AU2018270520B2 - Compounds for use as iron(III) MRI contrast agents - Google Patents

Compounds for use as iron(III) MRI contrast agents Download PDF

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Publication number
AU2018270520B2
AU2018270520B2 AU2018270520A AU2018270520A AU2018270520B2 AU 2018270520 B2 AU2018270520 B2 AU 2018270520B2 AU 2018270520 A AU2018270520 A AU 2018270520A AU 2018270520 A AU2018270520 A AU 2018270520A AU 2018270520 B2 AU2018270520 B2 AU 2018270520B2
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Australia
Prior art keywords
macrocyclic
iii
groups
pendant
substituted
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AU2018270520A
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AU2018270520A1 (en
Inventor
Didar ASIK
Janet R. Morrow
Eric M. SNYDER
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Research Foundation of the State University of New York
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Research Foundation of the State University of New York
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/02—Iron compounds
    • C07F15/025—Iron compounds without a metal-carbon linkage
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/085—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier conjugated systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
    • A61K49/106—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/12—Macromolecular compounds
    • A61K49/124—Macromolecular compounds dendrimers, dendrons, hyperbranched compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/12—Macromolecular compounds
    • A61K49/126—Linear polymers, e.g. dextran, inulin, PEG
    • A61K49/128—Linear polymers, e.g. dextran, inulin, PEG comprising multiple complex or complex-forming groups, being either part of the linear polymeric backbone or being pending groups covalently linked to the linear polymeric backbone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/14—Peptides, e.g. proteins
    • A61K49/143—Peptides, e.g. proteins the protein being an albumin, e.g. HSA, BSA, ovalbumin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D255/00—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00
    • C07D255/02—Heterocyclic compounds containing rings having three nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D249/00 - C07D253/00 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Epidemiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Magnetic Resonance Imaging Apparatus (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
AU2018270520A 2017-05-19 2018-05-21 Compounds for use as iron(III) MRI contrast agents Active AU2018270520B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201762508548P 2017-05-19 2017-05-19
US62/508,548 2017-05-19
PCT/US2018/033759 WO2018213853A1 (en) 2017-05-19 2018-05-21 Compounds for use as iron(iii) mri contrast agents

Publications (2)

Publication Number Publication Date
AU2018270520A1 AU2018270520A1 (en) 2019-12-12
AU2018270520B2 true AU2018270520B2 (en) 2022-01-06

Family

ID=64274805

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2018270520A Active AU2018270520B2 (en) 2017-05-19 2018-05-21 Compounds for use as iron(III) MRI contrast agents

Country Status (7)

Country Link
US (2) US11261208B2 (enExample)
EP (1) EP3624859A4 (enExample)
JP (1) JP7390284B2 (enExample)
KR (2) KR20250073575A (enExample)
CN (1) CN110944676A (enExample)
AU (1) AU2018270520B2 (enExample)
WO (1) WO2018213853A1 (enExample)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3624859A4 (en) * 2017-05-19 2021-03-03 The Research Foundation for The State University of New York COMPOUNDS FOR USE AS IRON (III) MRT CONTRAST AGENTS
JP7582942B2 (ja) * 2018-11-16 2024-11-13 ザ リサーチ ファウンデイション フォー ザ ステイト ユニバーシティー オブ ニューヨーク アニオン性ペンダントおよび補助基を含む、鉄（ｉｉｉ）ｍｒｉ造影剤として使用するための化合物
EP4308177A4 (en) * 2021-03-20 2025-07-09 Univ New York State Res Found MACROCYCLIC IRON(III) COMPLEXES WITH PENDANT HYDROXYL GROUPS AS MRI CONTRAST AGENTS
DE102021214708A1 (de) 2021-12-20 2023-06-22 Henkel Ag & Co. Kgaa Metallkomplexe und Geschirrspülmittel, die sie enthalten
IL317339A (en) 2022-07-28 2025-01-01 Bracco Imaging Spa 1,4-Bis-(2-hydroxybenzyl)-1,4,7-triazaciconanone derivatives and similar compounds as ligands in iron(III) complexes for use as MRI contrast agents
WO2025163025A1 (en) * 2024-01-31 2025-08-07 Bracco Imaging Spa Pyridophane macrocyclic ligands and fe(iii) complexes thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4885363A (en) * 1987-04-24 1989-12-05 E. R. Squibb & Sons, Inc. 1-substituted-1,4,7-triscarboxymethyl-1,4,7,10-tetraazacyclododecane and analogs
US10556873B2 (en) 2008-02-22 2020-02-11 Illinois Institute Of Technology Bimodal ligands with macrocyclic and acyclic binding moieties, complexes and compositions thereof, and methods of using
WO2012155076A2 (en) * 2011-05-11 2012-11-15 The Research Foundation Of State University Of New York Imaging contrast agents and uses thereof
EP3043828B1 (en) * 2013-09-12 2026-01-07 The Research Foundation for the State University of New York Macrocycles, cobalt and iron complexes of same, and methods of making and using same
EP3624859A4 (en) * 2017-05-19 2021-03-03 The Research Foundation for The State University of New York COMPOUNDS FOR USE AS IRON (III) MRT CONTRAST AGENTS

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
AUERBACH, U. et al., Inorg. Chem., 1990, vol. 29, pages 938-944 *
STOCKHEIM, C. et al., J. Chem. Soc., Dalton Trans., 1996, no. 23, pages 4409-4416 *
WIEGHARDT, K. et al., Inorg. Chem., 1982, no. 21, pages 4308-4314 *
YANG, C-T. et al., "Synthesis and Characterization of a Novel Macrocyclic Chelator with 3-Hydroxy-4-Pyrone Chelating Arms and Its Complexes with Medicinally Important Metals", Inorg. Chem., 2008, vol. 47, no. 7, pages 2719-2727 *

Also Published As

Publication number Publication date
AU2018270520A1 (en) 2019-12-12
CN110944676A (zh) 2020-03-31
US11261208B2 (en) 2022-03-01
EP3624859A4 (en) 2021-03-03
US12534487B2 (en) 2026-01-27
US20220259244A1 (en) 2022-08-18
KR20200010385A (ko) 2020-01-30
US20200079806A1 (en) 2020-03-12
KR102811655B1 (ko) 2025-05-21
JP2020520998A (ja) 2020-07-16
WO2018213853A1 (en) 2018-11-22
JP7390284B2 (ja) 2023-12-01
EP3624859A1 (en) 2020-03-25
KR20250073575A (ko) 2025-05-27

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