WO1998043678A3 - Tetraaza- or n2s2- complexants, and their use in radiodiagnostics or radiotherapy - Google Patents

Tetraaza- or n2s2- complexants, and their use in radiodiagnostics or radiotherapy Download PDF

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Publication number
WO1998043678A3
WO1998043678A3 PCT/US1998/005858 US9805858W WO9843678A3 WO 1998043678 A3 WO1998043678 A3 WO 1998043678A3 US 9805858 W US9805858 W US 9805858W WO 9843678 A3 WO9843678 A3 WO 9843678A3
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Prior art keywords
radionuclide
present
compounds
cells
detecting
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PCT/US1998/005858
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French (fr)
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WO1998043678B1 (en
WO1998043678A2 (en
Inventor
Sudhakar Kasina
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Neorx Corp
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Publication date
Application filed by Neorx Corp filed Critical Neorx Corp
Priority to CA002284653A priority Critical patent/CA2284653C/en
Priority to DE69837038T priority patent/DE69837038T2/en
Priority to EP98912032A priority patent/EP0971748B1/en
Priority to JP54176898A priority patent/JP2002500629A/en
Publication of WO1998043678A2 publication Critical patent/WO1998043678A2/en
Publication of WO1998043678A3 publication Critical patent/WO1998043678A3/en
Publication of WO1998043678B1 publication Critical patent/WO1998043678B1/en

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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
    • C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic System
    • C07F13/005—Compounds without a metal-carbon linkage
    • 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
    • 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
    • A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
    • A61K51/0478—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group complexes from non-cyclic ligands, e.g. EDTA, MAG3
    • 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
    • A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
    • A61K51/0482—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group chelates from cyclic ligands, e.g. DOTA
    • 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
    • A61K51/0489—Phosphates or phosphonates, e.g. bone-seeking phosphonates
    • 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
    • A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
    • 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
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/087—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins the peptide being an annexin, e.g. annexin V
    • 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
    • A61K51/08—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins
    • A61K51/088—Peptides, e.g. proteins, carriers being peptides, polyamino acids, proteins conjugates with carriers being peptides, polyamino acids or proteins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/34—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a mercapto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/10—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
    • C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6524—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having four or more nitrogen atoms as the only ring hetero atoms
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
    • C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled

Abstract

The present invention provides for substituted metal chelating compounds in which at least two of the chelating atoms are nitrogen which are directly attached to aromatic rings and one or more of those nitrogen atoms has attached thereto a substituent other than hydrogen, and methods for making and using these compounds. Another aspect of the invention provides for the use of the chelation compounds described above in methods for diagnostic and therapeutic purposes. A diagnostic method is described for detecting the presence or absence of a target site within a mammalian host. This method comprises providing to cells a diagnostically effective dose of a compound of the present invention which contains a metal radionuclide, such as 99mTc and/or 111In, and detecting the biodistribution of the radionuclide. A therapeutic method is described for delivering a radionuclide, such as ?186Re/188Re, 90Y, and 153¿Sm, to a target site within a mammalian host. This method comprises providing to cells a therapeutically effective dose of a chelate compound of the present invention.
PCT/US1998/005858 1997-03-28 1998-03-26 Tetraaza- or n2s2- complexants, and their use in radiodiagnostics or radiotherapy WO1998043678A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002284653A CA2284653C (en) 1997-03-28 1998-03-26 Tetraaza- or n2s2- complexants, and their use in radiodiagnostics or radiotherapy
DE69837038T DE69837038T2 (en) 1997-03-28 1998-03-26 TETRAAZA OR N2S2 COMPLEXANTS, AND THEIR USE IN RADIODIAGNOSTICS OR RADIOTHERAPY
EP98912032A EP0971748B1 (en) 1997-03-28 1998-03-26 Tetraaza- or n2s2- complexants, and their use in radiodiagnostics or radiotherapy
JP54176898A JP2002500629A (en) 1997-03-28 1998-03-26 Tetraaza- or N2S2-complexant and its use in radiodiagnosis or radiotherapy

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/829,533 1997-03-28
US08/829,533 US6005083A (en) 1997-03-28 1997-03-28 Bridged aromatic substituted amine ligands with donor atoms

Publications (3)

