CA2285909A1 - Biodegradable polymers chain-extended by phosphates, compositions, articles and methods for making and using the same - Google Patents

Biodegradable polymers chain-extended by phosphates, compositions, articles and methods for making and using the same Download PDF

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Publication number
CA2285909A1
CA2285909A1 CA002285909A CA2285909A CA2285909A1 CA 2285909 A1 CA2285909 A1 CA 2285909A1 CA 002285909 A CA002285909 A CA 002285909A CA 2285909 A CA2285909 A CA 2285909A CA 2285909 A1 CA2285909 A1 CA 2285909A1
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CA
Canada
Prior art keywords
polymers
compositions
methods
branched
alkyl
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
CA002285909A
Other languages
French (fr)
Other versions
CA2285909C (en
Inventor
Hai-Quan Mao
Zhong Zhao
James P. English
Kam W. Leong
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.)
Eisai Inc
School of Medicine of Johns Hopkins University
Original Assignee
Guilford Pharmaceuticals Inc.
Hai-Quan Mao
Zhong Zhao
James P. English
Kam W. Leong
Johns Hopkins University School Of Medicine
Mgi Gp, Inc.
Eisai Corporation Of North America
Eisai Inc.
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 Guilford Pharmaceuticals Inc., Hai-Quan Mao, Zhong Zhao, James P. English, Kam W. Leong, Johns Hopkins University School Of Medicine, Mgi Gp, Inc., Eisai Corporation Of North America, Eisai Inc. filed Critical Guilford Pharmaceuticals Inc.
Publication of CA2285909A1 publication Critical patent/CA2285909A1/en
Application granted granted Critical
Publication of CA2285909C publication Critical patent/CA2285909C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
    • A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
    • 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
    • A61L17/06—At least partially resorbable materials
    • A61L17/10—At least partially resorbable materials containing macromolecular materials
    • A61L17/12—Homopolymers or copolymers of glycolic acid or lactic acid
    • 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
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0019—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form 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
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
    • C08G63/6922—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from hydroxy carboxylic acids
    • 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
    • C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
    • C08L85/02—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers containing phosphorus
    • 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
    • Y10S623/00—Prosthesis, i.e. artificial body members, parts thereof, or aids and accessories therefor
    • Y10S623/924—Material characteristic

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Materials Engineering (AREA)
  • Surgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Neurosurgery (AREA)
  • Vascular Medicine (AREA)
  • Biomedical Technology (AREA)
  • Transplantation (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Medicinal Preparation (AREA)
  • Biological Depolymerization Polymers (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Materials For Medical Uses (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polyamides (AREA)

Abstract

Biodegradable polymers are described comprising the recurring monomeric units shown in formula (I) or (II) wherein X is -O- or -NR'-, where R' is H or alkyl; L is a branched or straight chain aliphatic group having from 1-20 carbon atoms; M1 and M2 are each independently (1) a branched or straight chain aliphatic group having from 1-20 carbon atoms; or (2) a branched or straight chain, oxy-, carboxy- or amino-aliphatic group having from 1-20 carbon atoms; Y is -O-, -S-or -NR'-, where R' is H or alkyl; R is H, alkyl, alkoxy, aryl, aryloxy, heterocyclic or heterocycloxy; the molar ratio of x:y is about 1; the molar ratio n:(x or y) is between about 200:1 and 1:200; and the molar ratio q:r is between about 1:99 and 99:1; wherein said biodegradable polymer is biocompatible before and upon biodegradation. Processes for preparing the polymers, compositions containing the polymers and biologically active substances, articles useful for implantation or injection into the body fabricated from the compositions, and methods for controllably releasing biologically active substances using the polymers, are also described.
CA002285909A 1997-04-03 1998-04-02 Biodegradable polymers chain-extended by phosphates, compositions, articles and methods for making and using the same Expired - Fee Related CA2285909C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US83221797A 1997-04-03 1997-04-03
US08/832,217 1997-04-03
PCT/US1998/006380 WO1998044020A1 (en) 1997-04-03 1998-04-02 Biodegradable polymers chain-extended by phosphates, compositions, articles and methods for making and using the same

Publications (2)

Publication Number Publication Date
CA2285909A1 true CA2285909A1 (en) 1998-10-08
CA2285909C CA2285909C (en) 2008-07-29

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA002285909A Expired - Fee Related CA2285909C (en) 1997-04-03 1998-04-02 Biodegradable polymers chain-extended by phosphates, compositions, articles and methods for making and using the same

Country Status (18)

