Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2006-11-16
2009-12-08
Solola, Taofiq A (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C549S339000, C568S373000
Reexamination Certificate
active
07629380
ABSTRACT:
The present invention provides compounds of the general formula I:wherein R1, R2, R3, R4, R5, and R6have any of the values defined in the specification, and pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions comprising compounds of formula I, intermediates and processes useful for preparing compounds of formula I, and methods comprising inhibiting tumor growth or treating cancer by administering one or more compounds of formula I.
REFERENCES:
patent: 4559157 (1985-12-01), Smith et al.
patent: 4608392 (1986-08-01), Jacquet et al.
patent: 4612302 (1986-09-01), Szabo et al.
patent: 4684620 (1987-08-01), Hruby et al.
patent: 4820508 (1989-04-01), Wortzman
patent: 4853371 (1989-08-01), Coy et al.
patent: 4938949 (1990-07-01), Borch et al.
patent: 4992478 (1991-02-01), Geria
patent: 5164526 (1992-11-01), Macher
patent: 5387578 (1995-02-01), Angelucci et al.
patent: 5439936 (1995-08-01), Kelner et al.
patent: 5439942 (1995-08-01), Kelner et al.
patent: 5523490 (1996-06-01), Kelner et al.
patent: 5563176 (1996-10-01), Kelner et al.
patent: 5723632 (1998-03-01), McMorris
patent: 5932553 (1999-08-01), McMorris et al.
patent: 6323181 (2001-11-01), McMorris et al.
patent: 6380403 (2002-04-01), McMorris et al.
patent: 6639105 (2003-10-01), McMorris et al.
patent: 6855696 (2005-02-01), McMorris et al.
patent: 7141603 (2006-11-01), McMorris et al.
patent: 1056704 (2003-05-01), None
patent: 0915819 (2004-05-01), None
patent: 208115 (1993-08-01), None
patent: 72450 (1996-04-01), None
patent: 62-234040 (1987-10-01), None
patent: WO-91/04754 (1991-04-01), None
patent: WO-91/04754 (1991-04-01), None
patent: WO-94/18151 (1994-08-01), None
patent: WO-94/25013 (1994-11-01), None
patent: WO-96/34005 (1996-10-01), None
patent: WO-97/03995 (1997-02-01), None
patent: WO-98/03458 (1998-01-01), None
McMorris, T. C., et al., “Fungal Metabolites. The Structures of the Novel Sesquiterpenoids Illudin-S and -M”,Journal of the American Chemical Society, 87(7), (1965), 1594-1600.
Wolff, M. E.,Burger's Medicinal Chemistry and Drug Discovery, Fifth Edition, vol. 1: Principles and Practice, 785-786.
Anchel, Marjorie , et al., “Antibiotic Substances From Basidiomycetes. VII. Clitocybe Illudens”,Proceedings of the National Academy of Sciences, 36 (5), (1950),300-305.
Anchel, M. , et al., “The Biogenesis of Illudins S and M in Clitocybe Illudens”,Phytochemistry, 9(11), (Nov. 1970) ,2339-2343.
Arap, Wadih , et al., “Cancer Treatment by Targeted Drug Delivery to Tumor Vasculature in a Mouse Model”,Science, 279, (Jan. 16, 1998),377-380.
Brandsteterova, E. , et al., “HPLC Analysis of Novel Anti-Cancer Agents-Illudens and Their Analogs”,Journal of Liquid Chromatography, 16 (1), (1993),115-125.
Brandsteterova, E. , et al., “HPLC Determination of a New Anticancer Agent (Acylfulvene) in Serum”,Neoplasma, 39 (6), (1992),369-373.
Burres, N. S., et al., “Antitumor Activity and Mechanism of Action of the Novel Marine Natural Products Mycalamide-A and -B and Onnamide”,Cancer Research, 49, (Jun. 1989),2935-2940.
Curtis, Erin A., et al., “An Efficient Dipolar-Cycloaddition Route to the Pterosin Family of Sesquiterpenes”,Tetrahedron Letters, 36 (12), (Mar. 1995),1989-1992.
Dillman, R. O., et al., “Athymic Mouse Model of a Human T-Cell Tumor”,Cancer Research, 45, (Nov. 1985),5632-5636.
Eva, K. M., et al., “An Efficient Synthesis of Pterosin C and Other Pterosins”,Canadian Journal of Chemistry, 62 (10), (Oct. 1984),1945-1953.
Fassina, G. , “Oriented Immobilization of Peptide Ligands on Solid Supports”,J. Chromatogr., 591, Abstract Only, Obtained from Chemical Abstracts, Accession No. 1992:174737,(1992),1 p.
French, A. L., et al., “Poisoning with the North American Jack O' Lantern Mushroom”,Clinical Toxicology, 26, (1988),81-88.
Giovanella, B. C., et al., “Correlation Between Response to Chemotherapy of Human Tumors in Patients and in Nude Mice”,Cancer, 52, (1983),1146-1152.
