Title:
PREPARATION OF M(CO)3-COMPLEXES BY SOLID PHASE TECHNIQUES VIA METAL ASSISTED CLEAVAGE FROM THE SOLID SUPPORT
Document Type and Number:
WIPO Patent Application WO2004022105
Kind Code:
A3
Abstract:
The present invention relates to a process for generating a water soluble metal complexed agent, comprising contacting a solid phase bound organic conjugate represented by the formula I with [M(H2O)3(CO)3], under suitable conditions to cause the formation of a coordinate bond between [M(H2O)3(CO)3] and the tertiary amine nitrogen atom of the solid phase bound organic conjugate and thereby the release of the metal complexed agent thus formed from the support. The invention further relates to the conjugate of formula (I) and to a kit for performing the process.
Inventors:
ALBERTO ROGER (CH)
MUNDWILER STEFAN (CH)
MUNDWILER STEFAN (CH)
Application Number:
PCT/US2003/027665
Publication Date:
April 22, 2004
Filing Date:
September 02, 2003
Export Citation:
Assignee:
MALLINCKRODT INC (US)
ALBERTO ROGER (CH)
MUNDWILER STEFAN (CH)
ALBERTO ROGER (CH)
MUNDWILER STEFAN (CH)
International Classes:
A61K47/48; A61K51/04; A61K51/12; C07F1/08; C07F13/00; C07F15/00; (IPC1-7): A61K51/04; A61K51/12; C07F1/08; C07F13/00; C07F15/00
Domestic Patent References:
| WO2001089586A2 | 2001-11-29 | |||
| WO2001000637A1 | 2001-01-04 | |||
| WO1998048848A1 | 1998-11-05 | |||
| WO2001025243A1 | 2001-04-12 |
Foreign References:
| EP1013642A2 | 2000-06-28 | |||
| US5789555A | 1998-08-04 |
Other References:
SCHIBLI R ET AL: "Steps toward high specific activity labelling of biomolecules for therapeutic application: preparation of precursor [[188]Re(H2O)3(CO)3]+ and synthesis of tailor-made bifunctional ligand systems", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 13, no. 4, 7 July 2002 (2002-07-07), pages 750 - 756, XP002218738, ISSN: 1043-1802
LA BELLA R ET AL: "A [99m]Tc(I)-postlabelled high affinity bombesin analogue as a potential tumor imaging agent", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 13, no. 3, 15 May 2002 (2002-05-15), pages 599 - 604, XP002218739, ISSN: 1043-1802
JANG B-S ET AL: "Synthesis of [99m]Tc-tricarbonyl precursors for labelling of bioactive molecules", JOURNAL OF THE KOREAN NUCLEAR SOCIETY, vol. 34, no. 2, April 2002 (2002-04-01), pages 146 - 153, XP001117823, ISSN: 0372-7327
LANGER M ET AL: "[99m]Tc-labelled neuropeptide Y analogues as potential tumour imaging agents", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 12, November 2001 (2001-11-01), pages 1028 - 1034, XP001059452, ISSN: 1043-1802
SEIFERT S ET AL: "REACTIVITY OF TECHNETIUM(I) THIOETHER CARBONYL COMPLEXES TOWARDS HISTIDINE-AN EXAFS STUDY IN SOLUTION", INORGANICA CHIMICA ACTA, LAUSANNE, CH, vol. 322, 8 October 2001 (2001-10-08), pages 79 - 86, XP001074703, ISSN: 0020-1693
CORREIA J D G ET AL: "Re Tricarbonyl Complexes with Ligands Containing P,N,N and P,N,O Donor Atom Sets: Synthesis and Structural Characterisation", INORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 40, no. 20, 24 September 2001 (2001-09-24), pages 5147 - 65151, XP002218740, ISSN: 0020-1669
PETRIG J ET AL: "Derivatisation of glucose and 2-deoxyglucose for transition metal complexation: substitution reactions with organometallic [99m]Tc and Re precursors and fundamental NMR investigations", CHEMISTRY - A EUROPEAN JOURNAL, WILEY-VCH, WEILHEIM, DE, vol. 7, no. 9, 4 May 2001 (2001-05-04), pages 1866 - 1873, XP002218741, ISSN: 0947-6539
