Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Peptide containing doai
Patent
1998-02-20
2000-02-15
Russel, Jeffrey E.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Peptide containing doai
514 14, 514 16, 514 18, 514 23, 514546, 514561, 514562, 514563, 514691, 530300, 530327, 530328, 530330, 530331, 530345, 536 111, 560162, 560255, 560256, 564155, 564161, 564460, 568 42, 568 43, 568305, 568306, 568327, 568374, A61K 3112, A61K 3170, A61K 3804, C07C 49543, C07K 700
Patent
active
060253282
ABSTRACT:
The present invention provides illudin analogs of the general formula I: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 have 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: 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
Anchel, M., et al., "Antibiotic Substances From Basidiomycetes. VII. Clitocybe Illudens", Proceedings of the National Academy of Sciences of the United States of America, 36, 300-305, (May 1950).
Anchel, M., et al., "The Biogenesis of Illudins S and M in Clitocybe Illudens", Phytochemistry, 9, 2339-2343, (1970).
Brandsteterova, E., et al., "HPLC Analysis of Novel Anti-Cancer Agents-Illudens and Their Analogs", J. Liquid Chromatography, 16 (1), 115-125, (1993).
Brandsteterova, E., et al., "HPLC Determination of a New Anticancer Agent (Acylfulvene) in Serum", Neoplasma, 39 (6), 369-373, (1992).
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, 2935-2940, (Jun. 1989).
Curtis, E.A., et al., "An Efficient Dipolar-Cycloaddition Route to the Pterosin Family of Sesquiterpenes", Tetrahedron Letters, vol. 36, No. 12, pp. 1989-1992, (1995).
Dillman, R.O., et al., "Athymic Mouse Model of a Human T-Cell Tumor", Cancer Research, 45, 5632-5636, (Nov. , 1985).
Eva, K.M., et al., "An Efficient Sythesis of Pterosin C and Other Pterosins", Can. J. Chem, 62, 1945-1953, (1984).
French, A.L., et al., "Poisoning with the North American Jack O'Latern Mushroom," Clinical Toxicology, 26 (1&2), 81-88, (1988).
Giovanella, B.C., et al., "Correlation Between Response to Chemotherapy of Human Tumors in Patients and in Nude Mice", Cancer, 52, 1146-1152, (1983).
Giovanella, B.C., et al., "DNA Topoisomerase I-Targeted Chemotherapy of Human Colon Cancer in Xenografts", Science, 246, 1046-1048, (Nov. 1989).
Goldin, A., et al., "Current Results of the Screening Program at the Division of Cancer treatment, National Cancer Institute", Europ. J. Cancer, 17, 129-142, (1981).
Goldin, A., et al., "Historical Development and Current Strategy of the National Cancer Institute Drug Development Program", In: Methods in Cancer Research, vol. XVI, Academic Press, Inc., 165-245, (1979).
Hanson, J.R., et al., "Studies in Terpenoid Biosynthesis. Part XV. Biosynthesis of the Sesquiterpenoid Illuden M", J.C.S. Perkins I, 876-880, (1976).
Hara, M., et al., "6-Deoxyilludin M, a New Antitumor Antiobiotic: Fermentation, Isolation and Structural Identification", The Journal of Antibiotics, 40, 1643-1646, (Nov. 1987).
Harttig, U., et al., "Leaianafulvene, a Sesquiterpenoid Fulvene Derivative from Cultures of Mycena Leaiana", Phytochemistry, 29 (12), 3942-3944, (1990).
Hirono, I., et al., "Repreduction of Acute Bracken Poisoning in a Calf with Ptaquiloside, a Bracken Constituent", The Veterinary Record, 115, Abstract No. 85067284, STN File Server, File Medline, 375-378, (Oct., 1984).
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, 182-186, (1983).
Kawato, Y., et al., "Antitumor Activity of a Camptothecin Derivative, CPT-11, Against Human Tumor Xenografts in Nude Mice", Cancer Chemother. Pharamcol., 28, 192-198, (1991).
Kelner, M.J., et al., "In Vitro and In Vivo Studies on the Anticancer Activity of Dehydroilluden M", Anticancer Research, 15, 873-878, (1995).
Kelner, M.J., et al., "Nonresponsiveness of the Metastatic Human Lung Carcinoma MV522 Xenograft to Conventional Anticancer Agents", Anticancer Research, 15, 867-872, (1995).
Kelner, M.J., et al., "Preclinical Evaluation of Illudens as Anticancer Agents", Cancer Research, 47, 3186-3189, (1987).
Kelner, M.J., et al., "Preclinical Evaluation of Illudens as Anticancer Agents: Basis for Selective Cytotoxicity", J. Natl. Cancer Inst., 82 (19), 1562-1565, (1987).
