Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2005-06-21
2005-06-21
Wilson, James O. (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S638000, C564S248000, C564S509000
Reexamination Certificate
active
06908948
ABSTRACT:
A chemical composition and method of use of the composition is described. The chemical composition includes an aza-enediynes, aza-enyne allenes, or an aza-diallenes. These compound are preferably non-hydrolyzable, cationic compounds that bind to nucleic acids. In addition it is believed that these compounds may undergo chemical reactions in the presence of a nucleic acid to generate reactive intermediates that cleave nucleic acids.
REFERENCES:
patent: 5098920 (1992-03-01), Reitz
patent: 5767142 (1998-06-01), LaVoie et al.
patent: 6297284 (2001-10-01), Kérwin et al.
Vasilevskii et al. (Izv. Akad. Nauk, SSR, Ser. Khim, vol. 3: pp. 590-693, (1975).
Shvartsberg et al., Dokl. Vses. Konf. Khim. Atsetilena, 4th edition, (1972).
Kouvetakis et al. (Chem. Mater., vol. 6(5): pp. 636-639, (1994).
Buntan et al. (Macromolecules, vol. 29(8): pp. 2885-2893).
Vailevskii et al., “Acetylene derivatives of 1,2,4-triazole”, Izv. Akad. Nauk. SSSR, Ser. Khim., vol. (3): 690-693, 1975.
Shvartsberg et al., Dokl. Vses. Konf. Khim. Atselina, 4th ed., vol. 2, pp. 52-58, 1972.
Bizhan et al., “Synthesis and some properties of aminopropynylimidazoles”, Izv. Akad. Nauk. SSSR, Ser. Khim., vol. 11:2638-2640, 1973.
Shvartsberg et al., “Synthesis of 2-ethynyl and 4,5-diethynyl-1-methylimidazoles”, Izv. Akad. Nauk SSSR, Ser. Khim., vol. 23: 472-474, 1972.
Shvartsberg et al., “Acetylenic derivatives of heterocycles”, Izv. Akad. Nauk SSSR, Ser. Khim., vol. 7: 1534-1538, 1971.
Shvartsberg et al., “Synthesis and acetylenic condensation of iodo derivatives of N-methylimidazole”, Izv. Akad. Nauk SSSR, Ser. Khim., vol. 7: 1563-1569, 1979.
Medvedeva et al., “Structural effects of amines on the reaction course with 4,4-dimethyl-2-pentyn-1-al”, Izv. Akad. Nauk SSSR, Ser. Khim., vol. 6: 1347-1351, 1987.
Gal et al., Bull. Korean Chem. Soc., vol. 19(1): 22-23, 1998.
Ortaggi et al., “Oxidative Polymerisation of Aromatic Diethynyl Derivatives”, Gazzetta Chimica Italiana, vol. 119: 395-397, 1989.
Nakamura et al., Tetrahedron Letters, vol. 39: 301-304, 1998.
Faust et al., Tetrahedron Letters, vol. 38(46): 8017-8020, 1997.
Bunten et al., “Synthesis, Optical Absorption, Fluorescence, Quantum Efficiency, and Electrical Conductivity Studies of Pyridine/Pyridinium Dialkynyl Organic and Pt(II)-sigma-Acetylide Monomers and Polymers”, Macromolecules, vol. 29: 2885-2893, 1996.
Bunten et al., “Synthesis of Pyridine/Pyridinium-based Alkynyl Monomers; Oligomers and Polymers: Enhancing Conjugation by Pyridine N-Quaternization”, J. Mater. Chem., vol. 5(11): 2041-2043, 1995.
Inouye et al., “Molecular Recognition ofbeta-Ribofuranosides by Synthetic Polypyridine-Macrocyclic Receptors”, J. Amer. Chem. Soc., vol. 117(50): 12416-12425, 1995.
Lockhart, T.P.; Bergman, R.G., Evidence for the Reactive Spin State of 1,4-Dehydrobenzenes, J. Am. Chem. Soc., 1981, vol. 103, 4091-4096.
David, W.M.; Kerwin, S.M., Synthesis and Thermal Rearrangement of C,N-Dialkynyl Imines: A Potential Aza-Bergman Route to 2,5-Didehydropyridine, J. Am. Chem. Soc., 1997, vol. 119, 1464-1465.
Edo, K.; et al., The Structure of Neocarzinostatin Chromophore Possessing A Novel Bicyclo-[7,3,0] Dodecadiyne System, Tetrahedron Letters, 1985, vol. 26, 331-334.
Gillmann, T.; Heckhoff, S., Aza-Enyne Allenes: Thermal Reaction Behavior of 2,4,5-Hexatrienenitriles, Tetrahedron Letters, 1996, vol. 37, 839-840.
Shi, C.; Wang, K., Generation of Biradicals and Subsequent Formation of Quinolines and 5H-Benzo[b]carbazoles from N-[2-(1-Alkynyl)phenyl]ketenimines, J. Org. Chem., 1998, vol. 63, 3517-3520.
Gillmann, T.; et al., Synthesis and Thermal Reactivity of Enyne Allene Esters. An Intramolecular [2+2] Cycloaddition as a New Mode of Cycloisomerization, Synlett, 1995, 1257-1259.
Grissom, J.; Calkins, T., The Tandem Bergman-Radical Cyclization: A New Method For Ring Annulation, Tetrahedron Letters, 1992, vol. 33, 2315-2318.
Grissom, J.; et al., High Temperature Radical Cyclization Anomalies in the Tandem Enediyne-Bis-Radical Cyclization, Tetrahedron, 1994, vol. 50, 4635-4650.
