WO1999052469A1 - Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger - Google Patents
Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger Download PDFInfo
- Publication number
- WO1999052469A1 WO1999052469A1 PCT/US1999/007912 US9907912W WO9952469A1 WO 1999052469 A1 WO1999052469 A1 WO 1999052469A1 US 9907912 W US9907912 W US 9907912W WO 9952469 A1 WO9952469 A1 WO 9952469A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fumarate
- poly
- molecular weight
- polydispersity index
- average molecular
- Prior art date
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
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/56—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds other than from esters thereof
-
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/0047—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
- A61L24/0073—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix
- A61L24/0084—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material with a macromolecular matrix containing fillers of phosphorus-containing inorganic compounds, e.g. apatite
-
- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing 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
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
Definitions
- BACKGROUND OF THE INVENTION It is often desired to replace or reconstruct all or a portion of a living bone, such as when a bone has been broken or has been resected as a result of a bone tumor.
- the missing bone can be replaced with a mechanical device, such as a pin, plate or the like, or it can be replaced with an implant that is designed to more closely resemble the original bone itself.
- these implants comprise biodegradable compounds or parts made from such compounds.
- porous, biodegradable compounds that contain or are coated with an osteogenic substance. It is contemplated that bone tissue will grow back into the pores of the implant and will gradually replace the entire implant as the implant itself is gradually degraded in the in vivo environment.
- bone implants are typically formed from a substance that is initially malleable and then becomes hard after a reasonably short period of time. Because living bone tends to atrophy and degrade in the absence of compressive stress, however, it is important that the implant not become too hard. An implant whose compressive strength is too great (i.e. an implant that is too hard) will cause stress shielding of the surrounding bone. Stress shielding in turn causes the surrounding bone to weaken and may ultimately result in catastrophic failure. Hence, the suitability of a given substance for implantation as a bone replacement depends on its biocompatibility, set time, biodegradability and ultimate compressive strength. Certain polymers have been found to be suitable in this regard.
- the P(PF) can be incorporated into a paste, along with a monomer capable of addition polymerization an inorganic filler such as beta- tricalcium phosphate, sodium chloride or hydroxyapatite, a radical initiator such as benzoyl peroxide, azobisisobutyronitrile, or acetyl peroxide, and an accelerator such as N,N dimethyl toluidine.
- a monomer capable of addition polymerization an inorganic filler such as beta- tricalcium phosphate, sodium chloride or hydroxyapatite, a radical initiator such as benzoyl peroxide, azobisisobutyronitrile, or acetyl peroxide, and an accelerator such as N,N dimethyl toluidine.
- suitable monomer include vinyl pyrrolidone, acrylic acid, methyl methacrylate, styrene, methacrylic acid, or 2-hydroxy ethyl methacrylate, and copolymers thereof.
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99915349A EP1079869B1 (en) | 1998-04-10 | 1999-04-09 | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
