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New Type Cyanoacrylate Medical Adhesive And (19) *EP003335738B1* (11) EP 3 335 738 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61L 24/06 (2006.01) A61L 24/04 (2006.01) (2006.01) (2006.01) 06.11.2019 Bulletin 2019/45 A61L 15/24 C09J 133/14 A61L 24/00 (2006.01) (21) Application number: 15900803.6 (86) International application number: (22) Date of filing: 19.08.2015 PCT/CN2015/087551 (87) International publication number: WO 2017/024606 (16.02.2017 Gazette 2017/07) (54) NEW TYPE CYANOACRYLATE MEDICAL ADHESIVE AND PREPARATION METHOD AND USE THEREOF NEUARTIGER MEDIZINISCHER CYANACRYLATKLEBSTOFF UND HERSTELLUNGSVERFAHREN UND VERWENDUNG DAVON ADHÉSIF MÉDICAL DE CYANOACRYLATE DE NOUVEAU TYPE, ET PROCÉDÉ DE PRÉPARATION ET UTILISATION DE CE DERNIER (84) Designated Contracting States: • YU, Shufang AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Beijing 100176 (CN) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • WANG, Pengfei PL PT RO RS SE SI SK SM TR Beijing 100176 (CN) • SHAO, Jie (30) Priority: 11.08.2015 CN 201510489872 Beijing 100176 (CN) (43) Date of publication of application: (74) Representative: LLR 20.06.2018 Bulletin 2018/25 11, boulevard de Sébastopol 75001 Paris (FR) (73) Proprietor: Shen, Wei Beijing 100176 (CN) (56) References cited: WO-A1-02/09785 WO-A1-2015/059644 (72) Inventors: CN-A- 101 495 377 CN-A- 103 083 718 • SHEN, Wei CN-A- 104 710 953 US-A1- 2002 037 310 Beijing 100176 (CN) US-A1- 2002 037 310 US-A1- 2003 082 116 • XU, Jinghai Beijing 100176 (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 3 335 738 B1 Printed by Jouve, 75001 PARIS (FR) EP 3 335 738 B1 Description Technical field 5 [0001] The invention belongs to the technical field of biological material, and particularly relates to novel cyanoacrylate medical adhesive and preparation method and use thereof. Cyanoacrylate medical adhesive of the invention can be stored for a long time at room temperature, and can achieve rapid degradation and excellent user experience. Background technology 10 [0002] According to statistics, more than 4 million cases of surgery are performed every year in the world. The he- mostasis and antisepsis of the wound are key operations in surgery, especially when the operation need sew and ligate for repairing the tissue of organism. However, the operation is not only tedious, laborious, time-consuming, but also easy to cause new damage, bleeding and bring about more pain to the patient. For large areas of bleeding in which 15 bleeding spots can’t be found, doctors feel helpless, while the emergence of medical adhesive with fast hemostasis, sealing and adhesion functions provides a solution for solving the above problems. [0003] Medical adhesive generally refers to the cyanoacrylate tissue adhesive, which mechanism of action is thought of as anions polymerization in presence of trace anions in wound blood and tissue fluid, and the resulted elastic thin adhesive film which shows high tensile strength. The adhesive film is observed as a network structure under electron 20 microscope, which can effectively block the hemoglobin and platelet to achieve desired effect of hemostasis, adhesion and sealing. First cyanoacrylate adhesive on reported can be traced back to 1959, methyl cyanoacrylate (Eastman910) was developed by the United States Eastman Kodak company, and the product immediately attracted the attention of the medical profession for its instant adhesive property. Later homologous series of cyanoacrylate were synthesized including the ethyl cyanoacrylate, n-butyl cyanoacrylate, n-octyl cyanoacrylate, ethoxy ethyl cyanoacrylate, ethoxy butyl 25 cyanoacrylate, ethoxy octyl cyanoacrylate, butyl lactyl cyanoacrylate, isooctyl lactyl cyanoacrylate etc.. Cyanoacrylate adhesive shows some advantages, such as simple composition, easy use, fast solidification at room temperature, and high bonding strength, so it can be applied in many fields including the medical field. The cyanoacrylate medical adhesive has been widely used in clinic, including the main use field of adherence of incisions and wounds on the body surface, closed hemostasis of the body organ section as well as esophageal and fundal varices and vascular embolization. 