Optimization of the in vivo activity of potent, Notch-sparing gamma secretase inhibitors

MEDI 245

Anthony Kreft, krefta@wyeth.com1, Boyd L. Harrison1, Magid Abou-Gharbia1, Jay Afragola2, Asaf Alimardinov2, Madelene Antane1, Suzan Aschmies3, Kevin Atchison3, Thomas Caggiano1, Michael Chlenov1, Derek Cole2, Thomas Comery3, George Diamantidis1, John Ellingboe2, Kristi Fan1, Cathleen Gonzalez3, Diane Hauze4, Molly Hoke, HOKEM@wyeth.com1, Yun Hu3, Xinyi Huang4, Donna Huryn1, Uday Jain1, Mei Jin3, Gulnaz Khafizova2, Dennis Kubrak1, Kristina Kutterer5, Melissa Lin2, Peimin Lu3, Joseph Lundquist4, Ronald L. Magolda1, Charles Mann1, Robert Martone3, Michael May2, Scott Mayer1, John Mehlmann4, William J. Moore6, Koi Morris1, Aram Oganesian7, Menelas Pangalos3, Alex Porte1, Peter Reinhart3, Lynn Resnick1, David R. Riddell3, Jean Schmid2, June Sonnenberg-Reines3, Joseph Stock2, Roy Sun3, Erik Wagner3, Zheng Wang1, Kevin Woller6, Zheng Xu3, Margaret M Zaleska3, Minsheng Zhang1, Hua Zhou3, and J. Steven Jacobsen3. (1) Chemical and Screening Sciences, Wyeth Research, CN 8000, Princeton, NJ 08543, (2) Chemical and Screening Sciences, Wyeth Research, Pearl River, NY, 401 N. Middletown Rd., Pearl River, NY 10965, (3) Discovery Neuroscience, Wyeth Research, Princeton, NJ, CN 8000, Princeton, NJ 08543-8000, (4) Chemical and Screening Sciences, Wyeth Research, Collegeville, PA, 500 Arcola Road, Collegeville, PA 19426, (5) Chemical & Screening Sciences, Wyeth Research, Pearl River, NY, 401 N. Middletown Rd., Pearl River, NY 10965, (6) Division of Chemical Technologies, ArQule, Inc, Woburn, MA, 19 Presidential Way, Woburn, MA 01801, (7) Drug Safety & Metabolism, Wyeth Research, Collegeville, PA, 500 Arcola Road, Collegeville, PA 19426
Alzheimer's disease (AD) is the most devastating human disease for which there is still no highly effective treatment. Currently available AD therapies only provide symptomatic treatment. The proposed causative role for Abeta40 and Abeta42 in the pathophysiology of AD has provided a rational strategy for the design of disease-modifying anti-AD drugs (DMAADs). By blocking the synthesis of these putative pathogenic peptides, it is hoped that the progression of AD will be slowed or prevented. We have focused our efforts on inhibition of gamma secretase, the final enzyme in the biosynthesis of Abeta40 and Abeta42 from APP. A caveat with this approach is that selectivity of gamma secretase inhibition of APP processing is required due to the importance of other gamma secretase substrates such as Notch in important physiological processes such as G.I. cell renewal. We have previously reported on the discovery of the Notch-sparing gamma secretase inhibitor (GSI) 5-chloro-N-[(1S)-2-ethyl-1-(hydroxymethyl)butyl]-2-thiophenesulfonamide (EC50Abeta40 and Abeta42 = 25 nM and 27 nM, respectively, EC50Notch= 246 nM) by optimization of an HTS lead. However, this compound shows limited oral activity in Tg2576 mice due to rapid in vivo metabolism. By identifying and blocking the sites of metabolism of this lead and related analogs we have designed and synthesized novel GSIs with potent, oral in vivo activity that also retain Notch-sparing selectivity. The evolution of this series of compounds will be discussed.