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

1998-05-26

2000-05-23

Ramsuer, Robert W.

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

Organic compounds

Chalcogen in the nitrogen containing substituent

544229, 546 13, 548405, 548953, 558298, 562 7, 514 18, 514 19, A61K 3805, C07F 3805

Patent

active

060667303

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: 5614649 (1997-03-01), Iqbal et al.
Aoyagi, T. and H. Umezawa , "Structures and Activities of Protease Inhibitors of Microbial Origin," in: Proteases and Biological Control, vol. 2, Reich, E., et al., eds., Cold Spring Harbor, NY: Cold Spring Harbor Laboratory Press, pp. 429-454 (1975).
Bachovchin, W. et al., "Nitrogen-15 NMR Spectroscopy of the Catalytic-Triad Histidine of a Serine Protease in Peptide Boronic Acid Inhibitor Complexes," Biochem. 27:7689-7697 (1988).
Berry, S. et al., "Interaction of Peptide Boronic Acids With Elastase: Circular Dichroism Studies," Proteins: Structure, Function, and Genetics 4:205-210 (1988).
Castro, B. et al., "Peptide Coupling Reagents VI. A Novel, Cheaper Preparation of Benzotriazolyloxytris(dimethylamino)phosphonium Hexafluorophosphate (BOP Reagent)," Synthesis 11: 751-752 (1976).
Dick, L. et al., "Degradation of Oxidized Insulin B Chain by the Multiproteinase Complex Macropain (Proteasome)," Biochem. 30:2725-2734 (1991).
Goldberg, A., "The mechanism and functions of ATP-dependent proteases in bacterial and animal cells," Eur. J. Biochem. 203:9-23 (1992).
Goldberg, A. and K. Rock, "Proteolysis, Proteasoms, and antigen presentation," Nature 357:375-379 (1992).
Hershko, A. and A. Ciechanover, "The Ubiquitin System for Protein Degradation," Annu. Rev. Biochem. 61:761-807 (1992).
Kettner, C. and A. Shenvi, "Inhibition of the Serine Proteases Leukocyte Elastase, Pancreatic Elastase, Cathepsin G, and Chymotrypsin by Peptide Boronic Acids," J. Biol. Chem. 259:15106-15114 (1984).
Kettner, C. et al., "Kinetic Properties of the Binding of .alpha.-Lytic Protease to Peptide Boronic Acids, " Biochem. 27:7682-7688 (1988).
Kinder, D. and J. Katzenellenbogen, "Acylamino Boronic Acids and Difluoroborane Analogues of Amino Acids: Potent Inhibitors of Chymotrypsin and Elastase," J. Med. Chem. 28:1917-1925 (1985).
Kinder, D. et al., "Antimetastatic Activity of Boro-Amino Acid Analog Protease Inhibitors against B16BL6 Melanoma in vivo," Invasion Metastasis 12:309-319 (1992).
Murakami, K. and J. Etlinger, "Endogenous inhibitor of nonlysosomal high molecular weight protease and calcium-dependent protease," Proc. Natl. Acad. Sci. USA 83:7588-7592 (1986).
Rechsteiner, M., "Ubiquitin-Mediated Pathways for Intracellular Proteolysis," Ann. Rev. Cell Biol. 3:1-30 (1987).
Rivett, A., "The Multicatalytic Proteinase. Multiple Proteolytic Activities," J. Biol. Chem. 264:12215-12219 (1989).
Rivett, A., "The Multicatalytic Proteinase of Mammalian Cells," Arch. Biochem. Biophys. 268:1-8 (1989).
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 78:761-771 (Sep. 9, 1994).
Sheehan, J. et al., "A Rapid Synthesis of Oligopeptide Derivatives without Isolation of Intermediates," J. Am. Chem. Soc. 87:2492-2493 (1965).
Takahashi, L. et al., "Crystallographic Analysis of the Inhibition of Porcine Pancreatic Elastase by a Peptidyl Boronic Acid: Structure of a Reaction Intermediate," Biochem. 28:7610-7617 (1989).
Tanaka, K. et al., "Proteasomes: Protein and Gene Structures," New Biol. 4:173-187 (1992).
Tsai, D. et al., "Diastereoselection in Reactions of Pinanediol Dichloromethaneboronate," Organometallics 2:1543-1545 (1983).
Tsilikounas, E. et al., "Identification of Serine and Histidine Adducts in Complexes of Trypsin and Trypsinogen with Peptide and NonPeptide Boronic Acid Inhibitors by .sup.1 H NMR Spectroscopy," Biochem. 31:12839-12846 (1992).
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," J. Med. Chem. 38:98-108 (Jan. 6, 1995).

Affiliated with

Also associated with

Rating

Boronic ester and acid compounds, synthesis and uses does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Boronic ester and acid compounds, synthesis and uses, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Boronic ester and acid compounds, synthesis and uses will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1837807