CA2316834A1 - Degradable heterobifunctional poly(ethylene glycol) acrylates and gels and conjugates derived therefrom - Google Patents

Degradable heterobifunctional poly(ethylene glycol) acrylates and gels and conjugates derived therefrom Download PDF

Info

Publication number
CA2316834A1
CA2316834A1 CA002316834A CA2316834A CA2316834A1 CA 2316834 A1 CA2316834 A1 CA 2316834A1 CA 002316834 A CA002316834 A CA 002316834A CA 2316834 A CA2316834 A CA 2316834A CA 2316834 A1 CA2316834 A1 CA 2316834A1
Authority
CA
Canada
Prior art keywords
degradable
acrylates
gels
ethylene glycol
derived therefrom
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
CA002316834A
Other languages
French (fr)
Other versions
CA2316834C (en
Inventor
J. Milton Harris
Xuan Zhao
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.)
Debio Recherche Pharmaceutique SA
Original Assignee
Shearwater Polymers, Inc.
J. Milton Harris
Xuan Zhao
Shearwater Corporation
Debio Recherche Pharmaceutique S.A.
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 Shearwater Polymers, Inc., J. Milton Harris, Xuan Zhao, Shearwater Corporation, Debio Recherche Pharmaceutique S.A. filed Critical Shearwater Polymers, Inc.
Publication of CA2316834A1 publication Critical patent/CA2316834A1/en
Application granted granted Critical
Publication of CA2316834C publication Critical patent/CA2316834C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02Polyalkylene oxides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/59Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
    • A61K47/60Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/329Polymers modified by chemical after-treatment with organic compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32Polymers modified by chemical after-treatment
    • C08G65/329Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3322Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00Applications
    • C08L2203/02Applications for biomedical use
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/81Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S530/00Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
    • Y10S530/81Carrier - bound or immobilized peptides or proteins and the preparation thereof, e.g. biological cell or cell fragment as carrier
    • Y10S530/812Peptides or proteins is immobilized on, or in, an organic carrier
    • Y10S530/815Carrier is a synthetic polymer
    • Y10S530/816Attached to the carrier via a bridging agent

Abstract

A heterobifunctional polyethylene glycol) is provided having a hydrolytically degradable linkage, a first terminus comprising an acrylate group, and a second terminus comprising a target such as a protein or pharmaceutical agent or a reactive moiety capable of coupling to a target. Hydrogels can be prepared. The hydrogels can be used as a carrier for a protein or a pharmaceutical agent that can be readily released in a controlled fashion.
CA002316834A 1998-01-07 1999-01-06 Degradable heterobifunctional poly(ethylene glycol) acrylates and gels and conjugates derived therefrom Expired - Fee Related CA2316834C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US7068098P 1998-01-07 1998-01-07
US60/070,680 1998-01-07
PCT/US1999/000594 WO1999034833A1 (en) 1998-01-07 1999-01-06 Degradable heterobifunctional poly(ethylene glycol) acrylates and gels and conjugates derived therefrom

Publications (2)

Publication Number Publication Date
CA2316834A1 true CA2316834A1 (en) 1999-07-15
CA2316834C CA2316834C (en) 2006-01-03

Family

ID=22096751

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002316834A Expired - Fee Related CA2316834C (en) 1998-01-07 1999-01-06 Degradable heterobifunctional poly(ethylene glycol) acrylates and gels and conjugates derived therefrom

Country Status (11)

Country Link
US (7) US6362276B1 (en)
EP (1) EP1053019B1 (en)
JP (1) JP3786832B2 (en)
AT (1) ATE255422T1 (en)
AU (1) AU755051B2 (en)
CA (1) CA2316834C (en)
DE (1) DE69913316T2 (en)
DK (1) DK1053019T3 (en)
ES (1) ES2211033T3 (en)
PT (1) PT1053019E (en)
WO (1) WO1999034833A1 (en)

