Title:
RADIOIODINATION METHOD
Document Type and Number:
WIPO Patent Application WO/2011/020907
Kind Code:
A1
Abstract:
The present invention provides a novel method of labelling biological targeting molecules (BTMs) of interest with radioiodine. Also provided are novel radioiodinated BTMs prepared using the method, as well as radiopharmaceutical compositions comprising such radioiodinated BTMs. The invention also provides radioiodinated intermediates useful in the method, as well as in vivo imaging methods using.
Inventors:
AVORY MICHELLE (GB)
TRIGG WILLIAM (GB)
TRIGG WILLIAM (GB)
Application Number:
PCT/EP2010/062149
Publication Date:
February 24, 2011
Filing Date:
August 20, 2010
Export Citation:
Assignee:
GE HEALTHCARE LTD (GB)
AVORY MICHELLE (GB)
TRIGG WILLIAM (GB)
AVORY MICHELLE (GB)
TRIGG WILLIAM (GB)
International Classes:
C07D249/04; A61K51/04; A61K51/08; C07B59/00; C07D261/08
Domestic Patent References:
| WO2006067376A2 | 2006-06-29 | |||
| WO2007148089A2 | 2007-12-27 | |||
| WO2006116629A2 | 2006-11-02 | |||
| WO2006067376A2 | 2006-06-29 | |||
| WO2007148089A2 | 2007-12-27 | |||
| WO2006116629A2 | 2006-11-02 |
Other References:
JOS L. H. EERSELS ET AL: "Manufacturing I-123-labelled radiopharmaceuticals. Pitfalls and solutions", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 48, no. 4, 30 March 2005 (2005-03-30), pages 241 - 257, XP008130278, ISSN: 0362-4803, [retrieved on 20050210], DOI: DOI:10.1002/JLCR.922
BOLTON R: "Radiohalogen incorporation into organic systems", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 45, no. 6, 1 May 2002 (2002-05-01), pages 485 - 528, XP002484962, ISSN: 0362-4803, DOI: DOI:10.1002/JLCR.575
F. HIMO ET AL.: "Copper(I)-Catalyzed synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, no. 1, 2005, pages 210 - 216, XP002614558
K. NWE ET AL.: "Growing Applications of 'Click Chemistry' for Bioconjugation in Contemporary Biomedical Research", CANCER BIOTHERAPY AND RADIOPHARMACEUTICALS, vol. 24, no. 3, June 2009 (2009-06-01), pages 289 - 302, XP002614559
YI-YIN KU ET AL.: "Use of Iodoacetylene as a Dipolarophile in the Synthesis of 5-Iodoisoxazole Derivatives", ORGANIC LETTERS, vol. 3, no. 26, 2001, pages 4185 - 4187, XP002614560
H. ALI ET AL.: "Synthesis of Radiopharmaceuticals via Organotin Intermediates", SYNTHESIS, 1996, pages 423 - 445, XP002614561
GEORGE W KABALKA ET AL: "A facile synthesis of radioiodinated alkynyl iodides using potassium alkynyltrifluoroborates", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 48, no. 5, 1 April 2005 (2005-04-01), pages 359 - 362, XP008130295, ISSN: 0362-4803, [retrieved on 20050307], DOI: DOI:10.1002/JLCR.931
GEORGE W KABALKA ET AL: "No-carrier-added radiohalogenations utilizing organoborates", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 50, no. 5-6, 1 April 2007 (2007-04-01), pages 446 - 447, XP008130279, ISSN: 0362-4803, [retrieved on 20070730], DOI: DOI:10.1002/JLCR.1186
