CA2404683A1 - Compositions of crosslinkable prepolymers for biodegradable implants - Google Patents

Compositions of crosslinkable prepolymers for biodegradable implants Download PDF

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Publication number
CA2404683A1
CA2404683A1 CA002404683A CA2404683A CA2404683A1 CA 2404683 A1 CA2404683 A1 CA 2404683A1 CA 002404683 A CA002404683 A CA 002404683A CA 2404683 A CA2404683 A CA 2404683A CA 2404683 A1 CA2404683 A1 CA 2404683A1
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Canada
Prior art keywords
composition according
crosslinkable
composition
prepolymer
biologically
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Granted
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CA002404683A
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French (fr)
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CA2404683C (en
Inventor
Etienne Honore Schacht
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Universiteit Gent
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Individual
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Publication of CA2404683A1 publication Critical patent/CA2404683A1/en
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Publication of CA2404683C publication Critical patent/CA2404683C/en
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Expired - Fee Related legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/50Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54Biologically active materials, e.g. therapeutic substances
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS 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
    • A61L27/00Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14Macromolecular materials
    • A61L27/16Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14Polymers provided for in subclass C08G
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91Polymers modified by chemical after-treatment
    • C08G63/912Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/60Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
    • A61L2300/602Type of release, e.g. controlled, sustained, slow
    • A61L2300/604Biodegradation

Abstract

A composition suitable for preparing a biodegradable implant, comprising a crosslinkable multifunctional prepolymer having at least two polymerizable end groups, the said composition having a viscosity such that it is deformable at a temperature of 0° to 60 °C into a three-dimensional shape and being crosslinkable within the said temperature range. The prepolymer comprises a hydrophilic region and/or the composition further comprises an effective amount of a mineral biologically-active component delivery system and/or a biocompatible degradable porosity-inducing component.

Claims (31)

