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 PDF

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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
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.)
Ceased
Application number
PCT/US1999/007912
Other languages
English (en)
French (fr)
Other versions
WO1999052469A9 (en
Inventor
Susan J. Peter
Laura J. Suggs
Paul S. Engel
Antonios G. Mikos
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.)
William Marsh Rice University
Original Assignee
William Marsh Rice University
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.)
Filing date
Publication date
Application filed by William Marsh Rice University filed Critical William Marsh Rice University
Priority to JP2000543082A priority Critical patent/JP2002539275A/ja
Priority to CA002327730A priority patent/CA2327730A1/en
Priority to EP99915349A priority patent/EP1079869B1/en
Priority to DE69924369T priority patent/DE69924369D1/de
Priority to AT99915349T priority patent/ATE291444T1/de
Publication of WO1999052469A1 publication Critical patent/WO1999052469A1/en
Publication of WO1999052469A9 publication Critical patent/WO1999052469A9/en
Priority to US09/678,816 priority patent/US6355755B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Surgery (AREA)
  • Medicinal Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Composite Materials (AREA)
  • Dermatology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Materials For Medical Uses (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
PCT/US1999/007912 1998-04-10 1999-04-09 Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger Ceased WO1999052469A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
JP2000543082A JP2002539275A (ja) 1998-04-10 1999-04-09 プロトンスカベンジャの存在下でのプロピレングリコールのアシル化によるポリ（プロピレンフマラート）の合成
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
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 (de) 1998-04-10 1999-04-09 Synthese von poly(propylenfumarat)durch azetylierung von propylenglykol in anwesenheit eines protonenfängers
AT99915349T ATE291444T1 (de) 1998-04-10 1999-04-09 Synthese von poly(propylenfumarat)durch azetylierung von propylenglykol in anwesenheit eines protonenfängers
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
US60/081,308 1998-04-10
US60/081,405 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 Ceased 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 (https=)
EP (1) EP1079869B1 (https=)
JP (1) JP2002539275A (https=)
AT (1) ATE291444T1 (https=)
CA (1) CA2327730A1 (https=)
DE (1) DE69924369D1 (https=)
WO (1) WO1999052469A1 (https=)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005521440A (ja) * 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 骨再生のための、生体再吸収可能な骨伝導性組成物
EP1282428A4 (en) * 2000-05-11 2007-09-05 Univ Wm Marsh Rice BIOCOMPATIBLE MACROMERS
WO2009094370A1 (en) * 2008-01-23 2009-07-30 Tate And Lyle Ingredients Americas, Inc. Fumaric acid/diol polyesters and their manufacture and use

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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
WO1999052469A1 (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
JP2002542349A (ja) * 1999-04-16 2002-12-10 ダブリューエム・マーシュ・ライス・ユニバーシティー ポリ（プロピレンフマラート）−ジアクリレートマクロマーで交差結合された生体分解性のポリ（プロピレンフマラート）ネットワーク
DE10032220A1 (de) 2000-07-03 2002-01-24 Sanatis Gmbh Magnesium-ammonium-phosphat-Zemente, deren Herstellung und Verwendung
US6849223B2 (en) * 2001-04-19 2005-02-01 Case Western Reserve University Fabrication of a polymeric prosthetic implant
DE60226242T2 (de) * 2001-06-28 2009-05-28 William Marsh Rice University, Houston Photoquervernetzung von biologischen materialien aus fumarsäurediethylester/poly(propylenfumarat)
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
US20070065652A1 (en) * 2003-03-13 2007-03-22 Willaim Marsh Rice University Composite injectable and pre-fabricated bone replacement material and method for the production of such bone replacement material
AU2003214708A1 (en) 2003-03-14 2004-09-30 Roque Humberto Ferreyro Irigoyen 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
US20070043202A1 (en) * 2003-07-01 2007-02-22 Yaszemski Michael J Self-crosslinkable poly(caprolactone fumarate)
US7252686B2 (en) * 2003-08-13 2007-08-07 Boston Scientific Scimed Methods for reducing bone compression fractures using wedges
WO2005030034A2 (en) 2003-09-26 2005-04-07 Depuy Spine, Inc. Device for delivering viscous material
US20060018949A1 (en) * 2004-04-07 2006-01-26 Bausch & Lomb Incorporated Injectable biodegradable drug delivery system
KR20060134223A (ko) 2004-04-27 2006-12-27 키폰 인크. 뼈 대체 조성물 및 사용 방법
WO2006053031A2 (en) * 2004-11-12 2006-05-18 Mayo Foundation For Medical Education And Research Photocrosslinkable poly(caprolactone fumarate)
JP4897699B2 (ja) * 2004-11-18 2012-03-14 メイヨ フオンデーシヨン フオー メデイカル エジユケーシヨン アンド リサーチ ポリカプロラクトンとポリ（プロピレンフマレート）とのブロックコポリマー
ATE511439T1 (de) * 2005-04-29 2011-06-15 Mayo Foundation Hydrophile/hydrophobe polymernetze auf der basis von poly(caprolactonfumarat), poly(ethylenglycolfumarat) und copolymere davon
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
CA2663447A1 (en) 2006-09-14 2008-03-20 Depuy Spine, Inc. Polymeric bone cement and methods of use thereof
ES2389784T3 (es) * 2006-09-21 2012-10-31 Kyphon SÀRL Fosfato de diamonio y otras sales de amonio y su uso para prevenir la coagulación de la sangre
CA2665995C (en) * 2006-10-19 2011-11-29 Oren Globerman Fluid delivery system
US20080195223A1 (en) * 2006-11-03 2008-08-14 Avram Allan Eddin Materials and Methods and Systems for Delivering Localized Medical Treatments
ATE551967T1 (de) * 2007-07-30 2012-04-15 Purzer Pharmaceutical Co Ltd Biologisch abbaubarer knochenzement und herstellungsverfahren dafür
US7968616B2 (en) * 2008-04-22 2011-06-28 Kyphon Sarl Bone cement composition and method
EP2590605A1 (en) 2010-07-09 2013-05-15 Board of Regents of the University of Texas System Biodegradable scaffolds
EP2605805B1 (en) 2010-08-20 2019-01-09 Case Western Reserve University Continuous digital light processing additive manufacturing of implants
US11865785B2 (en) * 2010-08-20 2024-01-09 H. David Dean Continuous digital light processing additive manufacturing of implants
EP3139962B1 (en) 2014-05-05 2020-12-23 Advanced Medical Solutions Israel (Sealantis) Ltd Biological adhesives and sealants and methods of using the same
BR112017010057B1 (pt) * 2014-11-18 2022-11-29 The Ohio State University Método para produzir um polímero de polipropileno fumarato para uso em impressão 3d
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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Publication number Priority date Publication date Assignee Title
EP1282428A4 (en) * 2000-05-11 2007-09-05 Univ Wm Marsh Rice BIOCOMPATIBLE MACROMERS
JP2005521440A (ja) * 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 骨再生のための、生体再吸収可能な骨伝導性組成物
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
US6355755B1 (en) 2002-03-12
WO1999052469A9 (en) 2000-03-23
EP1079869B1 (en) 2005-03-23
JP2002539275A (ja) 2002-11-19
CA2327730A1 (en) 1999-10-21
ATE291444T1 (de) 2005-04-15
EP1079869A1 (en) 2001-03-07
DE69924369D1 (de) 2005-04-28
US6124373A (en) 2000-09-26
EP1079869A4 (en) 2002-08-07

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