CA2452951A1 - Functionalized polymers for medical applications - Google Patents
Functionalized polymers for medical applications Download PDFInfo
- Publication number
- CA2452951A1 CA2452951A1 CA002452951A CA2452951A CA2452951A1 CA 2452951 A1 CA2452951 A1 CA 2452951A1 CA 002452951 A CA002452951 A CA 002452951A CA 2452951 A CA2452951 A CA 2452951A CA 2452951 A1 CA2452951 A1 CA 2452951A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- glycerol
- polymer
- beta
- alpha
- 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
Links
Classifications
-
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- 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
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/14—Post-treatment to improve physical properties
- A61L17/145—Coating
-
- 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
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- 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
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/918—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Abstract
The present invention is directed to synthetic, biodegradable, biocompatible polymers that are the reaction product of an .alpha.,.beta.-unsaturated polybasic acid or derivative thereof and a monoglyceride, and which further contain pended thereto a functional agent, and to medical devices and compositions containing such polymers.
Claims (41)
1. A synthetic polymer comprising the reaction product of:
an .alpha.,.beta.-unsaturated polybasic acid or derivative thereof; and a monoglyceride;
and further comprising pended thereto a functional agent comprising a first functional nucleophilic moiety and a second functional moiety other than said first functional moiety.
an .alpha.,.beta.-unsaturated polybasic acid or derivative thereof; and a monoglyceride;
and further comprising pended thereto a functional agent comprising a first functional nucleophilic moiety and a second functional moiety other than said first functional moiety.
2. The polymer of claim 1 wherein said .alpha.,.beta.-unsaturated polybasic acid or derivative thereof is selected from the group consisting of maleic acid, fumaric acic, citraconic acid, itaconic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
3. The polymer of claim 1 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 monooleoyl glycerol.
4. The polymer of claim 3 wherein said .alpha.,.beta.-unsaturated polybasic acid derivative is maleic anhydride.
5. The polymer of claim 3 wherein said .alpha.,.beta.-unsaturated polybasic acid is maleic acid.
6. The polymer of claim 1 wherein said functional agent is selected from the group consisting of mercaptoethanol, mercaptopropanol, mercaptobutanol, mercaptohexanol, mercaptopropanediol, mercaptoacetic acid, mercaptopropionic acid, mercaptosuccinic acid and mercaptoethylamine.
7. The polymer of claim 1 wherein said polymer is branched.
8. The polymer of claim 1 wherein said polymer comprises the reaction product of said monoglyceride, and at least two of said .alpha.,.beta.-unsaturated polybasic acids or derivatives thereof selected from the group consisting of maleic acid, fumaric acic, citraconic acid, itaconic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
9. The polymer of claim 1 wherein said polymer comprises the reaction product of said monoglyceride, said .alpha.,.beta.-unsaturated polybasic acids or derivatives thereof, and a polybasic acid selected from the group consisting of succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid and sebacic acid.
10. The polymer of claim 1 wherein said polymer comprises the reaction product of said .alpha.,.beta.-unsaturated polybasic acid or derivative thereof, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl, glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
11. A composition, comprising: a synthetic, biodegradable, biocompatible polymer comprising the reaction product of:
an .alpha.,.beta.-unsaturated polybasic acid or derivative thereof; and a monoglyceride;
and further comprising pended to said polymer a functional agent comprising a first functional nucleophilic moiety and a second functional moiety other than said first functional moiety.
an .alpha.,.beta.-unsaturated polybasic acid or derivative thereof; and a monoglyceride;
and further comprising pended to said polymer a functional agent comprising a first functional nucleophilic moiety and a second functional moiety other than said first functional moiety.
12. The composition of claim 11 wherein said .alpha.,.beta.-unsaturated polybasic acid or derivative thereof is selected from the group consisting of maleic acid, fumaric acic, citraconic acid, itaconic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
13. The composition of claim 11 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 monooleoyl glycerol.
14. The composition of claim 13 wherein said .alpha.,.beta.-unsaturated polybasic acid derivative is maleic anhydride.
15. The composition of claim 13 wherein said .alpha.,.beta.-unsaturated polybasic acid is maleic acid.
16. The composition of claim 11 wherein said functional agent is selected from the group consisting of mercaptoethanol, mercaptopropanol, mercaptobutanol, mercaptohexanol, mercaptapropanediol, mercaptoacetic acid, mercaptopropionic acid, mercaptosuccinic acid and mercaptoethylamine.