FALLER J W ET AL: "The synthesis of new complexes of rhenium(I) with heterotridentate [P,N,O] ligands", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 626, no. 1-2, 30 April 2001 (2001-04-30), pages 181 - 185, XP004235661, ISSN: 0022-328X
SCHIBLI R ET AL: "Influence of the denticity of ligand systems on the in vitro and in vivo behaviour of [99m]Tc(I)-tricarbonyl complexes: a hint for the future functionalisation of biomolecules", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 11, no. 3, May 2000 (2000-05-01), pages 345 - 351, XP002218742, ISSN: 1043-1802
POLLAK A ET AL: "A convenient method of preparing high specific activity technetium complexes using thiol-containing chelators absorbed on gold", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 121, no. 49, 15 December 1999 (1999-12-15), pages 11593 - 11594, XP002218743, ISSN: 0002-7863
ALBERTO ET AL: "A Novel Organometallic Aqua Complex of Technetium for the Labeling of Biomolecules: Synthesis of [99mTc(OH2)3(CO)3]+ from [99mTcO4]- in Aqueous Solution and Its Reaction with a Bifunctional Ligand", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 120, no. 31, 12 August 1998 (1998-08-12), pages 7987 - 7988, XP002149527, ISSN: 0002-7863
STOR G J ET AL: "Spectroelectrochemical (IR, UV/Vis) determination of the reductive pathways for a series of [Re(CO)3(alpha-diimine)L']0/+ (L' = Halide, Otf-, THF, MeCN, n-PrCN, PPh3, P(OMe)3) complexes", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 14, no. 3, March 1995 (1995-03-01), pages 1115 - 1131, XP002218744, ISSN: 0276-7333
ALBERTO R ET AL: "New organometallic technetium complexes in high and low oxidation states", RADIOCHIMICA ACTA, LONDON, GB, vol. 63, 1993, pages 153 - 161, XP002060831
DUNN-DUFAULT R ET AL: "A solid-phase technique for preparation of no-carrier-added technetium-99m radiopharmaceuticals: application to the streptavidin/biotin system", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, vol. 27, no. 8, November 2000 (2000-11-01), pages 803 - 807, XP004228484, ISSN: 0969-8051
KHEHYONG N ET AL: "Preparation of Acid-labile Resins with Halide Linkers and their Utility in Solid Phase Organic Synthesis", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 38, no. 6, 10 February 1997 (1997-02-10), pages 973 - 976, XP004033909, ISSN: 0040-4039
VAN WIJNKOOP M ET AL: "1,3-Dipolar cycloaddition reactions to the C=X-M fragment. 7. Reaction of Ru(CO)3(i-Pr-DAB) with dimethyl acetylenedicarboxylate. X-ray crystal structure of the protonated initial bicyclo[2.2.1] adduct", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 11, no. 11, November 1992 (1992-11-01), pages 3607 - 3617, XP002218745, ISSN: 0276-7333
LA BELLA R ET AL: "A [99m]Tc(I)-postlabelled high affinity bombesin analogue as a potential tumor imaging agent", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 13, no. 3, 15 May 2002 (2002-05-15), pages 599 - 604, XP002218739, ISSN: 1043-1802
JANG B-S ET AL: "Synthesis of [99m]Tc-tricarbonyl precursors for labelling of bioactive molecules", JOURNAL OF THE KOREAN NUCLEAR SOCIETY, vol. 34, no. 2, April 2002 (2002-04-01), pages 146 - 153, XP001117823, ISSN: 0372-7327
LANGER M ET AL: "[99m]Tc-labelled neuropeptide Y analogues as potential tumour imaging agents", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 12, November 2001 (2001-11-01), pages 1028 - 1034, XP001059452, ISSN: 1043-1802
SEIFERT S ET AL: "REACTIVITY OF TECHNETIUM(I) THIOETHER CARBONYL COMPLEXES TOWARDS HISTIDINE-AN EXAFS STUDY IN SOLUTION", INORGANICA CHIMICA ACTA, LAUSANNE, CH, vol. 322, 8 October 2001 (2001-10-08), pages 79 - 86, XP001074703, ISSN: 0020-1693
