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European Patent Office of Opposition to That Patent, in Accordance with the Implementing Regulations (19) TZZ ¥ _T (11) EP 2 792 372 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61L 24/00 (2006.01) A61L 24/04 (2006.01) 25.07.2018 Bulletin 2018/30 A61L 24/06 (2006.01) C08F 222/32 (2006.01) C09J 4/00 (2006.01) C09J 133/14 (2006.01) (2006.01) (21) Application number: 12846724.8 C09J 133/20 (22) Date of filing: 31.10.2012 (86) International application number: PCT/CN2012/083787 (87) International publication number: WO 2013/064059 (10.05.2013 Gazette 2013/19) (54) BIODEGRADABLE MEDICAL ADHESIVE AND PREPARATION METHOD AND USE THEREOF BIOLOGISCH ABBAUBARER MEDIZINISCHER HAFTSTOFF SOWIE VERFAHREN ZU SEINER HERSTELLUNG UND VERWENDUNG ADHÉSIF MÉDICAL BIODÉGRADABLE ET PROCÉDÉ DE PRÉPARATION ET D’UTILISATION ASSOCIÉ (84) Designated Contracting States: •XU,Liang AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Beijing 100850 (CN) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • ZHANG, Qingsong PL PT RO RS SE SI SK SM TR Chengdu Sichuan 610041 (CN) (30) Priority: 02.11.2011 CN 201110340675 • CAI, Dazhen Beijing 100850 (CN) (43) Date of publication of application: • MENG, Qingbin 22.10.2014 Bulletin 2014/43 Beijing 100850 (CN) (73) Proprietors: (74) Representative: Weickmann & Weickmann • Institute of Pharmacology and Toxicology PartmbB Academy of Military Medical Sciences P.L.A. Postfach 860 820 China 81635 München (DE) Beijing 100-850 (CN) • Chengdu Yiping Medical Science & (56) References cited: Technology Co., Ltd. EP-A1- 2 371 914 WO-A1-2009/064291 Chengdu, Sichuan 610041 (CN) WO-A2-2005/000985 CN-A- 1 272 797 US-A- 3 940 362 US-A- 4 041 063 (72) Inventors: US-A- 5 504 252 US-A- 6 096 848 • LIU, Keliang US-A1- 2005 245 966 Beijing 100850 (CN) 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 2 792 372 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 792 372 B1 Description TECHNICAL FIELD 5 [0001] The present invention relates to a medical adhesive, particularly to a biodegradable medical adhesive. The medical adhesive is biodegradable with non-toxic and absorbable degradation products. It can be used for skin wound adhesion, tissue adhesion, wound hemostasis and the like. BACKGROUND ART 10 [0002] The appearance of medical adhesive changes the concept of traditional medicine relying only on stitching wounds. The use of adhesion to replace or assist stitching not only has the advantages including simple operation and no secondary damage to wounds, but also can advantageously apply to or assist the application to soft tissues that are relatively difficult to stitch, for example, liver and pancreas, organs, bones and other parts. In addition, for large superfic ial 15 hemorrhage, abrasions, burns, battlefield injuries, field damage, intestinal leakage and the like, such medical adhesive can also form a protective film over wounds by means of coverage hemostasis, so as to achieve the purpose of hemostasis and prevention from external infection. [0003] Alkyl α-cyanoacrylate is the most widely used type of medical adhesive. In its structure, α carbon atom is linked to a cyano group and an ester group, so the double bond has a very low electron cloud density, and it has a very strong 20 electron-withdrawing property, and can generate instantaneous intermolecular polymerization under the action of infin- itesimal anions (amino group, hydroxyl group, trace weak basic material such as steam and the like on the surface of biological tissues). In general, alkyl α-cyanoacrylate as monomer is in liquid state, and, after being used by spraying or smearing to contact with human tissue, it rapidly polymerizes (less than 30 seconds) to cure, resulting in the desired adhesion or seal strength. In 1959, the first cyanoacrylate adhesive Eastman910 (methyl α-cyanoacrylate) was marketed 25 for skin adhesion and hemostasis. Subsequently, a number of cyanoacrylate adhesives were synthesized in various countries, for example, AU-CRYLATE (the main component thereof being n-/iso-butyl α-cyanoacrylate) in USA, HIS- TOACRYL BLUE (the main component thereof being n-butyl α-cyanoacrylate) in Germany. [0004] The research and production of medical adhesives have been carried out in China since 1962, mainly including FAL (n-butyl/n-octyl α-cyanoacrylate), butyl α-cyanoacrylate, isobutyl α-cyanoacrylate, n-octyl α-cyanoacrylate and the 30 like. These commercialized products have been widely used in clinical applications, but they still have some drawbacks. For example, the resulting polymer has relatively poor flexibility, and the resulting adhesive bond are relatively hard, which are unfavorable for the use in soft organs such as tissue and skin; the degradability is poor due to that single α- cyanoacrylate polymerizes to form a linear polymer, whose linear backbone chain obtained by