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United States Patent (10) Patent No.: US 9,724,340 B2 Liang Et Al

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United States Patent (10) Patent No.: US 9,724,340 B2 Liang Et Al USOO9724340B2 (12) United States Patent (10) Patent No.: US 9,724,340 B2 Liang et al. (45) Date of Patent: Aug. 8, 2017 (54) ANTITUSSIVE COMPOSITIONS AND 5,952,339 A 9, 1999 Bencherif METHODS 5,969,144 A 10, 1999 London 6.432,975 B1 8, 2002 Schmitt 6,734,215 B2 5/2004 Shytle (71) Applicant: Attenua, Inc., New York, NY (US) 6,953,855 B2 10/2005 MaZurov et al. 7,115,629 B2 10/2006 Farrerons (72) Inventors: Jing Liang, New York, NY (US); Peter 7.425,561 B2 9/2008 MaZurov et al. Dicpinigaitis, Armonk, NY (US); 7,754,189 B2 7/2010 MaZurov et al. Brendan Canning, Baltimore, MD 7,767,193 B2 8, 2010 MaZurov et al. s 7.981906 B2 7, 2011 Dull et al. (US); Robert Devita, Westfield, NJ 8,084,462 B2 12/2011 MaZurov et al. (US) 8,119,659 B2 2/2012 Dullet al. 8,124,618 B2 2/2012 Mazurov et al. (73) Assignee: Attenua, Inc., New York, NY (US) 8,124,619 B2 2/2012 MaZurov et al. 8,143,272 B2 3/2012 MaZurov et al. (*) Notice: Subject to any disclaimer, the term of this 8,476,2968, 158,649 B2 4/20127/2013 MazurovBencherif et et al. al. patent is extended or adjusted under 35 8,541,446 B2 9/2013 Bencherif et al. U.S.C. 154(b) by 0 days. 8,541,447 B2 9/2013 MaZurov et al. 8,846,715 B2 9/2014 Bencherif et al. (21) Appl. No.: 15/208,266 8,901,151 B2 12/2014 Bencherif et al. 9,173,876 B2 11/2015 Bencherif et al. 1-1. 2005/0255.040 A1 11/2005 MaZurov (22) Filed: Jul. 12, 2016 2008.0003280 A1 1/2008 Levine 2008. O138287 A1 6/2008 MaZurov (65) Prior Publication Data 2015,0045386 A1 2/2015 Bencherif US 2017/OO27918 A1 Feb. 2, 2017 FOREIGN PATENT DOCUMENTS Related U.S. Application Data IN 17357O B 6, 1994 WO 9112254 A1 8, 1991 (60) Provisional application No. 62/199,353, filed on Jul. WO 9408992 A1 4f1994 31, 2015. WO 95.03306 A1 2, 1995 WO 96.12711 A1 5/1996 Int. C. WO 9631475 A2 10, 1996 (51) WO 964O682 A1 12, 1996 A6 IK 3/439 (2006.01) WO 970 1556 A1 1, 1997 A6 IK3I/444 (2006.01) A6 IK 45/06 (2006.01) (Continued) A61 K 9/00 (2006.01) (52) U.S. C. OTHER PUBLICATIONS CPC .......... A6 IK3I/444 (2013.01); A61K 31/439 Dicpinigaitis, P. Cough Reflex Sensitivity in Cigarette Smokers, (2013.01); A61K 45/06 (2013.01); A61 K Chest 123, 685-688, 2003. 9/0073 (2013.01) Dicpinigaitis, P. et al., Effect of Smoking Cessation on Cough (58) Field of Classification Search Reflex Sensitivity, Eur Respir J 28, 786-790, 2006. None Dicpinigaitis, P. et al., Effect of e-Cigarette Use on Cough Reflex See application file for complete search history. Sensitivity, Chest 149(1), 161-165, 2016. Papke, R. et al., The Analgesic-Like Properties of the Alpha7 References Cited nAChR Silent Agonist NS6740 is Associated with Non-Conducting (56) Conformations of the Receptor, Neuropharmacology, Apr. 1-25, U.S. PATENT DOCUMENTS 2015. Arneric, S. et al., Cholinergic Channel Modulators as a Novel 4,203,990 A 5, 1980 Yen Therapeutic Strategy for Alzheimer's Disease, Exp Opin Invest 4,922.901 A 5, 1990 Brooks Drugs 5(1), 79-100, 1996. 