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Nucleosides with anti-hepatitis B virus activity

A hepatitis B virus and nucleotide technology, applied in antiviral agents, organic active ingredients, medical preparations containing active ingredients, etc., can solve the problems that are not very effective, and nucleotides cannot effectively pass through the cell membrane

Inactive Publication Date: 2002-01-02
CENT NAT DE LA RECHERCHE SCI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually nucleotides do not cross cell membranes efficiently and are generally not very efficient in vitro

Method used

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  • Nucleosides with anti-hepatitis B virus activity
  • Nucleosides with anti-hepatitis B virus activity
  • Nucleosides with anti-hepatitis B virus activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The preparation of embodiment 1β-L-(3'-azido)-2',3'-dideoxy-5-fluorocytosine

[0060] Melting points were determined in open capillary tubes with a Gallenkamp MFB-595-010 M instrument and were uncorrected. UV absorption spectrum was measured in ethanol with Uvikon931 (KONTRON) spectrophotometer. 1 H-NMR at room temperature in DMSO-d 6 Measured with Bruker AC 250 or 400. Chemical shifts are expressed in ppm, DMSO-d 6 Set at 2.49ppm as a reference. Perform deuterium exchange, decoupling experiments or 2D-COSY to confirm the arrangement of hydrogen nuclei, and the multiplicity of signals is represented by s (singlet), d (doublet), dd (doublet doublet), t (triplet), q (quartet), br (broad), m (multiplet), and all J values ​​are expressed in Hz. FAB mass spectra were recorded with a JEOL DX300 mass spectrometer in positive (FAB>0) or negative (FAB-1 deg cm 2 g -1 express. Elemental analyzes were performed according to the "Service de Microanalyses du CNRS, Division d...

Embodiment 4

[0110] Example 4 The effects of anti-HBV β-L-deoxycytidine analogs on cell growth were evaluated by bone marrow clonal origin assay.

[0111] Table 2 shows the effect of anti-HBV β-L-deoxycytidine analogues on cell growth evaluated by bone marrow clonogenicity assay.

[0112] compound

CFU-GM

EC 50

BFU-E

EC 50 (μM)

L-2'-Azido-5-FddC

＞10

＞10

L-3'-Azido-5-FddC

10

10

L-5-FddC

1.2

1.8

Lavmidine (3TC)

＞10

＞10

D-ddC (control)

0.7

0.05

Zidovudine (AZT) (control)

1.9

0.6

[0113] The compounds disclosed herein and their pharmaceutically acceptable salts, prodrugs and derivatives are effectively used for the prevention and treatment of HBV infection and other related diseases, such as anti-HBV antibody positive and HBV positive diseases, chronic hepatitis caused by HBV, liver Cirrhosis, acute hepatitis, ful...

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PUM

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Abstract

Compounds and pharmaceutical compositions active against hepatitis B virus are provided, as is a method for the treatment of hepatitis B virus infection in humans and other host animals is provided comprising administering an effective amount of a beta -L-(2' or 3'- azido)-2',3'-dideoxy-5-fluorocytosine of formula (I) wherein R is H, acyl, monophosphate, diphosphate, or triphosphate, or a stabilized phosphate derivative (to form a stabilized nucleotide prodrug), and R' is H, acyl, or alkyl.

Description

[0001] The present invention relates to a method for treating hepatitis B virus (also known as "HBV") comprising administering an effective amount of one or more β-L-(2' or 3'-azido)-2', 3' - Dideoxy-5-fluorocytosine is administered to a host in need of treatment. background of the invention [0002] HBV is second only to tobacco as a cause of cancer in humans. Although it is assumed that it may directly cause tumor development or indirectly through chronic inflammation, liver cirrhosis, and infection-related cell regeneration, the mechanism by which HBV induces cancer is still unclear. clearly. [0003] The hepatitis B virus has reached epidemic proportions worldwide. After an incubation period of 2-6 months (at which time the host is unaware of infection), HBV infection can lead to acute hepatitis and liver damage, which causes abdominal pain, jaundice, and elevated levels of certain enzymes in the blood. HBV can cause fulminant hepatitis, a rapidly progressive and often f...

Claims

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Application Information

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IPC IPC(8): A61K31/7042A61K31/7052A61K31/7064A61K31/7068A61K31/7072A61P31/20C07H19/06C07H19/10
CPCC07H19/10C07H19/06A61P1/16A61P31/12A61P31/20A61K31/7068
Inventor 吉勒·戈瑟兰让-路易斯·因巴赫让-皮埃尔·索马多西雷蒙德·F·斯基纳齐
Owner CENT NAT DE LA RECHERCHE SCI