WO2021090997A1 - Éponge d'acide hyaluronique photo-réticulé et son procédé de fabrication - Google Patents

Éponge d'acide hyaluronique photo-réticulé et son procédé de fabrication Download PDF

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WO2021090997A1
WO2021090997A1 PCT/KR2019/015909 KR2019015909W WO2021090997A1 WO 2021090997 A1 WO2021090997 A1 WO 2021090997A1 KR 2019015909 W KR2019015909 W KR 2019015909W WO 2021090997 A1 WO2021090997 A1 WO 2021090997A1
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hyaluronic acid
anhydride
photo
compound represented
chemical formula
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PCT/KR2019/015909
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English (en)
Korean (ko)
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박삼대
양승윤
박수영
황영준
정세민
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주식회사 에스엔비아
부산대학교 산학협력단
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Publication of WO2021090997A1 publication Critical patent/WO2021090997A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof

Definitions

  • the present invention relates to a light-crosslinked hyaluronic acid sponge and a method for manufacturing the same, and more specifically, it can be used on various parts of the body because it does not have stickiness and dripping, and it has excellent water binding power to help tissue regeneration. It has excellent suitability, so it is absorbed into the skin when it is attached to the body for a long time, so it can reduce the troubles that need to be removed, and the photo-crosslinking reaction includes a polymer of various lengths, including a porous medical hemostatic agent, wound coating, and adhesion prevention.
  • the present invention relates to a photo-crosslinkable hyaluronic acid sponge that is also usefully utilized as zero and a method for manufacturing the same.
  • hyaluronic acid which is a constituent of various tissues in the human body, can help wound recovery, and thus, by introducing a crosslinking group, can help not only wound closure but also tissue regeneration.
  • the present inventors recognized that it is urgent to develop a sponge-type photo-crosslinked hyaluronic acid that does not cause discomfort such as stickiness and flow, and thus completed the present invention.
  • the object of the present invention is that it can be used on various parts of the body because it has no stickiness and dripping, and it has excellent water binding power to help tissue regeneration, and it has excellent biocompatibility so that it is absorbed into the skin when it is attached to the body for a long time. Therefore, it is to provide a photo-crosslinked hyaluronic acid sponge and a method of manufacturing the same that can reduce the troubles to be removed.
  • Another object of the present invention is to provide a photo-crosslinked hyaluronic acid sponge and a method of manufacturing the same that can be usefully used as a medical hemostatic agent, wound coating agent, and anti-adhesion agent in a porous form, including polymers of various lengths through a photo-crosslinking reaction.
  • the present invention provides a photo-crosslinked hyaluronic acid sponge, a method of manufacturing the same, and a use thereof.
  • the present invention provides a photo-crosslinked hyaluronic acid sponge containing a compound represented by the following [Chemical Formula I].
  • R 1 is a C0 to C7 alkyl group
  • R 2 is a C0 to C1 alkyl group
  • n is a positive integer from 1 to 10000.
  • the compound represented by [Chemical Formula I] is characterized in that it is a compound shown in the following [Table 1].
  • the present invention provides a method of manufacturing a photo-crosslinked hyaluronic acid sponge prepared by the following steps.
  • R 1 is a C0 to C7 alkyl group
  • R 2 is a C0 to C1 alkyl group
  • n is a positive integer from 1 to 10000.
  • the step (S1) is characterized by consisting of the following steps.
  • the compound having a photo-crosslinking functional group is methacrylic anhydride, acrylic anhydride, 3-butenoic anhydride, and 4-pentenoic anhydride. ), 5-hexenoic anhydride, 6-heptenoic anhydride, 7-octenoic anhydride, 8-nonenoic anhydride And 9-decenoic anhydride.
  • the step (S2) is characterized by consisting of the following steps.
  • the photoinitiator is 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]2-methyl-1-propanone (2-hydroxy-1-[4-(2-hydroxyethoxy) )phenyl] 2-methyl-1-propanone, 3-(4-benzoylphenoxy)-2-hydroxy-N, N, N-trimethyl-1-propanaminium-chloride (3-(4-benzoylphenoxy) -2-hydroxy-N,N,N-trimethyl-1-propanaminium-chloride), methyldiethanola mine, sodium phenyl-2,4,6-trimethylbenzoylphosphinate (sodium phenyl-2,4) ,6-tr imethylbenzoylphosphinate), lithium phenyl-2,4,6-trimethylbenzoylphosphinate (li thium phenyl-2,4,6-trimethylbenzoylphosphinate), benzyldimethyl ketal and 1-hydroxy-cycl
  • the photo-crosslinkable hyaluronic acid sponge and its manufacturing method of the present invention can be used on various parts of the body because there is no stickiness and dripping, and it can help tissue regeneration due to its excellent water binding ability, and has excellent biocompatibility. If it is attached to the skin for a long time, it is absorbed into the skin, reducing the trouble of removing it.
  • the photo-crosslinked hyaluronic acid sponge and its manufacturing method of the present invention can be usefully used as a medical hemostatic agent, wound coating agent, and anti-adhesion agent in a porous form, including polymers of various lengths through a photo-crosslinking reaction.
  • FIG. 1 is a block diagram schematically showing a method of manufacturing a light-crosslinked hyaluronic acid sponge of the present invention.
