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(12) United States Patent (10) Patent No.: US 9,051,320 B1 Evans (45) Date of Patent: Jun

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(12) United States Patent (10) Patent No.: US 9,051,320 B1 Evans (45) Date of Patent: Jun US009051320B1 (12) United States Patent (10) Patent No.: US 9,051,320 B1 Evans (45) Date of Patent: Jun. 9, 2015 (54) METHODS FOR THE TREATMENT OF 399:S A. 23.9 Shipschultz et al.t al. METABOLIC DSORDERS BY A SELECTIVE 2011 0110886 A1 5, 2011 Braddock SMALL MOLECULE AUTOTAXN 2011/O160148 A1 6, 2011 Parrill-baker et al. INHIBITOR 2011/0230471 A1 9, 2011 Staehle et al. 2011/0237583 A1 9/2011 Schiemann et al. (71) Applicant: Pharm Akea, Inc., San Diego, CA (US) 2012fOO15959 A1 1/2012 Staehle et al. O O 2012, OO15976 A1 1/2012 Schultz et al. (72) Inventor: Jillian Frances Evans, San Diego, CA 2012/005901.6 A1 3/2012 Schiemann et al. (US) 2012/0100592 A1 4/2012 Parrill-baker et al. 2012/0115852 A1 5, 2012 Schultz et al. (73) Assignee: PHARMAKEA, INC., San Diego, CA 2012fO190650 A1 T/2012 Gupte et al. (US) 2012/0202827 A1 8/2012 Schiemann et al. 2013, OO12505 A1 1/2013 Staehle et al. (*) Notice: Subject to any disclaimer, the term of this 2013,0029948 A1 1/2013 Roppe et al. patent is extended or adjusted under 35 2013/0150326 A1* 6/2013 Roppe et al. .................... 514,64 U.S.C. 154(b) by 0 days. 2013/0251728 A1 9/2013 Harp et al. 2014/0113953 A1 4/2014 Stoffel et al. (21) Appl. No.: 14/462,459 2014/0171361 A1 6/2014 Jonker et al. 1-1. 2014/0171403 A1 6/2014 Legrand et al. (22) Filed: Aug. 18, 2014 2014/0171404 A1 6/2014 Furminger et al. (51) Int. Cl. 2014/0200231 A1 T/2014 Beauchampe h tal. A6 IK3I/405 (2006.01) FOREIGN PATENT DOCUMENTS CO7D 47L/4 (2006.01) A6 IK3I/437 (2006.01) WO WO-2008-157361 12/2008 CO7D 403/04 (2006.01) WO WO-2009-046804 4/2009 A6 IK3I/4I55 (2006.01) WO WO-2009-046841 4/2009 CO7D 40/4 (2006.01) W: W3: 39. A6 IK3I/4439 (2006.01) WO WO-2010-040080 4/2010 CO7D 403/06 (2006.01) WO WO-2010-060532 6, 2010 A6 IK3I/4025 (2006.01) WO WO-2010-063352 6, 2010 WO WO-2010-112116 10, 2010 A6 IK 45/06 (2006.01) WO WO-2010-112124 10, 2010 (52) U.S. Cl. WO WO-2010-115491 10, 2010 CPC ............ C07D 471/14 (2013.01); A61K3I/437 WO WO-2010-132479 11, 2010 (2013.01); C07D 403/04 (2013.01); A61 K WO WO-2011-0O2918 1, 2011 31/4155 (2013.01); C07D401/14 (2013.01); W W39: 438: A6 IK3I/4439 (2013.01); C07D 403/06 WO WO-2011-053597 5, 2011 (2013.01); A61K 31/4025 (2013.01); A61 K WO WO-2011-1 16867 9, 2011 45/06 (2013.01); A6IK3I/405 (2013.01) WO WO-2012-02462O 2, 2012 (58) Field of Classification Search W: Wi: 1585 CPC ........ A61K 31/405: A61 K 45/06 WO WO-2013-0541.85 4/2013 See application file for complete search history. WO WO-2013-061297 5, 2013 WO WO-2013-1861.59 12/2013 (56) References Cited WO WO-2014-048865 4/2014 WO WO-2014-097151 6, 2014 U.S. PATENT DOCUMENTS OTHER PUBLICATIONS 5, 186,522 A 2/1993 Spencer 5,210,574 A 5, 1993 Kita Federico et al., Mol. Endocr. 26: 786-797, 2012.* 5,538,444 A 7, 1996 Strand et al. Boucher et al., Diabetologia 48: 569-577, 2005.* 5,564,676 A 10, 1996 Goloff et al. Zou et al., Vasc. Health and Risk Management 9, 429-433, 2013.* 5,564,949 A 10/1996 Wellinsky U.S. Appl. No. 61/878,922, filed Sep. 17, 2013, Hutchinson et al. k : A & Re etet alal. U.S. Appl. No. 61/878,945, filed Sep. 17, 2013, Hutchinson et al. 7,839,888wr. B2 11/2010 Jung et al. (Continued) 7,905,958 B2 3/2011 Sasaki et al. 7,921,385 B2 4/2011 Abrams et al. 8,022,239 B2 9/2011 Parrill-baker et al. Primary Examiner — Gyan Chandra 8,268,891 B1 9, 2012 Parrill-baker et al. (74) Attorney, Agent, or Firm — Wilson Sonsini Goodrich & 8,329,907 B2 12/2012 Schultz et al. Rosati 8,343.934 B2 1/2013 Parrill-baker et al. 8,378,100 B2 2/2013 Lynch et al. 8,497,371 B2 7/2013 Parrill-baker et al. (57) ABSTRACT s: R: 858. Shea Described herein a methods and compositions for treatment 8,557,824 B2 10/2013 Schiemann et al. or prevention of metabolic disorder(s) in an individual. The 8,673,882 B2 3/2014 Gupte et al. methods and compositions disclosed herein include the use of 2006/027O634 A1 11, 2006 Miller et al. at least one autotaxin inhibitor compound. 