17. The composition of claim 11 wherein said polymer is branched.
18. The composition of claim 1 wherein said polymer comprises the reaction product of said monoglyceride, and at least two of said .alpha.,.beta.-unsaturated polybasic acids or derivatives thereof selected from the group consisting of maleic acid, fumaric acic, citraconic acid, itaconic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
19. The composition of claim 11 wherein said polymer comprises the reaction product of said monoglyceride, and said .alpha.,.beta.-unsaturated polybasic acids or derivatives thereof, and a polybasic acid selected from the group consisting of succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid and sebacic acid.
20. The composition of claim 11 wherein said polymer comprises the reaction product of said .alpha.,.beta.-unsaturated polybasic acid or derivative thereof, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
21. The composition of claim 11 further comprising an effective amount of a bioactive agent
22. The composition of claim 21 wherein said bioactive agent is selected from the group consisting of antiinfectives, analgesics, anorexics, antihelmintics, antiarthritics, antiasthmatics, anticonvulsants, antidepressants, antidiuretics, antidiarrheals, antihistamines, antiinflammatory agents, antimigraine preparations, antinauseants, antineoplastics, antiparkinsonism drugs, antipruritics, antipsychotics, antipyretics, antispasmodics, anticholinergics, sympathomimetics, xanthine derivatives, calcium channel blockers, beta-blockers, antiarrhythmics, antihypertensives, diuretics, vasodilators, central nervous system stimulants, decongestants, hormones, steroids, hypnotics, immunosuppressives, muscle relaxants, parasympatholytics, psychostimulants, sedatives, tranquilizers, naturally derived or genetically engineered proteins, growth factors, polysaccharides, glycoproteins, or lipoproteins, oligonucleotides, antibodies, antigens, cholinergics, chemotherapeutics, hemostatics, clot dissolving agents, radioactive agents and cystostatics.
23. The composition of claim 11 comprising a microdispersion, said microdispersion comprising a solid polymer dispersed in a liquid polymer, wherein one of said solid polymer or said liquid polymer comprise the reaction product of an .alpha.,.beta.-unsaturated polybasic acid or derivative thereof, and a monoglyceride, and further comprising pended to said polymer a functional agent comprising a first functional nucleophilic moiety and a second functional moiety other than said first functional moiety; wherein said solid polymer has a melting point between about 25°C and about 70°C, and wherein said liquid polymer has a melting point below about 25°C.
24. The composition of claim 23 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 monooleoyl glycerol.
25. The composition of claim 24 wherein said .alpha.,.beta.-unsaturated polybasic acid derivative is maleic anhydride.
26. The composition of claim 24 wherein said .alpha.,.beta.-unsaturated polybasic acid is maleic acid.
27. The composition of claim 23 further comprising an effective amount of a bioactive agent.
28. The composition of claim 23 wherein both said solid polymer and said liquid polymer comprise the reaction product of an .alpha.,.beta.-unsaturated polybasic acid or derivative thereof, and a monoglyceride, and further comprising pended to said polymer a functional agent comprising a first functional nucleophilic moiety and a second functional moiety other than said first functional moiety.
29. A medical device comprising a coating, said coating comprising a synthetic, biodegradable, biocompatible polymer comprising the reaction product of an .alpha.,.beta.-unsaturated polybasic acid or derivative thereof and a monoglyceride, and further comprising pended to said polymer a functional agent comprising a first functional nucleophilic moiety and a second functional moiety other than said first functional moiety.
30. The medical device of claim 29 wherein said .alpha.,.beta.-unsaturated polybasic acid or derivative thereof is selected from the group consisting of maleic acid, fumaric acic, citraconic acid, itaconic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
31. The medical device of claim 29 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 monooleoyl glycerol.
32. The medical device of claim 31 wherein said .alpha.,.beta.-unsaturated polybasic acid derivative is maleic anhydride.