Families Citing this family (203)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6057287A (en) 1994-01-11 2000-05-02 Dyax Corp. Kallikrein-binding "Kunitz domain" proteins and analogues thereof
US20020064546A1 (en) * 1996-09-13 2002-05-30 J. Milton Harris Degradable poly(ethylene glycol) hydrogels with controlled half-life and precursors therefor
WO1998012274A1 (en) 1996-09-23 1998-03-26 Chandrashekar Pathak Methods and devices for preparing protein concentrates
US8003705B2 (en) 1996-09-23 2011-08-23 Incept Llc Biocompatible hydrogels made with small molecule precursors
US6258351B1 (en) * 1996-11-06 2001-07-10 Shearwater Corporation Delivery of poly(ethylene glycol)-modified molecules from degradable hydrogels
US7642323B2 (en) 1997-11-06 2010-01-05 Nektar Therapeutics Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation
US6448369B1 (en) 1997-11-06 2002-09-10 Shearwater Corporation Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation
AU755051B2 (en) * 1998-01-07 2002-12-05 Debio Recherche Pharmaceutique S.A. Degradable heterobifunctional poly(ethylene glycol) acrylates and gels and conjugates derived therefrom
US7335220B2 (en) 2004-11-05 2008-02-26 Access Closure, Inc. Apparatus and methods for sealing a vascular puncture
GB2341185A (en) * 1998-09-07 2000-03-08 Polybiomed Ltd Polymerizable material and adhesive sheet material therefrom; dressings, electrodes and transdermal patches
WO2000015117A1 (en) 1998-09-17 2000-03-23 Focal, Inc. Self-cleaning fluid delivery device for medical applications
US6958212B1 (en) 1999-02-01 2005-10-25 Eidgenossische Technische Hochschule Zurich Conjugate addition reactions for the controlled delivery of pharmaceutically active compounds
ATE514729T1 (en) 1999-02-01 2011-07-15 Eidgenoess Tech Hochschule BIOMATERIALS ADDED BY NUCLEOPHILIC REACTION ON CONJUGATE UNSATURATED GROUPS
US7192713B1 (en) 1999-05-18 2007-03-20 President And Fellows Of Harvard College Stabilized compounds having secondary structure motifs
US6828412B1 (en) * 1999-09-03 2004-12-07 School Of Pharmacy, University Of London Degradable polymers
US7037992B2 (en) * 1999-09-29 2006-05-02 Sri International Olefin copolymers containing hydrolytically cleavable linkages and use thereof in degradable products
US6288184B1 (en) * 1999-09-29 2001-09-11 Sri International Hydrolytically degradable olefin copolymers
PT1455839E (en) * 1999-10-08 2013-04-24 Nektar Therapeutics Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation
ATE317868T1 (en) * 1999-12-22 2006-03-15 Nektar Therapeutics Al Corp STERICALLY HINDERED DERIVATIVES OF WATER SOLUBLE POLYMERS
US7291673B2 (en) 2000-06-02 2007-11-06 Eidgenossiche Technische Hochschule Zurich Conjugate addition reactions for the controlled delivery of pharmaceutically active compounds
ATE516820T1 (en) 2000-09-29 2011-08-15 Schering Corp PEGYLATED INTERLEUKIN 10
WO2002055185A2 (en) 2000-10-19 2002-07-18 Eidgenoess Tech Hochschule Block copolymers for multifunctional self-assembled systems
US7829074B2 (en) 2001-10-18 2010-11-09 Nektar Therapeutics Hydroxypatite-targeting poly(ethylene glycol) and related polymers
US7265186B2 (en) * 2001-01-19 2007-09-04 Nektar Therapeutics Al, Corporation Multi-arm block copolymers as drug delivery vehicles
TWI246524B (en) 2001-01-19 2006-01-01 Shearwater Corp Multi-arm block copolymers as drug delivery vehicles
GB0116143D0 (en) * 2001-07-02 2001-08-22 Amersham Pharm Biotech Uk Ltd Chemical capture reagent
EP2322229B1 (en) 2001-10-10 2016-12-21 Novo Nordisk A/S Remodeling and glycoconjugation of Factor IX
US7157277B2 (en) 2001-11-28 2007-01-02 Neose Technologies, Inc. Factor VIII remodeling and glycoconjugation of Factor VIII
US7173003B2 (en) 2001-10-10 2007-02-06 Neose Technologies, Inc. Granulocyte colony stimulating factor: remodeling and glycoconjugation of G-CSF
US7795210B2 (en) 2001-10-10 2010-09-14 Novo Nordisk A/S Protein remodeling methods and proteins/peptides produced by the methods
DK1578771T3 (en) 2001-10-10 2013-06-10 Novo Nordisk As Remodeling and glycoconjugation of peptides
US7214660B2 (en) 2001-10-10 2007-05-08 Neose Technologies, Inc. Erythropoietin: remodeling and glycoconjugation of erythropoietin
US7153829B2 (en) 2002-06-07 2006-12-26 Dyax Corp. Kallikrein-inhibitor therapies
EP2311432B1 (en) * 2002-06-07 2014-12-24 Dyax Corporation Modified kunitz domain polypeptides and their use for reducing ischemia or the onset of a systemic inflammatory response associated with a surgical procedure
US7217254B2 (en) 2002-09-20 2007-05-15 Genzyme Corporation Multi-pressure biocompatible agent delivery device and method
DE60336406D1 (en) 2002-10-16 2011-04-28 Purdue Pharma Lp ANTIBODIES BINDING TO CELL ASSOCIATED CA 125 / 0722P, AND METHOD FOR THEIR USE
US7311926B2 (en) * 2002-12-20 2007-12-25 Battelle Memorial Institute Biocomposite materials and methods for making the same
NZ542094A (en) 2003-03-14 2008-12-24 Neose Technologies Inc Branched polymer conjugates comprising a peptide and water-soluble polymer chains
SG155777A1 (en) 2003-04-09 2009-10-29 Neose Technologies Inc Glycopegylation methods and proteins/peptides produced by the methods
