US20190216985A1 - Method for sterilizing a medical device - Google Patents

Method for sterilizing a medical device Download PDF

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Publication number
US20190216985A1
US20190216985A1 US16/324,460 US201716324460A US2019216985A1 US 20190216985 A1 US20190216985 A1 US 20190216985A1 US 201716324460 A US201716324460 A US 201716324460A US 2019216985 A1 US2019216985 A1 US 2019216985A1
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composition
medical device
derivative
coating
solution
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Denzell McBURNEY
Ronald John KELLY
Morgan Tierney
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Teleflex Life Sciences LLC
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Teleflex Life Sciences ULC
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Publication of US20190216985A1 publication Critical patent/US20190216985A1/en
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Assigned to Teleflex Life Sciences Llc reassignment Teleflex Life Sciences Llc ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: TELEFLEX LIFE SCIENCES PTE. LTD.
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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K39/0002—Fungal antigens, e.g. Trichophyton, Aspergillus, Candida
    • 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
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
    • A61L2/08—Radiation
    • A61L2/081—Gamma radiation
    • 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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—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
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/505—Stabilizers
    • 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
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/52—Hydrogels or hydrocolloids
    • 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
    • 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
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • 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
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A61L29/143—Stabilizers
    • 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
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • A61L29/145—Hydrogels or hydrocolloids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M25/00—Catheters; Hollow probes
    • A61M25/002—Packages specially adapted therefor ; catheter kit packages
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65B—MACHINES, APPARATUS OR DEVICES FOR, OR METHODS OF, PACKAGING ARTICLES OR MATERIALS; UNPACKING
    • B65B55/00—Preserving, protecting or purifying packages or package contents in association with packaging
    • B65B55/02—Sterilising, e.g. of complete packages
    • B65B55/12—Sterilising contents prior to, or during, packaging
    • B65B55/16—Sterilising contents prior to, or during, packaging by irradiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/26—Cellulose ethers
    • C08L1/28—Alkyl ethers
    • C08L1/286—Alkyl ethers substituted with acid radicals, e.g. carboxymethyl cellulose [CMC]
    • 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
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
    • A61L2/08—Radiation
    • A61L2/10—Ultraviolet radiation
    • 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
    • A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
    • A61L2202/10—Apparatus features
    • A61L2202/18—Aseptic storing means
    • 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
    • A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
    • A61L2202/20—Targets to be treated
    • A61L2202/24—Medical instruments, e.g. endoscopes, catheters, sharps
    • 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
    • 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
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • 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
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
    • 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
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids

Definitions

  • the present invention relates to a method of producing a ready-to-use medical device with a functional coating comprising the steps of bringing the medical device, at least with its functional coating, in contact with a composition which prevents or retards degradation of the functional coating, and sterilizing the medical device and the composition via radiation.
  • medical devices may be provided with a hydrophilic coating on which a wetting fluid is applied so that the hydrophilic coating is activated and obtains its highly lubricious properties.
  • the wetting fluid protects the coating from drying out and thereby maintains the lubricious properties of the coating.
  • wetting fluids are water, mixtures of water and organic solvents, a body fluid, and aqueous solutions of salts, e.g. a saline solution having physiological osmolarity.
  • Medical devices can be wetted immediately prior to use or can be stored in the wetting liquid.
  • it is desirable to provide a ready-to-use medical device wherein the medical device with a hydrophilic coating is in a sterile package that contains enough wetting liquid to keep the coating wetted and thereby lubricious.
  • Such ready-to-use medical devices offer high convenience for the user because they do not require any preparation steps prior to use.
  • WO-A-2007/137669 discloses the use of a compound selected from aliphatic compounds, alicyclic compounds and antioxidants for protecting a hydrophilic coating which is sterilized by irradiation, in particular ⁇ -radiation or Electron-beam (E-beam) radiation.
  • a compound selected from aliphatic compounds, alicyclic compounds and antioxidants for protecting a hydrophilic coating which is sterilized by irradiation, in particular ⁇ -radiation or Electron-beam (E-beam) radiation.
  • WO-A-2013/017547 is directed to the use of a wetting liquid which may comprise water in an amount of 0 to 4.9 wt % and has a boiling point higher than 100° C. and a viscosity lower than 500 mPa ⁇ s.