Country Link
US (3) US6166173A (en)
EP (1) EP0971969B1 (en)
JP (1) JP4170399B2 (en)
KR (1) KR20010006041A (en)
CN (1) CN1107687C (en)
AT (1) ATE271084T1 (en)
AU (1) AU742110B2 (en)
BR (1) BR9809390A (en)
CA (1) CA2285909C (en)
DE (1) DE69825040T2 (en)
HK (1) HK1027366A1 (en)
HU (1) HUP0001412A2 (en)
IL (1) IL132122A0 (en)
NO (1) NO994803L (en)
NZ (1) NZ500674A (en)
RU (1) RU2207350C2 (en)
UA (1) UA54505C2 (en)
WO (1) WO1998044020A1 (en)

Families Citing this family (72)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6495579B1 (en) 1996-12-02 2002-12-17 Angiotech Pharmaceuticals, Inc. Method for treating multiple sclerosis
US6713527B2 (en) 1997-02-07 2004-03-30 Queen's University At Kingston Anaesthetic bone cement
US6355705B1 (en) * 1997-02-07 2002-03-12 Queen's University At Kingston Anaesthetic bone cement
UA54505C2 (en) * 1997-04-03 2003-03-17 Гілфорд Фармасьютікалз Інк. Biodegradable polymers, bound by phosphates, compositions, products and pocesses for manufacturing and using thereof
WO1998048859A1 (en) * 1997-04-30 1998-11-05 Guilford Pharmaceuticals Inc. Biodegradable compositions comprising poly(cycloaliphatic phosphoester) compounds, articles, and methods for using the same
CA2335460A1 (en) 1998-06-18 1999-12-23 Johns Hopkins University School Of Medicine Polymers for delivery of nucleic acids
US6419709B1 (en) 1998-10-02 2002-07-16 Guilford Pharmaceuticals, Inc. Biodegradable terephthalate polyester-poly(Phosphite) compositions, articles, and methods of using the same
US6350464B1 (en) * 1999-01-11 2002-02-26 Guilford Pharmaceuticals, Inc. Methods for treating ovarian cancer, poly (phosphoester) compositions, and biodegradable articles for same
US6348042B1 (en) * 1999-02-02 2002-02-19 W. Lee Warren, Jr. Bioactive shunt
US6537585B1 (en) 1999-03-26 2003-03-25 Guilford Pharmaceuticals, Inc. Methods and compositions for treating solid tumors
US6461631B1 (en) 1999-11-16 2002-10-08 Atrix Laboratories, Inc. Biodegradable polymer composition
AU2001247346A1 (en) * 2000-03-10 2001-09-24 Johns Hopkins University Phosphate based biodegradable polymers
WO2002004544A2 (en) * 2000-07-06 2002-01-17 Guilford Pharmaceuticals Polymers and polymerization processes
AU2001270310A1 (en) * 2000-07-07 2002-01-21 Guilford Pharmaceuticals Inc. Compositions for sustained release of antineoplastic taxanes, and methods of making and using the same
WO2002005800A2 (en) * 2000-07-17 2002-01-24 Guilford Pharmaceuticals, Inc. Compositions for sustained release of analgesic agents, and methods of making and using the same
US7666445B2 (en) * 2000-10-20 2010-02-23 The Trustees Of The University Of Pennsylvania Polymer-based surgically implantable haloperidol delivery systems and methods for their production and use
US20020141966A1 (en) * 2000-11-16 2002-10-03 Wenbin Dang Compositions for treatment of malignant effusions, and methods of making and using the same
US6527693B2 (en) 2001-01-30 2003-03-04 Implant Sciences Corporation Methods and implants for providing radiation to a patient
US6590059B2 (en) 2001-05-11 2003-07-08 Ap Pharma, Inc. Bioerodible polyorthoesters from dioxolane-based diketene acetals
US7345138B2 (en) * 2001-05-14 2008-03-18 Johns Hopkins Singapore Pte Ltd. Biodegradable polyphosphates for controlled release of bioactive substances
WO2003000776A1 (en) * 2001-05-14 2003-01-03 Johns Hopkins Singapore Pte Ltd Biodegradable polyphosphoramidates for controlled release of bioactive substances
US20030133903A1 (en) * 2001-07-19 2003-07-17 Wenbin Dang Compositions for treatment of prostate cancers and methods of making and using the same
WO2003007915A2 (en) * 2001-07-19 2003-01-30 Guilford Pharmaceuticals, Inc. Compositions for treatment of head and neck cancers, and methods of making and using the same
AUPR951501A0 (en) * 2001-12-14 2002-01-24 Smart Drug Systems Inc Modified sustained release pharmaceutical system
AU2003202255A1 (en) * 2002-01-09 2003-07-30 Guilford Pharmaceuticals, Inc. Compositions for treatment of central nervous system neoplasms, and methods of making and using the same
AU2003216424A1 (en) * 2002-02-25 2003-10-08 Guilford Pharmaceuticals, Inc. Phosphorus-containing compounds with polymeric chains, and methods of making and using the same
FR2839260B1 (en) * 2002-05-03 2005-02-25 Inst Nat Sante Rech Med MICROPARTICLES BASED ON BICOMPATIBLE AND BIODEGRADABLE MATERIAL SUPPORTING CELLS AND BIOLOGICALLY ACTIVE SUBSTANCES
US20050129776A1 (en) 2002-05-03 2005-06-16 Inserm Microparticles supporting cells and active substances
US20090004741A1 (en) * 2002-05-14 2009-01-01 Jun Wang Biodegradable polyphosphoramidates for controlled release of bioactive substances
US8313760B2 (en) 2002-05-24 2012-11-20 Angiotech International Ag Compositions and methods for coating medical implants
PT1509256E (en) 2002-05-24 2009-10-15 Angiotech Int Ag Compositions and methods for coating medical implants