Grissom, J.; et al., The Chemistry of Enediynes, Enyne Allenes and Related Compounds, Tetrahedron, 1996, vol. 52, 6453-6518.
Grissom, J.; et al., Tandem Enyne Allene-Radical Cyclization: Low-Temperature Approaches to Benz[e]indene and Indene Compounds, J. Org. Chem., 1997, vol. 62, 603-626.
Hangeland, J.; et al., Specific Abstraction of the 5′(S)- and 4′-Deoxyribosyl Hydrogen Atoms and DNA by Calicheamicinγ1I, J. Am. Chem. Soc., 1992, vol. 114, 9200-9202.
Jones, R.; Bergman, R., p-Benzyne. Generation as an Intermediate in a Thermal Isomerization Reaction and Trapping Evidence for the 1,4-Benzenediyl Structure, J. Am. Chem. Soc., 1972, vol. 94, 660-661.
Hoffner, J.; et al., Chemistry of the 2,5-Didehydropyridine Biradical: Computational, Kinetic, and Trapping Studies toward Drug Design, J. Am. Chem. Soc., 1998, vol. 120, 376-385.
Koga, N.; Morokuma, K., Comparison of Biradical Formation between Enediyne and Enyne-Allene. Ab Initio CASSCF and MRSDCI Study, J. Am. Chem. Soc., 1991, vol. 113, 1907-1911.
Lee, M.; et al., Calichemicins, a Novel Family of Antitumor Antibiotics. 2. Chemistry and Structure of Calichemicinγ1I, J. Am. Chem. Soc., 1987, vol. 109, 3466-3468.
Nakatani, K.; et al., Photoinduced DNA Cleavage by Designed Molecules with Conjugated Ene-Yne-Ketene Functionalities, Tetrahedron Letters, 1994, vol. 35, 605-608.
Nam, H.; et al., Didehydropyridines(Pyridynes): An ab Initio Study, J. Phys. Chem., 1991, vol. 95, 6514-6519.
Nicolaou, K.; et al., Designed Enediynes: A New Class of DNA-Cleaving Molecules with Potent and Selective Anticancer Activity, Science, 1992, vol. 256, 1172-1178.
Nicolaou, K.; et al., DNA Cleavage and Antitumor Activity of Designed Molecules with Conjugated Phosphine Oxide-Allene-Ene-Yne Functionalities, J. Am. Chem. Soc. 1990, vol. 112, 7825-7826.
Nicolaou, K.; Smith, A., Molecular Design, Chemical Synthesis, and Biological Action of Enediynes, Acc. Chem. Res., 1992, vol. 25, 497-503.
Moore, H.; Yerxa, B., Ring Expansions of Cyclobutenones-Synthetic Utility, Chemtracts-Organic Chemistry, 1992, vol. 5, 273-313.
Meyers, A.; et al., Thermal Generation of α,3-Dehydrotoluene from (Z)-1,2,4-Heptatrien-6-yne, J. Am. Chem. Soc. 1989, vol. 111, 8057-8059.
Nagata, R.; et al., DNA Cleavage by Acyclic Eneyne-Allene Systems Related to Neocarzinostatin and Esparamicin-Calicheamicin, Tetrahedron Letters, 1990, vol. 31, 2907-2910.
Padwa, A.; et al., A Comparative Study of the Decomposition of o-Alkynyl-Substituted Aryl Diazo Ketones. Synthesis of Polysubstituted β-Naphthols via Arylketene Intermediates, J. Org. Chem., 1993, vol. 58, 6429-6437.
Schmittel, M.; et al., Synthesis of Noval Enyne-Allenes, Their Thermal C2-C6Cyclization, and the Importance of a Benzofulvene Biradical in the DNA Strand Cleavage, Synlett, Feb. 1997, 165-166.
Schmittel, M.; et al., Switching from the Myers Reaction to a New Thermal Cyclization Mode in Enyne-Allenes, Tetrahedron Letters, 1995, vol. 36, 4975-4978.
Sullivan, R.; et al., DNA Cleavage by 4-Alkynyl-3-methoxy-4-hydroxycyclobutenones, J. Org. Chem., 1994, vol. 59, 2276-2278.
Toshima, K.; et al., Cycloaromatization and DNA Cleavage of Novel Enyne-allene Systems, J. Chem. Soc., Chem. Commun., 1993, 1406-1407.
Wang, K.; et al., Cascade Radical Cyclizations via Biradicals Generated from (Z)-1,2,4-Heptatrien-6-ynes, J. Am. Chem. Soc., 1996, vol. 118, 10783-10791.
Wang, K.; Wang, Z., Synthesis and Cycloaromatization of (Z)-1,2,4-Heptatrien-6-ynes and (Z)-2,4,5-Hexatrienenitriles, J. Org. Chem., 1996, vol. 61, 1516-1518.
Griller, D.; Ingold, K., Free-Radical Clocks, Acc. Chem. Res., 1980, vol. 13, 317-323.
Shi, C.; Wang, K., Generation of Biradicals and Subsequent Formation of Quinolines and 5H-Benzo[b]carbazoles from N-[2-(1-Alkynyl)phenyl]ketenimines, J. Org. Chem., 1998, vol. 63, 3517-3520.
International Search Report, Application No. PCT/US99/16171, mailed Oct. 28, 1999.
David Wendi M.
Kerwin Sean M.
Meyertons Eric B.
Meyertons Hood Kivlin Kowert & Goetzel P.C.
Owens Howard V.
Research Development Foundation
Wilson James O.
LandOfFree
DNA-cleaving antitumor agents does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with DNA-cleaving antitumor agents, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and DNA-cleaving antitumor agents will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3515076