Matsumoto, T., et al., "An Alternative Synthesis of Illudin M", Tetrahedron Letters, 14, 1171-1174, (1970).
Matsumoto, T., et al., "Synthesis of Illudin S", Tetrahedron Letters, 23, 2049-2052, (1971).
McMorris, T.C., et al., "(Hydroxymethyl) Acyfulvene: An Illuden Derivative with Superior Antitumor Properties", J. Natl. Prod., 59, 896-899, (1996).
McMorris, T.C., et al., "(Hydroxymethyl) acyfulvene: An Illudin Derivative with Superior Antitumor Properties", Chemical Abstracts, abstract No. 196032, vol. 125, No. 15, (Oct. 7, 1996).
McMorris, T.C., et al., "Acylfulvenes, a New Class of Potent Antitumor Agents", Experientia, vol. 51(1), pp. 75-80, (Arp. 21, 1995).
McMorris, T.C., et al., "An Acetal Derivative of Illudin S with Improved Antitimor Activity", Tetrahedron letters, vol. 38, No. 10, pp. 1697-1698, (1977).
McMorris, T.C., et al., "Design and Synthesis of Antitumor Acylfulvenes", J. Org. Chem, vol. 62,, pp. 3015-3018, (1997).
McMorris, T.C., et al., "Fungal Metabolites. The Structures of the Novel Sesquiterpenoids Illudin -S and -M", J. of Amer. Chem. Soc., 87 (7), 1594-1600, (1995).
McMorris, T.C., et al., "On the Mechanism of Toxicity of Illudens: The Role of Gluthathione", Chem. Res. Toxicol., 3, 574-579, (1990).
McMorris, T.C., et al., "Structure and reactivity of Illudens", Tetrahedron, 45 (17), 5433-5440, (1989).
McMorris, T.C., et al., "Structure-Activity Relationships of Illudens: Analogs with Improved Therapeutic Index", J. Org. Chem., 57, 6876-6883, (1992).
McMorris, T.C., et al., "Total Synthesis of hydroxymethylacylfulvene, an antitumor derivatives of illudin S", Chem. Commun., pp. 315-316, (1997).
Padwa, A., et al., "An approach toward the Illudin family of sesquiterpenes using the tandem cyclization-cycloaddition reaction of rhodium carbenoids", J. Org. Chem, vol. 62, pp. 1317-1325, (1997).
Padwa, A., et al., "Generation and Cycloaddition behavior of spirocyclic carbonyl ylides. Application to the synthesis of the Pterosin Family of Sequiterpenes", J. Org. Chem., vol. 61, pp. 73-81, (1996).
Padwa, A., et al., Synthetic studies toward Illudins and Ptaguilosin. A Highly Convergent approach via the dipolar cycloaddition of carbonyl ylides, J. Am. Chem. Soc., Vo. 116, pp. 2667-2668, (1994).
Schabel, F.M., et aL., "Testing Therapeutic Hypotheses in Mice and Man:Observations on the Therapeutic Activity Against Advanced Solid Tumors of Mice Treated with Anticancer Drugs that Have Demonstrated or Potential Clinical Utility for Treatment of Advanced Solid Tumors of Man", In: Methods in Cancer Research, vol. XVII, Academic Press, Inc., pp. 3-50, (1979).
Shinozawa, S., et al., "The Antitumor Effect of Illudin S (Lampterol) Entrapped in Liposome for Mice Inoculated with Ehrich Ascites Tumor Cells", Abstract No. 197682, STN File Server CAS Chemical Abstracts, 90, (1979).
Steel, G.G., et al., "The Response to Chemotherapy of a Variety of Human Tumor Xenografts", Br. J. Cancer, 47, 001-013, (1983).
Tanaka, K., et al., "Metabolism by Rat Liver Cytosol of Illuden S, a Toxic Substance of Lampteromyces Japonicus. II. Characterization of Illuden S-Metabolizing Enzyme", Xenobiotica, 22 (1), 33-39, (1992).
Tanaka, K., et al., "Metabolism of Illuden S, a Toxic Principle of Lampteromyces Japonicus, by Rat Liver. I. Isolation and Identification of Cyclopropane Ring-Cleavage Metabolites", Xenobiotica, 20 (7), 671-681, (1990).
Varki, N.M., eta l., "Cloned Low Metastic Variants from Human Lung Carcinoma Metastases", Anticancer Research, 10, 637-644, (1990).
Vendetti, J.M., et al., "Current NCI Preclinical Antitumor Screening in Vivo: Results of Tumor Panel Screening, 1976-1982, and Future Directions", Advances in Pharmacology and Chemothe
Kelner Michael J.
McMorris Trevor C.
Russel Jeffrey E.
The Regents of the University of California
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