33. The medical device of claim 31 wherein said .alpha.,.beta.-unsaturated polybasic acid is maleic acid.
34. The medical device of claim 29 wherein said functional agent is selected from the group consisting of mercaptoethanol, mercaptopropanol, mercaptobutanol, mercaptohexanol, mercaptopropanediol, mercaptoacetic acid, mercaptopropionic acid, mercaptosuccinic acid and mercaptoethylamine.
35. The medical device of claim 32 wherein said polymer is branched.
36. The medical device of claim 29 wherein said polymer comprises the reaction product of said monoglyceride, and at least two of said .alpha.,.beta.-unsaturated polybasic acids or derivatives thereof selected from the group consisting of maleic acid, fumaric acic, citraconic acid, itaconic acid, maleic anhydride, mixed anhydrides, esters, activated esters and acid halides.
37. The medical device of claim 29 wherein said polymer comprises the reaction product of said monoglyceride, and said .alpha.,.beta.-unsaturated polybasic adds or derivatives thereof, and a polybasic acid selected from the group consisting of succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid and sebacic acid.
38. The medical device of claim 29 wherein said polymer comprises the reaction product of said .alpha.,.beta.-unsaturated polybasic acid or derivative thereof, and at least two monoglycerides selected from the group consisting of monostearoyl glycerol, monopalmitoyl glycerol, monomyrisitoyl glycerol, monocaproyl glycerol, monodecanoyl glycerol, monolauroyl glycerol, monolinoleoyl glycerol and monooleoyl glycerol.
39. The medical device of claim 29 further comprising an effective amount of a bioactive agent.
40. The medical device of claim 29 further comprising an aliphatic polyester prepared from the group of monomers selected from the group consisting of glycolide, L-lactide, D-lactide, meso-lactide, rac-lactide, .epsilon.-caprolactone, trimethylene carbonate, p-dioxanone, 1,4-dioxanone, 1,4-dioxepan-2-one, 1,5-dioxepan-2-one and substituted derivatives thereof.
41. The medical device of claim 29 selected from the group consisting of suture anchors, sutures, staples, surgical tacks, clips, plates, screws, drug-delivery devices, adhesion prevention films and foams, and tissue adhesives.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/322,154 | 2002-12-18 | ||
US10/322,154 US6872799B2 (en) | 2002-12-18 | 2002-12-18 | Functionalized polymers for medical applications |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2452951A1 true CA2452951A1 (en) | 2004-06-18 |
CA2452951C CA2452951C (en) | 2012-02-07 |
Family
ID=32393013
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2452951A Expired - Fee Related CA2452951C (en) | 2002-12-18 | 2003-12-12 | Functionalized polymers for medical applications |
Country Status (9)
Country | Link |
---|---|
US (2) | US6872799B2 (en) |
EP (1) | EP1431327B1 (en) |
KR (1) | KR100995482B1 (en) |
CN (1) | CN1513887A (en) |
AT (1) | ATE404605T1 (en) |
AU (1) | AU2003266800B2 (en) |
CA (1) | CA2452951C (en) |
DE (1) | DE60322824D1 (en) |
TW (1) | TWI334874B (en) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69333752T3 (en) * | 1992-06-10 | 2011-03-03 | Nippon Shokubai Co. Ltd. | Process for the preparation of a hydrophilic resin |
EP1253857B1 (en) * | 2000-02-03 | 2009-01-21 | Tissuemed Limited | Device for the closure of a surgical puncture |
