Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2005-03-15
2005-03-15
Gitomer, Ralph (Department: 1651)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
Reexamination Certificate
active
06867334
ABSTRACT:
The purification and structure elucidation of several products of the metabolism of Et 743 by human cytochrome CYP3A4 have been accomplished. These compounds are abbreviated herein as “ETM” followed by a numeric value which represents the approximate molecular weight. Three compounds have been identified to date, namely ETM 305, ETM 775 and ETM 204. The structures of these ecteinascidin metabolites are as follows:
REFERENCES:
patent: 5089273 (1992-02-01), Rinehart et al.
patent: 5149804 (1992-09-01), Rinehart et al.
patent: 5256663 (1993-10-01), Rinehart et al.
patent: 5478932 (1995-12-01), Rinehart et al.
patent: 5654426 (1997-08-01), Rinehart et al.
patent: 5721362 (1998-02-01), Corey et al.
patent: 5985876 (1999-11-01), Rinehart et al.
patent: 6124292 (2000-09-01), Corey
patent: 6316214 (2001-11-01), Rinehart et al.
patent: 6348467 (2002-02-01), Corey
patent: 6686470 (2004-02-01), Danishefsky et al.
patent: 20030216397 (2003-11-01), Flores et al.
patent: 20040002602 (2004-01-01), Francesch et al.
patent: 20040019056 (2004-01-01), Manzanares et al.
patent: 0 309 477 (1991-11-01), None
patent: 59-225189 (1984-12-01), None
patent: 60-84288 (1985-05-01), None
patent: WO 8707610 (1987-12-01), None
patent: WO 9209607 (1992-06-01), None
patent: WO 9812198 (1998-03-01), None
patent: WO 9846080 (1998-10-01), None
patent: WO 9958125 (1999-11-01), None
patent: WO 0018233 (2000-04-01), None
patent: WO 0069862 (2000-11-01), None
patent: WO 0177115 (2001-10-01), None
patent: WO 0187894 (2001-11-01), None
patent: WO 0187895 (2001-11-01), None
Arai, T. et al., “The Structure of a Novel Antitumor Antibiotic, Saframycin A”,Experientia, vol. 36, pp. 1025-1027 (1980).
Arai, Tadashi et al., “Increased Production of Saframycin A and Isolation of Saframycin S”,The Journal of Antibiotics, vol. XXXIII, No. 9, pp. 951-960 (1980).
Arai, Tadashi et al., “Directed Biosynthesis of New Saframycin Derivatives with Resting Cells ofStreptomyces lavendulae”, Antimicrobial Agents and Chemotherapy, vol. 28, No. 1, pp 5-11 (1985).
Arai, Tadashi et al., “Isoquinolineinones from Actinomycetes and Sponges”,The Alkaloids Chemistry and Pharmacology, vol. XXI, pp. 56-100 (1983).
Arai, Tadashi et al., “New Antibiotics, Safraycins A, B, C, D and E”,The Journal of Antibiotics, vol. XXX, No. 11, pp. 1015-1018 (1977).
Arai, Tadashi et al., “Increased Production of Saframycin A and Isolation of Saframycin S”,The Journal of Antibiotics, vol. XXXIII, No. 9, pp. 951-960 (1980).
Asaoka, Takemitsu et al., “A New Saframycin, Saframycin R”,The Journal of Antibiotics, vol. XXXV, No. 12, pp. 1708-1710 (1982).
Barton, Derek H.R. et al., “Synthesis and Properties of a Series of Sterically Hindered Guanidine Bases1”,Journal of the Chemical Society Perkin Transactions I, No. 9, pp. 2085-2090 (1982).
Brown, J.M., “NCI's Anticancer Drug Screening Program May Not Be Selecting for Clinically Active Compounds,” Oncol. Res. 9(5):213-215 (1997).
Cable, Karl M. et al., “The Biosynthesis of Tuberin from Tyrosine and Glycine; Observations on the Stereochemistry Associated with the Conversion of Glycine through Methylenetetrahydrofolate into Methenyltetrahydrofolate”,Journal of the Chemical Society Perkins Transactions I, No. 7, pp. 1593-1598 (1987).
Cooper, Raymond et al., “Structure of the Quinone Antibiotic EM5519 and the Behavior of Quinones in Fast Atom Bombardment Mass Spectrometry”,The Journal of Antibiotics, vol. XXXVIII, No. 1, pp. 24-30 (1985).
Corey, E.J. et al., “Enantioselective Total Synthesis of Ecteinascidin 743”,Journal of the American Chemical Society, vol. 118, No. 38, pp. 9202-9203 (1996).
Cuevas, Carmen et al., “Synthesis of Ecteinascidin ET-743 and Phthalascidin Pt-650 from Cyanosafracin B”,Organic Letters, vol. 2, No. 16, pp. 2545-2548 (2000).