  • Figure 3 is a photograph confirming the water binding force confirmed in Experimental Example 1.
  • the numerical range includes the numerical values defined in the above range. All maximum numerical limits given throughout this specification include all lower numerical limits as if the lower numerical limits were expressly written. All minimum numerical limits given throughout this specification include all higher numerical limits as if the higher numerical limits were expressly written. All numerical limits given throughout this specification will include all better numerical ranges within the wider numerical range, as if the narrower numerical limits were expressly written.
  • the present invention relates to a photo-crosslinked hyaluronic acid sponge, and more specifically to a photocrosslinked hyaluronic acid sponge comprising a compound represented by the following [Chemical Formula I].
  • R 1 is a C0 to C7 alkyl group
  • R 2 is a C0 to C1 alkyl group
  • n is a positive integer from 1 to 10000.
  • the compound represented by [Chemical Formula I] may have a structure in which hyaluronic acid is a parent, and a functional group capable of photocrosslinking is added to the hyaluronic acid, and more specifically, the compound represented by [Chemical Formula I] is shown in the following [Table] It may be a compound described in 1].
  • the present invention provides a method for producing a photo-crosslinked hyaluronic acid sponge prepared by the following steps.
  • R 1 is a C0 to C7 alkyl group
  • R 2 is a C0 to C1 alkyl group
  • n is a positive integer from 1 to 10000.
  • step (S1) of preparing the compound represented by [Chemical Formula I] may consist of the following steps.
  • the compound represented by [Chemical Formula I] may be a compound shown in the following [Table 1].
  • the step (S1A) is a step of preparing a first solution by dissolving hyaluronic acid in water (H 2 O); as, cooling the first solution at 0 to 5° C. may be additionally included. have.
  • the first solution may contain the hyaluronic acid and water in a weight ratio of 1: 4 to 100 (hyaluronic acid: water), preferably hyaluronic acid and water 1: 4 to 20 (hyaluronic acid: water) It may be included in a weight ratio, and most preferably, it may be included in a weight ratio of 1: 8 to 12 (hyaluronic acid: water).
  • the step (S1B) may be a step of preparing a second solution by adding a compound and a base having a photocrosslinking functional group to the first solution prepared in step (S1A).
  • the compound having the photocrosslinking functional group is methacrylic anhydride, acrylic anhydride, 3-butenoic anhydride, 4-pentenoic anhydride, and 5-hexyl.
  • Senoic anhydride (5-hexenoic anhydride), 6-heptenoic anhydride (6-heptenoic anhydride), 7-octenoic anhydride (7-octenoic anhydride), 8-nonenoic anhydride (8-nonenoic anhydride) and 9-dekenoic acid It may be one or more selected from the group consisting of 9-decenoic anhydride.
  • the compound having a photo-crosslinking functional group is bonded to the compound represented by [Chemical Formula I] to form a polymer through a photo-crosslinking reaction to form a structure of a photo-crosslinked hyaluronic acid sponge.
  • the base is sodium hydroxide (NaOH), sodium carbonate (Na2CO3), sodium bicarbonate (NaHCO3), potassium hydroxide (KOH), sodium carbonate (K2CO3), and sodium bicarbonate.
  • bicarbonate, KHCO3) may be one or more selected from the group consisting of, preferably sodium hydroxide or potassium hydroxide having a concentration of 1 to 5M, most preferably sodium hydroxide or potassium hydroxide having a concentration of 1 to 3M Can be
  • step (S1B) weakens the anhydride bond of the compound having a photo-crosslinking functional group, thereby inducing a polymerization reaction between the hydroxy (-OH) bonded to hyaluronic acid and the compound having a photo-crosslinking functional group. Induce bonds to be created.
  • the pH may be maintained at 5 to 9, preferably, the pH may be maintained at 6 to 8.
  • the reaction can be effectively carried out in the formation of ester bonds of the compound represented by [Chemical Formula I].
  • the (S1C) step may be a step of preparing a compound represented by the [Formula I] by adding alcohol to the second solution prepared in the step (S1B) to generate a precipitate and drying it.
  • the alcohol may be a branched or straight C1 to C4 lower alcohol, preferably one or more selected from the group consisting of methanol, ethanol, isopropanol and 1,4-butanol, and most preferably ethanol and It may be one or more selected from the group consisting of isopropanol.
  • the drying may be vacuum drying, reduced pressure drying, boiling drying, hot air drying, spray drying or freeze drying, preferably vacuum drying or vacuum drying, and most preferably vacuum drying.
  • the step (S2) of preparing a photo-crosslinked hyaluronic acid sponge by adding a photoinitiator to the compound represented by [Chemical Formula I] may consist of the following steps.
  • the (S2A) step may be a step of preparing an aqueous solution by adding a photoinitiator and water (H 2 O) to the compound represented by the [Chemical Formula I] prepared in the (S1) step.
  • the photoinitiator is 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]2-methyl-1-propanone (2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl] 2-methyl-1-propanone, 3-(4-benzoylphenoxy)-2-hydroxy-N, N, N-trimethyl-1-propanaminium-chloride (3-(4-benzoylphenoxy)-2- hydroxy-N,N,N-trimethyl-1-propanaminium-chloride), methyldiethanola mine, sodium phenyl-2,4,6-trimethylbenzoylphosphinate (sodium phenyl-2,4,6- tr imethylbenzoylphosphinate), lithium phenyl-2,4,6-trimethylbenzoylphosphinate (li thium phenyl-2,4,6-trimethylbenzoylphosphinate), benzyldimethyl ketal and 1-hydroxy-cyclohexyl phen
