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(12) United States Patent (10) Patent No.: US 9,662.400 B2 Smith Et Al

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(12) United States Patent (10) Patent No.: US 9,662.400 B2 Smith Et Al USOO9662400B2 (12) United States Patent (10) Patent No.: US 9,662.400 B2 Smith et al. (45) Date of Patent: *May 30, 2017 (54) METHODS FOR PRODUCING A (2013.01); C08B 37/003 (2013.01); C08L 5/08 BODEGRADABLE CHITOSAN (2013.01); A6 IK 38/00 (2013.01); A61 L COMPOSITION AND USES THEREOF 2300/404 (2013.01) (58) Field of Classification Search (71) Applicant: University of Memphis Research CPC ...... A61K 47/36; A61K 31/00; A61K 9/7007; Foundation, Memphis, TN (US) A61K 9/0024; A61 L 15/28: A61L 27/20; A61L 27/58: A61L 31/042; C08B 37/003 (72) Inventors: James Keaton Smith, Memphis, TN USPC ................................ 514/23, 40, 777; 536/20 (US); Ashley C. Parker, Memphis, TN See application file for complete search history. (US); Jessica A. Jennings, Memphis, (56) References Cited TN (US); Benjamin T. Reves, Memphis, TN (US); Warren O. U.S. PATENT DOCUMENTS Haggard, Bartlett, TN (US) 4,895,724. A * 1/1990 Cardinal .............. A61K9/0024 424,278.1 (73) Assignee: The University of Memphis Research 5,541,233 A 7/1996 Roenigk Foundation, Memphis, TN (US) 5,958,443 A 9/1999 Viegas et al. 6,699,287 B2 3/2004 Son et al. (*) Notice: Subject to any disclaimer, the term of this 6,989,157 B2 1/2006 Gillis et al. patent is extended or adjusted under 35 7,371.403 B2 5/2008 McCarthy et al. 2003, OO15825 A1 1/2003 Sugie et al. U.S.C. 154(b) by 0 days. 2003/0206958 A1 11/2003 Cattaneo et al. 2007/00594.73 A1 3/2007 Yamazaki et al. This patent is Subject to a terminal dis 2009,0004276 A1 1/2009 Ben-Shalom et al. claimer. 2009.0075383 A1 3/2009 Buschmann et al. 2012fO149659 A1 6/2012 Haggard et al. (21) Appl. No.: 14/771,617 (22) PCT Fed: Mar. 14, 2013 FOREIGN PATENT DOCUMENTS (86) PCT No.: PCT/US2O13/031622 EP 1308.177 5, 2003 JP O2-268766 11, 1990 S 371 (c)(1), JP 2003/511120 3, 2003 (2) Date: Aug. 31, 2015 JP 2004, 231604 8, 2004 JP 2006,347999 6, 2005 PCT Pub. No.: WO2O14/142915 JP 2006,516988 T 2006 (87) JP 2008-110207 5, 2008 PCT Pub. Date: Sep. 18, 2014 JP 2008, 161502 T 2008 JP 2008.527.033 T 2008 Prior Publication Data KR 10-2002-0017552 3, 2002 (65) KR 102002001 7552 A 3, 2002 KR 1020040090033. A 10, 2004 US 2016/0000924 A1 Jan. 7, 2016 KR 2007 O118730. A 12/2007 (51) Int. C. (Continued) A6 IK 47/36 (2006.01) A6 IK 38/14 (2006.01) OTHER PUBLICATIONS A6 IK 38/12 (2006.01) The Merck Manual 1992, pp. 183-189.* A6 IK3I/7036 (2006.01) Parker et al. J. Biomedical Materials Research B: Applied A6IL 5/28 (2006.01) Biomaterials, 2013, 101b(1), 110-123.* C8B 37/08 (2006.01) Smith, J.K. et al., “Antibiotic-loaded chitosan film for infection COSL 5/08 (2006.01) prevention: A preliminary in vitro characterization.” Journal of A6IL 27/20 (2006.01) Biomedical Materials Research Part B: Applied Biomaterials, 2010, A6IL 27/54 (2006.01) vol. 94B, pp. 203-211 (see abstract and p. 204). A6IL 27/56 (2006.01) Parker, A.C. et al., “Preliminary investigation of crosslinked chitosan Sponges for tailorable drug delivery and infection control.” A6IL 5/42 (2006.01) Journal of Biomedical Materials Research Part B: Applied A6IL I5/46 (2006.01) Biomaterials, Sep. 21, 2012 (E-pub.), vol. 101B, pp. 110-123, See A 6LX 9/19 (2006.01) abstract: and pp. 111 and 112. A 6LX 9/70 (2006.01) A6 IL 7/10 (2006.01) (Continued) A61 K 38/00 (2006.01) Primary Examiner — Ganapathy Krishnan (52) U.S. C. (74) Attorney, Agent, or Firm — Melissa Hunter-Ensor; CPC ................ A61K 47/36 (2013.01); A61K 9/19 Elbert Chiang; Greenberg Traurig, LLP (2013.01); A61K 9/70 (2013.01); A61 K (57) ABSTRACT 3 1/7036 (2013.01); A61K 38/12 (2013.01); A61K 38/14 (2013.01); A61 L 15/28 (2013.01); The invention provides improved methods for generating A61L 15/425 (2013.01); A61 L 15/46 biodegradable chitosan compositions, and therapeutic meth (2013.01); A61L 17/10 (2013.01); A61L 27/20 ods of using Such compositions to deliver therapeutic agents. (2013.01); A61L 27/54 (2013.01); A61L 27/56 17 Claims, 3 Drawing Sheets US 9,662.400 B2 Page 2 (56) References Cited Bonferoni et al., "Chitosan Gels for the Vaginal Delivery of Lactic Acid: Relevance of Formulation Parameters to Mucoadhesion and Release Mechanisms”, AAPS PharmSciTech 2006; 7 (4) Article 104 FOREIGN PATENT DOCUMENTS (http://www.aapspharmscitech.org). WO Of 41820 A1 6, 2001 International Search Report issued for International Application No. WO 2004/078063 A2 9, 2004 PCT/US2010/027481, completed Oct. 28, 2010 and mailed Nov. 2, WO 2008.157318 A2 12/2008 2010. WO 2009/0566O2 A1 5, 2009 Antonov et al., “Study of Wound Healing Properties of Chitosan'. Russian Agricultural Sciences, vol. 34, No. 6, pp. 426-427 (2008). OTHER PUBLICATIONS Kiang et al., “The effect of the degree of chitosan deacetylation on Notification of Transmittal of the International Search Report and the efficiency of gene transfection'. Biomaterials, vol. 25, pp. the Written Opinion of the International Searching Authority in 5293-5301 (2004). corresponding PCT/US2013/031622, dated Nov. 26, 2013 (14 European Search Report issued in European Patent Application No. pages). 