WO1999008718A2 - Bioresorbable compositions for implantable prostheses - Google Patents

Bioresorbable compositions for implantable prostheses Download PDF

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Publication number
WO1999008718A2
WO1999008718A2 PCT/US1998/016933 US9816933W WO9908718A2 WO 1999008718 A2 WO1999008718 A2 WO 1999008718A2 US 9816933 W US9816933 W US 9816933W WO 9908718 A2 WO9908718 A2 WO 9908718A2
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WO
WIPO (PCT)
Prior art keywords
composition
poly
agents
group
medical device
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1998/016933
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English (en)
French (fr)
Other versions
WO1999008718A3 (en
Inventor
Gary L. Loomis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boston Scientific Scimed Inc
Original Assignee
Meadox Medicals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Meadox Medicals Inc filed Critical Meadox Medicals Inc
Priority to EP98938491A priority Critical patent/EP1019096B1/en
Priority to CA002303807A priority patent/CA2303807C/en
Priority to JP2000509454A priority patent/JP5227487B2/ja
Priority to DE69826882T priority patent/DE69826882T2/de
Priority to AT98938491T priority patent/ATE278423T1/de
Priority to AU87008/98A priority patent/AU8700898A/en
Publication of WO1999008718A2 publication Critical patent/WO1999008718A2/en
Publication of WO1999008718A3 publication Critical patent/WO1999008718A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/18—Block or graft polymers
    • C08G64/183—Block or graft polymers containing polyether sequences
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • A61K9/204—Polyesters, e.g. poly(lactide-co-glycolide)
    • 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
    • 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
    • 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
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • 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
    • A61L27/58—Materials at least partially resorbable by the body
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • A61L2300/406—Antibiotics
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
    • A61L2300/408—Virucides, spermicides
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/41—Anti-inflammatory agents, e.g. NSAIDs
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/416—Anti-neoplastic or anti-proliferative or anti-restenosis or anti-angiogenic agents, e.g. paclitaxel, sirolimus
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/42—Anti-thrombotic agents, anticoagulants, anti-platelet agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S623/00—Prosthesis, i.e. artificial body members, parts thereof, or aids and accessories therefor
    • Y10S623/924—Material characteristic

