WO2023199855A1 - 共重合体、医療用組成物及び被覆医療デバイス並びにそれらの製造方法 - Google Patents

共重合体、医療用組成物及び被覆医療デバイス並びにそれらの製造方法 Download PDF

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WO2023199855A1
WO2023199855A1 PCT/JP2023/014354 JP2023014354W WO2023199855A1 WO 2023199855 A1 WO2023199855 A1 WO 2023199855A1 JP 2023014354 W JP2023014354 W JP 2023014354W WO 2023199855 A1 WO2023199855 A1 WO 2023199855A1
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Prior art keywords
copolymer
medical device
coated
coated medical
acid
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English (en)
French (fr)
Japanese (ja)
Inventor
早央莉 田原
瑠美子 北川
正孝 中村
功治 門脇
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Toray Industries Inc
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Toray Industries Inc
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Priority to US18/849,836 priority Critical patent/US20250205397A1/en
Priority to JP2023534125A priority patent/JPWO2023199855A1/ja
Priority to KR1020247025597A priority patent/KR20250003474A/ko
Priority to CN202380029363.5A priority patent/CN118922459A/zh
Priority to CA3245709A priority patent/CA3245709A1/en
Priority to EP23788274.1A priority patent/EP4501993A4/en
Publication of WO2023199855A1 publication Critical patent/WO2023199855A1/ja
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    • G—PHYSICS
    • G02—OPTICS
    • G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
    • G02C7/00—Optical parts
    • G02C7/02—Lenses; Lens systems ; Methods of designing lenses
    • G02C7/04—Contact lenses for the eyes
    • 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
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular 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
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/24—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0014—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular 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
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
    • C08F220/365—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate containing further carboxylic moieties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/24—Homopolymers or copolymers of amides or imides
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses
    • 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
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/10—Materials for lubricating medical devices
    • 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
    • A61L2420/00—Materials or methods for coatings medical devices
    • A61L2420/02—Methods for coating medical devices

Definitions

  • the present invention relates to copolymers, medical compositions, coated medical devices, and methods of manufacturing them.
  • Patent Document 1 a method of layering and coating polymers with different properties
  • Patent Document 2 a method of coating with a polymer containing an ampholyte compound
  • Patent Document 2 a method of coating with a polymer containing an ampholyte compound
  • Patent Document 2 a method of coating with a polymer containing an ampholyte compound
  • Patent Document 2 A method of coating a random copolymer of acryloyloxyethyl-N,N-dimethylammonium- ⁇ -N-methylcarboxybetaine and butyl methacrylate (Patent Document 3) is known.
  • the present invention provides a copolymer and a method for producing the same that can impart excellent biocompatibility to the surface of a medical device through a simple process and maintain that biocompatibility even when exposed to frictional stimulation.
  • the purpose is to provide the following.
  • the present invention provides a copolymer containing the following (A), (B) and (C) as monomer components: (A) a compound having a carboxybetaine group and/or a sulfobetaine group; (B) (meth)acrylic acid; (C) Acrylamide derivative.
  • a copolymer can be provided.
  • the copolymer of the present invention is a multicomponent copolymer containing (A) a compound having a carboxybetaine group and/or a sulfobetaine group, (B) (meth)acrylic acid, and (C) an acrylamide derivative as monomer components ( Hereinafter, it is "copolymer T").
  • the copolymer of the present invention is non-crosslinked and may be linear or branched, but from the viewpoint of ease of production, linear is preferable.
  • the copolymer of the present invention may be a random copolymer, an alternating copolymer, a block copolymer, or a graft copolymer. From the viewpoint of ease of production, random copolymers are preferred.
  • the "monomer component" that is a raw material for the copolymer of the present invention refers to a low molecular weight compound that can be polymerized and/or crosslinked using a photopolymerization initiator and/or a thermal polymerization initiator.
  • the copolymer containing the above-mentioned (A), (B) and (C) as monomer components means that the copolymer has a structure derived from the above-mentioned monomer components (A), (B) and (C). to include.
  • monomer component (A) a compound having a carboxybetaine group and/or a sulfobetaine group
  • monomer component (A) 2-[[2-(methacryloyloxy) ethyl]dimethylammonio]acetic acid, 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propanoic acid (hereinafter referred to as "CBMA”), 3-[(3-acrylamidopropyl)dimethylammonio]propanoic acid ( 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propane-1-sulfonic acid (hereinafter referred to as "SBMA”), 4-[[2-(methacryloyloxy)ethyl]dimethyl ammonio]butane-1-sulfonic acid, 3-[[2-(acryloyloxy)ethy
  • (B) (meth)acrylic acid (hereinafter referred to as “monomer component (B)”), which is one of the monomer components, refers to methacrylic acid and/or acrylic acid (hereinafter referred to as "AA"). From the viewpoint of polymerization stability, acrylic acid is preferred.