  • WO-A-2006/037321 is directed to a medical device having a wetted hydrophilic coating and which is in a ready-to-use form.
  • the wetted hydrophilic coating comprises a coating composition comprising a hydrophilic polymer and a wetting agent comprising water and one or more lubricants.
  • WO-A-2006/117372 describes sterilization of medical devices having a wetted hydrophilic coating using radiation. It was found that when adding hydrophilic polymers to the storage medium prior to sterilization a high water retention and low friction is maintained when the medical device is stored in water.
  • WO-A-2011/076217 discloses a medical device having a hydrophilic coating and having been sterilized while in contact with a swelling medium comprising a low molecular polyol and a separate buffer and a method for sterilizing the set.
  • the pH is in the range of from 4 to 7.4.
  • ascorbic acid may be added as a stabilizing agent but that depends on the substrate, type of hydrophilic coating and gamma irradiation dosage.
  • WO-A-2012/085107 is directed to a hydrophilic catheter assembly including a wetting fluid.
  • the wetting fluid is preferably an aqueous liquid such as sterile water or saline.
  • WO-A-2008/151074 discloses a lubricant for medical devices which is suitable for radiation sterilization.
  • WO-A-00/47494 relates to a storage package which contains a medical device having a coated surface which exhibits a reduced friction when wetted.
  • WO-A-2007/065721 and WO-A-2007/065722 describe a hydrophilic coating composition which when cured results in a hydrophilic coating. It was found that a lubricious coating with a prolonged and improved dry-out time may be obtained when a polyelectrolyte is included in the hydrophilic coating composition from which said lubricious coating is formed.
  • compositions of the above-cited prior art are highly specific and can only be used for a limited group of hydrophilic coatings.
  • the particular components present in the composition have to be selected depending on the hydrophilic coating or the base solution.
  • the object of the present invention is to provide a method of producing a ready-to-use medical device with a functional coating which overcomes the disadvantages of the prior art and which results in a medical device with a functional coating that does not degrade during sterilization and has a hydrolytic stability so that a high quality is ensured during the intended shelf-life of the wetted medical device. Furthermore the method and the components used in the method should be non-toxic, easy to prepare, radiation sterilizable, inexpensive and cost effective, and usable for a large variety of functional coatings.
  • composition which comprises carboxymethyl cellulose (CMC) or a derivative or salt thereof and/or an antioxidant selected from gallic acid or a derivative thereof.
  • CMC carboxymethyl cellulose
  • a wetting agent comprising the composition comprising carboxymethyl cellulose or a derivative or salt thereof and/or an antioxidant selected from gallic acid or a derivative thereof.
  • composition is used as wetting agent that activates the functional coating of the medical device so that the desired low friction properties of the functional coating are achieved.
  • Bringing the medical device in contact with the composition which prevents or retards degradation of the functional coating may be achieved by dipping, or by spraying, or vaporizing the composition and contacting the medical device with the vaporized composition.
  • the composition used in the method according to the present invention is non-toxic, can be easily prepared and can be sterilized via radiation.
  • the composition can be used in a variety of different wetting agents irrespective of the base solutions.
  • the wetting agents the comprise a base solution, the composition and may comprise further components.
  • the composition according to the present invention prevents or retards the degradation of a functional coating on a medical device due to reactive species formed during exposure to radiation even at high irradiation energy levels.
  • composition used in the method of the present invention is more reactive to a reactive moiety formed from water due to the irradiation than the coating.
  • the composition used in the method of the present invention may be able to inactivate a radical which may be formed in a polymer in the coating thereby preventing uncontrolled and/or excessive crosslinking of the coating, and/or chain scission of the coating polymer, and/or delamination from the substrate.
  • composition used in the method of the present invention is formulated to act as a highly protective agent for all types of functional coating systems subjected to high radiation levels when the coated substrate, i.e. the medical device, is subjected to or exposed in a wetted environment comprising the composition. Furthermore, because the composition according to the present invention acts as protective agent, the functional coating of the medical device can be formed by crosslinking via an UV initiator, heat, ⁇ -ray, X-ray or E-beam.
  • the composition of the present invention is not limited to a particular coating material type or curing system, but it can be used for any functional coating.
  • composition in accordance with the present invention also acts as highly protective agent for hydrolytic degradation, in particular long term hydrolytic degradation.
