WO2008089491A2 - Modifications of peptide compositions to increase stability and delivery efficiency - Google Patents

Modifications of peptide compositions to increase stability and delivery efficiency Download PDF

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Publication number
WO2008089491A2
WO2008089491A2 PCT/US2008/051706 US2008051706W WO2008089491A2 WO 2008089491 A2 WO2008089491 A2 WO 2008089491A2 US 2008051706 W US2008051706 W US 2008051706W WO 2008089491 A2 WO2008089491 A2 WO 2008089491A2
Authority
WO
WIPO (PCT)
Prior art keywords
peptide
composition
carrier
cargo
therapeutic
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/US2008/051706
Other languages
English (en)
French (fr)
Other versions
WO2008089491A3 (en
Inventor
Derek Maclean
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.)
Kai Pharmaceuticals Inc
Original Assignee
Kai Pharmaceuticals Inc
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 Kai Pharmaceuticals Inc filed Critical Kai Pharmaceuticals Inc
Priority to CA2675665A priority Critical patent/CA2675665C/en
Priority to KR1020177024556A priority patent/KR20170104634A/ko
Priority to EP08728081.4A priority patent/EP2109619B1/en
Priority to JP2009546577A priority patent/JP2010516707A/ja
Priority to CN2008800085591A priority patent/CN101675067B/zh
Priority to KR1020157036605A priority patent/KR101775929B1/ko
Priority to EP17161141.1A priority patent/EP3248985B1/en
Priority to AU2008206077A priority patent/AU2008206077A1/en
Priority to KR1020197036654A priority patent/KR102274003B1/ko
Publication of WO2008089491A2 publication Critical patent/WO2008089491A2/en
Publication of WO2008089491A3 publication Critical patent/WO2008089491A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/96—Stabilising an enzyme by forming an adduct or a composition; Forming enzyme conjugates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K19/00—Hybrid peptides, i.e. peptides covalently bound to nucleic acids, or non-covalently bound protein-protein complexes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/10—Peptides having 12 to 20 amino acids
    • 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
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • 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
    • 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
    • A61K47/645—Polycationic or polyanionic oligopeptides, polypeptides or polyamino acids, e.g. polylysine, polyarginine, polyglutamic acid or peptide TAT
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/12—Transferases (2.) transferring phosphorus containing groups, e.g. kinases (2.7)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K2319/00—Fusion polypeptide
    • C07K2319/31—Fusion polypeptide fusions, other than Fc, for prolonged plasma life, e.g. albumin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y207/00—Transferases transferring phosphorus-containing groups (2.7)
    • C12Y207/11—Protein-serine/threonine kinases (2.7.11)
    • C12Y207/11013—Protein kinase C (2.7.11.13)

