WO1999024391A1 - Radio-opaque polymer biomaterials - Google Patents

Radio-opaque polymer biomaterials Download PDF

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Publication number
WO1999024391A1
WO1999024391A1 PCT/US1998/023777 US9823777W WO9924391A1 WO 1999024391 A1 WO1999024391 A1 WO 1999024391A1 US 9823777 W US9823777 W US 9823777W WO 9924391 A1 WO9924391 A1 WO 9924391A1
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WO
WIPO (PCT)
Prior art keywords
polymer
radio
opaque
group
drug delivery
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/US1998/023777
Other languages
English (en)
French (fr)
Other versions
WO1999024391B1 (en
Inventor
Joachim B. Kohn
Durgadas Bolikal
Sanyog M. Pendharkar
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.)
Rutgers State University of New Jersey
Original Assignee
Rutgers State University of New Jersey
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 Rutgers State University of New Jersey filed Critical Rutgers State University of New Jersey
Priority to CA002308721A priority Critical patent/CA2308721C/en
Priority to AT98959390T priority patent/ATE307110T1/de
Priority to JP2000520405A priority patent/JP4465105B2/ja
Priority to AU15199/99A priority patent/AU737151B2/en
Priority to EP98959390A priority patent/EP1036057B1/en
Priority to US09/554,027 priority patent/US6475477B1/en
Priority to DE69831973T priority patent/DE69831973T2/de
Publication of WO1999024391A1 publication Critical patent/WO1999024391A1/en
Publication of WO1999024391B1 publication Critical patent/WO1999024391B1/en
Anticipated expiration legal-status Critical
Priority to US10/691,750 priority patent/US7056493B2/en
Priority to US11/024,355 priority patent/US7250154B2/en
Priority to US11/418,943 priority patent/US20060204440A1/en
Priority to US11/933,780 priority patent/US20080107709A1/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
    • C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/04—X-ray contrast preparations
    • A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
    • A61K49/0438—Organic X-ray contrast-enhancing agent comprising an iodinated group or an iodine atom, e.g. iopamidol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/04—X-ray contrast preparations
    • A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
    • A61K49/0442—Polymeric X-ray contrast-enhancing agent comprising a halogenated group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/04—X-ray contrast preparations
    • A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
    • A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
    • 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
    • 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
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • 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
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/18—Materials at least partially X-ray or laser opaque
    • 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
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/672—Dicarboxylic acids and dihydroxy compounds
    • 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
    • C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
    • C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6826—Dicarboxylic acids and dihydroxy compounds
    • 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
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6856—Dicarboxylic acids and dihydroxy compounds
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
    • C08G64/10—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing halogens
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
    • C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/1633—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing halogens
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
    • C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/1641—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
    • 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
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/18—Block or graft polymers
    • C08G64/183—Block or graft polymers containing polyether sequences
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
    • C08G65/3314—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic
    • C08G65/3315—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic
    • C08G65/3317—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic phenolic
    • 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44—Polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
    • A61K9/204—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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices

