WO2012071441A3 - Biodegradable stealth polymeric particles fabricated using the macromonomer approach by free radical dispersion polymerization - Google Patents

Biodegradable stealth polymeric particles fabricated using the macromonomer approach by free radical dispersion polymerization Download PDF

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Publication number
WO2012071441A3
WO2012071441A3 PCT/US2011/061902 US2011061902W WO2012071441A3 WO 2012071441 A3 WO2012071441 A3 WO 2012071441A3 US 2011061902 W US2011061902 W US 2011061902W WO 2012071441 A3 WO2012071441 A3 WO 2012071441A3
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WIPO (PCT)
Prior art keywords
crosslinked
polymer particle
dispersion polymerization
present
free radical
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Ceased
Application number
PCT/US2011/061902
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French (fr)
Other versions
WO2012071441A2 (en
Inventor
Emmanuel Oyekanmi Akala
Simeon Kolawole Adesina
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Howard University
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Howard University
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Application filed by Howard University filed Critical Howard University
Priority to EP11842970.3A priority Critical patent/EP2643382A4/en
Priority to CA2818869A priority patent/CA2818869C/en
Publication of WO2012071441A2 publication Critical patent/WO2012071441A2/en
Publication of WO2012071441A3 publication Critical patent/WO2012071441A3/en
Anticipated expiration legal-status Critical
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
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/78—Preparation processes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
    • 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
    • A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/513—Organic macromolecular compounds; Dendrimers
    • A61K9/5146—Organic macromolecular compounds; Dendrimers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyamines, polyanhydrides
    • A61K9/5153—Polyesters, e.g. poly(lactide-co-glycolide)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B01J13/16—Interfacial polymerisation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y15/00—Nanotechnology for interacting, sensing or actuating, e.g. quantum dots as markers in protein assays or molecular motors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
    • C08F299/024—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
    • 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
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic 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
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • 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
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
    • 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
    • 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
    • Y10S977/00—Nanotechnology
    • Y10S977/70—Nanostructure
    • Y10S977/773—Nanoparticle, i.e. structure having three dimensions of 100 nm or less
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nanotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Polymers & Plastics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Biophysics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

The present invention is directed to a crosslinked or non-crosslinked polymer particle, wherein the crosslinked polymer particle comprises a copolymer of poly(alklyene glycol-graft-lactate) that is crosslinked by at least one hydrolysable monmer. Another embodiment of the present invention is a polymer particle comprising a crosslinked polymer particle that is a product of starting materials comprising (a) a hydrophilic monomer, (b) a hydrophobic monomer, and (c) a hydrolysable crosslinking agent. Another embodiment of the present invention is a polymer particle comprising, a crosslinked copolymer comprises structures represented by Formulas (I), (II), and (III), where Formulas (I), (II) and (III) are defined in the specification. Yet other embodiments of the present invention include a method of preparing a methacrylate terminated macromonomer, a method of preparing a crosslinking agent, and a method of preparing a therapeutic agent loaded nanosphere by dispersion polymerization.
PCT/US2011/061902 2010-11-23 2011-11-22 Biodegradable stealth polymeric particles fabricated using the macromonomer approach by free radical dispersion polymerization Ceased WO2012071441A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP11842970.3A EP2643382A4 (en) 2010-11-23 2011-11-22 Biodegradable stealth polymeric particles fabricated using the macromonomer approach by free radical dispersion polymerization
CA2818869A CA2818869C (en) 2010-11-23 2011-11-22 Biodegradable stealth polymeric particles fabricated using the macromonomer approach by free radical dispersion polymerization

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12/952,843 US8921429B2 (en) 2010-11-23 2010-11-23 Biodegradable stealth polymeric particles fabricated using the macromonomer approach by free radical dispersion polymerization
US12/952,843 2010-11-23

Publications (2)

Publication Number Publication Date
WO2012071441A2 WO2012071441A2 (en) 2012-05-31
WO2012071441A3 true WO2012071441A3 (en) 2013-01-10

