WO2009099768A2 - Biodegradable coatings for implantable medical devices - Google Patents
Biodegradable coatings for implantable medical devices Download PDFInfo
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- WO2009099768A2 WO2009099768A2 PCT/US2009/031691 US2009031691W WO2009099768A2 WO 2009099768 A2 WO2009099768 A2 WO 2009099768A2 US 2009031691 W US2009031691 W US 2009031691W WO 2009099768 A2 WO2009099768 A2 WO 2009099768A2
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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
- 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
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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
- 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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L31/148—Materials at least partially resorbable by the body
-
- 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
-
- 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
-
- 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
-
- 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
- A61L27/14—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
- 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
Definitions
- the present invention is directed to biodegradable coatings for implantable medical devices.
- Systemic delivery involves administering a therapeutic agent at a discrete location followed by the agent migrating throughout the patient's body including, of course, to the afflicted organ or area of the vasculature. But to achieve a therapeutic amount of the agent at the afflicted site, an initial dose substantially greater than the therapeutic amount must be administered to account for the dilution the agent undergoes as it travels through the body.
- Systemic delivery introduces the therapeutic agent in two ways: into the digestive tract (enteral administration) or into the vascular system (parenteral administration), either directly, such as injection into a vein or an artery, or indirectly, such as injection into a muscle or into the bone marrow.
- enteric administration factors such as a compound's solubility, its stability in the acidic environs of the stomach and its ability to permeate the intestinal wall all affect drug absorption and therefore its bioavailability.
- factors such as enzymatic degradation, lipophilic/hydrophilic partitioning coefficient, lifetime in circulation, protein binding, etc. will affect the agent's bioavailability.
- local delivery comprises administering the therapeutic agent directly to the afflicted site.
- the ADMET factors tend to be less important than with systemic administration because administration is essentially directly to the treatment site.
- the initial dose can be at or very close to the therapeutic amount.
- some of the locally delivered therapeutic agent may diffuse over a wider region, but that is not the intent of localized delivery, and the diffused portion's concentration will ordinarily be sub-therapeutic, i.e., too low to have a therapeutic effect.
- localized delivery of therapeutic agents is currently considered a state-of-the-art approach to the treatment of many diseases such as cancer and atherosclerosis.
- Localized delivery of therapeutic agents may be accomplished using implantable medical devices. Coating implantable medical devices with therapeutic agents, however, is not without problems.
- the family of mussel adhesive proteins is unique in that they bond to a large variety of substrates in an aqueous environment. These proteins share numerous molecular motifs, however, approximately 25% of amino acids in a particular mussel adhesive protein is the modified amino acid 3,4-dihydroxyphenyl-L-alanine (DOPA). It has further been determined that mussel adhesion to rocks, wood and metal is due in large part to DOPA. It has been found, however, that the portion of DOPA responsible for the remarkable adhesive capability of these polymers is the 3,4-dihydroxyphenyl group.
- DOPA 3,4-dihydroxyphenyl-L-alanine
- the present invention takes advantage of the strong binding properties of 3,4-dihydroxyphenyl, and 2,3- dihydroxyphenyl, to provide novel biodegradable coatings, primarily for use as primer coatings for implantable medical devices, particularly bare metal implantable medical devices.
- the present invention relates to a biodegradable coating for an implantable medical device that includes a biodegradable polymer functionalized with an ortho- dihydroxyphenyl compound, the overall structure having the formula:
- X is a linker group and R is the biodegradable polymer.
- R includes a polyester which can be selected from a group that includes a poly(glycolide), poly(D,L-lactide), poly(L-lactide), poly(D,L-lactide-co- glycolide), poly(caprolactone), poly(dioxanone), poly(glycolide-co-trimethylenecarbonate) and copolymers thereof.
- R includes a poly(esteramide), poly(tyrosine-derived carbonate), a poly(tyrosine-derived ester), a poly(tyrosine- ⁇ -hydroxyacid), a poly(orthoester) or a biodegradable polyurethane.
- R includes a poly(depsipeptide) which in some aspects can have the general formula:
- the amino acid can be selected from the group consisting of aspartic acid, glutamic acid, lysine, cysteine, serine, threonine and tyrosine.
- hydroxy acid 1, hydroxy acid 2 and hydroxy acid 3 can be independently selected from a group that includes glycolic acid, L-lactic acid, D-lactic acid, D,L-lactic acid, meso-lactic acid, caprolactone, dioxanone, ⁇ -butyrolactone, ⁇ -propiolactone and ⁇ - valerolactone.
- the linker group can include between 1 and 16 carbon atoms.
- the linker group is linear, branched, unsaturated or cycloaliphatic.
- the linker group comprises an ester, an amide, an ether, an anhydride, a sulfoester, a thioether, a sulfone, a phosphonate, a phosphoester, a carbonate, an imino-carbonate, an acetal, a ketal, an imine, an ortho-ester, a sulfamide or a urethane bond.
- biodegradable polymer can be functionalized with two ortho-dihydroxyphenyl compounds, the overall structure having the formula:
- the biodegradable polymer can be functionalized with multiple ortho-dihydroxyphenyl compounds, the overall structure having the formula: r-
- X independently comprises a linear, branched, unsaturated or cycloaliphatic linker.
- Another aspect of the invention relates to an implantable medical device that includes a coating according to the invention.
- the implantable medical device can be a stent.
- the present invention provides a biodegradable coating for an implantable medical device that includes a biodegradable polymer functionalized with an ortho- dihydroxyphenyl compound, the overall structure having formula I:
- a biodegradable polymer can be functionalized with a different ortho-dihydroxyphenyl compound, the overall structure having formula II:
- biodegradable refers to materials that are capable of being degraded or absorbed when exposed to bodily fluids such as blood, and components thereof such as enzymes or oxidative species, and that can be gradually absorbed and/or eliminated by the body.
- R includes a polyester which can be selected from a group that includes a poly(glycolide), poly(D,L-lactide), poly(L-lactide), poly(D,L-lactide-co- glycolide), poly(caprolactone), poly(dioxanone), poly(glycolide-co-trimethylenecarbonate) and copolymers thereof.
- the R group can be chosen to be compatible with the reservoir layer polymer.
- a drug reservoir layer includes poly(D,L-lactide)
- a primer layer would be chosen, without limitation, to also include poly(D,L-lactide), an example of which is shown by formula III.
- This polymer involves ring-opening polymerization using D,L- lactide and glycolic acid as the initiator. This yields an acid functional poly(D,L-lactide). Dopamine is then coupled to the carboxyl endgroup, methods of which are known to those skilled in the art.
- the polymer of formula III can attach to a metal surface, e.g., a bare metal stent, by ortho-dihydroxyphenyl endpoint attachment. If the polyester polymer segment is too large however, it is unlikely that the ortho-dihydroxyphenyl would effectively coordinate with the metal surface. Thus, the polymer will be chosen to be less than 20,000 Daltons.
- an ortho-dihydrophenyl moiety can be present at both termini of a biodegradable polymer, as shown by formula IV:
- Ri may be a C 2 to Ci ⁇ linear, branched, unsaturated or cyclic hydrocarbon.
- Biodegradable primers containing a much higher number of ortho-dihydroxy phenyl groups are also encompassed by the present invention.
- the biodegradable polymer can be functionalized with multiple ortho-dihydroxyphenyl compounds having an overall structure with the formula: r-
- X independently comprises a linear, branched, unsaturated or cycloaliphatic linker.
- the ortho-dihydroxyphenyl moieties can be attached to the biodegradable polymer as grafts or as pendant groups.
- poly(depsipeptide) wherein the amino acid is aspartic acid, glutamic acid or lysine are possible according to the invention.
- poly(depsipeptide) refers to a polypeptide in which one or more of the amide bonds are replaced by ester bonds.
- An exemplary poly(depsipeptide) is depicted by formula V below:
- R 2 and R3 can independently be either hydrogen or a methyl group.
- This structure allows for any number of ortho-dihydroxyphenyl groups up to that matching the monomer number "m".
- two cyclic monomers are used to produce the polymer.
- One monomer bears the protected amino acid side chain that is used to conjugate the dopamine or other ortho- dihydroxyphenyl group.
- the second cyclic monomer is a conventional ring opening monomer such as glycolide, lactide, dioxanone, ⁇ -butyro lactone, ⁇ -propiolactone or caprolactone.
