Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2006-01-03
2006-01-03
Davis, Brian (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S153000, C564S445000, C564S454000, C564S455000, C564S457000, C564S461000
Reexamination Certificate
active
06982351
ABSTRACT:
Conformationally restricted polyamine compounds useful in treatment of cancer and other diseases marked by abnormal cell proliferation are disclosed. Improved methods of synthesizing such compounds are also disclosed. In one method of the invention, a carbene-bearing or carbene equivalent-bearing compound is reacted with the double bond of an alkene compound to form a cyclopropyl ring as the first step in the synthesis.
REFERENCES:
patent: 3008993 (1961-11-01), Lesslie et al.
patent: 3397223 (1968-08-01), Payne
patent: 3773833 (1973-11-01), Henrici et al.
patent: 4035174 (1977-07-01), Grier et al.
patent: 4092432 (1978-05-01), Björklund et al.
patent: 4153567 (1979-05-01), Kluger et al.
patent: 4491651 (1985-01-01), Naiman
patent: 4537601 (1985-08-01), Naiman
patent: 4590288 (1986-05-01), Klemann
patent: 4642344 (1987-02-01), Hajek et al.
patent: 4698446 (1987-10-01), Lai et al.
patent: 4935449 (1990-06-01), Bey et al.
patent: 5021409 (1991-06-01), Murrer et al.
patent: 5021571 (1991-06-01), Mease et al.
patent: 5217964 (1993-06-01), Edwards et al.
patent: 5354782 (1994-10-01), Edwards et al.
patent: 5374658 (1994-12-01), Lau
patent: 5401443 (1995-03-01), Nagano et al.
patent: 5413719 (1995-05-01), Sivakumar et al.
patent: 5434145 (1995-07-01), Edwards et al.
patent: 5498522 (1996-03-01), Porter
patent: 5516807 (1996-05-01), Hupe et al.
patent: 5541230 (1996-07-01), Basu et al.
patent: H1633 (1997-02-01), Hiebert et al.
patent: 5606053 (1997-02-01), Prashad et al.
patent: 5607574 (1997-03-01), Hart
patent: 5608061 (1997-03-01), Ciszewski et al.
patent: 5608086 (1997-03-01), Hemmerle
patent: 5612478 (1997-03-01), Xu et al.
patent: 5646188 (1997-07-01), Gilad et al.
patent: 5654287 (1997-08-01), Prakash et al.
patent: 5672202 (1997-09-01), Stirling et al.
patent: 5677349 (1997-10-01), Gilad et al.
patent: 5677350 (1997-10-01), Frydman
patent: 5681837 (1997-10-01), Bergeron
patent: 5707532 (1998-01-01), Guerro et al.
patent: 5744453 (1998-04-01), Mintz et al.
patent: 5763388 (1998-06-01), Lightsey et al.
patent: 5843959 (1998-12-01), Bergeron, Jr.
patent: 5880161 (1999-03-01), Basu et al.
patent: 5889061 (1999-03-01), Frydman et al.
patent: 5962533 (1999-10-01), Bergeron, Jr.
patent: 6100430 (2000-08-01), Yamamoto et al.
patent: 6392098 (2002-05-01), Frydman et al.
patent: 2003/0130356 (2003-07-01), Frydman et al.
patent: 1295826 (1969-05-01), None
patent: 05-032902 (1993-02-01), None
patent: 07-277964 (1995-10-01), None
patent: WO 95/18091 (1995-07-01), None
patent: WO 96/22962 (1996-08-01), None
patent: WO 96/40096 (1996-12-01), None
patent: WO 97/02027 (1997-01-01), None
patent: WO 97/31611 (1997-09-01), None
patent: WO 98/17624 (1998-04-01), None
patent: WO 98/32729 (1998-07-01), None
patent: WO 99/21542 (1999-05-01), None
patent: WO 99/54283 (1999-10-01), None
patent: WO 00/66175 (2000-11-01), None
patent: WO 00/66528 (2000-11-01), None
patent: WO 00/66587 (2000-11-01), None
patent: WO 03/033455 (2003-04-01), None
patent: WO 03/050072 (2003-06-01), None
Barluenga et al., Diastereoselective Intermolecular Cyclopropanation of Simple Alkenes by Fischer Alkenyl and Heteroaryl Carbene Complexes of Chromium: Scope and Limitations. J. Am. Chem. Soc., 2000, 122, p. 8145-54.
Alfonso, I. et al. (1996). “Sequential Biocatalytic Resolution of (+)-trans-cyclohexane-1,2-diamine. Chemoenzymatic Synthesis of an Optically Active Polyamine,”Chem. Commun.21:2471-2472.
Ashton, W.T., et al. (1988). “Synthesis and Antiherpetic Activity of (±)-9-[[(Z)-2-(Hydroxymethyl)cyclopropyl]methyl]guanine and Related Compounds,”J. Med. Chem.31(12):2304-2315.
Bachmann, S. et al. (2001). “Cis-Selective Asymmetric Cyclopropanation of Olefins Catalyzed by Five-Coordinate [RuC1(PNNP)]+ Complexes,”Organometallics20(10):2102-2108.
Bachrach, U. et al. (1971). “Antivirus Action of Acrolein, Glutaraldehyde and Oxidized Spermine,”J. Gen. Virol.13:415-422.
