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Antimicrobial Silver-Containing Biomaterials Antimikrobielle Silberhaltige Biomaterialien Biomatériaux Antimicrobes Contenant De L’Argeant

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Antimicrobial Silver-Containing Biomaterials Antimikrobielle Silberhaltige Biomaterialien Biomatériaux Antimicrobes Contenant De L’Argeant (19) TZZ ¥_T (11) EP 2 464 236 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 37/36 (2006.01) A01N 61/00 (2006.01) 16.10.2019 Bulletin 2019/42 A01N 59/16 (2006.01) A01N 43/16 (2006.01) A01N 47/44 (2006.01) A01N 31/16 (2006.01) (2006.01) (2006.01) (21) Application number: 10808706.5 A01N 25/34 A61K 31/202 A61K 31/232 (2006.01) A61K 31/765 (2006.01) A61K 31/09 (2006.01) A61K 31/155 (2006.01) (22) Date of filing: 11.08.2010 A61K 31/35 (2006.01) A61K 31/28 (2006.01) A61L 29/16 (2006.01) A61L 31/16 (2006.01) A61L 15/44 (2006.01) A01P 1/00 (2006.01) A61K 33/38 (2006.01) A61K 45/06 (2006.01) (86) International application number: PCT/US2010/045194 (87) International publication number: WO 2011/019834 (17.02.2011 Gazette 2011/07) (54) ANTIMICROBIAL SILVER-CONTAINING BIOMATERIALS ANTIMIKROBIELLE SILBERHALTIGE BIOMATERIALIEN BIOMATÉRIAUX ANTIMICROBES CONTENANT DE L’ARGEANT (84) Designated Contracting States: • MARTAKOS, Paul AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Pelham GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO NH 03076 (US) PL PT RO SE SI SK SM TR (74) Representative: Helbig, Christian et al (30) Priority: 11.08.2009 US 539282 Wagner + Helbig Patentanwälte (43) Date of publication of application: Pfarrstrasse 14 20.06.2012 Bulletin 2012/25 80538 München (DE) (73) Proprietor: Atrium Medical Corporation (56) References cited: Hudson, NH 03051 (US) WO-A1-2009/091900 WO-A1-2010/042241 US-A1- 2006 110 457 US-A1- 2006 204 738 (72) Inventors: US-A1- 2006 263 330 US-A1- 2008 109 017 • FAUCHER, Keith, M. US-A1- 2009 181 937 Milford NH 03055 (US) • ZHENG ET AL: "Fatty acid synthesis is a target • KABIRU, Hilda for antibacterial activity of unsaturated fatty Nashua acids", FEBS LETTERS, ELSEVIER, NH 03062 (US) AMSTERDAM, NL, vol. 579, no. 23, 26 September • HORTON, Anthony, Richard 2005 (2005-09-26), pages 5157-5162, Manchester XP005390460, ISSN: 0014-5793, DOI: NH 03104 (US) 10.1016/J.FEBSLET.2005.08.028 • PROWSE, Jocelyn Waltham MA 02453 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 464 236 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 2 464 236 B1 • JI-YOUNGLEE ET AL: "AntimicrobialSynergistic • MULTANEN M ET AL: "Bacterial adherence to Effect of Linolenic Acid and Monoglyceride silver nitrate coated poly-L-lactic acid urological against Bacillus cereus and Staphylococcus stents in vitro", UROLOGICAL RESEARCH, aureus", JOURNAL OF AGRICULTURAL AND SPRINGER VERLAG, BERLIN, DE, vol. 28, no. 5, FOOD CHEMISTRY, vol. 50, no. 7, 1 March 2002 1 October 2000 (2000-10-01), pages 327-331, (2002-03-01), pages 2193-2199, XP055072182, XP002451300, ISSN: 0300-5623, DOI: ISSN: 0021-8561, DOI: 10.1021/jf011175a 10.1007/S002400000133 2 1 EP 2 464 236 B1 2 Description formation of adhesions (Y.C. Cheong et al., 2001). Ab- dominal adhesions formed after hernia repair can result RELATED APPLICATION(S) in pain, bowel strangulation, infertility and in some cases death (Y.C. Cheong et al., 2001). [0001] This application claims priority to, and the ben- 5 [0005] U.S. Patent Application Publication No. US efit of, U.S. Application No. 12/539,282, filed on August 2009/0181937 A1 (Faucher et al.) discloses cross-linked 11, 2009. fatty acid-based biomaterials that may be used alone or in combination with a medical device for the release and BACKGROUND OF THE INVENTION local delivery of one or more therapeutic agents. How- 10 ever, this document does not pertain to an antimicrobial [0002] Implantable medical devices are indispensable silver hydrated fatty acid-derived biomaterial comprising in the ability to treat a variety of medical onditionsc in a fatty acid and a glyceride that is hydrated with an aque- critically and chronically ill patients. Catheters can be ous form of silver to form silver fatty acid salts within the used to deliver drugs or nutrients to a patient or to safely biomaterial. remove waste products. Stents can be used to open15 [0006] WO 2009/091900 A1 (John et al.) discloses a blocked coronary arteries and restore blood flow to the green approach in metal nanoparticle-embedded antimi- heart. Vascular grafts can also be used to restore blood crobial coatings from vegetable oils and oil-based mate- flow in addition to providing easier access and improved rials, which relates to methods of making metal nanopar- treatment of a patient with kidney failure by dialysis. Her- ticles. However, this document does not disclose the for- nia mesh devices allow for improved patient outcomes 20 mation of an antimicrobial silver hydrated fatty acid-de- in the treatment of abdominal wounds by providing ad- rived biomaterial comprising a fatty acid and a glyceride ditional strength to the surgical repair. that is hydrated with an aqueous form of silver to form [0003] Onecomplication in the use of implantable med- silver fatty acid salts within the biomaterial. ical devices is the risk of these devices becoming colo- [0007] WO 2010/042241 A1 (Faucher et al.) discloses nized with bacteria during surgical implantation (see,25 cross-linked fatty acid-based biomaterials such as per- e.g., A.M. Carbonell et al. Surg Endosc. 