  • acrylamide derivative (hereinafter referred to as “monomer component (C)"
  • monomer component (C) which is one of the monomer components, includes, for example, acrylamide, N-isopropylacrylamide, N,N-dimethylacrylamide (hereinafter referred to as "DMAA”).
  • DMAA N,N-diethylacrylamide, N-methyl-N-ethylacrylamide or N,N-di(hydroxyethyl)acrylamide. From the viewpoint of polymerization stability, DMAA is preferred.
  • the proportion of monomer component (A), monomer component (B), and monomer component (C) in the copolymer of the present invention is preferably 1 to 40 mol% of monomer component (A); (B) is preferably 1 to 35 mol%, and monomer component (C) is preferably 25 to 98 mol%.
  • the proportion of the monomer component (A) in the copolymer of the present invention is more preferably 1 to 30 mol%, and even more preferably 5 to 25 mol%.
  • the proportion of the monomer component (B) in the copolymer of the present invention is more preferably 1 to 25 mol%, and even more preferably 5 to 15 mol%.
  • the proportion of the monomer component (C) in the copolymer of the present invention is more preferably 45 to 98 mol%, and even more preferably 60 to 90 mol%.
  • the method for producing a copolymer of the present invention involves polymerizing monomers containing (A) a compound having a carboxybetaine group and/or a sulfobetaine group, (B) (meth)acrylic acid, and (C) an acrylamide derivative. and a polymerization step to obtain a copolymer.
  • a polymerization initiator such as a thermal polymerization initiator or a photopolymerization initiator can be used.
  • thermal polymerization initiator examples include peroxides and azo compounds.
  • Thermal polymerization initiators may be selected from those with optimal decomposition characteristics for the desired reaction temperature, but in general, azo compounds or peroxides with a 10-hour half-life temperature of 40 to 120°C are preferred. .
  • V-50 2,2'-azobis(isobutyronitrile) (AIBN), 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(2,4- dimethylvaleronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 2,2'-azobis[2-(2-imidazolin-2-yl)propane], 2,2'-azobis(2- methylpropionamidine) dihydrochloride (hereinafter referred to as "V-50”), 2,2'-azobis[N-(2-carboxyethyl)-2-methylpropionamidine], 2,2'-azobis[2-methyl -N-(2-hydroxyethyl)propionamide], 2,2'-azobis(N-butyl-2-methylpropionamide), 2,2'-azobis(2-methylpropionate) dimethyl, 4,4' -azobis(4-cyanovaleric acid), tert-butyl hydroperoxide, cumene hydroperoxide,
  • photopolymerization initiators include carbonyl compounds such as aromatic ⁇ -hydroxyketone, alkoxyoxybenzoin, acetophenone, acylphosphine oxide or bisacylphosphine oxide, tertiary amine + diketone, peroxide, azo compound, sulfur. Compounds, halogen compounds or metal salts may be mentioned.
  • 1-hydroxycyclohexylphenylketone 2-hydroxy-2-methyl-1-phenyl-propan-1-one, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl Pentylphosphine oxide (DMBAPO), bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (“Irgacure”® 819), 2,4,6-trimethylbenzyldiphenylphosphine oxide and 2,4,6- Mention may be made of trimethylbenzoyldiphenylphosphine oxide, benzoin methyl ether or a combination of camphorquinone and ethyl 4-(N,N-dimethylamino)benzoate.
  • DMBAPO bis(2,6,-dimethoxybenzoyl)-2,4,4-trimethyl Pentylphosphine oxide
  • Irgacure bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide
  • polymerization initiators may be used alone or in combination, but in order to moderately promote polymerization and crosslinking of monomer components and obtain a copolymer with a desired molecular weight, the proportion of polymerization initiators in the polymerization mixture must be The proportion of the initiator is preferably 5% by mass or less.
  • the "polymerization mixture” refers to a mixture in which each monomer component for obtaining a copolymer, a polymerization initiator, and a chain transfer agent that may be added as necessary are dissolved in a solvent.
  • Examples of the solvent for obtaining the polymerization mixture include water, methanol, ethanol, propanol, 2-propanol, butanol, 2-butanol, tert-butanol, tert-amyl alcohol, 3,7-dimethyl-3-octanol, and ethylene.