  • the photoinitiator may react with a photocrosslinking functional group bonded to the compound represented by [Chemical Formula I] to initiate a polymerization reaction due to ultraviolet irradiation.
  • the compound represented by [Chemical Formula I]: the photoinitiator may be mixed in a weight ratio of 1 to 50: 1, and preferably the compound represented by the [Chemical Formula I]: the photoinitiator is 10 to 30: It can be mixed in a weight ratio of 1.
  • the step (S2B) may be a step of performing a photocrosslinking reaction by irradiating ultraviolet rays (Ultraviolet Ray, UV) to the aqueous solution prepared in step (S2A), and the ultraviolet rays may be 300 to 500 nm, Preferably it may be 350 to 450 nm.
  • ultraviolet rays Ultraviolet Ray, UV
  • the (S2C) step may be a step of preparing a photo-crosslinked hyaluronic acid sponge by freeze-drying at -40°C to 40°C after performing the (S2B) step.
  • the lyophilization may be performed for 12 to 48 hours, preferably for 18 to 36 hours.
  • the lyophilization may be performed at a pressure of 1 to 100 mTorr, and preferably may be performed at a pressure of 1 to 50 mTorr.
  • the present invention can be used for medical hemostatic agents, wound cloning agents or anti-adhesion agents including the photo-crosslinked hyaluronic acid sponge, and can be used as long as it can be used as a biodegradable medical material without limitation.
  • the photo-crosslinked hyaluronic acid sponge containing the compound represented by the above [Chemical Formula I] and a method for preparing the same are as defined above, and all the matters mentioned are applied equally unless contradictory to each other.
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and methacrylic anhydride and 3M NaOH were added to the first solution. Added to prepare a second solution. In addition, ethanol was added to the second solution to generate a precipitate, and the precipitate was purified and vacuum dried to prepare a compound represented by [Chemical Formula 1].
  • HA hyaluronic acid
  • 3M NaOH methacrylic anhydride and 3M NaOH
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and acrylic anhydride and 3M NaOH were added to the first solution.
  • HA hyaluronic acid
  • 3M NaOH acrylic anhydride
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and 3-butenoic anhydride to the first solution And 3M NaOH was added to prepare a second solution.
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and 4-pentenoic anhydride to the first solution And 3M NaOH was added to prepare a second solution. Then, ethanol was added to the second solution to generate a precipitate, and the precipitate was purified and vacuum dried to prepare a compound represented by [Chemical Formula 4].
  • HA hyaluronic acid
  • H 2 O water
  • 4M NaOH 3M NaOH
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and 5-hexenoic anhydride was added to the first solution. ) And 3M NaOH were added to prepare a second solution. Then, ethanol was added to the second solution to generate a precipitate, and the precipitate was purified and vacuum dried to prepare a compound represented by [Chemical Formula 5].
  • HA hyaluronic acid
  • H 2 O water
  • 3M NaOH were added to prepare a second solution.
  • ethanol was added to the second solution to generate a precipitate
  • the precipitate was purified and vacuum dried to prepare a compound represented by [Chemical Formula 5].
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and 6-heptenoic anhydride to the first solution And 3M NaOH was added to prepare a second solution. Then, ethanol was added to the second solution to generate a precipitate, and the precipitate was purified and vacuum dried to prepare a compound represented by [Chemical Formula 6].
  • HA hyaluronic acid
  • H 2 O water
  • 3M NaOH 3M NaOH
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and 7-octenoic anhydride to the first solution ) And 3M NaOH were added to prepare a second solution. Then, ethanol was added to the second solution to generate a precipitate, and the precipitate was purified and vacuum dried to prepare a compound represented by [Chemical Formula 7].
  • HA hyaluronic acid
  • H 2 O water
  • 3M NaOH 3M NaOH
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and 8-nonenoic anhydride to the first solution And 3M NaOH was added to prepare a second solution. Then, ethanol was added to the second solution to generate a precipitate, and the precipitate was purified and vacuum dried to prepare a compound represented by [Chemical Formula 8].
  • HA hyaluronic acid
  • H 2 O water
  • 8-nonenoic anhydride 3M NaOH
  • a first solution was prepared by adding 10 g of hyaluronic acid (HA) (26 mmol) to 100 ml of water (H 2 O), and 9-decenoic anhydride to the first solution And 3M NaOH was added to prepare a second solution.
  • ethanol was added to the second solution to generate a precipitate, and the precipitate was purified and vacuum dried to prepare a compound represented by [Chemical Formula 9].
  • Comparative Example 1 Comparative photo-crosslinked hyaluronic acid sponge containing a compound represented by [Chemical Formula 4]
  • Example 1 is advantageous in providing a moist environment by absorbing blood or exudate and maintaining its shape after surgery or when adhering to wound skin, so that it can help organ or skin regeneration.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Materials For Medical Uses (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