2005; Vol. 19, tain to fatty acid-based, pre-cure-derived biomaterials. pgs 430-435; T. Bechert et al. Nature Medicine. 2000; However, this document does not disclose the formation Vol. 6, No. 8, pgs 1053-1056; R. Kuijer et al. Biomaterials. of an antimicrobial silver hydrated fatty acid-derived bi- 2007; Vol. 28, pgs 5148-5154; C.R. Arciola et al. Bioma- omaterial comprising a fatty acid and a glyceride that is terials. 2008; Vol. 29, pgs 580-586). Once a patient30 hydrated with an aqueous form of silver to form silver shows signs of device infection, the surgeon is often re- fatty acid salts within the biomaterial. quired to perform several additional surgical procedures [0008] U.S. Patent Application Publication No. US to treat the device infection, such as drainage of the in- 2006/0263330 A1 (Emeta et al.) discloses antimicrobial fection site and the local administration of antibiotics. In polymer compositions and their uses. However, the dis- cases where the infection is not successfully resolved, 35 closed antimicrobial polymer compositions include a the surgeon will be required to remove the device from complex of an anionic polyester with an antimicrobial the implanted surgical site until the infection is resolved metal, wherein the anionic polyester has at least one car- with the treatment of oral and/or intravenous antibiotics boxylic acid group. These materials may be immersed in to the patient. Thus, an infected medical device not only a silver salt solution so as to form a complex of anionic results in increasing medical costs, but also results in 40 polyester and silver. However, these materials are sub- increased risk of morbidity and mortality to the patient stantially different from an antimicrobial silver hydrated (A.M. Carbonell et al., 2005; T. Bechert et al, 2000; R. fatty acid-derived biomaterial comprising a fatty acid and Kuijer et al., 2007). a glyceride. [0004] Another important aspect in the use of medical [0009] M. Multanen et al., Bacterial adherence to silver devices is the biological response to a medical device 45 nitrate coated poly-L-lactic acid urological stents in vitro, after surgical repair of an in-vivo injury (see,e.g., Y.C. 38 UROLOGY RESEARCH 327-31 (2000) pertains to a Cheong et al. Human Reproduction Update. 2001; Vol. studydirected to whether it is possible toprevent bacterial 7, No. 6, pgs 556-566). A typical biological response to adherence to bioabsorbable self-reinforced L-lactic acid the surgical site includes inflammation of native tissue polymer (SR-PLLA) urological stents by coating these followed by migration and proliferation of cells to mitigate 50 stents with silver nitrate blended epsilon-captrolac- the inflammatory response, including platelets and mac- tone/L-lactide copolymer. This document reports that the rophages, and a subsequent healing phase that includes studied silver nitrate coating prevented adherence of fibrin deposition and the formation of fibrin matrix fol- some bacteria to the SR-PLLA stents. However, the stud- lowed by tissue remodeling. In the case of hernia repair, ied materials are substantially different from an antimi- abnormal peritoneal healing can occur when there is the 55 crobial silver hydrated fatty acid-derived biomaterial expression of inflammatory cytokines from macrophages comprising a fatty acid and a glyceride. (e.g., α-TNF) that can result in an inability of the fibrin [0010] Accordingly, there remains a need for medical matrix to be properly broken down and can result in the devices that have a reduced susceptibility to colonization 3 3 EP 2 464 236 B1 4 by bacteria and other microorganisms, or other health and cresol. complications, such as adhesions. [0015] In another aspect disclosed herein, the antimi- crobial compound is an antibiotic compound. The antibi- SUMMARY OF THE INVENTION otic compound can be selected from the group consisting 5 of gentamicin sulfate, penicillin g, ephalothin, ampicillin, [0011] What is desired is a material ( e.g.,a device coat- amoxicillin, augmentin, aztreonam, imipenem, strepto- ing, gel or stand-alone film) that can be utilized to prevent mycin,gentamicin, vancomycin,clindamycin, erythromy- or diminish chronic inflammation due to the hydrolysis cin, azithromycin, polymyxin, bacitracin, amphotericin, products of the coating, as well as to reduce infection nystatin, rifampicin, tetracycline, doxycycline, chloram- resulting from surgical implantation of medical devices.
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