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1. WO1997027204 - MODIFIED BENZIMIDAZOLE NUCLEOSIDES AS ANTIVIRAL AGENTS

Publication Number WO/1997/027204
Publication Date 31.07.1997
International Application No. PCT/US1997/000764
International Filing Date 22.01.1997
Chapter 2 Demand Filed 19.08.1997
IPC
C07D 471/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
471Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/-C07D463/251
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
C07H 7/06 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
7Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
06Heterocyclic radicals
C07H 11/00 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
11Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
C07H 19/052 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
19Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro derivatives thereof
02sharing nitrogen
04Heterocyclic radicals containing only nitrogen as ring hetero atom
052Imidazole radicals
CPC
A61P 31/12
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
31Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
12Antivirals
C07D 471/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
471Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
02in which the condensed system contains two hetero rings
04Ortho-condensed systems
C07H 11/00
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
11Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
C07H 19/052
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
19Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides ; Anhydro-derivatives thereof
02sharing nitrogen
04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
052Imidazole radicals
C07H 7/06
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
7Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
06Heterocyclic radicals
C07H 9/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
9Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
02the hetero ring containing only oxygen as ring hetero atoms
04Cyclic acetals
Applicants
  • THE REGENTS OF THE UNIVERSITY OF MICHIGAN [US]/[US] (AllExceptUS)
  • GLAXO GROUP LIMITED [GB]/[GB] (AllExceptUS)
  • TOWNSEND, Leroy, B. [US]/[US] (UsOnly)
  • DRACH, John, C. [US]/[US] (UsOnly)
  • FREEMAN, George, A. [US]/[US] (UsOnly)
Inventors
  • TOWNSEND, Leroy, B.
  • DRACH, John, C.
  • FREEMAN, George, A.
Agents
  • KONSKI, Antoinette, F.
  • SEXTON, Jane, Helen
Priority Data
60/010,46323.01.1996US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) MODIFIED BENZIMIDAZOLE NUCLEOSIDES AS ANTIVIRAL AGENTS
(FR) NUCLEOSIDES DE BENZIMIDAZOLE MODIFIES UTILISES COMME AGENTS ANTIVIRAUX
Abstract
(EN)
This invention pertains to nucleoside analogs which have antiviral activity and improved metabolic stability. More specifically, this invention pertains to modified sugar benzimidazole nucleosides, as exemplified by compounds such as benzimidazole nucleosides possessing a fluorinated sugar-like moiety (for example, a 2'-fluoro-furanosyl moiety or a 3'-fluoro-furanosyl moiety), and may be represented by formula (I) wherein R1 is a fluorinated sugar-like moiety; and R2, R4, R5, R6 and R7 are benzimidazole substituents, such as -H, halogens (e.g., -F, -C1, -Br, -I), -NO2, -NR2 (where R is independently -H or an alkyl group having 1-6 carbon atoms), -OR (where R is -H or an alkyl group having 1-6 carbon atoms), -SR (where R is -H or a hydrocarbyl of 1-10 carbon atoms), and -CF3. In one embodiment, R1 is 2'-fluoro-furanosyl or 3'-fluoro-furanosyl; R2 is -H, -F, -C1, -Br, -I, or -NR2, wherein R is independently -H or an alkyl group having 1-6 carbon atoms; R4, R5, R6 and R7 are independently -H, -F, -C1, -Br, or -I.
(FR)
L'invention concerne des analogues de nucléosides ayant une activité antivirale et une stabilité métabolique améliorée. Plus spécifiquement, elle concerne des nucléosides de benzimidazole à sucres modifiés, tels que des nucléosides de benzimidazole possédant une fraction de type sucre fluoré (par exemple, une fraction 2'-fluoro-furanosyle ou une fraction 3'-fluoro-furanosyle), qui peuvent être représentés par la formule suivante (I), où R1 est une fraction de type sucre fluoré; et R2, R3, R4 et R5 sont des substituants benzimidazole, tels que -H, halogènes (par exemple F, Cl, Br, I), NO2, NR2 (où R est indépendamment -H ou un groupe alkyle contenant 1 à 6 atomes de carbone), -OR (où R est -H ou un groupe alkyle contenant 1 à 6 atomes de carbone), SR (où R est -H ou hydrocarbyle contenant 1 à 10 atomes de carbone) et -CF3. Dans un mode de réalisation, R1 est 2'-fluoro-furanosyle ou 3'-fluoro-furanosyle; R2 est -H, -F, -Cl, -Br, -I ou -NR2, où R est indépendamment -H ou un groupe alkyle contenant 1 à 6 atomes de carbone; R4, R5, R6 et R7 sont indépendamment -H, -F, -Cl, -Br ou -I.
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