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WO1998043678A2 WO1998043678A2 (en) 1998-10-08
WO1998043678A3 true WO1998043678A3 (en) 1999-03-04
WO1998043678B1 WO1998043678B1 (en) 1999-04-01

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PCT/US1998/005858 WO1998043678A2 (en) 1997-03-28 1998-03-26 Tetraaza- or n2s2- complexants, and their use in radiodiagnostics or radiotherapy

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US (7) US6005083A (en)
EP (2) EP1813607A3 (en)
JP (1) JP2002500629A (en)
CA (1) CA2284653C (en)
DE (1) DE69837038T2 (en)
ES (1) ES2281927T3 (en)
WO (1) WO1998043678A2 (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5965132A (en) 1992-03-05 1999-10-12 Board Of Regents, The University Of Texas System Methods and compositions for targeting the vasculature of solid tumors
US6005083A (en) * 1997-03-28 1999-12-21 Neorx Corporation Bridged aromatic substituted amine ligands with donor atoms
US6406693B1 (en) 1998-07-13 2002-06-18 Board Of Regents, The University Of Texas System Cancer treatment methods using antibodies to aminophospholipids
US6818213B1 (en) 1998-07-13 2004-11-16 Board Of Regents, The University Of Texas System Cancer treatment compositions comprising therapeutic conjugates that bind to aminophospholipids
EP2311490A3 (en) 1998-07-13 2011-05-04 Board of Regents, The University of Texas System Uses of antibodies to aminophospholipids for cancer treatment
WO2000002587A1 (en) 1998-07-13 2000-01-20 Board Of Regents, The University Of Texas System Cancer treatment methods using therapeutic conjugates that bind to aminophospholipids
US6239237B1 (en) * 1999-04-22 2001-05-29 Nova Chemicals (International) S.A. Group 8, 9 or 10 transition metal catalyst for olefin polymerization
AU5871000A (en) 1999-06-11 2001-01-02 Paul G. Abrams High dose radionuclide complexes for bone marrow suppression
US7094885B2 (en) 1999-07-11 2006-08-22 Neorx Corporation Skeletal-targeted radiation to treat bone-associated pathologies
US7067111B1 (en) 1999-10-25 2006-06-27 Board Of Regents, University Of Texas System Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging
US6565828B2 (en) 2000-04-07 2003-05-20 Bristol-Myers Squibb Company Macrocyclic chelants for metallopharmaceuticals
BRPI0111220B8 (en) 2000-06-02 2021-07-27 Univ Texas drug conjugates with ethylenedicysteine (ec)
JP2004536034A (en) 2001-01-08 2004-12-02 ネオルクス コーポレイション Therapeutic and diagnostic compounds, compositions and methods
ITRM20010079A1 (en) 2001-02-16 2002-08-16 Sigma Tau Ind Farmaceuti ADMINODERIVATES OF BIOTIN AND THEM CONJUGATED WITH MACROCYCLIC CHELANTS.
DE10125258A1 (en) * 2001-05-23 2003-01-09 November Ag Molekulare Medizin Method for determining the binding behavior of ligands that specifically bind to target molecules
US6890513B2 (en) 2001-05-25 2005-05-10 Mcmaster University Metal-carborane complexes for radioimaging and radiotherapy and methods for their preparation
WO2004002940A1 (en) * 2002-07-01 2004-01-08 Pharmacia & Upjohn Company Inhibitors of hcv ns5b polymerase
US9050378B2 (en) 2003-12-10 2015-06-09 Board Of Regents, The University Of Texas System N2S2 chelate-targeting ligand conjugates
US8758723B2 (en) 2006-04-19 2014-06-24 The Board Of Regents Of The University Of Texas System Compositions and methods for cellular imaging and therapy
US10925977B2 (en) 2006-10-05 2021-02-23 Ceil>Point, LLC Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5021571A (en) * 1989-06-29 1991-06-04 Associated Universities, Inc. Cyclohexyl EDTA monoanhydride
EP0603403A1 (en) * 1992-07-03 1994-06-29 The Green Cross Corporation Novel chelating agent, complex compound composed of said agent and metallic atom, and diagnostic agent containing said compound
US5334729A (en) * 1989-06-29 1994-08-02 Associated Universities, Inc. Stable radiometal antibody immunoconjugates
US5362475A (en) * 1981-07-24 1994-11-08 Schering Aktiengesellschaft Gadolinium chelates for magnetic resonance imaging
WO1994026754A1 (en) * 1993-05-06 1994-11-24 The Dow Chemical Company Bicyclopolyazamacrocyclophosphonic acids, their complexes and conjugates, for use as contrast agents, and processes for their preparation
WO1995032192A1 (en) * 1994-05-19 1995-11-30 Neorx Corporation Aromatic amine substituted bridged nitrogen and sulfur donor atom ligands for imaging
WO1997001360A2 (en) * 1995-06-26 1997-01-16 Concat, Ltd. Compounds with chelation affinity and selectivity for first transition series elements and their use in medical therapy and diagnosis
US5676928A (en) * 1994-03-28 1997-10-14 Nycomed Imaging As Liposomes
WO1998004294A2 (en) * 1996-07-26 1998-02-05 Neorx Corporation Radiolabeled annexins

