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
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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)
  • Medicinal Preparation (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (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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AU2018325283A Active AU2018325283B2 (en) 2017-09-01 2018-08-31 Therapeutic metal complexes and ligands and methods of making and using same

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US (2) US11596651B2 (enExample)
EP (1) EP3676271A1 (enExample)
JP (2) JP2020532538A (enExample)
CN (1) CN111278835A (enExample)
AU (1) AU2018325283B2 (enExample)
CA (1) CA3074258A1 (enExample)
IL (1) IL272895B2 (enExample)
WO (1) WO2019046761A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020532538A (ja) * 2017-09-01 2020-11-12 オレゴン ステイト ユニバーシティー 治療用金属錯体およびリガンドならびにその作成および使用の方法
BR112022001301A2 (pt) * 2019-07-25 2022-04-12 Als Therapy Development Inst Cuptsm para o tratamento de distúrbios neurodegenerativos
JP2023544965A (ja) 2020-08-26 2023-10-26 エイエルエス・セラピー・デヴェロップメント・インスティテュート 神経変性障害の治療のための銅錯体

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)

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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
AU2009326867B2 (en) * 2008-12-12 2015-10-29 The University Of Melbourne Process for the preparation of asymmetrical bis(thiosemicarbazones)
ES2778038T3 (es) * 2013-11-11 2020-08-07 Collaborative Medicinal Development Llc Complejos metálicos y métodos de tratamiento
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
JP2020532538A (ja) * 2017-09-01 2020-11-12 オレゴン ステイト ユニバーシティー 治療用金属錯体およびリガンドならびにその作成および使用の方法

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

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