DE10026698A1 (en) | 2000-05-30 | 2001-12-06 | Basf Ag | Self-emulsifying active ingredient formulation and use of this formulation |
US9080146B2 (en) * | 2001-01-11 | 2015-07-14 | Celonova Biosciences, Inc. | Substrates containing polyphosphazene as matrices and substrates containing polyphosphazene with a micro-structured surface |
US7326426B2 (en) * | 2002-03-29 | 2008-02-05 | Ethicon, Inc. | Compositions and medical devices utilizing bioabsorbable liquid polymers |
US20080226723A1 (en) * | 2002-07-05 | 2008-09-18 | Celonova Biosciences, Inc. | Loadable Polymeric Particles for Therapeutic Use in Erectile Dysfunction and Methods of Preparing and Using the Same |
EP1610829B1 (en) * | 2003-04-04 | 2010-01-20 | Tissuemed Limited | Tissue-adhesive formulations |
US8377952B2 (en) | 2003-08-28 | 2013-02-19 | Abbott Laboratories | Solid pharmaceutical dosage formulation |
US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
US20110015367A1 (en) * | 2004-06-03 | 2011-01-20 | Cornell University | Unsaturated poly(ester-amide) and poly(ether ester amide) biomaterials |
BRPI0514106A (en) | 2004-08-03 | 2008-05-27 | Tissuemed Ltd | fabric adhesive materials |
US9107850B2 (en) * | 2004-10-25 | 2015-08-18 | Celonova Biosciences, Inc. | Color-coded and sized loadable polymeric particles for therapeutic and/or diagnostic applications and methods of preparing and using the same |
ATE503465T1 (en) | 2004-10-25 | 2011-04-15 | Celonova Biosciences Germany Gmbh | LOADABLE POLYPHOSPHAZENE-CONTAINING PARTICLES FOR THERAPEUTIC AND/OR DIAGNOSTIC APPLICATIONS AND PRODUCTION AND USE METHODS THEREOF |
US20210299056A9 (en) | 2004-10-25 | 2021-09-30 | Varian Medical Systems, Inc. | Color-Coded Polymeric Particles of Predetermined Size for Therapeutic and/or Diagnostic Applications and Related Methods |
US9114162B2 (en) | 2004-10-25 | 2015-08-25 | Celonova Biosciences, Inc. | Loadable polymeric particles for enhanced imaging in clinical applications and methods of preparing and using the same |
AU2007210879B2 (en) * | 2006-02-03 | 2013-01-10 | Tissuemed Limited | Tissue-adhesive materials |
US20080086888A1 (en) * | 2006-10-11 | 2008-04-17 | Noah Scheinfeld | Razor blades comprising a layer including releasable bioactive agent |
US8133553B2 (en) * | 2007-06-18 | 2012-03-13 | Zimmer, Inc. | Process for forming a ceramic layer |
US8309521B2 (en) | 2007-06-19 | 2012-11-13 | Zimmer, Inc. | Spacer with a coating thereon for use with an implant device |
GB0715514D0 (en) * | 2007-08-10 | 2007-09-19 | Tissuemed Ltd | Coated medical devices |
US8608049B2 (en) * | 2007-10-10 | 2013-12-17 | Zimmer, Inc. | Method for bonding a tantalum structure to a cobalt-alloy substrate |
US20110230973A1 (en) * | 2007-10-10 | 2011-09-22 | Zimmer, Inc. | Method for bonding a tantalum structure to a cobalt-alloy substrate |
US20090110738A1 (en) * | 2007-10-26 | 2009-04-30 | Celonova Biosciences, Inc. | Loadable Polymeric Particles for Cosmetic and Reconstructive Tissue Augmentation Applications and Methods of Preparing and Using the Same |
US20090111763A1 (en) * | 2007-10-26 | 2009-04-30 | Celonova Biosciences, Inc. | Loadable polymeric particles for bone augmentation and methods of preparing and using the same |
US20090110730A1 (en) * | 2007-10-30 | 2009-04-30 | Celonova Biosciences, Inc. | Loadable Polymeric Particles for Marking or Masking Individuals and Methods of Preparing and Using the Same |