  • the wetting agent in accordance with the present invention is particularly suitable for protecting a gel like low delicate (hydrated) interpenetrating polymer network from irradiation and also provides hydrolytic stability.
  • the method according to the present invention uses a composition and a wetting agent comprising the composition which is mobile and in a liquid state, preferably the wetting agent is an aqueous wetting agent containing fully dissolved gallic acid or an ester, amide or oxadiazole derivative of gallic acid and/or CMC or a salt thereof and provides intimate contact with free moving hydrophilic polymer chains of the coating of a medical device.
  • the composition used in the method in accordance with the present invention is mobile and free flowing at the surface of the coating.
  • composition of the present invention allows preventing or retarding degradation of a functional coating from both, irradiation and hydrolytic degradation.
  • the composition and the wetting agent of the present invention are capable of protecting even polymers such as gel networks, e.g. lightly crosslinked gel networks, and hydrophilic coatings, while in an aqueous environment and under extreme irradiation conditions.
  • the composition and the wetting agent of the present invention further provide hydrolytic stability during the intended shelf-life of a wetted coated product.
  • composition of the present invention can comprise carboxymethyl cellulose or a derivative or salt thereof and/or an antioxidant selected from gallic acid or a derivative thereof.
  • Gallic acid is a benzoic acid having the following structure:
  • the IUPAC name is: 3,4,5-trihydroxybenzoic acid.
  • the derivative of gallic acid of the composition used in the method is an ester, amide or oxadiazole derivative of gallic acid.
  • ester derivative of gallic acid refers to an ester reaction product of an alcohol and gallic acid.
  • amide derivative of gallic acid refers to the reaction product of an amine and gallic acid.
  • oxadiazole derivative of gallic acid refers to the reaction product of oxaidazole and gallic acid.
  • the ester derivative of gallic acid present in the composition which is used in the method is a reaction product of gallic acid and an aliphatic C1 to C16 alcohol, more preferably a reaction product of gallic acid and an aliphatic C1 to C12 alcohol.
  • the ester derivative of gallic acid is selected from propyl gallate, methyl gallate, ethyl gallate, octyl gallate and lauryl gallate or mixtures thereof, in particular, the ester derivative of gallic acid is propyl gallate.
  • aliphatic alcohol refers to a saturated linear or branched alcohol.
  • Propyl gallate is the reaction product of gallic acid and propanol and has the following structure:
  • the amide derivative of gallic acid is selected from gallic N,N-dimethylamide, gallic naphtylamide or mixtures thereof.
  • the oxadiazole derivative of gallic acid has the following structure:
  • gallic acid or a derivative thereof in the composition which is used in the method of the present invention, gallic acid or a derivative thereof is present in an amount of 0.001 to 5% by weight, more preferably 0.01 to 2% by weight, most preferably 0.05 to 0.5% by weight, in particular 0.1 to 0.2% by weight, based on the total weight of the composition. This is the case if only gallic acid or a derivative thereof is present in the composition and no carboxymethyl cellulose.
  • Carboxymethyl cellulose is a cellulose derivative, wherein some of the hydroxyl groups of the glucopyranose monomers that form the cellulose backbone are replaced with carboxymethyl groups (—CH 2 —COOH). It is often used as its sodium salt, sodium carboxymethyl cellulose.
  • Carboxymethyl cellulose has the following structure:
  • the composition comprises a salt of carboxymethyl cellulose, more preferably the sodium salt of carboxymethyl cellulose.
  • sodium carboxymethyl cellulose R of the above structural formula is CH 2 CO 2 Na.
  • Other commonly used names are sodium cellulose glycolate, Na-CMC, cellulose gum, sodium CMC, CAS No 9004-32-4.
  • carboxymethyl cellulose or a derivative or salt thereof is present in an amount of 0.1 to 10% by weight, more preferably 0.2 to 7% by weight, particularly preferably 0.2 to 5% by weight, in particular 1 to 5% by weight, based on the total weight of the composition.
  • carboxymethyl cellulose is present as the sodium salt, i.e. Na-CMC.
  • the composition used in the method of the present invention further comprises an aqueous or oil based base solution or a lipid media or a combination thereof.