  • Alcohol solvents such as glycol, diethylene glycol, triethylene glycol, tetraethylene glycol or polyethylene glycol; aromatic hydrocarbon solvents such as benzene, toluene or xylene; hexane, heptane, octane, decane, petroleum ether, kerosene, ligroin or paraffin Aliphatic hydrocarbon solvents such as cyclopentane, cyclohexane or ethylcyclohexane; Ketone solvents such as acetone, methyl ethyl ketone or methyl isobutyl ketone; ethyl acetate, butyl acetate, amyl acetate, ethyl lactate , ester solvents such as methyl benzoate or ethylene glycol diacetate; or diethyl ether, tert-butyl methyl ether, tetrahydrofuran, dioxane, ethylene glycol
  • the solvent is preferably water, methanol, tert-butanol, tert-amyl alcohol, 3,7-dimethyl-3-octanol, or tetrahydrofuran, or a mixed solvent thereof, and water is more preferred.
  • the total proportion of monomer components in the polymerization mixture is preferably 10 to 80% by mass, more preferably 15 to 65% by mass, in order to obtain a copolymer with a desired molecular weight while appropriately suppressing runaway due to polymerization heat.
  • the polymerization mixture is heated to advance the polymerization reaction and obtain the desired copolymer.
  • the reaction temperature in the polymerization step may be selected depending on the decomposition temperature of the polymerization initiator, the boiling points of the solvent and monomer, the reaction time, etc., but in order to obtain the desired copolymer in a good yield, a temperature of 20°C to 180°C is recommended.
  • the temperature is preferably 50°C to 150°C, more preferably 60°C to 120°C.
  • the reaction time in the polymerization step may be selected depending on the type and concentration of the polymerization initiator and monomer used, the reaction temperature, etc., but in order to obtain the desired copolymer in a good yield, it is preferably 1 to 48 hours. More preferably 2 to 24 hours, and even more preferably 3 to 12 hours.
  • the weight average molecular weight (hereinafter referred to as "Mw") of the copolymer of the present invention is set at 1,000 to 5,000,000 in order to obtain suitable slipperiness while keeping the viscosity (operability) of the solution appropriate. is preferable, 5,000 to 3,000,000 is more preferable, and even more preferably 10,000 to 1,000,000.
  • the coated medical device of the present invention is one in which at least a portion of the surface of the medical device is coated with the copolymer of the present invention.
  • Materials for medical devices include water-containing base materials such as hydrogels (including silicone hydrogels), acrylic resins such as polymethyl methacrylate, silicone base materials with siloxane bonds, metals such as aluminum, or glass. Any non-water-containing base material may be used.
  • water-containing base materials such as hydrogels (including silicone hydrogels), acrylic resins such as polymethyl methacrylate, silicone base materials with siloxane bonds, metals such as aluminum, or glass. Any non-water-containing base material may be used.
  • Examples of medical devices include ophthalmic lenses, skin dressings, wound dressings, skin protection materials, skin drug carriers, infusion tubes, gas transport tubes, drainage tubes, blood circuits, and coating tubes. , a catheter, a stent, a sheath biosensor chip, a heart-lung machine, or a dressing for an endoscope.
  • medical devices selected from ophthalmic lenses and stents are preferred because of the high demand for the effects of the present invention.
  • Ophthalmic lenses include contact lenses such as soft contact lenses, hard contact lenses, and hybrid contact lenses, scleral lenses, intraocular lenses, artificial corneas, corneal inlays, corneal onlays, and spectacle lenses. Among these, contact lenses are preferred.
  • a stent for respiratory organs is preferred.
  • the respiratory organ in the present invention is a general term for organs related to breathing, and includes, for example, airways, oral cavity, nasal cavity, larynx, trachea, bronchi, bronchioles, lungs, and the like.
  • the stent according to an embodiment of the present invention is a stent for the respiratory tract, preferably a stent for the airways, trachea, bronchus, or lungs.
  • the medical composition of the present invention contains the copolymer of the present invention and a solvent.
  • the medical composition of the present invention is used to coat at least a portion of the surface of the medical device with the copolymer of the present invention to obtain a coated medical device of the present invention.
  • the method for producing a medical composition of the present invention includes a blending step of mixing the copolymer of the present invention and a solvent to obtain a medical composition.
  • Examples of the solvent used in the above-mentioned preparation step include the same solvents as those used to obtain the above-mentioned "polymerization mixture”.
