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(12) United States Patent (10) Patent No.: US 8,993,540 B2 Haggard Et Al

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(12) United States Patent (10) Patent No.: US 8,993,540 B2 Haggard Et Al US00899.3540B2 (12) United States Patent (10) Patent No.: US 8,993,540 B2 Haggard et al. (45) Date of Patent: Mar. 31, 2015 (54) COMPOSITIONS AND METHODS FOR C08B 37/003: A61L 31/042: A61L 27/58: DELIVERING ANAGENT TO AWOUND A61L 27/20: A61 L 15/28 (75) Inventors: Warren O. Haggard, Bartlett, TN (US); spicion is reopelli" Scott P. Noel, Arlington, TN (US); Joel D. Bumgardner, Memphis, TN (US) (73) Assignee: University of Memphis Research (56) References Cited Foundation, Memphis, TN (US) U.S. PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this 4,895,724. A * 1/1990 Cardinal et al. .............. 424/418 patent is extended or adjusted under 35 5,541.233 A * 7/1996 Roenigk ......................... 521,54 U.S.C. 154(b) by 42 days. 5,958,443 A 9/1999 Viegas et al. 6,699,287 B2 3/2004 Son et al. (21) Appl. No.: 13/256,585 6,989,157 B2 * 1/2006 Gillis et al. ................... 424,618 7,371.403 B2 5/2008 McCarthy et al. (22) PCT Filed: Mar. 16, 2010 2003, OO15825 A1 1/2003 Sugie et al. 2003/0206958 A1 11/2003 Cattaneo et al. (86). PCT No.: PCT/US2O10/027481 2007/00594.73 A1* 3, 2007 Yamazaki et al. ........... 428/40.1 2009,0004276 A1 1/2009 Ben-Shalom et al. S371 (c)(1), 2009.0075383 A1 3/2009 Buschmann et al. (2), (4) Date: Feb. 27, 2012 FOREIGN PATENT DOCUMENTS (87) PCT Pub. No.: WO2010/107794 EP 1308 177 A1 5, 2003 PCT Pub. Date: Sep. 23, 2010 JP O2-268766 11, 1990 JP 2003-511 120 3, 2003 (65) Prior Publication Data JP 2004-231604 8, 2004 JP 2006-347999 6, 2005 US 2012/O149659 A1 Jun. 14, 2012 JP 2006-516988 7, 2006 JP 2008-110208 5, 2008 JP 2008-161502 T 2008 Related U.S. Application Data JP 2008-527033 T 2008 KR 10-2002-0017552 3, 2002 (60) Provisional application No. 61/160,539, filed on Mar. KR 2002-0017552 * 3, 2002 .............. A61L 27.60 16, 2009, provisional application No. 61/171,805, KR 102002OO1755 A * 7, 2002 ........... A61L 27.60 filed on Apr. 22, 2009, provisional application No. KR 10-2004-0090033 10, 2004 61/227,606, filed on Jul. 22, 2009. KR 20040090033 10/2004 .............. A61L 27.60 KR 2007 O118730. A 12/2007 (51) Int. C. (Continued) A 6LX3L/75 (2006.01) A6IP3/04 (2006.01) A6IP3L/2 (2006.01) OTHER PUBLICATIONS A6IP 7/02 (2006.01) Merck Manual, 1992, pp. 183-189, 1460-65.* C7H I/00 (2006.01) (Continued) A6 IK 47/36 (2006.01) A6 IK3I/00 (2006.01) A6IL 5/28 (2006.01) A6IL 27/20 (2006.01) Primary Examiner — Ganapathy Krishnan A6L 27/58 (2006.01) (74) Attorney, Agent, or Firm — Saul Ewing LLP; Melissa A6IL 3L/04 (2006.01) Hunter-Ensor C8B 37/08 (2006.01) COSL 5/08 (2006.01) A61 K9/00 (2006.01) (57) ABSTRACT A61 K9/70 (2006.01) (52) U.S. Cl. The invention provides compositions featuring chitosan and CPC ................. A61K 47/36 (2013.01); A61 K3I/00 methods for using Such compositions for the local delivery of (2013.01); A61L 15/28 (2013.01); A61L 27/20 biologically active agents to an open fracture, complex (2013.01); A61L 27/58 (2013.01); A61L 31/042 wound or other site of infection. Advantageously, the degra (2013.01); C08B 37/003 (2013.01); C08L 5/08 dation and drug elution profiles of the chitosan compositions (2013.01); A61 K9/0024 (2013.01); A61 K can be tailored to the needs of particular patients at the point 9/7007 (2013.01) of care (e.g., in a Surgical Suite, clinic, physicians office, or USPC .......................................... 