Title:
テクネチウム-ビス(ヘテロアリール)錯体およびレニウム-ビス(ヘテロアリール)錯体、ならびにその使用方法
Document Type and Number:
Japanese Patent JP2007524685
Kind Code:
A
Abstract:
One aspect of the invention relates to complexes of a radionuclide with various heteroaryl ligands, e.g., imidazolyl and pyridyl ligands, and their use in radiopharmaceuticals for a variety of clinical diagnostic and therapeutic applications. Another aspect of the invention relates to imidazolyl and pyridyl ligands that form a portion of the aforementioned complexes. Methods for the preparation of the radionuclide complexes are also described. Another aspect of the invention relates to imidazolyl and pyridyl ligands based on derivatized lysine, alanine and bis-amino acids for conjugation to small peptides by solid phase synthetic methods. Additionally, the invention relates to methods for imaging regions of a mammal using the complexes of the invention.
Inventors:
Babitch John
Maresca Kevin Pee.
Chronouge James F. Jr.
Maresca Kevin Pee.
Chronouge James F. Jr.
Application Number:
JP2006553274A
Publication Date:
August 30, 2007
Filing Date:
February 14, 2005
Export Citation:
Assignee:
Molecular Insight Pharmaceuticals, Inc.
International Classes:
C07D213/36; A61K51/00; A61K51/04; C07D213/38; C07D233/54; C07D233/56; C07D233/64; C07D235/14; C07D235/20; C07D277/28; C07D401/12; C07D401/14; C07F1/08; C07F5/00; C07F13/00; C07D235/10
Domestic Patent References:
| JPH11342341A | 1999-12-14 | |||
| JP2003525282A | 2003-08-26 | |||
| JPS62207282A | 1987-09-11 | |||
| JPH09124479A | 1997-05-13 | |||
| JPH0862801A | 1996-03-08 | |||
| JPH04247067A | 1992-09-03 |
Foreign References:
| US4382872A | 1983-05-10 | |||
| WO2002077145A1 | 2002-10-03 | |||
| DE19713851A1 | 1998-10-08 | |||
| WO2003077727A2 | 2003-09-25 |
Other References:
YOUNG, R. C.; GANELLIN, C. R.; GRIFFITHS, R.; MITCHELL, R. C.; PARSONS, M. E.; SAUNDERS, D.; SORE, N: "An approach to the design of brain-penetrating histaminergic agonists", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 28(3), JPN6010074179, 1993, pages 201 - 11, ISSN: 0001812916
MANDAL, SUBRATA; MACIKENAS, DAINIUS; PROTASIEWICZ, JOHN D.; SAYRE, LAWRENCE M.: "Novel tert-Butyl Migration in Copper-Mediated Phenol Ortho-Oxygenation Implicates a Mechanism Involv", JOURNAL OF ORGANIC CHEMISTRY, vol. 65(16), JPN6010074189, 2000, pages 4804 - 4809, ISSN: 0001812922
MONZANI, ENRICO; BATTAINI, GIUSEPPE; PEROTTI, ANGELO; CASELLA, LUIGI; GULLOTTI, MICHELE; SANTAGOSTIN: "Mechanistic, Structural, and Spectroscopic Studies on the Catecholase Activity of a Dinuclear Copper", INORGANIC CHEMISTRY, vol. 38(23), JPN6010074190, 1999, pages 5359 - 5369, ISSN: 0001812923
MOSZNER, MONIKA; KWASKOWSKA-CHEC, EWA; WOLOWIEC, STANISLAW; JERZYKIEWICZ, LUCJAN B.; ZIOLKOWSKI, JO: "Neutral and Cationic Rhodium(III) Complexes with Tridentate Bis(benzimidazole)amine Ligands", JOURNAL OF CHEMICAL RESEARCH, SYNOPSES, vol. (11), JPN6010074191, 1999, pages 643 - 2727, ISSN: 0001812924
