WO2006051428A3 - Use of [11c] carbon monoxide in labeling synthesis of 11c-labelled amides using photo-induced free radical carbonylation - Google Patents

Use of [11c] carbon monoxide in labeling synthesis of 11c-labelled amides using photo-induced free radical carbonylation Download PDF

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Publication number
WO2006051428A3
WO2006051428A3 PCT/IB2005/004086 IB2005004086W WO2006051428A3 WO 2006051428 A3 WO2006051428 A3 WO 2006051428A3 IB 2005004086 W IB2005004086 W IB 2005004086W WO 2006051428 A3 WO2006051428 A3 WO 2006051428A3
Authority
WO
WIPO (PCT)
Prior art keywords
photo
amides
carbon monoxide
labelled
free radical
Prior art date
Application number
PCT/IB2005/004086
Other languages
French (fr)
Other versions
WO2006051428A2 (en
Inventor
Bengt Langstrom
Tor Kihlberg
Oleksiy Itsenko
Original Assignee
Ge Healthcare Ltd
Bengt Langstrom
Tor Kihlberg
Oleksiy Itsenko
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ge Healthcare Ltd, Bengt Langstrom, Tor Kihlberg, Oleksiy Itsenko filed Critical Ge Healthcare Ltd
Priority to EP05850785A priority Critical patent/EP1817269B1/en
Priority to ES05850785T priority patent/ES2398699T3/en
Publication of WO2006051428A2 publication Critical patent/WO2006051428A2/en
Publication of WO2006051428A3 publication Critical patent/WO2006051428A3/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04—Organic compounds
    • A61K51/0404—Lipids, e.g. triglycerides; Polycationic carriers
    • A61K51/0406—Amines, polyamines, e.g. spermine, spermidine, amino acids, (bis)guanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds

Abstract

Methods and reagents for photo-initiated carbonylation with carbon-isotope labeled carbon monoxide using weakly nucleophilic amines and alkyl/aryl iodides are provided. The resultant carbon-isotope labeled amides are useful as radiopharmaceuticals, especially for use in Positron Emission Tomography (PET). Associated kits for PET studies are also provided.
PCT/IB2005/004086 2004-11-05 2005-11-07 Use of [11c] carbon monoxide in labeling synthesis of 11c-labelled amides using photo-induced free radical carbonylation WO2006051428A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP05850785A EP1817269B1 (en) 2004-11-05 2005-11-07 Use of [11c] carbon monoxide in labeling synthesis of 11c-labelled amides using photo-induced free radical carbonylation
ES05850785T ES2398699T3 (en) 2004-11-05 2005-11-07 Use of carbon monoxide [11C] in the synthesis of labeled amides labeled with 11C using free radical photoinduced carbonylation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US62537704P 2004-11-05 2004-11-05
US60/625,377 2004-11-05

Publications (2)

Publication Number Publication Date
WO2006051428A2 WO2006051428A2 (en) 2006-05-18
WO2006051428A3 true WO2006051428A3 (en) 2006-08-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2005/004086 WO2006051428A2 (en) 2004-11-05 2005-11-07 Use of [11c] carbon monoxide in labeling synthesis of 11c-labelled amides using photo-induced free radical carbonylation

Country Status (4)