2010, OO16258 A1 1/2010 Lynch et al. 2010, O136650 A1 6, 2010 Parrill-Baker et al. 2010/0222341 A1 9/2010 Schiemann et al. 19 Claims, 3 Drawing Sheets US 9,051,320 B1 Page 2 (56) References Cited Gupte et al. Benzyl and naphthalene methylphosphonic acid inhibi tors of autotaxin with anti-invasive and anti-metastatic activity. ChemMedChem 2011 6:922-935. OTHER PUBLICATIONS Gupte et al. Synthesis and pharmacological evaluation of the Stereoisomers of 3-carba cyclic-phosphatidic acid. Bioorg. Med. U.S. Appl. No. 61/883,026, filed Sep. 26, 2013, Hutchinson et al. Chem. Lett. 2010 20:7525-7528. U.S. Appl. No. 61/907.947, filed Nov. 22, 2013, Hutchinson et al. Hoeglund et al. Optimization of a pipemidic acid autotaxin inhibitor. U.S. Appl. No. 61/907.965, filed Nov. 22, 2013, Hutchinson et al. J. Med. 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Advanced Drug Delivery Review 19928:1-38. Chem. 2010 53:3095-3105. Bundgaard. Design and Application of Prodrugs. A Textbook of Drug Parrill et al. Autotaxin Inhibitors: A Persepctive on Initial Medicinal Design and Development 1991 Chapter 5, p. 113-191. Chemisty Efforts. Expert Opin Ther Pat 2010 20012):1619-1625. Bundgard. Design of Prodrugs. Elseview, 1985. Parrill et al. Virtual screening approaches for the identification of Cui et al. alpha- and beta-substituted phosphonate analogs of LPA as non-lipid autotaxin inhibitors. Bioorg. Med. Chem. 2008 16:1784 autotaxin inhibitors. Bioorg. Med. Chem. 2008 16:2212-2225. 1795. Cui et al. Synthesis and biological evaluation of phosphonate deriva Rancoule et al. Depot-specific regulation of autotaxin with obesity in tives as autotaxin (ATX) inhibitors. Bioorg. Med. Chem. Lett. 2007 human adipose tissue. J Physiol Biochem. 2012. 68:635-644. 17:1634-1640. Rancoule et al. Lysophosphatidic acid impairs glucose homeostasis Diagnosis and Classification of Diabetes Mellitus. Diabetes Care. and inhibits insulin Secretion in high-fat diet obese mice. Diabetolgia. 2014.37(Supp. 1):S81. 2013. 9 pgs. Durgam et al. Synthesis, structure-activity relationships, and biologi Rehman et al. Drug-Induced Glucose Alterations Part 2: Drug-In cal evaluation of fatty alcohol phosphates as lysophosphatidic acid duced Hyperglycemia. Diabetes Spectrum. 2011. 24(4):234-238. receptor ligands, activators of PPARgamma, and inhibitors of Saunders et al. Identification of Small-molecule inhibitors of autotaxin. J. Med. Chem. 2005 48:4919-4930. autotaxin that inhibit melanoma cell migration and invasion. Mol. Durgam et al. Synthesis and pharmacological evaluation of second Cancer Ther. 2008 7:3352-3362. generation phosphatidic acid derivatives as lysophosphatidic acid Skyler. Effects of Glycemic Control on Diabetes Complications and receptor ligands. Bioorg. Med. Chem. Lett. 2006 16:633-640. on the Prevention of Diabetes. Clinical Diabetes. 2004. 22(4): 162 DuSaulcy et al. Adipose-specific disruptions of autotaxin enhances 166. nutritional fattening and reduces plasma lysophosphatidic acid. J of Standards of Medical care in Diabetes—2014. Diabetes Care. 2014. Lipid Research. 2011. 52:1247-1255. 37(Supp. 1):S14. East et al. Synthesis and structure-activity relationships of tyrosine Tanaka et al.
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