Definitions

  • Figure 4 shows illustrate the conversion of a therapeutic peptide comprising a carrier peptide and a cargo peptide linked via a disulfide bond to a therapeutic peptide in linear form.
  • This linear peptide (KP-01547) has been capped at its amino and carboxy termini and contains a short amino acid sequence linker.
  • an aliphatic residue is placed at the penultimate carboxy terminal position of the peptide to reduce the rate of disulfide bond exchange.
  • the aliphatic residue can be place at either the amino terminal or carboxy terminal side of the residue, or at both sides.
  • Disulfide bond exchange can be eliminated completely by linking the carrier and cargo peptides to form a single, linear peptide. This method is discussed below.
  • Residues in the recognition sequence can be moved or removed to destroy the recognition site.
  • a conservative substitution is made with one or more of the amino acids which comprise an identified protease recognition site.
  • the side chains of these amino acids possess a variety of chemical properties.
  • the most common amino acids are categorized into 9 groups, listed below. Substitution within these groups is considered to be a conservative substitution.
  • carrier and cargo peptides are linked by a peptide bond to form a linear peptide.
  • Stability and potency of the therapeutic peptides can also be increased through the construction of peptide multimers, wherein a plurality of cargo peptides is linked to one or more carrier peptides.
  • An additional embodiment of the invention involving a cleavable linker sequence is also discussed.
  • carries include octa-Arg, octa-D-Arg, and Antennapedia derived peptides, which are known in the art.
  • Modification of the carrier showed the great propensity in improving the half life of the composition while modification of the cargo showed little effect.
  • CELGSLQAEDD linked to a TAT peptide with a N-Term Cys, which is capped at both ends and disulfide conjugated to the cargo.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Zoology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Wood Science & Technology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biophysics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
PCT/US2008/051706 2007-01-19 2008-01-22 Modifications of peptide compositions to increase stability and delivery efficiency Ceased WO2008089491A2 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CA2675665A CA2675665C (en) 2007-01-19 2008-01-22 Modifications of peptide compositions to increase stability and delivery efficiency
KR1020177024556A KR20170104634A (ko) 2007-01-19 2008-01-22 안정성 및 전달 효율을 증가시키기 위한 펩타이드 조성물의 변형
EP08728081.4A EP2109619B1 (en) 2007-01-19 2008-01-22 Modifications of peptide compositions to increase stability and delivery efficiency
JP2009546577A JP2010516707A (ja) 2007-01-19 2008-01-22 ペプチド組成物の安定性および送達効率を上昇させるための修飾方法
CN2008800085591A CN101675067B (zh) 2007-01-19 2008-01-22 肽组合物的修饰以提高稳定性和递送效率
KR1020157036605A KR101775929B1 (ko) 2007-01-19 2008-01-22 안정성 및 전달 효율을 증가시키기 위한 펩타이드 조성물의 변형
EP17161141.1A EP3248985B1 (en) 2007-01-19 2008-01-22 Modifications of peptide compositions to increase stability and delivery efficiency
AU2008206077A AU2008206077A1 (en) 2007-01-19 2008-01-22 Modifications of peptide compositions to increase stability and delivery efficiency
KR1020197036654A KR102274003B1 (ko) 2007-01-19 2008-01-22 안정성 및 전달 효율을 증가시키기 위한 펩타이드 조성물의 변형

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US88141907P 2007-01-19 2007-01-19
US60/881,419 2007-01-19
US94528507P 2007-06-20 2007-06-20
US60/945,285 2007-06-20

Publications (2)

Publication Number Publication Date
WO2008089491A2 true WO2008089491A2 (en) 2008-07-24
WO2008089491A3 WO2008089491A3 (en) 2008-11-27

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/051706 Ceased WO2008089491A2 (en) 2007-01-19 2008-01-22 Modifications of peptide compositions to increase stability and delivery efficiency

Country Status (8)

Country Link
US (7) US8067532B2 (enExample)
EP (2) EP2109619B1 (enExample)
JP (7) JP2010516707A (enExample)
KR (4) KR20090115852A (enExample)
CN (3) CN103524623A (enExample)
AU (1) AU2008206077A1 (enExample)
CA (2) CA2989778C (enExample)
WO (1) WO2008089491A2 (enExample)

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WO2010111533A3 (en) * 2009-03-25 2010-11-18 Kai Pharmaceuticals, Inc. Transdermal delivery of pkc modulatory peptides through microporated skin
US8377880B2 (en) 2009-07-29 2013-02-19 Kai Pharmaceuticals, Inc. Therapeutic agents for reducing parathyroid hormone levels
WO2013128003A1 (en) * 2012-03-01 2013-09-06 Novo Nordisk A/S N-terminally modified oligopeptides and uses thereof
US8969299B2 (en) 2011-06-08 2015-03-03 Kai Pharmaceuticals, Inc. Therapeutic agents for regulating serum phosphorus
US8987200B2 (en) 2006-11-16 2015-03-24 Kai Pharmaceuticals, Inc. Polycationic calcium modulator peptides for the treatment of hyperparathyroidism and hypercalcemic disorders
WO2021002408A1 (ja) 2019-07-02 2021-01-07 Ａｇｃ株式会社 ペプチド及びその製造方法
US11162500B2 (en) 2013-06-28 2021-11-02 Amgen Inc. Stable liquid formulation of AMG 416 (etelcalcetide)
WO2023048236A1 (ja) 2021-09-22 2023-03-30 Ａｇｃ株式会社 ペプチド

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