US7041309B2 (en) * 2002-06-13 2006-05-09 Neuropro Technologies, Inc. Spinal fusion using an HMG-CoA reductase inhibitor
SE0202619D0 (en) * 2002-09-05 2002-09-05 Fredrik Nederberg New Polymers and Applications
US20040197301A1 (en) * 2003-02-18 2004-10-07 Zhong Zhao Hybrid polymers and methods of making the same
US20050209664A1 (en) * 2003-11-20 2005-09-22 Angiotech International Ag Electrical devices and anti-scarring agents
CA2536188A1 (en) * 2003-11-20 2005-06-09 Angiotech International Ag Electrical devices and anti-scarring agents
JP5306599B2 (en) * 2004-01-12 2013-10-02 ザ トラスティーズ オブ ザ ユニバーシティ オブ ペンシルバニア Long-term delivery formulation
US8221778B2 (en) 2005-01-12 2012-07-17 The Trustees Of The University Of Pennsylvania Drug-containing implants and methods of use thereof
US8329203B2 (en) * 2004-01-12 2012-12-11 The Trustees Of The University Of Pennsylvania Drug-containing implants and methods of use thereof
US8119153B2 (en) * 2004-08-26 2012-02-21 Boston Scientific Scimed, Inc. Stents with drug eluting coatings
DE602005012551D1 (en) * 2004-12-22 2009-03-12 California Inst Of Techn DEVELOPABLE POLYMERS AND MANUFACTURING METHOD THEREFOR
US7237497B2 (en) * 2005-01-13 2007-07-03 Card-Monroe Corp. Replaceable hook modules
EP1838305A1 (en) * 2005-01-21 2007-10-03 Richard H. Matthews Radiosensitizer formulations comprising nitrohistidine derivatives
AU2005100176A4 (en) * 2005-03-01 2005-04-07 Gym Tv Pty Ltd Garbage bin clip
US7669732B2 (en) * 2005-10-25 2010-03-02 Imi Cornelius Inc. Cup lid dispenser
EP1808380A1 (en) * 2006-01-13 2007-07-18 Pepup S.A. Flexible pouch for a liquid and method of manufacturing thereof
US7846361B2 (en) 2006-07-20 2010-12-07 Orbusneich Medical, Inc. Bioabsorbable polymeric composition for a medical device
US20090169628A1 (en) 2006-10-17 2009-07-02 Armark Authentication Technologies, Llc Article and method for focused delivery of therapeutic and/or diagnostic materials
US7959942B2 (en) 2006-10-20 2011-06-14 Orbusneich Medical, Inc. Bioabsorbable medical device with coating
CN101631513B (en) 2006-10-20 2013-06-05 奥巴斯尼茨医学公司 Bioabsorbable polymeric composition and medical device
JP2008138051A (en) * 2006-11-30 2008-06-19 Terumo Corp alpha-HYDROXY ACID POLYMER COMPOSITION AND METHOD FOR PRODUCING MOLDED ARTICLE BY USING THE SAME
WO2008098220A1 (en) * 2007-02-08 2008-08-14 University Of Washington Biocompatile amino acid anhydride polymers
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
CN101125916B (en) * 2007-06-26 2010-06-23 天大药业（珠海）有限公司 Biodegradation polymer and its preparing process and application
US8608049B2 (en) 2007-10-10 2013-12-17 Zimmer, Inc. Method for bonding a tantalum structure to a cobalt-alloy substrate
JP2009096720A (en) * 2007-10-12 2009-05-07 Idemitsu Kosan Co Ltd Biodegradable liquid ester compound
CA2708514A1 (en) * 2007-12-31 2009-07-16 Armark Authentication Technologies, Llc Article and method for focused delivery of therapeutic and/or diagnostic materials
WO2009143236A1 (en) * 2008-05-20 2009-11-26 Albert Einstein Healthcare Network Compositions and methods for the treatment of skeletal metastatic lesions and fractures
WO2010010685A1 (en) * 2008-07-24 2010-01-28 東洋紡績株式会社 Aliphatic polyester resin and production method thereof
WO2010037021A2 (en) * 2008-09-29 2010-04-01 Armark Authentication Technologies, Llc Spinneret and method of spinning fiber
US20100291214A1 (en) * 2008-12-23 2010-11-18 Armark Authentication Technologies, Llc Three-dimensional microfiber extrudate structure and process for forming three-dimensional microfiber extrudate structure
US9414864B2 (en) 2009-04-15 2016-08-16 Warsaw Orthopedic, Inc. Anterior spinal plate with preformed drug-eluting device affixed thereto
US9078712B2 (en) 2009-04-15 2015-07-14 Warsaw Orthopedic, Inc. Preformed drug-eluting device to be affixed to an anterior spinal plate
US20100291384A1 (en) * 2009-05-15 2010-11-18 Armark Authentication Technologies, Llc Fiber having non-uniform composition and method for making same
US9636109B2 (en) * 2009-07-22 2017-05-02 Wisconsin Alumni Research Foundation Biologically active sutures for regenerative medicine
EP2542187B1 (en) * 2010-03-03 2019-11-20 Novabone Products, LLC Composition for the regeneration of bony defects
US9144629B2 (en) 2010-03-03 2015-09-29 Novabone Products, Llc Ionically crosslinked materials and methods for production
WO2015147923A1 (en) 2010-03-03 2015-10-01 Novabone Products, Llc Kit for delivering bone grafting materials
CN103371857A (en) * 2012-04-12 2013-10-30 北京汇福康医疗技术有限公司 Composite biological cannula and preparation method and application thereof
US8907050B2 (en) * 2012-05-11 2014-12-09 University Of South Carolina Polymeric additive for strength, deformability, and toughness enhancement of cemetitious materials and composites
US10066204B2 (en) 2013-03-15 2018-09-04 Wisconsin Alumni Research Foundation Chemically labile peptide-presenting surfaces for cellular self-assembly