CORREIA J D G ET AL: "Re Tricarbonyl Complexes with Ligands Containing P,N,N and P,N,O Donor Atom Sets: Synthesis and Structural Characterisation", INORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 40, no. 20, 24 September 2001 (2001-09-24), pages 5147 - 65151, XP002218740, ISSN: 0020-1669
PETRIG J ET AL: "Derivatisation of glucose and 2-deoxyglucose for transition metal complexation: substitution reactions with organometallic [99m]Tc and Re precursors and fundamental NMR investigations", CHEMISTRY - A EUROPEAN JOURNAL, WILEY-VCH, WEILHEIM, DE, vol. 7, no. 9, 4 May 2001 (2001-05-04), pages 1866 - 1873, XP002218741, ISSN: 0947-6539
FALLER J W ET AL: "The synthesis of new complexes of rhenium(I) with heterotridentate [P,N,O] ligands", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER-SEQUOIA S.A. LAUSANNE, CH, vol. 626, no. 1-2, 30 April 2001 (2001-04-30), pages 181 - 185, XP004235661, ISSN: 0022-328X
SCHIBLI R ET AL: "Influence of the denticity of ligand systems on the in vitro and in vivo behaviour of [99m]Tc(I)-tricarbonyl complexes: a hint for the future functionalisation of biomolecules", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 11, no. 3, May 2000 (2000-05-01), pages 345 - 351, XP002218742, ISSN: 1043-1802
POLLAK A ET AL: "A convenient method of preparing high specific activity technetium complexes using thiol-containing chelators absorbed on gold", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 121, no. 49, 15 December 1999 (1999-12-15), pages 11593 - 11594, XP002218743, ISSN: 0002-7863
ALBERTO ET AL: "A Novel Organometallic Aqua Complex of Technetium for the Labeling of Biomolecules: Synthesis of [99mTc(OH2)3(CO)3]+ from [99mTcO4]- in Aqueous Solution and Its Reaction with a Bifunctional Ligand", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 120, no. 31, 12 August 1998 (1998-08-12), pages 7987 - 7988, XP002149527, ISSN: 0002-7863
STOR G J ET AL: "Spectroelectrochemical (IR, UV/Vis) determination of the reductive pathways for a series of [Re(CO)3(alpha-diimine)L']0/+ (L' = Halide, Otf-, THF, MeCN, n-PrCN, PPh3, P(OMe)3) complexes", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 14, no. 3, March 1995 (1995-03-01), pages 1115 - 1131, XP002218744, ISSN: 0276-7333
ALBERTO R ET AL: "New organometallic technetium complexes in high and low oxidation states", RADIOCHIMICA ACTA, LONDON, GB, vol. 63, 1993, pages 153 - 161, XP002060831
DUNN-DUFAULT R ET AL: "A solid-phase technique for preparation of no-carrier-added technetium-99m radiopharmaceuticals: application to the streptavidin/biotin system", NUCLEAR MEDICINE AND BIOLOGY, ELSEVIER SCIENCE PUBLISHERS, NEW YORK, NY, US, vol. 27, no. 8, November 2000 (2000-11-01), pages 803 - 807, XP004228484, ISSN: 0969-8051
KHEHYONG N ET AL: "Preparation of Acid-labile Resins with Halide Linkers and their Utility in Solid Phase Organic Synthesis", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 38, no. 6, 10 February 1997 (1997-02-10), pages 973 - 976, XP004033909, ISSN: 0040-4039
VAN WIJNKOOP M ET AL: "1,3-Dipolar cycloaddition reactions to the C=X-M fragment. 7. Reaction of Ru(CO)3(i-Pr-DAB) with dimethyl acetylenedicarboxylate. X-ray crystal structure of the protonated initial bicyclo[2.2.1] adduct", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 11, no. 11, November 1992 (1992-11-01), pages 3607 - 3617, XP002218745, ISSN: 0276-7333
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