WO2006127896A2 (en) 2005-05-25 2006-11-30 Neose Technologies, Inc. Glycopegylated factor ix
US8791070B2 (en) 2003-04-09 2014-07-29 Novo Nordisk A/S Glycopegylated factor IX
EP1624847B1 (en) 2003-05-09 2012-01-04 BioGeneriX AG Compositions and methods for the preparation of human growth hormone glycosylation mutants
WO2005012484A2 (en) 2003-07-25 2005-02-10 Neose Technologies, Inc. Antibody-toxin conjugates
JP4739207B2 (en) * 2003-08-29 2011-08-03 ダイアックス コーポレーション PolyPEGylated protease inhibitors
US7786213B2 (en) * 2003-10-15 2010-08-31 The Regents Of The University Of California Biomacromolecule polymer conjugates
EP2332967B1 (en) 2003-11-05 2016-04-20 Dana-Farber Cancer Institute, Inc. Stabilized alpha helical peptides and uses thereof
US7842661B2 (en) 2003-11-24 2010-11-30 Novo Nordisk A/S Glycopegylated erythropoietin formulations
US8633157B2 (en) 2003-11-24 2014-01-21 Novo Nordisk A/S Glycopegylated erythropoietin
US20080305992A1 (en) 2003-11-24 2008-12-11 Neose Technologies, Inc. Glycopegylated erythropoietin
US7956032B2 (en) 2003-12-03 2011-06-07 Novo Nordisk A/S Glycopegylated granulocyte colony stimulating factor
US20060040856A1 (en) 2003-12-03 2006-02-23 Neose Technologies, Inc. Glycopegylated factor IX
US7842667B2 (en) 2003-12-22 2010-11-30 Regentis Biomaterials Ltd. Matrix composed of a naturally-occurring protein backbone cross linked by a synthetic polymer and methods of generating and using same
EP1722834B1 (en) * 2003-12-22 2012-06-27 Regentis Biomaterials Ltd. Matrix comprising naturally-occurring crosslinked protein backbone
EP1765853B1 (en) 2004-01-08 2015-10-28 ratiopharm GmbH O-linked glycosylation of G-CSF peptides
JP2008505853A (en) 2004-04-13 2008-02-28 クインテセンス バイオサイエンシーズ インコーポレーティッド Non-natural ribonuclease complex as a cytotoxic agent
ES2299776T3 (en) 2004-06-16 2008-06-01 Straumann Holding Ag BARRIER MEMBRANE.
US7282584B2 (en) 2004-06-16 2007-10-16 Straumann Holding Ag Methylene blue
EP1625856A1 (en) * 2004-08-13 2006-02-15 Complex Biosystems GmbH Hydrogel polymeric conjugates of a prodrug
US7968085B2 (en) 2004-07-05 2011-06-28 Ascendis Pharma A/S Hydrogel formulations
EP2111872B1 (en) * 2004-07-05 2020-12-23 Ascendis Pharma GmbH Hydrogel conjugates
WO2006010143A2 (en) 2004-07-13 2006-01-26 Neose Technologies, Inc. Branched peg remodeling and glycosylation of glucagon-like peptide-1 [glp-1]
WO2006031811A2 (en) 2004-09-10 2006-03-23 Neose Technologies, Inc. Glycopegylated interferon alpha
US7235530B2 (en) 2004-09-27 2007-06-26 Dyax Corporation Kallikrein inhibitors and anti-thrombolytic agents and uses thereof
EP3061461A1 (en) 2004-10-29 2016-08-31 ratiopharm GmbH Remodeling and glycopegylation of fibroblast growth factor (fgf)
ES2449195T3 (en) 2005-01-10 2014-03-18 Ratiopharm Gmbh Glycopegylated granulocyte colony stimulating factor
AU2006213822B2 (en) 2005-02-09 2011-05-26 Covidien Lp Synthetic sealants
US20060222596A1 (en) 2005-04-01 2006-10-05 Trivascular, Inc. Non-degradable, low swelling, water soluble radiopaque hydrogel polymer
US7517914B2 (en) 2005-04-04 2009-04-14 Boston Scientificscimed, Inc. Controlled degradation materials for therapeutic agent delivery
WO2006121569A2 (en) 2005-04-08 2006-11-16 Neose Technologies, Inc. Compositions and methods for the preparation of protease resistant human growth hormone glycosylation mutants
WO2007008300A2 (en) 2005-05-31 2007-01-18 ECOLE POLYTECHNIQUE FéDéRALE DE LAUSANNE Triblock copolymers for cytoplasmic delivery of gene-based drugs
WO2007007392A1 (en) * 2005-07-11 2007-01-18 Wako Pure Chemical Industries, Ltd. Novel polymer and method of measuring cholesterol therewith
US8568705B2 (en) 2005-07-18 2013-10-29 Nektar Therapeutics Method for preparing branched functionalized polymers using branched polyol cores
GB0515625D0 (en) * 2005-07-29 2005-09-07 Univ Manchester Hydrogel particle
US20070105755A1 (en) 2005-10-26 2007-05-10 Neose Technologies, Inc. One pot desialylation and glycopegylation of therapeutic peptides
JP2007112924A (en) * 2005-10-21 2007-05-10 National Institute For Materials Science Polymer cross-linking agent and liposome or cell cross-linked product using the cross-linking agent
WO2007056191A2 (en) 2005-11-03 2007-05-18 Neose Technologies, Inc. Nucleotide sugar purification using membranes
US7597882B2 (en) 2006-04-24 2009-10-06 Incept Llc Protein crosslinkers, crosslinking methods and applications thereof
US7872068B2 (en) 2006-05-30 2011-01-18 Incept Llc Materials formable in situ within a medical device
WO2007149594A2 (en) 2006-06-23 2007-12-27 Quintessence Biosciences, Inc. Modified ribonucleases
EP2049151A4 (en) 2006-07-17 2010-03-24 Quintessence Biosciences Inc Methods and compositions for the treatment of cancer
US20080274958A1 (en) 2006-07-21 2008-11-06 Neose Technologies, Inc. Glycosylation of peptides via o-linked glycosylation sequences
WO2008011165A2 (en) * 2006-07-21 2008-01-24 Nektar Therapeutics Al, Corporation Polymeric reagents comprising a terminal vinylic group and conjugates formed therefrom
