Development of a Multi Kilogram-Scale, Tandem Cyclopropanation Ring-Expansion Reaction en Route to Hedgehog Antagonist IPI-926

Author:

Austad Brian C.1,Hague Andrew B.1,White Priscilla1,Peluso Stéphane1,Nair Somarajan J.1,Depew Kristopher M.1,Grogan Michael J.1,Charette André B.2,Yu Lin-Chen1,Lory Caroline D.1,Grenier Louis1,Lescarbeau André1,Lane Benjamin S.1,Lombardy Richard3,Behnke Mark L.1,Koney Nii1,Porter James R.1,Campbell Matthew J.1,Shaffer Jeanne1,Xiong Jimin1,Helble Joseph C.1,Foley Michael A.1,Adams Julian1,Castro Alfredo C.1,Tremblay Martin R.1

Affiliation:

1. Infinity Pharmaceuticals, Inc., 784 Memorial Drive, Cambridge, Massachusetts 02139, United States

2. Department of Chemistry, University of Montreal, Roger Gaudry Building, D-644, Faculty of Arts and Sciences, 2900 Edouard Montpetit Blvd, Montreal, P.O. Box 6128, Station Downtown, QC H3C 3J7, Canada

3. Johnson Matthey Pharma Services, 25 Patton Rd, Devens, Massachusetts 01434, United States

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry

Reference32 articles.

1. Xie, J.Hedgehog signaling activation in human cancer and its clinical application;Springer Science + Business Multimedia LLC:New York, 2011; p217.

2. Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened

3. Discovery of a Potent and Orally Active Hedgehog Pathway Antagonist (IPI-926)

4. Austad, B.; Behnke, M. L.; Castro, A. C.; Grogan, M. J.; Janardanannair, S.; Lescarbeau, A.; Peluso, S.; Tremblay, M.Cyclopamine Analogs. US 7,812,164, October 10, 2010.

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