514/55; 536/1231 other clinical Setting). (58) Field of Classification Search CPC ... A61 K9/0024; A61 K9/7007; A61 K31/00; A61K 47/36; A61K 2300/00; CO8L 5/08: 17 Claims, 33 Drawing Sheets US 8,993,540 B2 Page 2 (56) References Cited Fibres & Textiles in Eastern Europe Jan./Dec. 2005, vol. 13, No. 6 (54). FOREIGN PATENT DOCUMENTS Bonferoni et al., “Chitosan Gels for the Vaginal Delivery of Lactic Acid: Relevance of Formulation Parameters to Mucoadhesion and WO WO 01/41820 A1 6, 2001 Release Mechanisms”, AAPS PharmSciTech 2006; 7 (4) Article 104 WO WO 2004/078063 A2 9, 2004 (http://www.aapspharmscitech.org). WO WO 2008.157318 A2 12/2008 International Search Report issued for International Application No. WO WO 2009/0566O2 A1 5, 2009 PCT/US2010/027481, completed Oct. 28, 2010 and mailed Nov. 2, OTHER PUBLICATIONS 2010. Antonov et al., “Study of Wound Healing Properties of Chitosan'. European Search Report issued in European Patent Application No. Russian Agricultural Sciences, vol. 34, No. 6, pp. 426-427 (2008). 10753982.7 on Aug. 6, 2013. Kiang et al., “The effect of the degree ofchitosan deacetylation on the JP Office Action, issued in JP App No. 2012-500887 (translation), efficiency of genetransfection'. Biomaterials, vol. 25, pp. 5293-5301 mailed Jan. 7, 2015. (2004). Niekraszewicz; "Chitosan Medical Dressings'. Institute of Chemical Fibres ul. M. Sk odowskiej-Curie 19/27, 90-570 - 6dz, Poland, * cited by examiner U.S. Patent Mar. 31, 2015 Sheet 1 of 33 US 8,993,540 B2 O CD O SS s C ? O o N ; %2 a NN N O O O O O O O CO CO V CN V (u/fin) uoeueouoso uoexuW U.S. Patent Mar. 31, 2015 Sheet 2 of 33 US 8,993,540 B2 O Z as CN <f O n o v O O (AS S Z N d 2121211 CN N Fl <d S NSN 112111 NNN s3 N S N 1111 8 O NNNNNNNNNNN Z S > NSN S. 2121111 <d N ? S O N o 11-1211-11 N NNN | SS O N. CO 1-1-1-1-1-1-1-1 Z NNNNNNNNN d S N. Y. <d 11111111111 h N S N N ve 11212111121111111 NNNNNNNNNNNNNNNNNNNNNNNNNNNNNNN O Z O w s d 3 Lo (u/fin) buo Xu W O <d O o N U.S. Patent Mar. 31, 2015 Sheet 3 of 33 US 8,993,540 B2 : S s N CO | 2 NN O. O. O. O. O. O. O. CN O OO Co V. CN V. V. (uffin) buoo oocuW U.S. Patent Mar. 31, 2015 Sheet 4 of 33 US 8,993,540 B2 FIG. 2A FIG. 2B FIG. 2C U.S. Patent Mar. 31, 2015 Sheet 5 Of 33 US 8,993,540 B2 U.S. Patent US 8,993,540 B2 I-LIOZUulu01-6IOZUuuu() U.S. Patent Mar. 31, 2015 Sheet 7 of 33 US 8,993,540 B2 Bacterial Quantity in Open Fracture Model 120% % Š O% % %S WA ZNo r 4A Sponge + Amikacin Bacterial Quantity in Open Fracture Model O% 2S 7 Mkrter 6pre 6post 48pre ZNo Treatment S.Chitosan Sponge + Vancomycin FIG. 4B U.S. Patent Mar. 31, 2015 Sheet 8 of 33 US 8,993,540 B2 Bacterial Quantity in Open Fracture Model 2.5OE--O5 2.OOE-05 15OE+05 1.OOE+05 5. OOE+04 O.OOE+OO 777N 6pre 6post 48pre Timepoint ZNo Treatment S.Ch. Sponge and Amikacin Bacterial Quantity in Open Fracture Model 8. OOE+O5 6.OOE+05 4.OOE+O5 2.OOE+05 ZEZN 1SNSN 6pre 6post 48pre ZNo Treatment S.Chitosan Sponge + Vancomycin FIG. 4D U.S. Patent Mar. 31, 2015 Sheet 9 Of 33 US 8,993,540 B2 Dr. s U.S. Patent Mar. 31, 2015 Sheet 10 of 33 US 8,993,540 B2 Da U.S. Patent Mar. 31, 2015 Sheet 11 of 33 US 8,993,540 B2 Ds s s s U.S. Patent Mar. 31, 2015 Sheet 12 of 33 US 8,993,540 B2 CIG'91-' U.S. Patent Mar. 31, 2015 Sheet 13 of 33 US 8,993,540 B2 E . O O 7 O 9 5g 32 z 2 8 H at .9 N s E CC N N l) V cy) CN O (uffin) ouoo 3oquw U.S. Patent Mar. 31, 2015 Sheet 15 of 33 US 8,993,540 B2 S5 i No &Sg 2%iNN > ŠS. 3.N Sg SN a S5 Z%NN Sg NZ O O 3 S s O U.S. Patent Mar. 31, 2015 Sheet 16 of 33 US 8,993,540 B2 cro CDOOO Film Variation DDA and AC id FIG. 9 U.S. Patent Mar. 31, 2015 Sheet 17 of 33 US 8,993,540 B2 1200 1000 Film Variation DDA and Acid FIG. 10 U.S. Patent Mar. 31, 2015 Sheet 18 of 33 US 8,993,540 B2 S N S. N N SN 2Z co ZZZZZ N Z v an O O O O O O O OO CO t CN s V (f6) ubsoluo I (u/5n) uoleuueouoo U.S. Patent Mar. 31, 2015 Sheet 19 Of 33 US 8,993,540 B2 s SN s N 2 N SN 2 so SN 2 co NN 2 - SN O O O O O O O O O O D O D O O O O v cy cy CN CN v- ve (f) uesoluo I (u/fu) uoeuueouoo U.S. Patent Mar. 31, 2015 Sheet 20 of 33 US 8,993,540 B2 FIG. 12 -Hydraulic xs- Grips N- Cylindrical Fixtures -- Chitosan Film U.S. Patent Mar. 31, 2015 Sheet 21 of 33 US 8,993,540 B2 N: l NS N %5 N & NN N to S CN O CO O V CN O v ve ve 2X U.S.
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