US20090110731A1 (en) * | 2007-10-30 | 2009-04-30 | Celonova Biosciences, Inc. | Loadable Polymeric Microparticles for Therapeutic Use in Alopecia and Methods of Preparing and Using the Same |
US20090181068A1 (en) | 2008-01-14 | 2009-07-16 | Dunn Richard L | Low Viscosity Liquid Polymeric Delivery System |
US20090187256A1 (en) * | 2008-01-21 | 2009-07-23 | Zimmer, Inc. | Method for forming an integral porous region in a cast implant |
US20090198286A1 (en) * | 2008-02-05 | 2009-08-06 | Zimmer, Inc. | Bone fracture fixation system |
CN103570884B (en) * | 2013-11-14 | 2015-06-17 | 湖南科技大学 | Preparation method for maleic anhydride-modified polylactic-co-glycolic acid |
CN109836563B (en) * | 2017-11-29 | 2021-02-19 | 北京旭阳科技有限公司 | Preparation method of unsaturated polyester resin containing glycerol monomethyl ether unit |
Family Cites Families (76)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB630924A (en) | 1946-05-04 | 1949-10-24 | Bakelite Corp | Alkyd resins |
US2895930A (en) * | 1955-06-28 | 1959-07-21 | Bradley & Vrooman Company | Water emulsion of polymerizable epoxide group containing oil modified alkyd and formaldehyde condensation resins |
US3278464A (en) * | 1961-12-08 | 1966-10-11 | Hooker Chemical Corp | Phosphonated polymers |
DE1694845A1 (en) | 1967-02-25 | 1971-08-05 | Ruetgerswerke Ag | Polyester molding compounds |
US3806479A (en) * | 1972-06-14 | 1974-04-23 | Sherwin Williams Co | Ester-containing liquid polyols |
US3997512A (en) * | 1973-11-21 | 1976-12-14 | American Cyanamid Company | High molecular weight polyester resin, the method of making the same |
US3978203A (en) * | 1974-07-12 | 1976-08-31 | Dynatech Corporation | Sustained release of pharmaceuticals from polyester matrices |
US4076798A (en) * | 1975-05-29 | 1978-02-28 | American Cyanamid Company | High molecular weight polyester resin, the method of making the same and the use thereof as a pharmaceutical composition |
US4095600A (en) * | 1976-06-01 | 1978-06-20 | American Cyanamid Company | Normally-solid, bioabsorbable, hydrolyzable, polymeric reaction product |
US4048256A (en) * | 1976-06-01 | 1977-09-13 | American Cyanamid Company | Normally-solid, bioabsorbable, hydrolyzable, polymeric reaction product |
US4122129A (en) * | 1976-06-01 | 1978-10-24 | American Cyanamid Company | Normally-solid, bioabsorbable, hydrolyzable, polymeric reaction product |
US4118470A (en) * | 1976-06-01 | 1978-10-03 | American Cyanamid Company | Normally-solid, bioabsorbable, hydrolyzable, polymeric reaction product |
US4163073A (en) * | 1977-07-05 | 1979-07-31 | Union Carbide Corporation | Process for treating inorganic siliceous surfaces |
US4384975A (en) * | 1980-06-13 | 1983-05-24 | Sandoz, Inc. | Process for preparation of microspheres |
DE3041073C2 (en) * | 1980-10-31 | 1986-01-02 | Dynamit Nobel Ag, 5210 Troisdorf | Wool wax substitutes |
US4419139A (en) * | 1982-03-24 | 1983-12-06 | University Of Southern Mississippi | Process for preparing coating binders from vegetable oil material |
US4568559A (en) * | 1984-02-06 | 1986-02-04 | Biotek, Inc. | Composite core coated microparticles and process of preparing same |
US5902741A (en) | 1986-04-18 | 1999-05-11 | Advanced Tissue Sciences, Inc. | Three-dimensional cartilage cultures |
CA1340581C (en) | 1986-11-20 | 1999-06-08 | Joseph P. Vacanti | Chimeric neomorphogenesis of organs by controlled cellular implantation using artificial matrices |
