Method for the use of [ 11 C] carbon monoxide in labeling...

Organic compounds -- part of the class 532-570 series – Organic compounds – Radioactive metal containing

Reexamination Certificate

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C204S001001, C204S157970, C422S159000, C422S186000, C564S123000

Reexamination Certificate

active

07553942

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.

REFERENCES:
patent: WO 02/102711 (2002-12-01), None
Obaidur Rahman, Tor Kihlberg, and Bengt Langstrom Aryl Triflates and [11 C]/(13C) Carbon Monoxide in the Synthesis of 11C-/13C-Amides J.Org. Chem. 2003, 68, 3558-3562.
Itsenko, Oleksiy, et.al. “Photoinitiated Carbonylation with [11C] Carbon Monoxide Using Amines and Alkyl Iodides” Journal of Organic Chemistry, vol. 69, No. 13, 2004, pp. 4356-4360.
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, pp. 1953-1954.
Ryu, I “Radical carbonylation of iodoalkanes and saturated alcohols using carbon monoxide” Chem. Soc. Rev., vol. 30, 2001, pp. 16-25.
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, May 9, 2003, pp. 3558-3562.
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 Cehmical Society Easton US, vol. 64, 1999, pp. 9201-9205.
F. Karimi, et.al., “Synthesis of 11C-labelled amides by palladium-mediated carboxamination using [11C]Carbon monoxide, in situ activated amines and 1,2,2,6,6-Pentapiperidine” European Journal of Organic Chemistry, 2003, pp. 2132-2137.
F. Karimi, et.al., “Synthesis of 11C-amides using [11C]-carbon monoxide and in situ activiated amines by palladium-mediated carboxaminations” Or. Biomol. Chem. vol. 1, 2003, pp. 541-546.
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, pp. 497-503.
Int'l Search Report and written opinion PCT/IB2005/004086 dated Jun. 2006.

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