CA2423990A1 - Bone replacement materials utilizing bioabsorbable liquid polymers - Google Patents

Bone replacement materials utilizing bioabsorbable liquid polymers Download PDF

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Publication number
CA2423990A1
CA2423990A1 CA002423990A CA2423990A CA2423990A1 CA 2423990 A1 CA2423990 A1 CA 2423990A1 CA 002423990 A CA002423990 A CA 002423990A CA 2423990 A CA2423990 A CA 2423990A CA 2423990 A1 CA2423990 A1 CA 2423990A1
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CA
Canada
Prior art keywords
medical device
acid
growth factor
glycerol
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002423990A
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French (fr)
Other versions
CA2423990C (en
Inventor
Aruna Nathan
Mora Melican
Kelly R. Brown
Mark C. Zimmerman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ethicon Inc
Original Assignee
Ethicon, Inc.
Aruna Nathan
Mora Melican
Kelly R. Brown
Mark C. Zimmerman
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
Application filed by Ethicon, Inc., Aruna Nathan, Mora Melican, Kelly R. Brown, Mark C. Zimmerman filed Critical Ethicon, Inc.
Publication of CA2423990A1 publication Critical patent/CA2423990A1/en
Application granted granted Critical
Publication of CA2423990C publication Critical patent/CA2423990C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • 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
    • A61L27/40—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L27/44—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix
    • 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
    • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • 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
    • A61L27/40—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L27/44—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix
    • A61L27/48—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix with macromolecular fillers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2400/00—Materials characterised by their function or physical properties
    • A61L2400/06—Flowable or injectable implant compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2430/00—Materials or treatment for tissue regeneration
    • A61L2430/02—Materials or treatment for tissue regeneration for reconstruction of bones; weight-bearing implants

Abstract

The present invention is directed to bone replacement device and compositions containing a synthetic, bioabsorbable, biocompatible liquid polymer that is the reaction product of a polybasic acid or derivative thereof, a polyol and a fatty acid, the liquid polymer having a melting point less than about 40°C, as a determined by differential scanning calorimetry.

Claims (35)

