Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2006-11-13
2011-11-08
Davis, Zinna Northington (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S061000
Reexamination Certificate
active
08053443
ABSTRACT:
N-Substituted indenoisoquinoline compounds, and pharmaceutical formulations of N-substituted indenoisoquinoline compounds are described. Also described are processes for preparing N-substituted indenoisoquinoline compounds. Also described are methods for treating cancer in mammals using the described N-substituted indenoisoquinoline compounds or pharmaceutical formulations thereof.
REFERENCES:
patent: 5597831 (1997-01-01), Michalsky et al.
patent: WO00/21537 (2000-04-01), None
West, Anthony R., Solid State Chemistry and its Applications, Wiley, New York, 1988, pp. 358 & 365.
International Search Report and Written Opinion for PCT/US2006/043933 filed Nov. 13, 2006.
Kucerova, T., et al., “Solovolysis of 0-acyl-10hydroxy-10dihydro-indeno[1,2-c]Isoquinolin- 5,11-diones”, 1979, Database CA, Chemical Abstracts Service, Database Accession No. 1980:22814.
Cushman, Mark, et al., “Synthesis of a New Indeno[1,2-c]Isoquinolines: Cytotoxic Non-Camptothecin Topoisomerase I Inhibitors”, 2000,Journal of Medicinal Chemistry, vol. 43, No. 20, pp. 3688-3698.
Jayaraman, Muthusamy, et al., “Synthesis of New Dihydroindeno[1-2-c]Isoquinolone and Indenoisoquinolinium Chloride Topoisomerase I Inhibitors Having High In Vivo Anticancer Activity in the Hollow Fiber Animal Model”, 2002,Journal of Medicinal Chemistry, vol. 45, No. 1, pp. 242-249.
Morrell, Andrew, et al., “Synthesis, of Nitrated Indenoisoquinolines As Topoisomerase I Inhibitors”, 2004,Bioorganic&Medicinal Chemistry Letters, vol. 14, pp. 3659-3663.
Nagarajan, Muthukaman, et al., “Synthesis and Anticancer Activity of Simplified Indenoisoquinoline Topoisomerase I Inhibitors Lacking Substituents on the Aromatic Bag”, 2004,Journal of Medicinal Chemistry, vol. 47, No. 23, pp. 5651-5661.
Strumbert, Dirk, et al., “Synthesis of Cytotoxic Indenoisoquinoline Topoisomerase I Poisons”, 1999,Journal of Medicinal Chemistry, vol. 42, No. 3, pp. 446-457.
Wawzonek, Stanley, “Novel Formation of 11-Ketoindeno[1,2-c]Isocoumarin”, 1968, The Journal of Organic Chemistry, vol. 33, No. 2, pp. 896-897.
Wawzonek, Stanley, “Synthesis of 6-Substituted-6H-Indeno[1,2-c] Isoquinoline-5,11-diones”, 1982, Database CA, Chemical Abstracts Service Database Accession No. 1982:199485.
Staker, B.L.; Hjerrild, K.; Feese, M.D.; Behnke, C.A.; Burgin Jr., A.B.; Stewart, L. “The Mechanism of Topoisomerase I Poisoning by a Camptothecin Analog,”Proc. Natl. Acad. Sci. U.S.A., 2002, 99, 15387-15392.
Pommier, Y.; Pourquier, P.; Fan, Y.; Strumberg, D. “Mechanism of Action of Eukaryotic DNA Topoisomerase I and Drugs Targeted to the Enzyme”,Biochim. Biophys. Acta, 1998, 1400, 83-106.
Kohlhagen, G.; Paull, K.; Cushman, M.; Nagafuji, P.; Pommier, Y., “Protein-Linked DNA Strand Breaks Induced by NSC 314622, a Novel Noncamptothecin Topoisomerase I Poison,”Mol. Pharmacol., 1998, 54, 50-58.
Jaxel, C.; Kohn, K. W.; Wani, M. C.; Wa.., M.C.; Pommier, Y., “Structure-Activity Study of the Actions of Camptothecin Derivatives on Mammalian Topoisomerase I: Evidence for a Specific Receptor Site and a Relation to Antitumor Activity,”Cancer. Rev., 1989, 49, 1465-1469.
Minami, H.; Beijnen, J.H.; Verweij, J.; Ratain, M. J., “Limited Sampling Model for the Area under the Concentration Time Curve of Total Topotecan”,Clin. Cancer Res., 1996, 2, 43-46.
Danks, M.K.; Pawlik, C.A.; Whipple, D.O.; Wolverton, J.S., “Intermittant Exposure of Medulloblastoma Cells to Topotecan Produces Growth Inhibition equivalent to Continuous Exposure,” Clinical Cancer Research, 1997, 3, 1731-1738.
Haas, N.B.; LaCreta, F.P.; Walczak, J.; Hudes, G.R.; Brennan, J.M.; Ozols, R.F.; O'Dwyer, P.J. “Phase 1/Pharmacokinetic Study of Topotecan by 24-Hour Continuous Infusion Weekly,”Cancer Res., 1994, 54, 1220-1226.
Shapiro, S.L.; Geiger, K.; Youlus, J.; Freedman, L., “Indandiones. II. A Modified Dieckmann Reaction,”J. Org. Chem., 1961, 26, 3580-3582.
Pailer, M.; Worther, H.; Meller, A., “Some reactions of 2-aryl-1,3-indandiones”,Monatsh Chem., 1961, 92, 1037-1047.
Freireich, E.J., et al., “Quantitative Comparison to Toxicity of Anticancer Agents in Mouse, Rat, Hamster, Dog, Monkey, and Man”,Cancer Chemother. Rep., 1966, 50 (4), 219-244.
Nagarajan, M.; Xiao, X.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M., “Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Topoisomerase I Inhibitors Featuring Polyamine Side Chains on the Lactam Nitrogen,”J. Med. Chem,. 2003, 46, 5712-5724.
Hollingshead, M.; Plowman, J.; Alley, M.; Mayo, J.; Sausville, E., “The Hollow Fiber Assay,”Contrib. Oncol,. 1999, 54, 109-120.
Plowman, J.; Camalier, R.; Alley, M.; Sausville, E.; Schepartz, S., “US NCI Testing Procedures”Contrib. Onco,l. 1999, 54, 121-135.
Antony et al., “Differential Induction of Topoisomerase I-DNA Cleavage Complexes by the Indenoisoquinoline MJ-III-65 (NSC 706744) and Camptothecin: Base Sequence Analysis and Activity against Camptothecin-Resistant Topoisomerase I,”Cancer Res., 2003, 63, 7428-7435.
Agama Keli K.
Antony Smitha
Cushman Mark S.
Morrell Andrew E.
Nagarajan Muthukaman
Barnes & Thornburg LLP
Davis Zinna Northington
Purdue Research Foundation
The United States of America as represented by the Department of
LandOfFree
N-substituted indenoisoquinolines and syntheses thereof does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with N-substituted indenoisoquinolines and syntheses thereof, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-substituted indenoisoquinolines and syntheses thereof will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4260077