WO2010058902A2 - Composition thermosensible prévenant l'adhérence au tissu et procédé de préparation de cette composition - Google Patents

Composition thermosensible prévenant l'adhérence au tissu et procédé de préparation de cette composition Download PDF

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Publication number
WO2010058902A2
WO2010058902A2 PCT/KR2009/005280 KR2009005280W WO2010058902A2 WO 2010058902 A2 WO2010058902 A2 WO 2010058902A2 KR 2009005280 W KR2009005280 W KR 2009005280W WO 2010058902 A2 WO2010058902 A2 WO 2010058902A2
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WIPO (PCT)
Prior art keywords
composition
tissue adhesion
adhesion preventing
thermosensitive
copolymer
Prior art date
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Ceased
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PCT/KR2009/005280
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English (en)
Korean (ko)
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WO2010058902A3 (fr
Inventor
최진석
이영우
이윤기
김준호
이진호
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BIORANE Co Ltd
Institute for Industry Academia Cooperation of Hannam University
Original Assignee
BIORANE Co Ltd
Institute for Industry Academia Cooperation of Hannam University
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Application filed by BIORANE Co Ltd, Institute for Industry Academia Cooperation of Hannam University filed Critical BIORANE Co Ltd
Priority to DK09827667.8T priority Critical patent/DK2366409T3/en
Priority to EP09827667.8A priority patent/EP2366409B1/fr
Priority to CN200980149694.2A priority patent/CN102245212B/zh
Priority to ES09827667.8T priority patent/ES2526453T3/es
Priority to US13/129,765 priority patent/US9095643B2/en
Priority to PL09827667T priority patent/PL2366409T3/pl
Priority to JP2011537345A priority patent/JP5604440B2/ja
Publication of WO2010058902A2 publication Critical patent/WO2010058902A2/fr
Publication of WO2010058902A3 publication Critical patent/WO2010058902A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/04—Macromolecular materials
    • A61L31/041—Mixtures of macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to a thermally sensitive tissue adhesion preventing composition and a method for manufacturing the same, and more particularly, a block copolymer containing a polyethylene oxide block having a tissue adhesion inhibiting ability and a molecular weight of 10,000 to 1,000,000 g that can be mixed with the copolymer. It is prepared by adding a crosslinking agent to an aqueous solution containing a polymer / mol to cause a chemical reaction, and further comprises a drug that can selectively inhibit the inflammatory reaction, when the composition is centrifuged, the supernatant and the lower layer solution
  • the present invention relates to a thermosensitive tissue adhesion preventing composition, wherein the difference in viscosity, absorbance and stability in the visible light region is within 10%. Simultaneous crosslinking and viscosity stability by using simultaneous method It relates to a method for producing a thermosensitive tissue adhesion preventing composition, characterized in that.
  • Adhesion occurs after various surgeries.Adhesion occurs when blood is leaked and coagulates during wound healing, such as inflammation, wound, friction, and wound caused by surgery, whereby primary adhesion with surrounding organs or tissues occurs. Is penetrated and organized to form stronger adhesions. Adhesion to the pelvis may cause chronic pain, sexual dysfunction, or infertility, and side effects such as chest pain and decreased swallowing ability may occur due to scar formation after thyroid removal. In the case of adhesions, the nerves are compressed, causing severe pain. Therefore, secondary surgery is required to remove these adhesions, which is a huge economic burden. According to the US statistics in 1988, the cost of treating the complications of adhesions after abdominal surgery was 12 It has been reported to reach billions of dollars.
  • adhesion occurs to the endometrium in 20 to 50% after curettage or suction evacuation for incomplete miscarriage, stillbirth, recurrent miscarriage, etc.
  • many studies have been conducted to prevent adhesion.
  • a method of using a physical barrier has been developed and used.
  • Polyethyleneglycol-polypropyleneglycol-polyethyleneglycol (PEG-PPG-PEG) block copolymers change in viscosity in response to environmental stimuli such as acidity, temperature, ionic strength, etc. It is well known that the state changes with respect to isothermal, and the techniques used for medical materials using it are described in US Pat. Nos. 5,939,485, 4,188,373, 4,478,822, 4,474,751, and the like.