  • the aqueous base solution of the composition used in the method is selected from distilled water, deionized water, reverse osmosis water, filtered water or a saline solution. More preferably, the aqueous base solution is a saline solution, in particular a saline solution having physiological osmolarity.
  • the aqueous base solution of the composition used in the method is a saline solution having physiological osmolarity.
  • the saline solution is present in the composition in an amount of 85 to 94% by weight based on the total weight of the composition.
  • the composition used in the method of the present invention is present as a suspension within and/or around the functional coating at least during and after sterilization of the medical device.
  • the term “around” as used herein has the meaning of “in the vicinity” of the coating.
  • the stabilizer is selected from polylactams, such as polyvinylpyrrolidone (PVP), polyurethanes, homo- and copolymers of acrylic and methacrylic acid, polyvinyl alcohols, polyvinylethers, maleic anhydride based copolymers, polyesters, such as polylactides, polyglycolides, polycaprolactones, and polynucleotides, vinylamines, polyethyleneimines, polyethyleneoxides, polycarboxylic acids, polyamides, polyanhydrides, polyphosphazenes, cellulosics, such as methyl cellulose, carboxymethyl cellulose, hydroxymethylcellulose, hydroxyxpropylcellulose and other polysaccharides, such as chitosans, hyaluronic acids, alginates, gelatins, chitins, heparins, and dextrans, polypeptides/proteins, such as collagens
  • PVP polyvinylpyrrolidone
  • a solution enhancer may be added to the composition used in the method of the present invention.
  • the solution enhancer is selected from a polyol, more preferably ethylene glycol, diethylene glycol, propylene glycol, glycerol, in particular propylene glycol.
  • the solution enhancer preferably propylene glycol
  • the solution enhancer is present in the composition of the present invention in an amount of 0.1 to 49.8% by weight, more preferably 1 to 20% by weight, in particular 2 to 10% by weight based on the total weight of the composition.
  • the esters of gallic acid have limited solubility in water, e.g. the solubility of propyl gallate is 3.5 mg/mL. Furthermore, the dissolution rates are slow at room temperature. When adding a polyol such as propylene glycol, the dissolution rate significantly increases without the necessity of heat.
  • the weight ratio of water or saline solution to propylene glycol is 1.0 to 0.3 to 1.0 to 1.3, preferably 1.0:0.7.
  • propyl gallate can precipitate out of the solution after cooling to form low-order structure entities that resemble needle lattice structures.
  • the addition of propylene glycol prevents or eliminates the necessity of elevating the temperature of the solution. Adding a component to a solution at an elevated temperature can generate a super-saturated solution, i.e a solution which contains more of the dissolved component than it would under normal room temperature conditions. When cooling a super-saturated solution, the dissolved component can precipitate out of the solution.
  • the polyol e.g. propylene glycol, additionally functions as antimicrobial and antifungal agent and therefore delivers antimicrobial and antifungal properties to the composition used in the method of the present invention.
  • the buffer solution has a pH of 2.0 to 7.4, more preferably 3.0 to 6.5, in particular 3.0 to 4.0.
  • the buffer solution is added to generate solution stability with regard to pH and prevent the esters of gallic acid from recrystallization.
  • Suitable buffers include monocarboxylic acids such as formic acid, acetic acid, propionic acid, 3-hydroxypropionic acid, 2,3-dihydroxypropionic acid, gluconic acid, benzoic acid, cinnamic acid, lactic acid, mandelic acid, glycolic acid, phenylacetic acid, chlorobenzoic acid, naphtoic acid, toluic acid, N-acetylglycine; dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, phthalic acid, isophthalic acid, terephthalic acid, malic acid, tartaric acid, itaconic acid, and fumaric acid; tri- and tetracarboxylic acids such as citric acid and 1,2,3,4-butanetetracarboxylic acid; amino acids such as tryptophan, aspartic acid, glutamic acid, aminobenzoic acid, glycylglycine
  • the composition used in the method of the present invention can comprise 0.01 to 2% by weight of propyl gallate, 0.1 to 40% by weight of PVP, and 0.1 to 49.8% by weight of propylene glycol; more preferably 0.05 to 0.5% by weight of propyl gallate, 3 to 20% by weight of PVP, and 1 to 20% by weight of propylene glycol; in particular 0.1 to 0.2% by weight of propyl gallate, 4 to 12% by weight of PVP, and 2 to 10% by weight of propylene glycol.
