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ID: ALA4017535

Journal: J Med Chem

Title: Discovery of N-(4-(2,4-Difluorophenoxy)-3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)phenyl)ethanesulfonamide (ABBV-075/Mivebresib), a Potent and Orally Available Bromodomain and Extraterminal Domain (BET) Family Bromodomain Inhibitor.

Authors: McDaniel KF, Wang L, Soltwedel T, Fidanze SD, Hasvold LA, Liu D, Mantei RA, Pratt JK, Sheppard GS, Bui MH, Faivre EJ, Huang X, Li L, Lin X, Wang R, Warder SE, Wilcox D, Albert DH, Magoc TJ, Rajaraman G, Park CH, Hutchins CW, Shen JJ, Edalji RP, Sun CC, Martin R, Gao W, Wong S, Fang G, Elmore SW, Shen Y, Kati WM.

Abstract: The development of bromodomain and extraterminal domain (BET) bromodomain inhibitors and their examination in clinical studies, particularly in oncology settings, has garnered substantial recent interest. An effort to generate novel BET bromodomain inhibitors with excellent potency and drug metabolism and pharmacokinetics (DMPK) properties was initiated based upon elaboration of a simple pyridone core. Efforts to develop a bidentate interaction with a critical asparagine residue resulted in the incorporation of a pyrrolopyridone core, which improved potency by 9-19-fold. Additional structure-activity relationship (SAR) efforts aimed both at increasing potency and improving pharmacokinetic properties led to the discovery of the clinical candidate 63 (ABBV-075/mivebresib), which demonstrates excellent potency in biochemical and cellular assays, advantageous exposures and half-life both in animal models and in humans, and in vivo efficacy in mouse models of cancer progression and inflammation.

CiteXplore: 28949521

DOI: 10.1021/acs.jmedchem.7b00746