4,970,315 A 11/1990 Schmidhalter 5,212,188 A 5, 1993 Caldwell (Continued) 5,217,975 A 6, 1993 Wadsworth 5,219,849 A 6, 1993 Lotti 5,276,043 A 1/1994 Lippiello Primary Examiner — Jeffrey S Lundgren 5,346,906 A 9, 1994 Baker Assistant Examiner — Meghan Finn 5,510,355 A 4, 1996 Bencherif 5,583,140 A 12/1996 Bencherif (74) Attorney, Agent, or Firm — Dennis A. Bennett; 5,597,919 A 1, 1997 Dull Brock Levin 5,604.231 A 2, 1997 Smith 5,616,707 A 4/1997 Crooks 5,616,716 A 4, 1997 Dull (57) ABSTRACT 5,663,356 A 9, 1997 Ruecroft 5,712,270 A 1, 1998 Sabb Disclosed herein are compositions which include nicotinic 5,811,442 A 9, 1998 Bencherif 5,824,692 A 10/1998 Lippiello receptoragonists, specifically of the C7 nAChR Subtype, and 5,852,041 A 12/1998 Cosford methods for Suppressing cough. 5,853,696 A 12/1998 Elmaleh 5,859,004 A 1/1999 Olesen 5,861,423 A 1, 1999 Caldwell 20 Claims, 4 Drawing Sheets US 9,724,340 B2 Page 2 (56) References Cited Bencherif M. TC-5619: An alpha7 neuronal nicotinic receptor Selective agonist that ameliorates positive and negative symptoms FOREIGN PATENT DOCUMENTS and enhances cognitive function in animal models of Schizophrenia. Biochem. Phamacol, Oct. 1, 2009; 78 (7), 803-12. WO 9711072 A1 3, 1997 Heeschen, C. et al., A Novel Angiogenic Pathway Mediated by WO 973.0998 A1 8, 1997 Non-Neuronal Nicotinic Acetylcholine Receptors, J. Clin Invest WO 98.25619 A1 6, 1998 110(4), 527-536, 2002. WO 98.54181 A1 12, 1998 Holladay, M.W. et al.: Neuronal Nicotinic Acetylcholine Receptros WO 9903859 A1 1, 1999 as Targets for Drug Discovery J. Med. Chem... vol. 40, No. 26, Dec. WO 99516O2 A1 10, 1999 WO 9962.505 A2 12/1999 19, 1997 (Dec. 12, 1997), pp. 4169-4194, XP002124847 Washing WO OO34276 A1 6, 2000 tOn. WO O136417 A1 5, 2001 Hoyer, D. et al., Partial Agonists, Full Agonists, Antagonists: WO O185727 A1 11/2001 Dilemmas of Definition, TiPS Reviews 14(7), 270-275, 1993. WO 0215662 A2 2, 2002 International Search Report, PCT/US991 19906, Jan. 13, 2000. WO O216356 A2 2, 2002 Jeyarasasingam, G., et al., Stimulation of Non-a7 Nicotinic Recep WO O216357 A2 2, 2002 tors Partially Protects Dopaminergic Neurons from 1-Methyl-4 WO O216358 A2 2, 2002 WO O217358 A2 2, 2002 Phenylpyridinium-Induced Toxicity in Culture, Neuroscience WO 02051841 A1 T 2002 109(2), 275-285 (2002). WO 2004O76449 A2 9, 2004 Jonakait, G. Miller, TINS, Neural-immune interactions in sympa thetic ganglia, vol. 16, No. 10, pp. 419–423 (1993). Kaiser, S. et al., al-Bungarotoxin-Sensitive Nicotinic Receptors OTHER PUBLICATIONS Indirectly Modulate 3H Dopamine Release in Rat Striatal Slices Via Glutamate Release, Molecular Pharmacology 58, 312-318, Arneric, S. et al., Preclinical Pharmacology of ABT-418: A Proto 2000. typical Cholinergic Channel Activator for the Potential Treatment of Kalamida, et al. (FEBS Journal, 274 (2007), 3799-3845). Alzheimer's Disease, CNS Drug Rev 1(1), 1-26, 1995. Lavand’Homme, P. et al., Sex Differences in Cholinergic Analgesia Astles, PC et