- a schematic showing presently preferred amino acids and hydroxyl acids in the first block and the possible ring opening monomers in the second block is depicted below:
- hydroxy acid 1, hydroxy acid 2 and hydroxy acid 3 can be independently selected from a group that includes glycolic acid, L-lactic acid, D-lactic acid, caprolactone, dioxanone, ⁇ -butyrolactone, ⁇ -propiolactone and ⁇ -valerolactone.
- These amino acids include those with R-groups that could be used for attachment of an ortho-dihydroxyphenyl group. Aspartic acid, glutamic acid and lysine are presently preferred.
- An ortho-dihydroxyphenyl group of the invention can also be added to other biodegradable polymers including poly(esteramides), poly(tyrosine-derived carbonates), poly(tyrosine-derived esters), poly(tyrosine-alphahydroxyacids) and biodegradable polyurethanes.
- R] can be any Ci to Cu linear, branched, cycloaliphatic, aromatic or unsaturated hydrocarbon. Methods of synthesizing the precursor to the compound of formula VI are known in the art.
- R 1 may be any Ci to Ci 6 linear, branched, cycloaliphatic, aromatic, unsaturated hydrocarbon, poly(ethylene glycol), poly(propylene glycol), or poly(tetramethylene gycol). Methods of synthesizing this type of poly(tyrosine- derived ester) are known to those skilled in the art.
- biodegradable coatings of the invention are primarily intended to be used as primer layers on an implantable medical device, they also may serve as drug reservoir layers.
- implantable medical device refers to any type of appliance that is totally or partly introduced, surgically or medically, into a patient's body or by medical intervention into a natural orifice, and which is intended to remain there after the procedure.
- the duration of implantation may be essentially permanent, i.e., intended to remain in place for the remaining lifespan of the patient; until the device biodegrades; or until it is physically removed.
- implantable medical devices include, without limitation, implantable cardiac pacemakers and defibrillators, leads and electrodes for the preceding, implantable organ stimulators such as nerve, bladder, sphincter and diaphragm stimulators, cochlear implants, prostheses, vascular grafts, self-expandable stents, balloon-expandable stents, stent-grafts, AV fistulas, grafts, PFO closure devices, arterial closure devices, artificial heart valves and cerebrospinal fluid shunts.
- implantable organ stimulators such as nerve, bladder, sphincter and diaphragm stimulators
- cochlear implants prostheses, vascular grafts, self-expandable stents, balloon-expandable stents, stent-grafts, AV fistulas, grafts, PFO closure devices, arterial closure devices, artificial heart valves and cerebrospinal fluid shunts.
- preferred implantable medical devices for use with coatings of this invention are stents.
- a stent refers generally to any device used to hold tissue in place in a patient's body.
- Particularly useful stents are those used for the maintenance of the patency of a vessel in a patient's body when the vessel is narrowed or closed due to diseases or disorders including, without limitation, tumors (in, for example, bile ducts, the esophagus or the trachea/bronchi), benign pancreatic disease, coronary artery disease, carotid artery disease, renal artery disease and peripheral arterial disease such as atherosclerosis, restenosis and vulnerable plaque.
- a stent can be used to strengthen the wall of the vessel in the vicinity of a vulnerable plaque (VP).
- VP vulnerable plaque
- VP refers to a fatty build-up in an artery thought to be caused by inflammation.
- the VP is covered by a thin fibrous cap that can rupture leading to blood clot formation.
- a stent can not only maintain vessel patency but can act as a shield against VP rupture.
- a stent can be used in, without limitation, neuro, carotid, coronary, pulmonary, aortic, renal, biliary, iliac, femoral and popliteal as well as other peripheral vasculatures.
- a stent can be used in the treatment or prevention of disorders such as, without limitation, thrombosis, restenosis, hemorrhage, vascular dissection or perforation, vascular aneurysm, chronic total occlusion, claudication, anastomotic proliferation, bile duct obstruction and ureter obstruction.
- stents may also be employed for the localized delivery of therapeutic agents to specific treatment sites in a patient's body. Indeed, therapeutic agent delivery may be the sole purpose of the stent or the stent may be primarily intended for another use such as those discussed above with drug delivery providing an ancillary benefit.
- a stent used for patency maintenance is usually delivered to the target site in a compressed state and then expanded to fit the vessel into which it has been inserted. Once at a target location, a stent may be self-expandable or balloon expandable. A stent coating must be flexible and capable of elongation.
- stent materials include stainless steel, nitinol, tantalum, tantalum alloy, titanium, titanium alloy, cobalt chromium alloys, cobalt nickel alloys, platinum modified stainless steel, nickel-titanium-platinum alloys, niobium, niobium alloy, zirconium and zirconium alloy.
- an implantable medical device of the invention will have coated on it's surface at least one layer of a biologically compatible coating of the invention, although any number of coating layers are encompassed by the invention.
Abstract
Biodegradable coatings for implantable medical devices are disclosed.
Description
BIODEGRADABLE COATINGS FOR IMPLANTABLE MEDICAL DEVICES
FIELD OF THE INVENTION
The present invention is directed to biodegradable coatings for implantable medical devices.
BACKGROUND OF THE INVENTION
The traditional method of administering therapeutic agents to treat diseases of the internal organs and vasculature has been by systemic delivery. Systemic delivery involves administering a therapeutic agent at a discrete location followed by the agent migrating throughout the patient's body including, of course, to the afflicted organ or area of the vasculature. But to achieve a therapeutic amount of the agent at the afflicted site, an initial dose substantially greater than the therapeutic amount must be administered to account for the dilution the agent undergoes as it travels through the body. Systemic delivery introduces the therapeutic agent in two ways: into the digestive tract (enteral administration) or into the vascular system (parenteral administration), either directly, such as injection into a vein or an artery, or indirectly, such as injection into a muscle or into the bone marrow. Absorption, distribution, metabolism, excretion and toxicity, the ADMET factors, strongly influence delivery by each of these routes. For enteric administration, factors such as a compound's solubility, its stability in the acidic environs of the stomach and its ability to permeate the intestinal wall all affect drug absorption and therefore its bioavailability. For parenteral delivery, factors such as enzymatic degradation,
lipophilic/hydrophilic partitioning coefficient, lifetime in circulation, protein binding, etc. will affect the agent's bioavailability.
At the other end of the spectrum is local delivery, which comprises administering the therapeutic agent directly to the afflicted site. With localized delivery, the ADMET factors tend to be less important than with systemic administration because administration is essentially directly to the treatment site. Thus, the initial dose can be at or very close to the therapeutic amount. With time, some of the locally delivered therapeutic agent may diffuse over a wider region, but that is not the intent of localized delivery, and the diffused portion's concentration will ordinarily be sub-therapeutic, i.e., too low to have a therapeutic effect. Nevertheless, localized delivery of therapeutic agents is currently considered a state-of-the-art approach to the treatment of many diseases such as cancer and atherosclerosis.
Localized delivery of therapeutic agents may be accomplished using implantable medical devices. Coating implantable medical devices with therapeutic agents, however, is not without problems.
The family of mussel adhesive proteins is unique in that they bond to a large variety of substrates in an aqueous environment. These proteins share numerous molecular motifs, however, approximately 25% of amino acids in a particular mussel adhesive protein is the modified amino acid 3,4-dihydroxyphenyl-L-alanine (DOPA). It has further been determined that mussel adhesion to rocks, wood and metal is due in large part to DOPA. It has been found, however, that the portion of DOPA responsible for the remarkable adhesive capability of these polymers is the 3,4-dihydroxyphenyl group. The present invention takes advantage of the strong binding properties of 3,4-dihydroxyphenyl, and 2,3- dihydroxyphenyl, to provide novel biodegradable coatings, primarily for use as
primer coatings for implantable medical devices, particularly bare metal implantable medical devices.
SUMMARY
The present invention relates to a biodegradable coating for an implantable medical device that includes a biodegradable polymer functionalized with an ortho- dihydroxyphenyl compound, the overall structure having the formula:
In various aspects, R includes a polyester which can be selected from a group that includes a poly(glycolide), poly(D,L-lactide), poly(L-lactide), poly(D,L-lactide-co- glycolide), poly(caprolactone), poly(dioxanone), poly(glycolide-co-trimethylenecarbonate) and copolymers thereof.
