CA2955438C - DEXTRANE CONJUGATES TO TARGET MACROPHAGES AND OTHER CELLS EXPRESSING THE D-MANBOSE BINDING TYPE C LECTIN RECEPTOR - Google Patents

DEXTRANE CONJUGATES TO TARGET MACROPHAGES AND OTHER CELLS EXPRESSING THE D-MANBOSE BINDING TYPE C LECTIN RECEPTOR

Info

Publication number
CA2955438C
CA2955438C CA2955438A CA2955438A CA2955438C CA 2955438 C CA2955438 C CA 2955438C CA 2955438 A CA2955438 A CA 2955438A CA 2955438 A CA2955438 A CA 2955438A CA 2955438 C CA2955438 C CA 2955438C
Authority
CA
Canada
Prior art keywords
compound
binding
mannose
use according
tilmanocept
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.)
Active
Application number
CA2955438A
Other languages
English (en)
French (fr)
Other versions
CA2955438A1 (en
Inventor
Larry Schlesinger
Eric Bachelder
Fred COPE
Wael N. JARJOUR
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.)
Individual
Original Assignee
Cardinal Health 414 LLC
Ohio State Innovation Foundation
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 Cardinal Health 414 LLC, Ohio State Innovation Foundation filed Critical Cardinal Health 414 LLC
Publication of CA2955438A1 publication Critical patent/CA2955438A1/en
Application granted granted Critical
Publication of CA2955438C publication Critical patent/CA2955438C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4409—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 4, e.g. isoniazid, iproniazid
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
    • C08B37/0021—Dextran, i.e. (alpha-1,4)-D-glucan; Derivatives thereof, e.g. Sephadex, i.e. crosslinked dextran
    • 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
    • A61K31/7004—Monosaccharides having only carbon, hydrogen and oxygen atoms
    • 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
    • A61K31/7008—Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
    • 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
    • A61K31/7016—Disaccharides, e.g. lactose, lactulose
    • 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
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/242—Gold; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/244—Lanthanides; Compounds thereof
    • 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
    • A61K47/54—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 compound
    • A61K47/549—Sugars, nucleosides, nucleotides or nucleic acids
    • 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
    • A61K47/61—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 the organic macromolecular compound being a polysaccharide or a derivative thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
    • A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
    • A61K49/0032—Methine dyes, e.g. cyanine dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/001—Preparation for luminescence or biological staining
    • A61K49/0013—Luminescence
    • A61K49/0017—Fluorescence in vivo
    • A61K49/005—Fluorescence in vivo characterised by the carrier molecule carrying the fluorescent agent
    • A61K49/0054—Macromolecular compounds, i.e. oligomers, polymers, dendrimers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/06—Macromolecular compounds, carriers being organic macromolecular compounds, i.e. organic oligomeric, polymeric, dendrimeric molecules
    • A61K51/065—Macromolecular compounds, carriers being organic macromolecular compounds, i.e. organic oligomeric, polymeric, dendrimeric molecules conjugates with carriers being macromolecules
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A61P31/06—Antibacterial agents for tuberculosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A61K33/243—Platinum; Compounds thereof
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Biochemistry (AREA)
  • Biomedical Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physics & Mathematics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Optics & Photonics (AREA)
  • Materials Engineering (AREA)
  • Pain & Pain Management (AREA)
  • Communicable Diseases (AREA)
  • Polymers & Plastics (AREA)
  • Pulmonology (AREA)
  • Rheumatology (AREA)
  • Oncology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Peptides Or Proteins (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2955438A 2014-07-17 2015-07-17 DEXTRANE CONJUGATES TO TARGET MACROPHAGES AND OTHER CELLS EXPRESSING THE D-MANBOSE BINDING TYPE C LECTIN RECEPTOR Active CA2955438C (en)

Applications Claiming Priority (15)

Application Number Priority Date Filing Date Title
US201462025991P 2014-07-17 2014-07-17
US62/025,991 2014-07-17
US201462027193P 2014-07-21 2014-07-21
US201462027220P 2014-07-21 2014-07-21
US62/027,193 2014-07-21
US62/027,220 2014-07-21
US201462027733P 2014-07-22 2014-07-22
US62/027,733 2014-07-22
US201562106194P 2015-01-21 2015-01-21
US62/106,194 2015-01-21
US201562187064P 2015-06-30 2015-06-30
US201562187132P 2015-06-30 2015-06-30
US62/187,132 2015-06-30
US62/187,064 2015-06-30
PCT/US2015/041009 WO2016011415A2 (en) 2014-07-17 2015-07-17 Compounds and compositions for targeting macrophages and other mannose-binding c-type lectin receptor high expressing cells and methods of treating and diagnosis using same

Publications (2)

Publication Number Publication Date
CA2955438A1 CA2955438A1 (en) 2016-01-21
CA2955438C true CA2955438C (en) 2024-07-02

Family

ID=55079179

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2955438A Active CA2955438C (en) 2014-07-17 2015-07-17 DEXTRANE CONJUGATES TO TARGET MACROPHAGES AND OTHER CELLS EXPRESSING THE D-MANBOSE BINDING TYPE C LECTIN RECEPTOR

Country Status (5)