La présente invention concerne une éponge d'acide hyaluronique photo-réticulé et son procédé de fabrication et, plus particulièrement, une éponge d'acide hyaluronique photo-réticulé et son procédé de fabrication, l'éponge pouvant : être utilisée sur diverses parties du corps du fait qu'elle n'a pas d'adhésivité et ne dégoutte pas ; aider à la régénération tissulaire grâce à une excellente capacité de liaison à l'humidité ; être absorbée dans la peau du fait qu'elle a une excellente biocompatibilité lorsqu'elle est fixée au corps pendant longtemps, ce qui permet de réduire l'effort nécessaire pour retirer l'éponge ; et être utilisée efficacement en tant qu'agent hémostatique médical, agent de recouvrement de plaie et agent antiadhésif sous une forme poreuse du fait qu'elle comprend des polymères de différentes longueurs obtenus grâce à une réaction de photo-réticulation.
PCT/KR2019/015909 2019-11-07 2019-11-20 Éponge d'acide hyaluronique photo-réticulé et son procédé de fabrication WO2021090997A1 (fr)

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CN113754919A (zh) * 2021-09-27 2021-12-07 江南大学 一种快速吸血、孔道有序的止血海绵的制备及应用
CN113817214A (zh) * 2021-08-06 2021-12-21 广东省科学院健康医学研究所 一种多孔水凝胶海绵及其制备方法和应用

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KR102577913B1 (ko) * 2020-11-20 2023-09-14 주식회사 에스엔비아 광가교형 공중합 히알루론산 스펀지 및 이의 제조방법

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CN113754919B (zh) * 2021-09-27 2022-04-29 江南大学 一种快速吸血、孔道有序的止血海绵的制备及应用

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