In various aspects, R includes a poly(esteramide), poly(tyrosine-derived carbonate), a poly(tyrosine-derived ester), a poly(tyrosine-α-hydroxyacid), a poly(orthoester) or a biodegradable polyurethane.
In various aspects, R includes a poly(depsipeptide) which in some aspects can have the general formula:
X — |— Amino Acid Hydroxy Acid 1 — Vj — Hydroxy Acid 2 Hydroxy Acid 3
^ 'r? 'm where X is the linker group. In this aspect, the amino acid can be selected from the group consisting of aspartic acid, glutamic acid, lysine, cysteine, serine, threonine and tyrosine.
In this aspect, hydroxy acid 1, hydroxy acid 2 and hydroxy acid 3 can be independently selected from a group that includes glycolic acid, L-lactic acid, D-lactic acid, D,L-lactic
acid, meso-lactic acid, caprolactone, dioxanone, β-butyrolactone, β-propiolactone and β- valerolactone.
In various aspects, the linker group can include between 1 and 16 carbon atoms.
In various aspects, the linker group is linear, branched, unsaturated or cycloaliphatic. In various aspects, the linker group comprises an ester, an amide, an ether, an anhydride, a sulfoester, a thioether, a sulfone, a phosphonate, a phosphoester, a carbonate, an imino-carbonate, an acetal, a ketal, an imine, an ortho-ester, a sulfamide or a urethane bond.
In various aspects, the biodegradable polymer can be functionalized with two ortho-dihydroxyphenyl compounds, the overall structure having the formula:
Biodegradable Polymer
where X independently comprises a linear, branched, unsaturated or cycloaliphatic linker.
In various aspects, the biodegradable polymer can be functionalized with multiple ortho-dihydroxyphenyl compounds, the overall structure having the formula: r-
where X independently comprises a linear, branched, unsaturated or cycloaliphatic linker.
Another aspect of the invention relates to an implantable medical device that includes a coating according to the invention. The implantable medical device can be a stent.
DETAILED DESCRIPTION
The present invention provides a biodegradable coating for an implantable medical device that includes a biodegradable polymer functionalized with an ortho- dihydroxyphenyl compound, the overall structure having formula I:
I where X is a linker group and R is the biodegradable polymer.
In various aspects, a biodegradable polymer can be functionalized with a different ortho-dihydroxyphenyl compound, the overall structure having formula II:
II where X is a linker group and R is the biodegradable polymer.
It is to be understood that both of the ortho-dihydroxyphenyl compounds depicted by formulas I and II above are suitable for coatings of the present invention although compounds with the structure according to formula I are presently preferred.
As used herein, "biodegradable" refers to materials that are capable of being degraded or absorbed when exposed to bodily fluids such as blood, and components thereof such as enzymes or oxidative species, and that can be gradually absorbed and/or eliminated by the body. In various aspects, R includes a polyester which can be selected from a group that includes a poly(glycolide), poly(D,L-lactide), poly(L-lactide), poly(D,L-lactide-co- glycolide), poly(caprolactone), poly(dioxanone), poly(glycolide-co-trimethylenecarbonate) and copolymers thereof.
When the biodegradable coating is used as a primer layer on an implantable medical device and a drug reservoir layer is disposed over the primer layer, the R group can be chosen to be compatible with the reservoir layer polymer. For example, if a drug reservoir layer includes poly(D,L-lactide), then a primer layer would be chosen, without limitation, to also include poly(D,L-lactide), an example of which is shown by formula III.
III
The synthesis of this polymer involves ring-opening polymerization using D,L- lactide and glycolic acid as the initiator. This yields an acid functional poly(D,L-lactide). Dopamine is then coupled to the carboxyl endgroup, methods of which are known to those skilled in the art.
The polymer of formula III can attach to a metal surface, e.g., a bare metal stent, by ortho-dihydroxyphenyl endpoint attachment. If the polyester polymer segment is too
large however, it is unlikely that the ortho-dihydroxyphenyl would effectively coordinate with the metal surface. Thus, the polymer will be chosen to be less than 20,000 Daltons.
In an alternative embodiment, an ortho-dihydrophenyl moiety can be present at both termini of a biodegradable polymer, as shown by formula IV:
IV
Synthesis of this moiety can be accomplished using methods known to those skilled in the art, such as that depicted below:
In this pathway, Ri may be a C2 to Ciβ linear, branched, unsaturated or cyclic hydrocarbon. When this structure is used as a primer coating for a metal implantable device, the two ortho-dihydroxyphenyl moieties will attach to the device surface, thereby forming a loop-like structure on the device.
Biodegradable primers containing a much higher number of ortho-dihydroxy phenyl groups are also encompassed by the present invention. For example, the biodegradable polymer can be functionalized with multiple ortho-dihydroxyphenyl compounds having an overall structure with the formula: r-
In this aspect, the ortho-dihydroxyphenyl moieties can be attached to the biodegradable polymer as grafts or as pendant groups.
Similarly, a poly(depsipeptide) wherein the amino acid is aspartic acid, glutamic acid or lysine are possible according to the invention. As used herein, "poly(depsipeptide)" refers to a polypeptide in which one or more of the amide bonds are replaced by ester bonds. An exemplary poly(depsipeptide) is depicted by formula V below:
V
In this aspect of the invention, R2 and R3 can independently be either hydrogen or a methyl group. This structure allows for any number of ortho-dihydroxyphenyl groups up to that matching the monomer number "m". In this family of poly(depsipeptides), two cyclic monomers are used to produce the polymer. One monomer bears the protected amino acid side chain that is used to conjugate the dopamine or other ortho- dihydroxyphenyl group. The second cyclic monomer is a conventional ring opening monomer such as glycolide, lactide, dioxanone, β-butyro lactone, β-propiolactone or caprolactone. A schematic showing presently preferred amino acids and hydroxyl acids in the first block and the possible ring opening monomers in the second block is depicted below:
In this aspect, hydroxy acid 1, hydroxy acid 2 and hydroxy acid 3 can be independently selected from a group that includes glycolic acid, L-lactic acid, D-lactic acid, caprolactone, dioxanone, β-butyrolactone, β-propiolactone and β-valerolactone. These amino acids include those with R-groups that could be used for attachment of an ortho-dihydroxyphenyl group. Aspartic acid, glutamic acid and lysine are presently preferred.
An ortho-dihydroxyphenyl group of the invention can also be added to other biodegradable polymers including poly(esteramides), poly(tyrosine-derived carbonates), poly(tyrosine-derived esters), poly(tyrosine-alphahydroxyacids) and biodegradable polyurethanes.
An example of a poly(tyrosine-derived carbonate) wherein the ortho- dihydroxyphenyl group is present as a conjugated dopamine and the amount of ortho- dihydroxyphenyl can be adjusted by varying the ratio of "m" to "n" is depicted by formula VI.
VI
R] can be any Ci to Cu linear, branched, cycloaliphatic, aromatic or unsaturated hydrocarbon. Methods of synthesizing the precursor to the compound of formula VI are known in the art.
An example of a poly(tyrosine-derived ester) is depicted by formula VII.
VII
As in formula VI above, the amount of ortho-dihydroxyphenyl substitution can be controlled by the amount of the first monomer. R1 may be any Ci to Ci6 linear, branched, cycloaliphatic, aromatic, unsaturated hydrocarbon, poly(ethylene glycol), poly(propylene glycol), or poly(tetramethylene gycol). Methods of synthesizing this type of poly(tyrosine- derived ester) are known to those skilled in the art.
It is to be understood that while the biodegradable coatings of the invention are primarily intended to be used as primer layers on an implantable medical device, they also may serve as drug reservoir layers.
Another aspect of the invention relates to an implantable medical device comprising a coating according to the invention.
As used herein, "implantable medical device" refers to any type of appliance that is totally or partly introduced, surgically or medically, into a patient's body or by medical intervention into a natural orifice, and which is intended to remain there after the procedure. The duration of implantation may be essentially permanent, i.e., intended to remain in place for the remaining lifespan of the patient; until the device biodegrades; or until it is physically removed. Examples of implantable medical devices include, without limitation, implantable cardiac pacemakers and defibrillators, leads and electrodes for the preceding, implantable organ stimulators such as nerve, bladder, sphincter and diaphragm stimulators, cochlear implants, prostheses, vascular grafts, self-expandable stents, balloon-expandable stents, stent-grafts, AV fistulas, grafts, PFO closure devices, arterial closure devices, artificial heart valves and cerebrospinal fluid shunts.