Family Cites Families (100)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2977279A (en) * 1955-11-29 1961-03-28 Monsanto Chemicals Copper chelate coordination complexes
US3027391A (en) * 1959-08-28 1962-03-27 Norman A Frigerio Metal phthalocyanines
US4088747A (en) * 1975-02-19 1978-05-09 Australian Atomic Energy Commission Phenolic amino-carboxylic acid radiopharmaceuticals
DE2616984C3 (en) * 1976-04-17 1981-10-29 Behringwerke Ag, 3550 Marburg Method for the isolation and purification of a placenta-specific glycoprotein
JPS5486602A (en) * 1977-10-27 1979-07-10 Hoffmann La Roche Production of purified alpha 1 phetoprotein
US4293537A (en) * 1978-09-05 1981-10-06 Wong Dennis W Novel chemical method of labeling proteins with 99m Tc-Technetium at physiological condition
JPS567725A (en) * 1979-06-28 1981-01-27 Daiichi Rajio Isotope Kenkyusho:Kk Tumor scanning agent
US4421735A (en) * 1980-04-17 1983-12-20 The Massachusetts General Hospital Radiolabeled diagnostic compositions and method for making the same
US4385046A (en) * 1980-12-15 1983-05-24 Minnesota Mining And Manufacturing Company Diagnostic radio-labeled polysaccharide derivatives
US5648063A (en) * 1981-07-24 1997-07-15 Schering Aktiengesellschaft Sterile composition comprising a chelate complex for magnetic resonance imaging
US4452774A (en) * 1982-04-30 1984-06-05 President And Fellows Of Harvard College Isonitrile radionuclide complexes for labelling and imaging agents
DE3228503A1 (en) * 1982-07-30 1984-02-02 Behringwerke Ag, 3550 Marburg NEW PROTEIN (PP (DOWN ARROW) 1 (DOWN ARROW) (DOWN ARROW) 7 (DOWN ARROW)), METHOD FOR ITS ENHANCEMENT AND PRODUCTION AND USE
US4758682A (en) * 1983-03-17 1988-07-19 California Institute Of Technology Homogeneous coordination compounds as oxidation catalysts
DE3315000A1 (en) * 1983-04-26 1984-10-31 Behringwerke Ag, 3550 Marburg TISSUE PROTEIN PP (DOWN ARROW) 4 (DOWN ARROW), METHOD FOR ITS RECOVERY AND USE
US4515767A (en) * 1983-06-20 1985-05-07 The Dow Chemical Company Radioactive metals complexed with phosphonate derivatives of dicyclopentadienebis(methylamine)
US4673562A (en) * 1983-08-19 1987-06-16 The Children's Medical Center Corporation Bisamide bisthiol compounds useful for making technetium radiodiagnostic renal agents
US4560548A (en) * 1984-04-10 1985-12-24 The Dow Chemical Company Bone seeking Tc-99m complexes of phosphonate derivatives of bis(aminoalkyl)piperazine
EP0163294A2 (en) * 1984-06-01 1985-12-04 E.I. Du Pont De Nemours And Company Soluble copper salt containing composition useful for forming technetium labelled radiodiagnostic agents
US5064633A (en) * 1984-06-04 1991-11-12 The Dow Chemical Company Macrocyclic aminophosphonic acid complexes, their formulations and use
US4898724A (en) * 1984-06-04 1990-02-06 The Dow Chemical Company Organis amine phosphonic acid complexes for the treatment of calcific tumors
US5059412A (en) * 1984-06-04 1991-10-22 The Dow Chemical Company Macrocyclic aminophosphonic acid complexes for the treatment of calcific tumors
US5066478A (en) * 1984-06-04 1991-11-19 The Dow Chemical Company Radio labeled organic amine phosphonic acid complexes for the treatment of calcific tumors
US4963688A (en) * 1984-07-19 1990-10-16 University Of Florida Compounds for site-enhanced delivery of radionuclides and uses thereof
US4963682A (en) * 1984-07-19 1990-10-16 University Of Florida Novel radiopharmaceuticals and chelating agents useful in their preparation
US4722892A (en) * 1984-08-31 1988-02-02 Meares Claude F Monoclonal antibodies against metal chelates
US4897254A (en) * 1984-09-21 1990-01-30 The Dow Chemical Company Radioactive compositions for the treatment of calcific tumors
GB8426845D0 (en) * 1984-10-24 1984-11-28 Amersham Int Plc Complexes of technetium-99m
US5019497A (en) * 1984-11-09 1991-05-28 Lennart Olsson Human squamous lung carcinoma cell specific antigens and antibodies
US5037630A (en) * 1985-01-14 1991-08-06 Neorx Corporation Metal radionuclide labeled proteins for diagnosis and therapy
US4897255A (en) * 1985-01-14 1990-01-30 Neorx Corporation Metal radionuclide labeled proteins for diagnosis and therapy
US5120526A (en) * 1985-01-14 1992-06-09 Neorx Corporation Method of producing metal radionuclide labeled proteins for diagnosis and therapy