1. A composition suitable for preparing a biodegradable implant, comprising a crosslinkable multifunctional prepolymer having at least two polymerizable end groups, the said composition having a viscosity such that it is deformable at a temperature of 0° to 60°C into a three-dimensional shape and being crosslinkable within the said temperature range, wherein the said crosslinkable multifunctional prepolymer comprises a hydrophilic region.
2. A composition suitable for preparing a biodegradable implant, comprising a crosslinkable multifunctional prepolymer having at least two polymerizable end groups, the said composition having a viscosity such that it is deformable at a temperature of 0° to 60°C into a three-dimensional shape and being crosslinkable within the said temperature range, wherein the said composition further comprises an effective amount of a mineral biologically-active component delivery system.
3. A composition suitable for preparing a biodegradable implant, comprising a crosslinkable multifunctional prepolymer having at least two polymerizable end groups, the said composition having a viscosity such that it is deformable at a temperature of 0° to 60°C into a three-dimensional shape and being crosslinkable within the said temperature range, wherein the said composition further comprises an effective amount of a biocompatible degradable porosity-inducing component.
4. A composition according to any of claims 1 to 3, wherein the number average molecular weight of the said crosslinkable multifunctional prepolymer is in the range of 150 to 20,000.
5. A composition according to any of claims 1 to 4, wherein the said crosslinkable multifunctional prepolymer comprises at least one biodegradable region and at least one polymerizable region.
6. A composition according to claim 1, wherein the hydrophilic region of the said crosslinkable multifunctional prepolymer is a polyethylene glycol or a copolymer of ethylene oxide and an alkylene oxide with a degree of polymerization in the range of 2 to 500.
7. A composition according to claim 5, wherein the biodegradable region of the said crosslinkable multifunctional prepolymer is a predominantly amorphous region.
8. A composition according to any of claims 1 to 7, wherein the said crosslinkable multifunctional prepolymer comprises a polyacetal sequence.
9. A composition according to claim 2, wherein the said crosslinkable multifunctional prepolymer comprises a sequence which is able to generate acidic compounds.
10. A composition according to any of claims 1 to 9, wherein the said crosslinkable multifunctional prepolymer comprises a polyester sequence, resulting from copolymerizing a mixture of lactones wherein none of the lactone comonomers is present in the resulting polyester sequence in a molar proportion above 75%, or comprises a polyorthoester sequence or a combination of a polyester sequence and a polyorthoester sequence.
11. A composition according to claim 5, wherein the polymerizable region contains ethylenic and/or acetylenic unsaturations.
12. A composition according to any of claims 1 to 11, further comprising at least one additive selected from biocompatible unsaturated functional monomers and polymerization initiators including redox initiators or photoinitiators.
13. A composition according to claim 2 or claim 9, wherein the mineral biologically-active component delivery system is selected from demineralized bone, resorbable calcium phosphate-based particles, hydroxyapatite, tricalcium phosphate, octacalcium phosphate, calcium carbonate, calcium sulfate and coral.
14.A composition according to any of claims 2, 9 and 13, wherein the mineral biologically-active component delivery system is present in an amount able to increase the pH within the degrading polymer.
15.A composition according to any of claims 2, 9, 13 and 14, wherein the weight ratio mineral system:prepolymer is in the range from 0.05:1 to 20:1.
16. A composition according to any of claims 2, 9, 13 and 14, wherein the mineral biologically-active component delivery system is in the form of a powder.
17. A composition according to claim 3, wherein the biocompatible degradable porosity-inducing component is a monosaccharide, an oligosaccharide, a polysaccharide or a chemically-modified derivative thereof.
18. A composition according to claim 3, wherein the biocompatible degradable porosity-inducing component is a crosslinked gelatine.
19. A composition according to claim 3, wherein the biocompatible degradable porosity-inducing component is a synthetic polymeric porous particle.
20. A composition according to claim 3, wherein the weight ratio porosity-inducing component:prepolymer is in the range from 0.05:1 to 20:1.
21. A composition according to any of claims 1 to 19, further comprising a biologically-active component.
22. A composition according to claim 21, wherein the biologically-active component is selected from bone repair promoters, antimicrobial agents, proteins, peptides, hormones, carbohydrates, antineoplastic agents, antiangiogenic agents, vasoactive agents, anticoagulants, immunomodulators, cytotoxic agents, antiviral agents, antibodies, neurotransmitters, oligonucleotides, lipids, plasmids, DNA and diagnostic agents.
23. A composition according to claim 21, wherein the biologically-active component is a ligand with affinity for cells, or a chemically modified derivative thereof.
24. A composition according to claim 23, wherein the ligand is a protein selected from fibronectin, vitronectin and oligopeptides having from 3 to 25 amino-acids, or a chemically modified derivative thereof.
25. A composition according to claim 23, wherein the ligand or chemically modified derivative thereof is covalently anchored into the polymer matrix resulting from crosslinking of the functional prepolymer.
26. A composition according to any of claims 23 to 25, wherein the weight ratio ligand:prepolymer is in the range from 0.002:1 to 0.65:1.
27.A composition according to claim 3, further comprising a biologically-active component, wherein the said biocompatible degradable porosity-inducing component and the said biologically-active component are in proportions such that as to provide a synergistic effect in bone reconstruction.
28. Use of a composition according to any of claims 1 to 27 for the preparation of a therapeutically-active biodegradable implant.
29. Use according to claim 28, wherein the implant is a bone implant or a bone cement.
30. Use according to claim 28 for the fixation of a dental material or implant.
31. A method for repairing a bone defect by implanting a bone repair low viscosity formulation into the body of a mammal at a place suitable for bone growth and further crosslinking the said formulation, wherein the said formulation comprises a composition according to any of claims 1 to 27.
CA2404683A 2000-04-03 2001-04-03 Compositions of crosslinkable prepolymers for biodegradable implants Expired - Fee Related CA2404683C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP00201198A EP1142596A1 (en) 2000-04-03 2000-04-03 Compositions of crosslinkable prepolymers for use in therapeutically active biodegradable implants
EP00201198.9 2000-04-03
PCT/EP2001/003766 WO2001074411A1 (en) 2000-04-03 2001-04-03 Compositions of crosslinkable prepolymers for biodegradable implants

Publications (2)

Publication Number Publication Date
CA2404683A1 true CA2404683A1 (en) 2001-10-11
CA2404683C CA2404683C (en) 2011-02-08

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Family Applications (1)

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CA2404683A Expired - Fee Related CA2404683C (en) 2000-04-03 2001-04-03 Compositions of crosslinkable prepolymers for biodegradable implants

Country Status (7)

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US (1) US6933328B2 (en)
EP (2) EP1142596A1 (en)
AT (1) ATE329630T1 (en)
AU (2) AU2001262159B2 (en)
CA (1) CA2404683C (en)
DE (1) DE60120660T2 (en)
WO (1) WO2001074411A1 (en)

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Also Published As

Publication number Publication date
DE60120660T2 (en) 2007-06-14
WO2001074411A1 (en) 2001-10-11
US6933328B2 (en) 2005-08-23
EP1267953B1 (en) 2006-06-14
US20030114552A1 (en) 2003-06-19
CA2404683C (en) 2011-02-08
DE60120660D1 (en) 2006-07-27
EP1267953A1 (en) 2003-01-02
AU2001262159B2 (en) 2005-07-14
AU6215901A (en) 2001-10-15
EP1142596A1 (en) 2001-10-10
ATE329630T1 (en) 2006-07-15

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