Bicyclic nucleosides and nucleotides as therapeutic agents

a technology of bicyclic nucleosides and nucleotides, which is applied in the direction of biocide, plant growth regulators, sugar derivatives, etc., can solve the problems of mutagenic damage to the viral genome, limited disclosure of bicyclic nucleosides, and major threat to human health from viral infections

Inactive Publication Date: 2010-11-18
BIOTA SCI MANAGEMENT PTI LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Viral infections are a major threat to human health and account for many serious infectious diseases.
Furthermore, a deteriorating nucleoside analog also may be incorporated into the extending RNA, which may cause mutagenic damage to the viral genome.
Fungal infections are another type of infectious diseases, some of which also can be life-threatening.
Disclosures of bicyclic nucleosides are very limited considering that natural adenine and guanine (purines) based ribonucleotides and deoxy derivatives thereof, have bicyclic base moieties.

Method used

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  • Bicyclic nucleosides and nucleotides as therapeutic agents
  • Bicyclic nucleosides and nucleotides as therapeutic agents
  • Bicyclic nucleosides and nucleotides as therapeutic agents

Examples

Experimental program
Comparison scheme
Effect test

examples

Synthesis

[0232]

TABLE 1ExampleStructureMolec FormulaMWt1C13H15N3O6309.282C13H14IN3O6435.173C13H14BrN3O6388.174C13H14ClN3O6343.725C13H15N3O6309.286C14H17N3O6323.307C20H21N3O6399.408C16H21N3O6351.369C14H19N3O6325.3210C20H23N3O6401.4211C17H24N4O5364.4012C17H24N4O6380.4013C18H26N4O5378.4314C17H25N5O5379.4115C13H18N3O15P3549.21

Experimental Data

[0233]1H and 31P NMR spectra were recorded on either a Bruker Avance DRX 400, AC 200 or AM 300 spectrometer. Spectra were recorded in CDCl3, d6-acetone, CD3OD or d6-DMSO using the residual solvent peak as a reference. Chemical shifts are reported on the δ scale in parts per million (ppm) using the following conventions to assign the multiplicity: s (singlet), d (doublet), t (triplet), q (quartet) m (multiplet) and prefixed b (broad). Mass spectra (ESI) were recorded on a Finnigan LCQ Advantage spectrometer. All microwave reactions were carried out in a CEM Discover microwave reactor. Flash and radial chromatography was performed on 40-63 μm silica...

preparation of examples 1-4

[0241] Preparation of Example 1 is an example of the general method.

example 1

[0242] Intermediate B (60 mg) was suspended in dry methanol (1 mL) under argon. A freshly prepared solution of 1M sodium methoxide in methanol (0.5 mL) was added and the reaction stirred for 18 hrs. Evaporation of the solvent in-vacuo with minimal heating and purification by radial chromatography on silica eluting with 20% MeOH / DCM yielded the required compound as a crystalline solid.

[0243] MS m / z ([M+H]+) 309.9. 1H 1H NMR (CD3OD+D2O) δ 9.24 (s, 1H), 7.61 (d, 1H), 6.23 (d, 1H), 6.11 (s, 1H), 4.08-4.00 (m, 2H), 3.93-3.83 (m, 2H), 1.12 (s, 3H).

[0244] Similarly for Examples 2 and 3.

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Abstract

The invention relates to the use of bicyclic nucleosides and nucleotides based on formula (II) for the treatment of infectious diseases, and in particular, viral infections.

Description

FIELD OF THE INVENTION [0001] The present invention relates to the use of bicyclic nucleosides and nucleotides for the treatment of infectious diseases, including viral infections, novel bicyclic nucleosides and nucleotides and methods for their manufacture. BACKGROUND OF THE INVENTION [0002] Viral infections are a major threat to human health and account for many serious infectious diseases. The most notable viruses are the blood-borne viruses (BBV), which include hepatitis C virus (HCV), hepatitis B virus (HBV) and human immunodeficiency virus (HIV) which are all linked by their mode of transmission, i.e., through blood or bodily fluids. [0003] The Flaviviridae is a group of positive single-stranded RNA viruses with a genome size from 9-15 kb. The Flaviviridae consists of various genera including: [0004] 1. Flaviviruses: This genus includes the Dengue virus, Japanese Tick-Borne and the Yellow Fever virus. Apart from these major groups, there are some additional Flaviviruses that a...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/7068C07H19/23A61P31/14A61K38/21
CPCA61K31/706C07H19/23C07H19/22A61P31/04A61P31/06A61P31/14
Inventor FRANCOM, PAULANEARN, ROLANDDRAFFAN, ALISTAIRLAMBERT, JOHNBOND, SILAS
Owner BIOTA SCI MANAGEMENT PTI LTD
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