Title:
CHOLINE ANALOGS AS RADIOTRACER
Document Type and Number:
WIPO Patent Application WO/2012/040138
Kind Code:
A3
Abstract:
Novel radiotracer(s) for Positron Emission Tomography (PET) or Single Photon Emission Computed Tomography (SPECT) imaging of disease states related to altered choline metabolism (e.g., tumor imaging of prostate, breast, brain, esophageal, ovarian, endometrial, lung and prostate cancer - primary tumor, nodal disease or metastases). The present invention also describes intermediate(s), pre-cursor(s), pharmaceutical composition(s), methods of making, and methods of use of the novel radiotracer(s).
Inventors:
ABOAGYE ERIC OFORI (GB)
ROBINS EDWARD GEORGE (SG)
SMITH GRAHAM (GB)
ZHAO YONGJUN (CN)
LEYTON JULIUS (GB)
TURTON DAVID (GB)
WILSON ANTHONY (GB)
BHALLA RAJIV (GB)
BRICKUTE DIANA (GB)
ROBINS EDWARD GEORGE (SG)
SMITH GRAHAM (GB)
ZHAO YONGJUN (CN)
LEYTON JULIUS (GB)
TURTON DAVID (GB)
WILSON ANTHONY (GB)
BHALLA RAJIV (GB)
BRICKUTE DIANA (GB)
Application Number:
PCT/US2011/052253
Publication Date:
May 18, 2012
Filing Date:
September 20, 2011
Export Citation:
Assignee:
GE HEALTHCARE LTD (GB)
IMPERIAL COLLEGE (GB)
MEDI PHYSICS INC (US)
ABOAGYE ERIC OFORI (GB)
ROBINS EDWARD GEORGE (SG)
SMITH GRAHAM (GB)
ZHAO YONGJUN (CN)
LEYTON JULIUS (GB)
TURTON DAVID (GB)
WILSON ANTHONY (GB)
BHALLA RAJIV (GB)
BRICKUTE DIANA (GB)
IMPERIAL COLLEGE (GB)
MEDI PHYSICS INC (US)
ABOAGYE ERIC OFORI (GB)
ROBINS EDWARD GEORGE (SG)
SMITH GRAHAM (GB)
ZHAO YONGJUN (CN)
LEYTON JULIUS (GB)
TURTON DAVID (GB)
WILSON ANTHONY (GB)
BHALLA RAJIV (GB)
BRICKUTE DIANA (GB)
International Classes:
C07C213/00; C07C213/02; C07C213/06; C07C215/08; C07C217/10
Domestic Patent References:
| WO1992020646A1 | 1992-11-26 | |||
| WO2005009928A2 | 2005-02-03 | |||
| WO2006082108A2 | 2006-08-10 |
Other References:
J. LEYTON ET AL: "[18F]Fluoromethyl-[1,2-2H4]-Choline: A Novel Radiotracer for Imaging Choline Metabolism in Tumors by Positron Emission Tomography", CANCER RESEARCH, vol. 69, no. 19, 1 October 2009 (2009-10-01), pages 7721 - 7728, XP055017080, ISSN: 0008-5472, DOI: 10.1158/0008-5472.CAN-09-1419
GRAHAM SMITH ET AL: "Radiosynthesis and pre-clinical evaluation of [18F]fluoro-[1,2-2H4]choline", NUCLEAR MEDICINE AND BIOLOGY, vol. 38, no. 1, 1 September 2010 (2010-09-01), pages 39 - 51, XP002667666, Retrieved from the Internet [retrieved on 20120215], DOI: 10.1016/j.nucmedbio.2010.06.012
JEHANGIR S. MISTRY ET AL: "Neurochemistry of aging. 2. Design, synthesis and biological evaluation of halomethyl analogs of choline with high affinity choline transport inhibitory activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 34, no. 7, 1 July 1991 (1991-07-01), pages 2031 - 2036, XP055017160, ISSN: 0022-2623, DOI: 10.1021/jm00111a016
R.G. BRIDGES ET AL: "The incorporation of analogues of choline into the phospholipids of the larva of the housefly, Musca domestica", JOURNAL OF INSECT PHYSIOLOGY, vol. 16, no. 4, 1 April 1970 (1970-04-01), pages 579 - 593, XP055017201, ISSN: 0022-1910, DOI: 10.1016/0022-1910(70)90092-2
