CA2272582A1 - Process for preparing polymer coatings grafted with polyethylene oxide chains containing covalently bonded bio-active agents - Google Patents

Process for preparing polymer coatings grafted with polyethylene oxide chains containing covalently bonded bio-active agents Download PDF

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Publication number
CA2272582A1
CA2272582A1 CA002272582A CA2272582A CA2272582A1 CA 2272582 A1 CA2272582 A1 CA 2272582A1 CA 002272582 A CA002272582 A CA 002272582A CA 2272582 A CA2272582 A CA 2272582A CA 2272582 A1 CA2272582 A1 CA 2272582A1
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bio
hydrophilic
group
spacer
polymer backbone
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CA002272582A
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French (fr)
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CA2272582C (en
Inventor
Birendra K. Patnaik
Richard J. Zdrahala
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Boston Scientific Ltd Barbados
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Individual
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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
    • A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
    • A61L33/0005—Use of materials characterised by their function or physical properties
    • A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
    • A61L33/0029—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate using an intermediate layer of polymer
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
    • A61L33/0005—Use of materials characterised by their function or physical properties
    • A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
    • 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
    • Y10S623/90—Stent for heart valve
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Abstract

Disclosed are bio-active coating compositions for polymeric substrates. In particular, a bio-active coating is described which is the reaction product formed by providing a polymer backbone with at least one free isocyanate group, wherein the isocyanate group is pendant from the polymer backbone. There is further provided a hydrophilic, amine-terminated spacer which has at least one amine group at its first and second ends. One of the amine groups of the spacer is reacted with one or more of the isocyanate groups on the polymer backbone in the presence of an optional catalyst agent. A bio-active agent is then covalently bonded onto an unreacted end of the spacer in the presence of a catalyst. Also disclosed are coating compositions for a substrate and methods of preparing same.

Claims (41)

1) A bio-active composition for coating a substrate, said composition formed by the process comprising:
a) providing a polymer backbone with at least one free reactive functionality independent of any urethane linkages present in said backbone, wherein said at least one free reactive functionality is pendant from said polymer backbone and is reactive with a functional group on an end of a hydrophilic spacer;
b) further providing said hydrophilic spacer having at least one reactive functional group at its first and second ends;
c) reacting one of said reactive functional groups on said spacer with one or more of said reactive functionalitics on said polymer backbone; and d) covalently bonding a bio-active agent onto an unreacted functional group of said spacer, wherein said bio-active agent is linked to said spacer via an amide bond.
2) The bio-active coating of claim 1, wherein said poly(urethane) polymer backbone is selected from the group consisting of a segmented poly(esterurethane)urea, a poly(carbonateurethane)urea, a poly(etherurethane)urea and mixtures thereof.
3) The bio-active coating of claim 1, wherein said at least one pendant reactive functionality is selected from the group consisting of isocyanalc, carboxyl, amine, and mixtures thereof.
4) The bio-active coating of claim 1, wherein said hydrophilic spacer is selected from the group consisting of aliphatic hydrocarbons, poly(oxy olefins), hydrophilic polyethers, hydrophilic polyethylenes, hydrophilic polyolefins, aliphatic polyesters, polyamines, polysiloxanes, polysilazanes, hydrophilic acrylates, hydrophilic methacrylates, polyamino acids, and linear polysaccharides.
5) The bio-active coating of claim 1, wherein said reactive functional group on said spacer is selected from the group consisting of NH2, COOK, NCO and mixtures thereof.
6) The bio-active coating of claim 1, wherein said hydrophilic spacer is an amine-terminated poly(ethylene oxide).
7) The bio-active coiling of claim 6, wherein slid amine-terminated poly(ethylene oxide) has a molecular weight of about 100 daltons to about 200,000 daltons.
8) The bio-active coating of claim 6, wherein said amine-terminated polyethylene oxide, has a molecular weight of about 200 to about 50,000 daltons.
9) The bio-active coiling of claim 6, wherein said amine-terminated polyethylene oxide, has a molecular weight of about 1,000 to about 4,000 daltons.
10) The bio-active coating of claim 1, wherein the molecular weight of said hydrophilic spacer positions said bio-active agent at a bio-effective distance from said polymer backbone.
11) The bio-active coating of claim 1, wherein said bio-active agent is selected from the group consisting of anti-thrombogenic agents, antibiotic agents, antiviral agents, their pharmaceutical salts and mixtures thereof.
12) The bio-active coating of claim 1, wherein said bio-active agent is selected from the group consisting of heparin, an aldehyde-terminated heparin, and pharmaceutical salts thereof.
13) The bio-active coating of claim 1, wherein 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride separately catalyses the reaction of said spacer with said polymer backbone and said covalent bonding of said bio-active agent to said spacer.
14) A cooing composition for a substrate that includes a polymer backbone having a reactive functionality independent of any urethane linkages therein and at least one pendant moiety bonded to said reactive functionality, said pendant moiety selected from the group consisting of:

wherein R1 is a spacer selected from the group consisting of aliphatic hydrocarbons, poly(oxy olefins), hydrophilic polyethers, hydrophilic polyethylenes, hydrophilic polyolefins, aliphatic polyesters, polyamines, polysiloxanes, polysilazanes, hydrophilic acrylates, hydrophilic methacrylates, polyamino acids, and linear polysaccharides; and R2 is a bio-active agent selected from the group consisting of antithrombogenic agents, antibiotics, antibacterial agents, antiviral agents, their pharmaceutical salts and mixtures thereof.
15) The coating composition of claim 14, wherein said pendant reactive functionality is an isocyanate functionality.
16) The coating composition of claim 14, wherein R1 is a reaction product of a reaction between said reactive functionality and an amine terminated poly(ethylene oxide).
17) The coating composition of claim 16, wherein said amine-terminated poly(ethylene oxide) has a molecular weight of about 100 daltons to about 200,000 daltons.
18) The coating composition of claim 16 wherein said amine-terminated poly(ethylene oxide) has a molecular weight of about 50 to about 200,000 daltons.
19) The coating composition of claim 16, wherein said amine-terminated poly(ethylene oxide) has a molecular weight of about 1,000 to about 4,000 daltons.
20) The coating composition of claim 14, wherein the molecular weight of said spacer positions said bio-active agent at a bio-effective distance from said polymer backbone.
21) The coating composition of claim 14, wherein said antithrombogenic agent is selected from the group consisting of heparin, aldehyde-terminated heparin and pharmaceutical silts thereof.
22) The coating composition of claim 14, wherein said polymer backbone is a polyurethane selected from the group consisting of a segmented poly(esterurethane)urea, a poly(carbonateurethane)urea, a poly(etherurethane)urea, and mixtures thereof.
23) A method for preparing a bio-active polymer coating having a bio-active group covalently bonded through a hydrophilic spacer group to a polymer backbone comprising:
a) introducing a reactive functionality into said polymer backbone, wherein said reactive functionality is independent of any urethane linkages present in said polymer backbone and said reactive functionality being reactive with a reactive functional group on a terminal end of said hydrophilic spacer;
b) reacting said reactive functionality of said polymer backbone with said hydrophilic spacer, wherein said spacer has at least one reactive functional group at its terminal ends to attach said spacer as a pendant group off of said backbone; and d) further reacting sail pendant group with a bio-active agent to covalently bond said pendant group via a chemical group selected from the group consisting of NHCO, NHCOO, and NHCONH.
24) The method of claim 23, wherein said reactive functionality on said polymer backbone is reacted with a hydrophilic spacer selected from the group consisting of aliphatic hydrocarbons, poly(oxy olefins), hydrophilic polyethers, hydrophilic polyethylenes, hydrophilic polyolefins, aliphatic polyesters, polyamines, polysiloxanes, polysilazanes, hydrophilic acrylates, hydrophilic methacrylates, polyamino acids, and linear polysaccharides.
25) The method of claim 23, wherein said reactive functional group of said spacer is selected from the group consisting of NH2, COOH, NCO and mixtures thereof.
26) The method of claim 23, wherein said reactive functionality of said polymer backbone is reacted with a hydrophilic, amine-terminated polyethylene oxide).
27) The method of claim 23, wherein said reactive functionality of said polymer backbone is reacted with a hydrophilic, amine-terminated poly(ethylene oxide) having a molecular weight of about 100 daltons to about 200,000 daltons.
28) The method of claim 23, wherein said reactive functionality of said backbone is reacted with a hydrophilic, amine-terminated poly(ethylene oxide) having a molecular weight of about 200 to about 50,000 daltons.
29) The method of claim 23, wherein said reactive functionality of said polymer backbone is reacted with an amine-terminated poly(ethylene oxide) having a molecular weight of about 1,000 to about 4,000 daltons.
30) The method of claim 23, wherein said hydrophilic spacer positions said bio-active agent at an effective distance tram said polymer backbone, said effective distance being determined by the molecular weight of said spacer.
31) The method of claim 23, wherein said pendant group reacts with said bio-active agent which is selected front the group consisting of anti-thrombogenic agents, antibiotic agents, antibacterial agents, antiviral agents, their pharmaceutical salts, and mixtures thereof.
32) The method of claim 23, wherein said pendant group reacts with heparin, aldehyde-terminated heparin and pharmaceutical salts thereof.
33) The method of claim 23, wherein said further reacting said pendant group with a bio-active agent occurs in the presence of a catalyst.
34) The method of claim 23, wherein 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride separately catalyzes the reaction of said backbone with said spacer and said spacer with said bio-active agent.
35) A polymer-bound bio-active composition represented by the structure:

wherein P is a biocompatible polymer backbone having reactive functionality selected from the group consisting of isocyanates, carboxyls, amines, and mixtures thereof; and wherein said reactive functioinality is independent of any urethane linkages present in said polymer backbone; R1 is a hydrophilic spacer group selected from the group consisting of aliphatic hydrocarbons, poly(oxy olefins), hydrophilic polyethers, hydrophilic polyethylenes, hydrophilic polyolefins, aliphatic polyesters, polyamines, polysiloxanes, polysilazanes, hydrophilic acrylates, hydrophilic methacrylates, polyamino acids, and linear polysaccharides; and R2 is a bio-active agent selected from the group consisting of antithrombogenic agents, antibiotics, antibacterial agents, antiviral agents, their pharmaceutical salts and mixtures thereof.
36) The bio-active composition of claim 35, wherein said polymer backbone is a polyurethane selected from the group consisting of segmented poly(esterurethane)urea, poly(carbonate)urethaneurea, poly(etherurethane)urea, and mixtures thereof.
37) The bio-active composition of claim 35, wherein R1 is a reaction product of a reaction between said reactive functionality and an amine-terminated poly(ethylene oxide).
38) The bio-active composition of claim 37, wherein said amine-terminated of ethylene oxide, has a molecular weight of about 100 daltons to about 200,000 daltons.
39) The bio-active coating of claim 35, wherein the molecular weight of said hydrophilic spacer positions said bio-active agent at a bio-effective distance from said polymer backbone.
40) The bio-active coating of claim 35, wherein said bio-active agent is selected from the group consisting of heparin, aldehyde-terminated heparin and pharmaceutical salts thereof.
41) A bio-active composition for coating a substrate, said composition having a polymer backbone and a bio-active agent bound thereto through a pendant hydrophilic spacer group, said coating comprising the reaction product of a polymer backbone leaving at least one free reactive pendant group, said reactive pendant group being independent of any urethane linkage present in said polymer backbone and said reactive pendant group further being reactive with a reactive functional group on a terminal end of said hydrophilic spacer, said hydrophilic spacer leaving at its first and second terminal ends at least one functional group reactive with said free pendant reactive functional group;
and a bio-active agent covalently reactive with an unreacted functional group in said hydrophilic spacer to form an amide residue linking said bio-active agent to said hydrophilic spacer.
CA2272582A 1996-11-25 1997-11-18 Process for preparing polymer coatings grafted with polyethylene oxide chains containing covalently bonded bio-active agents Expired - Fee Related CA2272582C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/755,189 1996-11-25
US08/755,189 US5877263A (en) 1996-11-25 1996-11-25 Process for preparing polymer coatings grafted with polyethylene oxide chains containing covalently bonded bio-active agents
PCT/US1997/021153 WO1998023306A1 (en) 1996-11-25 1997-11-18 Process for preparing polymer coatings grafted with polyethylene oxide chains containing covalently bonded bio-active agents

Publications (2)

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CA2272582A1 true CA2272582A1 (en) 1998-06-04
CA2272582C CA2272582C (en) 2010-01-26

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CA2272582A Expired - Fee Related CA2272582C (en) 1996-11-25 1997-11-18 Process for preparing polymer coatings grafted with polyethylene oxide chains containing covalently bonded bio-active agents

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US (3) US5877263A (en)
EP (1) EP0946217B1 (en)
AU (1) AU743447B2 (en)
CA (1) CA2272582C (en)
DE (1) DE69735067T2 (en)
WO (1) WO1998023306A1 (en)

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