Definitions

  • This invention relates generally to coating compositions for medical devices. More
  • the present invention relates to cross-linked compositions formed from a
  • water insoluble copolymer having a bioresorbable region, a hydrophilic region and at least
  • hydrogels which are useful as sealants for
  • hydrogels can be used as delivery vehicles for therapeutic agents. Medical devices coated
  • composition as tissue ingrowth encapsulates the prosthesis.
  • Natural materials such as collagen and gelatin, have been widely used on textile
  • compositions are beneficial in that they are able to seal an implantable device without the
  • fibrin an insoluble protein
  • One such drawback is the difficulty in producing consistent coatings
  • biologically-based sealant compositions can cause inflammation, as well as infection at or
  • copolymers are disclosed to be water-soluble so that the body can excrete the degraded
  • compositions are uncrosslinked and, as a
  • compositions generally require the presence of crystalline segments to retain their
  • compositions are disclosed for use as resorbable
  • compositions are somewhat hydrophilic, they do not form
  • compositions whose integrity can be controlled through crosslinking For example, U.S. Patent Nos. 5,410,016 and 5,529,914 to Hubbell et al. disclose water-soluble systems
  • hydrolytically labile extensions can be a
  • poly( ⁇ -hydroxy acid) such as, polygly colic acid or polylactic acid. See, Sawhney, A.S.,
  • block copolymers having sequentially ordered blocks of polylactide and/or polyglycolide
  • composition R-(A-B-A-L) ⁇ -A-B-A-R, where A is a polyhydroxy acid, such as
  • polylactide polyglycolide or a copolymer thereof
  • B is an oligomeric diol or diamine
  • L is a diacyl residue derived from an aromatic diacyl halide or diisocyanate and R
  • compositions described by these references are intended to be rapidly biodegraded by the
  • the present invention is a
  • This composition includes a water-insoluble copolymer which
  • This composition includes a hydrogel formed from the crosslinking of a polymer containing a
  • bioresorbable region a hydrophilic region, a plurality of crosslinkable functional groups
  • This process includes providing an aqueous emulsion of a water-
  • This water-insoluble copolymer includes a bioresorbable region, a
  • hydrophilic region a plurality of crosslinkable functional groups per polymer chain and a
  • crosslinking agent Activation of the crosslinking agent crosslinks the copolymer
  • composition composition and forms the hydrogel.
  • the hydrogel is formed from an
  • aqueous emulsion which includes a water-insoluble copolymer having a bioresorbable
  • This process includes applying the hydrogel to the medical
  • the present invention is directed to covalently crosslinkable compositions formed
  • copolymers of the present invention include a
  • Hydrogels formed from the compositions of the present invention can be any suitable hydrogel formed from the compositions of the present invention. Hydrogels formed from the compositions of the present invention can be any hydrogel formed from the compositions of the present invention.
  • copolymers of the present invention are multi -block copolymers including, for
  • di-block copolymers examples, di-block copolymers, tri-block copolymers, star copolymers, and the like.
  • di-block copolymers examples, di-block copolymers, tri-block copolymers, star copolymers, and the like.
  • a typical tri-block copolymer of the present invention may
  • A is the bioresorbable region
  • B is the hydrophilic region
  • x is the
  • compositions has
  • x is from about 10 to about 50 and y is from about 50 to about 300, so long as the
  • composition remains water-insoluble as a whole.
  • composition be water-insoluble.
  • water-insoluble water-insoluble
  • the copolymer may be hydrophilic or even water-soluble, however, the copolymer
  • the water-insoluble copolymer includes a bioresorbable region.
  • bioresorbable means that this region is
  • the bioresorbable region is preferably hydrophobic. In another preferred embodiment
  • the bioresorbable region may be designed to be hydrophilic so long
  • the copolymer composition as a whole is not rendered water-soluble.
  • bioresorbable region is designed based on the requirement that the copolymer, as a whole,
  • copolymers of the present invention form a stable aqueous emulsion.
  • emulsifying refer to the ability of the copolymers of the present composition to form an
  • emulsion i.e., a colloidal suspension of one liquid in another, without the requirement of
  • emulsifying agents are not
  • copolymer composition water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently water-insoluble. Furthermore these compositions are sufficiently
  • hydrophilic to form a hydrogel in aqueous environments when crosslinked.
  • hydrogels as set forth in more detail below, can form a fluid-tight barrier when applied to
  • composition of the present invention will of course vary depending upon the intended
  • implantable prosthesis the site of implantation, as well as other factors.
  • the site of implantation the site of implantation, as well as other factors.
  • composition of the present invention remains substantially water-insoluble when the ratio
  • bioresorbable region of the present invention can be designed to be
  • hydrolytically and/or enzymatically cleavable hydrolytically and/or enzymatically cleavable.
  • hydrolytically cleavable refers to the susceptibility of the copolymer, especially the
  • bioresorbable region to hydrolysis in water or a water-containing environment.
  • enzymes as used herein refers to the susceptibility of the copolymer
  • bioresorbable region especially the bioresorbable region, to cleavage by endogenous or exogenous enzymes.
  • the bioresorbable region includes
  • bioresorbable region can also be, for example, a poly(hydroxy)
  • acids include, for example, polylactic acid, polyglycolic acid, polycaproic acid,
  • polybutyric acid polyvaleric acid and copolymers and mixtures thereof.
  • the present composition also includes a hydrophilic region.
  • hydrophilic is used in the classical sense of a material
  • composition contains an
  • this region is designed and/or selected so that the composition as a
  • the hydrophilic region When placed within the body, the hydrophilic region can be processed into
  • hydrophilic region can include
  • polyethers without limitation, for example polyethers, polyalkylene oxides, polyols, poly(vinyl)
  • hydrophilic peptides, proteins and copolymers and mixtures thereof. Furthermore, the hydrophilic
  • region can also be, for example, a poly(alkylene) oxide.
  • poly(alkylene) oxides can be any poly(alkylene) oxide.
  • poly(ethylene) oxide examples include, for example, poly(ethylene) oxide, poly(propylene) oxide and mixtures and
  • composition of the present invention also includes a
  • Any crosslinkable functional group can be any crosslinkable functional group. Any crosslinkable functional group can be any crosslinkable functional group. Any crosslinkable functional group can be any crosslinkable functional group.
  • crosslinkable functional groups of the present invention are
  • acrylates include without limitation, for example, acrylates, methacrylates, butenates, maleates, allyl
  • the crosslinking agent is a free
  • radical initiator such as for example, 2,2'-Azobis (N,N'dimethyleneisobutyramidine)
  • crosslinkable functional groups can be present at any point along the polymer
  • crosslinkable functional groups can be present in the polymer chain of the present invention in numbers greater than two, so long as the
  • At least two olefmically unsaturated functional groups are
