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(12) United States Patent (10) Patent No.: US 8,883,832 B2 Shallwitz Et Al USOO8883832B2 (12) United States Patent (10) Patent No.: US 8,883,832 B2 Shallwitz et al. (45) Date of Patent: *Nov. 11, 2014 (54) COMPOUNDS, COMPOSITIONS, AND (2013.01); C07D 277/60 (2013.01); A61 K METHODS FOR PREVENTING METASTASS 31/538 (2013.01); A61K 31/428 (2013.01); OF CANCER CELLS A61K 45/06 (2013.01); A61 K3I/7068 (2013.01) (71) Applicant: Aerpio Therapeutics Inc., Cincinnati, USPC ....................... 514/365: 514/254.02: 514/342 OH (US) (58) Field of Classification Search (72) Inventors: Robert Shalwitz, Bexley, OH (US); None Kevin Gene Peters, Cincinnati, OH See application file for complete search history. (US) (56) References Cited (73) Assignee: Aerpio Therapeutics Inc., Cincinnati, OH (US) U.S. PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this 4,673,641 A 6/1987 George et al. 5,424,398 A 6/1995 Middeldorp et al. patent is extended or adjusted under 35 5,585,089 A 12/1996 Queen et al. U.S.C. 154(b) by 0 days. 5,688,781 A 1 1/1997 Siegallet al. 5,807,819 A 9/1998 Cheng et al. This patent is Subject to a terminal dis 5,994,128 A 11/1999 Fallaux et al. claimer. 6,033,908 A 3/2000 Bout et al. 6,342,219 B1 1/2002 Thorpe et al. (21) Appl. No.: 13/783,311 6,589,758 B1 7, 2003 Zhu 6,596,772 B1 7/2003 Huang et al. (22) Filed: Mar. 3, 2013 7,226,755 B1 6/2007 Peters et al. 7,507,568 B2 3/2009 Evdokimov 7,588,924 B2 9, 2009 Evdokimov et al. (65) Prior Publication Data 7,589,212 B2 9/2009 Gray et al. US 2014/0249100A1 Sep. 4, 2014 7,622,593 B2 11/2009 Gray et al. 7,795,444 B2 9/2010 Gray et al. 8, 106,078 B2 1/2012 Gray et al. Related U.S. Application Data 8,188,125 B2 5/2012 Gray et al. 8,258,311 B2 9/2012 Gray et al. (63) Continuation of application No. 12/677.550, filed as 8.329,916 B2 12/2012 Amarasinghe et al. application No. PCT/US2010/020822 on Jan. 12, 8.338,615 B2 12/2012 Gray et al. 2010, now Pat. No. 8,569,348. 2004O1671.83 A1 8/2004 Klopfenstein et al. 2004/0204863 A1 10/2004 Kim et al. (60) Provisional application No. 61/223.260, filed on Jul. 6, 2007/02991 16 A1 12/2007 Gray 2009. 2008.0004267 A1 1/2008 Gray 2008/0076764 A1 3/2008 Peters et al. 2008. O1086.31 A1 5/2008 Gray et al. (51) Int. Cl. 2009/0227639 A1 9/2009 Gray et al. AOIN 43/78 (2006.01) A6 IK3I/425 (2006.01) (Continued) A6 IK3I/427 (2006.01) A6 IK3I/53 (2006.01) FOREIGN PATENT DOCUMENTS CO7D 417/04 (2006.01) WO WOOOf 65085 11, 2000 C07D 277/64 (2006.01) WO WOOOf 65088 A1 11, 2000 CO7D 417/4 (2006.01) WO WOO2,26774 A1 4/2002 C07D 277/28 (2006.01) C07D 417/12 (2006.01) OTHER PUBLICATIONS A 6LX3L/2197 (2006.01) A6 IK3I/4245 (2006.01) Altschulet al., “Gapped BLAST and PSI-BLAST: A New Generation A6 IK3I/433 (2006.01) of Protein Database Search Programs.” Nucleic Acids Res., A6 IK3I/4439 (2006.01) 25(27).3389-3402 (1997). A6 IK3I/426 (2006.01) (Continued) C07D 277/60 (2006.01) A6 IK3I/538 (2006.01) A6 IK3I/428 (2006.01) Primary Examiner — Patrick Lewis A6 IK 45/06 (2006.01) (74) Attorney, Agent, or Firm — Richard S. Echler A6 IK3I/7068 (2006.01) (52) U.S. Cl. CPC ............ C07D 277/28 (2013.01); A61K3I/427 (57) ABSTRACT (2013.01); A61 K3I/513 (2013.01); C07D Disclosed are methods for preventing metastasis of cancer 417/04 (2013.01); C07D 277/64 (2013.01); cells. The disclosed compounds can be used to prevent the C07D 417/14 (2013.01); C07D 417/12 spread of tumor or other types of cancer cells. (2013.01); A61 K3I/497 (2013.01); A61 K 3 1/4245 (2013.01); A61 K31/433 (2013.01): A61 K3I/4439 (2013.01); A61 K3I/426 52 Claims, 5 Drawing Sheets US 8,883,832 B2 Page 2 (56) References Cited Itoh et al., “Purification and Characterization of the Catalytic Domains of the Human Receptor-Linked Protein Tyrosine U.S. PATENT DOCUMENTS Phosphatases HPTPB, Leukocyte Common Antigen (LCA), and Leukocyte Common Antigen-Related Molecule (LAR),” Journal of 2010, OO16336 A1 1/2010 Gray et al. 2011/0268694 A1 11/2011 Shallwitz et al. Biological Chemistry, 267(17): 12356-12363 (1992). 2012/O128625 A1 5, 2012 Shallwitz et al. 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