CA2459801A1 - Poly(l-lactide-co-glycolide) copolymers, methods for making and using same, and devices containing same - Google Patents
Poly(l-lactide-co-glycolide) copolymers, methods for making and using same, and devices containing same Download PDFInfo
- Publication number
- CA2459801A1 CA2459801A1 CA002459801A CA2459801A CA2459801A1 CA 2459801 A1 CA2459801 A1 CA 2459801A1 CA 002459801 A CA002459801 A CA 002459801A CA 2459801 A CA2459801 A CA 2459801A CA 2459801 A1 CA2459801 A1 CA 2459801A1
- Authority
- CA
- Canada
- Prior art keywords
- repeat units
- lactide
- terpolymer
- glycolide
- dimer
- 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.)
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- 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
- A61L31/04—Macromolecular materials
- A61L31/06—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- Y10S606/00—Surgery
- Y10S606/907—Composed of particular material or coated
- Y10S606/91—Polymer
Abstract
The present invention relates in general to implantable, resorbable copolyme rs containing L-lactide and glycolide repeat units, and in particular to terpolymers containing L-lactide, glycolide, and one other type of repeat un it selected from the group consisting of D-lactide, D,L-lactide, and E- caprolactone. Medical devices for in viva implantation applications containi ng such implantable, resorbable copolymers are also described, as well as metho ds for making such copolymers and devices.
Claims (42)
1. An implantable medical device comprising a terpolymer having repeat units of L-lactide, D-lactide, and glycolide.
2. The device of claim 1, which is fabricated into the form of a bone fixation plate, screw, tack, clip, staple, pin, rod, anchor, scaffold, sponge, implant for cell encapsulation, implant for tissue engineering, drug delivery device, monofilament or multifilament structure, sheet, membrane, and a foamed article.
3. The device of claim 1, wherein from about 1% to about 20% of the repeat units of the terpolymer are D-lactide repeat units.
4. The device of claim 3, wherein from about 4% to about 11% of the repeat units of the terpolymer are D-lactide repeat units.
5. The device of claim 1, wherein from about 50% to about 95% of the repeat units of the terpolymer are L-lactide repeat units.
6. The device of claim 5, wherein from about 75% to about 90% of the repeat units of the terpolymer are L-lactide repeat units.
7. The device of claim 1, wherein from about 1% to about 30% of the repeat units of the terpolymer are glycolide repeat units.
8. The device of claim 7, wherein from about 4% to about 18% of the repeat units of the terpolymer are glycolide repeat units.
9. The device of claim 1, wherein the terpolymer comprises from about 75% to about 90% L-lactide repeat units, from about 4% to about 11% D-lactide repeat units, and from about 4% to about 18% glycolide repeat units.
10. The device of claim 1, wherein the terpolymer consists essentially of about 85% L-lactide repeat units, about 5% D-lactide repeat units, and about 10% glycolide repeat units.
11. The device of claim 1, wherein the terpolymer consists essentially of about 90% L-lactide repeat units, about 5% D-lactide repeat units, and about 5% glycolide repeat units.
12. An implantable medical device comprising a terpolymer having repeat units of L-lactide, D,L-lactide, and glycolide.
13. The device of claim 12, wherein the terpolymer comprises at least about 50% L-lactide repeat units, from about 1% to about 20% D,L-lactide repeat units, and from about 1% to about 30% glycolide repeat units.
14. The device of claim 12, wherein the terpolymer consists essentially of about 80% L-lactide repeat units, about 10% D,L-lactide repeat units, and about 10%
glycolide repeat units.
glycolide repeat units.
15. The device of claim 12, wherein the terpolymer consists essentially of about 80% L-lactide repeat units, about 5% D,L-lactide repeat units, and about 15%
glycolide repeat units.
glycolide repeat units.
16. An implantable medical device comprising a terpolymer having repeat units of L-lactide, E-caprolactone, and glycolide.
17. The device of claim 16, wherein the terpolymer comprises at least about 50% L-lactide repeat units, from about 1 % to about 20% repeat units from .epsilon.-caprolactone, and from about 1% to about 30% glycolide repeat units.
18. The device of claim 16, wherein the terpolymer consists essentially of about 80% L-lactide repeat units, about 10% repeat units from .epsilon.-caprolactone, and about 10% glycolide repeat units.
