Metabolites of cyclosporin analogs

Details Metabolites of cyclosporin analogs Metabolites of cyclosporin analogs

C - Chemistry, Metallurgy

07

K

C07K 7/64 (2006.01) A61K 38/13 (2006.01) C12P 21/04 (2006.01)

Patent

CA 2592343

Isolated metabolites of the cyclosporine analog ISA247 are disclosed, including in vitromethods for their preparation. The metabolites comprise a chemical modification of ISA247, wherein the modification is at least one reaction selected from the group consisting of hydroxylation, N-demethylation, diol formation, epoxide formation, and intramolecular cyclization phosphorylation, sulfation, glucuronide formation and glycosylation. Methods of preparation include semi-synthetic methods, wherein metabolites of ISA247 are produced from the microsomal extracts of animal liver cells, or.from cultures using microorganisms, and completely synthetic methods, such as chemically modifying the parent compound or isolated metabolites using organic synthetic methods.

L'invention concerne des métabolites isolés de l'analogue de la cyclosporine ISA247, ainsi que des méthodes in vitro destinées à leur préparation. Ces métabolites renferment une modification chimique de ISA247, ladite modification constituant au moins une réaction sélectionnée parmi le groupe comprenant l'hydroxylation, la N-déméthylation, la formation de diol, la formation d'époxyde et la phosphorylation de cyclisation intramoléculaire, la sulfatation, la formation de glucuronide et la glycosylation. Selon l'invention, des méthodes de préparation comprennent des méthodes semi-synthétiques, au cours desquelles des métabolites de ISA247 sont produits à partir d'extraits microsomiques de cellules hépatiques animales ou de cultures utilisant des micro-organismes et, également, des méthodes entièrement synthétiques, telles que celles de modification chimique du composé parent ou des métabolites isolés à l'aide de méthodes synthétiques organiques.

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