US5306311A (en) * | 1987-07-20 | 1994-04-26 | Regen Corporation | Prosthetic articular cartilage |
DE3808638A1 (en) | 1988-03-15 | 1989-09-28 | Siemens Ag | DEVICE FOR INSTALLING AN OPTICAL CHARACTER GENERATOR IN A PRINTER HOUSING |
DE3825211A1 (en) * | 1988-07-25 | 1990-02-01 | Henkel Kgaa | IMPROVED BODY RESORBONABLE WAXES (III) |
ATE119787T1 (en) | 1989-04-25 | 1995-04-15 | Childrens Medical Center | IMPLANTS FOR LARGE QUANTITIES OF CELLS ON POLYMERIC MATRICES. |
US5137743A (en) * | 1990-09-07 | 1992-08-11 | Opta Food Ingredients, Inc. | Foods having an oil phase thickened with an oil soluble polyester |
DK13491D0 (en) | 1991-01-25 | 1991-01-25 | Novo Nordisk As | APPLICATION OF AN ENZYMOUS GRANULATE AND PROCEDURE FOR PREPARING A TABLET FORM |
SE9100610D0 (en) * | 1991-03-04 | 1991-03-04 | Procordia Ortech Ab | BIORESORBABLE MATERIAL FOR MEDICAL USE |
US5879920A (en) | 1991-10-07 | 1999-03-09 | Genencor International, Inc. | Coated enzyme-containing granule |
JPH05194189A (en) | 1991-10-23 | 1993-08-03 | Boehringer Ingelheim Kg | Semisolid mixture of oligomer and/or polymer based on lactic acid, method for production thereof and use thereof as absorptive insert |
WO1993008850A1 (en) | 1991-10-30 | 1993-05-13 | Massachusetts Institute Of Technology | Prevascularized polymeric implants for organ transplantation |
US5219980A (en) * | 1992-04-16 | 1993-06-15 | Sri International | Polymers biodegradable or bioerodiable into amino acids |
SK277092A3 (en) * | 1992-09-07 | 1996-08-07 | Galena As | Medicaments with n-methylated cyclic undecapeptides |
US5525848A (en) * | 1992-09-25 | 1996-06-11 | Magnetic Bearing Technologies, Inc. | Magnetic bearing system including a generator |
DE4243904A1 (en) | 1992-12-23 | 1994-06-30 | Roth Technik Gmbh | catalyst |
JPH06211651A (en) | 1993-01-12 | 1994-08-02 | Hisamitsu Pharmaceut Co Inc | Composition for treating nail trichophytosis |
WO1994025079A1 (en) | 1993-04-23 | 1994-11-10 | Massachusetts Institute Of Technology | Porous biodegradable polymeric materials for cell transplantation |
JP3220331B2 (en) * | 1993-07-20 | 2001-10-22 | エチコン・インコーポレーテツド | Absorbable liquid copolymers for parenteral administration |
US5411554A (en) * | 1993-07-20 | 1995-05-02 | Ethicon, Inc. | Liquid polymer filled envelopes for use as surgical implants |
US5442033A (en) * | 1993-07-20 | 1995-08-15 | Ethicon, Inc. | Liquid copolymers of epsilon-caprolactone and lactide |
US5359026A (en) | 1993-07-30 | 1994-10-25 | Cargill, Incorporated | Poly(lactide) copolymer and process for manufacture thereof |
TW282403B (en) * | 1993-08-26 | 1996-08-01 | Takeda Pharm Industry Co Ltd | |
US6149953A (en) | 1993-11-08 | 2000-11-21 | Delta Food Group, Inc. | Seeded microcapsules |
US5599852A (en) * | 1994-10-18 | 1997-02-04 | Ethicon, Inc. | Injectable microdispersions for soft tissue repair and augmentation |
AU706434B2 (en) | 1994-10-18 | 1999-06-17 | Ethicon Inc. | Injectable liquid copolymers for soft tissue repair and augmentation |
US6335383B1 (en) | 1994-10-18 | 2002-01-01 | Ethicon, Inc. | Microdispersions for coating surgical devices |
US5962023A (en) | 1995-03-06 | 1999-10-05 | Ethicon, Inc. | Hydrogels containing absorbable polyoxaamides |
US6147168A (en) | 1995-03-06 | 2000-11-14 | Ethicon, Inc. | Copolymers of absorbable polyoxaesters |
US5859150A (en) * | 1995-03-06 | 1999-01-12 | Ethicon, Inc. | Prepolymers of absorbable polyoxaesters |