US20080081031A1 (en) 2006-09-28 2008-04-03 Schering Corporation Use of Pegylated IL-10 to Treat Cancer
US8969532B2 (en) 2006-10-03 2015-03-03 Novo Nordisk A/S Methods for the purification of polypeptide conjugates comprising polyalkylene oxide using hydrophobic interaction chromatography
MX2009003470A (en) 2006-10-04 2009-04-14 Novo Nordisk As Glycerol linked pegylated sugars and glycopeptides.
US8394483B2 (en) 2007-01-24 2013-03-12 Micron Technology, Inc. Two-dimensional arrays of holes with sub-lithographic diameters formed by block copolymer self-assembly
PT2118123E (en) 2007-01-31 2016-02-10 Harvard College Stabilized p53 peptides and uses thereof
US8083953B2 (en) 2007-03-06 2011-12-27 Micron Technology, Inc. Registered structure formation via the application of directed thermal energy to diblock copolymer films
US8557128B2 (en) 2007-03-22 2013-10-15 Micron Technology, Inc. Sub-10 nm line features via rapid graphoepitaxial self-assembly of amphiphilic monolayers
EP2508531B1 (en) 2007-03-28 2016-10-19 President and Fellows of Harvard College Stitched polypeptides
NZ580030A (en) 2007-04-03 2012-06-29 Biogenerix Ag Methods of treatment using glycopegylated g-csf
US8294139B2 (en) 2007-06-21 2012-10-23 Micron Technology, Inc. Multilayer antireflection coatings, structures and devices including the same and methods of making the same
US8097175B2 (en) 2008-10-28 2012-01-17 Micron Technology, Inc. Method for selectively permeating a self-assembled block copolymer, method for forming metal oxide structures, method for forming a metal oxide pattern, and method for patterning a semiconductor structure
US7959975B2 (en) 2007-04-18 2011-06-14 Micron Technology, Inc. Methods of patterning a substrate
US8372295B2 (en) 2007-04-20 2013-02-12 Micron Technology, Inc. Extensions of self-assembled structures to increased dimensions via a “bootstrap” self-templating method
US20080287633A1 (en) * 2007-05-18 2008-11-20 Drumheller Paul D Hydrogel Materials
US8404124B2 (en) 2007-06-12 2013-03-26 Micron Technology, Inc. Alternating self-assembling morphologies of diblock copolymers controlled by variations in surfaces
WO2008154639A2 (en) 2007-06-12 2008-12-18 Neose Technologies, Inc. Improved process for the production of nucleotide sugars
US8080615B2 (en) 2007-06-19 2011-12-20 Micron Technology, Inc. Crosslinkable graft polymer non-preferentially wetted by polystyrene and polyethylene oxide
EP2195010A4 (en) * 2007-08-21 2012-03-14 Genzyme Corp Treatment with kallikrein inhibitors
US8207112B2 (en) 2007-08-29 2012-06-26 Biogenerix Ag Liquid formulation of G-CSF conjugate
WO2009048909A1 (en) * 2007-10-08 2009-04-16 Quintessence Biosciences, Inc. Compositions and methods for ribonuclease-based therapies
US8999492B2 (en) 2008-02-05 2015-04-07 Micron Technology, Inc. Method to produce nanometer-sized features with directed assembly of block copolymers
US8101261B2 (en) 2008-02-13 2012-01-24 Micron Technology, Inc. One-dimensional arrays of block copolymer cylinders and applications thereof
WO2009102952A2 (en) * 2008-02-13 2009-08-20 Hyperbranch Medical Technology, Inc. Crosslinked polyalkyleneimine hydrogels with tunable degradation rates
JP5150297B2 (en) * 2008-02-14 2013-02-20 ネクター セラピューティックス エイエル,コーポレイション Heterobifunctional polyethylene glycol derivatives and methods for their preparation
KR101582841B1 (en) 2008-02-27 2016-01-11 노보 노르디스크 에이/에스 Conjugated factor viii molecules
US8426313B2 (en) 2008-03-21 2013-04-23 Micron Technology, Inc. Thermal anneal of block copolymer films with top interface constrained to wet both blocks with equal preference
US8425982B2 (en) 2008-03-21 2013-04-23 Micron Technology, Inc. Methods of improving long range order in self-assembly of block copolymer films with ionic liquids
US8114300B2 (en) 2008-04-21 2012-02-14 Micron Technology, Inc. Multi-layer method for formation of registered arrays of cylindrical pores in polymer films
US8114301B2 (en) 2008-05-02 2012-02-14 Micron Technology, Inc. Graphoepitaxial self-assembly of arrays of downward facing half-cylinders
WO2010014258A2 (en) * 2008-08-01 2010-02-04 Nektar Therapeutics Al, Corporation Conjugates having a releasable linkage
JP5435536B2 (en) * 2008-09-04 2014-03-05 学校法人神奈川大学 Photodegradable block copolymer
CN102203126A (en) 2008-09-22 2011-09-28 爱勒让治疗公司 Methods for preparing purified polypeptide compositions
CN102227443B (en) 2008-10-01 2014-05-14 昆特森斯生物科学公司 Therapeutic ribonucleases
JP5814793B2 (en) 2008-11-25 2015-11-17 エコール ポリテクニク フェデラル ド ローザンヌ(エーペーエフエル) Block copolymer and use thereof
WO2010067378A2 (en) 2008-12-08 2010-06-17 Reliance Life Sciences Pvt. Ltd. Hydrogel composition
CA2744235A1 (en) 2009-01-06 2010-07-15 Dyax Corp. Treatment of mucositis with kallikrein inhibitors
AU2010204648B2 (en) 2009-01-14 2016-09-01 Aileron Therapeutics, Inc. Peptidomimetic macrocycles
CA2750242C (en) 2009-02-12 2018-05-22 Incept, Llc Drug delivery through hydrogel plugs
JP5684239B2 (en) 2009-05-04 2015-03-11 インセプト・リミテッド・ライアビリティ・カンパニーIncept Llc Biomaterial for track and puncture closure
LT2440239T (en) 2009-06-09 2017-12-11 Prolong Pharmaceuticals, LLC Hemoglobin compositions