19. The device of claim 1, wherein the terpolymer has a heat of fusion from about 0.5 J/g to about 15 J/g.
20. The device of claim 1, wherein the terpolymer has a heat of fusion from about 0.1 J/g to about 10 J/g.
21. The device of claim 1, wherein the terpolymer has a heat of fusion from about 15 J/g to about 25 J/g.
22. The device of claim 1, wherein the terpolymer has an inherent viscosity from about 2.5 dL/g to about 8 dL/g.
23. The device of claim 1, wherein the terpolymer has an inherent viscosity from about 4 dL/g to about 6.5 dL/g.
24. An implantable medical device comprising a terpolymer having repeat units depicted by the following formula:
wherein the repeat unit having subscript x is an L-lactide repeat unit, the third component having subscript y is a D-lactide repeat unit; the molar percentages of the repeating units are such that x is from about 0.75 to about 0.9, y is from about 0.02 to about 0.16, and z is from about 0.04 to about 0.18; and x+y+z = 1.
wherein the repeat unit having subscript x is an L-lactide repeat unit, the third component having subscript y is a D-lactide repeat unit; the molar percentages of the repeating units are such that x is from about 0.75 to about 0.9, y is from about 0.02 to about 0.16, and z is from about 0.04 to about 0.18; and x+y+z = 1.
25. The device of claim 24, wherein x is from about 0.75 to about 0.9, y is from about 0.04 to about 0.11, and z is from about 0.05 to about 0.15.
26. The device of claim 24, wherein x is essentially about 0.85, y is essentially about 0.05, and z is essentially about 0.1.
27. The device of claim 24, wherein x is essentially about 0.9, y is essentially about 0.05, and z is essentially about 0.05.
28. An implantable medical device comprising the terpolymer of claim 1 made by the process comprising:
combining L-lactic acid monomer, from about 2% to about 16% of D-lactic acid monomer, and glycolic acid monomer to form a monomer mixture;
polymerizing substantially all of the monomer mixture to form the terpolymer.
combining L-lactic acid monomer, from about 2% to about 16% of D-lactic acid monomer, and glycolic acid monomer to form a monomer mixture;
polymerizing substantially all of the monomer mixture to form the terpolymer.
29. An implantable medical device comprising the terpolymer of claim 1 made by the process comprising:
combining L-lactide dimer, D-lactide dimer, and glycolide dimer to form a dimer mixture;
polymerizing substantially all of the dimer mixture to form the terpolymer.
combining L-lactide dimer, D-lactide dimer, and glycolide dimer to form a dimer mixture;
polymerizing substantially all of the dimer mixture to form the terpolymer.
30. An implantable medical device comprising the terpolymer of claim 1 made by the process comprising:
contacting a combination of monomers and dimers that correspond to repeat unit structures of L-lactide, D-lactide, and glycolide to form a monomer-dimer mixture;
polymerizing substantially all of the monomer-dimer mixture to form the terpolymer.
contacting a combination of monomers and dimers that correspond to repeat unit structures of L-lactide, D-lactide, and glycolide to form a monomer-dimer mixture;
polymerizing substantially all of the monomer-dimer mixture to form the terpolymer.
31. An implantable medical device comprising the terpolymer of claim 12 made by the process comprising:
combining L-lactide dimer, D,L-lactide dimer, and glycolide dimer to form a dimer mixture;
polymerizing substantially all of the dimer mixture to form the terpolymer.
combining L-lactide dimer, D,L-lactide dimer, and glycolide dimer to form a dimer mixture;
polymerizing substantially all of the dimer mixture to form the terpolymer.
32. An implantable medical device comprising the terpolymer of claim 12 made by the process comprising:
contacting a combination of monomers and dimers that correspond to repeat unit structures of L-lactide, D,L-lactide, and glycolide to form a monomer-dimer mixture;
polymerizing substantially all of the monomer-dimer mixture to form the terpolymer.
contacting a combination of monomers and dimers that correspond to repeat unit structures of L-lactide, D,L-lactide, and glycolide to form a monomer-dimer mixture;
polymerizing substantially all of the monomer-dimer mixture to form the terpolymer.
33. An implantable medical device comprising the terpolymer of claim 16 made by the process comprising:
combining L-lactic acid monomer, .epsilon.-caprolactone monomer, and glycolic acid monomer to form a monomer mixture;
polymerizing substantially all of the monomer mixture to form the terpolymer.
combining L-lactic acid monomer, .epsilon.-caprolactone monomer, and glycolic acid monomer to form a monomer mixture;
polymerizing substantially all of the monomer mixture to form the terpolymer.
