Compound with antitumor activity and preparation method...

Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing

Reexamination Certificate

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C564S426000, C564S428000, C564S429000, C564S440000, C564S443000, C568S030000, C568S586000, C514S648000, C514S656000, C514S657000

Reexamination Certificate

active

11111406

ABSTRACT:
The present invention provides the diaminophenyladamantane derivatives with antitumor activities and the preparation method therefore. The method includes a step of reacting an aromatic diol with at least one 5-halo-2-nitrophenol in the presence of at least one inorganic base in an organic solvent with a relatively high boiling point.

REFERENCES:
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Database CAPLUS on STN, Acc. No. 2004:738900, Fujimoto et al., JP 2004250438 (Sep. 9, 2004) (abstact).
Sherr, Charles J. , “Cancer Cell Cycles”, Science, vol. 274: 1672-7 (Dec. 1996).
Aigami, Koji, Y. Inamoto, N. Takaishi and K. Hattori, “Biologically Active Polycycloalkanes. 1. Antiviral Adamantane Derivatives”, J. Med. Chem., vol. 18: 713-21 (1975).
Tverdislov, V. A., et al., “Interaction of the Antivirus Agents Remantadine and Amantadine with Lipid Membranes and the Influence on the Curvature of Human Red Cells”, Gen. Physiol. Biophys. 5, 61-75 (1986).
Komhuber, J., J. Bormann, M. Hubers, K. Rusche and P. Riederer, “Effects of the 1-amino-adamantanes at the MK-801-binding site of the NMDA-receptor-gated ion channel: a human postmortem brain study”, European Journal of Pharmacology—Molecular Pharmacology Section, 206: 297-300 (1991).
Donath, Edwin, et al. “The Influence of the Antiviral Drugs Amantadine and Rimantadine on Erythrocyte and Platelet Membranes and its Comparison with that of Tetracaine”, Biochemical Pharmacology 36:481-7 (1987).
Wang, J-J, Y-T Chern, Y-F Chang, T-Y Liu and C-W Chi, “Dimethyladamantylmaleimide-induced in vitro and in vivo growth inhibition of human colon cancer Colo205 cells”, Anti-Cancer Drugs 13: 533-43 (2002).
Wang, J-J, Y-T Chern, Y-F Chang, T-Y Liu and C-W Chi, “In vitro and in vivo growth inhibition of cancer cells by adamantylmaleimide derivatives”, Anti-Cancer Drug Design, 13: 779-796 (1998).
Wang, J-J, K-T Huang and Y-T Chern, “Induction Of Growth Inhibition And G1 Arrest in Human Cancer Cell Lines By Relatively Low-Toxic Diamantane Derivatives”, Anti-Cancer Drugs 15:277-286 (2004).
Wang, J-J, Y-F Chang, Y-T Chern, and C-W Chi, “Study of in vitro and in vivo effects of 1,6Bis[4-(4-amino-3-hydroxyphenoxyl)phenyl]diamantane (DPD), a novel cytostatic and differentiation inducing agent, on human colon cancer cells”, British Journal of Cancer, 89(10):1995-2003 (2003).
Attia, Mohammed A. M. and David W. Weiss, “Immunology of Spontaneous Mammary Carcinomas in Mice V. Acquired Tumor Resistance and Enhancement in Strain A Mice Infected with Mammary Tumor Virus”, Cancer Research 26, Part 1: 1787-1800 (1966).
Wang, J-J, Y-C Chen, C-W Chi, K-T Huang and Y-T Chern, “In vitro and In vivo Growth Inhibition and G1 Arrest in Human Cancer Cells By Diaminophenyladamantane Derivatives”, Anti-Cancer Drugs, 15: 697-705.

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