Bachrach, U. et al. (1971). “Inactivation of Myxoviruses by Oxidized Polyamines,”J. Gen. Virol.11:1-9.
Bachrach, U. et al. (1972). “Effect of Oxidized Spermine and Other Aldehydes on the Infectivity of Vaccinia Virus,”Appl. Microbiol.23(2):232-235.
Basu, H.S. et al. (1990). “Effects of Variation in the Structure of Spermine on the Association with DNA and the Induction of DNA Conformational Changes,”Biochem. J.269(2):329-334.
Behe, M. et al. (1981). “Effects of Methylation on a Synthetic Polynucleotide: the B—Z Transition in Poly(dG-m5dC)-Poly(dG-m5dC),”Proc. Natl. Acad. Sci. USA78(3):1619-1623.
Berchtold, C.M. et al. (1998). “Inhibition of Cell Growth in CaCO2 Cells by the Polyamine Analogue N1,N12-Bis(Ethyl)Spermine is Preceded by a Reduction in MYC Oncoprotein Levels,”Journal of Cellular Physiology174(3):380-386.
Bergeron, R.J. et al. (1994). “Antiproliferative Properties of Polyamine Analogues: A Structure-Activity Study,”J. Med. Chem.37:3464-3476.
Bernacki, R.J. et al. (1992). “Antitumor Activity of N,N′-Bis(Ethyl)Spermine Homologues Against Human MALME-3 Melanoma Xenografts,”Cancer Research52:2424-2430.
Bloomfield, V.A. et al. (1981). “Interactions of Polyamines with Polynucleotides” Chapter 10In Polyamines in Biology and Medicine, Morris, D.L. et al., eds., Marcell Dekker, Inc.: New York, 8:184-206.
Byers, T.L. et al. (1990). “Regulation of Polyamine Transport in Chinese Hamster Ovary Cells,”Journal of Cellular Physiology143:460-467.
Casero, R.A. et al. (1995). “Growth and Biochemical Effects of Unsymmetrically Substituted Polyamine Analogues in Human Lung Tumor Cells,”Cancer Chermother. Pharmacol.36:69-74.
Casero, R.A. et al. (2001). “Terminally Alkylated Polyamine Analogues as Chemotherapeutic Agents,”Journal of Medicinal Chemistry44(1):1-26.
Chang, B.K. et al. (1992). “Antitumor Effects of N-Alkylated Polyamine Analogues in Human Pancreatic Adenocarcinoma Models,”Cancer Chemother. Pharmacol.30:179-182.
Chang, B.K. et al. (1992). “Regulatory and Antiproliferative Effects ofN-Alkylated Polyamine Analogues in Human and Hamster Pancreatic Adenocarcinoma Cell Lines,”Cancer Chemother. Pharmacol.30:183-188.
Chang, B.K. et al. (1993). “Effects of Diethyl Spermine Analogues in Human Bladder Cancer Cell Lines in Culture,”Journal of Urology150:1293-1297.
Davidson, N.E. et al. (1993). “Growth Inhibition of Hormone-Responsive and -Resistant Human Breast Cancer Cells in Culture by N1, N12-Bis(Ethyl)Spermine,”Cancer Research53:2071-2075.
Doyle, M.P. et al. (1993). “Tetrakis[(4S)-4-phenyloxazolidin-2-one]dirhodium(II) and Its Catalytic Applications for Metal Carbene Transformations,”Helv. Chim. Acta.76:2227-2235.
Fernandez, C.O. et al. (1994). “Interactions Between Polyamine Analogs with Antiproliferative Effects and tRNA: a15N NMR Analysis,”Cell Mol. Biol.40(7): 933-944.
Feuerstein, B.G. et al. (1991). “Implications and Concepts of Polyamine-Nucleic Acid Interactions,”Journal of Cellular Biochemistry46:37-47.
Fischer, H.A. (1975). “Synthesis of3H-spermine,”J. Labelled Compd.11(1):141-143.
Frydman, B. et al. (1999). “Polyamine-based Chemotherapy of Cancer,”Opin. Ther. Patents. 9(8):1055-1068.
Frydman, L. et al. (1992). “Interactions Between Natural Polyamines and tRNA: an15N NMR Analysis,”Proc. Natl. Acad. Sci. USA89:9186-9190.
Gosule, L.C. et al. (1978). “DNA Condensation with Polyamines I. Spectroscopic Studies,”J. Mol. Biol.121:311-326.
Goto, M. et al. (1969). “Stereochemical Studies of Metal Chelates. III. Preparation and Stereochemistry of Cobalt (III) Complexes with C-Substituted Triethylenetetramines at the Central Ethylenediamine Bridge,”Inorg. Chem.8(2):358-366.
Ha, H.C. et al. (1998). “Unsymmetrically Substituted Polyamine Analogue Induces Caspase-Independent Programmed Cell Death in Bcl-2-Overexpressing Cells,”Cancer Research58:2711-2714.
Hafner, E.W. et
Basu Hirak S.
Blokhin Andrei V.
Frydman Benjamin
Marton Laurence J.
Reddy Venodhar K.
CellGate, Inc.
Davis Brian
Morrison & Foerster / LLP
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