MONZANI, ENRICO; QUINTI, LUISA; PEROTTI, ANGELO; CASELLA, LUIGI; GULLOTTI, MICHELE; RANDACCIO, LUCIO: "Tyrosinase Models. Synthesis, Structure, Catechol Oxidase Activity, and Phenol Monooxygenase Activit", INORGANIC CHEMISTRY, vol. 37(3), JPN6010074192, 1998, pages 553 - 562, ISSN: 0001812925
WANG, JIANPING; MASHUTA, MARK S.; SUN, ZIMING; RICHARDSON, JOHN F.; HENDRICKSON, DAVID N.; BUCHANAN,: "Syntheses, Crystal Structures, and Properties of Unsymmetrical (μ-Oxo)diiron(III) Complexes Contain", INORGANIC CHEMISTRY, vol. 35(23), JPN6010074193, 1996, pages 6642 - 6643, ISSN: 0001812926
CASELLA, LUIGI; CARUGO, OLIVIERO; GULLOTTI, MICHELE; DOLDI, SERGIO; FRASSONI, MASSIMILIANO: "Synthesis, Structure, and Reactivity of Model Complexes of Copper Nitrite Reductase", INORGANIC CHEMISTRY, vol. 35(5), JPN6010074194, 1996, pages 1101 - 13, ISSN: 0001812927
NAKAO, YASUO; OONISHI, MAKOTO; UZU, TOMOKO; KASHIHARA, HIROKO; SUZUKI, SHINNICHIRO; SAKAI, MASAHIRO;: "Synthesis and properties of dinuclear copper(II) complexes containing dinucleating ligands with imid", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 67(9), JPN6010074195, 1994, pages 2586 - 9, ISSN: 0001812928
SORRELL, THOMAS N.; GARRITY, MARTHA L.: "Synthesis and reactivity of imidazolyl- and benzimidazolyl-containing copper complexes", INORGANIC CHEMISTRY, vol. 30(2), JPN6010074196, 1991, pages 210 - 15, ISSN: 0001812929
THOMPSON, LAURENCE K.; BALL, RICHARD G.; TROTTER, JAMES: "Complexes of substituted benzothiazoles. 2. Copper(II) complexes of the 'tripod' ligand tris(2-ben", CANADIAN JOURNAL OF CHEMISTRY, vol. 58(15), JPN6010074198, 1980, pages 1566 - 76, ISSN: 0001812930
BARTSCH, HERBERT; ERKER, THOMAS: "Chemistry of O,N- and S,N-heterocycles. X. Synthesis and biological activity of 2-substituted 2-et", ARCHIV DER PHARMAZIE (WEINHEIM, GERMANY), vol. 324(2), JPN6010074181, 1991, pages 79 - 82, ISSN: 0001812917
PANDIYAN,T. ET AL: "Structure, spectra and redox behavior of copper(II) complexes of bis(benzimidazolyl)diamine ligands", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS: INORGANIC CHEMISTRY(1972-1999), JPN6010074199, 1992, pages 3377 - 3384, ISSN: 0001812931
BANERJEE, SANGEETA RAY; WEI, LIHUI; LEVADALA, MURALI K.; LAZAROVA, NEVA; GOLUB, VLADIMIR O.; O'CONNO: "{ReIIICl3} Core Complexes with Bifunctional Single Amino Acid Chelates", INORGANIC CHEMISTRY, vol. 41(22), JPN6010074200, 2002, pages 5795 - 5802, ISSN: 0001812932
MITANI, AYAKO; ABE, MASAAKI; TSUGE, KIYOSHI; SASAKI, YOICHI: "η3-Coordination of hexadentate N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine (tpen) to a monon", CHEMISTRY LETTERS, vol. 32(6), JPN6010074201, 2003, pages 502 - 503, ISSN: 0001812933
BOTHA, J. MATTHEUS; UMAKOSHI, KEISUKE; SASAKI, YOICHI; LAMPRECHT, GERT J.: "Chelation Processes to an Oxorhenium(V) Center by N,N,N,O-Tetradentate and N,N,O-Tridentate Ligands", INORGANIC CHEMISTRY, vol. 37(7), JPN6010074202, 1998, pages 1609 - 1615, ISSN: 0001812934