Country Link
US (1) US20220211680A1 (https=)
EP (1) EP3169792A4 (https=)
JP (3) JP6722663B2 (https=)
CA (1) CA2955438C (https=)
WO (1) WO2016011415A2 (https=)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100196272A1 (en) 2009-01-30 2010-08-05 Neoprobe Corporation Compositions for radiolabeling diethylenetriaminepentaacetic acid (dtpa)-dextran
US10806803B2 (en) 2014-07-17 2020-10-20 Ohio State Innovation Foundation Compositions for targeting macrophages and other CD206 high expressing cells and methods of treating and diagnosis
WO2016011419A1 (en) * 2014-07-17 2016-01-21 Ohio State Innovation Foundation Compositions for targeting macrophages and other cd206 high expressing cells and methods of treating and diagnosis
WO2018067751A1 (en) * 2016-10-04 2018-04-12 Navidea Biopharmaceuticals, Inc. Compositions and methods for diagnosing and treating macrophage-related disorders using carbohydrate-based macromolecular carrier
EP3522899A4 (en) * 2016-10-07 2020-05-06 Navidea Biopharmaceuticals, Inc. Compounds and compositions for treating leishmaniasis and methods of diagnosis and treating using same
MX2019004029A (es) 2016-10-07 2019-09-27 Navidea Biopharmaceuticals Inc Compuestos y metodos para diagnosis y tratamiento de infecciones virales.
WO2019018815A1 (en) * 2017-07-21 2019-01-24 Navidea Biopharmaceuticals, Inc. USE OF 99MTC-TILMANOCEPT AND ASSOCIATED MOLECULAR CONSTRUCTS FOR THE IDENTIFICATION AND DIAGNOSIS OF MALIGNANT TUMORS, AND FOR THE MONITORING OF ANTI-TUMOR THERAPEUTIC INTERVENTIONS
BR112021019187A2 (pt) * 2019-03-27 2021-12-21 Navidea Biopharmaceuticals Inc Método para repolarização de um macrófago associado a tumor de m2 a m1, e, composto para repolarização de um macrófago associado a tumor de m2 a m1
US20210052639A1 (en) * 2019-08-19 2021-02-25 Navidea Biopharmaceuticals, Inc. Compositions and related methods for the ablation of m2 macrophages and myeloid derived suppressor cells
US20210145989A1 (en) * 2019-09-30 2021-05-20 Navidea Biopharmaceuticals, Inc. Compositions and related methods for blocking off-target localization of mannosylated dextrans and other cd206 ligands
EP4076540A4 (en) 2020-07-08 2024-02-21 Navidea Biopharmaceuticals, Inc. Synthesis of uniformly defined molecular weight mannosylated dextrans and derivatives thereof
CA3192041A1 (en) * 2020-08-21 2022-02-24 Resolute Science, Inc. Compositions and methods for targeting tumor-associated macrophages
EP4472643A1 (en) 2022-02-04 2024-12-11 Navidea Biopharmaceuticals, Inc. Altering net charge on mannosylated dextrans to maximize target tissue uptake and off target competitive blocking
JP2025517414A (ja) 2022-05-20 2025-06-05 ナビディア、バイオファーマスーティカルズ、インコーポレイテッド 分解性リンカーを介して新規ビスホスホネート薬物ペイロードを担持するｃｄ２０６標的化薬物送達ビヒクル
WO2024076988A2 (en) 2022-10-03 2024-04-11 Navidea Biopharmaceuticals, Inc. Amide linkages of sugar moieties to amine terminated leashes attached to carbohydrate polymers

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1178838B1 (en) * 1999-05-14 2004-09-29 The Regents of the University of California Macromolecular carrier based on dextran for drug and diagnostic agent delivery
US8273357B2 (en) * 2004-07-16 2012-09-25 Massachusetts Institute Of Technology Antigen-carbohydrate conjugates
US8343497B2 (en) * 2008-10-12 2013-01-01 The Brigham And Women's Hospital, Inc. Targeting of antigen presenting cells with immunonanotherapeutics
US20100196272A1 (en) * 2009-01-30 2010-08-05 Neoprobe Corporation Compositions for radiolabeling diethylenetriaminepentaacetic acid (dtpa)-dextran
US9101674B2 (en) * 2010-03-29 2015-08-11 Vib Vzw Targeting and in vivo imaging of tumor-associated macrophages
WO2012171035A1 (en) * 2011-06-10 2012-12-13 University Of Washington Through Its Center For Commercialization Carbohydrate-based compositions and methods for targeted drug delivery
US20130330274A1 (en) * 2012-05-22 2013-12-12 University of Virginia Patent Foundation d/b/a University of Virginia Licensing & Ventures Group Compositions and methods for detecting and treating cancer
CN114377143A (zh) * 2013-07-22 2022-04-22 康德乐健康414有限责任公司 用于诊断和治疗与表达cd206的细胞相关的病症的组合物、方法和药盒
WO2016011419A1 (en) * 2014-07-17 2016-01-21 Ohio State Innovation Foundation Compositions for targeting macrophages and other cd206 high expressing cells and methods of treating and diagnosis

Also Published As

Publication number Publication date
EP3169792A2 (en) 2017-05-24
US20220211680A1 (en) 2022-07-07
EP3169792A4 (en) 2018-04-11
JP6722663B2 (ja) 2020-07-15
WO2016011415A2 (en) 2016-01-21
WO2016011415A3 (en) 2016-03-17
JP2022109994A (ja) 2022-07-28
JP2017528585A (ja) 2017-09-28
JP7066780B2 (ja) 2022-05-13
CA2955438A1 (en) 2016-01-21
JP2020189977A (ja) 2020-11-26

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