  • the proportion of the copolymer of the present invention in the medical composition of the present invention is 0.0001 to 30.0000 mass in order to increase the viscosity (operability) of the solution while making the thickness of the coating layer appropriate. %, more preferably 0.0010 to 20.0000% by mass, even more preferably 0.0050 to 15.0000% by mass.
  • the surface of the medical device can be coated with the copolymer of the present invention. That is, the method for producing a coated medical device includes a coating step of bringing the medical composition of the present invention into contact with the surface of the medical device to obtain a coated medical device.
  • the medical device is an ophthalmic lens
  • the medical composition of the present invention and the ophthalmic lens are sealed in a container, brought into contact, and heat-treated (coating step).
  • the surface of an ophthalmic lens can be coated with the copolymer of the invention.
  • heating operation methods include high-pressure steam method, visible light, electromagnetic wave irradiation such as infrared rays or microwaves, electric heating method, electromagnetic induction heating method, dry heat method, and flame method. From the viewpoint of improving lubricity and shortening the manufacturing process, a high-pressure steam method using an autoclave is preferred.
  • the heating temperature in the above heating operation is preferably 60 to 200°C, more preferably 80 to 180°C, in order to obtain a coated medical device surface that exhibits good water wettability and slipperiness while maintaining the strength of the medical device itself.
  • the temperature is preferably 100 to 170°C, more preferably 110 to 150°C.
  • the heating time in the above heating operation is preferably 5 to 600 minutes, more preferably 10 to 400 minutes, in order to obtain a coated medical device surface that exhibits good water wettability and slipperiness while maintaining the strength of the medical device itself.
  • 15 to 300 minutes is more preferable.
  • the initial pH of the medical composition of the present invention is 2.0 to 6.0, since the composition does not become cloudy and a medical device with good transparency, surface wettability, and slipperiness is obtained. 0 is preferred.
  • the initial pH is more preferably 2.2 to 5.0, even more preferably 2.4 to 4.5, particularly preferably 2.5 to 4.0.
  • the pH of the medical composition of the present invention can be adjusted, for example, by adding an acidic substance.
  • acidic substances include acetic acid, citric acid, formic acid, ascorbic acid, trifluoromethanesulfonic acid, methanesulfonic acid, nitric acid, sulfuric acid, phosphoric acid, or hydrochloric acid.
  • Citric acid, ascorbic acid or sulfuric acid which have low volatility and high safety for living organisms, are preferred.
  • a buffer may be added to the medical composition of the present invention.
  • buffering agents include borates such as boric acid and sodium borate; citrates such as citric acid and potassium citrate; bicarbonates such as sodium bicarbonate; Na 2 HPO 4 , NaH 2 PO 4 , or phosphates such as KH 2 PO 4 ; TRIS (tris(hydroxymethyl)aminomethane), 2-bis(2-hydroxyethyl)amino-2-(hydroxymethyl)-1,3-propanediol, bis-amino Polyol, triethanolamine, ACES (N-(2-acetamido)-2-aminoethanesulfonic acid), BES (N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid), HEPES (4- (2-hydroxyethyl)-1-piperazineethanesulfonic acid), MES (2-(N-morpholino)ethanesulfonic acid), MOPS (3-[N-morpholino]-propanesulfonic acid), PIP
  • the pH of the medical composition of the present invention may change during a coating process such as a heating operation.
  • the pH of the medical composition immediately after the heating operation is preferably 2.0 to 6.5, preferably 2.2 to 5.0, in order to optimize the physical properties of the resulting coated medical device. 9 is more preferred, 2.3 to 5.5 is even more preferred, and 2.4 to 5.0 is particularly preferred.
  • the coated medical device obtained by the above coating step may be further subjected to other treatments.
  • other treatments include repeating the same coating step as described above, or contacting the surface of the coated medical device with a solvent or buffer solution that does not contain the copolymer of the present invention, and then performing the same heating operation. treatment, radiation irradiation, layer-by-layer treatment (LbL treatment) in which polymer materials with opposite charges are coated alternately one layer at a time, crosslinking treatment with metal ions, or chemical crosslinking treatment.
  • the pH of the buffer solution used in the heat treatment is preferably 6.3 to 7.8, which is physiologically acceptable, more preferably 6.5 to 7.6 or higher, and 6.8 to 7.4. is even more preferable.
  • composition of the phosphate buffer used was as follows. KCl: 0.2 g/L, KH 2 PO 4 : 0.2 g/L, NaCl: 8.0 g/L, Na 2 HPO 4 : 1.2 g/L, EDTA: 0.5 g/L.