  • Particularly preferable is a composition comprising 0.1 to 0.2% by weight of propyl gallate, 4 to 12% by weight of PVP, and 2 to 10% by weight of propylene glycol and a buffer having a pH of 4 to 5.
  • the composition in accordance with the present invention comprises 0.1 to 10% by weight of sodium carboxymethyl cellulose, 0 to 1% by weight of propyl gallate, and 1 to 20% by weight of propylene glycol; more preferably 0.2 to 7% by weight of sodium carboxymethyl cellulose, 0.01 to 1% by weight of propyl gallate, and 1 to 15% by weight of propylene glycol; in particular 0.2 to 5% by weight of sodium carboxymethyl cellulose, 0.02 to 0.2% by weight of propyl gallate, and 2 to 10% by weight of propylene glycol, based on the total weight of the composition.
  • composition comprising 0.2 to 2% by weight of sodium carboxymethyl cellulose, 0.02 to 0.2% by weight of propyl gallate, and 2 to 10% by weight of propylene glycol, based on the total weight of the composition, and a buffer having a pH of 4 to 5.
  • a composition comprising 2 to 5% by weight of sodium carboxymethyl cellulose, 0% by weight of propyl gallate, and 2 to 10% by weight of propylene glycol, based on the total weight of the composition, and a buffer having a pH of 4 to 5.
  • the composition used in the method of the present invention further comprises an antibacterial agent such as a silver salt, an acceptable iodine source such as povidone iodine, chlorhexidine salts such as the gluconate, actetate, hydrochloride or quaternary antibacterial agents such as benzalkonium chloride or other antiseptics or antibiotics.
  • an antibacterial agent such as a silver salt, an acceptable iodine source such as povidone iodine, chlorhexidine salts such as the gluconate, actetate, hydrochloride or quaternary antibacterial agents such as benzalkonium chloride or other antiseptics or antibiotics.
  • an antibacterial agent such as a silver salt, an acceptable iodine source such as povidone iodine, chlorhexidine salts such as the gluconate, actetate, hydrochloride or quaternary antibacterial agents such as benzalkonium chloride or other antiseptics or antibiotics.
  • composition according to the present invention may further comprise an osmolarity increasing agent such as urea, sodium chloride and/or any salt or organic low molecular weight compound being physiological acceptable and non-irritating for adjusting the ion strength of the coating approximately to the physiological range, the coating preferably being isotonic in use.
  • the composition according to the present invention may also comprise preservatives and pharmaceuticals such as antimicrobial agents and antithrombogenic agents or plasticizers.
  • the energy dose of radiation during radiation sterilization is in a range from 1 to 50 kGy, preferably 15 kGy to 45 kGy, more preferably 25 kGy to 45 kGy. Even at high radiation energies up to 50 kGy the composition used in the method of the present invention prevents or retards the degradation of the functional coating on the medical device due to reactive species formed during exposure to radiation.
  • the method additionally comprises the following steps:
  • the medical device is a catheter.
  • the medical device produced by the method and having a functional coating may be any device that should be able to move against body tissue such as an inner wall of a body vessel or the outer surface of the eye, for example a medical tubing, guidewire, canula, stent, stent graft, anastomotic connector, synthetic patch, lead electrode, needle, sensor, surgical instrument, angioplastic balloon, wound drain, shunt, tubing, infusion sleeve, urethal insert, pellet, implant, blood oxygenator, pump, vascular graft, vascular access port, heart valve, annuloplasty ring, suture, surgical clip, surgical staple, pacemaker, implantable defibrillator, neurostimulator, orthopedic device, cerebrospinal fluid shunt, implantable drug pump, spinal cage, artificial disc, replacement device for nucleus pulposus, ear tube, intraocular lens, tubing used in minimally invasive surgery, it is preferred that the medical
  • the functional coating is a hydrophilic coating.
  • the term “functional coating” also includes antithrombogenic coatings, gel coatings, hydrophilic polymer coatings, polyvinylalcohol coatings, coatings for contact lenses, coatings based on water soluble polymers used especially in drug delivery systems such as hydrogels, cellulose ethers, povidone, polyethylene glycol, polyacrylamides, polyacrylic acid copolymers, Polylactide-co-Glycolide (PGLA) and derivatives thereof.