JP5738291B2 (en) 2009-07-31 2015-06-24 サノフィ−アベンティス・ドイチュラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング Prodrugs containing insulin linker conjugates
AU2010277560B2 (en) 2009-07-31 2014-12-11 Sanofi-Aventis Deutschland Gmbh Long acting insulin composition
JP4704506B2 (en) * 2009-08-11 2011-06-15 財団法人川村理化学研究所 Organic-inorganic composite hydrogel and method for producing the same
CA2774973A1 (en) 2009-09-22 2011-03-31 Aileron Therapeutics, Inc. Peptidomimetic macrocycles
US20110081398A1 (en) * 2009-10-01 2011-04-07 Tyco Healthcare Group Lp Multi-mechanism surgical compositions
US8968785B2 (en) * 2009-10-02 2015-03-03 Covidien Lp Surgical compositions
US20110081701A1 (en) * 2009-10-02 2011-04-07 Timothy Sargeant Surgical compositions
JP5552310B2 (en) * 2009-12-24 2014-07-16 日清紡ホールディングス株式会社 Resin crosslinking agent
EP2521568B1 (en) 2010-01-06 2018-07-25 Dyax Corp. Plasma kallikrein binding proteins
US8524215B2 (en) * 2010-08-02 2013-09-03 Janssen Biotech, Inc. Absorbable PEG-based hydrogels
PT2603600T (en) 2010-08-13 2019-02-27 Aileron Therapeutics Inc Peptidomimetic macrocycles
US8304493B2 (en) 2010-08-20 2012-11-06 Micron Technology, Inc. Methods of forming block copolymers
EP2438930A1 (en) 2010-09-17 2012-04-11 Sanofi-Aventis Deutschland GmbH Prodrugs comprising an exendin linker conjugate
JP2014502152A (en) 2010-11-12 2014-01-30 ダナ ファーバー キャンサー インスティテュート,インコーポレイテッド Cancer treatment and diagnosis
IL310186A (en) 2011-01-06 2024-03-01 Takeda Pharmaceuticals Co Plasma kallikrein binding proteins
CA2852468A1 (en) 2011-10-18 2013-04-25 Aileron Therapeutics, Inc. Peptidomimetic macrocyles
US8900963B2 (en) 2011-11-02 2014-12-02 Micron Technology, Inc. Methods of forming semiconductor device structures, and related structures
AU2012362121B2 (en) 2011-12-29 2017-08-03 Dana-Farber Cancer Institute, Inc. Stabilized antiviral fusion helices
CA2864120A1 (en) 2012-02-15 2013-08-22 Aileron Therapeutics, Inc. Triazole-crosslinked and thioether-crosslinked peptidomimetic macrocycles
RU2017145921A (en) 2012-02-15 2019-02-21 Эйлерон Терапьютикс, Инк. PEPTIDOMIMETIC MACROCYCLES
JP5953459B2 (en) * 2012-03-27 2016-07-20 ネクター セラピューティクス Heterobifunctional polyethylene glycol derivatives and methods for their preparation
WO2014052647A2 (en) 2012-09-26 2014-04-03 President And Fellows Of Harvard College Proline-locked stapled peptides and uses thereof
US9087699B2 (en) 2012-10-05 2015-07-21 Micron Technology, Inc. Methods of forming an array of openings in a substrate, and related methods of forming a semiconductor device structure
BR112015009470A2 (en) 2012-11-01 2019-12-17 Aileron Therapeutics Inc disubstituted amino acids and their methods of preparation and use
KR20150131244A (en) 2013-03-13 2015-11-24 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 Stapled and stitched polypeptides and uses thereof
US10258698B2 (en) 2013-03-14 2019-04-16 Modernatx, Inc. Formulation and delivery of modified nucleoside, nucleotide, and nucleic acid compositions
WO2014151369A2 (en) 2013-03-15 2014-09-25 Dana-Farber Cancer Institute, Inc. Stabilized ezh2 peptides
US10087215B2 (en) 2013-03-15 2018-10-02 Dana-Farber Cancer Institute, Inc. Stabilized SOS1 peptides
CA2906775A1 (en) 2013-03-15 2014-09-18 Dana-Farber Cancer Institute, Inc. Bh4 stabilized peptides and uses thereof
CN105209054A (en) 2013-04-18 2015-12-30 阿尔莫生物科技股份有限公司 Methods of using interleukin-10 for treating diseases and disorders
US9229328B2 (en) 2013-05-02 2016-01-05 Micron Technology, Inc. Methods of forming semiconductor device structures, and related semiconductor device structures
CN105492460A (en) 2013-06-14 2016-04-13 哈佛大学的校长及成员们 Stabilized polypeptide insulin receptor modulators
EP3434277A1 (en) 2013-06-17 2019-01-30 Armo Biosciences, Inc. Method for assessing protein identity and stability
US10711106B2 (en) 2013-07-25 2020-07-14 The University Of Chicago High aspect ratio nanofibril materials
EP3041938A1 (en) 2013-09-03 2016-07-13 Moderna Therapeutics, Inc. Circular polynucleotides
CA2923029A1 (en) 2013-09-03 2015-03-12 Moderna Therapeutics, Inc. Chimeric polynucleotides
US9177795B2 (en) 2013-09-27 2015-11-03 Micron Technology, Inc. Methods of forming nanostructures including metal oxides
RU2016122957A (en) 2013-11-11 2017-12-19 Армо Байосайенсиз, Инк. Methods of using interleukin-10 for the treatment of diseases and disorders
AU2015235967B2 (en) 2014-03-27 2020-10-22 Takeda Pharmaceutical Company Limited Compositions and methods for treatment of diabetic macular edema
CN106795506B (en) 2014-05-14 2020-11-27 达特茅斯学院理事会 Deimmunized lysostaphin and methods of use
US10533039B2 (en) 2014-05-21 2020-01-14 President And Fellows Of Harvard College Ras inhibitory peptides and uses thereof
WO2015187295A2 (en) 2014-06-02 2015-12-10 Armo Biosciences, Inc. Methods of lowering serum cholesterol
SG11201702223UA (en) 2014-09-24 2017-04-27 Aileron Therapeutics Inc Peptidomimetic macrocycles and uses thereof
CN112972378A (en) 2014-09-24 2021-06-18 艾瑞朗医疗公司 Peptidomimetic macrocycles and formulations thereof
