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(12) United States Patent (10) Patent No.: US 9,150,613 B2 Harding Et Al

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(12) United States Patent (10) Patent No.: US 9,150,613 B2 Harding Et Al US009 150613B2 (12) United States Patent (10) Patent No.: US 9,150,613 B2 Harding et al. (45) Date of Patent: Oct. 6, 2015 (54) HEPATOCYTE GROWTH FACTOR MIMICS C07K5/083 (2006.01) AS THERAPEUTICAGENTS A61 K38/00 (2006.01) (52) U.S. Cl. (75) Inventors: Joseph W. Harding, Pullman, WA (US); CPC. C07K 5/02 (2013.01); A61K38/06 (2013.01); John W. Wright, Pullman, WA (US); A6 IK38/07 (2013.01); A61K 45/06 (2013.01); Caroline C. Benoist, Nashville, TN C07K 5/021 (2013.01); C07K5/0808 (US); Leen H. Kawas, Pullman, WA (2013.01); A61 K38/00 (2013.01) (US); Gary A. Wayman, Pullman, WA (58) Field of Classification Search (US) None See application file for complete search history. (73) Assignee: Washington State University, Pullman, WA (US) (56) References Cited (*) Notice: Subject to any disclaimer, the term of this U.S. PATENT DOCUMENTS past list: G adjusted under 35 2005/O113369 A1 5.2005 Zembower et al. M YW- y yS. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 14/009,459 EP O 805203 5, 1997 (22) PCT Filed: Apr. 2, 2012 WO WO 2008OO5531 * 1 2008 WO 2011 019400 2, 2011 (2),S371 (4) (c)(1), Date: Dec. 9, 2013 B.J. Yamamoto et al.:"The Angiotensin IV Analog Nile-Tur-Leu-psi s 9 (CH2-NH2)3-4-His-Pro-Phe (Norleual) Can Act as a Hepatocye (87) PCT Pub. No.: WO2012/138599 Growth Factor/c-Met Inhibitor'; Pharmacology and Experimental Therapeutics, vol. 333, No. 1, 2010, pp. 161-173. PCT Pub. Date: Oct. 11, 2012 * cited by examiner (65) Prior Publication Data Primary Examiner — Thomas S Heard US 2014/OO88004 A1 Mar. 27, 2014 (74) Attorney, Agent, or Firm — Whitham Curtis Christofferson & Cook, PC Related U.S. Application Data (60) Provisional application No. 61/471,122, filed on Apr. (57) ABSTRACT 2, 2011, provisional application No. 61/471,124, filed Small molecule, peptidic hepatocyte growth factors mimics, on Apr. 2, 2011. which act as both mimetics and antagonists, have been gen erated. These molecules have been shown or predicted to have (51) Int. Cl. therapeutic potential for numerous pathologies including C07K 5/02 (2006.01) dementia, neurodegenerative disease, diabetes and metabolic A6 IK38/06 (2006.01) syndrome, cancer, and defective wound healing. A6 IK38/07 (2006.01) A6 IK 45/06 (2006.01) 1 Claim, 39 Drawing Sheets U.S. Patent Oct. 6, 2015 Sheet 1 of 39 US 9,150,613 B2 s 3 80 ww.-.----- --1-1 “. ....--. ScoggiannineCS i\.- •rk- ?exa-Cyy st i. \; -- iexa-high w sa. ww. s VX s wr- i. & s.rssssss www.www.www.www.www.www.www.www.www.www.www.www.