US5175343A (en) * 1985-01-14 1992-12-29 Neorx Corporation Metal radionuclide labeled proteins for diagnosis and therapy
US5242679A (en) * 1985-01-14 1993-09-07 Neorx Corporation Metal radionuclide labeled proteins for diagnosis and therapy
EP0194843B1 (en) * 1985-03-11 1993-01-13 AMERSHAM INTERNATIONAL plc Complexes of technetium-99m with propylene amine oximes
US4746505A (en) * 1985-04-26 1988-05-24 President And Fellows Of Harvard College Technetium radiodiagnostic fatty acids derived from bisamide bisthiol ligands
EP0200211A1 (en) * 1985-05-01 1986-11-05 The Research Foundation Of State University Of New York Diagnostic radiopharmaceutical compounds
US5225181A (en) * 1985-06-07 1993-07-06 The Research Foundation Of State University Of New York Radiolabeled antiplatelet monoclonal antibody for imaging in-vivo thrombi
US4831122A (en) * 1986-01-09 1989-05-16 Regents Of The University Of Minnesota Radioimmunotoxins
US5271927A (en) * 1986-02-13 1993-12-21 Celltech Limited Antibody conjugates with macrocyclic ligands
US4732974A (en) * 1986-03-05 1988-03-22 Mallinckrodt, Inc. Metal ion labeling of carrier molecules
US4877868A (en) * 1986-03-12 1989-10-31 Neorx Corporation Radionuclide antibody coupling
US4861869A (en) * 1986-05-29 1989-08-29 Mallinckrodt, Inc. Coupling agents for joining radionuclide metal ions with biologically useful proteins
US4863713A (en) * 1986-06-23 1989-09-05 The Board Of Trustees Of Leland Stanford Jr. Univ. Method and system for administering therapeutic and diagnostic agents
US4859431A (en) 1986-11-10 1989-08-22 The Curators Of The University Of Missouri Rhenium generator system and its preparation and use
DE3789432T2 (en) * 1986-12-30 1994-10-06 Nihon Mediphysics Co Ltd High molecular compound, consisting of a unit of a compound that leads to the asialoglycoprotein acceptor and a unit of a chelating compound that is chemically bound to it, and their use.
US5279811A (en) * 1987-02-18 1994-01-18 The Du Pont Merck Pharmaceutical Company Ester-substituted diaminedithiols and radiolabeled complexes thereof
US5091514A (en) * 1987-03-26 1992-02-25 Neorx Corporation Metal-radionuclide-labeled proteins and glycoproteins for diagnosis and therapy
AR246956A1 (en) * 1987-05-08 1994-10-31 Salutar Inc Dipyridoxyl phosphate nuclear magnetic resonance imagery contrast agents
US4853209A (en) * 1987-05-18 1989-08-01 The Dow Chemical Company Bone marrow suppressing agents
WO1989001342A2 (en) * 1987-08-07 1989-02-23 Mallinckrodt, Inc. Diagnostic or radiotherapeutic composition comprising a hydrogen containing compound
ATE89271T1 (en) * 1987-11-19 1993-05-15 Univ Vanderbilt RADIOIODIUM-CONTAINING BENZAMIDES AND METHODS OF USE AS RADIOGENIC AGENTS.
US5322678A (en) * 1988-02-17 1994-06-21 Neorx Corporation Alteration of pharmacokinetics of proteins by charge modification
EP0329184A3 (en) * 1988-02-19 1990-05-23 Neorx Corporation Antimers and antimeric conjugation
US5112954A (en) * 1988-02-26 1992-05-12 Neorx Corporation Method of enhancing the effect of cytotoxic agents
US5061641A (en) * 1988-04-01 1991-10-29 Immunomedics, Inc. Method for radiolabeling proteins
US5057301A (en) * 1988-04-06 1991-10-15 Neorx Corporation Modified cellular substrates used as linkers for increased cell retention of diagnostic and therapeutic agents
US5059541A (en) * 1988-04-29 1991-10-22 Neorx Corporation Minimal derivatization of proteins
US5075099A (en) * 1988-05-31 1991-12-24 Neorx Corporation Metal radionuclide chelating compounds for improved chelation kinetics
CA1340527C (en) * 1988-05-31 1999-05-04 Lidia Vallarino Macrocyclic complexes of yttrium, the lanthanides and the actinides having peripheral coupling functionalities
US5089249A (en) * 1988-06-10 1992-02-18 Neorx Corporation Conjugates for bone imaging and bone cancer therapy
US5002754A (en) * 1988-06-15 1991-03-26 University Of Cincinnati Technetium (III/II) imaging agents
US5071965A (en) * 1988-07-19 1991-12-10 Mallinckrodt Medical, Inc. Novel tc-99m complexes
US5169933A (en) * 1988-08-15 1992-12-08 Neorx Corporation Covalently-linked complexes and methods for enhanced cytotoxicity and imaging
US5252713A (en) * 1988-09-23 1993-10-12 Neorx Corporation Polymeric carriers for non-covalent drug conjugation
