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Chemical modified adefovir and tynofovir

A technology of compounds and derivatives, applied in the field of chemically modified adefovir and tenofovir, can solve the problems of slow phosphorylation of host cells and ineffective concentration

Active Publication Date: 2007-04-18
LIANYUNGANG RUNZHONG PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the core antigen of hepatitis B virus exists in the liver cells, nucleoside drugs need to enter the liver cells and be effective after phosphorylation catalyzed by thymidine kinase. The cells lack thymidine kinase, the phosphorylation of host cells is slow, and the effective concentration for inhibiting virus replication cannot be reached. Large doses of drugs can increase the blood drug concentration, but the drug that has not been phosphorylated in the blood can quickly pass through the kidneys. Toxic side effects such as hematuria and renal dysfunction due to excretion (World Chin J Digestol 2003 June; 11(6):799-802)

Method used

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  • Chemical modified adefovir and tynofovir
  • Chemical modified adefovir and tynofovir
  • Chemical modified adefovir and tynofovir

Examples

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Embodiment 1

[0050]The preparation of embodiment 1 adefovir-methoxypolyethylene glycol 2000

[0051] Add 140g (0.07mol) of monomethoxypolyethylene glycol 2000 (mPEG2000) into 500ml of toluene, heat and melt, evaporate about 400ml of toluene, add 250ml of N,N-dimethylformamide, 70ml of pyridine, 9.6 g (0.035mol) adefovir and 27g dicyclohexylcarbodiimide, heat up to 100°C, and react at this temperature for 120 minutes, cool to room temperature, add 1000ml ethyl acetate, stir for 2 hours, filter, The solvent was recovered from the mother liquor, 500ml of absolute ethanol was added to the residue to dissolve, and then slowly added into 2000ml of anhydrous diethyl ether with vigorous stirring, cooled, filtered, and the filter cake was dried under reduced pressure at room temperature for 24 hours to obtain 130g. Melting point 49~52℃, containing 6.8% adefovir.

Embodiment 2

[0052] Embodiment 2 Preparation of Adefovir-methoxypolyethylene glycol amine 2000

[0053] 140g (0.07mol) polyethylene glycol amine 2000 (mPEG-NH 2 ) into 250ml of N,N-dimethylformamide, add 9.6g (0.035mol) of adefovir and 21g of DCM, stir at room temperature for 24 hours, add 1000ml of ethyl acetate, stir for 2 hours, filter, and recover the solvent from the mother liquor , 500ml of absolute ethanol was added to the residue to dissolve, then slowly added into 2000ml of anhydrous ether which was stirred vigorously, cooled, filtered, and the filter cake was dried under reduced pressure at room temperature for 24 hours to obtain 126g of product. Melting point 49~53℃, containing 6.8% adefovir.

Embodiment 3

[0054] Embodiment 3 Preparation of Adefovir-methoxypolyethylene glycol 1000

[0055] Prepared according to the method of Example 1, the molar ratio of monomethoxypolyethylene glycol 1000 and adefovir was 2:1, and adefovir polyethylene glycol 1000 was obtained, with a melting point of 34-38 ° C, containing adefovir Foway 13.6%.

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Abstract

A chemically modified adefovir and tenofovir is prepared through the combination of adefovir (or tenofovir) with polyethanediol (or glycosylated polyethanediol). Their preparing process and their antiviral application are also disclosed.

Description

technical field [0001] The present invention relates to the chemical modification of drug molecules to improve the deficiencies of existing drugs, specifically the combination of Adefovir (Adefovir, PMEA) or tenofovir (tenofovir, PMPA) and polyethylene glycol, Adefovir (PMEA) The combination of defovir or tenofovir and glycosylated polyethylene glycol also relates to their preparation method and antiviral application. Background technique [0002] Adefovir and Tenofovir are nucleoside analogues with similar structures and have broad-spectrum antiviral activity. Their structural formulas are: [0003] [0004] Where A can choose H or CH 3 , when A represents H, it is adefovir; when A represents CH 3 At that time, it was tenofovir. [0005] Clinical trials have found that both adefovir and tenofovir have good anti-AIDS virus (HIV) and hepatitis B virus (HBV) activities. Experiments have confirmed that adefovir and tenofovir have significant inhibitory effects on the rep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/38A61K31/675A61K9/08A61K9/14A61K9/16A61K9/20A61K9/48A61P31/12A61P31/20
Inventor 张爱明张喜全徐宏江杨玲
Owner LIANYUNGANG RUNZHONG PHARMA CO LTD
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