CA2791122C - Methods for preparing peg-hemoglobin conjugates using reduced reactant ratios - Google Patents

Methods for preparing peg-hemoglobin conjugates using reduced reactant ratios Download PDF

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Publication number
CA2791122C
CA2791122C CA2791122A CA2791122A CA2791122C CA 2791122 C CA2791122 C CA 2791122C CA 2791122 A CA2791122 A CA 2791122A CA 2791122 A CA2791122 A CA 2791122A CA 2791122 C CA2791122 C CA 2791122C
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peg
concentration
conjugate
mal
molecular weight
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French (fr)
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CA2791122A1 (en
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Ashok Malavalli
Kim D. Vandegriff
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/41—Porphyrin- or corrin-ring-containing peptides
    • A61K38/42—Haemoglobins; Myoglobins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
    • C08H1/00—Macromolecular products derived from proteins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal 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
    • A61K47/51—Medicinal 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
    • A61K47/56—Medicinal 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
    • A61K47/59—Medicinal 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
    • A61K47/60—Medicinal 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/795—Porphyrin- or corrin-ring-containing peptides
    • C07K14/805—Haemoglobins; Myoglobins
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/72—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood pigments, e.g. haemoglobin, bilirubin or other porphyrins; involving occult blood
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Hematology (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Urology & Nephrology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Diabetes (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physics & Mathematics (AREA)
  • Cell Biology (AREA)
  • Microbiology (AREA)
  • Food Science & Technology (AREA)
  • Biotechnology (AREA)
  • Analytical Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Medicinal Preparation (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2791122A 2010-02-25 2011-02-23 Methods for preparing peg-hemoglobin conjugates using reduced reactant ratios Active CA2791122C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US30823810P 2010-02-25 2010-02-25
US61/308,238 2010-02-25
PCT/US2011/025888 WO2011106396A1 (en) 2010-02-25 2011-02-23 Methods for preparing peg-hemoglobin conjugates using reduced reactant ratios

Publications (2)

Publication Number Publication Date
CA2791122A1 CA2791122A1 (en) 2011-09-01
CA2791122C true CA2791122C (en) 2019-08-27

Family

ID=44507180

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2791122A Active CA2791122C (en) 2010-02-25 2011-02-23 Methods for preparing peg-hemoglobin conjugates using reduced reactant ratios

Country Status (8)

Country Link
US (1) US9493616B2 (cg-RX-API-DMAC10.html)
EP (1) EP2539715B1 (cg-RX-API-DMAC10.html)
JP (1) JP2013520512A (cg-RX-API-DMAC10.html)
KR (1) KR20130067243A (cg-RX-API-DMAC10.html)
CN (1) CN102859364A (cg-RX-API-DMAC10.html)
AU (2) AU2011220885A1 (cg-RX-API-DMAC10.html)
CA (1) CA2791122C (cg-RX-API-DMAC10.html)
WO (1) WO2011106396A1 (cg-RX-API-DMAC10.html)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109731098A (zh) 2012-03-29 2019-05-10 桑加特公司 双阿司匹林交联聚乙二醇化血红蛋白
WO2013151776A1 (en) 2012-04-03 2013-10-10 Sangart, Inc. Succinimide-activated nitroxyl compounds and methods for the use thereof for nitroxylation of proteins
EP3655019A4 (en) 2017-07-18 2021-04-21 Virtech Bio, Inc. BLOOD SUBSTITUTES INCLUDING HEMOGLOBIN AND METHODS OF MANUFACTURING
US11857605B2 (en) 2021-03-01 2024-01-02 Billion King International Limited Thiosuccinyl-crosslinked hemoglobin conjugates and methods of use and preparation thereof
US20250064724A1 (en) * 2021-11-18 2025-02-27 Virginia Commonwealth University Modular field-stable bio-artificial blood substitute
WO2025219465A1 (en) * 2024-04-19 2025-10-23 Danmarks Tekniske Universitet Hemoglobin-based oxygen carrier

