AU2018325283B2 - Therapeutic metal complexes and ligands and methods of making and using same - Google Patents

Therapeutic metal complexes and ligands and methods of making and using same Download PDF

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Publication number
AU2018325283B2
AU2018325283B2 AU2018325283A AU2018325283A AU2018325283B2 AU 2018325283 B2 AU2018325283 B2 AU 2018325283B2 AU 2018325283 A AU2018325283 A AU 2018325283A AU 2018325283 A AU2018325283 A AU 2018325283A AU 2018325283 B2 AU2018325283 B2 AU 2018325283B2
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Australia
Prior art keywords
aliphatic
heteroaliphatic
heteroaryl
aryl
compound
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AU2018325283A
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AU2018325283A1 (en
Inventor
Chris BEAUDRY
Joseph BECKMAN
James Hurst
John Sirois
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Oregon State University
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Oregon State University
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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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
    • 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
    • A61K31/13—Amines
    • A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/428—Thiazoles condensed with carbocyclic rings
    • 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
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • 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
    • A61K33/34—Copper; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
AU2018325283A 2017-09-01 2018-08-31 Therapeutic metal complexes and ligands and methods of making and using same Active AU2018325283B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201762553714P 2017-09-01 2017-09-01
US62/553,714 2017-09-01
PCT/US2018/049163 WO2019046761A1 (en) 2017-09-01 2018-08-31 THERAPEUTIC METAL COMPLEXES AND LIGANDS, METHODS OF MAKING AND USING SAME

Publications (2)

Publication Number Publication Date
AU2018325283A1 AU2018325283A1 (en) 2020-03-12
AU2018325283B2 true AU2018325283B2 (en) 2023-11-16

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Family Applications (1)

Application Number Title Priority Date Filing Date
AU2018325283A Active AU2018325283B2 (en) 2017-09-01 2018-08-31 Therapeutic metal complexes and ligands and methods of making and using same

Country Status (8)

Country Link
US (2) US11596651B2 (https=)
EP (1) EP3676271A1 (https=)
JP (3) JP2020532538A (https=)
CN (1) CN111278835A (https=)
AU (1) AU2018325283B2 (https=)
CA (1) CA3074258A1 (https=)
IL (1) IL272895B2 (https=)
WO (1) WO2019046761A1 (https=)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL272895B2 (en) * 2017-09-01 2025-06-01 Univ Oregon State Therapeutic metal complexes and ligands and methods of making and using same
EP4003361A1 (en) * 2019-07-25 2022-06-01 ALS Therapy Development Institute Cuptsm for the treatment of neurodegenerative disorders
US12012422B2 (en) * 2020-08-26 2024-06-18 Als Therapy Development Institute Copper complexes for treatment of neurodegenerative disorders

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2166676A1 (en) * 1995-01-09 1996-07-10 Yasuhisa Fujibayashi Diagnostic agent for hypoxia or mitochondrial dysfunction comprising radioactive copper complex of dithiosemicarbazone derivative or diamine diol schiff base derivative
WO2008061306A1 (en) * 2006-11-20 2008-05-29 The University Of Melbourne Metal delivery agents and therapeutic uses of the same

Family Cites Families (9)

* Cited by examiner, † Cited by third party
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NL7403524A (en) 1959-09-15 1974-05-27 Pharmaceutical compsn. - contg. alpha-dithiosemicarbazone active against trichomonas vaginalis
US4107210A (en) 1976-09-07 1978-08-15 The Dow Chemical Company Synthesis of alpha-diketones
GB0617299D0 (en) * 2006-09-01 2006-10-11 Isis Innovation Compounds for imaging and therapy
JP5711142B2 (ja) * 2008-12-12 2015-04-30 ザ ユニバーシティ オブ メルボルン 非対称性ビス（チオセミカルバゾン）の調製方法
AU2014346476B2 (en) * 2013-11-11 2019-01-24 Collaborative Medicinal Development, Llc Metal complexes and methods of treatment
WO2017070752A1 (en) * 2015-10-29 2017-05-04 The University Of Queensland Imaging agents
WO2017214546A1 (en) * 2016-06-10 2017-12-14 University Of Louisville Research Foundation, Inc. Compounds, related compositions, catalysts, electrochemical cells, fuel cells, their preparation and their uses
WO2018204564A1 (en) * 2017-05-04 2018-11-08 University Of Louisville Research Foundation, Inc. Thiosemicarbazone derivatives as anti-cancer agents
IL272895B2 (en) * 2017-09-01 2025-06-01 Univ Oregon State Therapeutic metal complexes and ligands and methods of making and using same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2166676A1 (en) * 1995-01-09 1996-07-10 Yasuhisa Fujibayashi Diagnostic agent for hypoxia or mitochondrial dysfunction comprising radioactive copper complex of dithiosemicarbazone derivative or diamine diol schiff base derivative
WO2008061306A1 (en) * 2006-11-20 2008-05-29 The University Of Melbourne Metal delivery agents and therapeutic uses of the same