US4987227A (en) * 1988-10-21 1991-01-22 The Research Foundation Of State University Of New York Polyazamacrocycles and their metal complexes
US4925650A (en) * 1988-11-16 1990-05-15 Mallinckrodt, Inc. Technetium -99m complex for examining the renal function
US4976950A (en) * 1988-12-19 1990-12-11 The Dow Chemical Company Bone marrow suppressing agents
US5053503A (en) * 1989-02-17 1991-10-01 Centocor Chelating agents
US4959304A (en) * 1989-05-22 1990-09-25 United States Of America As Represented By The Secretary Of The Navy Production of monoclonal antibodies to treponema denticola by hybridoma TDIII, IIIBB2
US5250666A (en) * 1989-06-16 1993-10-05 Neorx Corporation Radionuclide metal chelates for the radiolabeling of proteins
US5164176A (en) * 1989-06-16 1992-11-17 Neorx Corporation Radionuclide metal chelates for the radiolabeling of proteins
DE3930674A1 (en) * 1989-09-11 1991-03-21 Diagnostikforschung Inst BIFUNCTIONAL CHELATE FORMERS FOR COMPLEXING TC AND RE-ISOTOPES, METHOD FOR THE PRODUCTION AND DISPLAY OF CONJUGATES THEREOF AND THEIR USE IN DIAGNOSTICS AND THERAPY
US5053186A (en) 1989-10-02 1991-10-01 Neorx Corporation Soluble irradiation targets and methods for the production of radiorhenium
US5080884A (en) * 1989-12-12 1992-01-14 Medi-Physics, Inc. Hydrocarbylphenyl diaminodithiol radionuclide complexes and their use in imaging
US5026913A (en) * 1989-12-12 1991-06-25 Medi-Physics, Inc. Hydrocarbylphenyl diaminodithiol derivatives
EP0432988B1 (en) * 1989-12-12 1994-02-16 AMERSHAM INTERNATIONAL plc Hydrocarbylphenyl diaminodithiol derivatives
US5175257A (en) * 1989-12-29 1992-12-29 Neorx Corporation Radiolabeled proteins for diagnostic or therapeutic use
US5112953A (en) * 1989-12-29 1992-05-12 Neorx Corporation Radiolabeled proteins for diagnostic or therapeutic use
US5079346A (en) * 1990-05-01 1992-01-07 Trustees Of The University Of Pennsylvania Gallium-labelled imaging agents
US5286848A (en) * 1990-05-07 1994-02-15 Hamamatsu Photonics K.K. Lanthanide cryptate of trisphenanthroline
KR100272077B1 (en) 1990-08-29 2000-11-15 젠팜인터내셔날,인코포레이티드 Transgenic non-human animals capable of producing heterologous antibodies
US5382654A (en) * 1992-02-05 1995-01-17 Mallinckrodt Medical, Inc. Radiolabelled peptide compounds
US5104638A (en) * 1990-10-29 1992-04-14 Mallinckrodt Medical, Inc. Method of making a radiopharmaceutical complex from a kit
US5116598A (en) * 1990-10-29 1992-05-26 Mallinckrodt Medical, Inc. N4 technetium-99 m complexes for use as radiopharmaceuticals
US5243073A (en) * 1990-12-14 1993-09-07 Mallinckrodt Medical, Inc. Hexadentate ligands useful in radiographic imaging agents
US5112594A (en) * 1991-04-04 1992-05-12 Mallinckrodt Medical, Inc. Kit for preparing a technetium-99m myocardial imaging agent
US5112595A (en) * 1990-12-21 1992-05-12 Mallinckrodt Medical, Inc. 99MTC(III) myocardial imaging agents and method of use
US5133956A (en) * 1991-05-30 1992-07-28 The Dow Chemical Company Radiolabeled metal-binding protein for the treatment of arthritis
IT1248361B (en) 1991-06-28 1995-01-05 Enea PLASMIDIC VECTORS FOR THE EXPRESSION OF GENES IN PLANTS
US5330737A (en) * 1991-12-06 1994-07-19 Mallinckrodt Medical, Inc. Nitrogen-sulfur ligands as opiate receptor drug mimics
US5220000A (en) * 1992-01-23 1993-06-15 Spyros Theodoropulos Bifunctional-bis-quinolinols, and their metal chelates
AU3606793A (en) * 1992-02-05 1993-09-03 Mallinckrodt Medical, Inc. Radiolabelled peptide compounds
US5371184A (en) * 1992-02-05 1994-12-06 Mallinckrodt Medical, Inc. Radiolabelled peptide compounds
US5310536A (en) * 1992-02-06 1994-05-10 Mallinckrodt Medical, Inc. Ligands for improving metal chelate formation kinetics
US5324502A (en) * 1992-04-02 1994-06-28 Purdue Research Foundation Radiopharmaceuticals for imaging the heart
US5319143A (en) * 1992-07-31 1994-06-07 Polaroid Corporation Bis(aminoethanethiols)
US5476644A (en) * 1994-04-13 1995-12-19 Sterling Winthrop Inc. Cyclic triamine chelating agents
CA2190727C (en) * 1994-05-19 2006-07-18 Sudhakar Kasina Aromatic amine substituted bridged nitrogen and sulfur donor atom ligands for imaging
US5508458A (en) * 1995-05-26 1996-04-16 Hoechst Celanese Corporation Chiral catalysts and processes for preparing the same
US6005083A (en) * 1997-03-28 1999-12-21 Neorx Corporation Bridged aromatic substituted amine ligands with donor atoms