At present, preferred implantable medical devices for use with coatings of this invention are stents.
A stent refers generally to any device used to hold tissue in place in a patient's body. Particularly useful stents are those used for the maintenance of the patency of a vessel in a patient's body when the vessel is narrowed or closed due to diseases or disorders including, without limitation, tumors (in, for example, bile ducts, the esophagus or the trachea/bronchi), benign pancreatic disease, coronary artery disease, carotid artery disease, renal artery disease and peripheral arterial disease such as atherosclerosis, restenosis and vulnerable plaque. For example, a stent can be used to strengthen the wall of the vessel in the vicinity of a vulnerable plaque (VP). VP refers to a fatty build-up in an artery thought to be caused by inflammation. The VP is covered by a thin fibrous cap that can rupture leading to blood clot formation. Thus, a stent can not only maintain vessel patency but can act as a shield against VP rupture. A stent can be used in, without limitation, neuro, carotid, coronary, pulmonary, aortic, renal, biliary, iliac, femoral and
popliteal as well as other peripheral vasculatures. A stent can be used in the treatment or prevention of disorders such as, without limitation, thrombosis, restenosis, hemorrhage, vascular dissection or perforation, vascular aneurysm, chronic total occlusion, claudication, anastomotic proliferation, bile duct obstruction and ureter obstruction. In addition to the above uses, stents may also be employed for the localized delivery of therapeutic agents to specific treatment sites in a patient's body. Indeed, therapeutic agent delivery may be the sole purpose of the stent or the stent may be primarily intended for another use such as those discussed above with drug delivery providing an ancillary benefit. A stent used for patency maintenance is usually delivered to the target site in a compressed state and then expanded to fit the vessel into which it has been inserted. Once at a target location, a stent may be self-expandable or balloon expandable. A stent coating must be flexible and capable of elongation.
Examples of stent materials include stainless steel, nitinol, tantalum, tantalum alloy, titanium, titanium alloy, cobalt chromium alloys, cobalt nickel alloys, platinum modified stainless steel, nickel-titanium-platinum alloys, niobium, niobium alloy, zirconium and zirconium alloy.
It is to be understood that an implantable medical device of the invention will have coated on it's surface at least one layer of a biologically compatible coating of the invention, although any number of coating layers are encompassed by the invention.
While particular embodiments of the present invention have been shown and described, it will be obvious to those skilled in the art that changes and modifications can be made without departing from this invention in its broader aspects. Therefore, the appended claims are to encompass within their scope all such changes and modifications as fall within the true spirit and scope of this invention.
Claims
1. A biodegradable coating for an implantable medical device comprising: a biodegradable polymer functionalized with an ortho-dihydroxyphenyl compound having the formula:
2. The coating according to claim 1, wherein R comprises a polyester.
3. The coating according to claim 2, wherein the polyester is selected from the group consisting of poly(glycolide), poly(D,L-lactide), poly(L-lactide), poly(D,L-lactide- co-glycolide), poly(caprolactone), poly(dioxanone), poly(glycolide-co- trimethylenecarbonate) and copolymers thereof.
4. The coating according to claim 1, wherein R comprises a poly(esteramide), poly(tyrosine-derived carbonate), a poly(tyrosine-derived ester), a poly(tyrosine- alphahydroxyacid), poly(orthoester) or a biodegradable polyurethane.
5. The coating according to claim 1, wherein R comprises a poly(depsipeptide).
6. The coating according to claim 5, wherein the poly(depsipeptide) has the general formula:
7. The coating according to claim 6, wherein the amino acid is selected from the group consisting of aspartic acid, glutamic acid, lysine, cysteine, serine, threonine and tyrosine.
8. The coating according to claim 6, wherein hydroxy acid 1, hydroxy acid 2 and hydroxy acid 3 are independently selected from the group consisting of glycolic acid, L- lactic acid, D-lactic acid, D,L-lactic acid, meso-lactic acid, caprolactone, dioxanone, β- butyrolactone, β-propiolactone and β-valerolactone.
9. The coating according to claim 1, wherein the linker group comprises between 1 and 16 carbon atoms.
10. The coating according to claim 9, wherein the linker group is linear, branched, unsaturated or cycloaliphatic.
11. The coating according to claim 10, wherein the linker group comprises an ester, an amide, an ether, an anhydride, a sulfoester, a thioether, a sulfone, a phosphonate, a phosphoester, a carbonate an imino-carbonate, an acetal, a ketal, an imine, an ortho-ester, a sulfamide or a urethane bond.
12. The biodegradable coating according to claim 1 comprising: the biodegradable polymer functionalized with two ortho-dihydroxyphenyl compounds having the formula:
13. The biodegradable coating according to claim 1 comprising: the biodegradable polymer functionalized with multiple ortho-dihydroxyphenyl compounds having the formula: r-
14. An implantable medical device comprising the coating according to claim 1.
15. The implantable medical device of claim 14, wherein the implantable medical device comprises a stent.
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US12/023,953 US8791171B2 (en) | 2003-05-01 | 2008-01-31 | Biodegradable coatings for implantable medical devices |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2784101A1 (en) * | 2013-03-28 | 2014-10-01 | Nitto Europe N.V | Hydroxyphenyl functionalized poly(ester amide) |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8846069B2 (en) * | 2003-11-20 | 2014-09-30 | Abbott Cardiovascular Systems Inc. | Coatings for implantable devices comprising polymers of lactic acid and methods for fabricating the same |
US9023114B2 (en) | 2006-11-06 | 2015-05-05 | Tyrx, Inc. | Resorbable pouches for implantable medical devices |
AU2009295960A1 (en) | 2008-09-29 | 2010-04-01 | Cardiaq Valve Technologies, Inc. | Heart valve |
EP2341871B1 (en) | 2008-10-01 | 2017-03-22 | Edwards Lifesciences CardiAQ LLC | Delivery system for vascular implant |
AU2010236288A1 (en) | 2009-04-15 | 2011-10-20 | Cardiaq Valve Technologies, Inc. | Vascular implant and delivery system |
US8579964B2 (en) | 2010-05-05 | 2013-11-12 | Neovasc Inc. | Transcatheter mitral valve prosthesis |
JP6031033B2 (en) * | 2010-08-25 | 2016-11-24 | タイレックス・インコーポレイテッドTyrx Inc. | New coatings for medical devices |
AU2011326417A1 (en) | 2010-11-12 | 2013-05-09 | Tyrx, Inc. | Anchorage devices comprising an active pharmaceutical ingredient |
US9554897B2 (en) | 2011-04-28 | 2017-01-31 | Neovasc Tiara Inc. | Methods and apparatus for engaging a valve prosthesis with tissue |
US9308087B2 (en) | 2011-04-28 | 2016-04-12 | Neovasc Tiara Inc. | Sequentially deployed transcatheter mitral valve prosthesis |
US9345573B2 (en) | 2012-05-30 | 2016-05-24 | Neovasc Tiara Inc. | Methods and apparatus for loading a prosthesis onto a delivery system |