ZHANG M-R ET AL: "Development of an automated system for synthesizing <18>F-labeled compounds using [<18>F]fluoroethyl bromide as a synthetic precursor", APPLIED RADIATION AND ISOTOPES, vol. 57, no. 3, 1 September 2002 (2002-09-01), ELSEVIER, OXFORD, GB, pages 335 - 342, XP004370242, ISSN: 0969-8043, DOI: 10.1016/S0969-8043(02)00075-1
LIM ET AL: "AUTOMATED PRODUCTION OF [18F]FECH AND [18f]FCH: PREPARATION AND USE OF [18F]FLUOROALKANE SULFONATES AS FLUOROALKYLATION AGENTS", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 46, 1 August 2003 (2003-08-01), JOHN WILEY, CHICHESTER, GB, pages S46, XP002313484, ISSN: 0362-4803, DOI: 10.1002/JLCR.757
KRYZA ET AL: "Fully automated [<18>F]fluorocholine synthesis in the TracerLab MXFDG Coincidence synthesizer", NUCLEAR MEDICINE AND BIOLOGY, vol. 35, no. 2, 8 February 2008 (2008-02-08), ELSEVIER, NY, US, pages 255 - 260, XP022460575, ISSN: 0969-8051
GRAHAM SMITH ET AL: "Radiosynthesis and pre-clinical evaluation of [18F]fluoro-[1,2-2H4]choline", NUCLEAR MEDICINE AND BIOLOGY, vol. 38, no. 1, 1 September 2010 (2010-09-01), pages 39 - 51, XP002667666, Retrieved from the Internet
JEHANGIR S. MISTRY ET AL: "Neurochemistry of aging. 2. Design, synthesis and biological evaluation of halomethyl analogs of choline with high affinity choline transport inhibitory activity", JOURNAL OF MEDICINAL CHEMISTRY, vol. 34, no. 7, 1 July 1991 (1991-07-01), pages 2031 - 2036, XP055017160, ISSN: 0022-2623, DOI: 10.1021/jm00111a016
R.G. BRIDGES ET AL: "The incorporation of analogues of choline into the phospholipids of the larva of the housefly, Musca domestica", JOURNAL OF INSECT PHYSIOLOGY, vol. 16, no. 4, 1 April 1970 (1970-04-01), pages 579 - 593, XP055017201, ISSN: 0022-1910, DOI: 10.1016/0022-1910(70)90092-2
ZHANG M-R ET AL: "Development of an automated system for synthesizing <18>F-labeled compounds using [<18>F]fluoroethyl bromide as a synthetic precursor", APPLIED RADIATION AND ISOTOPES, vol. 57, no. 3, 1 September 2002 (2002-09-01), ELSEVIER, OXFORD, GB, pages 335 - 342, XP004370242, ISSN: 0969-8043, DOI: 10.1016/S0969-8043(02)00075-1
LIM ET AL: "AUTOMATED PRODUCTION OF [18F]FECH AND [18f]FCH: PREPARATION AND USE OF [18F]FLUOROALKANE SULFONATES AS FLUOROALKYLATION AGENTS", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 46, 1 August 2003 (2003-08-01), JOHN WILEY, CHICHESTER, GB, pages S46, XP002313484, ISSN: 0362-4803, DOI: 10.1002/JLCR.757
KRYZA ET AL: "Fully automated [<18>F]fluorocholine synthesis in the TracerLab MXFDG Coincidence synthesizer", NUCLEAR MEDICINE AND BIOLOGY, vol. 35, no. 2, 8 February 2008 (2008-02-08), ELSEVIER, NY, US, pages 255 - 260, XP022460575, ISSN: 0969-8051
Attorney, Agent or Firm:
LEE, Christine et al. (Inc.101 Carnegie Cente, Princeton NJ, US)
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