Title:
18F-LABELED AZIDE COMPOUND, REAGENT FOR 18F-LABELING AND METHOD FOR 18F-LABELING OF ALKYNE COMPOUND USING SAME
Document Type and Number:
WIPO Patent Application WO/2010/131745
Kind Code:
A1
Abstract:
Disclosed are: an 18F-labeled azide compound usable in a Huisgen reaction which enables 18F-labeling even though there is only a small amount of an alkyne compound that is the subject substrate, is applicable to PET methods for peptides and oligonucleotides, and enables 18F-labeling of an oligonucleotide at a site other than the 5'- or 3'-end thereof; a reagent for 18F-labeling; and a method for 18F-labeling of an alkyne compound using the same.
The 18F-labeled azide compound is characterized by being represented by structural formula (1).
Inventors:
WATANABE YASUYOSHI (JP)
SUZUKI MASAAKI (JP)
DOI HISASHI (JP)
KUBOYAMA TAKESHI (JP)
OBIKA SATOSHI (JP)
IMANISHI TAKESHI (JP)
SUZUKI MASAAKI (JP)
DOI HISASHI (JP)
KUBOYAMA TAKESHI (JP)
OBIKA SATOSHI (JP)
IMANISHI TAKESHI (JP)
Application Number:
PCT/JP2010/058217
Publication Date:
November 18, 2010
Filing Date:
May 14, 2010
Export Citation:
Assignee:
RIKEN (JP)
UNIV OSAKA (JP)
WATANABE YASUYOSHI (JP)
SUZUKI MASAAKI (JP)
DOI HISASHI (JP)
KUBOYAMA TAKESHI (JP)
OBIKA SATOSHI (JP)
IMANISHI TAKESHI (JP)
UNIV OSAKA (JP)
WATANABE YASUYOSHI (JP)
SUZUKI MASAAKI (JP)
DOI HISASHI (JP)
KUBOYAMA TAKESHI (JP)
OBIKA SATOSHI (JP)
IMANISHI TAKESHI (JP)
International Classes:
C07C247/16; A61K51/00; C07D249/06; C07H7/06; C07B59/00
Domestic Patent References:
| WO2006116629A2 | 2006-11-02 |
Foreign References:
| JP2008515875A | 2008-05-15 |
Other References:
THONON, D. ET AL.: "New Strategy for the Preparation of Clickable Peptides and Labeling with 1-(Azidomethyl)-4-[18F]-fluorobenzene for PET", BIOCONJUGATE CHEM., vol. 20, no. 4, April 2009 (2009-04-01), pages 817 - 823, XP002628601
K. B. SHARPLESS, CLICK CHEMISTRY ADVOCATED
MARIK, J., SUTCLIFFE, J. L., TETRAHEDRON LETT., vol. 47, 2006, pages 6681 - 6684
HAUSNER, S. H., MARIK, J., GAGNON, M. K. J., SUTCLIFFE, J. L., J. MED. CHEM., vol. 51, 2008, pages 5901 - 5904
KIM, D. H., CHOE, Y. S., JUNG, K. -H., LEE, K. -H., CHOI, J. Y., CHOI, Y., KIM, B. -T., ARCH. PHARM. RES., vol. 31, 2008, pages 587 - 593
GLASER, M., ARSTAD, E., BIOCONJUGATE CHEM., vol. 18, 2007, pages 989 - 993
SIRION, U., KIM, H. J., LEE, J. H., SEO, J. W., LEE, B. S., LEE, S. J., OH, S. J., CHI, D. Y., TETRAHEDRON LETT., vol. 48, 2007, pages 3953 - 3957
LI, Z. B., WU, Z., CHEN, K., CHIN, F. T., CHEN, X., BIOCONJUGATE CHEM., vol. 18, 2007, pages 1987 - 1994
RAMENDA, T., BERGMANN, R., WUEST, F., LETT. DRUG DES. DISCOVERY, vol. 4, 2007, pages 279 - 285
INKSTER, J. A. H., GUERIN, B., RUTH. T. J., ADAM, M. J., J. LABELLEDCOMPD. RADIOPHARM., vol. 51, 2008, pages 444 - 452
DOLLE, F., HINNEN, F., VAUFREY, F., TAVITIAN, B., CROUZEL, C., J. LABELLEDCOMPD. RADIOPHARM., vol. 39, 1997, pages 319 - 330
