Novel bicyclonucleoside analogues

C - Chemistry – Metallurgy – 07 – H

Patent

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C07H 19/167 (2006.01) A61K 31/7125 (2006.01) A61P 31/18 (2006.01) C07H 19/06 (2006.01) C07H 19/067 (2006.01) C07H 19/16 (2006.01) C07H 21/00 (2006.01)

Patent

CA 2380205

This invention provides novel bicyclonucleoside analogues which exhibit anti-AIDS activity and intermediates to produce oligonucleotide analogues which have anti-sense or anti-gene activity as well as in vivo stability. The present invention is compounds of the following formula (1) or their pharmaceutically acceptable salts. (see formula I) R1 represents a hydrogen atom or protecting group for a hydroxy group, R2 represents an azido group or an optionally protected amino group or the like, B represents a purin-9-yl or a 2-oxo-1,2-dihydropyrimidin-1-yl group which are optionally substituted with substituents selected from .alpha. group shown below. (.alpha. group) halogen atom, alkyl group having 1-6 carbon atoms, hydroxy group, mercapto group, amino group, and the like.

La présente invention concerne, d'une part des analogues de bicyclonucléosides se caractérisant par une activité anti-SIDA, et d'autre part des intermédiaires servant à l'élaboration d'analogues d'oligonucléotides dotés d'une très bonne acitvité antisens ou antigène, tout en étant stable in vivo. L'invention concerne plus particulièrement des composés repésentés par la formule de structure (I) ou certains de leurs sels pharmacologiquement admis. En l'occurrence, R<1> est hydrogène ou un groupe protecteur hydroxyle. R<2> est azido, amine éventuellement protégé ou analogue. Enfin, B est un groupe purin-9-yle ou 2-oxo-1,2-dihydropyrimidin-1-yle éventuellement substitué par un élément appartenant au groupe constitué notamment des halogènes, C1-C6 alkyle, hydroxyle, mercapto, amine.

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