DE69924369T DE69924369D1 (en) | 1998-04-10 | 1999-04-09 | SYNTHESIS OF POLY (PROPYLENE FUMARATE) BY ACETYLATION OF PROPYLENE GLYCOL IN THE PRESENCE OF A PROTONATE FENDER |
CA002327730A CA2327730A1 (en) | 1998-04-10 | 1999-04-09 | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
JP2000543082A JP2002539275A (en) | 1998-04-10 | 1999-04-09 | Synthesis of poly (propylene fumarate) by acylation of propylene glycol in the presence of proton scavenger |
AT99915349T ATE291444T1 (en) | 1998-04-10 | 1999-04-09 | SYNTHESIS OF POLY(PROPYLENE NFUMARATE) BY ACETYLATION OF PROPYLENE GLYCOL IN THE PRESENCE OF A PROTON CAPTURER |
US09/678,816 US6355755B1 (en) | 1998-04-10 | 2000-10-04 | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8130898P | 1998-04-10 | 1998-04-10 | |
US8140598P | 1998-04-10 | 1998-04-10 | |
US60/081,405 | 1998-04-10 | ||
US60/081,308 | 1998-04-10 | ||
US8218298P | 1998-04-16 | 1998-04-16 | |
US60/082,182 | 1998-04-16 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/678,816 Continuation US6355755B1 (en) | 1998-04-10 | 2000-10-04 | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1999052469A1 true WO1999052469A1 (en) | 1999-10-21 |
WO1999052469A9 WO1999052469A9 (en) | 2000-03-23 |
Family
ID=27373944
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/007912 WO1999052469A1 (en) | 1998-04-10 | 1999-04-09 | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
Country Status (7)
Country | Link |
---|---|
US (2) | US6124373A (en) |
EP (1) | EP1079869B1 (en) |
JP (1) | JP2002539275A (en) |
AT (1) | ATE291444T1 (en) |
CA (1) | CA2327730A1 (en) |
DE (1) | DE69924369D1 (en) |
WO (1) | WO1999052469A1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1282428A1 (en) * | 2000-05-11 | 2003-02-12 | Wm. MARSH RICE UNIVERSITY | Biocompatible macromers |
JP2005521440A (en) * | 2002-02-05 | 2005-07-21 | ケンブリッジ サイエンティフィック, インコーポレイテッド | Bioresorbable osteoconductive composition for bone regeneration |
WO2009094370A1 (en) * | 2008-01-23 | 2009-07-30 | Tate And Lyle Ingredients Americas, Inc. | Fumaric acid/diol polyesters and their manufacture and use |
Families Citing this family (43)
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US6486232B1 (en) * | 1997-04-18 | 2002-11-26 | Cambridge Scientific, Inc. | Bioerodible polymeric semi-interpenetrating network alloys for internal fixation devices and bone cements |
CA2327730A1 (en) | 1998-04-10 | 1999-10-21 | Wm Marsh Rice University | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
DE60026983T2 (en) | 1999-04-16 | 2007-01-25 | William Marsh Rice University, Houston | FUNCTIONALIZED POLYPROPYLENE FUMARATE AND POLYPROPYLENE FUMARATE COETHYLENE GLYCOL |
DE10032220A1 (en) | 2000-07-03 | 2002-01-24 | Sanatis Gmbh | Magnesium ammonium phosphate cements, their manufacture and use |
WO2002085246A2 (en) * | 2001-04-19 | 2002-10-31 | Case Western Reserve University | Fabrication of a polymeric prosthetic implant |
CA2451203A1 (en) * | 2001-06-28 | 2003-01-09 | Wm. Marsh Rice University | Photocrosslinking of diethyl fumarate/poly(propylene fumarate) biomaterials |
US7629388B2 (en) | 2001-11-20 | 2009-12-08 | William Marsh Rice University | Synthesis and characterization of biodegradable cationic poly(propylene fumarate-co-ethylene glycol) copolymer hydrogels modified with agmatine for enhanced cell adhesion |
US6884432B2 (en) * | 2002-04-25 | 2005-04-26 | Mayo Foundation For Medical Education And Research | Blend, cross-linkable poly(propylene fumarate) for immobilization and controlled drug delivery |
US7273523B2 (en) | 2002-06-07 | 2007-09-25 | Kyphon Inc. | Strontium-apatite-cement-preparations, cements formed therefrom, and uses thereof |
