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Title:
SYNTHESIS OF 2'-DEOXY-2'-[18F]FLUORO-5-METHYL-1-B-D-ARABINOFURANOSYLURACIL (18F-FMAU)
Document Type and Number:
WIPO Patent Application WO/2012/009666
Kind Code:
A3
Abstract:
The present invention relates to methods of synthesizing 18F-FMAU. In particular, 18F-FMAU is synthesized using one-pot reaction conditions in the presence of Friedel-Crafts catalysts. The one-pot reaction conditions are incorporated into a fully automated cGMP-compliant radiosynthesis module, which results in a reduction in synthesis time and simplifies reaction conditions. The one-pot reaction conditions are also suitable for the production of 5-substitued thymidine or cytidine analogues. The products from the one-pot reaction (e.g. the [18F]-labeled thymidine or cytidine analogues) can be used as probes for imaging tumor proliferative activity. More specifically, these [18F]-labeled thymidine or cytidine analogues can be used as a PET tracer for certain medical conditions, including, but not limited to, cancer disease, autoimmunity inflammation, and bone marrow transplant.

Inventors:
LI, Zibo (214 Rosewood Cir, Logan, Utah, 84321, US)
CAI, Hancheng (2011 Somerset Blvd. #101, Troy, Michigan, 48084, US)
CONTI, Peter S. (1621 Hastings Heights Lane, Pasadena, California, 91107, US)
Application Number:
US2011/044236
Publication Date:
April 10, 2014
Filing Date:
July 15, 2011
Export Citation:
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Assignee:
UNIVERSITY OF SOUTHERN CALIFORNIA (3740 McClintock Avenue, EEB 131Los Angeles, California, 90089, US)
LI, Zibo (214 Rosewood Cir, Logan, Utah, 84321, US)
CAI, Hancheng (2011 Somerset Blvd. #101, Troy, Michigan, 48084, US)
CONTI, Peter S. (1621 Hastings Heights Lane, Pasadena, California, 91107, US)
International Classes:
C07H19/00; A61K51/00
Foreign References:
US6331287B12001-12-18
Other References:
LI ET AL.: "Improved synthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-?-D-arabinofuranosyluracil (18F-FMAU). Abstract 533", J. NUCL. MED. MEETING ABSTRACTS =>0161-5505, vol. 51, no. SUPP., May 2010 (2010-05-01), XP008171890
ANDERSON ET AL.: "Improved synthesis of 2'-deoxy-2'-[18F]-fluoro-1-beta-D-arabinofuranosyl -5- iodouracil ([18F]-FIAU).", NUCL. MED. BIOL., vol. 37, no. 4, May 2010 (2010-05-01), pages 439 - 442, XP027039096
PAOLILLO ET AL.: "A fully automated synthesis of [18F]-FEAU and [18F]-FMAU using a novel dual reactor radiosynthesis module.", J. LABEL. COMPD. RADIOPHARM., vol. 52, no. 13, 2009, pages 553 - 558, XP055136164
LI ET AL.: "Automated synthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-?-D-arabinofuranosyluracil ([18F]-FMAU) using a one reactor radiosynthesis module.", NUCL. MED. BIOL., vol. 38, no. 2, February 2011 (2011-02-01), pages 201 - 206, XP028359721
CAI ET AL.: "The improved syntheses of 5-substituted 2'-[18F]fluoro-2'-deoxy- arabinofuranosyluracil derivatives ([18F]FAU, [18F]FEAU, [18F]FFAU, [18F]FCAU, [18F]FBAU and [18F]FIAU) using a multistep one-pot strategy.", NUCL. MED. BIOL., vol. 38, no. 5, 30 March 2011 (2011-03-30), pages 659 - 666, XP028234567
See also references of EP 2603516A4
Attorney, Agent or Firm:
LEVY, Seth, D. et al. (Davis Wright Tremaine LLP, Suite 2400865 South Figueroa Stree, Los Angeles California, 90017, US)
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