Definitions

  • m kl 3 Z 4 +0.2 wherein m is the absorption coefficient, 1 is the wavelength of the incident X-ray, Z is the atomic number of the absorbing species and k is the proportionality constant.
  • Iodine and bromine atoms because of their high mass, scatter X-rays and impart radio-opaqueness. This is highly significant and allows clinicians to visualize any implanted device prepared from a radio-opaque polymer by simple X-ray imaging.
  • the polymer contains only iodine or bromine-substituted monomeric repeating units. If g is any fraction greater than 0 but smaller than 1, a copolymer is obtained that contains a defined ratio of monomeric repeating units substituted with bromine or iodine and monomeric repeating units that are bromine- and iodine-free.
  • the poly(alkylene oxide) segments decrease the surface adhesion of the polymers of the present invention. As the value of f in Formulae VIII and VTIIa increases, the surface adhesion decreases.
  • Polymer coating containing poly(alkylene oxide) segments according to the present invention may thus be prepared that are resistant to cell attachment and useful non-thrombogenic coatings on surfaces in contact with blood. Such polymers also resist bacterial adhesion in this, and in other medical applications as well.
  • the present invention therefore includes blood contacting devices and medical implants having surfaces coated with the polymers of Formulae VIII and Villa in which f is greater than 0.
  • the surfaces are preferably polymeric surfaces.
  • Methods according to the present invention include implanting in the body of the patient a blood-contacting device or medical implant having a surface coated with the above- described polymers of the present invention containing poly(alkylene oxide) segments.
  • GPC gel permeation chromatography
  • the polymer-drug combinations may be used alone or in combination with other therapeutic or diagnostic agents.
  • the compounds of this invention can be utilized in vivo, ordinarily in mammals such as primates such as humans, sheep, horses, cattle, pigs, dogs, cats, rats and mice, or in vitro.
  • a 100 mL round bottomed flask equipped with an overhead stirrer was purged with nitrogen for one hour, and then charged with 4.349 g (9.0 mmoles) of DiTE, 1.315 g (9.0 mmoles) of adipic acid, 1.06 of dimethylaminopyridinium p-toluene sulfonate (2.5 mmoles), and 68 mL of methylene chloride.
  • the mixture was stirred for five minutes, then 4.2 mL (27 mmoles) of DIPC were added in one portion.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials For Medical Uses (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Medicinal Preparation (AREA)
  • Polyethers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Polyamides (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
PCT/US1998/023777 1997-11-07 1998-11-06 Radio-opaque polymer biomaterials Ceased WO1999024391A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
CA002308721A CA2308721C (en) 1997-11-07 1998-11-06 Radio-opaque polymer biomaterials
AT98959390T ATE307110T1 (de) 1997-11-07 1998-11-06 Strahlungsdurchlässiges polymeres biomaterial
JP2000520405A JP4465105B2 (ja) 1997-11-07 1998-11-06 放射線不透過性ポリマー生体適合材料
AU15199/99A AU737151B2 (en) 1997-11-07 1998-11-06 Radio-opaque polymeric biomaterials government license rights
EP98959390A EP1036057B1 (en) 1997-11-07 1998-11-06 Radio-opaque polymer biomaterials
US09/554,027 US6475477B1 (en) 1997-11-07 1998-11-06 Radio-opaque polymer biomaterials
DE69831973T DE69831973T2 (de) 1997-11-07 1998-11-06 Strahlungsdurchlässiges polymeres biomaterial
US10/691,750 US7056493B2 (en) 1997-11-07 2003-10-23 Radio-opaque polymer biomaterials
US11/024,355 US7250154B2 (en) 1997-11-07 2004-12-28 Radio-opaque polymeric biomaterials
US11/418,943 US20060204440A1 (en) 1997-11-07 2006-05-05 Radio-opaque polymeric biomaterials
US11/933,780 US20080107709A1 (en) 1997-11-07 2007-11-01 Radio-opaque polymeric biomaterials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6490597P 1997-11-07 1997-11-07
US60/064,905 1997-11-07

Related Child Applications (3)

Application Number Title Priority Date Filing Date
US09/554,027 A-371-Of-International US6475477B1 (en) 1997-11-07 1998-11-06 Radio-opaque polymer biomaterials
US09554027 A-371-Of-International 1998-11-06
US10/288,076 Division US6852308B2 (en) 1997-11-07 2002-11-05 Radio-opaque polymeric biomaterials

Publications (2)

Publication Number Publication Date
WO1999024391A1 true WO1999024391A1 (en) 1999-05-20
WO1999024391B1 WO1999024391B1 (en) 1999-07-15

Family

ID=22059024

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/US1998/023777 Ceased WO1999024391A1 (en) 1997-11-07 1998-11-06 Radio-opaque polymer biomaterials
PCT/US1998/023737 Ceased WO1999024490A1 (en) 1997-11-07 1998-11-06 Strictly alternating poly(alkylene oxide ether) copolymers

Family Applications After (1)

Application Number Title Priority Date Filing Date
PCT/US1998/023737 Ceased WO1999024490A1 (en) 1997-11-07 1998-11-06 Strictly alternating poly(alkylene oxide ether) copolymers

Country Status (9)