BOLTON, J.LAB.COMP.RADIOPHARM., vol. 45, 2002, pages 485 - 528
EERSELS, J.LAB.COMP.RADIOPHARM., vol. 48, 2005, pages 241 - 257
ALI, SYNTHESIS, 1996, pages 423 - 445
J.LAB.COMP.RADIOPHARM., vol. 50, 2007, pages 446888 - 447894
NWE ET AL., CANCER BIOTHER.RADIOPHARM., vol. 24, no. 3, 2009, pages 289 - 302
LI, BIOCONJ.CHEM., vol. 18, no. 6, 2007, pages 1987 - 1994
HAUSNER ET AL., J.MED.CHEM., vol. 51, no. 19, 2008, pages 5901 - 5904
MIDDLETON, J.AM.CHEM.SOC., vol. 81, 1959, pages 803 - 804
WU; FOKIN, ALDRICHIM.ACTA, vol. 40, no. 1, 2007, pages 7 - 17
MELDAL; TORNOE, CHEM. REV., vol. 108, 2008, pages 2952 - 3015
MORGAN; NOWOTNIK, DRUG NEWS PERSPECT., vol. 12, no. 3, 1999, pages 137 - 145
R.PASQUALINI ET AL., NAT BIOTECHNOL., vol. 15, no. 6, June 1997 (1997-06-01), pages 542 - 6
E. RUOSLAHTI, KIDNEY INT., vol. 51, no. 5, May 1997 (1997-05-01), pages 1413 - 7
M.TONE ET AL., J.BIOCHEM, vol. 102, 1987, pages 1033
L.HANSSON ET AL., GENE, vol. 139, 1994, pages 193
A.GUTMAN ET AL., FEBS LETT., vol. 207, 1996, pages 145
V.DIXIT ET AL., PROC. NATL. ACAD. SCI., vol. 83, 1986, pages 5449
R.F.DOOLITTLE, ANN. REV. BIOCHEM., vol. 53, 1984, pages 195
E. C. JORGENSEN ET AL., J. MED. CHEM., vol. 22, no. 9, 1979, pages 1038 - 1044
R.K. TURKER ET AL., SCIENCE, vol. 177, 1972, pages 1203
SATYAMURTHY ET AL., CLIN.POSITR.IMAG., vol. 2, no. 5, 1999, pages 233 - 253
MELDAL; TORNOE, CHEM. REV., vol. 108, no. 2008, 2008, pages 2952
H.C.KOLB; K.B. SHARPLESS, DRUG DISCOVERY TODAY, vol. 8, no. 24, December 2003 (2003-12-01)
LI ET AL., BIOCONJ.CHEM., vol. 18, no. 6, 2007, pages 1987 - 1994
DE GRAAF ET AL., BIOCONJ.CHEM., vol. 20, no. 7, 2009, pages 1281 - 1295
KU ET AL., ORG.LETT., vol. 3, no. 26, 2001, pages 4185 - 4187
ALI ET AL., SYNTHESIS, 1996
J.LAB.COMP.RADIOPHARM., vol. 45, 2002, pages 485 - 528
KABALKA ET AL., J.LAB.COMP.RADIOPHARM., vol. 48, 2005, pages 359 - 362
KABALKA ET AL., J.LAB.COMP.RADIOPHARM., vol. 49, 2006, pages 11 - 15
FR. MOULIN, HELVET. CHIM. ACTA, vol. 35, 1952, pages 167 - 80
BOLTON R: "Radiohalogen incorporation into organic systems", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 45, no. 6, 1 May 2002 (2002-05-01), pages 485 - 528, XP002484962, ISSN: 0362-4803, DOI: DOI:10.1002/JLCR.575
F. HIMO ET AL.: "Copper(I)-Catalyzed synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 127, no. 1, 2005, pages 210 - 216, XP002614558
K. NWE ET AL.: "Growing Applications of 'Click Chemistry' for Bioconjugation in Contemporary Biomedical Research", CANCER BIOTHERAPY AND RADIOPHARMACEUTICALS, vol. 24, no. 3, June 2009 (2009-06-01), pages 289 - 302, XP002614559
YI-YIN KU ET AL.: "Use of Iodoacetylene as a Dipolarophile in the Synthesis of 5-Iodoisoxazole Derivatives", ORGANIC LETTERS, vol. 3, no. 26, 2001, pages 4185 - 4187, XP002614560
