesis of 1-benzenebutane-1,3-dione (intermediate 1-1.1)

[0068]

[0069] After the excess ethanol was distilled off from the freshly prepared sodium ethoxide solution under reduced pressure, the residual EtONa (sodium ethoxide) solid (25 mmol) was added to 20 mL of THF, and stirred for half an hour in an ice bath. Then slowly add acetophenone (2.4g, 20mmol) dropwise therein, and gradually raise the temperature to react at room temperature for 12h. After the reaction solution is cooled, the solvent is evaporated under reduced pressure, and the residual solid is dissolved in distilled water and the pH is adjusted with dilute hydrochloric acid under stirring. to weak acidity, then extracted the mixed solution with ethyl acetate and water, washed the ethyl acetate layer with saturated brine (50mL×2), dried over anhydrous magnesium sulfate, evaporated the solvent under reduced pressure to obtain 2.045g of crude product, yield 63.05 %. ESI-MS[M-H] - (m / z):...

Embodiment 2

[0070] Example 2 Synthesis of 1-cyclopropyl-4,4,4-trifluorobutane-1,3-dione (intermediate 1-1.2)

[0071]

[0072] Slowly add NaH (sodium hydride, 60%, 1.2g, 30mmol) into dry THF (tetrahydrofuran) under an ice bath, and after cooling, add ethyl trifluoroacetate (4.262g, 30mmol) to it, and stir under an ice bath Half an hour later, cyclopropylmethyl ketone (1.682 g, 20 mmol) was slowly added dropwise to the reaction solution, and then the temperature was slowly raised to room temperature and the reaction was continued for 12 hours. The solvent was evaporated under reduced pressure, the residual solid was dissolved in distilled water, and the pH was adjusted to weak acidity with dilute hydrochloric acid, then extracted with ethyl acetate, the ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure to obtain Brown oily crude product 3.024g, yield 84.01%. ESI-MS [M+H]+(m / z): 181.0.

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Abstract

The invention belongs to the field of chemical pharmacy, and specifically relates to 2-oxadiazole-3-aminothieno[2,3-b]pyridine derivatives and their preparation methods and uses. The present invention provides a 2-oxadiazole-3-aminothieno[2,3-b]pyridine derivative, the structure of which is shown in formula I. The present invention also provides the above-mentioned 2-oxadiazole-3-aminothieno[2,3-b]pyridine derivatives to the preparation method and application. The 2-oxadiazole-3-aminothieno[2,3-b]pyridine derivative compound provided by the present invention has good HCV inhibitory effect and exhibits low cytotoxicity. Provide new ideas for the development of anti-HCV inhibitors.

Description

[0001] The application number is 201511019800.9, the application date is December 31, 2015, and the invention name is "2-oxadiazole-3-aminothieno[2,3-b]pyridine derivatives and their preparation methods and uses "A divisional application of the invention patent application. technical field [0002] The invention belongs to the field of chemical pharmacy, and specifically relates to 2-oxadiazole-3-aminothieno[2,3-b]pyridine derivatives and their preparation methods and applications. Background technique [0003] Chronic hepatitis C, a chronic liver disease caused by the hepatitis C virus (HCV), is the leading cause of cirrhosis and liver cancer, and is currently the leading cause of liver transplantation. According to the survey of the World Health Organization (WHO) in 1999, about 3% of people (170 million people) in the world are infected with HCV (J.Viral.Hepat.1999,6:35-47), and the infection rate in China is about 3.2% (40 million people) (Lancet Infect.Dis.2005.5:558–6...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A61K31/4365A61P31/20
CPCC07D495/04
Inventor 余洛汀魏于全
Owner SICHUAN UNIV
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