Process for the preparation of CGRP antagonist

Details Process for the preparation of CGRP antagonist Process for the preparation of CGRP antagonist

2007-04-06

2010-11-09

Kifle, Bruck (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

Reexamination Certificate

active

07829699

ABSTRACT:
An efficient synthesis for the preparation of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1 -carboxamide, by coupling (3R,6S)-3-amino-6-(2,3-difluorophenyl)-1-(2,2,2-trifluoroethyl)azepan-2-one and 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride with 1,1′-carbonyldiimidazole (“CDI”) as carbonyl source; and an efficient preparation of the potassium salt of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide.

REFERENCES:
patent: 6953790 (2005-10-01), Burgey et al.
patent: WO 2004/092168 (2004-10-01), None
patent: WO 2007/120589 (2007-10-01), None
patent: WO 2007/120590 (2007-10-01), None
patent: WO 2007/120592 (2007-10-01), None
International Preliminary Report on Patentability for PCT/US2007/008702, dated Oct. 23, 2008.
Int'l Search Report for PCT.US2007/008702, Sep. 19, 2007.
Poulain Rebecca, et al., Journal of Medicinal Chemistry, vol. 44, No. 21, Oct. 11, 2001 pp. 3378-3390.

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