  • test sample The coated medical device or medical device (hereinafter referred to as “test sample”) was washed with a phosphate buffer at room temperature, and then immersed in the phosphate buffer at room temperature for 24 hours or more and allowed to stand.
  • This test sample (hereinafter referred to as “test sample S”) was lifted from the phosphate buffer and held in air so that its longitudinal direction was in the direction of gravity.
  • test sample was in the shape of a lens, it was held in the air so that the diameter direction of the circle formed by the edge of the lens was in the direction of gravity.
  • a part of the liquid film is cut refers to a state in which the liquid film on the surface of the test sample S is no longer able to maintain its shape, and a part of the surface of the test sample S is no longer covered by the liquid film.
  • A A liquid film on the surface is maintained for 20 seconds or more.
  • B The liquid film on the surface breaks in 15 seconds or more and less than 20 seconds.
  • C The liquid film on the surface breaks in 5 seconds or more and less than 15 seconds.
  • D The liquid film on the surface breaks in 1 second or more and less than 5 seconds.
  • E The liquid film on the surface breaks instantly (less than 1 second).
  • sample P a test piece with a width (minimum part) of 5 mm and a length of 14 mm was cut out using a punching die
  • sample K a test piece with a diameter of 4 mm was cut out using a punching die
  • BCA bisinchoninic acid
  • Example 1 In a 500 mL four-necked flask, add 2.29 g (10 mmol) of CBMA (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.72 g (10 mmol) of AA (manufactured by Fuji Film Wako Pure Chemical Industries), and 7.93 g (80 mmol) of DMAA (manufactured by Fuji Film Wako Pure Chemical Industries).
  • CBMA manufactured by Tokyo Chemical Industry Co., Ltd.
  • AA manufactured by Fuji Film Wako Pure Chemical Industries
  • DMAA manufactured by Fuji Film Wako Pure Chemical Industries
  • Example 2 The same operation as in Example 1 was performed, except that 2.79 g (10 mmol) of SBMA (manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of CBMA, to obtain 114.45 g of copolymer T2 .
  • the properties of the obtained copolymer T2 were as shown in Table 1.
  • Copolymer T C2 was prepared in the same manner as in Example 1 except that N-vinylpyrrolidone (hereinafter referred to as "NVP"; manufactured by Tokyo Kasei Kogyo, 1.11 g, 10 mmol) was used in place of CBMA. .63g was obtained.
  • NDP N-vinylpyrrolidone
  • the properties of the obtained copolymer T C2 were as shown in Table 1.
  • Example 3 As medical device A, a commercially available silicone hydrogel lens "Acuvue Oasys" (registered trademark; manufactured by Johnson & Johnson) containing polyvinylpyrrolidone and silicone as main components was used. Copolymer T1 was added to a phosphate buffer solution at a concentration of 0.3% by mass, and the pH was adjusted to 3.0 using citric acid. 3 mL of the prepared solution was transferred to a glass vial, medical device A was immersed therein, and heated at 121° C. for 30 minutes in an autoclave. The heated medical device was washed with a phosphate buffer solution for 30 seconds, then placed in a new phosphate buffer solution, and further heated in an autoclave at 121° C. for 30 minutes to obtain a coated medical device.
  • a commercially available silicone hydrogel lens "Acuvue Oasys" registered trademark; manufactured by Johnson & Johnson
  • Copolymer T1 was added to a phosphate buffer solution at a concentration of
  • Example 4 A coated medical device was obtained in the same manner as in Example 3, except that copolymer T 2 was used in place of copolymer T 1 .
  • Example 5 As the medical device M, a commercially available hydrogel lens "Medalist” (registered trademark; manufactured by Baush & Lomb) containing N-vinylpyrrolidone and 2-hydroxyethyl methacrylate (2-HEMA) as the main components was used. A coated medical device was obtained by performing the same operation as in Example 3, except that medical device M was used instead of medical device A.
  • Medalist registered trademark; manufactured by Baush & Lomb
  • 2-HEMA 2-hydroxyethyl methacrylate
  • Example 6 A coated medical device was obtained in the same manner as in Example 5, except that copolymer T 2 was used in place of copolymer T 1 .
  • Example 3 A coated medical device was obtained in the same manner as in Example 3, except that copolymer T C1 was used instead of copolymer T1 .
  • Example 4 A coated medical device was obtained in the same manner as in Example 3, except that copolymer T C2 was used in place of copolymer T1 .