Country Link
US (2) US7553942B2 (en)
EP (1) EP1817269B1 (en)
ES (1) ES2398699T3 (en)
WO (1) WO2006051428A2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2386364T3 (en) * 2005-02-01 2012-08-17 Ge Healthcare Limited Procedure for the use of carbon monoxide [11C] in the synthesis of labeling of compounds labeled by 11C by thermally induced free radical carbonylation
US8226927B2 (en) * 2006-05-25 2012-07-24 Farhad Karimi 11C/18F-labeled inhibitors of glycogen synthase kinase-3
US8336025B1 (en) * 2007-02-08 2012-12-18 The Mathworks, Inc. Pattern modeling methods and systems
US8776015B1 (en) 2007-02-08 2014-07-08 The Mathworks, Inc. Pattern modeling methods and systems
US9101895B2 (en) 2011-04-15 2015-08-11 General Electric Company System for mixing and dispersing microbubble pharmaceuticals
CN104515819B (en) * 2013-09-29 2016-05-11 北京普析通用仪器有限责任公司 Sampling device and thermal weight loss-gas-chromatography coupling system, thermal weight loss-gas chromatography-mass spectrography system
CN117003693A (en) * 2022-05-05 2023-11-07 四川大学华西医院 Piperidine derivatives, preparation method and application thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL101722A (en) * 1991-05-02 1996-05-14 Wyeth John & Brother Ltd Piperazine derivatives their preparation and pharmaceutical compositions containing them
SE0102174D0 (en) * 2001-06-19 2001-06-19 Tor Kihlberg Method and apparatus for production and use of (11C) carbon monoxide in labeling synthesis
US8741261B2 (en) * 2003-12-18 2014-06-03 Ge Healthcare Limited Methods for carbon isotope labeling synthesis by transition metal-promoted carbonylation via isocyanate using azides and carbon-isotope monoxide
EP1768705A4 (en) * 2004-05-07 2008-01-23 Univ California System Method for detecting alzheimer's disease and other forms of dementia, and measuring their progression

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
FARHAD KARIMI ET AL.: "Synthesis of 11C-amides using [11C]carbon monoxide and in situ activated amines by palladium-mediated carboxaminations", ORG. BIOMOL. CHEM., vol. 1, 2003, pages 541 - 546, XP002383785 *
FARHAD KARIMI ET AL.: "Synthesis of 11C-Labelled Amides by Paladium-Mediated Carboxamimation Using [11C]Carbon Monoxide, in situ Activated Amines and 1,2,2,6,6-Pentamethylpiperidine", EUR. J. ORG. CHEM., 2003, pages 2312 - 2137, XP002383784 *
ILHYONG RYU: "Radical carboxylations of iodoalkanes and saturated alcohols using carbon monoxide", CHEM. SOC. REV., vol. 30, 2001, pages 16 - 25, XP002383787 *
KIHLBERG T ET AL: "Biologically Active C-Labeled Amides Using Palladium-Mediated Reactions with Aryl Halides and [11C]Carbon Monoxide", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 64, 1999, pages 9201 - 9205, XP002168717, ISSN: 0022-3263 *
OLEKSIY ITSENKO ET AL.: "Photoinitiated Carbonylation with [11C]Carbon Monoxide Using Amines and Alkyl Iodides", J. ORG. CHEM., vol. 69, 6 February 2004 (2004-02-06), pages 4356 - 4360, XP002383783 *
RAHMAN O ET AL: "Aryl Triflates and 11C/13C Carbon Monoxide in the Synthesis of 11C/13C Amides", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 68, 9 May 2003 (2003-05-09), pages 3558 - 3562, XP002319931, ISSN: 0022-3263 *
RYU I ET AL: "Metal catalyst-free by design. The synthesis of amides from alkyl iodides carbon monoxide and amines by a hybrid radical/ionic reaction", CHEMICAL COMMUNICATIONS - CHEMCOM, ROYAL SOCIETY OF CHEMISTRY, GB, 1998, pages 1953 - 1954, XP002319932, ISSN: 1359-7345 *
SERGIO KREIMERMAN ET AL.: "Synthesis of nitrogen heterocycles based on atom transfer carbonylation of bifunctional amines", C. R. ACAD. SCI. PARIS, CHIMIE / CHEMISTRY, vol. 4, 2001, pages 497 - 503, XP002383786 *

Also Published As

Publication number Publication date
US7553942B2 (en) 2009-06-30
EP1817269A2 (en) 2007-08-15
US20060133998A1 (en) 2006-06-22
ES2398699T3 (en) 2013-03-21
EP1817269B1 (en) 2013-01-02
US8129528B2 (en) 2012-03-06
US20090297445A1 (en) 2009-12-03
WO2006051428A2 (en) 2006-05-18

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