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5362475A (en) * 1981-07-24 1994-11-08 Schering Aktiengesellschaft Gadolinium chelates for magnetic resonance imaging
US5021571A (en) * 1989-06-29 1991-06-04 Associated Universities, Inc. Cyclohexyl EDTA monoanhydride
US5334729A (en) * 1989-06-29 1994-08-02 Associated Universities, Inc. Stable radiometal antibody immunoconjugates
EP0603403A1 (en) * 1992-07-03 1994-06-29 The Green Cross Corporation Novel chelating agent, complex compound composed of said agent and metallic atom, and diagnostic agent containing said compound
WO1994026754A1 (en) * 1993-05-06 1994-11-24 The Dow Chemical Company Bicyclopolyazamacrocyclophosphonic acids, their complexes and conjugates, for use as contrast agents, and processes for their preparation
US5676928A (en) * 1994-03-28 1997-10-14 Nycomed Imaging As Liposomes
WO1995032192A1 (en) * 1994-05-19 1995-11-30 Neorx Corporation Aromatic amine substituted bridged nitrogen and sulfur donor atom ligands for imaging
WO1997001360A2 (en) * 1995-06-26 1997-01-16 Concat, Ltd. Compounds with chelation affinity and selectivity for first transition series elements and their use in medical therapy and diagnosis
WO1998004294A2 (en) * 1996-07-26 1998-02-05 Neorx Corporation Radiolabeled annexins