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442982A (en) * 1965-10-15 1969-05-06 Weston Chemical Corp Polyphosphites of 2,2-dimethyl-3-hydroxypropyl - 2 - dimethyl - 3-hydroxypropionate
US4746462A (en) * 1985-02-21 1988-05-24 Dainichiseika Color & Chemicals Mfg. Co., Ltd. Phosphoric ester compound
US5256765A (en) * 1989-03-09 1993-10-26 The Johns Hopkins University School Of Medicine Biodegradable poly(phosphate esters)
US5194581A (en) * 1989-03-09 1993-03-16 Leong Kam W Biodegradable poly(phosphoesters)
DE4404365A1 (en) * 1994-02-11 1995-08-17 Cassella Ag Polycondensates containing phosphine and phosphonic acid groups
CA2250981C (en) 1996-04-23 2002-07-02 Kinerton Limited Acidic polylactic polymers
UA54505C2 (en) * 1997-04-03 2003-03-17 Гілфорд Фармасьютікалз Інк. Biodegradable polymers, bound by phosphates, compositions, products and pocesses for manufacturing and using thereof
JP2002515939A (en) 1997-06-18 2002-05-28 ギルフォード ファーマシュウティカルズ インコーポレイテッド Two-step solution polymerization of high molecular weight polyphosphoester
US6028163A (en) 1997-06-27 2000-02-22 Guilford Pharmaceuticals Inc. Solution polymerization of high molecular weight poly(phosphoesters) in toluene

Also Published As

Publication number Publication date
JP2001521561A (en) 2001-11-06
NZ500674A (en) 2002-02-01
WO1998044020A1 (en) 1998-10-08
CN1256701A (en) 2000-06-14
NO994803L (en) 1999-12-03
RU2207350C2 (en) 2003-06-27
HUP0001412A2 (en) 2000-08-28
BR9809390A (en) 2000-06-13
AU6944998A (en) 1998-10-22
IL132122A0 (en) 2001-03-19
ATE271084T1 (en) 2004-07-15
JP4170399B2 (en) 2008-10-22
US20020151617A1 (en) 2002-10-17
UA54505C2 (en) 2003-03-17
EP0971969B1 (en) 2004-07-14
CN1107687C (en) 2003-05-07
HK1027366A1 (en) 2001-01-12
CA2285909C (en) 2008-07-29
DE69825040T2 (en) 2005-09-08
EP0971969A1 (en) 2000-01-19
DE69825040D1 (en) 2004-08-19
AU742110B2 (en) 2001-12-20
US6166173A (en) 2000-12-26
KR20010006041A (en) 2001-01-15
NO994803D0 (en) 1999-10-01
US6376644B1 (en) 2002-04-23

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