1. A medical device, comprising: a bone replacement material, said bone replacement material comprising a synthetic, bioabsorbable, biocompatible liquid polymer comprising the reaction product of a polybasic acid or derivative thereof, a fatty acid, and a polyol, said liquid polymer having a melting point less than about 40°C, as determined by differential scanning calorimetry.
2. The medical device of claim 1 wherein said liquid polymer comprises the reaction product of said polybasic acid or derivative thereof and a monoglyceride, said monoglyceride comprising the reaction product of said fatty acid and said polyol.
3. The medical device of claim 2 wherein said polybasic acid or derivative thereof is selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid, diglycolic anhydride, glutaric acid, glutaric anhydride, adipic acid, pimelic acid, suberic acid, sebacic acid, fumaric acid, maleic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
4. The medical device of claim 2 wherein said monoglyceride is selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoylglycerol.
5. The medical device of claim 4 wherein said polybasic acid derivative is succinic anhydride.
6. The medical device of claim 4 wherein said polybasic acid is succinic acid.
7. The medical device of claim 1 wherein said liquid polymer comprises a liquid copolymer.
8. The medical device of claim 7 wherein said liquid copolymer comprises the reaction product of said fatty acid, said polyol, and at least two of said polybasic acids or derivatives thereof selected from the group consisting of succinic acid, succinic anhydride, malic acid, tartaric acid, citric acid, diglycolic acid and diglycolic anhydride.
9. The medical device of claim 7 wherein said liquid copolymer comprises the reaction product of said polybasic acid or derivative thereof, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaprolyl glycerol, monodecanoyl glycerol, monolauroylglycerol, monolinoleoyl glycerol and monooleoyl glycerol.
10. The medical device of claim 7 wherein said liquid copolymer comprises the reaction product of said polybasic acid or derivative thereof, a monoglyceride selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,3 propanediol, bis-2-hydroxyethyl ether, 1,4-butanediol, 1,5-pentanediol 1,6- hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, other diols, linear poly(ethylene glycol), branched poly(ethylene glycol), linear poly(propylene glycol), branched poly(propylene glycol), linear poly(ethylene-co-propylene glycol)s and branched poly(ethylene-co-propylene glycol)s.
11. The medical device of claim 1 further comprising an inorganic filler.
12. The medical device of claim 11 wherein said inorganic filler is selected form the group consisting of alpha-tricalcium phosphate, bet-tricalcium phosphate, calcium carbonate, barium carbonate, calcium sulfate, barium sulfate and hydroxyapatite.
13. The medical device of claim 11 wherein said inorganic filler comprises a polymorph of calcium phosphate.
14. The medical device of claim 11 wherein said inorganic filler is hydroxyapatite.
15. The medical device of claim 11 further comprising a therapeutically effective amount of a bioactive agent.
16. The medical device of claim 15 wherein said bioactive agent is a growth factor.
17. The medical device of claim 16 wherein said growth factor is selected from the group consisting of cell attachment mediators, biologically active ligands, integrin binding sequence, bone morphogenic proteins, epidermal growth factor, fibroblast growth factor, platelet-derived growth factor, IGF-I, IGF-II, TGF-.beta. I-III, growth differentiation factor, parathyroid hormone, vascular endothelial growth factor, hyaluronic acid, glycoprotein, lipoprotein, bFGF, TGF.beta. superfamily factors, BMP-2, BMP-4, BMP-6, BMP-12, sonic hedgehog, GDF5, GDF6, GDF8, PDGF, tenascin-C, fibronectin, thromboelastin, and thrombin-derived peptides.
18. The medical device of claim 11 further comprising a biologically derived substance selected from the group consisting of demineralized bone, platelet rich plasma, bone marrow aspirate and bone fragments.
19. The medical device of claim 1 further comprising a therapeutically effective amount of a bioactive agent.
20. The medical device of claim 19 wherein said bioactive agent is a growth factor.
21. The medical device of claim 20 wherein said growth factor is selected from the group consisting of cell attachment mediators, biologically active ligands, integrin binding sequence, bone morphogenic proteins, epidermal growth factor, fibroblast growth factor, platelet-derived growth factor, IGF-I, IGF-II, TGF-.beta. I-III, growth differentiation factor, parathyroid hormone, vascular endothelial growth factor, hyaluronic acid, glycoprotein, lipoprotein, bFGF, T6F.beta. superfamily factors, BMP-2, BMP-4, BMP-6, BMP-12, sonic hedgehog, GDF5, GDF6, GDF8, PDGF, tenascin-C, fibronectin, tispoelastin, and thromlin-derived peptides.
22. The medical device of claim 1 further comprising terminal and pendant chemical moieties prepared by suitable endcapping reactions.
23. The medical device of claim 22 wherein said terminal and pendant chemical moieties are selected from the group consisting of ethers, esters, anhydrides, mixed anhydrides, sulfonates, and urethanes.
24. The medical device of claim 22 further comprising and inorganic filler.
25. The medical device of claim 24 wherein said inorganic filler is selected from the group consisting of alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium carbonate, barium carbonate, calcium sulfate, barium sulfate and hydroxyapatite.
26. The medical device of claim 24 wherein said organic filler comprises a polymorph of calcium phosphate.
27. The medical device of claim 24 wherein said inorganic filler is hydroxyapatite.
28. The medical device of claim 24 further comprising a therapeutically effective amount of a bioactive agent.
29. The medical device of claim 28 wherein said bioactive agent is a growth factor.
30. The medical device of claim 29 wherein said growth factor is selected from the group consisting of cell attachment mediators, biologically active ligands, integrin binding sequence, bone morphogenic proteins, epidermal growth factor, fibroblast growth factor, platelet-derived growth factor, IGF-I, IGF-II, TGF-.beta. I-III, growth differentiation factor, parathyroid hormone, vascular endothelial, growth factor, hyaluronic acid, glycoprotein and lipoprotein.
31. The medical device of claim 22 further comprising a biologically derived substance selected from the group consisting of demineralized bone, platelet rich plasma, bone marrow aspirate and bone fragments.
32. The medical device of claim 22 further comprising an therapeutically effective amount of a bioactive agent.
33. The medical device of claim 32 wherein said bioactive agent is a growth factor.
34. The medical device of claim 33 wherein said growth factor is selected from the group consisting of cell attachment mediators, biologically active ligands, integrin binding sequence, bone morphogenic proteins, epidermal growth factor, fibroblast growth factor, platelet-derived growth factor IGF-I, IGF-II, TGF-.beta.I-III, growth differentiation factor, parathyroid hormone, vascular endothelial growth factor, hyaluronic acid, glycoprotein and lipoprotein.
35. A bone replacement composition, comprising: a liquid polymer comprising the reaction product of a polybasic acid or derivative thereof, a fatty acid and a polyol, said liquid polymer having a melting point less than about 40°C, as determined by differential scanning calorimetry; and demineralized bone matrix.
CA2423990A 2002-03-29 2003-03-28 Bone replacement materials utilizing bioabsorbable liquid polymers Expired - Fee Related CA2423990C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/112,554 US7005136B2 (en) 2002-03-29 2002-03-29 Bone replacement materials utilizing bioabsorbable liquid polymers
US10/112,554 2002-03-29

Publications (2)

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CA2423990A1 true CA2423990A1 (en) 2003-09-29
CA2423990C CA2423990C (en) 2012-05-29

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US (1) US7005136B2 (en)
EP (1) EP1348450B1 (en)
KR (1) KR20030078779A (en)
CN (1) CN1494924A (en)
AU (1) AU2003203558B2 (en)
CA (1) CA2423990C (en)
DE (1) DE60322767D1 (en)
TW (1) TW200408417A (en)

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AU2003203558A1 (en) 2003-10-23
US20030185871A1 (en) 2003-10-02
US7005136B2 (en) 2006-02-28
AU2003203558B2 (en) 2006-10-26
KR20030078779A (en) 2003-10-08
TW200408417A (en) 2004-06-01
EP1348450A3 (en) 2004-01-28
CA2423990C (en) 2012-05-29
EP1348450A2 (en) 2003-10-01
CN1494924A (en) 2004-05-12
EP1348450B1 (en) 2008-08-13
DE60322767D1 (en) 2008-09-25

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