Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-03-14
2009-12-22
Berch, Mark L (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C424S009200
Reexamination Certificate
active
07635693
ABSTRACT:
The subject invention concerns N-thiolated β-lactam compounds of formula A,wherein R1is a hydrocarbon group having 1-8 carbon atoms; R3is an organothio group; and R4is alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cycloalkenyl, or heterocycloalkenyl, and analogs and pharmaceutically acceptable salts, esters and amides thereof. The subject invention also concerns methods for inducing tumor cell death or inhibiting tumor cell proliferation, and methods for inducing DNA damage, inhibiting DNA replication, activating p38 MAP kinase, or activating caspase cascade activation, or releasing cytochrome C from mitochondria into the cytoplasm in a tumor cell. Methods for treating cancer using N-thiolated β-lactam compounds, as well as pharmaceutical compositions comprising the same are further disclosed.
REFERENCES:
patent: 4938949 (1990-07-01), Borch et al.
patent: 5142039 (1992-08-01), Blaszczak et al.
patent: 5338861 (1994-08-01), Botta et al.
patent: 6476015 (2002-11-01), Turos et al.
patent: 6946458 (2005-09-01), Turos
patent: 2003/0191108 (2003-10-01), Turos
Coates, Bioorganic & Medicinal Chemistry, vol. 11, Issue 2, Jan. 2003, pp. 193-196.
An, B. and Q. P. Dou “Cleavage of Retinoblastoma Protein during Apoptosis: An Interleukin 1β-converting Enzyme-like Protease as Candidate,”Cancer Research, Feb. 1, 1996, vol. No. 56, pp. 438-442.
An, B. et al. “Novel dipeptidyl proteasome inhibitors overcome Bcl-2 protective function and selectivity accumulate the cyclin-dependent kinase inhibitor p27 and induce apoptosis in transformed, but not normal, human fibroblasts,”Cell Death and Differentiation, 1998, vol. No. 5, pp. 1062-1075.
Desoize, B. “Anticancer Drug Resistance and Inhibition of Apoptosis,”Anticancer Research, 1994, vol. No. 14, pp. 2291-2294.
Dou, Q. P. “Putative roles of retinoblastoma protein in apoptosis,”Apoptosis, 1997, vol. No. 2, Issue No. 1, pp. 5-18.
Drexler, H. G. et al. “Continuous hematopoietic cell lines as model systems for leukemia—lymphoma research,”Leukemia Research, 2000, vol. No. 24, pp. 881-911.
Earnshaw, W. C. “Nuclear changes in apoptosis,”Current Opinion in Cell Biology, 1995, vol. No. 7, pp. 337-343.
Fattman, C. L. et al. “Sequential two-step cleavage of the retinoblastoma protein by caspase-3/-7 during etoposide-induced apoptosis,”Oncogene, 2001, vol. No. 20, pp. 2918-2926.
Fisher, D. E. “Apoptosis in Cancer Therapy: Crossing the Threshold,”Cell, Aug. 26, 1994, vol. No. 78, pp. 539-542.
Gao, G. and Q. P. Dou “N-Terminal Cleavage of Bax by Calpain Generates a Potent Proapoptotic 18-kDa Fragment that Promotes Bcl-2-Independent Cytochrome C Release and Apoptotic Cell Death,”Journal of Cellular Biochemistry, 2000, vol. No. 80, pp. 53-72.
Green, D. R. and J. C. Reed “Mitochondria and Apoptosis,”Science, Aug. 28, 1998, vol. No. 281, pp. 1309-1312.
Harrison, D. J. “Molecular Mechanisms of Drug Resistance in Tumours,”Journal of Pathology, 1995, vol. No. 175, pp. 7-12.
Jänicke, R. U. et al. “Specific cleavage of the retinoblastoma protein by an ICE-like protease in apoptosis,”The EMBO Journal, 1996, vol. No. 15, Issue No. 24, pp. 6969-6978.
Kummer, J. L. et al. “Apoptosis Induced by Withdrawal of Trophic Factors is Mediated by p38 Mitogen-activated Protein Kinase,”The Journal of Biological Chemistry, 1997, vol. No. 272, Issue No. 33, pp. 20490-20494.
Lazebnik, Y. A. et al. “Cleavage of poly(ADP-ribose) polymerase by a proteinase with properties like ICE,”Nature, Sep. 22, 1994, vol. No. 371, pp. 346-347.
Lee, S. et al “Apoptosis and signal transduction: clues to a molecular mechanism,”Current Opinion in Cell Biology1993, vol. No. 5, pp. 286-291.
Li, H. et al. “Cleavage of BID by Caspase 8 Mediates the Mitochondrial Damage in the Fas Pathway of Apoptosis,”Cell, Aug. 21, 1998, vol. No. 94, pp. 491-501.
Martin, S. J. and D. R. Green “Protease Activation during Apoptosis: Death by a Thousand Cuts?”Cell, Aug. 11, 1995, vol. No. 82, pp. 349-352.