34. An implantable medical device comprising the terpolymer of claim 16 made by the process comprising:
contacting a combination of monomers and dimers that correspond to repeat unit structures of L-lactide, a ring-opened ester from .epsilon.-caprolactone, and glycolide to form a monomer-dimer mixture;
polymerizing substantially all of the monomer-dimer mixture to form the terpolymer.
contacting a combination of monomers and dimers that correspond to repeat unit structures of L-lactide, a ring-opened ester from .epsilon.-caprolactone, and glycolide to form a monomer-dimer mixture;
polymerizing substantially all of the monomer-dimer mixture to form the terpolymer.
35. A terpolymer comprising form about 75% to about 90% L-lactide repeat units, from about 4% to about 11% D-lactide repeat units, and from about 4% to about 18% glycolide repeat units.
36. The terpolymer of claim 35, which consists essentially of about 90%
L-lactide repeat units, about 5% D-lactide repeat units, and about 5%
glycolide repeat units.
L-lactide repeat units, about 5% D-lactide repeat units, and about 5%
glycolide repeat units.
37. The terpolymer of claim 35, which consists essentially of about 85%
L-lactide repeat units, about 5% D-lactide repeat units, and about 10%
glycolide repeat units.
L-lactide repeat units, about 5% D-lactide repeat units, and about 10%
glycolide repeat units.
38. A terpolymer comprising at least about 50% L-lactide repeat units, from about 1 % to about 20% repeat units from .epsilon.-caprolactone, and from about 1% to about 30% glycolide repeat units.
39. The terpolymer of claim 38, which consists essentially of about 80%
L-lactide repeat units, about 10% repeat units from .epsilon.-caprolactone, and about 10% glycolide repeat units.
L-lactide repeat units, about 10% repeat units from .epsilon.-caprolactone, and about 10% glycolide repeat units.
40. A terpolymer comprising at least about 50% L-lactide repeat units, from about 1% to about 20% D,L-lactide repeat units, and from about 1% to about 30%
glycolide repeat units.
glycolide repeat units.
41. The terpolymer of claim 40, which consists essentially of about 80%
L-lactide repeat units, about 10% D,L-lactide repeat units, and about 10%
glycolide repeat units.
L-lactide repeat units, about 10% D,L-lactide repeat units, and about 10%
glycolide repeat units.
42. The terpolymer of claim 40, which consists essentially of about 80%
L-lactide repeat units, about 5% D,L-lactide repeat units, and about 15%
glycolide repeat units.
L-lactide repeat units, about 5% D,L-lactide repeat units, and about 15%
glycolide repeat units.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/945,704 US6747121B2 (en) | 2001-09-05 | 2001-09-05 | Poly(L-lactide-co-glycolide) copolymers, methods for making and using same, and devices containing same |
US09/945,704 | 2001-09-05 | ||
PCT/IB2002/003588 WO2003020330A2 (en) | 2001-09-05 | 2002-09-04 | Poly (l-lactide-co-glycolide) copolymers and medical devices containing same |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2459801A1 true CA2459801A1 (en) | 2003-03-13 |
CA2459801C CA2459801C (en) | 2012-01-10 |
Family
ID=25483444
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2459801A Expired - Fee Related CA2459801C (en) | 2001-09-05 | 2002-09-04 | Poly(l-lactide-co-glycolide) copolymers, methods for making and using same, and devices containing same |
Country Status (5)
Country | Link |
---|---|
US (1) | US6747121B2 (en) |
EP (2) | EP1455856A2 (en) |
JP (1) | JP4515762B2 (en) |
CA (1) | CA2459801C (en) |
WO (1) | WO2003020330A2 (en) |
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- 2002-09-04 WO PCT/IB2002/003588 patent/WO2003020330A2/en not_active Application Discontinuation
- 2002-09-04 JP JP2003524635A patent/JP4515762B2/en not_active Expired - Fee Related
- 2002-09-04 EP EP05016919.2A patent/EP1591132B1/en not_active Expired - Lifetime
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EP1455856A2 (en) | 2004-09-15 |
CA2459801C (en) | 2012-01-10 |
WO2003020330A2 (en) | 2003-03-13 |
JP4515762B2 (en) | 2010-08-04 |
EP1591132A3 (en) | 2014-04-30 |
EP1591132A2 (en) | 2005-11-02 |
US6747121B2 (en) | 2004-06-08 |
WO2003020330A3 (en) | 2003-08-28 |
US20030114637A1 (en) | 2003-06-19 |
JP2005519654A (en) | 2005-07-07 |
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