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Beta-L-2'-desoxy-thymin-nucleoside derivative, preparation method and purposes thereof

A technology of thymidine derivatives and thymidine, which is applied in the field of chemical medicine and can solve the problems of easy drug resistance of viruses, nephrotoxicity, and easy rebound after drug withdrawal

Inactive Publication Date: 2015-03-25
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, telbivudine has the following disadvantages: potential nephrotoxicity, drug resistance of the virus, the body's dependence on the drug, easy rebound after drug withdrawal, treatment must be started when the liver is onset, and some patients have rhabdomyolysis Tendency etc.

Method used

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  • Beta-L-2'-desoxy-thymin-nucleoside derivative, preparation method and purposes thereof
  • Beta-L-2'-desoxy-thymin-nucleoside derivative, preparation method and purposes thereof
  • Beta-L-2'-desoxy-thymin-nucleoside derivative, preparation method and purposes thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 52

[0250] Example 52, 4-dithio-2'-deoxy-L-thymidine

[0251]

[0252] a. Synthesis of Compound 19

[0253] Take 7.8g of compound 14, add 200ml of anhydrous pyridine, stir to dissolve, add 7.5ml of benzoyl chloride, heat to 50°C and react for 10-20 hours, after the reaction is detected by TLC, concentrate to about 30ml, add crushed ice while stirring, A precipitate was formed, filtered, dried under pressure, and recrystallized from ethanol to obtain 12.5 g of compound 19.

[0254] b. Synthesis of Compound 20

[0255] Take 9.4g of compound 19, add 200ml of dioxane, stir to dissolve, add 14g of Lawson's reagent, reflux reaction, TLC monitors the reaction progress, after the reaction is completed, concentrate to dryness, add water, extract with chloroform, the water layer is concentrated to dryness, and the column Chromatography yielded 8.5 g of compound 20.

[0256] c. Synthesis of Compound 21

[0257] Take 7g of compound 20, add 200ml of methanol, stir to dissolve, add 1.8g ...

Embodiment 72

[0266] Example 72, 4-diselenium-2'-deoxy-L-thymidine

[0267]

[0268] a. Synthesis of Compound 25

[0269] 35ml POCl 3 Add dropwise to containing 100g1,2, in the anhydrous acetonitrile suspension (1000ml) of 4-triazole, N 2 protection, stirred at 0°C for 10 min; then 200ml of anhydrous Et 3 N was added dropwise to the above mixed solution, and stirred at 0°C for 35 min; finally, acetonitrile solution (500 ml) in which 11 g of compound 22 was dissolved was added, and the reaction was stirred at room temperature. TLC detected that the raw material point disappeared, and about 200 ml of saturated NaHCO was added. 3 , and then extracted with ethyl acetate, washed with water, dried and concentrated to obtain 10.6 g of compound 25.

[0270] b. Synthesis of Compound 26

[0271] 3gNaBH 4 Add to containing 6ml (NCCH 2 CH 2 Se) 2 and 200ml of ethanol in a round bottom flask, ice bath, N 2 A solution of 10 g of compound 25 in THF (100 ml) was added under protection, and the ...

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Abstract

The invention belongs to the technical field of chemical medicines, and particularly relates to a Beta-L-2'-desoxy-thymine nucleoside derivative, a preparation method and purposes thereof. The Beta-L-2'-desoxy-thymine nucleoside derivative has a structure as showed in a format I, wherein R1 and R2 are independent O, S or Se; when one of the R1 and the R2 is O, R3 is halogen, -OH, -NH2, C1-C8 alkyl, (CH2)nF, (CH2)n-1CHF or CF3; R4 is halogen, H, or CF3; and n is 1-8. The invention provides the derivative which has activity of resisting hepatitis virus, and offers a new choice for preparing medicines capable of treating the hepatitis.

Description

technical field [0001] The invention belongs to the technical field of chemistry and medicine, and in particular relates to β-L-2'-deoxy-thymidine derivatives and their preparation methods and applications. Background technique [0002] Chronic hepatitis B (CHB) is a globally widespread infectious disease. Hepatitis B virus (HBV) infection is a great challenge to global public health. According to the statistics of the World Health Organization (WHO), among the approximately 2 billion people who have been infected with hepatitis B virus (HBV) in the world, more than 400 million people suffer from chronic hepatitis B virus infection, and about 1 million patients die of HBV every year. Cirrhosis or liver cancer associated with hepatitis virus infection (Kim KH, Kim ND, Seong BL. Molecules, 2010, 15(9):5878-5908). What's more serious is that 75% of the global hepatitis B virus infections are distributed in Asia. There are approximately 120 million hepatitis B virus-infected p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C07D405/14C07D498/08A61K31/513A61K31/506A61P31/20A61P1/16
Inventor 谢永美魏于全李炯
Owner SICHUAN UNIV
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