  • Korean Patent Application No. 10-2003-0050953 discloses a mixture of Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ in order to crosslink a polymer that gives proper viscosity and stability in aqueous solution.
  • High speed stirrer for crosslinking using at least one selected from cations or chitosan, glutaraldehyde, formalin, poly-L-lysine Although used, a large amount of fibrous suspended solids is produced, and the resulting suspended solids is difficult to remove and uniform crosslinking is difficult.
  • sodium carbonate Na 2 CO 3
  • trisodium phosphate Na 3 PO 4
  • trisodium phosphate Na 3 PO 4 12H 2 O
  • sodium polyphosphate which are ion exchange polymerization rate retarders (Na 5 P 3 O 10)
  • exhaustion of Crataegus sodium Na 4 P 2 O 7
  • leading fatigue of Crataegus sodium Na 4 P 2 O 7 10H 2 O
  • leading ethylenediaminetetraacetic second Crataegus sodium Na 4 EDTA2H 2 O
  • thermosensitive tissue adhesion inhibitor which can increase the uniformity of the crosslinking and the stabilization of the viscosity.
  • the present invention is an aqueous solution containing a block copolymer containing a polyethylene oxide block having a biocompatibility and excellent tissue adhesion inhibitory performance and a polymer imparting appropriate viscosity and stability in an aqueous solution. It is prepared by adding a crosslinking agent to cause a chemical reaction, and further comprises a drug that can selectively inhibit the inflammatory reaction can be easily applied to the wound site in the human body, and excellent heat sensitive tissue adhesion prevention composition excellent tissue adhesion prevention performance It aims to provide.
  • the present invention when preparing the thermally sensitive tissue adhesion prevention composition, by using a spray method and a stirring method at the same time without adding a reaction rate retardant to prevent the thermally sensitive tissue adhesion that can increase the uniformity of the crosslinking and the stability of the viscosity Provided are methods for preparing the composition.
  • the composition When the composition is centrifuged at 25 ° C. at 3,000 rpm for 3 minutes, the difference between the viscosity of the supernatant and the lower layer, the absorbance of the visible region and the stability is within 10%. do.
  • the total surface area of the crosslinking agent may be maximized using a spray method to prevent fibrous suspensions caused by uneven crosslinking even when the rate retardant is not added.
  • Comparative Example 1 is a diagram showing a manufacturing method of Comparative Example 1 of the present invention.
  • Comparative Example 2 is a diagram showing a manufacturing method of Comparative Example 2 of the present invention.
  • FIG 3 shows Examples 1 to 4 of the present invention. Figure showing the manufacturing method of.
  • the present invention is a block copolymer containing a polyethylene oxide block having a molecular weight of 1,000 to 500,000 g / mol, dissolved in an aqueous solution to exhibit a sol-gel transition and inhibit tissue adhesion according to the temperature in order to achieve the above object and the It is prepared by adding a crosslinking agent to an aqueous solution containing a polymer having a molecular weight of 10,000 to 1,000,000 g / mol to give a suitable viscosity (3,000 to 9,000 cP) and stability in an aqueous solution by mixing with a copolymer, the composition is 25 It provides a thermosensitive tissue adhesion preventing composition, characterized in that the difference between the viscosity of the supernatant and the lower layer solution, the absorbance and stability of the visible region within 10% when centrifuged at 3,000 rpm for 3 minutes at? May optionally also comprise a drug, in particular an anti-inflammatory agent.
  • the block copolymer containing the polyethylene oxide block has a molecular weight of 1,000 to 500,000 g / mol, polyethylene oxide-polypropylene oxide copolymer (Pluronic series), polyethylene oxide-polylactic acid copolymer, polyethylene oxide-polylactic glycolic acid Copolymers, polyethylene oxide-polycaprolactone copolymers, and the like can be used.
  • the polymer having a molecular weight of 10,000 to 1,000,000 g / mol includes chondroitin sulfate, dermatan sulfate, keratan sulfate, heparan sulfate, alginic acid, hyaluronic acid, and carboxymethyl cellulose which are a kind of glycosaminoglycan.