WO2004082524A2 (en) * | 2003-03-13 | 2004-09-30 | William Marsh Rice University | Composite injectable and pre-fabricated bone replacement material and method for the production of such bone replacement material |
EP1614403B2 (en) | 2003-03-14 | 2014-06-18 | Depuy Spine, Inc. | Hydraulic device for the injection of bone cement in percutaneous vertebroplasty |
US8066713B2 (en) | 2003-03-31 | 2011-11-29 | Depuy Spine, Inc. | Remotely-activated vertebroplasty injection device |
US8415407B2 (en) | 2004-03-21 | 2013-04-09 | Depuy Spine, Inc. | Methods, materials, and apparatus for treating bone and other tissue |
WO2006011152A2 (en) * | 2004-06-17 | 2006-02-02 | Disc-O-Tech Medical Technologies, Ltd. | Methods for treating bone and other tissue |
CA2528150A1 (en) * | 2003-07-01 | 2005-01-20 | Mayo Foundation For Medical Education And Research | Self-crosslinkable poly(caprolactone fumarate) |
US7252686B2 (en) * | 2003-08-13 | 2007-08-07 | Boston Scientific Scimed | Methods for reducing bone compression fractures using wedges |
US8579908B2 (en) | 2003-09-26 | 2013-11-12 | DePuy Synthes Products, LLC. | Device for delivering viscous material |
US20060018949A1 (en) * | 2004-04-07 | 2006-01-26 | Bausch & Lomb Incorporated | Injectable biodegradable drug delivery system |
MXPA06012420A (en) | 2004-04-27 | 2007-03-28 | Kyphon Inc | Bone substitute compositions and method of use. |
CA2587308A1 (en) * | 2004-11-12 | 2006-05-18 | Mayo Foundation For Medical Education And Research | Photocrosslinkable poly(caprolactone fumarate) |
EP1812481B1 (en) * | 2004-11-18 | 2012-01-11 | Mayo Foundation for Medical Education and Research | Block copolymers of polycaprolactone and poly (propylene fumarate) |
WO2006118987A1 (en) * | 2005-04-29 | 2006-11-09 | Mayo Foundation For Medical Education And Research | Hydrophilic/hydrophobic polymer networks based on poly(caprolactone fumarate), poly(ethylene glycol fumarate), and copolymers thereof |
US9381024B2 (en) | 2005-07-31 | 2016-07-05 | DePuy Synthes Products, Inc. | Marked tools |
US9918767B2 (en) | 2005-08-01 | 2018-03-20 | DePuy Synthes Products, Inc. | Temperature control system |
US7651701B2 (en) * | 2005-08-29 | 2010-01-26 | Sanatis Gmbh | Bone cement composition and method of making the same |
US8360629B2 (en) | 2005-11-22 | 2013-01-29 | Depuy Spine, Inc. | Mixing apparatus having central and planetary mixing elements |
US7754005B2 (en) * | 2006-05-02 | 2010-07-13 | Kyphon Sarl | Bone cement compositions comprising an indicator agent and related methods thereof |
US7507286B2 (en) * | 2006-06-08 | 2009-03-24 | Sanatis Gmbh | Self-foaming cement for void filling and/or delivery systems |
WO2008001385A2 (en) * | 2006-06-29 | 2008-01-03 | Depuy Spine, Inc. | Integrated bone biopsy and therapy apparatus |
CN101516412B (en) | 2006-09-14 | 2014-02-12 | 德普伊斯派尔公司 | Bone cement and use method thereof |
WO2008039382A2 (en) * | 2006-09-21 | 2008-04-03 | Kyphon Sarl | Diammonium phosphate and other ammonium salts and their use in preventing clotting |
AU2007311451A1 (en) * | 2006-10-19 | 2008-04-24 | Depuy Spine, Inc. | Fluid delivery system |
WO2008073190A2 (en) * | 2006-11-03 | 2008-06-19 | Kyphon Sarl | Materials and methods and systems for delivering localized medical treatments |
PT2022446E (en) * | 2007-07-30 | 2012-07-04 | Purzer Pharmaceutical Co Ltd | Bio-degenerable bone cement and manufacturing method thereof |
US7968616B2 (en) * | 2008-04-22 | 2011-06-28 | Kyphon Sarl | Bone cement composition and method |
US20130184835A1 (en) | 2010-07-09 | 2013-07-18 | Board Of Regents Of The Unversity Of Texas System | Biodegradable scaffolds |
US11865785B2 (en) * | 2010-08-20 | 2024-01-09 | H. David Dean | Continuous digital light processing additive manufacturing of implants |
EP3511027A1 (en) | 2010-08-20 | 2019-07-17 | Case Western Reserve University | Continuous digital light processing additive manufacturing of implants |