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2161086B2 (de) 1971-12-09 1975-04-24 Anton Cramer & Co, 4402 Greven Daunen- und federndichtes Gewebe
DE2449885C3 (de) 1974-10-21 1980-04-30 Biotest-Serum-Institut Gmbh, 6000 Frankfurt Verfahren zur Herstellung von chemisch modifizierten haltbaren Hämoglobinpräparaten sowie das nach diesem Verfahren hergestellte modifizierte Hämoglobinpräparat
US4001200A (en) 1975-02-27 1977-01-04 Alza Corporation Novel polymerized, cross-linked, stromal-free hemoglobin
US4001401A (en) 1975-02-02 1977-01-04 Alza Corporation Blood substitute and blood plasma expander comprising polyhemoglobin
JPS6023084B2 (ja) 1979-07-11 1985-06-05 味の素株式会社 代用血液
JPS57206622A (en) 1981-06-10 1982-12-18 Ajinomoto Co Inc Blood substitute
US4529719A (en) 1983-05-04 1985-07-16 Tye Ross W Modified crosslinked stroma-free tetrameric hemoglobin
EP0206448B1 (en) 1985-06-19 1990-11-14 Ajinomoto Co., Inc. Hemoglobin combined with a poly(alkylene oxide)
CA1312009C (en) 1986-11-10 1992-12-29 Carl W. Rausch Extra pure semi-synthetic blood substitute
US5449759A (en) 1987-05-16 1995-09-12 Somatogen, Inc. Hemoglobins with intersubunit desulfide bonds
US5234903A (en) 1989-11-22 1993-08-10 Enzon, Inc. Chemically modified hemoglobin as an effective, stable non-immunogenic red blood cell substitute
US5650388A (en) 1989-11-22 1997-07-22 Enzon, Inc. Fractionated polyalkylene oxide-conjugated hemoglobin solutions
US5585484A (en) * 1995-04-19 1996-12-17 Albert Einstein College Of Medicine Of Yeshiva University, A Division Of Yeshiva University Hemoglobin crosslinkers
US6054427A (en) 1997-02-28 2000-04-25 The Regents Of The University Of California Methods and compositions for optimization of oxygen transport by cell-free systems
EP1121165A1 (en) * 1998-10-15 2001-08-08 Sangart, Inc. Method for production of stroma-free hemoglobin
US7019117B2 (en) * 2001-07-19 2006-03-28 Albert Einstein College Of Medicine Of Yeshiva University Size enhanced hemoglobins: surface decoration and crosslinking of the protein with polyoxy alkylene glycols
US20030153491A1 (en) 2002-01-11 2003-08-14 Winslow Robert M. Methods and compositions for oxygen transport comprising a high oxygen affinity modified hemoglobin
US7144989B2 (en) * 2002-03-25 2006-12-05 Albert Einstein College Of Medicine Of Yeshiva University Pegylated non-hypertensive hemoglobins, methods of preparing same, and uses thereof
AU2003299700B2 (en) * 2002-12-23 2009-03-26 Albert Einstein College Of Medicine Of Yeshiva University Modified hemoglobin and methods of making same
CN1219811C (zh) * 2003-01-22 2005-09-21 中国科学院过程工程研究所 带单甲氧基聚乙二醇长尾的蛋白质修饰剂及制法和用途
CN1997666A (zh) * 2003-02-26 2007-07-11 印特缪恩股份有限公司 聚乙二醇修饰的干扰素组合物及其使用方法
DE602005023191D1 (de) 2004-08-31 2010-10-07 Sangart Inc Verfahren zur verbesserung der hämodynamischen stabilität mit sauerstoff-tragenden zusammensetzungen
EP1863503B1 (en) 2005-03-07 2019-05-22 Sangart, Inc. Composition for delivering carbon monoxide (co) and nitric ozide (no) co to tissue using heme proteins as carriers
US8697645B2 (en) * 2007-03-13 2014-04-15 Albert Einstein College Of Medicine Of Yeshiva University Second generation low oxygen affinity pegylated hemoglobins as oxygen-carrying plasma expanders
US8021858B2 (en) 2008-09-22 2011-09-20 Sangart, Inc. Method for making polyalkylene oxide modified hemoglobin
US20130041134A1 (en) 2009-11-05 2013-02-14 Sangart ,Inc. Methods for preparing polyethylene glycol maleimide using n-(2-hydroxyethyl) maleimide as a starting material

Also Published As

Publication number Publication date
EP2539715A4 (en) 2016-03-02
JP2013520512A (ja) 2013-06-06
KR20130067243A (ko) 2013-06-21
EP2539715B1 (en) 2021-12-22
EP2539715A1 (en) 2013-01-02
WO2011106396A1 (en) 2011-09-01
AU2011220885A1 (en) 2012-09-06
US20130217860A1 (en) 2013-08-22
AU2017232073B2 (en) 2019-01-31
AU2017232073A1 (en) 2017-10-12
CN102859364A (zh) 2013-01-02
CA2791122A1 (en) 2011-09-01
US9493616B2 (en) 2016-11-15

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