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WO2001045745A3 - A reversible linkage technology for controlled conjugation - Google Patents

A reversible linkage technology for controlled conjugation Download PDF

Info

Publication number
WO2001045745A3
WO2001045745A3 PCT/GB2000/004935 GB0004935W WO0145745A3 WO 2001045745 A3 WO2001045745 A3 WO 2001045745A3 GB 0004935 W GB0004935 W GB 0004935W WO 0145745 A3 WO0145745 A3 WO 0145745A3
Authority
WO
WIPO (PCT)
Prior art keywords
carrier
conjugation
controlled
peptides
peptide
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/GB2000/004935
Other languages
French (fr)
Other versions
WO2001045745A2 (en
Inventor
Nicholas Flinn
Tony Johnson
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.)
GlaxoSmithKline Biologicals SA
Sanofi Pasteur Holding Ltd
Original Assignee
SmithKline Beecham Biologicals SA
Acambis Research Ltd
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
Priority claimed from GBGB9930233.3A external-priority patent/GB9930233D0/en
Priority claimed from GB0004096A external-priority patent/GB0004096D0/en
Priority claimed from GB0020707A external-priority patent/GB0020707D0/en
Priority claimed from GB0020708A external-priority patent/GB0020708D0/en
Application filed by SmithKline Beecham Biologicals SA, Acambis Research Ltd filed Critical SmithKline Beecham Biologicals SA
Priority to AU22067/01A priority Critical patent/AU2206701A/en
Publication of WO2001045745A2 publication Critical patent/WO2001045745A2/en
Publication of WO2001045745A3 publication Critical patent/WO2001045745A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K47/62—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 a protein, peptide or polyamino acid
    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A61K47/646—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent the entire peptide or protein drug conjugate elicits an immune response, e.g. conjugate vaccines
    • 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
    • A61K47/62—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 a protein, peptide or polyamino acid
    • A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
    • A61K47/643—Albumins, e.g. HSA, BSA, ovalbumin or a Keyhole Limpet Hemocyanin [KHL]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Virology (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Peptides Or Proteins (AREA)

Abstract

The present invention describes a linkage for use in the conjugation of compounds (e.g. peptides) to carrier vehicles (e.g. macromolecules, polymers, dendrimers, proteins etc.), producing constructs of biological and immunological relevance. The ability to link an Epitope (such as a peptide) to a carrier (such as a protein) in a controlled and specific manner is of a paramount importance in the development of a potent, pharmaceutically relevant, immunogenic hapten-carrier construct, such as a vaccine. The invention provides a reversible linkage technology for controlled conjugation of compounds such as peptides or peptidic Epitopes to carriers such as proteins. It utilises an aryl aldehyde moiety to introduce an aldehyde functionality on to a carrier molecule (e.g. on to the surface of a protein carrier molecule). It uses a 2-hydroxy-4-alkoxy linker based on an aryl aldehyde to provide protection in the conjugation of a peptide to a carrier, by virtue of imine formation.
PCT/GB2000/004935 1999-12-21 2000-12-21 A reversible linkage technology for controlled conjugation Ceased WO2001045745A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU22067/01A AU2206701A (en) 1999-12-21 2000-12-21 A reversible linkage technology for controlled conjugation

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
GB9930233.3 1999-12-21
GBGB9930233.3A GB9930233D0 (en) 1999-12-21 1999-12-21 A reversible linkage technology for controlled conjugation
GB0004096A GB0004096D0 (en) 2000-02-22 2000-02-22 A reversible linkage technology for controlled conjugation
GB0004096.4 2000-02-22
GB0020707.6 2000-08-22
GB0020707A GB0020707D0 (en) 2000-08-22 2000-08-22 A reversible linkage technology for controlled conjugation
GB0020708.4 2000-08-22
GB0020708A GB0020708D0 (en) 2000-08-22 2000-08-22 A reversible linkage technology for controlled conjugation

Publications (2)

Publication Number Publication Date
WO2001045745A2 WO2001045745A2 (en) 2001-06-28
WO2001045745A3 true WO2001045745A3 (en) 2002-05-10

Family

ID=27447796

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2000/004935 Ceased WO2001045745A2 (en) 1999-12-21 2000-12-21 A reversible linkage technology for controlled conjugation