ES2864658T3 (en) | 2014-05-05 | 2021-10-14 | Advanced Medical Solutions Israel Sealantis Ltd | Biological adhesives and sealants and methods of using them |
WO2016081587A1 (en) * | 2014-11-18 | 2016-05-26 | The University Of Akron | Well-defined degradable poly(propylene fumarate) polymers and scalable methods for the synthesis thereof |
US11499008B2 (en) | 2017-02-02 | 2022-11-15 | University Of Akron | Functionalized poly (propylene fumarate) polymers made by ring opening polymerization using magnesium catalysts |
GB2594243A (en) * | 2020-04-15 | 2021-10-27 | Arterius Ltd | A bone cement |
WO2022015989A1 (en) * | 2020-07-15 | 2022-01-20 | The University Of Akron | Synthesis of poly (propylene maleate-co-succinate) by the time-dependent reduction of poly (propylene maleate) double bonds mediated by zinc and acetic acid |
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US3538043A (en) * | 1967-06-02 | 1970-11-03 | Gen Tire & Rubber Co | Polymeric esters and methods |
US4722948A (en) * | 1984-03-16 | 1988-02-02 | Dynatech Corporation | Bone replacement and repair putty material from unsaturated polyester resin and vinyl pyrrolidone |
US5527864A (en) * | 1995-08-08 | 1996-06-18 | Suggs; Laura J. | Poly(propylene fumarate-co-ethylene oxide) |
US5733951A (en) * | 1994-04-28 | 1998-03-31 | Yaszemski; Michael J. | Poly(propylene fumarate) |
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CA2327730A1 (en) | 1998-04-10 | 1999-10-21 | Wm Marsh Rice University | Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger |
-
1999
- 1999-04-09 CA CA002327730A patent/CA2327730A1/en not_active Abandoned
- 1999-04-09 US US09/289,361 patent/US6124373A/en not_active Expired - Lifetime
- 1999-04-09 DE DE69924369T patent/DE69924369D1/en not_active Expired - Fee Related
- 1999-04-09 WO PCT/US1999/007912 patent/WO1999052469A1/en active IP Right Grant
- 1999-04-09 EP EP99915349A patent/EP1079869B1/en not_active Expired - Lifetime
- 1999-04-09 JP JP2000543082A patent/JP2002539275A/en active Pending
- 1999-04-09 AT AT99915349T patent/ATE291444T1/en not_active IP Right Cessation
-
2000
- 2000-10-04 US US09/678,816 patent/US6355755B1/en not_active Expired - Lifetime
Patent Citations (4)
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US3538043A (en) * | 1967-06-02 | 1970-11-03 | Gen Tire & Rubber Co | Polymeric esters and methods |
US4722948A (en) * | 1984-03-16 | 1988-02-02 | Dynatech Corporation | Bone replacement and repair putty material from unsaturated polyester resin and vinyl pyrrolidone |
US5733951A (en) * | 1994-04-28 | 1998-03-31 | Yaszemski; Michael J. | Poly(propylene fumarate) |
US5527864A (en) * | 1995-08-08 | 1996-06-18 | Suggs; Laura J. | Poly(propylene fumarate-co-ethylene oxide) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1282428A1 (en) * | 2000-05-11 | 2003-02-12 | Wm. MARSH RICE UNIVERSITY | Biocompatible macromers |
EP1282428A4 (en) * | 2000-05-11 | 2007-09-05 | Univ Wm Marsh Rice | Biocompatible macromers |
JP2005521440A (en) * | 2002-02-05 | 2005-07-21 | ケンブリッジ サイエンティフィック, インコーポレイテッド | Bioresorbable osteoconductive composition for bone regeneration |
WO2009094370A1 (en) * | 2008-01-23 | 2009-07-30 | Tate And Lyle Ingredients Americas, Inc. | Fumaric acid/diol polyesters and their manufacture and use |
Also Published As
Publication number | Publication date |
---|---|
EP1079869A1 (en) | 2001-03-07 |
WO1999052469A9 (en) | 2000-03-23 |
CA2327730A1 (en) | 1999-10-21 |
ATE291444T1 (en) | 2005-04-15 |
DE69924369D1 (en) | 2005-04-28 |
JP2002539275A (en) | 2002-11-19 |
US6124373A (en) | 2000-09-26 |
US6355755B1 (en) | 2002-03-12 |
EP1079869A4 (en) | 2002-08-07 |
EP1079869B1 (en) | 2005-03-23 |
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