Non-Patent Citations (26)

* Cited by examiner, † Cited by third party
Title
"Indium-111", REYNOLDS J E F (ED ): MARTINDALE - THE EXTRA PHARMACOPOEIA, ED. 31, 1996, Royal Pharmaceutical Society, London, GB, pages 1465, XP002074823 *
"Rhenium-186, Samarium-153, Technetium-99m, Yttrium-90", REYNOLDS J E F (ED ): MARTINDALE - THE EXTRA PHARMACOPOEIA, ED. 31, 1996, Royal Pharmaceutical Society, London, GB, pages 1467 - 1468, XP002074822 *
43RD ANNUAL MEETING OF THE SOCIETY OF NUCLEAR MEDICINE, DENVER, COLORADO, USA, JUNE 3-5, 1996 *
44TH ANNUAL MEETING OF THE SOCIETY OF NUCLEAR MEDICINE, SAN ANTONIO, TEXAS, USA, JUNE 1-5, 1997 *
5TH INTERNATIONAL SYMPOSIUM ON RADIOPHARMACEUTICAL CHEMISTRY, TOKYO, JAPAN, JULY 9-13, 1984 *
BLANKENBERG F G ET AL: "Increased localization of Tc-99m hydrazino nicotinamide (HYNIC) labeled annexin V lipocortin in lymphatic tissue of animals treated with dexamethasone", JOURNAL OF NUCLEAR MEDICINE, 1997, VOL. 38, NO. 5 SUPPL., PAGE(S) 268P-269P., XP002084594 *
DEWANJEE M.K.: "Localization of 113m-In- and 67-Ga-labeled poly- methylene- phosphonates in myocardial infarct", NUKL. MED., 1977, VOL. 16, NO. 4, PAGE(S) 151-156, XP002084588 *
GOECKELER W.F. ET AL: "Skeletal localization of samarium-153 chelates: Potential therapeutic bone agents", J. NUCL. MED., 1987, VOL. 28, NO. 4, PAGE(S) 495-504, XP002084591 *
KASINA S ET AL: "Preformed chelate Tc-99m radiolabeling of r-annexin V for arterial thrombus imaging", JOURNAL OF NUCLEAR MEDICINE, 1996, VOL. 37, NO. 5 SUPPL., PAGE(S) 29P., XP002084593 *
LEVER S Z ET AL: "PULMONARY ACCUMULATION OF NEUTRAL DIAMINE DITHIOL COMPLEXES OF TECHNETIUM-99M", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 83, no. 6, 1 June 1994 (1994-06-01), pages 802 - 809, XP000446373 *
LOUW W K A ET AL: "Evaluation of Samarium-153 and Holmium-166-EDTMP in the Normal Baboon Model", NUCLEAR MEDICINE AND BIOLOGY, vol. 23, no. 8, November 1996 (1996-11-01), pages 935-940, XP004073001 *
PAPADOPOULOS M ET AL: "99MTC-DADT COMPLEXES SUBSTITUTED WITH HETEROCYCLIC AMINES: EFFECT OF SUBSTITUTION ON IN VIVO REACTIVITY", NUCLEAR MEDICINE AND BIOLOGY, vol. 20, no. 1, 1 January 1993 (1993-01-01), pages 105 - 115, XP000336597 *
RENN O ET AL: "New approaches to delivering metal-labeled antibodies to tumors: Synthesis and characterization of new biotinyl chelate conjugates for pre-targeted diagnosis and therapy", JOURNAL OF CONTROLLED RELEASE, vol. 39, no. 2, May 1996 (1996-05-01), pages 239-249, XP004037330 *
S. BUDAVARI ET AL.: "THE MERCK INDEX, AN ENCYCLOPEDIA OF CHEMICALS, DRUGS, AND BIOLOGICALS", 1996, MERCK & CO, INC, WHITEHOUSE STATION, US, XP002074824 *