US10583002B2 (en) | 2013-03-11 | 2020-03-10 | Neovasc Tiara Inc. | Prosthetic valve with anti-pivoting mechanism |
US9681951B2 (en) | 2013-03-14 | 2017-06-20 | Edwards Lifesciences Cardiaq Llc | Prosthesis with outer skirt and anchors |
US9572665B2 (en) | 2013-04-04 | 2017-02-21 | Neovasc Tiara Inc. | Methods and apparatus for delivering a prosthetic valve to a beating heart |
US9667806B2 (en) | 2013-10-18 | 2017-05-30 | Aeris Communications, Inc. | Pair-the-plan system for devices and method of use |
US11115542B2 (en) | 2013-10-18 | 2021-09-07 | Aeris Communications, Inc. | Pair-the-plan system for devices and method of use |
US20150297706A1 (en) | 2014-04-18 | 2015-10-22 | Auburn University | Particulate Vaccine Formulations for Inducing Innate and Adaptive Immunity |
US10293044B2 (en) | 2014-04-18 | 2019-05-21 | Auburn University | Particulate formulations for improving feed conversion rate in a subject |
US10583199B2 (en) | 2016-04-26 | 2020-03-10 | Northwestern University | Nanocarriers having surface conjugated peptides and uses thereof for sustained local release of drugs |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050288398A1 (en) * | 2001-07-20 | 2005-12-29 | Messersmith Phillip B | Polymeric compositions and related methods of use |
WO2008019352A1 (en) * | 2006-08-04 | 2008-02-14 | Nerites Corporation | Biomimetic compounds and synthetic methods therefor |
Family Cites Families (213)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1078329B (en) | 1955-04-27 | 1960-03-24 | Du Pont | Process for the production of an elastic copolymer from vinylidene fluoride and another fluoroolefin |
US2968649A (en) * | 1958-12-04 | 1961-01-17 | Du Pont | Elastomeric terpolymers |
US3178399A (en) * | 1961-08-10 | 1965-04-13 | Minnesota Mining & Mfg | Fluorine-containing polymers and preparation thereof |
US3324069A (en) * | 1964-10-23 | 1967-06-06 | Pennsalt Chemicals Corp | Vinylidene fluoride polymer dispersions |
US3856827A (en) | 1970-12-28 | 1974-12-24 | Jefferson Chem Co Inc | Silicon containing molybdenum catalysts |
US3779805A (en) | 1971-05-19 | 1973-12-18 | Bell Telephone Labor Inc | Method of making waveguide mode filter |
US4076929A (en) * | 1975-10-30 | 1978-02-28 | Pennwalt Corporation | Vinylidene fluoride polymer having improved melt flow properties |
US4197380A (en) * | 1978-03-01 | 1980-04-08 | Raychem Corporation | Hot melt adhesive comprising fluorocarbon elastomer, ethylene copolymer and tackifier |
US4346710A (en) | 1978-06-16 | 1982-08-31 | Pennwalt Corporation | Article for storage and transport of biogenic fluids |
US4353960A (en) | 1978-09-21 | 1982-10-12 | Kureha Kagaku Kogyo Kabushiki Kaisha | Composite and conjugate filaments |
JPS6037733B2 (en) | 1978-10-12 | 1985-08-28 | 住友電気工業株式会社 | Tubular organ prosthesis material and its manufacturing method |
US4423183A (en) | 1980-09-16 | 1983-12-27 | David Hudson, Inc. | Fluoroelastomer film compositions and solutions containing fatty polyamide curatives |
JPS57144756A (en) | 1981-03-04 | 1982-09-07 | Koken Kk | Impermeable laminated film |
US4975505A (en) | 1981-08-20 | 1990-12-04 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4935477A (en) * | 1981-08-20 | 1990-06-19 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4977026A (en) | 1981-08-20 | 1990-12-11 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4999248A (en) * | 1981-08-20 | 1991-03-12 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4973142A (en) | 1981-08-20 | 1990-11-27 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4985308A (en) * | 1981-08-20 | 1991-01-15 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4977008A (en) | 1981-08-20 | 1990-12-11 | E. I Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4754009A (en) * | 1981-08-20 | 1988-06-28 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US5006382A (en) * | 1981-08-20 | 1991-04-09 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4982056A (en) * | 1981-08-20 | 1991-01-01 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxide |
US4977297A (en) | 1981-08-20 | 1990-12-11 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4977025A (en) | 1981-08-20 | 1990-12-11 | E. I Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4530569A (en) * | 1981-08-20 | 1985-07-23 | E. I. Du Pont De Nemours And Company | Optical fibers comprising cores clad with amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US5000547A (en) * | 1981-08-20 | 1991-03-19 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4948851A (en) | 1981-08-20 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of perfluoro-2,2-dimethyl-1,3-dioxole |
US4485250A (en) | 1981-11-19 | 1984-11-27 | E. I. Du Pont De Nemours And Company | Perfluorodioxole and its polymers |
US4399264A (en) | 1981-11-19 | 1983-08-16 | E. I. Du Pont De Nemours & Co. | Perfluorodioxole and its polymers |
US5051978A (en) | 1982-11-30 | 1991-09-24 | Burroughs Corporation | Coated media for optical recording |
US4636346A (en) * | 1984-03-08 | 1987-01-13 | Cordis Corporation | Preparing guiding catheter |
US4564013A (en) * | 1984-05-24 | 1986-01-14 | Ethicon, Inc. | Surgical filaments from vinylidene fluoride copolymers |
US4569978A (en) * | 1984-07-25 | 1986-02-11 | Pennwalt Corporation | Emulsion polymerization of vinylidene fluoride polymers in the presence of trichlorofluoromethane as chain transfer agent |
US4718907A (en) * | 1985-06-20 | 1988-01-12 | Atrium Medical Corporation | Vascular prosthesis having fluorinated coating with varying F/C ratio |
US4632842A (en) | 1985-06-20 | 1986-12-30 | Atrium Medical Corporation | Glow discharge process for producing implantable devices |
US4733665C2 (en) * | 1985-11-07 | 2002-01-29 | Expandable Grafts Partnership | Expandable intraluminal graft and method and apparatus for implanting an expandable intraluminal graft |
US4871357A (en) | 1986-01-21 | 1989-10-03 | Baxter International Inc. | Ionic heparin coating |
US4749585A (en) * | 1986-04-11 | 1988-06-07 | University Of Medicine And Dentistry Of New Jersey | Antibiotic bonded prosthesis and process for producing same |
GB2194539B (en) | 1986-09-01 | 1990-08-01 | Labofina Sa | Pvdf-based powder coatings |
JPS6389138A (en) * | 1986-10-03 | 1988-04-20 | オリンパス光学工業株式会社 | Cover of curved pipe for endoscope |
US4800882A (en) * | 1987-03-13 | 1989-01-31 | Cook Incorporated | Endovascular stent and delivery system |
US4876109A (en) | 1987-04-13 | 1989-10-24 | Cardiac Pacemakers, Inc. | Soluble covering for cardiac pacing electrode |
US4897457A (en) * | 1987-08-14 | 1990-01-30 | Asahi Glass Company Ltd. | Novel fluorine-containing cyclic polymer |
US5047020A (en) | 1987-09-14 | 1991-09-10 | Baxter International Inc. | Ionic heparin coating |
US4886062A (en) | 1987-10-19 | 1989-12-12 | Medtronic, Inc. | Intravascular radially expandable stent and method of implant |
US5185408A (en) | 1987-12-17 | 1993-02-09 | Allied-Signal Inc. | Medical devices fabricated totally or in part from copolymers of recurring units derived from cyclic carbonates and lactides |
US5076659A (en) | 1988-05-27 | 1991-12-31 | E. I. Du Pont De Nemours And Company | Process for the stabilization of fluoropolymers |
US4931287A (en) * | 1988-06-14 | 1990-06-05 | University Of Utah | Heterogeneous interpenetrating polymer networks for the controlled release of drugs |
US5444113A (en) * | 1988-08-08 | 1995-08-22 | Ecopol, Llc | End use applications of biodegradable polymers |
