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United States Patent (10) Patent No.: US 9,439,925 B2 Baker Et Al

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United States Patent (10) Patent No.: US 9,439,925 B2 Baker Et Al USOO9439925B2 (12) United States Patent (10) Patent No.: US 9,439,925 B2 Baker et al. (45) Date of Patent: Sep. 13, 2016 (54) METHODS AND COMPOSITIONS FOR 58,853. A. 358, E.er et alal. TREATING WOUNDS UTILIZING 2009/0274770 A1 11/2009 Gammelsaeter et al. CHTOSAN COMPOUNDS FOREIGN PATENT DOCUMENTS (75) Inventors: Shenda Baker, Upland, CA (US); William P. Wiesmann, Washington, JP 2003O127O2 A 1, 2003 DC (US); Ruth Baxter, Los Angeles, JP 2008507380 A 3, 2008 CA (US) WO 2004O26200 A2 4/2004 WO 200407.1186 A1 8, 2004 WO 2006O14917 A2 2, 2006 (73) Assignee: SYNEDGEN, INC., Claremont, CA WO 2010O21930 A1 2/2010 (US) WO 2011028967 A1 3, 2011 OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 Bayat A. et al., “Skin scarring.” BMJ, 2003: 326:88-92. U.S.C. 154(b) by 556 days. Doi K. et al., J. Clin Invest. 2009; 119(10):2868-78. Fang RC and Mustoe FA. “Animal models of wound healing: utility (21) Appl. No.: 13/639,560 insgenic mice.” J Biomater Sci Polym Ed. 2008; 19(8):989 1-1. Grose R. and Werner S., “Wound healing studies in transgenic and (22) PCT Filed: Apr. 6, 2011 knockout mice. A review.” Methods Mol Med. 2003; 78:191-216. Kara CO, "Animal models of sinusitis: relevance to human dis (86). PCT No.: PCT/US2O11AO31385 ease.” Curr Allergy Asthma Rep. 2004; 4(6):496-9. 371 1 Mathers et al., Invest Opthalmol Vis Sci. 1989; 30(11):2403-6. S (c)(1). Matsubara M., Invest Ophthalmol Vis Sci. 1991; 32(13):3221-37. (2), (4) Date: Dec. 14, 2012 Nakajima M. et al., Otolaryngology—Head and Neck Surgery, 131(2), 198-199, (2004). (87) PCT Pub. No.: WO2011/127144 Nemzek JA and Kim J. Comp Med. 2009: 59(4):321-30. Notification of Transmittal of the International Search Report and PCT Pub. Date: Oct. 13, 2011 the Written Opinion of the International Serachy Authority for Corresponding PCT/US2011/031385 mailed Jun. 22, 2011. (65) Prior Publication Data Olerud JE, “Models for diabetic wound healing and healing into percutaneous devices.” J Biometer Sci Polym Ed. 2008; 19(8): US 2013/0210761 A1 Aug. 15, 2013 1007-20. Roques C. et al., Lower Extremity Wounds, 2007; 6(4):249-53. Santos Heredero FX et al., Annals of Burns and Fire Disasters, IX-n. Related U.S. Application Data 2Schon (Jun., MP, 1996). “Animal models of psoriasis: a critical appraisal.” Exp (60) Provisional application No. 61/321,437, filed on Apr. Dermatol. 