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(12) United States Patent (10) Patent No.: US 9,096,585 B2 Shaw Et Al US009096585B2 (12) United States Patent (10) Patent No.: US 9,096,585 B2 Shaw et al. (45) Date of Patent: Aug. 4, 2015 (54) ANTIVIRAL COMPOUNDS AND USES (2013.01); C07D 413/10 (2013.01); C07D THEREOF 413/12 (2013.01); A61 K 3 1/5377 (2013.01); A61 K3I/55 (2013.01) (75) Inventors: Megan Shaw, New York, NY (US); (58) Field of Classification Search Hans-Heinrich Hoffmann, New York, CPC. A61K 31/4245; A61K31/5377; A61K31/55 NY (US); Adolfo Garcia-Sastre, New USPC .................................... 514/364, 217.1, 236.2 York, NY (US); Peter Palese, Leonia, NJ See application file for complete search history. US (US) (56) References Cited (73) Assignee: Icahn School of Medicine at Mount Sinai, New York, NY (US) U.S. PATENT DOCUMENTS 6,384,064 B2 5, 2002 Camden (*) Notice: Subject to any disclaimer, the term of this 8,278,342 B2 10/2012 Ricciardi patent is extended or adjusted under 35 Continued U.S.C. 154(b) by 210 days. (Continued) (21) Appl. No.: 13? 700,049 FOREIGN PATENT DOCUMENTS y x- - - 9 (22) PCT Filed1C Mavay 31,51, 2011 WO WO 2009,136979 A2 11/2009 OTHER PUBLICATIONS (86). PCT No.: PCT/US2011/038515 Chu et al. "Analysis of the endocytic pathway mediating the infec S371 (c)(1), tious entry of mosquito-borne flavivirus West Nile into Aedes (2), (4) Date: Feb. 14, 2013 albopictus mosquito (C6/36) cells.” Virology, 2006, vol. 349, pp. 463-475. (87) PCT Pub. No.: WO2011/150413 (Continued) PCT Pub. Date: Dec. 1, 2011 Primary Examiner — Shengjun Wang (65) Prior Publication Data (74) Attorney, Agent, or Firm — Jones Day US 2013/O137678A1 May 30, 2013 (57) ABSTRACT O O Described herein are Compounds, compositions comprising Related U.S. Application Data Such Compounds, and the use of Such Compounds and com (60) Provisional application No. 61/349,606, filed on May positions as anti-viral agents. In one aspect, provided herein 28, 2010. are methods of inhibiting viral replication using Compounds s described herein or compositions thereof. In another aspect, (51) Int. Cl. provided herein are methods for preventing a symptom of a A6 IK3I/4I (2006.01) viral infection using a Compound, or a composition thereof. A6 IK3I/55 (2006.01) In another aspect, provided herein are methods of treating and/or managing viral infection using a compound or a com (Continued)Continued position thereof. (52) U.S. Cl. CPC .......... C07D 413/14 (2013.01); A61 K3I/4245 6 Claims, 26 Drawing Sheets 1 - DS A3-2 A-2 A3-2 A3-2 (0.64LM) (1.6M) (4LM) (10uM) US 9,096.585 B2 Page 2 (51) Int. Cl. Kleyman et al., 1988, “Amiloride and its analogs as tools in the study A 6LX3/535 (2006.01) of ion transport”. J. Membrane Biol; 105:1-21. Kunzelmann et al., 2000, "Influenza virus inhibits amiloride-sensi CO7D 413/4 (2006.01) tive Na" channels in respiratory epithelia'. Proc Natl AcadSci USA; A6 IK3I/4245 (2006.01) 97(18): 10282-10287. CO7D 43/10 (2006.01) Kurokawa et al., 1990, "Inhibitory effect of protein kinase Cinhibitor CO7D 413/2 (2006.01) on the replication of influenza type A virus', J Gen Virol; 71(Pt 9):2149-2155. A61 K3I/55 (2006.01) Lee et al., 2007, "Crystal structure of the VP4 protease from infec A61 K3I/5377 (2006.01) tious pancreatic necrosis virus reveals the acyl-enzyme complex for an intermolecular self-cleavage reaction', J Biol Chem; (56) References Cited 282(34):24928-24937. Link et al., 1966, "Interaction of heart glycosides and viruses'. Acta U.S. PATENT DOCUMENTS Virol; 10:455-461. 2005/O123902 A1 6, 2005 Meneses et al. Mahmoudian et al., 2009, “Influenza A virus proteins PB1 and NS1 2005/023.9906 A1 10/2005 Garaci et al. are subject to functionally important phosphorylation by protein 2009,0162831 A1 6, 2009 Delwart et al. kinase C, J Gen Virol; 90(Pt6): 1392-1397. 