Rapamycin metabolites

Details Rapamycin metabolites Rapamycin metabolites

C - Chemistry, Metallurgy

07

H

C07H 19/01 (2006.01) C07D 498/18 (2006.01) C12P 17/18 (2006.01)

Patent

CA 2068349

This invention provides metabolites of rapamycin, the first of which is 41-O- desmethyl rapamycin, having a deprotonated molecular ion detected at a mass to charge ratio of 899, and a characteristic desorption chemical ionization mass spectroscopic fragmentation pattern comprising ions detected at a mass to charge ratio of 591, 569, 559, 543, 529, 421, and 308. A second compound of this invention is a hydroxylated metabolite of rapamycin having a deprotonated molecular ion detected at a mass to charge ratio of 928, and a characteristic direct chemical ionization mass spectroscopic fragmentation pattern comprising ions detected at a mass to charge ratio of 607, 571, 545, 513, 322, 290, and 241 amu. The compounds of this invention, by virtue of their immunosuppressive activity are useful in treating transplantation rejection, host vs. graft disease, autoimmune diseases and diseases of inflammation; by virtue of their antitumor activity are useful in treating solid tumors; and by virtue of their antifungal activity are useful in treating fungal infections.

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