2008; 17(8):703-12. On6, 2010,Mar. provisional10, 2011. application No. 61/451,430, filed S.emonerapy, Sh et al. Ural. At Surg UralMes Med SoNS Ural Fanol, 's , pp.y 45 -45, s (1990). Stevenson JM et al., Methods Mol Med. 2003; 78:95-105. (51) Int. Cl. Supplementary European Search Report from corresponding Euro A6 IK3I/722 (2006.01) pean Application EP 11766639 dated Jul 23, 2013. A6 IK 47/48 (2006.01) Alsarra et al. "Chitosan topical gel formulation in the management A6IL 26/00 (2006.01) of burn wounds” International Journal of Biological Macromol 52) U.S. C ecules (2009) vol. 45. pp. 16-21. (52) AV e. we Jawad et al. “Effect of Chitosan Sheets on Wound Healing” Basrah CPC ......... A6 IK3I/722 (2013.01); A61K 47/4823 Journal of Veterinary Research (2007) vol. 6, pp. 81-95. (2013.01); A61L 26/0023 (2013.01); A61L Kweon et al. "Preparation of water-soluble chitosan?heparin com 26/0066 (2013.01); A61 L 2300/404 (2013.01); plex and its application as wound healing accelerator Biomaterials A61 L 2300/41 (2013.01); A61 L 2300/64 (2003) vol. 24, pp. 1595-1601. (2013.01) Ueno et al. “Topical formulations and wound healing applications of chitosan' Advanced Drug Delivery Reviews (2001) vol. 52, pp. (58) Field of Classification Search 105-115. CPC ............ A61K 3 1/722: A61K 47/4823; A61L A61L 2300/64; A61L 2300/41; C08L 5/08 Assistant Examiner — Michael C Henry USPC . 5 1455; 536/20 (74) Attorney, Agent, or Firm — Lando & Anastasi, LLP See application file for complete search history. (56) Refeerees Citede (57) ABSTRACT Described herein are methods of treating wounds, the U.S. PATENT DOCUMENTS method comprising administering to a Subject an effective amount of a composition comprising a soluble or derivatized 4,532,134 A 7, 1985 Malette et al. chitosan wherein the soluble or derivatized chitosan when 6,114,382 A 9, 2000 Moretti 6,962,151 B1 1 1/2005 Knoch et al. administered contacts the wound, thereby treating the 7,618,382 B2 11/2009 Vogel et al. wound. 8,119,780 B2 2/2012 Baker et al. 2006, OO29675 A1 2/2006 Ginther 10 Claims, 16 Drawing Sheets U.S. Patent Sep. 13, 2016 Sheet 1 of 16 US 9,439,925 B2 F.G. U.S. Patent Sep. 13, 2016 Sheet 2 of 16 US 9,439,925 B2 FG. 2 U.S. Patent Sep. 13, 2016 Sheet 3 of 16 US 9,439,925 B2 U.S. Patent Sep. 13, 2016 Sheet 4 of 16 US 9,439,925 B2 FIG. 4 Chitosa arginie eithaaces ERK phosphesyatic; it response to sibiaxia E{S. Cicestrati: in Cacc2 ces 60000 p. 50000 40000 u or or 3.88 - pits CA 2000) 10000 - --------- ----- - is 33 gfrit 333 gif U.S. Patent Sep. 13, 2016 Sheet S of 16 US 9,439,925 B2 FGS Cisitosa argisine of different toleculiar weights arc degree of fuctionalisatio, ad chitosa gy coic acid aii enhance E{s: induced ERK piosphorylation 23030 go --YYYYYYYYYYYYYYYYYYYYYYYYYYYY......YYYYYYYYYYYYYYY......'Y'Y'Y'Y'Y'Y'YYYYYYYaxxxxYYYYYYYYYYYYYY......SYYYYYYY 3 : 8 ::issisi is: 8ws: : cit:33, 3ervative 8 : gias E8 43000 20000 imm. a-a-a-a- a-a-a-a-a-a-a-a-a-a-a--------a-a-a-a-a-a-a-a-a- U.S. Patent Sep. 13, 2016 Sheet 6 of 16 US 9,439,925 B2 F.G. 6 Chitosar argiine enhances Caiiage prodiction by 38-3 8 m --~: 16 8 8c::::::: if A 88: CfA -- (383&ta i{}} :gfi {gf: U.S. Patent Sep. 13, 2016 Sheet 7 of 16 US 9,439,925 B2 FG. 7 2SO - - - - - - - - - - - - - - - - - - - - - - - - - - - - - is a 33 gi: S. x:S girl 8 A . P: U.S. Patent Sep. 13, 2016 Sheet 8 of 16 US 9,439,925 B2 FG, 8 SN-9: Bay 2 Endscay Colitis Sewerity Scores kites:} Weisie 1 : Figig 4 mg/kg 43rgikg Precisclose CA CA facis jigikg 4 g/kg 4-Gngkg Eisge CA CA U.S. Patent Sep. 13, 2016 Sheet 10 of 16 US 9,439,925 B2 FIG. O. g * Group 3 - Wg::cie Contro: OS 2. -8-Grop 1 - Wehicle Contre of * Group 2 - Fest Attice 3 QS * Group 2 - Test Aricket OE) 13 * Graig 3 - Fest Attice 2 (S 3roup 3 -ast Aricke 2 3 10.0 0 2 24 36 48 SO 72 84 96 08 20 132 144 56 S8 80 192 204 236 ...itis...ife...itai:3.isagy. U.S. Patent Sep. 13, 2016 Sheet 11 of 16 US 9,439,925 B2 8 Group - Vehicle 8 : Conio OS 2.0 & Group 2 - Fest Alicies CS .8. Sroup 3 fest Articia OS . { ---- --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- 3 : 34 38 48 80 F2 34 38 38 3: 32 44 58 88 8 92 24 3 otickirs site.initiating. Sherapy. U.S. Patent Sep. 13, 2016 Sheet 12 of 16 US 9,439,925 B2 4000000 2000000 & 3roug : - Wehicle Control OS 000000.8 & Grog 2 - Fest Articia OS : Gro; 3 -ies: Article 2 OS 8 0. C 80s. 203000.G : O : 24; 38 43 S. F2 84 8 8 2. 32 44 58 88 88 12 234 3 ours after streas origig U.S. Patent Sep. 13, 2016 Sheet 13 of 16 US 9,439,925 B2 O : * Group : - Vehicle 90 ; Corto S so -8- Group 2 - Fest Alice S * Greip 3 - as Alicise 2 (OS 3. -&-----: O 2. 33 33 48 6. 2. 33. 8 2 3 44 58 88 8 S 24, 28 oto:S site.cgresseggiading. U.S. Patent Sep. 13, 2016 Sheet 14 of 16 US 9,439,925 B2 FIG. 4 ite {{s} U.S. Patent Sep. 13, 2016 Sheet 15 of 16 US 9,439,925 B2 FG. SA FG. SB U.S. Patent Sep. 13, 2016 Sheet 16 of 16 US 9,439,925 B2 F.G. 6 I-8 pagfis is 3 speratast wer isixtec wit was it is acteries wits ex witat retreatest CA s 3. 88. 88: Straig Ex. xiii. ss. US 9,439,925 B2 1. 2 METHODS AND COMPOSITIONS FOR or derivatized chitosan wherein the soluble or derivatized TREATING WOUNDS UTILIZING chitosan when administered contacts the wound, thereby CHTOSAN COMPOUNDS treating the wound. In an embodiment, the composition reduces the healing PRIORITY CLAIM time or increases the healing rate of the wound. In some embodiments, the composition decreases the inflammation The present application claims the benefit of U.S. provi associated with wound or healing of the wound. In some sional application Nos. 61/321,437, filed on Apr. 6, 2010, embodiment, the composition decreases the magnitude or and 61/451,430, filed on Mar. 10, 2011. The contents of the extent of scarring. 10 In an embodiment, the Subject or wound is not infected, aforementioned applications are incorporated herein by ref e.g., bacterially or virally infected, when treated with the erence in their entirety. composition. In another embodiment, the Subject or wound is infected, e.g., bacterially or virally infected, when treated FIELD OF THE INVENTION with the composition.
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