SCHOMACKER K ET AL: "[The effect of ethylenediaminetetramethylenephosphonate on the biodistribution of tumor-seeking radionuclides]", NUKLEARMEDIZIN, FEB 1993, VOL. 32, NO. 1, PAGE(S) 23-6, XP002084587 *
SCHOMACKER K ET AL: "Influence on extratumoral organ activities of tumor-affinity samarium-153 preparations]", NUKLEARMEDIZIN, MAR 1997, VOL. 36, NO. 2, PAGE(S) 47-51, XP002084586 *
STAHL W ET AL: "99m Technetium labelling of antibodies using methylphosphonylated, bifunctional cyclams as chelators", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, VOL. 4, NO. 21, PAGE(S) 2597-2600., XP002084592 *
STRATTON J R ET AL: "SELECTIVE UPTAKE OF RADIOLABELED ANNEXIN V ON ACUTE PORCINE LEFT ATRIAL THROMBI", CIRCULATION, vol. 92, no. 10, 15 November 1995 (1995-11-15), pages 3113 - 3121, XP002058828 *
SUBRAMANIAN G ET AL: "Indium-113m-labeled polyfunctional phosphonates as bone-imaging agents.", J NUCL MED, NOV 1975, VOL. 16, NO. 11, PAGE(S) 1080-4, XP002084585 *
SUBRAMANIAN K M ET AL: "A NEW RADIOCHEMICAL METHOD TO DETERMINE THE STABILITY CONSTANTS OF METAL CHELATES ATTACHED TO A PROTEIN", JOURNAL OF NUCLEAR MEDICINE, vol. 31, no. 4, 1 April 1990 (1990-04-01), pages 480 - 488, XP000128746 *
SUN Y: "TARGETING RADIOPHARMACEUTICALS-II. EVALUATION OF NEW TRIVALENT METAL COMPLEXES WITH DIFFERENT OVERALL CHARGES", INTERNATIONAL JOURNAL OF RADIATION APPLICATIONS AND INSTRUMENTATION PART B: NUCLEAR MEDICINE AND BIOLOGY, vol. 18, no. 3, 1 January 1991 (1991-01-01), pages 323 - 330, XP000215616 *
TADASHI FUJISAWA ET AL: "CRITICAL CURRENT DENSITIES IN SUPERCONDUCTING Y-BA-CU-O PREPARED BY CHELATING METHOD", JAPANESE JOURNAL OF APPLIED PHYSICS, vol. 29, no. 10, 1 October 1990 (1990-10-01), pages 1914 - 1917, XP000223980 *
TSIEN R Y: "New calcium indicators and buffers with high selectivity against magnesium and protons: design, synthesis, and properties of prototype structures", BIOCHEMISTRY 1980, VOL. 19, NO. 11, PAGE(S) 2396-2404, XP002074821 *
VOLKERT W A ET AL: "SKELETAL UPTAKE PROPERTIES OF TECHNETIUM-99M-LABELED MULTIDENTATE PHOSPHONATE LIGANDS", J LABELLED COMPD RADIOPHARM, 1984, VOL. 21, NO. 11-12, PAGE(S) 1063-1065, XP002084589 *
VOLKERT W.A. ET AL: "In vivo skeletal localization properties of 99m-Tc complexes of large phosphonate ligands", NUCL. MED. BIOL., 1986, VOL. 13, NO. 1, PAGE(S) 31-37, XP002084590 *
WU C ET AL: "INVESTIGATIONS OF N-LINKED MACROCYCLES FOR 111IN AND 90Y LABELING OF PROTEINS", INTERNATIONAL JOURNAL OF RADIATION APPLICATIONS AND INSTRUMENTATION PART B: NUCLEAR MEDICINE AND BIOLOGY, vol. 19, no. 2, 1992, pages 239 - 244, XP002064857 *

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