EP3209320B1 (en) 2014-10-22 2023-03-08 Armo Biosciences, Inc. Methods of using interleukin-10 for treating diseases and disorders
WO2016126615A1 (en) 2015-02-03 2016-08-11 Armo Biosciences, Inc. Methods of using interleukin-10 for treating diseases and disorders
EP3270945A4 (en) 2015-03-18 2018-09-05 Massachusetts Institute of Technology Selective mcl-1 binding peptides
BR112017019738A2 (en) 2015-03-20 2018-05-29 Aileron Therapeutics Inc peptidomimetic macrocycles and their uses
KR20180020141A (en) 2015-05-28 2018-02-27 아르모 바이오사이언시스 인코포레이티드 PEGylated interleukin-10 for cancer treatment
US10059741B2 (en) 2015-07-01 2018-08-28 Aileron Therapeutics, Inc. Peptidomimetic macrocycles
MX2017016251A (en) 2015-07-02 2018-04-20 Dana Farber Cancer Inst Inc Stabilized anti-microbial peptides.
CN108025040A (en) 2015-08-25 2018-05-11 阿尔莫生物科技股份有限公司 The method that disease and illness are treated using interleukin-10
AU2016316842C1 (en) 2015-08-28 2021-04-22 Dana-Farber Cancer Institute, Inc. Peptides binding to BFL-1
WO2017044633A1 (en) 2015-09-10 2017-03-16 Aileron Therapeutics, Inc. Peptidomimetic macrocycles as modulators of mcl-1
JP6184462B2 (en) * 2015-10-28 2017-08-23 ウェルズ ファーゴ バンク ナショナル アソシエイション Heterobifunctional polyethylene glycol derivatives and methods for their preparation
BR112018011622A2 (en) 2015-12-11 2018-11-27 Dyax Corp method to treat hereditary angioedema attack (hae) or reduce hae attack rate
JP7105696B2 (en) 2016-02-29 2022-07-25 デイナ ファーバー キャンサー インスティチュート,インコーポレイテッド Stapled Intracellular Targeting Antimicrobial Peptides to Treat Infections
US11198715B2 (en) 2016-07-22 2021-12-14 Massachusetts Institute Of Technology Selective Bfl-1 peptides
EP3503924B1 (en) 2016-08-26 2022-12-14 Dana-Farber Cancer Institute, Inc. Bcl-w polypeptides and mimetics for treating or preventing chemotherapy-induced peripheral neuropathy and hearing loss
WO2018170299A1 (en) 2017-03-15 2018-09-20 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Inhibitors of prokaryotic gene transcription and uses thereof
JP6361083B2 (en) * 2017-06-27 2018-07-25 ウェルズ ファーゴ バンク ナショナル アソシエイション Heterobifunctional polyethylene glycol derivatives and methods for their preparation
WO2019018499A2 (en) 2017-07-19 2019-01-24 Dana-Farber Cancer Institute, Inc. Stabilized anti-microbial peptides for the treatment of antibiotic-resistant bacterial infections
WO2019050523A1 (en) 2017-09-07 2019-03-14 Kindheart, Inc Modified animal organs for use in surgical simulators
US20200354413A1 (en) 2017-12-15 2020-11-12 Dana-Farber Cancer Institute, Inc. Stabilized peptide-mediated targeted protein degradation
EP3737404A1 (en) 2017-12-15 2020-11-18 Dana Farber Cancer Institute, Inc. Selective targeting of apoptosis proteins by structurally-stabilized and/or cysteine-reactive noxa peptides
US11952432B2 (en) 2018-02-07 2024-04-09 Dana-Farber Cancer Institute, Inc. Cell-permeable stapled peptide modules for cellular delivery
EP3765852A1 (en) 2018-03-14 2021-01-20 Dana Farber Cancer Institute, Inc. Stabilized peptides for biomarker detection
JP6500318B2 (en) * 2018-04-04 2019-04-17 ウェルズ ファーゴ バンク ナショナル アソシエイション Heterobifunctional polyethylene glycol derivative and method for preparing the same
EP3852783A1 (en) 2018-09-17 2021-07-28 Massachusetts Institute of Technology Peptides selective for bcl-2 family proteins
CA3135115A1 (en) 2019-04-18 2020-10-22 Dana-Farber Cancer Institute, Inc. Selective targeting of ubiquitin- and ubiquitin-like e1-activating enzymes by structurally-stabilized peptides
CN110668933A (en) * 2019-09-30 2020-01-10 兰州交通大学 Novel method for synthesizing allyl fatty alcohol polyoxyethylene ether carboxylic acid (APEA-7)
CN110759824A (en) * 2019-09-30 2020-02-07 兰州交通大学 Novel method for synthesizing allyl fatty alcohol polyoxyethylene ether carboxylic acid (APEA-3)
US20230116760A1 (en) 2019-12-16 2023-04-13 Dana-Farber Cancer Institute, Inc. Structurally-stabilized oncolytic peptides and uses thereof
AU2020408070A1 (en) 2019-12-20 2022-06-09 Dana-Farber Cancer Institute, Inc. Structurally-stabilized glucagon-like peptide 1 peptides and uses thereof
US20240124529A1 (en) 2020-03-04 2024-04-18 Dana-Farber Cancer Institute, Inc. ANTIVIRAL STRUCTURALLY-STABILIZED SARS-CoV-2 PEPTIDES AND USES THEREOF
CA3179872A1 (en) 2020-04-22 2021-10-28 Dana-Farber Cancer Institute, Inc. Antiviral structurally-stabilized ace2 helix 1 peptides and uses thereof
CA3179873A1 (en) 2020-04-27 2021-11-04 Dana-Farber Cancer Institute, Inc. Structurally-stabilized and hdmx-selective p53 peptides and uses thereof
CN116801908A (en) 2020-10-14 2023-09-22 丹娜法伯癌症研究院 Chimeric conjugates for degrading viral and host proteins and methods of use
EP4240395A1 (en) 2020-11-05 2023-09-13 Dana-Farber Cancer Institute, Inc. Antiviral structurally-stabilized ebolavirus peptides and uses thereof
CA3231587A1 (en) 2021-09-08 2023-03-16 Dana-Farber Cancer Institute, Inc. Antiviral structurally-stapled sars-cov-2 peptide- cholesterol conjugates and uses thereof
WO2023215784A1 (en) 2022-05-04 2023-11-09 Dana-Farber Cancer Institute, Inc. Ebolavirus surface glycoprotein peptides, conjugates, and uses thereof