US5618552A (en) * | 1995-03-06 | 1997-04-08 | Ethicon, Inc. | Absorbable polyoxaesters |
US5700583A (en) | 1995-03-06 | 1997-12-23 | Ethicon, Inc. | Hydrogels of absorbable polyoxaesters containing amines or amido groups |
US5607687A (en) * | 1995-03-06 | 1997-03-04 | Ethicon, Inc. | Polymer blends containing absorbable polyoxaesters |
US5464929A (en) * | 1995-03-06 | 1995-11-07 | Ethicon, Inc. | Absorbable polyoxaesters |
US6100346A (en) | 1995-03-06 | 2000-08-08 | Ethicon, Inc. | Copolymers of polyoxaamides |
US5698213A (en) * | 1995-03-06 | 1997-12-16 | Ethicon, Inc. | Hydrogels of absorbable polyoxaesters |
KR100201352B1 (en) | 1995-03-16 | 1999-06-15 | 성재갑 | Single shot vaccine formulation |
US5641502A (en) | 1995-06-07 | 1997-06-24 | United States Surgical Corporation | Biodegradable moldable surgical material |
GB9602638D0 (en) | 1995-09-07 | 1996-04-10 | Croda Int Plc | Triglyceride drying oil derivatives |
SE505146C2 (en) | 1995-10-19 | 1997-06-30 | Biogram Ab | Particles for delayed release |
US5698993A (en) * | 1996-03-28 | 1997-12-16 | Industrial Technology Research Institute | CMOS level shifting circuit |
CA2256900A1 (en) | 1996-05-29 | 1997-12-04 | Xiao-Ying Meng | Cationic polymer/lipid nucleic acid delivery vehicles |
US6121398A (en) | 1997-10-27 | 2000-09-19 | University Of Delaware | High modulus polymers and composites from plant oils |
IL136681A0 (en) | 1997-12-12 | 2001-06-14 | Samyang Corp | Biodegradable mixed polymeric micelles for gene delivery |
US6074660A (en) * | 1998-04-20 | 2000-06-13 | Ethicon, Inc. | Absorbable polyoxaesters containing amines and/ or amido groups |
US6268329B1 (en) | 1998-06-30 | 2001-07-31 | Nouozymes A/S | Enzyme containing granule |
BR9912070A (en) | 1998-07-13 | 2001-04-10 | Expression Genetics Inc | Poly-l-lysine polyester analog as a soluble, biodegradable gene delivery vehicle |
US6114458A (en) | 1998-09-23 | 2000-09-05 | International Business Machines Corporation | Highly branched radial block copolymers |
WO2000035511A1 (en) | 1998-12-17 | 2000-06-22 | Cambridge Scientific, Inc. | Sequenced incorporation of cortical bone allografts |
ATE514729T1 (en) | 1999-02-01 | 2011-07-15 | Eidgenoess Tech Hochschule | BIOMATERIALS ADDED BY NUCLEOPHILIC REACTION ON CONJUGATE UNSATURATED GROUPS |
IL131074A0 (en) | 1999-07-23 | 2001-03-19 | Polygene Ltd | A biodegradable polycation composition for delivery of an anionic macromolecule |
SE520688C2 (en) | 2000-04-11 | 2003-08-12 | Bone Support Ab | An injectable bone mineral replacement material |
FR2810236B1 (en) | 2000-06-15 | 2002-07-26 | Oreal | FILM-FORMING COSMETIC COMPOSITION |
US7030127B2 (en) | 2001-06-29 | 2006-04-18 | Ethicon, Inc. | Composition and medical devices utilizing bioabsorbable polymeric waxes |
US7326426B2 (en) | 2002-03-29 | 2008-02-05 | Ethicon, Inc. | Compositions and medical devices utilizing bioabsorbable liquid polymers |
US7005136B2 (en) * | 2002-03-29 | 2006-02-28 | Ethicon, Inc. | Bone replacement materials utilizing bioabsorbable liquid polymers |
US7368125B2 (en) | 2002-06-05 | 2008-05-06 | Ethicon, Inc. | Amphiphilic polymers for medical applications |
US7026374B2 (en) * | 2002-06-25 | 2006-04-11 | Aruna Nathan | Injectable microdispersions for medical applications |
US7101566B2 (en) | 2002-06-28 | 2006-09-05 | Ethicon, Inc. | Polymer coated microparticles for sustained release |
-
2002