BANERJEE, SANGEETA RAY; LEVADALA, MURALI K.; LAZAROVA, NEVA; WEI, LIHUI; VALLIANT, JOHN F.; STEPHENS: "Bifunctional Single Amino Acid Chelates for Labeling of Biomolecules with the {Tc(CO)3}+ and {Re(CO)", INORGANIC CHEMISTRY, vol. 41(24), JPN6010074183, 2002, pages 6417 - 6425, ISSN: 0001812918
CLEWLEY, R. G.; SLEBOCKA-TILK, H.; BROWN, R. S.: "Mono- and dinuclear M2+ chelates as catalysts for the hydrolysis of organophosphate triesters", INORGANICA CHIMICA ACTA, vol. 157(2), JPN6010074185, 1989, pages 233 - 8, ISSN: 0001812919
CHIU, YU-HUNG; CANARY, JAMES W.: "Stability and Acidity Constants for Ternary Ligand-Zinc-Hydroxo Complexes of Tetradentate Tripodal L", INORGANIC CHEMISTRY, vol. 42(17), JPN6010074187, 2003, pages 5107 - 5116, ISSN: 0001812920
MULLER-HARTMANN, ALEXANDRA; VAHRENKAMP, HEINRICH: "Zinc complexes of condensed phosphates, 4. Diphosphate-zinc complexes with encapsulating tripodal co", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. (11), JPN6010074188, 2000, pages 2371 - 2377, ISSN: 0001812921
MANDAL, SUBRATA; MACIKENAS, DAINIUS; PROTASIEWICZ, JOHN D.; SAYRE, LAWRENCE M.: "Novel tert-Butyl Migration in Copper-Mediated Phenol Ortho-Oxygenation Implicates a Mechanism Involv", JOURNAL OF ORGANIC CHEMISTRY, vol. 65(16), JPN6010074189, 2000, pages 4804 - 4809, ISSN: 0001812922
MONZANI, ENRICO; BATTAINI, GIUSEPPE; PEROTTI, ANGELO; CASELLA, LUIGI; GULLOTTI, MICHELE; SANTAGOSTIN: "Mechanistic, Structural, and Spectroscopic Studies on the Catecholase Activity of a Dinuclear Copper", INORGANIC CHEMISTRY, vol. 38(23), JPN6010074190, 1999, pages 5359 - 5369, ISSN: 0001812923
MOSZNER, MONIKA; KWASKOWSKA-CHEC, EWA; WOLOWIEC, STANISLAW; JERZYKIEWICZ, LUCJAN B.; ZIOLKOWSKI, JO: "Neutral and Cationic Rhodium(III) Complexes with Tridentate Bis(benzimidazole)amine Ligands", JOURNAL OF CHEMICAL RESEARCH, SYNOPSES, vol. (11), JPN6010074191, 1999, pages 643 - 2727, ISSN: 0001812924
MONZANI, ENRICO; QUINTI, LUISA; PEROTTI, ANGELO; CASELLA, LUIGI; GULLOTTI, MICHELE; RANDACCIO, LUCIO: "Tyrosinase Models. Synthesis, Structure, Catechol Oxidase Activity, and Phenol Monooxygenase Activit", INORGANIC CHEMISTRY, vol. 37(3), JPN6010074192, 1998, pages 553 - 562, ISSN: 0001812925
WANG, JIANPING; MASHUTA, MARK S.; SUN, ZIMING; RICHARDSON, JOHN F.; HENDRICKSON, DAVID N.; BUCHANAN,: "Syntheses, Crystal Structures, and Properties of Unsymmetrical (μ-Oxo)diiron(III) Complexes Contain", INORGANIC CHEMISTRY, vol. 35(23), JPN6010074193, 1996, pages 6642 - 6643, ISSN: 0001812926
CASELLA, LUIGI; CARUGO, OLIVIERO; GULLOTTI, MICHELE; DOLDI, SERGIO; FRASSONI, MASSIMILIANO: "Synthesis, Structure, and Reactivity of Model Complexes of Copper Nitrite Reductase", INORGANIC CHEMISTRY, vol. 35(5), JPN6010074194, 1996, pages 1101 - 13, ISSN: 0001812927
NAKAO, YASUO; OONISHI, MAKOTO; UZU, TOMOKO; KASHIHARA, HIROKO; SUZUKI, SHINNICHIRO; SAKAI, MASAHIRO;: "Synthesis and properties of dinuclear copper(II) complexes containing dinucleating ligands with imid", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 67(9), JPN6010074195, 1994, pages 2586 - 9, ISSN: 0001812928