---------------- a S 8 83 Acquisition (ciays Figure 1A 2 ... -- Xs Yr aar eaa e - re-ra r N- ------ A& 100i. wa * - 5, 80: \ + Ms. C3 . $ \ --ts p. -- Scopeiarine s& 60NY-- ^ ---i. i -- 3:hexa-iowa. S 40- isY. --- * s Mw -- Dihexa-high {} gorgo sororogo -- 2 3 8 8 Acquisition (iays Figure 1B 18 -8-- - -3ts: -- hexa Acquisition days Figure 1C U.S. Patent Oct. 6, 2015 Sheet 2 of 39 US 9,150,613 B2 sits 3. 33- r...waxww. :s sts S E. 28 w s:a & s for: f s: f a 8 crways ---------------& 8 ----- Contre: Dihexa (M Ritaxa (3-138A Bisexa (v. Diexa 4-3, Figure 2A 3. 3. Control ak O2, Nie-Angiw Oh, Nie-Angiv City Mis-Angly Figure 2B U.S. Patent Oct. 6, 2015 Sheet 4 of 39 US 9,150,613 B2 Contro: Mie-Aisgivi Dhexa Figure 4 ARFP-3-Actin y vierged {{}}to Niei-Agiv sex3 MRF-8-Actin &y 333i: verged Citi -jie-Arg 38xas vierged Citro 8i-Argiv isex8 Figure 5A U.S. Patent Oct. 6, 2015 Sheet 5 of 39 US 9,150,613 B2 hi:mber of Sgies s: : ............ sk........w. w Cotto: Nie-Angly 388xa C8::tro ||Niet-Aigy Dihexa Syriapsi Syriapsi Figure 5B Figure 5C 38 cefit featio: Number of Sp88s 8 i ---assa 4: 3. 28 0-ri-i-imid-i- Toontro Nie-Angly hexa Contro Nie-Angly 388x3 f3. Figure 5D Figure 5E Nisbef of Spies 88. S{ 2 s Contro: Kiisi-Angiw Rihexa cotto: hite Agy 388x3 8-93 S-3S Figure 5F Figure 5G U.S. Patent Oct. 6, 2015 Sheet 6 of 39 US 9,150,613 B2 - 8 on c: 3: 6 i. ii 4 x-ax. 2 : & 3. r 3. 3. { ...iwi. Saarwaxxx-x-xxaaw {:};to Nie-Argiv 8x8 Figure 6A sati's Nie-Angiv Y --a- 8 * . ga, 30 sea Figure 6B U.S. Patent Oct. 6, 2015 Sheet 7 Of 39 US 9,150,613 B2 Figure 7A S 8 Cofirest Nie-Angv Dihexa Figure 7B U.S. Patent Oct. 6, 2015 Sheet 8 Of 39 US 9,150,613 B2 3. 2 Corio HGF 5ngimi HGF 20ngirn: 32.5ngiri if Ogiri Figure 8 Figure www. S. Contre: Mei-Agivwwww.ws 8xa Figure 9B U.S. Patent Oct. 6, 2015 Sheet 9 Of 39 US 9,150,613 B2 C Citi HGF tongin {{fire; 6f 6ft" Syasi f : Figure 1 OA Figure 1 OB Citro g on r inter Figure 10C Figure 10D f : s Cofit ihexa Figure 11 U.S. Patent Oct. 6, 2015 Sheet 10 Of 39 US 9,150,613 B2 : & & X 30- & SS cio 3. s: s 33 3. •e ... A. Ef *3. 8-w s: (3-i --- ----------------- r | .. Rig 10%ki saxa | 10-12.--Mer Dihexa 2.5igin; i3- $3rgin higF i jiaxa + $36FS Figure 12A s 2 {88; {GF2. Sigiri iGF (sigfin Nie Ángs, 0 3 88-Afg. {{ 2 Nie-i-Argivis, HGS Figure 12B U.S. Patent Oct. 6, 2015 Sheet 11 Of 39 US 9,150,613 B2 3. 33. s 2. Contra -38s, Hings 8-33& 3:hexa 1388, inge 48-28, 8 -irge -2&ige Figure 13A Figure 13B {{}: tige * C w.x.y. 8:8.. Argy:. C:8: {-2,s iristiing: i-tahix kinges. 