Country Status (2)

Country Link
AU (1) AU2206701A (en)
WO (1) WO2001045745A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1493030A2 (en) * 2002-04-08 2005-01-05 Amura Therapeutics Limited Charge-balanced chemoselective linkers
WO2020113094A1 (en) 2018-11-30 2020-06-04 Nuvation Bio Inc. Pyrrole and pyrazole compounds and methods of use thereof
JP7678465B1 (en) * 2023-11-09 2025-05-16 株式会社ファンペップ Vaccine composition for inducing anti-IgE antibodies

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992007876A1 (en) * 1990-10-24 1992-05-14 Henning Berlin Gmbh Chemie- Und Pharmawerk Ligand/carrier-protein conjugate
EP0622084A1 (en) * 1993-04-28 1994-11-02 Eli Lilly And Company Antibody-drug conjugates
WO1995003321A1 (en) * 1993-07-20 1995-02-02 Bionebraska, Inc. Method for endomodification of proteins
WO1997024459A1 (en) * 1995-12-29 1997-07-10 Phanos Technologoes, Inc. Method for reducing unwanted cellular adhesions
WO1998017628A2 (en) * 1996-10-22 1998-04-30 Peptide Therapeutics Limited A solid-phase technology for the preparation of amides
US6001364A (en) * 1993-05-05 1999-12-14 Gryphon Sciences Hetero-polyoxime compounds and their preparation by parallel assembly
WO2000050461A1 (en) * 1999-02-25 2000-08-31 Smithkline Beecham Biologicals S.A. Epitopes or mimotopes derived from the c-epsilon-3 or c-epsilon-4 domains of ige, antagonists thereof, and their therapeutic uses

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992007876A1 (en) * 1990-10-24 1992-05-14 Henning Berlin Gmbh Chemie- Und Pharmawerk Ligand/carrier-protein conjugate
EP0622084A1 (en) * 1993-04-28 1994-11-02 Eli Lilly And Company Antibody-drug conjugates
US6001364A (en) * 1993-05-05 1999-12-14 Gryphon Sciences Hetero-polyoxime compounds and their preparation by parallel assembly
WO1995003321A1 (en) * 1993-07-20 1995-02-02 Bionebraska, Inc. Method for endomodification of proteins
WO1997024459A1 (en) * 1995-12-29 1997-07-10 Phanos Technologoes, Inc. Method for reducing unwanted cellular adhesions
WO1998017628A2 (en) * 1996-10-22 1998-04-30 Peptide Therapeutics Limited A solid-phase technology for the preparation of amides
WO2000050461A1 (en) * 1999-02-25 2000-08-31 Smithkline Beecham Biologicals S.A. Epitopes or mimotopes derived from the c-epsilon-3 or c-epsilon-4 domains of ige, antagonists thereof, and their therapeutic uses

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
KLINGUER C ET AL: "Synthesis Of Hydrazinopeptides Using Solid Phase N-Amination. Application To Chemical Ligation", TETRAHEDRON LETTERS,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 37, no. 40, 30 September 1996 (1996-09-30), pages 7259 - 7262, XP004030879, ISSN: 0040-4039 *
LEMIEUX G A ET AL: "Chemoselective ligation reactions with proteins, oligosaccharides and cells", TRENDS IN BIOTECHNOLOGY,GB,ELSEVIER PUBLICATIONS, CAMBRIDGE, vol. 16, no. 12, 1 December 1998 (1998-12-01), pages 506 - 513, XP004143811, ISSN: 0167-7799 *
SIEGEL ET AL: "CALICHEAMICIN DERIVATIVES CONJUGATED TO MONOCLONAL ANTIBODIES:DETERMINATION OF LOADING VALUES AND DISTRIBUTIONS BY INFRARED AND UV MATRIX-ASSISTED LASER DESORPTION/IONIZATION MASS SPECTROMETRY AND ELECTROSPRAY IONIZATION MASS SPECTROMETRY", ANALYTICAL CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY. COLUMBUS, vol. 69, no. 14, 15 July 1997 (1997-07-15), pages 2716 - 2726, XP002128444, ISSN: 0003-2700 *

Also Published As

Publication number Publication date
AU2206701A (en) 2001-07-03
WO2001045745A2 (en) 2001-06-28

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