SORRELL, THOMAS N.; GARRITY, MARTHA L.: "Synthesis and reactivity of imidazolyl- and benzimidazolyl-containing copper complexes", INORGANIC CHEMISTRY, vol. 30(2), JPN6010074196, 1991, pages 210 - 15, ISSN: 0001812929
THOMPSON, LAURENCE K.; BALL, RICHARD G.; TROTTER, JAMES: "Complexes of substituted benzothiazoles. 2. Copper(II) complexes of the 'tripod' ligand tris(2-ben", CANADIAN JOURNAL OF CHEMISTRY, vol. 58(15), JPN6010074198, 1980, pages 1566 - 76, ISSN: 0001812930
BARTSCH, HERBERT; ERKER, THOMAS: "Chemistry of O,N- and S,N-heterocycles. X. Synthesis and biological activity of 2-substituted 2-et", ARCHIV DER PHARMAZIE (WEINHEIM, GERMANY), vol. 324(2), JPN6010074181, 1991, pages 79 - 82, ISSN: 0001812917
PANDIYAN,T. ET AL: "Structure, spectra and redox behavior of copper(II) complexes of bis(benzimidazolyl)diamine ligands", JOURNAL OF THE CHEMICAL SOCIETY, DALTON TRANSACTIONS: INORGANIC CHEMISTRY(1972-1999), JPN6010074199, 1992, pages 3377 - 3384, ISSN: 0001812931
BANERJEE, SANGEETA RAY; WEI, LIHUI; LEVADALA, MURALI K.; LAZAROVA, NEVA; GOLUB, VLADIMIR O.; O'CONNO: "{ReIIICl3} Core Complexes with Bifunctional Single Amino Acid Chelates", INORGANIC CHEMISTRY, vol. 41(22), JPN6010074200, 2002, pages 5795 - 5802, ISSN: 0001812932
MITANI, AYAKO; ABE, MASAAKI; TSUGE, KIYOSHI; SASAKI, YOICHI: "η3-Coordination of hexadentate N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine (tpen) to a monon", CHEMISTRY LETTERS, vol. 32(6), JPN6010074201, 2003, pages 502 - 503, ISSN: 0001812933
BOTHA, J. MATTHEUS; UMAKOSHI, KEISUKE; SASAKI, YOICHI; LAMPRECHT, GERT J.: "Chelation Processes to an Oxorhenium(V) Center by N,N,N,O-Tetradentate and N,N,O-Tridentate Ligands", INORGANIC CHEMISTRY, vol. 37(7), JPN6010074202, 1998, pages 1609 - 1615, ISSN: 0001812934
BANERJEE, SANGEETA RAY; LEVADALA, MURALI K.; LAZAROVA, NEVA; WEI, LIHUI; VALLIANT, JOHN F.; STEPHENS: "Bifunctional Single Amino Acid Chelates for Labeling of Biomolecules with the {Tc(CO)3}+ and {Re(CO)", INORGANIC CHEMISTRY, vol. 41(24), JPN6010074183, 2002, pages 6417 - 6425, ISSN: 0001812918
CLEWLEY, R. G.; SLEBOCKA-TILK, H.; BROWN, R. S.: "Mono- and dinuclear M2+ chelates as catalysts for the hydrolysis of organophosphate triesters", INORGANICA CHIMICA ACTA, vol. 157(2), JPN6010074185, 1989, pages 233 - 8, ISSN: 0001812919
CHIU, YU-HUNG; CANARY, JAMES W.: "Stability and Acidity Constants for Ternary Ligand-Zinc-Hydroxo Complexes of Tetradentate Tripodal L", INORGANIC CHEMISTRY, vol. 42(17), JPN6010074187, 2003, pages 5107 - 5116, ISSN: 0001812920
MULLER-HARTMANN, ALEXANDRA; VAHRENKAMP, HEINRICH: "Zinc complexes of condensed phosphates, 4. Diphosphate-zinc complexes with encapsulating tripodal co", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. (11), JPN6010074188, 2000, pages 2371 - 2377, ISSN: 0001812921
Attorney, Agent or Firm:
Hatsushi Shimizu
Koichi Niimi
Koichi Niimi