US4908404A (en) * | 1988-08-22 | 1990-03-13 | Biopolymers, Inc. | Synthetic amino acid-and/or peptide-containing graft copolymers |
US5328471A (en) | 1990-02-26 | 1994-07-12 | Endoluminal Therapeutics, Inc. | Method and apparatus for treatment of focal disease in hollow tubular organs and other tissue lumens |
US5053048A (en) | 1988-09-22 | 1991-10-01 | Cordis Corporation | Thromboresistant coating |
US5030394A (en) * | 1988-11-08 | 1991-07-09 | Labofina, S.A. | PVdF-based powder coatings |
US4977901A (en) | 1988-11-23 | 1990-12-18 | Minnesota Mining And Manufacturing Company | Article having non-crosslinked crystallized polymer coatings |
AU5830090A (en) | 1989-06-15 | 1991-01-08 | Du Pont Canada Inc. | Perfluorodioxole membranes |
US5196404B1 (en) | 1989-08-18 | 1996-09-10 | Biogen Inc | Inhibitors of thrombin |
US5971954A (en) | 1990-01-10 | 1999-10-26 | Rochester Medical Corporation | Method of making catheter |
US5545208A (en) | 1990-02-28 | 1996-08-13 | Medtronic, Inc. | Intralumenal drug eluting prosthesis |
US5107852A (en) * | 1990-04-02 | 1992-04-28 | W. L. Gore & Associates, Inc. | Catheter guidewire device having a covering of fluoropolymer tape |
US5093427A (en) * | 1990-05-10 | 1992-03-03 | Atochem North America, Inc. | Copolymers of vinylidene fluoride and hexafluoropropylene and process for preparing the same |
US5395311A (en) | 1990-05-14 | 1995-03-07 | Andrews; Winston A. | Atherectomy catheter |
AU7998091A (en) | 1990-05-17 | 1991-12-10 | Harbor Medical Devices, Inc. | Medical device polymer |
US6060451A (en) * | 1990-06-15 | 2000-05-09 | The National Research Council Of Canada | Thrombin inhibitors based on the amino acid sequence of hirudin |
US5112457A (en) | 1990-07-23 | 1992-05-12 | Case Western Reserve University | Process for producing hydroxylated plasma-polymerized films and the use of the films for enhancing the compatiblity of biomedical implants |
US5455040A (en) | 1990-07-26 | 1995-10-03 | Case Western Reserve University | Anticoagulant plasma polymer-modified substrate |
US5302385A (en) | 1990-08-20 | 1994-04-12 | Becton, Dickinson And Company | Polyurethane-polyvinylpyrrolidone block copolymer and iodine carrier therefrom |
US5632776A (en) * | 1990-11-22 | 1997-05-27 | Toray Industries, Inc. | Implantation materials |
US5246451A (en) | 1991-04-30 | 1993-09-21 | Medtronic, Inc. | Vascular prosthesis and method |
JP3558293B2 (en) * | 1991-08-27 | 2004-08-25 | ダイキン工業株式会社 | Fluoro rubber coating composition |
US5176972A (en) | 1991-09-11 | 1993-01-05 | Polaroid Corporation | Imaging medium with low refractive index layer |
WO1993005825A1 (en) | 1991-09-20 | 1993-04-01 | Baxter International Inc. | Processes for reducing the thrombogenicity of biomaterials |
AU2605592A (en) | 1991-10-15 | 1993-04-22 | Atrix Laboratories, Inc. | Polymeric compositions useful as controlled release implants |
JPH05307137A (en) * | 1992-01-07 | 1993-11-19 | Olympus Optical Co Ltd | Lens barrel |
US5296283A (en) | 1992-01-13 | 1994-03-22 | E. I. Du Pont De Nemours And Company | Protective coating for machine-readable markings |
US5573934A (en) * | 1992-04-20 | 1996-11-12 | Board Of Regents, The University Of Texas System | Gels for encapsulation of biological materials |
US5591224A (en) * | 1992-03-19 | 1997-01-07 | Medtronic, Inc. | Bioelastomeric stent |
US5599352A (en) | 1992-03-19 | 1997-02-04 | Medtronic, Inc. | Method of making a drug eluting stent |
SE500972C2 (en) * | 1992-03-30 | 1994-10-10 | Moelnlycke Ab | Method and apparatus for manufacturing wound dressings and a wound dressing made by the method |
CA2094858C (en) | 1992-04-28 | 2004-06-15 | Robert D. Mitchell | Method of treating hyperproliferative vascular disease |
US5368566A (en) | 1992-04-29 | 1994-11-29 | Cardiovascular Dynamics, Inc. | Delivery and temporary stent catheter having a reinforced perfusion lumen |
US5276121A (en) | 1992-05-05 | 1994-01-04 | E. I. Du Pont De Nemours And Company | Amorphous copolymers of two fluorinated ring monomers |
US5383928A (en) | 1992-06-10 | 1995-01-24 | Emory University | Stent sheath for local drug delivery |
US5383853A (en) | 1992-11-12 | 1995-01-24 | Medtronic, Inc. | Rapid exchange catheter |
US5342348A (en) | 1992-12-04 | 1994-08-30 | Kaplan Aaron V | Method and device for treating and enlarging body lumens |
US5336518A (en) | 1992-12-11 | 1994-08-09 | Cordis Corporation | Treatment of metallic surfaces using radiofrequency plasma deposition and chemical attachment of bioactive agents |
US5443458A (en) | 1992-12-22 | 1995-08-22 | Advanced Cardiovascular Systems, Inc. | Multilayered biodegradable stent and method of manufacture |
US5824048A (en) | 1993-04-26 | 1998-10-20 | Medtronic, Inc. | Method for delivering a therapeutic substance to a body lumen |
US5464650A (en) * | 1993-04-26 | 1995-11-07 | Medtronic, Inc. | Intravascular stent and method |
JPH07498A (en) | 1993-06-02 | 1995-01-06 | Uchida Yasunari | Bone inducing material |
US5861168A (en) * | 1993-06-11 | 1999-01-19 | The Board Of Trustees Of The Leland Stanford Junior University | Intramural delivery of nitric oxide enhancer for inhibiting lesion formation after vascular injury |
JPH0767895A (en) | 1993-06-25 | 1995-03-14 | Sumitomo Electric Ind Ltd | Antimicrobial artificial blood vessel and suture yarn for antimicrobial operation |
US5716981A (en) * | 1993-07-19 | 1998-02-10 | Angiogenesis Technologies, Inc. | Anti-angiogenic compositions and methods of use |
EG20321A (en) | 1993-07-21 | 1998-10-31 | Otsuka Pharma Co Ltd | Medical material and process for producing the same |
WO1995003010A1 (en) * | 1993-07-23 | 1995-02-02 | Cook Incorporated | A flexible stent having a pattern formed from a sheet of material |
AU7476894A (en) * | 1993-07-29 | 1995-02-28 | Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services, The | Method of treating atherosclerosis or restenosis using microtubule stabilizing agent |
US5380299A (en) | 1993-08-30 | 1995-01-10 | Med Institute, Inc. | Thrombolytic treated intravascular medical device |
US5310838A (en) | 1993-09-07 | 1994-05-10 | E. I. Du Pont De Nemours And Company | Functional fluoropolymers |
US5723004A (en) | 1993-10-21 | 1998-03-03 | Corvita Corporation | Expandable supportive endoluminal grafts |
DE4337613A1 (en) | 1993-11-04 | 1995-05-11 | Fichtel & Sachs Ag | Friction clutch with automatic wear compensation and play generator |
DE69428721T2 (en) * | 1993-12-10 | 2002-06-20 | Schneider Usa Inc | guide catheter |
WO1995019796A1 (en) * | 1994-01-21 | 1995-07-27 | Brown University Research Foundation | Biocompatible implants |
US5403341A (en) | 1994-01-24 | 1995-04-04 | Solar; Ronald J. | Parallel flow endovascular stent and deployment apparatus therefore |
AU710504B2 (en) | 1994-03-15 | 1999-09-23 | Brown University Research Foundation | Polymeric gene delivery system |
DE69532049T2 (en) | 1994-04-01 | 2004-07-08 | Prograft Medical, Inc., Palo Alto | Self-expanding stent or stent graft and method for its preparation |
US5408020A (en) | 1994-05-09 | 1995-04-18 | E. I. Du Pont De Nemours And Company | Copolymers of perhalo-2,2-di-loweralkyl-1,3-dioxole, and perfluoro-2-methylene-4-methyl-1,3-dioxolane |
US5629077A (en) * | 1994-06-27 | 1997-05-13 | Advanced Cardiovascular Systems, Inc. | Biodegradable mesh and film stent |
US5670558A (en) | 1994-07-07 | 1997-09-23 | Terumo Kabushiki Kaisha | Medical instruments that exhibit surface lubricity when wetted |