KUHNAST, B., DOLLE, F., TERRAZZINO, T., ROUSSEAU, B., LOCH, C., VAUFREY, F., HINNEN, F., DOIGNON, I., PILLON, F., DAVID, C., BIOCONJUGATE CHEM., vol. 11, 2000, pages 627 - 636
KUHNAST, B., DE BRUIN, B., HINNEN, F., TAVITIAN, B., DOLLE, F., BIOCONJUGATE CHEM., vol. 15, 2004, pages 617 - 627
HEDBERG, E., LANGSTROM, B., ACTA CHEM. SCAND., vol. 51, 1997, pages 1236 - 1240
HEDBERG, E., LANGSTROM, B., ACTA CHEM. SCAND., vol. 52, 1998, pages 1034 - 1039
CHRISTOPHER, W. L., VANBROCKLIN, H. F., TAYLOR, S. E., J. LABEL. COMPD. RADIOPHARM., vol. 45, 2002, pages 257 - 268
ANDERSENA, J. ET AL., SYNLETT, vol. 14, 2005, pages 2209 - 2213
S. OBIKA ET AL., BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 19, 2009, pages 3316 - 3319
S. OBIKA ET AL., BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS
See also references of EP 2500338A4
K. B. SHARPLESS, CLICK CHEMISTRY ADVOCATED
MARIK, J., SUTCLIFFE, J. L., TETRAHEDRON LETT., vol. 47, 2006, pages 6681 - 6684
HAUSNER, S. H., MARIK, J., GAGNON, M. K. J., SUTCLIFFE, J. L., J. MED. CHEM., vol. 51, 2008, pages 5901 - 5904
KIM, D. H., CHOE, Y. S., JUNG, K. -H., LEE, K. -H., CHOI, J. Y., CHOI, Y., KIM, B. -T., ARCH. PHARM. RES., vol. 31, 2008, pages 587 - 593
GLASER, M., ARSTAD, E., BIOCONJUGATE CHEM., vol. 18, 2007, pages 989 - 993
SIRION, U., KIM, H. J., LEE, J. H., SEO, J. W., LEE, B. S., LEE, S. J., OH, S. J., CHI, D. Y., TETRAHEDRON LETT., vol. 48, 2007, pages 3953 - 3957
LI, Z. B., WU, Z., CHEN, K., CHIN, F. T., CHEN, X., BIOCONJUGATE CHEM., vol. 18, 2007, pages 1987 - 1994
RAMENDA, T., BERGMANN, R., WUEST, F., LETT. DRUG DES. DISCOVERY, vol. 4, 2007, pages 279 - 285
INKSTER, J. A. H., GUERIN, B., RUTH. T. J., ADAM, M. J., J. LABELLEDCOMPD. RADIOPHARM., vol. 51, 2008, pages 444 - 452
DOLLE, F., HINNEN, F., VAUFREY, F., TAVITIAN, B., CROUZEL, C., J. LABELLEDCOMPD. RADIOPHARM., vol. 39, 1997, pages 319 - 330
KUHNAST, B., DOLLE, F., TERRAZZINO, T., ROUSSEAU, B., LOCH, C., VAUFREY, F., HINNEN, F., DOIGNON, I., PILLON, F., DAVID, C., BIOCONJUGATE CHEM., vol. 11, 2000, pages 627 - 636
KUHNAST, B., DE BRUIN, B., HINNEN, F., TAVITIAN, B., DOLLE, F., BIOCONJUGATE CHEM., vol. 15, 2004, pages 617 - 627
HEDBERG, E., LANGSTROM, B., ACTA CHEM. SCAND., vol. 51, 1997, pages 1236 - 1240
HEDBERG, E., LANGSTROM, B., ACTA CHEM. SCAND., vol. 52, 1998, pages 1034 - 1039
CHRISTOPHER, W. L., VANBROCKLIN, H. F., TAYLOR, S. E., J. LABEL. COMPD. RADIOPHARM., vol. 45, 2002, pages 257 - 268
ANDERSENA, J. ET AL., SYNLETT, vol. 14, 2005, pages 2209 - 2213
S. OBIKA ET AL., BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 19, 2009, pages 3316 - 3319
S. OBIKA ET AL., BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS
See also references of EP 2500338A4
Attorney, Agent or Firm:
AOYAMA Yo (JP)
Akira Aoyama (JP)
Akira Aoyama (JP)
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