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3419006A (en) 1966-08-08 1968-12-31 Union Carbide Corp Novel dressing and use thereof
US4179337A (en) 1973-07-20 1979-12-18 Davis Frank F Non-immunogenic polypeptides
US3963805A (en) 1974-10-30 1976-06-15 Union Carbide Corporation Water swellable poly(alkylene oxide)
DE3071070D1 (en) 1979-03-21 1985-10-17 Nat Res Dev Composition for the controlled release of a prostaglandine and process for its preparation
JPS585320A (en) 1981-07-01 1983-01-12 Toray Ind Inc Graft copolymer
EP0206448B1 (en) 1985-06-19 1990-11-14 Ajinomoto Co., Inc. Hemoglobin combined with a poly(alkylene oxide)
US5410016A (en) 1990-10-15 1995-04-25 Board Of Regents, The University Of Texas System Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
US5626863A (en) 1992-02-28 1997-05-06 Board Of Regents, The University Of Texas System Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
US5334640A (en) * 1992-04-08 1994-08-02 Clover Consolidated, Ltd. Ionically covalently crosslinked and crosslinkable biocompatible encapsulation compositions and methods
WO1993024476A1 (en) 1992-06-04 1993-12-09 Clover Consolidated, Limited Water-soluble polymeric carriers for drug delivery
US5840900A (en) 1993-10-20 1998-11-24 Enzon, Inc. High molecular weight polymer-based prodrugs
DE4342154A1 (en) * 1993-12-10 1995-06-14 Behringwerke Ag Amidinophenylalanine derivatives, process for their preparation, their use and agents containing them as anticoagulants
WO1996020012A2 (en) * 1994-12-23 1996-07-04 Middlesex Sciences, Inc. Methods for preparing and purifying macromolecular conjugates
WO1997005185A2 (en) 1995-07-28 1997-02-13 Focal, Inc. Multiblock biodegradable hydrogels for use as controlled release agents for drugs delivery and tissue treatment agents
EP0787749B1 (en) * 1995-08-23 2003-04-02 Mitsui Chemicals, Inc. Novel allyl ethers, polymers and polymeric solid electrolytes
ZA978537B (en) * 1996-09-23 1998-05-12 Focal Inc Polymerizable biodegradable polymers including carbonate or dioxanone linkages.
ZA987019B (en) 1997-08-06 1999-06-04 Focal Inc Hemostatic tissue sealants
US6316522B1 (en) * 1997-08-18 2001-11-13 Scimed Life Systems, Inc. Bioresorbable hydrogel compositions for implantable prostheses
US6448369B1 (en) * 1997-11-06 2002-09-10 Shearwater Corporation Heterobifunctional poly(ethylene glycol) derivatives and methods for their preparation
AU755051B2 (en) * 1998-01-07 2002-12-05 Debio Recherche Pharmaceutique S.A. Degradable heterobifunctional poly(ethylene glycol) acrylates and gels and conjugates derived therefrom
US6326276B1 (en) * 1999-08-10 2001-12-04 United Microelectronics Corp. Method for forming a capacitor in dram