Draetta, G. and Pagano, M., “Annual Reports in Medicinal Chemistry, vol. 31,” Academic Press, San Diego, pp. 241-246 (1996).
Eckhardt, S.G. et al., “Activity of ecteinascidin, a novel marine cytotoxic, against primary human tumor colony-forming units”,Proceedings of the American Association for Cancer Research, vol. 37, #2791, pp. 409 (1996).
Faircloth, G. et al., “Ecteinascidin-743 (ET743): in vitro (IVT) and in vivo (INV) Results in Tumor Models”,The European Journal of Cancer, vol. 32A, Supp. 1, #24 O, pp. S5 (1996).
Flam, Faye, “Chemical Prospectors Scour the Seas for Promising Drugs”,Science, vol. 266, pp. 1324-1325 (1994).
Frincke, James M. et al., “Antimicrobial Metabolites of the Sponge Reniera sp.”,Journal of the American Chemical Society, vol. 104, pp. 265-269 (1982).
Fukuyama, Tohru et al., “Total Synthesis of (±)-Saframycin A”,Journal of American Chemical Society, vol. 112, pp. 3712-3713 (1990).
Fukuyama, Tohru et al., “Stereocontrolled Total Synthesis of (±)-Saframycin B”,Journal of American Chemical Society, vol. 104, pp. 4957-4958 (1982).
Garcia-Rocha, M. et al., “Characterisation of antimitotic products from marine organisms that disorganize the microtubule network: ecteinascidin 743, isohomohalichondrin-B and LL-15”,British Journal of Cancer, vol. 73, pp. 875-883 (1996).
Goldwasser, F, et al. “Characterization of ecteinascidin 743-induced DNA damages in cells”,Proceedings of the American Association for Cancer Research, vol. 39, #4066, pp. 598 (1998).
Guan, Yue et al., “Molecular and Crystal Structures of Ecteinascidines: Potent Antitumor Compounds from the Caribbean Tunicate Ecteinascidia Turbinata”,Journal of Biomolecular Structure&Dynamics, vol. 10, No. 5, pp. 793-818 (1993).
Gulavita, Nanda K., et al., “Antimicrobial Constituents of a Sponge-Nudibranch Pair from Sri Lanka”,Bioactive Compounds from Marine Organisms, Oxford & IBH Publishing Co. Pvt. Ltd., pp. 229-233 (1991).
He, Hai-yin et al., “Renieramycins E and F from the Sponge Reniera sp.: Reassignment of the Stereochemistry of the Renieramycins”,The Journal of Organic Chemistry, vol. 54, No. 24, pp. 5822-5824 (1989).
Hendricks, H.R. et al., “High antitumor activity of ET743 in human tumor xenograft models”,Proceedings of the American Association for Cancer Research, vol. 37, #2653, pp. 389 (1996).
Ikeda, Yoshifumi et al., “Safracins, New Antitumor Antibiotics I. Producing Organism, Fermentation and Isolation”,The Journal of Antibiotics, Vol. XXXVI, No. 10, pp. 1279-1283 (1983).
Ikeda, Yoshifumi et al., “Safracins, New Antitumor Antibiotics I. Producing Organism, Fermentation and Isolation”,The Journal of Antibiotics, vol. XXXVI, No. 10, pp. 1284-1289 (1983).
Koenig, Karl E., “The Applicability of Asymmetric Homogeneous Catalytic Hodrogenation”,Asymmetric Synthesis, Ed. Morrison, Academic Press, Inc., Orlando, FL, vol. 5, pp. 71 (1985).
Kofron, William G. et al., “A Convenient Method for Estimation of Alkyllithium Concentrations”,The Journal of Organic Chemistry, vol. 41, No. 10, pp. 1879-1880 (1976).
Kubo, Akinori et al., “Structure of Saframycin D, A New Dimeric Isoquinolinequinone Antibiotic”,Chem. Pharm. Bull., vol. 35, No. 1, pp. 440-442 (1987).
Kuffel, M.J. et al., “Cytochrome P450 catalyzed metabolism of Ecteinascidin 743 by rat and human liver microsomes”,Proceedings of the American Association for Cancer Research, vol. 38, #4003, pp. 596 (1997).
Ito, Yoichiro, “High-Speed Countercurrent Chromatography”,Critical Reviews in Analytical Chemistry, vol. 17, No. 1, pp. 65-143 (1986).
Lichter, W. et al., “Biological Activities Exerted by Extracts of Ecteinascidia Turbinata”,Food and Drugs from the Sea Proceedings, pp. 117-127 (1972).
Lown, J. William et al., “Structure and Confirmation of Saframycin R Determined by High Field1H and13C NMR and its Interactions with DNA in Soloution”,The Journal
Floriano Pablo
Gravalos Lola Garcia
Morales Jose J.
Reid Joel
Reymundo Isabel
Fish & Richardson P.C.
Gitomer Ralph
Pharma Mar S.A.
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