Country Link
US (9) US6475477B1 (enExample)
EP (3) EP1036057B1 (enExample)
JP (3) JP2001522909A (enExample)
AT (3) ATE307110T1 (enExample)
AU (2) AU740380B2 (enExample)
CA (3) CA2579619C (enExample)
DE (3) DE69825619T2 (enExample)
ES (1) ES2226191T3 (enExample)
WO (2) WO1999024391A1 (enExample)

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000071182A1 (en) * 1999-05-20 2000-11-30 Scimed Life Systems, Inc. Radiopaque compositions
WO2006014596A1 (en) * 2004-07-08 2006-02-09 Reva Medical, Inc. Side-chain crystallizable polymers for medical applications
WO2006020616A1 (en) * 2004-08-13 2006-02-23 Reva Medical, Inc. Inherently radiopaque bioresorbable polymers for multiple uses
EP1830902A2 (en) * 2004-12-30 2007-09-12 Cinvention Ag Combination comprising an agent providing a signal, an implant material and a drug
WO2007114823A1 (en) * 2006-04-06 2007-10-11 Reva Medical, Inc. Embolic prosthesis for treatment of vascular aneurysm
WO2007084444A3 (en) * 2006-01-18 2008-07-17 Reva Medical Inc Side-chain crystallizable polymers for medical applications
WO2008100346A3 (en) * 2006-10-17 2008-11-13 Reva Medical Inc N-substituted monomers and polymers
EP1673109A4 (en) * 2003-09-25 2008-12-24 Univ Rutgers INHERENT RADIATOR-FREE POLYMER PRODUCTS FOR EMBOLOTHERAPY
EP1923075A3 (en) * 2004-08-13 2009-07-01 Rutgers, The State University Radiopaque polymeric stents
EP1955716A3 (en) * 2004-08-13 2009-10-07 Rutgers, The State University Radiopaque polymeric stents
WO2009081169A3 (en) * 2007-12-21 2009-12-10 Iopharma Technologies Ab Biodegradable contrast agents
US8044108B2 (en) 2006-04-07 2011-10-25 The University Of Queensland Porous polymer blend structures
US8222308B2 (en) 2006-04-07 2012-07-17 The University Of Queensland Porous polymer structures
US8722037B2 (en) 2004-03-19 2014-05-13 Meck Sharp & Dohme B.V. X-ray visible drug delivery device
EP2459638A4 (en) * 2009-07-31 2016-06-08 Univ Rutgers MONOMERS AND PHASE SEPARATED BIO-COMPATIBLE POLYMER COMPOSITIONS PREPARED FOR USE IN MEDICINE
US9605112B2 (en) 2009-10-11 2017-03-28 Rutgers, The State University Of New Jersey Biocompatible polymers for medical devices
US9636402B2 (en) 2000-11-16 2017-05-02 Microspherix Llc Flexible and/or elastic brachytherapy seed or strand
US10087285B2 (en) 2014-12-23 2018-10-02 Rutgers, The State University Of New Jersey Biocompatible iodinated diphenol monomers and polymers
WO2020033521A1 (en) * 2018-08-08 2020-02-13 Reva Medical, Inc. Cross-linked radiopaque bioresorbable polymers and devices made therefrom
US10774030B2 (en) 2014-12-23 2020-09-15 Rutgers, The State University Of New Jersey Polymeric biomaterials derived from phenolic monomers and their medical uses
US11124603B2 (en) 2012-02-03 2021-09-21 Rutgers, The State University Of New Jersey Polymeric biomaterials derived from phenolic monomers and their medical uses
US11472918B2 (en) 2012-02-03 2022-10-18 Rutgers, The State University Of New Jersey Polymeric biomaterials derived from phenolic monomers and their medical uses
US11608486B2 (en) 2015-07-02 2023-03-21 Terumo Bct, Inc. Cell growth with mechanical stimuli
US11613727B2 (en) 2010-10-08 2023-03-28 Terumo Bct, Inc. Configurable methods and systems of growing and harvesting cells in a hollow fiber bioreactor system
US11624046B2 (en) 2017-03-31 2023-04-11 Terumo Bct, Inc. Cell expansion
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