  • PGLA Polylactide-co-Glycolide
  • the catheter comprises a catheter shaft which is coated with a hydrophilic coating at least along its insertable length and which is tightly surrounded by a retractable sleeve and wherein the retractable sleeve and/or the catheter have a liquid-tight closure at a distal end and at a proximal end so that any liquid present in the retractable sleeve or the catheter shaft remains within the retractable sleeve and the catheter as long as the closure is not broken.
  • the composition/wetting agent is needed to activate the hydrophilic coating and it can be ensured that the hydrophilic coating stays in the wetted condition during storage.
  • the composition according to the present invention is able to prevent or retard degradation of functional coatings on a medical device.
  • the composition of the present invention can be easily prepared from non-toxic components and can be used during radiation sterilization. When used during the sterilization of a medical device, no degradation of the functional coating on the medical device from reactive species generated during exposure of radiation occurs in the presence of the composition of the present invention.
  • composition in accordance with the present invention is also able to prevent or retard hydrolytic degradation and is particularly suitable for wetted environments.
  • Propyl gallate is only slightly soluble in water but, with the addition of propylene glycol, the solubility of propyl gallate increases. Propylene glycol has a great affinity to water and is also a viable alternative additive to glycerol from a cost perspective.
  • PVP polyvinylpyrrolidone
  • K60 45% in H 2 O
  • surfactants such as Tween 20 and 80 (non-ionic agent supplied by Sigma Aldrich)
  • buffer solutions pH 4.00 (20° C.) or citric acid/sodium hydroxide/hydrogen chloride supplied by Merck Chemicals KGaA
  • citric acid/sodium hydroxide/hydrogen chloride supplied by Merck Chemicals KGaA may optionally be added after the mixing of the propyl gallate has been accomplished.
  • Tween 20 and 80 non-ionic agent supplied by Sigma Aldrich
  • buffer solutions pH 4.00 (20° C.
  • Extruded polymer shafts reflecting a diameter of 4.5 mm with an ID of 3.0 mm were selected for the testing. These shafts had been dipped and cured which resulted in a uniform hydrophilic coating along the polymeric tube substrate. It is important to ensure that the same processing parameters of dipping and UV curing of the coating were maintained so as to eliminate any variability in coating integrity.
  • the shaft material used for these series of trials was polyurethane block copolymers and plasticized polyvinyl chloride. The shafts were placed on a cutting mat and the polymeric coated tubes were cut to a length of approximately 200 mm with a sharp blade.
  • a stainless steel mandrel of appropriate diameter to the inner lumen of the coated test specimen was completely inserted into the test specimen.
  • the tube was positioned with a clamp on the section having a clean level cut (the angled tube cut faced the water container of the friction testing machine).
  • PG propyl gallate
  • the COF can be adjusted by adding additional additives or by selecting the carrier solution and/or the pH.
  • Formulations based on propyl gallate (PG) and sodium carboxymethyl cellulose (Na-CMC) were developed to further enhance the wetting agent performance.
  • the samples were prepared with polypropylene glycol and buffer content maintained constant throughout the study to demonstrate the influence of the main stabilizing component ingredients, i.e. propyl gallate and sodium carboxymethyl cellulose.
  • the coating integrity and hydrolytic stability of the coating were tested after subjecting the hydrated specimens to 45 kGy gamma irradiation dosages.
  • the primary objective of the wetting agent is to protect the hydrated hydrophilic coating during the sterilization cycles and secondarily, to provide hydrolytic stability to the coating, reflecting real-world shelf-life product indication.
  • the hydrolytic stability of the coating was assessed by interpreting the coating frictional stability performance over the 25 frictional cycles after subjecting coated hydrated specimens to accelerated aging for periods of 15 days (T15) and 30 days (T30), respectively, at an ageing temperatures of 50° C. All specimens were subjected to 45 kGy irradiation dosages. Time Zero (T0) directly after exposure captures the isolated effects of gamma irradiation on the coating integrity.
  • FIG. 1 shows a first embodiment of the ready-to-use medical device produced with the method of the present invention
  • FIG. 2 shows a detail of the medical device of FIG. 1 .
  • FIG. 3 shows a second embodiment of a ready-to-use medical device produced with the method of the present invention
  • FIG. 4 shows a detail of the medical device of FIG. 3 .
