((ir, 3s)-3-isopropyl-3-{ [3-(trifluoromethyl)-7,...

C - Chemistry – Metallurgy – 07 – D

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C07D 471/04 (2006.01) A61K 31/4375 (2006.01) A61P 37/00 (2006.01)

Patent

CA 2543201

((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 succinate salt of formula: (see above formula) and an efficient synthesis for its preparation; the succinate salt is crystalline and is a potent CCR2 inhibitor which is useful for treating inflammatory and immunoregulatory disorders or diseases.

L'invention concerne une synthèse efficace pour la préparation de ((1R,3S)-3-isopropyl-3-{[3-(trifluorométhyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)[(3S,4S)-3-méthoxytétrahydro-2H-pyran-4-yl]amine et son sel de succinate. L'invention porte également sur une synthèse efficace pour la préparation d'intermédiaires (3R)-3-méthoxytétrahydro-4H-pyran-4-one; d'acide (1<I>S</I>,4<I>S</I>)-4-(2,5-diméthyl-1<I>H</I>-pyrrol-1-yl)-1-isopropylcyclopent-2-ène-1-carboxylique; et 3-(trifluorométhyl)-5,6,7,8-tétrahydro-1,6-naphthyridine; et pour la préparation du précurseur (3S,4S)-N-((1S,4S)-4-isopropyl-4-{[3-(trifluorométhyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopent-2-en-1-yl)-3-méthoxytétrahydro-2H-pyran-4-amine. L'invention est avantageuse en ce que le sel de succinate de ((1R,3S)-3-isopropyl-3-{[3-(trifluorométhyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]carbonyl}cyclopentyl)[(3S,4S)-3-m éthoxytétrahydro-2H-pyran-4-yl]amine présente des propriétés supérieures.

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