Dispiro 1,2,4-trioxolane antimalarials

Details Dispiro 1,2,4-trioxolane antimalarials Dispiro 1,2,4-trioxolane antimalarials

C - Chemistry, Metallurgy

07

D

C07D 493/10 (2006.01) A61K 31/343 (2006.01) A61K 31/4525 (2006.01) A61K 31/496 (2006.01) A61K 31/5377 (2006.01) A61K 31/541 (2006.01) A61K 31/553 (2006.01) A61P 33/06 (2006.01)

Patent

CA 2702256

A means and method for treating malaria, schistosomiasis, and cancer using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites. The compounds of the invention unexpectedly provide a single-dose cure for malaria, as well as prophylactic activity against the same. The compounds are also active against schistosomiasis and cancer.

L'invention concerne un moyen et un procédé de traitement du paludisme, de la schistosomiase et du cancer qui utilise un spiro- ou dispiro-1,2,4-trioxolane. Les 1,2,4-trioxolanes préférés comprennent un groupe spiroadamantane d'un côté du groupe trioxolane et un spirocyclohexyle de l'autre côté du groupe trioxolane. En comparaison des dérivés semi-synthétiques d'artémisinine, les composés selon l'invention sont structuralement simples, faciles à synthétiser, non toxiques et puissants contre les parasites paludéens. De manière surprenante, les composés selon l'invention constituent un traitement en une seule dose du paludisme, et ont également une activité prophylactique envers le paludisme. Les composés sont également actifs contre la schistosomiase et le cancer.

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