H. ALI ET AL.: "Synthesis of Radiopharmaceuticals via Organotin Intermediates", SYNTHESIS, 1996, pages 423 - 445, XP002614561
GEORGE W KABALKA ET AL: "A facile synthesis of radioiodinated alkynyl iodides using potassium alkynyltrifluoroborates", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 48, no. 5, 1 April 2005 (2005-04-01), pages 359 - 362, XP008130295, ISSN: 0362-4803, [retrieved on 20050307], DOI: DOI:10.1002/JLCR.931
GEORGE W KABALKA ET AL: "No-carrier-added radiohalogenations utilizing organoborates", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY, CHICHESTER, GB, vol. 50, no. 5-6, 1 April 2007 (2007-04-01), pages 446 - 447, XP008130279, ISSN: 0362-4803, [retrieved on 20070730], DOI: DOI:10.1002/JLCR.1186
BOLTON, J.LAB.COMP.RADIOPHARM., vol. 45, 2002, pages 485 - 528
EERSELS, J.LAB.COMP.RADIOPHARM., vol. 48, 2005, pages 241 - 257
ALI, SYNTHESIS, 1996, pages 423 - 445
J.LAB.COMP.RADIOPHARM., vol. 50, 2007, pages 446888 - 447894
NWE ET AL., CANCER BIOTHER.RADIOPHARM., vol. 24, no. 3, 2009, pages 289 - 302
LI, BIOCONJ.CHEM., vol. 18, no. 6, 2007, pages 1987 - 1994
HAUSNER ET AL., J.MED.CHEM., vol. 51, no. 19, 2008, pages 5901 - 5904
MIDDLETON, J.AM.CHEM.SOC., vol. 81, 1959, pages 803 - 804
WU; FOKIN, ALDRICHIM.ACTA, vol. 40, no. 1, 2007, pages 7 - 17
MELDAL; TORNOE, CHEM. REV., vol. 108, 2008, pages 2952 - 3015
MORGAN; NOWOTNIK, DRUG NEWS PERSPECT., vol. 12, no. 3, 1999, pages 137 - 145
R.PASQUALINI ET AL., NAT BIOTECHNOL., vol. 15, no. 6, June 1997 (1997-06-01), pages 542 - 6
E. RUOSLAHTI, KIDNEY INT., vol. 51, no. 5, May 1997 (1997-05-01), pages 1413 - 7
M.TONE ET AL., J.BIOCHEM, vol. 102, 1987, pages 1033
L.HANSSON ET AL., GENE, vol. 139, 1994, pages 193
A.GUTMAN ET AL., FEBS LETT., vol. 207, 1996, pages 145
V.DIXIT ET AL., PROC. NATL. ACAD. SCI., vol. 83, 1986, pages 5449
R.F.DOOLITTLE, ANN. REV. BIOCHEM., vol. 53, 1984, pages 195
E. C. JORGENSEN ET AL., J. MED. CHEM., vol. 22, no. 9, 1979, pages 1038 - 1044
R.K. TURKER ET AL., SCIENCE, vol. 177, 1972, pages 1203
SATYAMURTHY ET AL., CLIN.POSITR.IMAG., vol. 2, no. 5, 1999, pages 233 - 253
MELDAL; TORNOE, CHEM. REV., vol. 108, no. 2008, 2008, pages 2952
H.C.KOLB; K.B. SHARPLESS, DRUG DISCOVERY TODAY, vol. 8, no. 24, December 2003 (2003-12-01)
LI ET AL., BIOCONJ.CHEM., vol. 18, no. 6, 2007, pages 1987 - 1994
DE GRAAF ET AL., BIOCONJ.CHEM., vol. 20, no. 7, 2009, pages 1281 - 1295
KU ET AL., ORG.LETT., vol. 3, no. 26, 2001, pages 4185 - 4187
ALI ET AL., SYNTHESIS, 1996
J.LAB.COMP.RADIOPHARM., vol. 45, 2002, pages 485 - 528
KABALKA ET AL., J.LAB.COMP.RADIOPHARM., vol. 48, 2005, pages 359 - 362
KABALKA ET AL., J.LAB.COMP.RADIOPHARM., vol. 49, 2006, pages 11 - 15
FR. MOULIN, HELVET. CHIM. ACTA, vol. 35, 1952, pages 167 - 80
Attorney, Agent or Firm:
CANNING, Lewis Reuben (Pollards WoodNightingales Lane,Chalfont St Giles, Buckinghamshire HP8 4SP, GB)
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