Menter, D. G. et al “Selenium Effects on Prostate Cell Growth,”Cancer Epidemiology, Biomarkers&Prevention, Nov. 2000, vol. No. 9, pp. 1171-1182.
Nam, S. et al “Ester Bond-containing Tea Polyphenols Potently Inhibit Proteasome Activity in Vitro and in Vivo,”The Journal of Biological Chemistry, Apr. 20, 2001, vol. No. 276, Issue No. 16, pp. 13322-13330.
Pfundt, R. et al. “In situ demonstration of phosphorylated c-jun and p38 MAP kinase in epidermal keratinocytes following ultraviolet B irradiation of human skin,”Journal of Pathology, 2001, vol. No. 193, pp. 248-255.
Raingeaud, J. et al. “Pro-inflammatory Cytokines and Environmental Stress Cause p38 Mitogen-activated Protein Kinase Activation by Dual Phosphorylation on Tyrosine and Threonine,”The Journal of Biological Chemistry, Mar. 31, 1995, vol. No. 270, Issue No. 13, pp. 7420-7426.
Ren, X. et al. “Studies on Nonconventionally Fused Bicyclic β-Lactams,”J. Org. Chem., 1998, vol. No. 63, pp. 8898-8917.
Sanchez-Prieto, R. et al. “A Role for the p38 Mitogen-activated Protein Kinase Pathway in the Transcriptional Activation of p53 on Genotoxic Stress by Chemotherapeutic Agents,”Cancer Research, May 1, 2000, vol. No. 60, pp. 2464-2472.
Smith, D. M. and Q. P. Dou “Green tea polyphenol epigallocatechin inhibits DNA replication and consequently induces leukemia cell apoptosis,”International Journal of Molecular Medicine, 2001, vol. No. 7, pp. 645-652.
Smith, D. M. et al. “A Novel β-Lactam Antibiotic Activates Tumor Cell Apoptotic Program by Inducing DNA Damage,”Molecular Pharmacology, 2002, vol. No. 61, Issue No. 6, pp. 1348-1358.
Staudinger, H. “Diphenylketen,” Mittheilungen aus dem chemischen Institut der Universitat Strassburg i. E.,Zur Kenntniss der Ketene, 1907 (1stedition), pp. 51-123.
Thornberry, N. A. and Y. Lazebnik “Caspases: Enemies Within,”Science, Aug. 28, 1998, vol. No. 281, pp. 1312-1316.
Turos, E. et al “N-Thiolated Bicyclic and Monocyclic β-Lactams,”Tetrahedron, 2000, vol. No. 56, pp. 5571-5578.
Watabe, M. et al. “MT-21 is a Synthetic Apoptosis Inducer that Directly Induces CytochromecRelease from Mitochondria,”Cancer Research, Sep. 15, 2000, vol. No. 60, pp. 5214-5222.
Wu, G. Y. and C. H. Wu “Receptor-mediated in Vitro Gene Transformation by a Soluble DNA Carrier System,”The Joumal of Biological Chemistry, Apr. 5, 1987, vol. No. 262, Issue No. 10, pp. 4429-4432.
Binder, S. et al. “Emerging Infectious Diseases: Public Health Issues for the 21stCentury”Science, May 21, 1999, vol. No. 284, pp. 1311-1313.
Boyd, D.B. et al. “Heteroatom-Activated β-Lactam Antibiotics: Considerations of Differences in the Biological Activity of [[3(S)-(Acylamino)-2-oxo-1-azetidinyl]oxy]acetic Acids (Oxamazins) and the Corresponding Sulfur Analogues (Thiamazins)”J. Med. Chem., 1987, vol. No. 30, pp. 528-536.
Breuer, H. et al. “[(2-oxo-1-azetidinyl)oxy]acetic Acids: A New Class of Synthetic Monobactams”J. Antibiotics, Jun. 1985, vol. No. 38, Issue No. 6, pp. 813-818.
Champney, W.S. and C.L. Tober “Evernimicin (SCH27899) Inhibits both Translation and 50S Ribosomal Subunit Formation inStaphylococcus aureusCells”Antimicrob. Agents and Chemotherapy, Jun. 2000, vol. No. 44, Issue No. 6, pp. 1413-1417.
Lim, D.V. et al. “Radiolabeling of and Macromolecular Syntheses inNeissetia gonorrhoeaeTypes 1 and 4”Applied and Envion. Microbiology, Feb. 1977, vol. No. 33, Issue No. 2, pp. 328-333.
Long, T.E. and E. Turos “N-Thiolated β-Lactams”Curr. Med. Chem.-Anti-Infective Agents, 2002, vol. No. 1, Issue No. 3, pp. 251-268.
Slusarchyk, W.A. et al. “Monobactams: Ring Activating N-1-Substituents in Monocyclic β-La
Dou Q. Ping
Smith David M.
Turos Edward
Berch Mark L
Saliwanchik Lloyd & Saliwanchik
University of South Florida
LandOfFree
Methods for preventing and treating cancer using N... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Methods for preventing and treating cancer using N..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Methods for preventing and treating cancer using N... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4089118