Boronic ester and acid compounds, synthesis and uses

Details Boronic ester and acid compounds, synthesis and uses Boronic ester and acid compounds, synthesis and uses

2011-08-23

2011-08-23

McKane, Joseph K. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C514S064000, C564S008000

Reexamination Certificate

active

08003791

ABSTRACT:
Disclosed herein is a method for reducing the rate of degradation of proteins in an animal, comprising contacting cells of the animal with certain boronic ester and acid compounds. Also disclosed herein are novel boronic ester and acid compounds, their synthesis and uses.

REFERENCES:
patent: 4261868 (1981-04-01), Hora et al.
patent: 4369183 (1983-01-01), Jones et al.
patent: 4499082 (1985-02-01), Shenvi et al.
patent: 4510130 (1985-04-01), Platt et al.
patent: 4537707 (1985-08-01), Severson, Jr.
patent: 4537773 (1985-08-01), Shenvi
patent: 4842769 (1989-06-01), Shulman et al.
patent: 4963655 (1990-10-01), Kinder et al.
patent: 4997929 (1991-03-01), Collins et al.
patent: 5030378 (1991-07-01), Venegas
patent: 5106948 (1992-04-01), Kinder et al.
patent: 5169841 (1992-12-01), Kleeman et al.
patent: 5187157 (1993-02-01), Kettner et al.
patent: 5242904 (1993-09-01), Kettner et al.
patent: 5250720 (1993-10-01), Kettner et al.
patent: 5550262 (1996-08-01), Iqbal et al.
patent: 5574017 (1996-11-01), Gutheil
patent: 5614649 (1997-03-01), Iqbal et al.
patent: 5780454 (1998-07-01), Adams et al.
patent: 5990083 (1999-11-01), Iqbal et al.
patent: 6066730 (2000-05-01), Adams et al.
patent: 6083903 (2000-07-01), Adams et al.
patent: 6297217 (2001-10-01), Adams et al.
patent: 6465433 (2002-10-01), Adams et al.
patent: 6548668 (2003-04-01), Adams et al.
patent: 6617317 (2003-09-01), Adams et al.
patent: 6699835 (2004-03-01), Plamondon et al.
patent: 6713446 (2004-03-01), Gupta
patent: 6747150 (2004-06-01), Adams et al.
patent: 6958319 (2005-10-01), Gupta
patent: 7109323 (2006-09-01), Plamondon et al.
patent: 7119080 (2006-10-01), Adams et al.
patent: 7531526 (2009-05-01), Adams et al.
patent: 2005/0240047 (2005-10-01), Pickersgill et al.
patent: 38 27 340 (1990-02-01), None
patent: 0 145 441 (1985-06-01), None
patent: 0 293 881 (1988-12-01), None
patent: 0 315 574 (1989-05-01), None
patent: 0 354 522 (1990-02-01), None
patent: 0 363 284 (1990-04-01), None
patent: 0 364 344 (1990-04-01), None
patent: 0 381 262 (1990-08-01), None
patent: 0 393 457 (1990-10-01), None
patent: 0 471 651 (1992-02-01), None
patent: 0 478 050 (1992-04-01), None
patent: 0 511 456 (1992-11-01), None
patent: 0 583 536 (1994-02-01), None
patent: WO 88/10266 (1988-12-01), None
patent: WO 91/13904 (1991-09-01), None
patent: WO 92/07869 (1992-05-01), None
patent: WO 92/11850 (1992-07-01), None
patent: WO 92/12140 (1992-07-01), None
patent: WO 92/19707 (1992-11-01), None
patent: WO 92/19709 (1992-11-01), None
patent: WO 93/01828 (1993-02-01), None
patent: WO 93/21213 (1993-10-01), None
patent: WO 93/21214 (1993-10-01), None
patent: WO 94/04653 (1994-03-01), None
patent: WO 94/21668 (1994-09-01), None
patent: WO 94/23045 (1994-10-01), None
patent: WO 95/09858 (1995-04-01), None
patent: WO 95/24914 (1995-09-01), None
patent: WO 95/25533 (1995-09-01), None
U.S. Appl. No. 90/008,475, Adams et al.
U.S. Appl. No. 90/008,476, Adams et al.
Aoyagi, T., et al., “Structures and Activities of Protease Inhibitors of Microbial Origin,”Proteases and Biological Control, vol. 2 (1975), Reich, E., et al., eds., Cold Spring Harbor, NY:Cold Spring Harbor Press, pp. 429-454.
Bachovchin, W., et al., “Nitrogen-15 NMR Spectroscopy of the Catalytic-Triad Histidine of a Serine Protease in Peptide Boronic Acid Inhibitor Complexes,”Biochemistry, vol. 27 (1988), pp. 7689-7697.
Berry, S., et al., “Interaction of Peptide Boronic Acids with Elastase: Circular Dichroism Studies,”Proteins: Structure, Function, and Genetics, vol. 4 (1988) pp. 205-210.
Castro, B., et al., “Peptide Coupling Reagents VI. A Novel, Cheaper Preparation of Benzotriazolyloxytris(dimethylamino)phosphonium Hexafluorophosphate (BOP Reagent),”Synthesis, vol. 11 (1976) pp. 751-752.