  • Example 5 A coated medical device was obtained in the same manner as in Example 5, except that copolymer T C1 was used instead of copolymer T1 .
  • Example 6 A coated medical device was obtained in the same manner as in Example 5, except that copolymer T C2 was used in place of copolymer T 1 .
  • Copolymer T 3 was prepared in the same manner as in Example 1, except that 4.59 g (20 mmol) of CBMA, 0.72 g (10 mmol) of AA, 6.94 g (70 mmol) of DMAA, and purified water (90.21 g) were used. 122.46g of was obtained. The properties of the obtained copolymer T3 were as shown in Table 4.
  • Copolymer T 4 was prepared in the same manner as in Example 1, except that 6.88 g (30 mmol) of CBMA, 0.72 g (10 mmol) of AA, 5.95 g (60 mmol) of DMAA, and purified water (98.49 g) were used. 135.47g of was obtained. The properties of the obtained copolymer T4 were as shown in Table 4.
  • Example 9 The same procedure as in Example 1 was carried out, except that 5.59 g (20 mmol) of SBMA, 0.72 g (10 mmol) of AA, 6.94 g (70 mmol) of DMAA, and purified water (99.22 g) were used in place of CBMA. 132.47g of Polymer T5 was obtained. The properties of the obtained copolymer T5 were as shown in Table 4.
  • Example 10 The same procedure as in Example 1 was carried out, except that 8.38 g (30 mmol) of SBMA, 0.72 g (10 mmol) of AA, 5.95 g (60 mmol) of DMAA, and purified water (115.44 g) were used in place of CBMA. 150.50 g of Polymer T 6 was obtained. The properties of the obtained copolymer T6 were as shown in Table 4.
  • Example 11 The same procedure as in Example 1 was carried out, except that 5.59 g (20 mmol) of SBMA, 1.44 g (20 mmol) of AA, 5.95 g (60 mmol) of DMAA, and purified water (96.78 g) were used in place of CBMA. 129.77 g of Polymer T7 was obtained. The properties of the obtained copolymer T7 were as shown in Table 4.
  • Example 9 The same procedure as in Example 1 was carried out except that 5.59 g (20 mmol) of SBMA, 2.88 g (40 mmol) of AA, 3.97 g (40 mmol) of DMAA, and purified water (91.91 g) were used in place of CBMA. 124.35g of polymer T C3 was obtained. The properties of the obtained copolymer T C3 were as shown in Table 4.
  • Example 10 The same operation as in Example 1 was performed except that 2.16 g (30 mmol) of AA, 6.94 g (70 mmol) of DMAA, and purified water (61.91 g) were used to obtain 91.02 g of copolymer T C4 .
  • the properties of the obtained copolymer T C4 were as shown in Table 4.
  • Example 12 to 16 A coated medical device was obtained in the same manner as in Example 3 , except that Copolymer T shown in Table 5 was used in place of Copolymer T1.
  • Example 17 to 21 A coated medical device was obtained in the same manner as in Example 5 , except that Copolymer T shown in Table 5 was used in place of Copolymer T1.
  • Example 22 As medical device D, a silicone stent (Dumon stent) was used. A coated medical device was obtained in the same manner as in Example 12 except that medical device D was used instead of medical device A.
  • Example 23 A coated medical device was obtained in the same manner as in Example 14, except that medical device D was used instead of medical device A.

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PCT/JP2023/014354 2022-04-13 2023-04-07 共重合体、医療用組成物及び被覆医療デバイス並びにそれらの製造方法 Ceased WO2023199855A1 (ja)

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JP2023534125A JPWO2023199855A1 (https=) 2022-04-13 2023-04-07
KR1020247025597A KR20250003474A (ko) 2022-04-13 2023-04-07 공중합체, 의료용 조성물 및 피복 의료 디바이스, 및 이들의 제조 방법
CN202380029363.5A CN118922459A (zh) 2022-04-13 2023-04-07 共聚物、医疗用组合物和覆盖医疗设备以及它们的制造方法
CA3245709A CA3245709A1 (en) 2022-04-13 2023-04-07 COPOLYMER, MEDICAL COMPOSITION AND COATED MEDICAL DEVICE, AND THEIR RESPECTIVE PRODUCTION PROCESSES
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WO2025121072A1 (ja) * 2023-12-05 2025-06-12 東洋紡株式会社 抗血栓性材料の製造方法
JP2025090323A (ja) * 2023-12-05 2025-06-17 東洋紡株式会社 抗血栓性材料の製造方法

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