Vinblastine 20″ amides: synthetic analogs that maintain or improve potency and simultaneously overcome Pgp-derived efflux and resistance
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United States of America Patent
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Jun 23, 2020
Grant Date -
Apr 25, 2019
app pub date -
Aug 1, 2018
filing date -
Sep 15, 2017
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Abstract
A vinca alkaloid compound substituted at the 20′-position with a carboxamido group is disclosed. The carbonyl of the carboxamido group is bonded to a 20′-amino group and to a ring system that contains up to three 5-, 6- or 7-membered rings that are fused or otherwise bonded together. Each ring can be carbocyclic or heterocyclic, with a heterocyclic ring containing up to three hetero ring atoms that are the same or different and are selected from nitrogen, oxygen and sulfur. The ring system can include up to four substituent groups other than hydrogen that are discussed within. Methods of preparing the compounds are disclosed as are compositions for their use and methods of treatment using d compound. A particularly preferred compound has an activity in specified cancer cell growth inhibition assays that is the same or better than its parental, unsubstituted vinca compound and is not subject to Pgp-mediated efflux.
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