Dick, L., et al., “Degradation of Oxidized Insulin B Chain by the Multiproleinase Complex Macropain (Proteasome),”Biochemistry, vol. 30 (1991) pp. 2725-2734.
Goldberg, A., The Mechanism and Functions of AIP-Dependent Proteases in Bacterial and Animal Cells,European Journal of Biochemistry, vol. 203 (1992) pp. 9-23.
Goldberg, A. and Rock, K., “Porteolysis, Proteasomes, and Antigen Presentation,”Nature, vol. 357 (1992) pp. 375-379.
Hershko, A. and Ciechanover, A., “The Ubiquitin System for Protein Degradation,”Annual Review of Biochemistry, vol. 61 (1992) pp. 761-807.
Kettner, C. and Shenvi, A., “Inhibition of the Serino Proteases Leukocyte Elastase, Pancreatic Elastase, Cathepsin, G, and Chymotrypsin by Peptide Boronic Acids,”Journal of Biological Chemistry, vol. 259 (1984) pp. 15106-15114.
Kettner, C., et al., “Kinetic Properties of the Binding of α-Lytic Protease to Peptide Boronic Acids,”Biochemistry, vol. 27 (1988) pp. 7682-7688.
Kinder, D. and Katzenellenbogen, J., “Acylamino Boronic Acids and Difluoroborane Analogues of Amino Acids: Potent Inhibitors of Chymotrypsin and Elastase,”Journal of Medicinal Chemistry, vol. 28 (1985) pp. 1917-1925.
Kinder, D., et al., Antimetastatic Activity of Boro-Amino Acid Analog Protease Inhibitors Against B16BL6 Melanoma in vivo,Invasion Metastasis, vol. 12 (1992) pp. 309-319.
Li, X., et al., “Isolation and Characterization of a Novel Endogenous Inhibitor of the Proteasome,”Biochemistry, vol. 30 (1991) pp. 9709-9715.
Lim, M, et al., “The Solution Conformation of (D)Phe-Pro-Containing Peptides: Implications on the Activity of Ac-(D)Phe-Pro-boroArg-OH, A Potent Thrombin Inhibitor,”Journal of Medicinal Chemistry, vol. 36 (Jun. 25, 1993) pp. 1831-1838.
Matteson, D. and Sadhu, K., “R-1-Acetamido-2-phenylethaneboronic Acid. A Specific Transition-State Analogue for Cymotrypsin,”Journal of the American Chemistry Society, vol. 103 (1981) pp. 5241-5242.
Murakami, K. and Etlinger, J., “Endogenous Inhibitor of Nonlysosomal High Molecular Weight Protease and Calcium-Dependent Protease,”Proceedings of the National Academy of Science USA, vol. 83 (1986) pp. 7588-7592.
Rechsteiner, M., “Ubiquitin-Mediated Pathways for Intracellular Proteolysis,”Annual Review of Cell Biology, vol. 3 (1987) pp. 1-30.
Rivett, A., “The Multicatalytic Proteinase. Multiple Proteolytic Activities,”Journal of Biological Chemistry, vol. 264 (1989) pp. 12215-12219.
Rivett, A., “The Multicatalytic Proteinase of Mammalian Cells,”Archives of Biochemistry and Biophysics, vol. 268 (1989) pp. 1-8.
Rock, K., et al., “Inhibitors of the Proteasome Block the Degradation of Most Cell Proteins and the Generation of Peptides Presented on MHC Class I Molecules,”Cell, vol. 78 (Sep. 9, 1994) pp. 761-771.
Sheehan, J., et al., “A Rapid Synthesis of Oligopeptide Derivatives without Isolation of Intermediates,”Journal of the American Chemical Society, vol. 87 (1965) pp. 2492-2493.
Takahashi, L., et al., “Crystallographic Analysis of the Inhibition of Porcine Pancreatic Elastase by a Peptidyl Boronic Acid: Structure of a Reaction Intermediate,”Biochemistry, vol. 28 (1989) pp. 7610-7617.
Tanaka, K., et al., “Proteasomes: Protein and Gene Structures,”New Biology, vol. 4 (1992) pp. 173-187.
Tsai, D., et al., “Diastereoselection in Reactions of Pinanediol Dichloromethaneboronate,”Organometallics, vol. 2 (1983) pp. 1543-1545.
Tsilikounas, E., et al., “Identification of Serine and Histidine Adducts in Complexes of Trypsin and Trypsinogen with Peptide and NonPeptide Boronic Acid Inhibitors by1H NMR Spectroscopy,”Biochemistry, vol. 31 (1992) pp. 12839-12846.
Veale, C., et al., “Nonpeptidic Inhibitors of Human Leukocyte Elastase. 5. Design, Synthesis, and X-Ray Crystallography of a Series of Orally Active 5-Aminopyrimidin-6-one-Containing Trifluoromethyl Ketones,”Journal of Medicinal Chemsitry, vol. 38 (Jan. 6, 1995) pp. 98-108.
Elgendy, Said, et al., “New Peptide Boronic Acid Inhibitors of Thrombin,”Tetrahedron Letters, vol. 33, No. 29 (1992) pp. 4209-4212.
Amiri, Payman, et al., “Benzamid

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