polymerization of carbon- carbon double bond has a relatively high level of carbon-carbon bond energy, and is difficult to break, so this type of 35 polymer degrades very slowly, and the presence thereof at the wound site for a long time may lead to foreign body reaction, and may cause new inflammation and even impede further wound healing, to thereby reduce the practical value thereof as a surgical adhesive/sealant. [0005] Several patents reported modifications of the ester chain portion, including introduction of more ester linkage sites in the structure, to accelerate the degradation of side chain. U.S. Patent No. 3,995,641, as filed by Kronenthal et 40 al, discloses a carbalkoxyalkyl cyanoacrylate adhesive, which can form an absorbable polymer in mammalian tissue. Chinese patent CN101180085A discloses a cyanoacrylate structure containing a plurality of ester linkages and spacer groups in its side chain to accelerate degradation. EP 2 371 914 A1 describes an adhesive composition comprising a 2-cyanoacrylate and a polyfunctional cyanoacrylate having two or more 2-cyanoacryloyl groups which inter alia show a high thermal resistance for adhesive strength. 45 [0006] Although the modifications on side chain in these documents accelerate the degradation of side chain ester, these degradation modes, in fact, all deal with the degradation of the polymer side chain, while the linear carbon-carbon backbone chain of the polymer is still difficult to be degraded and absorbed. Thus, there is still a need to develop a medical adhesive whose polymer backbone chain has better biodegradability and biocompatibility. [0007] WO 2009/064291 A1 describes methods of accelerating degradation of a cyanoacrylate tissue adhesive by 50 blending polyethylene glycol with the cyanoacrylate. CONTENTS OF THE INVENTION [0008] The present invention relates to a type of medical adhesives which can undergo crosslinking copolymerization 55 and has good biodegradability. The biodegradability of the medical adhesives has been greatly improved as compared with the existing cyanoacrylate adhesives. [0009] Specifically, such type of crosslinked biodegradable medical adhesive is a multi-component mixture, wherein the polymer matrix includes two components or more components, i.e., at least comprising a mono- α-cyanoacrylate and 2 EP 2 792 372 B1 a bis-α-cyanoacrylic acid diol ester. The formulation of the polymer matrix can be described as follows: a medical adhesive, characterized in comprising: a mono- α-cyanoacrylate and a bis-α-cyanoacrylic acid diol ester; wherein in the medical adhesive the weight ratio of the mono-α-cyanoacrylate to the bis-α-cyanoacrylic acid diol ester is 1 : 1. [0010] Further, the alkyl mono-a-cyanoacrylate is at least one member selected from the group consisting of n-butyl 5 α-cyanoacrylate and n-octyl α-cyanoacrylate, and the bis-α-cyanoacrylic acid diol ester is bis-α-cyanoacrylic acid PEG2000 ester or the alkyl mono-α-cyanoacrylate is n-butyl α-cyanoacrylate and the bis-α-cyanoacrylic acid diol ester is bis-α-cyanoacrylic acid PEG600 ester. [0011] Optionally, the medical adhesive further comprises a pharmaceutically acceptable excipient. [0012] Also disclosed herein are structures of the mono- α-cyanoacrylate represented by Formula I: 10 15 wherein R1 is, but not limited to, straight and branched alkyl group having 1-30 carbon atoms, such as ethyl, n-butyl, n- octyl, iso-butyl, iso-octyl; straight and branched alkyl group having 1-30 carbon atoms substituted with acyloxy group, haloalkyl group, alkoxy group, halogen atom, cyano group and the like; straight and branched alkenyl group having 1-30 carbon atoms; straight and branched alkynyl group having 1-30 carbon atoms; cycloalkyl group, aralkyl group, alkylaryl 20 group, or aryl group, preferably n-butyl, n-octyl, iso-butyl, or iso-octyl. [0013] X can be an oxygen atom, or a nitrogen atom. X-R1 can also represent ethylene glycol group, polyethylene glycol (PEG) group, polyethylene glycol monomethyl ether (mPEG) group, amino PEG group and the like. [0014] The further disclosed structure of the bis-α-cyanoacrylic acid diol ester is represented by Formula II: 25 30 wherein X-R2-X represents a middle molecular fragment sandwiched between two α-cyano acryloyl moieties, whose molecular prototype is selected from the molecular structures that not only have good biocompatibility, but also are degradable in vivo, and have a wide application in the field of bio-medicine, food and the like, and it may be, but not limited to, small molecule diols, polyethylene glycol (PEG), amino PEG, polylactic acid (PLA), polyglycolic acid (PGA), lactic acid-glycolic acid copolymer (PLGA), copolymers containing polyhydroxy acid and polyglycol compounds such as 35 PLA-PEG-PLA block copolymers and PGA-PEG-PGA block copolymers, preferably PEG and small molecule diols.
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