  • unsaturated functional groups can be positioned anywhere within the polymer chain of the
  • unsaturated group is positioned at both terminal ends of the polymer chain.
  • crosslinkable functional groups are activated to crosslink the
  • initiators can include, for example, high energy radiation, thermal radiation and/or visible
  • composition of the present invention can also include free radical initiators.
  • Such free radical initiators can include, for example, a peroxide or an azo compound.
  • the composition is crosslinked in an aqueous medium.
  • the copolymer composition when crosslinked, is able to form a hydrogel.
  • the hydrogels of the present invention are polymeric materials that swell in water without
  • compositions have properties intermediate between liquid and solid states.
  • Hydrogels also have properties intermediate between liquid and solid states.
  • hydrogels are water-swollen, three-dimensional networks of hydrophilic
  • hydrogel compositions are not as transient as, and are more controllable
  • a therapeutic agent such as for example a
  • composition can be used to target therapeutic agents to specific sites in the body.
  • the present composition can be engineered to bioresorb at a certain rate by
  • the present compositions are able to
  • block copolymer is bioresorbed.
  • Any drug or bio-active agent may be incorporated into the composition of the invention.
  • Suitable drugs or bio-active agents may be any suitable drugs or bio-active agents.
  • thrombo-resistant agents include, for example, without limitation, thrombo-resistant agents, antibiotic agents, anti-
  • tumor agents antiviral agents, anti-angiogenic agents, angiogenic agents, anti-
  • Useful thrombo-resistant agents can include, for example, heparin, heparin sulfate,
  • hirudin hyaluronic acid, chondroitin sulfate, dermatan sulfate, keratin sulfate, lytic agents,
  • urokinase and streptokinase their homologs, analogs, fragments, derivatives and
  • Useful antibiotics can include, for example, penicillins, cephalosporins,
  • vancomycins aminoglycosides, quinolones, polymyxins, erythromycins, tetracyclines,
  • Useful anti-tumor agents can include, for example, paclitaxel, docetaxel, alkylating
  • agents including mechlorethamine, chlorambucil, cyclophosphamide, melphalan and
  • ifosfamide antimetabolites including methotrexate, 6-mercaptopurine, 5-fluorouracil and
  • doxorubicin including doxorubicin, daunomycin, bleomycin, and mitomycin; nitrosureas including
  • modifiers including interferon; enzymes including asparaginase; and hormones including tamoxifen and flutamide their homologs, .analogs, fragments, derivatives, pharmaceutical
  • Useful .anti-viral agents can include, for example, amantadines, rimantadines,
  • ribavirins idoxuridines, vidarabines, trifluridines, acyclovirs, ganciclovirs, zidovudines,
  • composition includes a hydrogel which is formed from the crosslinking of a polymer
  • bioresorbable coating composition of the present invention can be applied as
  • bioresorbable coatings are capable of rendering fluid-tight porous medical devices such as
  • conduits for purposes of:
  • the term "fluid-tight" refers to the specific porosity of a material
  • V is the volume of water collected in ml/min and A is the surface area of the graft
  • a substantially fluid-tight graft means a graft with a specific porosity
  • Implantable materials useful in the present invention can include, for example
  • polymeric material can include, for example, olefin polymers including polyethylene,
  • polypropylene polyvinyl chloride, polytetrafluoroethylene, fluorinated ethylene propylene
  • copolymer polyvinyl acetate, polystyrene, poly(ethylene terephthalate), polyurethane,
  • polyurea silicone rubbers, polyamides, polycarbonates, polyaldehydes, natural rubbers,
  • polyester copolymers styrene-butadiene copolymers and combinations thereof.
  • polymeric implantable materials can include, for example, ceramics, metals, inorganic
  • implantable substrate material of the present invention are intended to be exemplary only and should not be construed to limit in any way the types of materials
  • implantable materials are used to manufacture medical
  • these medical devices are contemplated. Preferably these medical devices are vascular or endovascular
  • Useful vascular or endovascular grafts include those which are knitted, braided or
  • woven textiles may have velour or double velour surfaces.
  • device can be manufactured from an extruded polymer, such as polytetrafluoroethylene
  • PTFE polyethylene terephthalate
  • PET polyethylene terephthalate
  • the medical device may be a catheter, a
  • composition of the present invention imparts increased bio-compatibility to one or more
  • the present composition includes a drug or bio-active
  • hydrophilic region of the present composition can impart increased
  • This process includes: (i) providing an aqueous emulsion of a water-
  • insoluble copolymer which contains a bioresorbable region, a hydrophilic region, a
  • crosslinkable functional groups can be, but are not limited to, olefinically unsaturated
  • the crosslinking agent can be a free radical initiator, an
  • crosslinking agent can be, for example,
  • this hydrogel is
  • copolymer includes a bioresorbable region, a hydrophilic region, a plurality of
  • crosslinkable functional groups per polymer chain and a crosslinking agent Accordingly,
  • this process includes applying the hydrogel to the medical device and then activating the
  • crosslinking agent in a humid environment.
  • crosslinking agent can be activated in both humid and non-humid
  • the activation take place in humid environments.
  • the humid environment contains from about 20% to about 100% water. More
  • the humid environment contains from about 60% to about 100% water.
  • hydrogels formed by this process can be packaged and stored in a variety of materials
  • the hydrogel can be maintained in a hydrated state for an extended
  • the hydrogel can be dehydrated and stored in an essentially
  • a therapeutic agent such as for example, a drug or bio-
  • active agent can be added to the emulsion for targeted, timed release of such agents in the
  • Polymer A according to the present invention was synthesized as
  • Polymer B Another polymer (Polymer B) according to the present invention was synthesized
  • the resulting Polymer B was a waxy solid which was
  • Polymer C according to the present invention was synthesized as set forth in
  • Example 1 with the following exceptions.
  • the amount of d, 1-lactide was increased to 71.2
  • the resulting Polymer C was an oil which was substantially water-insoluble.
  • Polymer D according to the present invention was synthesized as set forth in
  • Example 1 with the following exceptions.
  • the amount of d, 1-lactide was increased to 22.5
  • An aqueous emulsion (20% solids) was prepared by dispersing Polymer D and
  • VazoTM 044 (13.4 mg Vazo/1.0 gm. polymer) in water with rapid stirring. The mixture
  • the impregnated fabric was then passed twice through a soft rubber wringer to
  • the water porosity of the coated medical fabric of Example 6 was determined in a
  • Example 6 coated medical fabric of Example 6 was placed over a hole, and a metal plate, containing a
  • A the cross-sectional area in cm 2 of the hole.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Transplantation (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Dispersion Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Materials For Medical Uses (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/US1998/016933 1997-08-18 1998-08-14 Bioresorbable compositions for implantable prostheses Ceased WO1999008718A2 (en)

