Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2005-05-10
2005-05-10
Celsa, Bennett (Department: 1639)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C514S422000
Reexamination Certificate
active
06891046
ABSTRACT:
The invention provides a new process for the preparation of polypyrrolinones (I) of various sizes which have found to be useful peptidomimetics. One aspect of the invention is a new process utilizing α-amino-α-substituted-valerolactones as synthons. A second aspect of the invention is a process for the synthesis of polypyrrolinones using solid-phase techniques.
REFERENCES:
patent: 5514814 (1996-05-01), Hirschmann et al.
patent: 5770732 (1998-06-01), Hirschmann et al.
patent: 6034247 (2000-03-01), Smith, III et al.
Hess, D.B et al., “Readily Accessible 12-I-5(superscript 1) Oxidant for the Conversion of Primary and Secondary Alcohols to Aldehydes and Ketones” J. Org. Chem. 1983, 48, 4155-4158.
Ireland Robert E., et al., “An Improved Procedure for the preparation of the Dess-Martin Periodinane”; J. Org. Chem. 1993, 58, 2899.
Look, Gary C. et al., “Trimethylorthoformate: A Mild and Effective Dehydrating Reagent for Solution and Solid Phase Imine Formation.” Tetrahedron Letters, vol. 36, No. 17, pp. 2937-2940, 1995.
Smith, Amos B. et al., “Design and Synthesis of a Competent Pyrrolinon-Peptide Hybrid Ligand for the Class II Major Histocompatibility Complex Protein HLA-DR1”, J. Am. Chem. Soc. 1999, 121, 9286-9298.
Thompson, Wayne J. et al., “Synthesis and Antiviral Activity of a Series of HIV-1 Protease Inhibitors with Functionality Tethered to the P(subscript 1) or P(subscript 1 accent) Phenyl Substituents: X-ray Crystal Structure Assisted Design”, J. Med. Chem. 1992, 35, 1685-1701.
Smith, Amos B. III et al. “Design, Synthesis, and Evaluation of a Pyrolinone-Peptide Hybrid Ligand for the Class II MHC protein HLA-DR1” J. Am. Chem. Soc. 1998, 120, 12704-12705.
R. Hirschmann et al., “Some Interactions of Macromolecules with Low Molecular Weight Ligands. Recent Advances in Peptidomimetic Research”, New Perspectives in Drug Design, Academic Press, 1995.
Smith, Amos B. III, et al., “An Orally Bioavailable Pyrrolinone Inhibitor of HIV-1 Protease: Computational Analysis and X-ray Crystal Structure of the Enzyme Complex”, J. Med. Chem. 1997, 40, 2440-2444.
Smith, Amos, III, et al., “Pyrrolinone-Based HIV Protease Inhibitors. Design, Synthesis, and Antiviral Activity: Evidence for Improved Transport”, J. Am. Chem. Soc., vol. 117, No. 1995.
Smith, Amos B. III, et al., “Design and Synthesis of Peptidomimetic Inhibitors of HIV-1 Protease and Renin. Evidence for Improved Transport”, Journal of Medicinal Chemistry, 1994, vol. 37, No. 2, 215-218.
Smith, Amos B. III, et al., “Molecular Modeling, Synthesis, and Structures of N-Methylated 3,5-Linked Pyrrolin-4-ones Toward the Creation of a Privileged Nonpeptide Scaffold”, Bioorganic & Medicinal Chemistry 7 (1999) 9-22.
Smith, Amos B., III, et al., “De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based B-Strand Peptidemimetics”, J. Am. Chem. Soc., vol. 116, No. 22, 1994 pp. 9947-9962.
Smith, Amos B., III, et al., Design, Synthesis, and Crystal Structure of a Pyrrolinone-Based Peptidomemetic Possesing the Conformation of a B-Strand: Potential Application to the Design of Novel Inhibitors of Proteolytic Enzymes, J. Am. Chem. Soc., vol. 114, No. 26, 1992 pp. 10672-10674.
DeWitt, Sheila H. et al., “Combinatorial Organic Synthesis Using Parke-Davis's DIVERSOMER Method”, Acc. Chem. Res. 1996, 29, 114-122.
Thompson, et al., “Synthesis and Applications of Small Molecule Libraries”, Chem. Rev. 1996, 96, 555-600.
Fruchtel, Jorg S., et al., “Organic Chemistry on Solid Supports”, Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42.
Atherton, E. et al., “Solid Phase Peptide Synthesis, a Practical Approach” 1989 pp 14-23.
Obrecht, D. et al., “Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compound Libraries”, 1998, pp 85-101.
Hirschmann Ralph F.
Ikumura Hiroyuki
Liu Hu
Smith, III Amos B.
Celsa Bennett
Epperson Jon D.
Mathews, Collins Shepherd & McKay, P.A.
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