10753982.7 on Aug. 6, 2013. Niekraszewicz; "Chitosan Medical Dressings'. Institute of Chemi JP Office Action, issued in JP App No. 2012-500887 (translation), cal Fibres ul. M. Sklodowskiej-Curie 19/27, 90-570 Lodz, Poland, mailed Jan. 7, 2015. Fibres & Textiles in Eastern Europe Jan./Dec. 2005, vol. 13, No. 6 (54). * cited by examiner U.S. Patent May 30, 2017 Sheet 1 of 3 US 9,662.400 B2 U.S. Patent May 30, 2017 Sheet 2 of 3 U.S. Patent May 30, 2017 Sheet 3 of 3 US 9,662.400 B2 Figure 3 Primex 61% (58%) Š Primex 61% Buffered (58%) Primex Reacetylated (53%) Š Primex Reacetylated Buffered (53%) HMC 751500 (71%) HMC 75/580 Buffered (71%) HMC Reacetylated (87%) HMC Reacetylated Buffered (87%) Chitopharm S (82%) Chitopharm Buffered S (62%) sy Chitopham Reacetylated (55%) Chitopharm Reacetylated Buffered (55%) sy 10 20 30 40 50 60 70 80 90 100 Percent Remaining (%) US 9,662,400 B2 1. 2 METHODS FOR PRODUCING A (b) forming the chitosan into a desired shape under BODEGRADABLE CHITOSAN conditions that reduce the water content by about COMPOSITION AND USES THEREOF 10%-100%. (c) neutralizing the chitosan composition by contacting STATEMENT OF RIGHTS TO INVENTIONS 5 the composition with water, a neutral, or a basic solu MADE UNDER FEDERALLY SPONSORED tion, wherein the water, neutral, or basic solution is RESEARCH Selected to modulate a physical-mechanical property of the chitosan; and This work was supported by the following grants from the (d) contacting the chitosan composition with an acid U.S. Department of the Army: USAMRAA Grant No. 10 buffer wash, thereby producing a biodegradable chito W81XWH-12-2-0020. The government has certain rights in San composition. the invention. In another aspect, the invention provides a chitosan com This application is the U.S. national phase application, position produced by the method of the previous aspect, or pursuant to 35 U.S.C. S371, of PCT international application any other method described herein. Ser. No. PCT/US2013/031622, filed Mar. 14, 2013, desig 15 In another aspect, the invention provides a wound man nating the United States and published in English. The entire agement device containing a chitosan composition produced contents of the aforementioned patent applications are incor by the method described in the previous aspects. In one porated herein by this reference. embodiment, the device contains an effective amount of a therapeutic agent. In another embodiment, the effective BACKGROUND OF THE INVENTION amount of the agent is sufficient to reduce the Survival or proliferation of a bacterial cell. In still another embodiment, The skin serves as an important barrier to infection. Any the agent is an antibiotic selected from the group consisting trauma that breaks the skin creates an opportunity for of daptomycin, Vancomycin, and amikacin. In still another pathogen entry and infection. Open fractures are ideal sites embodiment, the agent is any one or more of growth factor, for infection. Surgical site infections in closed fractures 25 anti-inflammatory, hemostatic, and anti-thrombotic. In still range from 3.6-8.1%. In contrast, Surgical site infections in another embodiment, the agent is an anti-bacterial, anti open fractures range from 17.5-21.2%. Pathogens present at viral, or anti-fungal agent. the site of an open fracture may create not only local In another aspect, the invention provides a method for infections, but can also cause serious infections in the bone treating or preventing an infection in a subject at a site of and associated tissues. Complex open wounds are also prone 30 trauma, the method involves contacting the site with a to infection with a number of bacteria. The type of bacteria chitosan composition or a wound management device of any infecting the wound typically varies depending on the cause previous aspect. In other embodiments, the method further of the trauma. To reduce the risk of infection, the current involves irrigating and debriding the site of trauma. In other standard of care involves debridement, irrigation, and sys embodiments, the composition or device contains an agent temic antibiotic therapy. Even with aggressive therapies and 35 that is any one or more of antimicrobial agent, growth factor, systemic antibiotic treatment, infections remain a significant anti-inflammatory, hemostatic agent, and anti-thrombotic.
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