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EP98938491A EP1019096B1 (en) 1997-08-18 1998-08-14 Bioresorbable compositions for implantable prostheses
CA002303807A CA2303807C (en) 1997-08-18 1998-08-14 Bioresorbable compositions for implantable prostheses
JP2000509454A JP5227487B2 (ja) 1997-08-18 1998-08-14 移植可能なプロテーゼ用の生体溶解吸収性組成物
DE69826882T DE69826882T2 (de) 1997-08-18 1998-08-14 Bioresorbierbare zusammensetzungen für implantierfähige prothesen
AT98938491T ATE278423T1 (de) 1997-08-18 1998-08-14 Bioresorbierbare zusammensetzungen für implantierfähige prothesen
AU87008/98A AU8700898A (en) 1997-08-18 1998-08-14 Bioresorbable compositions for implantable prostheses

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US08/914,130 US5854382A (en) 1997-08-18 1997-08-18 Bioresorbable compositions for implantable prostheses

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US5854382A (en) 1998-12-29
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US6028164A (en) 2000-02-22
US6005020A (en) 1999-12-21
US6403758B1 (en) 2002-06-11
DE69826882D1 (de) 2004-11-11
DE69826882T2 (de) 2005-11-10
EP1019096A2 (en) 2000-07-19
ATE278423T1 (de) 2004-10-15
CA2303807C (en) 2008-01-22
JP2001514931A (ja) 2001-09-18
EP1019096B1 (en) 2004-10-06
CA2303807A1 (en) 1999-02-25
JP5227487B2 (ja) 2013-07-03
WO1999008718A3 (en) 1999-05-20

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