PROCESS FOR THE PREPARATION OF CCR-2 ANTAGONIST

WIPO Patent Application WO2005044795

A8

The present invention provides an efficient synthesis for the preparation of ((1R,3S)-3-isopropyl-3- {[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl} cyclopentyl)[(3S,4S)-3-m ethoxytetrahydro- 2H-pyran-4-yl]amine and its succinate salt. The present invention additionally provides an efficient syntheses for the preparation of intermediates (3R)-3-methoxytetrahydro- 4H-pyran-4-one; (1S,4S)-4-(2,5-dimethyl-1H-pyrrol- 1-yl)-1-isopropylcyclopent-2- ene-1-carboxylic acid; and 3-(trifluoromethyl)-5,6,7,8-tetrahydro-1, 6-naphthyridine; and for the preparation of the precursor (3S,4S)-N-((1S,4S)- 4-isopropyl-4-{[3-(trifluoromethyl)- 7,8-dihydro-1,6-naphthyridin-6(5H)-yl] carbonyl}cyclopent-2-e n-1-yl)- 3-methoxytetrahydro-2H- pyran-4-amine. The invention additionally resides in the superior properties of the succinate salt of ((1R,3S)-3-isopropyl- 3-{[3-(trifluoromethyl)-7, 8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl} cyclopentyl)[(3S,4S)-3- methoxytetrahydro-2H-pyran-4-yl]amine.

CAI DONGWEI (US)
FLEITZ FRED (US)
GE MIN (US)
HOERRNER SCOTT (US)
JAVADI GARY (US)
JENSEN MARK (US)
LARSEN ROBERT (US)
LI WENJIE (US)
NELSON DORIAN (US)
SZUMIGALA ELIZABETH (US)
YANG LIHU (US)
ZHOU CHANGYOU (US)

PCT/US2004/035294

June 22, 2006

October 25, 2004

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MERCK & CO INC (US)
CAI DONGWEI (US)
FLEITZ FRED (US)
GE MIN (US)
HOERRNER SCOTT (US)
JAVADI GARY (US)
JENSEN MARK (US)
LARSEN ROBERT (US)
LI WENJIE (US)
NELSON DORIAN (US)
SZUMIGALA ELIZABETH (US)
YANG LIHU (US)
ZHOU CHANGYOU (US)

C07D207/327; C07C271/24; C07C303/40; C07D309/30; C07D401/04; C07D471/04; C07C311/20

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