Synthesis of...

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

Reexamination Certificate

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C548S300100, C548S301700, C548S302700, C544S106000, C544S111000, C544S132000, C544S358000

Reexamination Certificate

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07470795

ABSTRACT:
Disclosed is a multi-step process for preparing a compound of Formula I:wherein R1to R3are as defined herein. The compounds of formula I inhibit the binding of human intercellular adhesion molecules to the Leukointegrins. As a result, these compounds are useful in the treatment of inflammatory and immune cell-mediated diseases.

REFERENCES:
patent: 6414161 (2002-07-01), Frutos et al.
patent: 6458986 (2002-10-01), Frutos et al.
patent: 6492408 (2002-12-01), Wu et al.
patent: 6844360 (2005-01-01), Kelly et al.
patent: 6852748 (2005-02-01), Kelly et al.
patent: 2002/0028949 (2002-03-01), Frutos et al.
patent: 2006/0025447 (2006-02-01), Wang et al.
patent: WO 01/07440 (2001-02-01), None
patent: WO 2004/041273 (2004-05-01), None
patent: WO 2004/041827 (2004-05-01), None
patent: 2006014828 (2006-02-01), None
Wu, J.P., et al., “Second-Generation Lymphocyte Function-Associated Antigen-1 Inhibitors: 1H-Imidazo [1,2-alpha]imidazol-2-one Derivatives”, J. Med. Chem. 2004, vol. 47, pp. 5356-5366.
Frutos et al.; An improved synthesis of N-aryl-hydantoin LFA-1 antagonists via the enantiospecific alkylation of an isobutyraldehyde-derived imidazolidinone template; Tetrahedron: Asymmetry; 2001; vol. 12; pp. 101-104.
Yee; Self-Regeneration of Stereocenters: A Practicle Enantiospecific Synthesis of LFA-1 Antagonists BIRT-377; Organic Letters; 2000; vol. 2; No. 18; pp. 2781-2783.
Thavonekham; A Practicle Synthesis of Ureas from Phenyl Carbamates; Synthesis; Oct. 1997; pp. 1189-1194.
International Search Report (Form PCT/ISA/220) for PCT/US2007/060552.

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