Method of synthesis of morpholino oligomers

Details Method of synthesis of morpholino oligomers Method of synthesis of morpholino oligomers

C - Chemistry, Metallurgy

07

D

C07D 473/18 (2006.01) A61K 31/70 (2006.01)

Patent

CA 2704261

Morpholino compounds are provided having the structure (I): where R1 is selected from the group consisting of lower alkyl, di(lower alkyl)amino, and phenyl; R2 is selected from the group consisting of lower alkyl, monocyclic arylmethyl, and monocyclic (aryloxy)methyl; R is selected from the group consisting of triarylmethyl and hydrogen; and Y is selected from the group consisting of: a protected or unprotected hydroxyl or amino group; a chlorophosphoramidate group; and a phosphorodiamidate linkage to the ring nitrogen of a further morpholino compound or a morpholino oligomer. Such compounds include doubly protected morpholino guanine (MoG) monomers. Also described is their use in synthesis of morpholino oligomers, and further improved procedures for synthesis of morpholino oligomers, pertaining to deprotection of the protected morpholino ring nitrogen at each monomer coupling step.

L'invention porte sur des composés morpholino de structure (I); dans laquelle: R1 est choisi parmi alkyle inférieur, di(alkyle inférieur)amino et phényle; R2 est choisi parmi, arylméthyle monocyclique, et (aryloxy) méthyle monocyclique; R3 est choisi parmi triarylméthyle et hydrogène; et Y est choisi parmi: un groupe hydroxyle protégé ou non protégé ou un groupe amino; un groupe chlorophosphoramidate; et une liaison phosphorodiamidate avec le cycle azote d'un autre composé morpholino ou d'un oligomère morpholino. De tels composés comprennent des monomères doublement protégés de morpholino guanine (MoG). L'invention porte également sur leur utilisation dans la synthèse d'oligomères morpholino, sur des procédures améliorées de synthèse de oligomères morpholino utilisant la déprotection de l'azote du cycle morpholino protégé à chaque étape de couplage du monomère.

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