Giovanella, B. C., et al., “DNA Topoisomerase I-Targeted Chemotherapy of Human Colon Cancer in Xenografts”,Science, 246, (Nov. 24, 1989),1046-1048.
Goldin, A. , et al., “Current Results of the Screening Program at the Division of Cancer treatment, National Cancer Institute”,Euro. J. Cancer, 17, (1981),129-142.
Goldin, A. , et al., “Historical Development and Current Strategy of the National Cancer Institute Drug Development Program”, In:Methods in Cancer Research, vol. XVI: Cancer Drug Development, Part A, Chapter V, Academic Press, Inc., New York,(1979),165-245.
Greene, T. W.,Protective Groups in Organic Synthesis, Chapters 4, 5 & 6, John Wiley & Sons, Inc., New York,(1981),114-217.
Hanson, J. R., et al., “Studies in Terpenoid Biosynthesis. Part XV. Biosynthesis of the Sesquiterpenoid Illuden M”,Journal of the Chemical Society, Perkin Transactions I,(1976),876-880.
Hara, M. , et al., “6-Deoxyilludin M, a New Antitumor Antibiotic: Fermentation, Isolation and Structural Identification”,The Journal of Antibiotics, 40, (Nov. 1987),1643-1646.
Harttig, U. , et al., “Leaianafulvene, a Sesquiterpenoid Fulvene Derivative from Cultures of Mycena Leaiana”,Phytochemistry, 29 (12), (1990),3942-3944.
Hirono, I. , et al., “Reproduction of Acute Bracken Poisoning in a Calf with Ptaquiloside, a Bracken Constituent”,The Veterinary Record, 115 (15), (Oct. 1984),375-378.
Inoue, K. , et al., “Antitumor Efficacy of Seventeen Anticancer Drugs in Human Breast Cancer Xenograft (MX-1) Transplanted in Nude Mice”,Cancer Chemother. Pharamacol., 10, (1983),182-186.
Ito, R. K., et al., “Biocompatible Substances with Thromboresistance”, U.S. Patent No. 5,019,393, Abstract Only, Obtained from Chemical Abstracts, Accession No. 1991:499399,(May 28, 1991),1 p.
Kawato, Y. , et al., “Antitumor Activity of a Camptothecin Derivative, CPT-11, Against Human Tumor Xenografts in Nude Mice”,Cancer Chemother. Pharmacol., 28, (1991),192-198.
Kelner, M. J., et al., “In Vitro and In Vivo Studies on the Anticancer Activity of Dehydroilluden M”,Anticancer Research, 15, (1995),873-878.
Kelner, M. J., et al., “Nonresponsiveness of the Metastatic Human Lung Carcinoma MV522 Xenograft to Conventional Anticancer Agents”,Anticancer Research, 15, (1995),867-872.
Kelner, M. J., et al., “Preclinical Evaluation of Illudens as Anticancer Agents”,Cancer Research, 47, (1987),3186-3189.
Kelner, M. J., et al., “Preclinical Evaluation of Illudens as Anticancer Agents: Basis for Selective Cytotoxicity”,J. Natl. Cancer Inst., 82 (19), (1987),1562-1565.
Lu, Jianliang , et al., “An expeditious synthesis of the potent antitumor agent, (+)-hydroxymethylacylfulvene using an allenic Paulson-Khand type cycloaddition”,Proceedings of the 217th ACS National Meeting, abstract only, Anaheim, CA,(Mar. 21-25, 1999),1 p.
Matsumoto, Takeshi , et al., “An Alternative Synthesis of Illudin M”,Tetrahedron Letters, 14, (Mar. 1970),1171-1174.
Matsumoto, .T. , et al., “Synthesis of Illudin S”,Tetrahedron Letters, 23, (May 1971),2049-2052.
McMorris, T. C., et al., “(Hydroxymethyl) Acyfulvene: An Illuden Derivative with Superior Antitumor Properties”,Journal of Natural Products, 59 (9), (Sep. 1996),896-899.
McMorris, T. C., et al., “(Hydroxymethyl)acylfulvene: An Illudin Derivative with Superior Antitumor Properties”,Chemical Abstracts, 125, abstract No. 196032,(Oct. 7, 1996),1 p.
McMorris, T. C., et al., “Acylfulvenes, a New Class of Potent Antitumor Agents”,Experientia, 52 (1), (Apr. 21, 1995),75-80.
McMorris, Trevor C., et al., “An Acetal Derivative of Illudin S with Improved Antitumor Activity”,Tetrahedron letters, 38 (10), (1997),1697-1698.
McMorris, Trevor C., et al., “Design and Synthesis of Antitumor Acylfulvenes”,The Journal of
Kelner Michael J.
McMorris Trevor C.
Schwegman Lundberg & Woessner, P.A.
Solola Taofiq A
The Regents of The University of California
LandOfFree
Antitumor agents does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Antitumor agents, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Antitumor agents will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4112406