  • One or more mixtures selected from the group consisting of loose, dextran, collagen, and their degradation products gelatin, elastin, and fibrin can be used.
  • the crosslinking agent includes at least one cation selected from Mg 2+ , Mn 2+ , Ca 2+ , Co 2+ , Cu 2+ , Sr 2+ , Ba 2+ , Fe 2+ , Co 2+ .
  • thermosensitive tissue adhesion preventing composition according to the present invention is a block copolymer containing the polyethylene oxide block and the polymer is produced through a chemical bond, the chemical bond is graft copolymerization, random copolymerization, cross copolymerization, crosslinking, etc. It can be combined.
  • the drugs include thrombin, aprotinin, steroid (Steroidal Anti-Inflammatory Drug) and nonsteroidal anti-inflammatory drugs (NSAIDs, Non Steroidal Anti-Inflammatory Drug), heparin, tissue plasma Minogen activators and anti-inflammatory agents (Ibuprofen, Naproxen, Tolmetin, Indomethacin) and the like can be used.
  • the drug may be included in the composition during the preparation of the tissue anti-adhesion composition according to the present invention or before application to the wound, and the drug is released by gelling the anti-adhesion composition by body temperature.
  • the drug By preparing a tissue adhesion preventing composition by further including the drug, in particular, an anti-inflammatory agent, the drug may be released or the inflammatory response may be suppressed to further improve the tissue adhesion inhibiting ability.
  • any one of saline solution including saline and phosphate buffer solution, organic acid salt buffer solution, bicarbonate buffer solution, and the like may be selected and used. This is because it is a solution that is superior in biocompatibility than the composition prepared using pure water. In particular, when using a salt solution can be lowered the temperature to gel than the composition prepared using pure water, it is also possible to increase the speed of thermal response.
  • Block containing polyethylene oxide block for the composition according to the present invention (hereinafter referred to as 'composition according to the present invention') formed from the block copolymer containing the polyethylene oxide block, the polymer and the crosslinking agent.
  • the content of the copolymer is preferably 1 to 50% by weight, more preferably 10 to 30% by weight. If the content is less than 1% by weight, there is a problem that the sol-gel transition does not appear. If the content is more than 50% by weight, the viscosity of the sample is high and it is difficult to apply the body at room temperature.
  • the content of the polymer in the composition according to the present invention is preferably 0.1 to 4% by weight, more preferably 0.5 to 1% by weight. If the content is less than 0.1% by weight, there is a problem in that it does not provide viscosity or stability or crosslinking, and when the content exceeds 4% by weight, the viscosity of the sample is high, so that uniform application in the body is difficult.
  • the content of the crosslinking agent in the composition according to the present invention is preferably 0.01 to 2% by weight, more preferably 0.05 to 0.2% by weight. If the content is less than 0.01% by weight, there is a problem in that crosslinking cannot be formed. If the content is more than 2% by weight, strong crosslinking is formed and the sample does not have flowability.
  • the content of the composition according to the present invention is preferably 0.01 to 50% by weight, particularly in the case of an anti-inflammatory agent, the content is more preferably 1 to 10% by weight. If less than 0.01% by weight, there is a problem that does not exhibit the effect of inhibiting inflammation and anti-adhesion, and if it exceeds 50% by weight, there is a problem of showing toxicity in the human body.
  • thermosensitive tissue adhesion preventing composition according to the present invention When the thermosensitive tissue adhesion preventing composition according to the present invention is centrifuged for 3 minutes at 25 ° C. at 3,000 rpm using a centrifugal separator, the difference between the viscosity of the supernatant and the lower layer, the absorbance and stability of the visible region is different. It may be within 10%, preferably within 7%, and more preferably within 5%.
  • the viscosity was measured at 20 ° C. in the sol state, and the absorbance was measured in the wavelength range of 400 to 750 in the visible range. The shape maintenance of the state was confirmed.
  • the above-described block copolymer containing a polyethylene oxide block having a tissue adhesion inhibiting ability according to the present invention and a polymer that gives viscosity and stability in an aqueous solution together with the copolymer is uniformly mixed, and optionally a drug is added.
