Antipicornaviral compounds and compositions, their...

Details Antipicornaviral compounds and compositions, their... Antipicornaviral compounds and compositions, their...

2006-02-07

2006-02-07

Lukton, David (Department: 1653)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

C514S018700, C514S351000, C514S378000, C514S423000, C530S331000, C546S329000, C548S248000

Reexamination Certificate

active

06995142

ABSTRACT:
Peptido and peptidomimetic compounds of the formula:wherein the formula variables are as defined in the disclosure, advantageously inhibit or block the biological activity of the picornaviral 3C protease. These compounds, as well as pharmaceutical compositions containing these compounds, are useful for treating patients or hosts infected with one or more picornaviruses, such as RVP. Intermediates and synthetic methods for preparing such compounds are also provided.

REFERENCES:
patent: 5374623 (1994-12-01), Zimmerman et al.
patent: 5498616 (1996-03-01), Mallamo et al.
patent: 5856530 (1999-01-01), Webber et al.
patent: 5962487 (1999-10-01), Webber et al.
patent: 6020371 (2000-02-01), Dragovich et al.
patent: 6331554 (2001-12-01), Dragovich et al.
patent: 0 201844 (1986-11-01), None
patent: 0 632051 (1994-06-01), None
patent: WO 92/22570 (1992-12-01), None
patent: WO 94/04172 (1994-03-01), None
patent: WO 95/15749 (1995-06-01), None
patent: WO 95/23222 (1995-08-01), None
patent: WO 95/31433 (1995-11-01), None
patent: WO 97/19231 (1997-05-01), None
patent: WO 97/31937 (1997-09-01), None
patent: WO 97/43305 (1997-11-01), None
patent: WO 97/49668 (1997-12-01), None
patent: WO 98/43950 (1998-10-01), None
patent: WO 99/31122 (1999-06-01), None
patent: WO 99/57135 (1999-11-01), None
patent: WO 00/78708 (2000-12-01), None
patent: WO 01/10894 (2001-02-01), None
patent: WO 01/14329 (2001-03-01), None
patent: WO 01/14576 (2001-03-01), None
patent: WO 01/40189 (2001-06-01), None
Birch et al., “Purification of Recombinant Human Rhinovirus 14 3C Protease Expressed inEscherichia coli”, Protein Expression and Purification, 6, 609-618 (1995).
Kaldor et al., “Glutamine-Drived Aldehydes For The Inhibition Of Human Rhinovirus 3C Protease”, Bioorganic & Medicinal Chemistry Letters, 5 (17), 2021-2026 (1995).
Kong et al., “Synthesis and Evaluation of Peptidyl Michael Acceptors That Inactivate Human Rhinovirus 3C Protease and Inhibit Virus Replication”, J. Med. Chem., 41, 2579-2587 (1998).
Murray et al., “The Enantiospecific Synthesis Of Novel Lysine Analogues Incorporating a Pyrrolidine Containing Side Chain”, Tetrahedron Letters, 39, 6721-6724 (1998).
Webber et al., “Design, Synthesis, and Evaluation of Nonpeptidic Inhibitors of Human Rhinovirus 3C Protease”, J. Med. Chem., 39, 5072-5082 (1996).
Hoffman, R.V., Tao, J. “A Simple, Stereoselective Synthesis of Ketomethylene Dipeptide Isosteres”, Tetrahedron(1997) vol. 53, No. 21, pp. 7119-7126.
Webber et al., “Tripeptide Aldehyde Inhibitors of Human Rhinovirus 3C Protease: Design, Synthesis, Biological Evaluation, and Cocrystal Structure Solution of P1Glutamine Isosteric Replacements”, J. Med. Chem., 41, 2786-2805 (1998).
Askin et al., “Highly Diastereoselective Alkylations of Chiral Amide Enolates: New Routes to Hydroxyethylene Dipeptide Isostere Inhibitors of HIV-1 Protease”,J. Org. Chem., 57, 2771-2773 (1992).
Bradbury et al., “1,2,4-Triazolo[4,3-a]pyrazine Derivatives with Human Renin Inhibitory Activity. 2. Synthesis, Biological Properties and Molecular Modeling of Hydroxyethylene Isotere Derivatives”,J. Med. Chem., 33, 2335-2342 (1990).
Bradbury et al., “An Efficient Synthesis of the γ-Lactone Corresponding to a Hydroxyethylene Dipeptide Isostere Using Stereoelective Bromolactonisation of a Chiral Acyloxazolidinone”, Tetrahedron Letters, 30, 3845-3848 (1989).
Chida et al., “Total Synthesis and Absolute Configuration of Bengamide A”,J. Chem. Soc. Commun., 1064-1066 (1992).
Diana et al., “Picornavirus Inhibitors: Trifluoromethyl Substitution Provides a Global Protective Effect against Hepatic Metabolism”,J. Med. Chem., 38, 1355-1371 (1995).
Dondoni et al., Thiazole-Based Stereoselective Routes to Leucine and Phenylalanine Hydroxyethylene Dipeptide Isotere Inhibitors of Renin and HIV-1 Aspartic Protease†,J. Org. Chem., 60, 7927-7933 (1995).
Herold et al., “A Versatile and Stereocontrolled synthesis of Hydroxyethylene Dipeptide Isoteres”,J. Org. Chem., 54. 1178-1185 (1989).
Hoffman et al., “A Simple, Stereoselective Synthesis of Ketomethylene Dipeptide Isosteres”, Tetrahedron, 53, 7119-7126 (1997).
Jones et al., “A Short Stereocontrolled Synthesis of Hydroxyethylene Dipeptide Isosteres”, J. Org. Chem., 58, 2286-2290 (1993).
Liu et al., “Structure-Activity Relationships for Inhibition of Papain by Peptide Michael Acceptors”, J. Med. Chem., 35, 1067-1075 (1992).
Luly et al., “A Synthesis of Protected Aminoalkyl Epoxides from α-Amino Acids”, J. Org. Chem., 52, 1487-1492 (1987).
McWilliams et al., “Tandem Asymmetric Transformations: An Asymmetric 1,2-Migration from a Higher Order Zincate Coupled with a Stereoslective Homoaldol Reaction”, J. Am. Chem. Soc., 118, 11970-11971 (1996).
Pegorier et al., “A General Stereocontrolled Synthesis of Hydroxyethylene Dipeptide Isosteres”, Tetrahedron Letters, 36, 2753-2756 (1995).
Thompson et al., “Carboxyl-Modified Amino Acids and Peptides as Protease Inhibitors”, J. Med. Chem., 29, 104-111 (1986).
Wuts et al., “Synthesis of the Hydroxyethylene Isostere of Leu-Val”, J. Org. Chem., 57, 6696-6700 (1992).
Hanzlik et al., “Communications to the Editor”, Journal of Medicinal Chemistry, 27(6), 711-712 (1984).
Venkatraman et al., “Synthesis of Potential Inhibitors of Human Rhinovirus 3C Protease”, The Second Winter Conference on Medicinal and Bioorganic Chemistry, Jan. 26-31, 1997, Steamboat Springs, Colorado.

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