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
ALSOP, L. et al., " Investigations into some aryl substituted bis(thiosemicarbazones) and their copper complexes", Inorganica Chimica Acta, 2005, vol. 358, pages 2770–2780 *
Ballschmiter, K. et al., "SUBSTITUENTENEFFEKTE BEI LIGAND-METALL-ELEKTRONENUEBERGAENGEN VON Cu(II)-CHELATEN DER α-DIKETO-BIS-THIOSEMICARBAZONE", J. inorg, nucl. Chem. 1978, Vol. 40, pages 631-634. *
CAS Registry Number 1207290-67-2; Entry Date 2010-02-24; (SP-4-4)-[2-[2-[2-[[(2-Aminoethyl)amino](thioxo-.kappa.S)methyl]hydrazinylidene-.kappa.N1]-1-methylpropylidene]-N-methylhydrazinecarbothioamide-.kappa.N2,.kappa.S]copper(2+) *
CAS Registry Number 53557-00-9; Entry Date 1984-11-16; Hydrazinecarbodithioic acid, 2-[2-[[[[2-(diethylamino)ethyl]amino]thioxomethyl]hydrazono]-1-methylpropylidene]-, methyl ester, copper complex *
COATS, E. A. et al., "Comparative Analysis of the Cytotoxicity of Substituted [Phenylglyoxal bis(4-methyl-3-thiosemicarbazone)]copper(II) Chelates", Journal of Medicinal Chemistry, 1976, vol. 19, no. 1, pages 131–135 *
COATS, E. A. et al., Journal of Medicinal Chemistry, 1978, vol. 21, no. 8, pages 804–809 *
DEARLING, J. L. J. et al., ‘Redox-active metal complexes for imaging hypoxic tissues: structure–activity relationships in copper(II) bis(thiosemicarbazone) complexes’, Chemical Communications. 1998, vol.22, pages 2531-2532 *
HALL, I. H. et al., "The Cytotoxicity of Symmetrical and Unsymmetrical Bis(thiosemicarbazones) and Their Metal Complexes in Murine and Human Tumor Cells", Arch. Pharm. Pharm. Med. Chem., 2000, vol. 333, pages 217–225 *
JOHN, E. K. et al., "Structure-Activity Relationships for Metal-Labeled Blood Flow Tracers: Comparison of Keto Aldehyde Bis(thiosemicarbazonato)copper(II) Derivatives", Journal of Medicinal Chemistry, 1990, vol. 33, no. 6, pages 1764–1770 *
SOON, C. P. W. et al., THE JOURNAL OF BIOLOGICAL CHEMISTRY, 2011, vol. 286, no. 51, pages 44035–44044 *

Also Published As

Publication number Publication date
IL272895A (en) 2020-04-30
WO2019046761A1 (en) 2019-03-07
AU2018325283A1 (en) 2020-03-12
JP2026041735A (ja) 2026-03-10
IL272895B2 (en) 2025-06-01
US20200188430A1 (en) 2020-06-18
EP3676271A1 (en) 2020-07-08
US12403159B2 (en) 2025-09-02
IL272895B1 (en) 2025-02-01
US20230172977A1 (en) 2023-06-08
US11596651B2 (en) 2023-03-07
JP2024001064A (ja) 2024-01-09
JP2020532538A (ja) 2020-11-12
CA3074258A1 (en) 2019-03-07
CN111278835A (zh) 2020-06-12

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