Pyrrolo(2,3-d)pyrimidine derivatives as antivirals

Details Pyrrolo(2,3-d)pyrimidine derivatives as antivirals Pyrrolo(2,3-d)pyrimidine derivatives as antivirals

C - Chemistry, Metallurgy

07

D

C07D 487/04 (2006.01) A61K 31/505 (2006.01)

Patent

CA 2184199

This invention relates to a novel class of 4,5,6,7-substituted non-nucleoside, non-phosphorylatable pyrrolo[2,3-d]pyrimidines which exhibit both significantly lower levels of cytotoxicity and superior antiviral activity than known nucleoside, non-nucleoside, and non-nucleoside, non- phosphorylatable pyrrolo[2,3-d]pyrimidine derivatives, particularly against human DNA viruses such as cytomegalovirus (HCMV) and herpes simplex virus type 1 (HSV-1). These compounds are represented by formula (I) wherein R4 is -NH2 or -NHCH3; R5 is -CN, -CSNH2, or -CSeNH2; R6 is -H or -NH2; and R7 is selected from the group consisting of aryls and aralkyls having 6 to 30 carbon atoms; aliphatic oxy-hydrocarbyls having 2 to 15 carbon atoms, lacking free hydroxyl groups and further lacking acyl or acyl derivatized groups; and oxy- hydrocarbyls having 6 to 30 carbon atoms, at least one aryl or aralkyl group, and only one oxy-group; with the proviso that if R5 is -CN and R6 is -H, then R4 is -NH2 and R7 is -CH2C6H4-2-CH3.

L'invention concerne une nouvelle classe de pyrrolo[2,3-d]pyrimidines 4,5,6,7-substituées, non-nucléosidiques et non phosphorylatables, qui présentent à la fois des niveaux de cytotoxicité nettement inférieurs et une activité antivirale supérieure par rapport aux dérivés de pyrrolo[2,3-d]pyrimidine nucléosidiques, non nucléosidiques et non phosphorylatables connus, notamment contre les virus humains à ADN tels que le cytomégalovirus (CMVH) et l'herpès virus simplex type 1 (HVS-1). Ces composés sont représentés par la formule (I) où R?4¿ représente -NH¿2? ou -NHCH¿3?; R?5¿ représente -CN, -CSNH¿2? ou -CSeNH¿2?; R?6¿ représente -H ou -NH¿2?; et R?7¿ est choisi dans le groupe consistant en aryles et aralkyles dotés de 6 à 30 atomes de carbone, oxy-hydrocarbyles aliphatiques dotés de 2 à 15 atomes de carbone, dépourvus de groupes hydroxyle libres et d'autres groupes acyle ou dérivés d'acyle, et oxy-hydrocarbyle dotés de 6 à 30 atomes de carbone, d'au moins un groupe aryle ou aralkyle et d'un seul groupe oxy, à condition que si R?5¿ représente -CN et R?6¿ représente -H, R?4¿ représente -NH¿2?, et R?7¿ représente -CH¿2?C¿6?H¿4?-2-CH¿3?.

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