al., Recent Progress in the Development of Subtype Selective Nicotinic Acetylcholine Receptor Ligands, Current Drug II: Differing Mechanisms in Two Models of Allodynia, Anesthesi Targets CNS & Neurological Disorders 1(4), 337-348, 2002. ology 91 (5), 1455-1461, 1999. Bannon, AW et al., Broad-Spectrum, Non-Opioid Analgesic Activ Leonard, S. et al., Nicotinic Receptor Function in Schizophrenia, ity by Selective Modulation of Neuronal Nicotinic Acetylcholine Schizophrenia Bulletin 22(3), 431-445, 1996. Receptors, Science 279, 77-80, 1998. Levin, ED et al., AR-R17779, an a7 nicotinic agonist, improves Barnes, P. Nuclear Factor kB, Int J Biochem Cell Biol 29(6), learning and memory in rats, Behavioural Pharamacology 10(6/7), 867-870, 1997. 675-680, 1999. Bencherif, M. et al., RJR-2403: A Nicotinic Agonist with CNS Levin, ED et al., Nicotinic Treatment for Cognitive Dysfunction, Selectivity I. In Vitro Characterization, JPET 279(3), 1413-1421, Current Drug Targets—CNS and Neurological Disorders 1(4), 1996. 423-431, 2002. Birtwistle, J., The Role of Cigarettes and Nicotine in the Onset and Lippiello, P.M., et al., “RJR-2403: A Nicotinic Agonist with CNS Treatment of Ulcerative Colitis, Postgrad Med J 72, 714-718, 1996. Selectivity II. In Vivo Characterization, J. Pharmacol. Exp. Ther. CAS Printout for Begue et al., Dec. 1969. 279(3): 1422-1429 (1996). CAS Printout for IN 173 570, 54-25, Jun. 4, 1994. Macor, J. et al., The 5-HT3 Antagonist Tropisetron (ICS 205-930) CAS Printout for Schmidhalter et al., Nov. 1990. is a Potent and Selective a7 Nicotinic Receptor Partial Agonist, Chiari, A. et al., Sex Differences in Cholinergic Analgesia I: A Bioorg Med Chem Lett 11, 319-321, 2001. Supplemental Nicotinic Mechanism in Normal Females, Anesthe MadretSma, G.S., et al., Nicotine inhibits the in vitro production of siology 91 (5), 1447-1454, 1999. interleukin 2 and tumour necrosis factor-alpha, by human Damaj, MI et al., Antiniciceptive and Pharmacological Effects of monocuclear cells, Immunopharmacology, 35, pp. 47-51 (1996). Metanicotine, a Selective Nicotinic Agonist, JPET291 (1), 390-398. MadretSma, Stanley et al., In-vivo effect of nicotine on cytokine 1999. production by human non-adherent mononuclear cells, European Dolle, F. F et al., Synthesis and Preliminary Evaluation of a Journal of Gastroenterology & Hepatology, vol. 8, No. 10, pp. Carbon-11-labelled Agonist of the a-7 Nicotinic Acetylcholine 1017-1020 (1996). Receptor, J Labelled Comp Radiopharm 44, 785-795, 2001. Marrero M. Lucas R. Salet C. Hauser TA, Mazarov A. Lippiello PM, Dunlop, J., et al. In vitro screening strategies for nicotinic receptor Bencherif M. An Alpha 7Receptor-Selective Agonist Reduces ligands, Biochemical Pharmacology, 74: 1172-1181 (2007). Weight Gain and Metabolic Changes in a Mouse Model of Diabetes. Ebadi, M. et al., Neurotrophins and Their Receptors in Nerve Injury J Pharmacol Exper Ther Fast Forward Sep. 28, 2009; e-pub. and Repair, Neurochem Int30(4/5), 347-374, 1997. Matthys, Patrick PhD.
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