  • the anti-tissue adhesion composition prepared by the present invention can be injected and applied very easily and evenly to any complex wound site and has stability, and thus can be applied very effectively as an anti-adhesion agent because it shows excellent tissue adhesion prevention performance.
  • the spraying rate is preferably 10 to 100 ml / min, more preferably 50 to 100 ml / min on the aqueous solution. Can be.
  • the crosslinking agent may be spray-sprayed in the range of 5 to 500 ⁇ m, preferably 50 to 100 ⁇ m, in spray spray particle diameter.
  • the stirring speed in the aqueous solution is preferably 300 rpm to 1500 rpm, and more preferably 500 to 1,000 rpm. If the stirring speed is less than 300rpm it is easy to partial stirring rather than the overall stirring.
  • a polyethylene oxide-polypropylene oxide copolymer according to the present invention is a polyethylene oxide-polypropylene oxide copolymer capable of inhibiting biocompatibility, sol-gel phase transition and tissue adhesion in an aqueous solution of 0.8% by weight of hyaluronic acid, which is a natural polymer and has excellent biocompatibility. 25 wt% of the composition was added, and an anti-adhesion composition was prepared by adding Ca (CH 3 COO) 2 aqueous solution without any device while stirring at 500 rpm using a stirrer.
  • a polyethylene oxide-polypropylene oxide copolymer according to the present invention is a polyethylene oxide-polypropylene oxide copolymer capable of inhibiting biocompatibility, sol-gel phase transition and tissue adhesion in an aqueous solution of 0.8% by weight of hyaluronic acid, which is a natural polymer and has excellent biocompatibility. 25 wt% of the composition was added, and an anti-adhesion composition was prepared by adding Ca (CH 3 COO) 2 aqueous solution by 20 ml / min using a burette while stirring at 500 rpm using a stirrer.
  • a polyethylene oxide-polypropylene oxide copolymer capable of inhibiting biocompatibility and sol-gel phase transition and tissue adhesion is contained in an aqueous solution of 0.8% by weight of hyaluronic acid, which is a natural polymer and has excellent biocompatibility. 25 wt% of the composition was added, and an anti-adhesion composition was prepared by spraying Ca (CH 3 COO) 2 aqueous solution by 20 ml / min using a spray while stirring at 500 rpm using a stirrer.
  • a polyethylene oxide-polypropylene oxide copolymer according to the present invention is a polyethylene oxide-polypropylene oxide copolymer capable of inhibiting biocompatibility, sol-gel phase transition and tissue adhesion in an aqueous solution of 0.8% by weight of hyaluronic acid, which is a natural polymer and has excellent biocompatibility. 25 wt% of the composition was added, and an anti-adhesion composition was prepared by spraying an aqueous solution of CaCl 2 at 20 ml / min using a spray while stirring at 500 rpm using a stirrer.
  • the composition according to the present invention is a polyethylene oxide-polypropylene oxide copolymer which is a natural polymer and has excellent biocompatibility, and can inhibit biocompatibility, sol-gel phase transition and tissue adhesion in an aqueous solution of 0.8% by weight of ultrapure water. It was added to 25% by weight, and while stirring at a speed of 500rpm using a stirrer Ca (CH 3 COO) 2 aqueous solution was sprayed at 20ml / min using a spray to prepare an anti-adhesion composition.
  • the composition according to the present invention is a polyethylene oxide-polypropylene oxide copolymer which is a natural polymer and has excellent biocompatibility, and can inhibit biocompatibility, sol-gel phase transition and tissue adhesion in an aqueous solution of 0.8% by weight of ultrapure water. It was added to 25% by weight, and while stirring at a speed of 500rpm using a stirrer while spraying CaCl 2 aqueous solution 20ml / min using a spray to prepare an anti-adhesion composition.
  • the tissue adhesion preventing compositions of Comparative Examples 1, 2 and 1 to 4 prepared by the above method were centrifuged at 3,000 rpm for 3 minutes at 25 ° C. using a centrifugal separator, and then the supernatant and The results obtained by measuring the viscosity, absorbance, and stability of the visible light region separated from the lower layer solution are shown in Tables 1, 2, and 3, respectively.
