Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2007-08-14
2007-08-14
Solola, Taofiq (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
11081063
ABSTRACT:
A process for stereoselective synthesis of a compound of Formula (X) or Formula (X′)wherein R1, R2, and R3are as defined herein, the process comprising:(a) reacting the starting material of formula A with a chiral sulfoxide anion source in a suitable solvent to prepare a compound of formula C or C′;(b) reducing the sulfoxide of formula C or C′ in a suitable solvent to obtain the compound of formula D or D′; and(c) cyclizing the compound of formula D or D′ in a suitable solvent to form the epoxide compound of Formula (X) or Formula (X′),or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.
REFERENCES:
Bravo, P., et al; Synthesis of (-)-(1S,5R) and (+)-(1R,5S)-trifluoroanalogues of frontalin; Tetrahedron Letters 40 (1999)—6317-6320.
Arnone, A., et al; Highly Diastereoselective Methylene Transfer from Diazomethane to the Carbonyl of Keto Sulfoxides. A General Approach to Synthetically Versatile Fluorine-Containing Chiral Building Blocks; Tetrahedrone 54 (1998) 11841-11860.
Ambrose, P., et al: Stereoselective Synthesis of Trifluoro- and Monofluoro-Analogues of Frontalin and Evaluation of their Biologic Activity; J. Org. Chem. 2001, 66, 8336-8343.
Lee Thomas Wai-Ho
Proudfoot John Robert
Boehringer Ingelheim Pharmaceuticals Inc.
Devlin Mary-Ellen M.
Morris Michael P.
Solola Taofiq
Witkowski Timothy X.
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