US5656121A (en) | 1994-08-19 | 1997-08-12 | Minnesota Mining And Manufacturing Company | Method of making multi-layer composites having a fluoropolymer layer |
US5578073A (en) | 1994-09-16 | 1996-11-26 | Ramot Of Tel Aviv University | Thromboresistant surface treatment for biomaterials |
US5649977A (en) * | 1994-09-22 | 1997-07-22 | Advanced Cardiovascular Systems, Inc. | Metal reinforced polymer stent |
TW363075B (en) | 1994-11-01 | 1999-07-01 | Daikin Ind Ltd | Fluoride polymer compound painting and coating method thereof |
US5637113A (en) | 1994-12-13 | 1997-06-10 | Advanced Cardiovascular Systems, Inc. | Polymer film for wrapping a stent structure |
US5919570A (en) | 1995-02-01 | 1999-07-06 | Schneider Inc. | Slippery, tenaciously adhering hydrogel coatings containing a polyurethane-urea polymer hydrogel commingled with a poly(N-vinylpyrrolidone) polymer hydrogel, coated polymer and metal substrate materials, and coated medical devices |
US6017577A (en) * | 1995-02-01 | 2000-01-25 | Schneider (Usa) Inc. | Slippery, tenaciously adhering hydrophilic polyurethane hydrogel coatings, coated polymer substrate materials, and coated medical devices |
US5575818A (en) | 1995-02-14 | 1996-11-19 | Corvita Corporation | Endovascular stent with locking ring |
US6179817B1 (en) * | 1995-02-22 | 2001-01-30 | Boston Scientific Corporation | Hybrid coating for medical devices |
US5869127A (en) * | 1995-02-22 | 1999-02-09 | Boston Scientific Corporation | Method of providing a substrate with a bio-active/biocompatible coating |
US6147168A (en) * | 1995-03-06 | 2000-11-14 | Ethicon, Inc. | Copolymers of absorbable polyoxaesters |
US5605696A (en) * | 1995-03-30 | 1997-02-25 | Advanced Cardiovascular Systems, Inc. | Drug loaded polymeric material and method of manufacture |
ES2201173T3 (en) | 1995-04-07 | 2004-03-16 | BIO-TEC BIOLOGISCHE NATURVERPACKUNGEN GMBH & CO. KG | BIOLOGICALLY DEGRADABLE POLYMER MIX. |
US6120536A (en) | 1995-04-19 | 2000-09-19 | Schneider (Usa) Inc. | Medical devices with long term non-thrombogenic coatings |
US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
US5837313A (en) | 1995-04-19 | 1998-11-17 | Schneider (Usa) Inc | Drug release stent coating process |
US5900425A (en) * | 1995-05-02 | 1999-05-04 | Bayer Aktiengesellschaft | Pharmaceutical preparations having controlled release of active compound and processes for their preparation |
US5562734A (en) | 1995-05-31 | 1996-10-08 | Zimmer, Inc. | Method for reducing gamma radiation sterilization induced discoloration |
US5628728A (en) * | 1995-05-31 | 1997-05-13 | Ekos Corporation | Medicine applying tool |
US5704910A (en) * | 1995-06-05 | 1998-01-06 | Nephros Therapeutics, Inc. | Implantable device and use therefor |
US5820917A (en) | 1995-06-07 | 1998-10-13 | Medtronic, Inc. | Blood-contacting medical device and method |
US5609629A (en) | 1995-06-07 | 1997-03-11 | Med Institute, Inc. | Coated implantable medical device |
CA2178541C (en) | 1995-06-07 | 2009-11-24 | Neal E. Fearnot | Implantable medical device |
US5750234A (en) * | 1996-06-07 | 1998-05-12 | Avery Dennison Corporation | Interior automotive laminate with thermoplastic low gloss coating |
US6129761A (en) | 1995-06-07 | 2000-10-10 | Reprogenesis, Inc. | Injectable hydrogel compositions |
US5667767A (en) | 1995-07-27 | 1997-09-16 | Micro Therapeutics, Inc. | Compositions for use in embolizing blood vessels |
US5804318A (en) | 1995-10-26 | 1998-09-08 | Corvita Corporation | Lubricious hydrogel surface modification |
US6042605A (en) | 1995-12-14 | 2000-03-28 | Gore Enterprose Holdings, Inc. | Kink resistant stent-graft |
JP2000503559A (en) | 1995-12-14 | 2000-03-28 | ゴア エンタープライズ ホールディングス,インコーポレイティド | Apparatus and method for deploying a stent-graft |
JP3941128B2 (en) * | 1995-12-18 | 2007-07-04 | ダイキン工業株式会社 | Powder coating composition |
ATE330644T1 (en) * | 1995-12-18 | 2006-07-15 | Angiotech Biomaterials Corp | CROSS-LINKED POLYMER MATERIALS AND METHODS FOR USE THEREOF |
US5713949A (en) * | 1996-08-06 | 1998-02-03 | Jayaraman; Swaminathan | Microporous covered stents and method of coating |
US5932299A (en) | 1996-04-23 | 1999-08-03 | Katoot; Mohammad W. | Method for modifying the surface of an object |
GB9608882D0 (en) | 1996-04-30 | 1996-07-03 | Luthra Ajay K | Non-thrombogenic and anti-thrombogenic polymers |
US5874165A (en) * | 1996-06-03 | 1999-02-23 | Gore Enterprise Holdings, Inc. | Materials and method for the immobilization of bioactive species onto polymeric subtrates |
NL1003497C2 (en) | 1996-07-03 | 1998-01-07 | Cordis Europ | Catheter with temporary vena-cava filter. |
US5928279A (en) * | 1996-07-03 | 1999-07-27 | Baxter International Inc. | Stented, radially expandable, tubular PTFE grafts |
US6060534A (en) * | 1996-07-11 | 2000-05-09 | Scimed Life Systems, Inc. | Medical devices comprising ionically and non-ionically crosslinked polymer hydrogels having improved mechanical properties |
US5830178A (en) | 1996-10-11 | 1998-11-03 | Micro Therapeutics, Inc. | Methods for embolizing vascular sites with an emboilizing composition comprising dimethylsulfoxide |
US6033724A (en) * | 1996-11-27 | 2000-03-07 | Spalding Sports Worldwide, Inc. | Golf ball mold preparation technique and coating system |
US5980972A (en) | 1996-12-20 | 1999-11-09 | Schneider (Usa) Inc | Method of applying drug-release coatings |
US5997517A (en) | 1997-01-27 | 1999-12-07 | Sts Biopolymers, Inc. | Bonding layers for medical device surface coatings |
US5858990A (en) * | 1997-03-04 | 1999-01-12 | St. Elizabeth's Medical Center | Fas ligand compositions for treatment of proliferative disorders |
US6273913B1 (en) | 1997-04-18 | 2001-08-14 | Cordis Corporation | Modified stent useful for delivery of drugs along stent strut |
US6165166A (en) | 1997-04-25 | 2000-12-26 | Schneider (Usa) Inc. | Trilayer, extruded medical tubing and medical devices incorporating such tubing |
US5879697A (en) * | 1997-04-30 | 1999-03-09 | Schneider Usa Inc | Drug-releasing coatings for medical devices |
US6056993A (en) * | 1997-05-30 | 2000-05-02 | Schneider (Usa) Inc. | Porous protheses and methods for making the same wherein the protheses are formed by spraying water soluble and water insoluble fibers onto a rotating mandrel |
DE19723723C2 (en) | 1997-05-30 | 1999-05-20 | Fraunhofer Ges Forschung | Polymer coating for prostheses, implants and body electrodes and processes for their manufacture |
JP2000513988A (en) * | 1997-06-18 | 2000-10-24 | ボストン サイエンティフィック リミテッド | Polycarbonate-polyurethane dispersion for antithrombotic coating |
US6110483A (en) | 1997-06-23 | 2000-08-29 | Sts Biopolymers, Inc. | Adherent, flexible hydrogel and medicated coatings |
US5980928A (en) | 1997-07-29 | 1999-11-09 | Terry; Paul B. | Implant for preventing conjunctivitis in cattle |
US5897911A (en) * | 1997-08-11 | 1999-04-27 | Advanced Cardiovascular Systems, Inc. | Polymer-coated stent structure |
US6121027A (en) | 1997-08-15 | 2000-09-19 | Surmodics, Inc. | Polybifunctional reagent having a polymeric backbone and photoreactive moieties and bioactive groups |
US6015541A (en) * | 1997-11-03 | 2000-01-18 | Micro Therapeutics, Inc. | Radioactive embolizing compositions |
WO1999024174A1 (en) * | 1997-11-10 | 1999-05-20 | Katoot Mohammad W | Method for modifying the surface of an object |