- 2002-12-18 US US10/322,154 patent/US6872799B2/en not_active Expired - Lifetime
-
2003
- 2003-12-09 AU AU2003266800A patent/AU2003266800B2/en not_active Ceased
- 2003-12-12 CA CA2452951A patent/CA2452951C/en not_active Expired - Fee Related
- 2003-12-16 KR KR1020030091974A patent/KR100995482B1/en not_active IP Right Cessation
- 2003-12-17 DE DE60322824T patent/DE60322824D1/en not_active Expired - Lifetime
- 2003-12-17 EP EP03257961A patent/EP1431327B1/en not_active Expired - Lifetime
- 2003-12-17 AT AT03257961T patent/ATE404605T1/en not_active IP Right Cessation
- 2003-12-17 TW TW092135676A patent/TWI334874B/en not_active IP Right Cessation
- 2003-12-18 CN CNA2003101246782A patent/CN1513887A/en active Pending
-
2004
- 2004-10-11 US US10/962,274 patent/US7253248B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
TWI334874B (en) | 2010-12-21 |
ATE404605T1 (en) | 2008-08-15 |
US7253248B2 (en) | 2007-08-07 |
AU2003266800B2 (en) | 2009-02-19 |
EP1431327B1 (en) | 2008-08-13 |
AU2003266800A1 (en) | 2004-07-08 |
CN1513887A (en) | 2004-07-21 |
CA2452951C (en) | 2012-02-07 |
US20050085605A1 (en) | 2005-04-21 |
KR100995482B1 (en) | 2010-11-22 |
TW200418900A (en) | 2004-10-01 |
EP1431327A1 (en) | 2004-06-23 |
DE60322824D1 (en) | 2008-09-25 |
US6872799B2 (en) | 2005-03-29 |
KR20040054516A (en) | 2004-06-25 |
US20040120927A1 (en) | 2004-06-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2452951A1 (en) | Functionalized polymers for medical applications | |
CA2453892A1 (en) | Alkyd-lactone copolymers for medical applications | |
CA2431241A1 (en) | Amphiphilic polymers for medical applications | |
CA2453779A1 (en) | Cationic alkyd polyesters for medical applications | |
CA2391898A1 (en) | Compositions and medical devices utilizing bioabsorbable polymeric waxes | |
CA2423999A1 (en) | Compositions and medical devices utilizing bioabsorbable liquid polymers | |
US7012106B2 (en) | Reinforced implantable medical devices | |
CA1280256C (en) | Caprolactone polymer for suture coating | |
CA2433679A1 (en) | Polymer coated microparticles for sustained release | |
US5468252A (en) | Packaged synthetic absorbable surgical elements | |
CA2433244A1 (en) | Injectable microdispersions for medical applications | |
AU771403B2 (en) | Flexible wound covering based on fibrin and process for its production | |
JP6147760B2 (en) | Bioabsorbable hemostatic products using polyethylene glycol binder | |
CA2006714C (en) | Absorbable coating and blend | |
RU2574016C2 (en) | Reinforced resorbable synthetic matrix for haemostatic applications | |
US6260699B1 (en) | Packaged synthetic absorbable surgical elements | |
US7572298B2 (en) | Implantable medical devices and methods for making same | |
US5728135A (en) | Stiffened suture for use in a suturing device | |
JP4906723B2 (en) | Surgical prosthesis with biodegradable and non-biodegradable regions | |
US5462162A (en) | Packaged synthetic absorbable surgical elements | |
US20110152927A1 (en) | Knotless suture device | |
EP0399827A3 (en) | Modified polyester composition and preparation process and use thereof | |
US5366081A (en) | Packaged synthetic absorbable surgical elements | |
JP2009067732A (en) | Gelatin hydrogel membrane for periodontal surgical treatment | |
Nuutinen et al. | Mechanical properties and in vitro degradation of self-reinforced radiopaque bioresorbable polylactide fibres |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20141212 |