30 [0004] The chemical structure of cyanoacrylate compounds commercially available at present can be expressed by formula I: 35 1) R can be a linear, branched or cyclic alkyl group with 1-20 carbon atoms; 40 or, 2) R can also be a group of formula -R2-O-R3, in which R2 and R3 are linear, branched or cyclic alkyl groups with 1-20 carbon atoms respectively and independently. or, 3) R can be a group of formula-R4-COO-R5, in which R4 and R5 are linear, branched or cyclic alkyl groups with 45 1-20 carbon atoms respectively and independently. [0005] According to different ester parts, the formula I cyanoacrylate compound can be divided into: 1) alkyl cyanoacr- ylate; 2) alkyl ether cyanoacrylate; 3) alkyl ester cyanoacrylate. Alkyl cyanoacrylate and alkyl ether cyanoacrylate products have the advantages of fast bonding rate and high bonding strength, but in clinical applications especially in vivo appli- 50 cations, these two products have their own shortcomings, namely the stable chemical property of formed polymer and the deficiency of enzymes for effectively decomposing the polymer, which lead to these two kinds of polymer present in the body for a long time as a foreign body (or implants) and bring some risk to the patient. The alkyl cyanoacrylate product also has the disadvantage of hard adhesive film. Compared with alkyl cyanoacrylate and alkyl ether cyanoacrylate, alkyl ester cyanoacrylate product is better in degradation and biological compatibility, especially faster in degradation 55 rate, and more secure in vivo medical uses, while the bonding rate and bonding strength of alkyl ester cyanoacrylate have weakness. [0006] In order to improve the degradation rate of alkyl cyanoacrylate, scientists both at home and abroad have done a lot of attempts. For example, the alkyl cyanoacrylate and alkyl ester cyanoacrylate were mixed in a certain proportion, 2 EP 3 335 738 B1 and two monomers were copolymerized in situ to form copolymers in practical application. Because polymer fragment of the alkyl ester cyanoacrylate provides a degradable part for copolymer, the degradation rate of the copolymer was greatly improved, and due to more excellent biocompatibility of alkyl ester cyanoacrylate, the product not only provides high bonding strength and good degradation rate, but also brings a better user experience. However, alkyl ester cy- 5 anoacrylate is very unstable, and is sensitive to acid and alkali and prone to hydrolysis for its lactyl structure, and hydrolysis products can further accelerate the polymerization of alkyl ester cyanoacrylate, so these products are very difficult to store for a long time at room temperature. Although low temperature facilities can be used to extend the storage period of alkyl ester cyanoacrylate medical adhesive, it will greatly increase the cost of production, storage and transportation, and will also bring additional risks. 10 [0007] US 2002/037310 discloses: an adhesive which can be used to treat animals, comprising: octyl cyanoacrylate (OCA); butyl ester cyanoacrylate (BLCA); in a range from 75:25 to 60:40 (weight ratio OCA:BLCA); sulfuric acid (25 to 100 ppm); sulfur dioxide (1 to 50 ppm); hydroquinone (960 to 1200 ppm) and butylated hydroxyanisole (500 to 800 ppm); ascorbic acid (100-15000ppm); reinforcing biodegradable polymers (PLGA). [0008] To sum up, the prior arts of cyanoacrylate medical adhesive have defects, in clinical, medical adhesive with 15 the features of a long-term storage, a rapid degradation rate, a rapid bonding rate, excellent bonding strength and excellent softness of adhesive film is needed. The purpose of the present disclosure is to provide cyanoacrylate medical adhesive which can be stored for a long time and has the features of a rapid degradation rate, a rapid bonding rate, excellent bond strength and softness of adhesive film. 20 Content of the invention Technical problems to be solved [0009] The purpose of the present disclosure is to provide cyanoacrylate medical adhesive which can be stored for a 25 long-term at room temperature and degrade rapidly in vivo. [0010] Another purpose of the present disclosure is to provide a method for preparing the cyanoacrylate medical adhesive. [0011] Another purpose of the present disclosure is to provide a use of the cyanoacrylate medical adhesive as a hemostatic material. 30 Technical solution [0012] The scope of the invention is defined by the claims. Any references in the description to methods of treatment refer to the products of the present invention for use in a method for treatment. 35 [0013] The disclosure is realized by the following technical solutions: Cyanoacrylate medical adhesive, wherein the medical adhesive is prepared by raw materials comprising the following components: a cyanoacrylate composition (A); and a composite stabilizer (C); wherein the cyanoacrylate composition (A) comprises the following components: 40 A1: an alkyl cyanoacrylate compound and/or alkyl ether cyanoacrylate compound, wherein the alkyl
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