2010.0035887 A1 2/2010 Ricciardi Nagai et al., 1972, "Inhibition of virus growth by ouabain: effect of 2011/O105423 A1 5, 2011 Shaw ouabain on the growth of HVJ in chick embryo cells”. J. Virol; 9(2): 234-243. OTHER PUBLICATIONS Patterson et al., 1979, “Studies on the mechanism of influenza virus entry into cells”, J Gen Virol; 43(223-229). Somvanshi et al. “Comparative proteome analysis of distinct variants Rigautet al., 1991, “Inhibition of VSV infection by staurosporine'. J of Dengue virus using in silico approach.” Internet Journal of Cell Biol; 115(3Part2):476A. Genomics and proteomics, 2009, vol. 4, No. 1. URL: http://www. Rootet al., 2000, “Entry of influenza viruses into cells is inhibited by ispub.com/journal/the internet journal of genomics and proteomics. a highly specific protein kinase C inhibitor'. J Gen Virol; 81 (Pt Chen et al., 2004, “Influenza A virus PB1-F2 gene in recent Taiwan 10:2697-2705. ese isolates'. Emerging Infectious Diseases; 10(4): 630-635. Salvatore et al., 2007, "O-defensin inhibits influenza virus replication Fabbri et al., 1994, “Export of protein from the endoplasmic by cell-mediated mechanism(s)”, JID; 196:835-843. reticulum is regulated by a diacylglycerol/phorbol ester binding pro Scholtissek et al., 1986, "Influence of insulin and 12-O- tein', J Biol Chem; 269(43):26848-26857. tetradecanoylphorbol-13-acetate (TPA) on influenza virus multipli Gschwendt et al., 1994, "Rottlerin, a novel protein kinase inhibitor'. cation, Virus Res; 6:287-294. Biochem Biophys Res Commun; 199(1):93-98. Shaw et al., 2008, “Opposing effects on influenza growth by com Guggino et al., 2000, "Amiloride-sensitive sodium channels contrib pounds targeting both sodium channels and protein kinase C". Dept. ute to the woes of the flu'. Proc Natl Acad Sci USA, 97(18):9827 of Microbiology, Mount Sinai School of Medicine, New York, NY 98.29. 10029 (Abstract only). Hoffmann et al., 2008, “Modulation of influenza virus replication by Sieczkarski et al., 2003, “Role of protein kinase C BII in influenza alteration of sodium ion transport and protein kinase C activity'. virus entry via late endosomes”, JVirol; 77(1):460-469. Dept.of Microbiology, Mount Sinai School of Medicine, New York, Wright et al., 2009, "Inhibition of simian virus 40 replication by NY 10O29. targeting the molecular chaperone function and ATPase activity of T Hoffmann et al., 2008, “Modulation of influenza virus replication antigen'. Virus Res; 141(1):71-80. identified via a high-throughput screening approach'. Dept.of Written Opinion of International application No. PCT/US2009/ Microbiology, Mount Sinai School of Medicine, New York, NY 00.1474, dated Jan. 18, 2010. 10O29. Written Opinion of International application No. PCT/US2011/ International Search Report of International application No. PCT/ 38515, dated Sep. 13, 2011. US2009/00 1474, dated Jan. 18, 2010. Yiet al., 2008, “A secondary gate as a mechanism for inhibition of the International Search Report of International application No. PCT/ M2 proton channel by amantadine'. J. Phys Chem; 1 12(27):7977 US2011/38515, dated Sep. 13, 2011. 7979. Kistner et al., 1989, “Differential phosphorylation of the nucleoprotein of influenza A viruses”. J Gen Virol; 70:2421-2431. * cited by examiner U.S. Patent Aug. 4, 2015 Sheet 2 of 26 US 9,096,585 B2 s t Tufnd Jege, U.S. Patent Aug. 4, 2015 Sheet 3 of 26 US 9,096,585 B2 ?CA %89- %89- %176- ungdoo Jaeli U.S. Patent US 9,096,585 B2 s H und Oilsea U.S. Patent Aug. 4, 2015 Sheet 5 of 26 US 9,096,585 B2 s s s s s s s S s l r suggestueued eyes U. S. Patent She et 6 of 26 U S9,9,096.58 5 B2 s li Are Juiced RA e U.S. Patent Aug. 4, 2015 Sheet 7 of 26 US 9,096,585 B2 CO o s d & an A N o b rf C f s Z as V H CS 3 II. I. N O O C i > > jungdu Jaye U.S. Patent Aug. 4, 2015 Sheet 8 of 26 US 9,096,585 B2 a. D f 9. O d d a L Od A. s S. i (u/nyd) Jell. Snu1W U.S. Patent Aug. 4, 2015 Sheet 9 of 26 US 9,096,585 B2 T=IOWN- 'H s (d-J9)e?oseT/ACJN T=IOWN- U.S. Patent Aug. 4, 2015 Sheet 10 of 26 US 9,096,585 B2 . 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