US6096396A (en) | 1998-01-21 | 2000-08-01 | Rexam Industries Corp. | Decorative sheet material suitable for use as a flexible weatherable paint film or decal |
DE69918607T2 (en) * | 1998-03-05 | 2005-07-21 | Solvay Solexis, Inc., Wilmington | Weather resistant coating compositions of polyvinylidene fluoride containing polymethylmethacrylate |
US6110188A (en) | 1998-03-09 | 2000-08-29 | Corvascular, Inc. | Anastomosis method |
US20020099438A1 (en) | 1998-04-15 | 2002-07-25 | Furst Joseph G. | Irradiated stent coating |
US20010029351A1 (en) | 1998-04-16 | 2001-10-11 | Robert Falotico | Drug combinations and delivery devices for the prevention and treatment of vascular disease |
US7658727B1 (en) | 1998-04-20 | 2010-02-09 | Medtronic, Inc | Implantable medical device with enhanced biocompatibility and biostability |
ES2179646T3 (en) * | 1998-04-27 | 2003-01-16 | Surmodics Inc | COATING THAT RELEASES A BIOACTIVE AGENT. |
US20020188037A1 (en) | 1999-04-15 | 2002-12-12 | Chudzik Stephen J. | Method and system for providing bioactive agent release coating |
US6113629A (en) | 1998-05-01 | 2000-09-05 | Micrus Corporation | Hydrogel for the therapeutic treatment of aneurysms |
US6153252A (en) | 1998-06-30 | 2000-11-28 | Ethicon, Inc. | Process for coating stents |
NL1009551C2 (en) | 1998-07-03 | 2000-01-07 | Cordis Europ | Vena cava filter with improvements for controlled ejection. |
US5921933A (en) * | 1998-08-17 | 1999-07-13 | Medtronic, Inc. | Medical devices with echogenic coatings |
AU771367B2 (en) | 1998-08-20 | 2004-03-18 | Cook Medical Technologies Llc | Coated implantable medical device |
US6187024B1 (en) * | 1998-11-10 | 2001-02-13 | Target Therapeutics, Inc. | Bioactive coating for vaso-occlusive devices |
US6090134A (en) * | 1999-02-16 | 2000-07-18 | Polymerex Medical Corp. | Surface fluorinated stent and methods thereof |
EP1033125B1 (en) * | 1999-03-03 | 2003-09-24 | Kuraray Co., Ltd. | Relining material for dentures |
MXPA01012959A (en) * | 1999-06-28 | 2002-07-30 | California Inst Of Techn | Microfabricated elastomeric valve and pump systems. |
US6258121B1 (en) | 1999-07-02 | 2001-07-10 | Scimed Life Systems, Inc. | Stent coating |
US6503556B2 (en) * | 2000-12-28 | 2003-01-07 | Advanced Cardiovascular Systems, Inc. | Methods of forming a coating for a prosthesis |
US6790228B2 (en) | 1999-12-23 | 2004-09-14 | Advanced Cardiovascular Systems, Inc. | Coating for implantable devices and a method of forming the same |
US6203551B1 (en) * | 1999-10-04 | 2001-03-20 | Advanced Cardiovascular Systems, Inc. | Chamber for applying therapeutic substances to an implant device |
US6638259B1 (en) | 1999-10-28 | 2003-10-28 | Scimed Life Systems, Inc. | Biocompatible medical devices |
US6776796B2 (en) | 2000-05-12 | 2004-08-17 | Cordis Corportation | Antiinflammatory drug and delivery device |
US6716444B1 (en) * | 2000-09-28 | 2004-04-06 | Advanced Cardiovascular Systems, Inc. | Barriers for polymer-coated implantable medical devices and methods for making the same |
US6254632B1 (en) * | 2000-09-28 | 2001-07-03 | Advanced Cardiovascular Systems, Inc. | Implantable medical device having protruding surface structures for drug delivery and cover attachment |
WO2002026281A1 (en) | 2000-09-29 | 2002-04-04 | Cordis Corporation | Coated medical devices |
US20020051730A1 (en) * | 2000-09-29 | 2002-05-02 | Stanko Bodnar | Coated medical devices and sterilization thereof |
US6746773B2 (en) * | 2000-09-29 | 2004-06-08 | Ethicon, Inc. | Coatings for medical devices |
US20020111590A1 (en) | 2000-09-29 | 2002-08-15 | Davila Luis A. | Medical devices, drug coatings and methods for maintaining the drug coatings thereon |
JP5100951B2 (en) | 2000-09-29 | 2012-12-19 | コーディス・コーポレイション | Coated medical device |
US6863685B2 (en) | 2001-03-29 | 2005-03-08 | Cordis Corporation | Radiopacity intraluminal medical device |
US7261735B2 (en) | 2001-05-07 | 2007-08-28 | Cordis Corporation | Local drug delivery devices and methods for maintaining the drug coatings thereon |
US20020090389A1 (en) | 2000-12-01 | 2002-07-11 | Humes H. David | Intravascular blood conditioning device and use thereof |
US6545097B2 (en) * | 2000-12-12 | 2003-04-08 | Scimed Life Systems, Inc. | Drug delivery compositions and medical devices containing block copolymer |
US6663662B2 (en) | 2000-12-28 | 2003-12-16 | Advanced Cardiovascular Systems, Inc. | Diffusion barrier layer for implantable devices |
EP1383504A1 (en) * | 2001-04-26 | 2004-01-28 | Control Delivery Systems, Inc. | Sustained release drug delivery system containing codrugs |
US7247313B2 (en) | 2001-06-27 | 2007-07-24 | Advanced Cardiovascular Systems, Inc. | Polyacrylates coatings for implantable medical devices |
US6585755B2 (en) * | 2001-06-29 | 2003-07-01 | Advanced Cardiovascular | Polymeric stent suitable for imaging by MRI and fluoroscopy |
US7195640B2 (en) * | 2001-09-25 | 2007-03-27 | Cordis Corporation | Coated medical devices for the treatment of vulnerable plaque |
US7108701B2 (en) * | 2001-09-28 | 2006-09-19 | Ethicon, Inc. | Drug releasing anastomosis devices and methods for treating anastomotic sites |
US20030065377A1 (en) * | 2001-09-28 | 2003-04-03 | Davila Luis A. | Coated medical devices |
US20030073961A1 (en) * | 2001-09-28 | 2003-04-17 | Happ Dorrie M. | Medical device containing light-protected therapeutic agent and a method for fabricating thereof |
US20030077312A1 (en) * | 2001-10-22 | 2003-04-24 | Ascher Schmulewicz | Coated intraluminal stents and reduction of restenosis using same |
US7005137B1 (en) * | 2002-06-21 | 2006-02-28 | Advanceed Cardiovascular Systems, Inc. | Coating for implantable medical devices |
US7217426B1 (en) * | 2002-06-21 | 2007-05-15 | Advanced Cardiovascular Systems, Inc. | Coatings containing polycationic peptides for cardiovascular therapy |
US20040063805A1 (en) * | 2002-09-19 | 2004-04-01 | Pacetti Stephen D. | Coatings for implantable medical devices and methods for fabrication thereof |
US7094256B1 (en) | 2002-12-16 | 2006-08-22 | Advanced Cardiovascular Systems, Inc. | Coatings for implantable medical device containing polycationic peptides |
JP2007517776A (en) * | 2003-12-09 | 2007-07-05 | スフェリックス, インコーポレイテッド | Bioadhesive polymers with catechol functional groups |
US7244443B2 (en) | 2004-08-31 | 2007-07-17 | Advanced Cardiovascular Systems, Inc. | Polymers of fluorinated monomers and hydrophilic monomers |
US8568872B2 (en) * | 2005-08-24 | 2013-10-29 | Eth Zurich | Catechol functionalized polymers and method for preparing them |
-
2008
- 2008-01-31 US US12/023,953 patent/US8791171B2/en not_active Expired - Fee Related
-
2009
- 2009-01-22 WO PCT/US2009/031691 patent/WO2009099768A2/en active Application Filing
-
2014
- 2014-07-03 US US14/323,816 patent/US9603976B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050288398A1 (en) * | 2001-07-20 | 2005-12-29 | Messersmith Phillip B | Polymeric compositions and related methods of use |
WO2008019352A1 (en) * | 2006-08-04 | 2008-02-14 | Nerites Corporation | Biomimetic compounds and synthetic methods therefor |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2784101A1 (en) * | 2013-03-28 | 2014-10-01 | Nitto Europe N.V | Hydroxyphenyl functionalized poly(ester amide) |
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US8791171B2 (en) | 2014-07-29 |
US20090149568A1 (en) | 2009-06-11 |
US9603976B2 (en) | 2017-03-28 |
US20140322294A1 (en) | 2014-10-30 |
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