(12) United States Patent (10) Patent No.: US 9,376.418 B2 Haidle Et Al
USOO9376418B2 (12) United States Patent (10) Patent No.: US 9,376.418 B2 Haidle et al. (45) Date of Patent: Jun. 28, 2016 (54) SUBSTITUTED PYRIDINE SPLEEN 31/5377 (2013.01); A61K3I/5383 (2013.01); TYROSINE KINASE (SYK) INHIBITORS A61 K3I/551 (2013.01); A61K 45/06 (2013.01); C07D401/14 (2013.01); C07D (71) Applicants: Merck Sharp & Dohme Corp., 405/14 (2013.01); C07D 409/14 (2013.01); Rahway, NJ (US); Merck Canada Inc., C07D 413/14 (2013.01); C07D 417/14 Kirkland, Quebec (CA) (2013.01); C07D 471/04 (2013.01); (Continued) Inventors: (72) Andrew M. Haidle, Cambridge, MA (58) Field of Classification Search (US); Sandra Lee Knowles, Princeton, CPC ............... CO7D 401/12: CO7D 401/14: A61 K NJ (US); Solomon D. Kattar, Arlington, 31/5377; A61K31/506 MA (US); Denis Deschenes, Lachine USPC ........................ 544/122, 331; 514/235.8, 275 (CA); Jason Burch, Redwood City, CA See application file for complete search history. (US); Joel Robichaud, Dollard-des-Ormeaux (CA); Matthew (56) References Cited Christopher, Brookline, MA (US); Michael D. Altman, Needham, MA U.S. PATENT DOCUMENTS (US); James P. Jewell, Newtown, MA 5,710,129 A 1/1998 Lynch et al. (US); Alan B. Northrup, Reading, VA 6/2001 Uckun et al. (US); Marc Blouin, Saint-Lazare (CA); 6,248,790 B1 John Michael Ellis, Needham, MA (Continued) (US); Hua Zhou, Acton, MA (US); Christian Fischer, Natick, MA (US); FOREIGN PATENT DOCUMENTS Adam J. Schell, Decatur, GA (US); EP 877O2O A1 11, 1998 Michael H. Reutershan, Brookline, MA EP 2441755 A1 4/2012 (US); Brandon M.
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