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US (3) US8921429B2 (en)
EP (1) EP2643382A4 (en)
CA (1) CA2818869C (en)
WO (1) WO2012071441A2 (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014205000A1 (en) * 2013-06-17 2014-12-24 University Of North Carolina At Chapel Hill Polymer coated particles and methods thereof
US10618998B2 (en) * 2014-11-12 2020-04-14 Purdue Research Foundation Poly(alkylene carbonate)-based amphiphilic block copolymers and methods of use thereof
CN104877669B (en) * 2015-04-14 2018-07-17 温州生物材料与工程研究所 The micro-nano system of composite fluorescence and its preparation process based on one pot synthesis
US11826344B2 (en) * 2015-11-19 2023-11-28 Howard University Composition, method of manufacture, and use of site-specific delivery of bruceolides for treatment of cancer and other diseases
WO2018067617A1 (en) * 2016-10-03 2018-04-12 The Penn State Research Foundation Compounds comprising conductive oligomers, materials formed therefrom, and methods of making and using same
AU2018214596A1 (en) * 2017-02-02 2019-08-08 The University Of Akron Functionalized poly(propylene fumarate) polymers made by ring opening polymerization using magnesium catalysts
CN110218286A (en) * 2017-06-01 2019-09-10 长兴化学工业(中国)有限公司 Acrylate-polyurethane copolymer resins and conductive silver paste containing the resin
CN107915834B (en) * 2017-11-30 2020-11-20 沈阳金博地生态环保科技有限公司 Polylactic acid modified material and preparation method thereof
CN108096247B (en) * 2017-12-29 2019-12-31 成都恒瑞制药有限公司 Preparation method of rosiglitazone inclusion compound
WO2019227319A1 (en) * 2018-05-29 2019-12-05 南通纺织丝绸产业技术研究院 Fluorine-containing polycaprolactone film and preparation method therefor
CN108676156B (en) * 2018-06-25 2021-02-02 河南师范大学 Reduction response type ABC type block polymer and preparation method and application thereof
CN109438682B (en) * 2018-11-16 2022-04-26 中国科学院宁波材料技术与工程研究所 Copolyester, preparation method and product thereof
US11986557B2 (en) * 2018-11-28 2024-05-21 Howard University Stealth nanoparticles
US12383246B2 (en) 2020-10-12 2025-08-12 Abbott Cardiovascular Systems, Inc. Vessel closure device with improved safety and tract hemostasis
KR102571040B1 (en) * 2021-03-22 2023-08-29 주식회사 도이프 Composition inducing bone regeneration of implant placement and manufacturing method thereof
CN114133595B (en) * 2021-12-06 2023-06-02 广东华美众源生物科技有限公司 Preparation method of pH-temperature dual-sensitive nano hydrogel
CN115887702B (en) * 2022-11-22 2024-11-15 共价键(南京)科技有限公司 Specific gall bladder delivery nano fluorescent probe, preparation method and application thereof
WO2025074120A1 (en) * 2023-10-06 2025-04-10 Imperial College Innovations Limited Nanoparticles for extended release drug delivery
EP4647472A1 (en) * 2024-05-08 2025-11-12 Canon Production Printing Holding B.V. Radiation-curable component, ink composition, printing method and printed object
CN120988297B (en) * 2025-08-13 2026-04-10 滨州医学院 Multifunctional multi-hetero-arm star polymer and preparation method and application thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5130479A (en) * 1989-12-20 1992-07-14 Ceskoslovenska Akademie Ved Hydrolytically degradable hydrophilic gels and the method for preparation thereof using n,o-dimethacryloylhydroxylamine as a cross-linking agent
US20020064513A1 (en) * 2000-09-18 2002-05-30 Amarnath Maitra Sustained release and long residing ophthalmic formulation and the process of preparing the same
US20030018128A1 (en) * 2000-12-29 2003-01-23 Wang James H. Grafted biodegradable polymer blend compositions

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4346183A (en) 1981-04-03 1982-08-24 E. I. Du Pont De Nemours And Company Methacrylate polymer mix containing alkaline earth metal resinate
US6828025B2 (en) 2002-05-24 2004-12-07 Mcmaster University Microencapsulation of polar liquids in copolymer shells
US7758880B2 (en) 2002-12-11 2010-07-20 Advanced Cardiovascular Systems, Inc. Biocompatible polyacrylate compositions for medical applications
EP1663469A4 (en) 2003-09-05 2009-01-07 Univ Massachusetts CAPSULES OF AMPHIPHILEM POLYMER AND ASSOCIATED METHODS FOR LIMITING
JP4578091B2 (en) 2003-12-16 2010-11-10 東洋インキ製造株式会社 Composition for light curable light scattering film constituting reflection type liquid crystal display device, and light scattering film using the same
KR20130116954A (en) 2005-12-28 2013-10-24 프레세니어스 카비 온콜로지 리미티드 A biocompatible, non-biodegradable, non-toxic polymer useful for nanoparticle pharmaceutical compositions
EP2295480A1 (en) * 2009-09-10 2011-03-16 Occlugel Implantable bio-resorbable polymer
US8772355B2 (en) * 2010-11-23 2014-07-08 Howard University Stealth polymeric particles for delivery of bioactive or diagnostic agents

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5130479A (en) * 1989-12-20 1992-07-14 Ceskoslovenska Akademie Ved Hydrolytically degradable hydrophilic gels and the method for preparation thereof using n,o-dimethacryloylhydroxylamine as a cross-linking agent
US20020064513A1 (en) * 2000-09-18 2002-05-30 Amarnath Maitra Sustained release and long residing ophthalmic formulation and the process of preparing the same
US20030018128A1 (en) * 2000-12-29 2003-01-23 Wang James H. Grafted biodegradable polymer blend compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SANT, SHILIPA ET AL.: "Effect of polymer architecture on surface properties, plasma protein adsorption, and cellular interactions of pegylated nanoparticles", JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART A, vol. 87A, no. 4, 15 December 2008 (2008-12-15), pages 885 - 895, XP055051513 *

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US20170240698A1 (en) 2017-08-24
US20120129797A1 (en) 2012-05-24
CA2818869C (en) 2019-10-29
EP2643382A4 (en) 2017-10-04
WO2012071441A2 (en) 2012-05-31
US20150209287A1 (en) 2015-07-30
US8921429B2 (en) 2014-12-30
CA2818869A1 (en) 2012-05-31
EP2643382A2 (en) 2013-10-02
US9675556B2 (en) 2017-06-13

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