  • FIG. 1 a first embodiment of a ready-to-use medical device produced with the method of the present invention is shown.
  • the ready-to-use medical device of the first embodiment is a catheter 1 used for intermittent catheterization.
  • the catheter 1 comprises a catheter shaft 2 with a catheter tip 3 at a distal end 5 and a funnel 4 at a proximal end 6 .
  • the catheter shaft 2 is covered with a hydrophilic coating at least along its insertable length.
  • the catheter shaft 2 is surrounded by a retractable sleeve 7 .
  • the retractable sleeve 7 is fixed to the catheter shaft 2 .
  • the retractable sleeve can also be fixed to the funnel.
  • the distal end 6 of the catheter 1 with the funnel 4 and the cap 10 is shown in more detail in FIG. 2 .
  • the cap 10 is plugged in the funnel 4 so that a liquid-tight closure is achieved.
  • the wetting agent is inserted into the retractable sleeve 7 via the plug 9 . Because the plug 9 and the introduction aid 8 as well as the funnel 4 and the cap 10 form liquid-tight closures, the wetting agent remains inside the retractable sleeve 7 and/or the catheter shaft 2 and the outside of the retractable sleeve 7 as well as the outside of the funnel 4 remain dry and can be easily gripped by a user.
  • This catheter set can then be placed in a vapour-tight package (not shown).
  • the distal end 29 of the retractable sleeve 27 is connected to an introduction aid 28 which is slidably arranged on the catheter shaft 22 .
  • the introduction aid 28 is pushed back on the catheter shaft 22 so that the retractable sleeve 27 is retracted and the catheter shaft 22 is exposed.
  • the catheter 21 with the catheter shaft 22 and the retractable sleeve 27 arranged thereon is arranged in a vapour-tight package 30 . Furthermore, a wetting agent comprising the composition as described above is inserted in the package 30 .
  • the catheter shaft 2 , 22 is coated with a hydrophilic coating, the functional coating, at least along its insertable length.
  • the insertable length of the catheter shaft 2 , 22 is the length of the catheter shaft which is inserted in the urethra when the catheter is used.
  • the wetting agent contacts and activates the hydrophilic coating of the catheter shaft 2 , 22 .
  • the wetting agent comprises the composition as described above with carboxymethyl cellulose or a derivative or a salt thereof and/or an antioxidant selected from gallic acid or a derivative thereof as described above.
  • the catheter shaft 2 , 22 with the catheter tip 3 , 23 and the funnel 4 , 24 is produced.
  • the catheter shaft 2 , 22 is coated with a hydrophilic coating.
  • the retractable sleeve 7 , 27 is arranged around the catheter shaft 2 , 22 and is connected to the catheter shaft 2 , 22 or the funnel 4 , 24 at the proximal end of the catheter 1 , 21 .
  • an introduction aid 8 , 28 is slidably arranged on the catheter shaft 2 , 22 and connected to the distal end of the retractable sleeve 7 , 27 .
  • the funnel 4 is closed with the cap 10 and the plug 9 with the wetting agent contained therein is connected to the introduction aid 8 .
  • the complete assembly is then placed in a vapour-tight package (not shown).
  • the wetting agent comprises the composition as described above.
  • the wetting agent is brought into contact with the hydrophilic coating of the catheter shaft 2 so that the hydrophilic coating is activated.
  • the complete package is then submitted to radiation, for example ⁇ -irradiation (see page 1 , second to last paragraph), so that all components are sterilized. Because the wetting agent comprises a composition as described above, degradation of the hydrophilic coating during sterilization and storage is avoided.
  • the catheter 21 comprising the catheter shaft 22 , the catheter tip 23 , the funnel 24 and the retractable sleeve 27 is placed in a vapour-tight package 30 .
  • the funnel 24 and the introduction aid 8 are open.
  • the wetting agent comprising the composition as described above is added to the package 30 .
  • the wetting agent is brought into contact with a hydrophilic coating of the catheter shaft 22 so that the hydrophilic coating is activated.
  • the entire package is submitted to radiation sterilization, for example ⁇ -irradiation, so that all components are sterilized.
  • the energy dose of radiation during radiation sterilization lies in a range from 1 kGy to 50 kGy, preferably 15 kGy to 45 kGy, more preferably 25 kGy to 45 kGy.

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