  • Table 1 shows the viscosity difference by dividing the material prepared in Comparative Examples 1, 2 and Examples 1 to 4 of the present invention into a supernatant portion and a lower layer portion using a centrifuge.
  • Table 2 shows the absorbance of the visible light region by dividing the material prepared in Comparative Examples 1, 2 and Examples 1 to 4 of the present invention into a supernatant portion and a lower layer portion using a centrifuge.
  • Table 3 shows the stability of the materials prepared in Comparative Examples 1, 2 and Examples 1 to 4 of the present invention by dividing the material into a supernatant portion and a lower layer portion using a centrifuge.
  • the tissue adhesion preventing composition of Examples 1 to 4 prepared by injecting a crosslinking agent using a spray method the viscosity of the supernatant and the lower layer solution compared to Comparative Examples 1 and 2 without the spray method Is similar, the difference is within 10%, it can be seen that the stability is better.

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Abstract

La présente invention concerne une composition thermosensible prévenant l'adhérence au tissu et un procédé de préparation de cette composition. Plus spécifiquement, la présente invention concerne une composition thermosensible prévenant l'adhérence au tissu qui contient aussi un médicament qui inhibe sélectivement une réponse inflammatoire, et un procédé de préparation de cette composition. La composition est fabriquée par réaction chimique par l'addition d'un agent de réticulation à une solution aqueuse. Cette solution aqueuse contient : un copolymère bloc contenant un bloc polyéthylèneoxyde possédant la capacité de supprimer l'adhérence au tissu, et un polymère d'un poids moléculaire compris entre 10,000 et 1,000,000 g/mol qui peut être mélangé avec ce copolymère. Cette composition se caractérise aussi en ce que les différences de viscosité, d'absorbance de région visible, et de stabilité entre les couches supérieure et inférieure liquides sont inférieures ou égale à 10% lors de la centrifugation de la composition. De plus, le procédé de préparation de cette composition améliore l'homogénéisation de réticulation et la stabilité de viscosité par des procédés de pulvérisation et de malaxage simultanés sans retardant de réaction. Selon la présente invention, des débris flottants sur une fibre causés par une réticulation non uniforme peuvent non seulement être empêchés, mais l'homogénéisation de réticulation et la stabilisation de viscosité peuvent aussi être améliorées. Par conséquent, cette composition peut être uniformément appliquée sur une blessure d'une personne et elle possède une haute stabilité et d'excellents effets pour empêcher l'adhérence au tissu.
PCT/KR2009/005280 2008-11-19 2009-09-17 Composition thermosensible prévenant l'adhérence au tissu et procédé de préparation de cette composition Ceased WO2010058902A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DK09827667.8T DK2366409T3 (en) 2008-11-19 2009-09-17 Thermosensitive composition as PREVENTING tissue adhesion AND MANUFACTURING METHOD THEREOF
EP09827667.8A EP2366409B1 (fr) 2008-11-19 2009-09-17 Composition thermosensible prévenant l'adhérence au tissu et procédé de préparation de cette composition
CN200980149694.2A CN102245212B (zh) 2008-11-19 2009-09-17 防止组织粘连的热敏组合物及其制造方法