332. Nai-Argy 0-32&tings 8X{{-18, 8x8 Figure 13C Figure 13D U.S. Patent Oct. 6, 2015 Sheet 12 Of 39 US 9,150,613 B2 NOE 3$3${}}{} s 3 : 30 A 8:83. p?infit-3 R As s z f scu go Áatisfai U.S. Patent Oct. 6, 2015 Sheet 14 of 39 US 9,150,613 B2 & Dihexa -128 kiGF (Ongimi Oshexa t}-12hi Dhexa -M freatment&roups HSF5Origin: - Contre: {{GF 00.gimi HG 53rgini Dhexes to 12, Dihexa 43-28. Dihexa 0-08. Figure 16 HGF 5{ng - -- - - - *- : . HGF25rg - w w w kiGF .25ng . - - - - Dihexa 3-2 -- + - - or r iska 0-38? w |- -- |- on to Figure 17 U.S. Patent Oct. 6, 2015 Sheet 15 of 39 US 9,150,613 B2 . ... -- ... 'S', '88. Figure 18 Non-transfected C-Met-68wyc 2) {i+2} set Citro Diaxa i Spines HGF Nie-Angly sileiSpines Haf Nie-Argivset Spiites Figure 20 U.S. Patent Oct. 6, 2015 Sheet 16 of 39 US 9,150,613 B2 -8- a CSxaS --8- Scopolarie-a(SF SC wk Scopeian inaYihexa - Scopolaniefinge-Diexa -- at Sax3 8- -tirge-acSF Acquisition (days} Figure 21 3 80 ww. sm . 3 M3 - - - - - - Š 4. f 20- A - {} 68 8) 18; 3.38 3} fire (min) Figure 22 U.S. Patent Oct. 6, 2015 Sheet 17 Of 39 US 9,150,613 B2 80000 ë S3{{{ . : 40000 , 8 20000 8 x Y - 4 -3 { -8 -6 iggvi Figure 23 &Wikia is 8:--> visitief. Her -- -- -- s Nike-Ki-6A-A life r iys y Figure 24A 5 O 50-8 Tyr {YS 3 & corpoard Oov, Figure 24B U.S. Patent Oct. 6, 2015 Sheet 18 of 39 US 9,150,613 B2 ief 4 k3 ifei 40 ki3 area oooooooooooooooooo- 8xxxxaaw {{3F2Origin oric Eyr 8-tight Qys (-i68A ?p10-40, i.e. i - 08. Contra: 'yr Cys Erg Met 30 rigin compound 8-10M Figure 25 A ord? as 8 i. {} Treatient groups Figure 26 U.S. Patent Oct. 6, 2015 Sheet 19 of 39 US 9,150,613 B2 602 --- ***... SSSSSSSSSSSSSSSSSS-?ºo,o?SSSSSSSSSSSSSSSSSSSSSS-wg-g! ?<&&&&&§§*************************· ~~~~--~~~~|~~~~: w gir-C8 w U.S. Patent Oct. 6, 2015 Sheet 20 Of 39 US 9,150,613 B2 St. --------YYY-Y-wr-www.www.www.www.www.www.alasa O-6 8 w iN 100 3-3 s A. 8. 1 Y ; 10-8 w 8 -1 ... 30 w tax 1 C-:s: & Š - sasssssasssssssssssXaxw Y.-- O S. {{ i{ Ceti Scattering (%-GF Figure 28 U.S. Patent Oct. 6, 2015 Sheet 21 of 39 US 9,150,613 B2 818F 10 + Cys 846-0 + Cys 00:gik.gif) iigikgf Figure 29A 3. 150 . e i i st 100 : SC: Rs 36- Cys gikgfday CyS 00.gikgiday Figure 29B U.S. Patent Oct. 6, 2015 Sheet 23 Of 39 US 9,150,613 B2 figure 3&- U.S. Patent Oct. 6, 2015 Sheet 24 of 39 US 9,150,613 B2 Brain Regions Fig:re 32 U.S. Patent Oct. 6, 2015 Sheet 25 Of 39 US 9,150,613 B2 83 ex ag Figure 33 U.S. Patent Oct. 6, 2015 Sheet 27 Of 39 US 9,150,613 B2 resisters: see:& exis& 88ssex Figure 38&- U.S. Patent Oct. 6, 2015 Sheet 28 Of 39 US 9,150,613 B2 150 -k- Vehicle (O) rare Dihexa-2.Ongfkg rairing Day Figare 37 U.S. Patent Oct. 6, 2015 Sheet 29 Of 39 US 9,150,613 B2 8. i. s s & Sigire 38A-8 U.S. Patent Oct. 6, 2015 Sheet 30 Of 39 US 9,150,613 B2 to & 8 ar ors 8.: 8, s: xiis'Agif 8x3 Figare 39 U.S.
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