Synthesis of renin inhibitors involving a cycloaddition...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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07973175

ABSTRACT:
The invention related to a novel process, novel process steps and novel intermediates useful in the synthesis of pharmaceutically active compounds, especially renin inhibitors, such as Aliskiren. Inter alia, the invention relates to a process for the manufacture of a compound of the formula III,wherein R, R1, and R′ are as defined in the specification, or a salt thereof, and a compound of formula IVwherein R, R1, R2and R′ are as defined in the specification, and processes of manufacturing these.

REFERENCES:
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patent: 0 168 607 (1986-01-01), None
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Hanessian et al., “The power of visual imagery in synthesis planning, stereocontrolled approaches to CGP-60536B, a potent renin inhibitor”, J. Org. Chem. 67, pp. 4261-4274 (2002).
Mealy et al., “Aliskiren Fumarate”, Drugs of the Future, 26 (12), pp. 1139-1148 (2001).
Meyer et al., “A short synthesis of polysubstituted pyrrolidines via α-(alkylidene-amino)nitriles”, SYNLETT, No. 5, pp. 787-790 (2004).
Nyerges et al., “Silver acetate-catalysed asymmetric 1,3-dipolar cycloadditions of imines and chiral acrylamides,” Tetrahedron, vol. 61, No. 15, pp. 3745-3753 (2005).
Coldham et al., “Intramolecular Dipolar Cycloaddition Reactions of Azomethine Ylides,” Chem. Rev., vol. 105, pp. 2765-2809 (2005).
Husinec et al., “Chiral catalysts in the stereoselective synthesis of pyrrolidine derivatives via metallo-azomethine ylides,” Tetrahedron: Asymmetry 16, pp. 2047-2061 (2005).

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