ES09827667.8T ES2526453T3 (es) 2008-11-19 2009-09-17 Composición termosensible que previene la adhesión de los tejidos y método para su preparación
US13/129,765 US9095643B2 (en) 2008-11-19 2009-09-17 Composition preventing tissue adhesion and preparation method thereof
PL09827667T PL2366409T3 (pl) 2008-11-19 2009-09-17 Termowrażliwa kompozycja zapobiegająca zrastaniu się tkanek i sposób jej wytwarzania
JP2011537345A JP5604440B2 (ja) 2008-11-19 2009-09-17 熱感応性組織癒着防止用組成物およびその製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2008-0114946 2008-11-19
KR1020080114946A KR101125934B1 (ko) 2008-11-19 2008-11-19 열감응성 조직 유착 방지 조성물 및 이의 제조 방법

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WO2010058902A2 true WO2010058902A2 (fr) 2010-05-27
WO2010058902A3 WO2010058902A3 (fr) 2010-07-15

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PCT/KR2009/005280 Ceased WO2010058902A2 (fr) 2008-11-19 2009-09-17 Composition thermosensible prévenant l'adhérence au tissu et procédé de préparation de cette composition

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US (1) US9095643B2 (fr)
EP (1) EP2366409B1 (fr)
JP (1) JP5604440B2 (fr)
KR (1) KR101125934B1 (fr)
CN (1) CN102245212B (fr)
DK (1) DK2366409T3 (fr)
ES (1) ES2526453T3 (fr)
PL (1) PL2366409T3 (fr)
PT (1) PT2366409E (fr)
WO (1) WO2010058902A2 (fr)

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WO2013015579A2 (fr) * 2011-07-26 2013-01-31 (주)차바이오앤디오스텍 Matériau composite organique médical comprenant du collagène et des dérivés d'acide hyaluronique
KR101330652B1 (ko) 2012-02-28 2013-11-18 (주)시지바이오 성장인자 담지 가능한 유착방지용 고분자 조성물
KR101389831B1 (ko) * 2012-05-25 2014-05-07 한남대학교 산학협력단 온도 감응형 유착방지제
US20150209481A1 (en) * 2012-08-16 2015-07-30 Nipro Corporation Antiadhesive Material
CN104027850A (zh) * 2014-06-03 2014-09-10 陈凯 一种术后冲洗剂及其制备方法
KR101627787B1 (ko) * 2014-07-24 2016-06-07 주식회사 메디톡스 열감응성 유착 방지용 조성물 및 그의 용도
PL409231A1 (pl) * 2014-08-21 2016-02-29 Warszawski Uniwersytet Medyczny Sposób wytwarzania gwoździ śródszpikowych z chitozanu do leczenia złamań kości długich
KR101852718B1 (ko) 2017-04-04 2018-05-18 주식회사 제네웰 외과수술 후 절개부위 통증 감소를 위한 키트
KR101923734B1 (ko) 2017-04-13 2018-11-29 영남대학교 산학협력단 유착 방지용 가교 필름
KR101981562B1 (ko) * 2017-05-04 2019-05-24 주식회사 테라시온 바이오메디칼 유착방지용 조성물의 제조방법
CN108159508B (zh) * 2018-01-03 2021-01-26 东南大学 一种防粘连医用水凝胶材料的制备方法
KR101902956B1 (ko) 2018-03-13 2018-10-02 주식회사 제네웰 외과수술 후 절개부위 통증 감소를 위한 키트
KR102065016B1 (ko) 2018-04-17 2020-01-10 주식회사 제네웰 외과수술 후 절개부위 통증 감소 또는 치료를 위한 키트
KR102144479B1 (ko) * 2018-05-24 2020-08-13 주식회사 덱스레보 조직 수복용 조성물 및 이의 제조방법
KR102251192B1 (ko) * 2020-08-07 2021-05-13 주식회사 덱스레보 조직 수복용 조성물 및 이의 제조방법
CN117618533B (zh) * 2023-11-28 2024-08-06 上海市第四人民医院 一种光敏固化喷剂及其制备方法和应用
CN120899734B (zh) * 2025-08-08 2026-04-21 湖南科迈森医疗科技有限公司 一种基于黄芪甲苷和丹酚酸b的壳聚糖-透明质酸水凝胶组合物、制备方法及应用

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US9095643B2 (en) 2015-08-04
EP2366409B1 (fr) 2014-12-10
CN102245212B (zh) 2014-06-18
JP2012509129A (ja) 2012-04-19
PT2366409E (pt) 2015-01-13
DK2366409T3 (en) 2015-01-12
KR101125934B1 (ko) 2012-03-21
KR20100056009A (ko) 2010-05-27
CN102245212A (zh) 2011-11-16
ES2526453T3 (es) 2015-01-12
JP5604440B2 (ja) 2014-10-08
EP2366409A2 (fr) 2011-09-21
EP2366409A4 (fr) 2013-07-31
PL2366409T3 (pl) 2015-03-31
US20110229432A1 (en) 2011-09-22

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