Also Published As

Publication number Publication date
US6362276B1 (en) 2002-03-26
US8497357B2 (en) 2013-07-30
AU2221499A (en) 1999-07-26
EP1053019B1 (en) 2003-12-03
DE69913316D1 (en) 2004-01-15
AU755051B2 (en) 2002-12-05
US20110009589A1 (en) 2011-01-13
PT1053019E (en) 2004-04-30
CA2316834C (en) 2006-01-03
ES2211033T3 (en) 2004-07-01
US20120195846A1 (en) 2012-08-02
US20040086992A1 (en) 2004-05-06
US20070292931A1 (en) 2007-12-20
JP2003510375A (en) 2003-03-18
JP3786832B2 (en) 2006-06-14
US7166304B2 (en) 2007-01-23
WO1999034833A1 (en) 1999-07-15
US20040086991A1 (en) 2004-05-06
EP1053019A1 (en) 2000-11-22
DE69913316T2 (en) 2004-11-18
ATE255422T1 (en) 2003-12-15
DK1053019T3 (en) 2004-04-13
US7214388B2 (en) 2007-05-08
US20010016624A1 (en) 2001-08-23
WO1999034833A9 (en) 2005-03-17

Similar Documents

Publication Publication Date Title
CA2316834A1 (en) Degradable heterobifunctional poly(ethylene glycol) acrylates and gels and conjugates derived therefrom
CA2323048A1 (en) Poly(ethylene glycol) derivatives with proximal reactive groups
CA2304976A1 (en) Delivery of poly(ethylene glycol)-conjugated molecules from degradable hydrogels
CA2255637A1 (en) Conjugates of cis-docosahexaenoic acid and paclitaxel
CA2268433A1 (en) Improved interferon polymer conjugates
CA2301533A1 (en) Balloons made from liquid crystal polymer blends
CA2331264A1 (en) Compositions and methods for drug delivery
MY131553A (en) Lyophilized formulation of polyethylene oxide modified proteins with increased self-life
CA2127463A1 (en) Biodegradable polymers for cell transplantation
EP2111876A3 (en) Crosslinked polymer compositions and methods for their use
CA2203480A1 (en) Interferon conjugates
AU2606595A (en) Individualized cellulosic fibers crosslinked with polyacrylic acid polymers
AU2658495A (en) Absorbent structure containing individualized cellulosic fibers crosslinked with polyacrylic acid polymers
CA2230492A1 (en) Human growth hormone variants
AU5773798A (en) Pegylation process
AU1244688A (en) Degradable thermoplastic compositions
CA2312710A1 (en) Sustained release formulation containing three different types of polymers and tablet formed therefrom
AU7506691A (en) Isobutylene polymer having unsaturated group and preparation thereof
CA2068061A1 (en) Waterproof high-spf sunscreen compositions
CA2124218A1 (en) Cytotoxic drug therapy
CA2283939A1 (en) Non-antigenic branched polymer conjugates
AU4693696A (en) Cross-linked polymers made from 1,3,7-octatriene and like conjugated polyenes
CA2118614A1 (en) Resin Composition
GB9225448D0 (en) Improved synthesis of polymer bioactive conjugates
AU7347987A (en) Tumor necrosis factor formulation

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20150106