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1. WO1996007646 - ANTIVIRAL NUCLEOSIDE ANALOGUES CONTAINING A SUBSTITUTED BENZIMIDAZOLE BASE ATTACHED TO A CARBOCYCLIC RING

Publication Number WO/1996/007646
Publication Date 14.03.1996
International Application No. PCT/US1995/011366
International Filing Date 11.09.1995
Chapter 2 Demand Filed 05.04.1996
IPC
C07D 235/30 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
235Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
02condensed with carbocyclic rings or ring systems
04Benzimidazoles; Hydrogenated benzimidazoles
24with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
30Nitrogen atoms not forming part of a nitro radical
C07D 403/04 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
403Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/167
02containing two hetero rings
04directly linked by a ring-member-to-ring- member bond
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
A61P 31/22
AHUMAN NECESSITIES
61MEDICAL OR VETERINARY SCIENCE; HYGIENE
PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
31Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
12Antivirals
20for DNA viruses
22for herpes viruses
C07D 235/30
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
235Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
02condensed with carbocyclic rings or ring systems
04Benzimidazoles; Hydrogenated benzimidazoles
24with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
30Nitrogen atoms not forming part of a nitro radical
C07D 403/04
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
403Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
02containing two hetero rings
04directly linked by a ring-member-to-ring-member bond
Applicants
  • THE WELLCOME FOUNDATION LIMITED [GB]/[GB] (AllExceptUS)
  • THE REGENTS OF THE UNIVERSITY OF MICHIGAN [US]/[US] (AllExceptUS)
  • TOWNSEND, Leroy, B. [US]/[US] (UsOnly)
  • DALUGE, Susan, Mary [US]/[US] (UsOnly)
Inventors
  • TOWNSEND, Leroy, B.
  • DALUGE, Susan, Mary
Agents
  • CRAWFORD, Arthur, R.
Priority Data
304,00609.09.1994US
Publication Language English (EN)
Filing Language English (EN)
Designated States
Title
(EN) ANTIVIRAL NUCLEOSIDE ANALOGUES CONTAINING A SUBSTITUTED BENZIMIDAZOLE BASE ATTACHED TO A CARBOCYCLIC RING
(FR) ANALOGUES DE NUCLEOSIDES ANTIVIRAUX CONTENANT UNE BASE BENZIMIDAZOLE SUBSTITUEE FIXEE A UNE CHAINE CARBOCYCLIQUE
Abstract
(EN)
Antiviral nucleoside analogues contain a substituted benzimidazole base attached to a carbocyclic ring in place of the conventional sugar residue. In formulae (I) and (I-1), R1 is H, CH3 or CH2OH; R2 is H or OH; R3 is H or OH; or R2 and R3 together form a bond; R4 is amino, cyclopropylamino, cyclobutylamino, isopropylamino, $i(tert)-butylamino or -NR8R9 where R8 and R9 together with the nitrogen atom to which they are attached form a 4, 5 or 6-membered heterocyclic ring; R5 is H and R6 and R7 are Cl, excluding the compound (±)-(1R*, 2S*, 3S*, 5S*)-5-[5,6-Dichloro-2-(cyclopropylamino)-1H-benzimidazol-1-yl]-3-(hydroxymethyl)-1,2-cyclopentanediol and provided that at least one of R1, R2 and R3 is or contains OH. The compounds have activity against herpes virus especially cytomegalovirus and also hepatitis B virus infections.
(FR)
Cette invention se rapporte à des analogues de nucléosides antiviraux, qui contiennent une base benzimidazole substituée fixée à une chaîne carbocyclique à la place du résidu de sucre habituel. Ces composés sont représentés par les formules (I) et (I-1), où R1 représente H, CH3 ou CH2OH; R2 représente H ou OH; R3 représente H ou OH; ou R2 et R3 forment ensemble une liaison; R4 représente amino, cyclopropylamino, cyclobutylamino, isopropylamino, $i(tert)-butylamino ou -NR8R9, où R8 et R9 forment, avec l'atome d'azote auquel ils sont liés, une chaîne hétérocyclique à 4, 5 ou 6 éléments; R5 représente H; et R6 et R7 représentent Cl, à l'exclusion du composé (±)-(1R*, 2S*, 3S*, 5S*)-5-[5,6-Dichloro-2-(cyclopropylamino)-1H-benzimidazol-1-yl]-3-(hydroxyméthyl)-1,2-cyclopentanediol, et à condition qu'au moins l'un des éléments R1, R2 et R3 représente ou contienne OH. Ces composés ont une action contre les infections par le virus de l'herpès, en particulier le cytomégalovirus, et également contre les infections par le virus de l'hépatite B.
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