Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2006-10-16
2008-08-12
Seaman, D. Margaret (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C514S301000, C514S302000
Reexamination Certificate
active
07411066
ABSTRACT:
Novel amino methylated 2-pyridinones, precursors, intermediates, and derivatives; the methods for the preparation of the same; uses of the same for inhibiting pili formation in bacteria; and pharmaceutical compositions comprising these compounds are described in this application. The present compounds may be employed to inhibit biofilm formation and thereby inhibit adherence of bacteria to a host cell.
REFERENCES:
patent: 5310562 (1994-05-01), Margolin
patent: 5624677 (1997-04-01), El-Rashidy et al.
patent: 6495539 (2002-12-01), Hultgren et al.
patent: 6841559 (2005-01-01), Almqvist et al.
patent: 84850 (1971-10-01), None
patent: 0133038 (1985-02-01), None
Svensson et al., Journal of Combinatorial Chemistry, 2000, 2(6), 736-748.
Pemberton et al. Journal of Organic Chemistry 2004, 69(23), 7830-7835.
Aggarwal, “Catalytic Asymmetric Synthesis of Epoxides from Aldehydes Using Sulfur Ylides with In Situ Generation of Diazocompounds,” 2001, Angew Chem Int Ed, 40/8, pp. 1430-1433.
Alterman, “Fast Microwave-Assisted Preparation of Aryl and Vinyl Nitriles and the Corresponding Tetrazoles from Organo-halides,” 2000, J Org Chem, 65, pp. 7984-7989.
Agnew, “Modern Variants of the Mannich Reaction,” 1998, Angew Chem Inc, 37, pp. 1044-1070.
Arvela, “Rapid Cyanation of Aryl Iodides in Water Using Microwave Promotion,” 2003, Org Biomol Chem, 1, pp. 1119-1121.
Arvela, “Rapid Easy Cyanation of Aryl Bromides and Chlorides Using Nickel Salts in Conjunction with Microwave Promotion,” 2003, J Org Chem, 68, pp. 9122-9125.
Asherson, “A General and Practicable Synthesis of Polycyclic Heteroaromatic Compounds. Part 1. Use of a Putative Quinolone-quinone-methide in the Synthesis of Polycyclic Heteroaromatic Compounds,” 1980, J Chem Soc Perkin Trans 1, pp. 512-521.
Asherson, “A General and Practicable Synthesis of Polycyclic Heteroaromatic Compounds. Part 2. Reaction of Quinone-methides of Pyrodones, Pyrimidines, Coumarin, and Benzene with Aromatic Amines in a Novel Synthesis of Polycyclic Heteroaromatic Compounds,” 1980, J Chem Soc Perkin Trans 1, pp. 522-528.
Bohme, 1976, Advanced Organic Chemistry, 9, p. 107.
Bohme, “Uber die Spaltung von Aminalen und a-Dialkylamino-athern mit Carbonsaurehalogeniden,” 1960, Chemische Berichte, 93, pp. 1305-1309. No English translation available.
Brana, “Reaction of N-(2-Pyridylmethyl)-3,5-dimethylbenzamide and N-(3-Pyridylmethyl)-3,5-dimethylbenzamide N-Oxides with Acetic Anhydride,” 1982, J Hetero Chem, pp. 1297-1300.
Brown, “Selective Reductions. 29. A Simple Technique to Achieve an Enhanced Rate of Reduction of Representative Organic Compounds by Boran-Dimethyl Sulfide,” 1982, J Org Chem, 47, pp.3153-3163.
Brown, “Molecular Addition Compounds. 11. N-Ethyl-N-Isopropylaniline-Borane, A Superior Reagent for Hydroborations and Reductions,” 1998, J Org Chem, 63, 5154-5163.
Brown, “Molecular Addition Compounds. 14. Convenient Preparations of Representative Dialkylborane Reagents Using the New, Highly Reactive N-Ethyl-N-Isopropylaniline-Borane Reagent (BACH-EI™),” 1999, Tetrahedron, 55, pp. 5991-6000.
Butler, “4.13 Tetrazoles,” 1984, Comprehensive Heterocyclic Chemistry, 5, pp. 791-838, Katritzky and Rees, Eds., Pergamon Press, Oxford.
Cha, “Reaction of Aluminum Hydride-Triethylamine Complex with Selected Organic Compounds Containing Representative Functional Groups,” 1993, J Org Chem, 58, pp. 3974-3979.
Clive, “Synthesis of Racemic Brevioxime and Related Model Compounds,” 2000, J Org Chem, 65, pp. 4923-4929.
Cox, “Synthesis of Isotopically Labelled 3-Amino-2-Phenylpropionic Acid and Its Role as a Precusor in the Biosynthesis of Tenellin and Tropic Acid,” 1991, J Chem Soc Perkin Trans 1, pp. 2537-2540.
Ellis, “Cyanation of Aromatic Halides,” 1987, Chem Rev, 87, pp. 779-794.
Emtenas, “An Enantioselective Ketene-Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones,” 2001, J Comb Chem, 66, pp. 6756-6761.
Emtenas, “Design and Parallel Solid-Phase Synthesis of Ring-Fused 2-Pyridinones that Target Pilus Biogenesis in Pathogenic Bactera,” 2002, J Comb Chem, 4, pp. 630-639.
Emtenas, “Efficient Mircowave Assisted Synthesis of Optically Active Bicyclic 2-Pyridinones via Δ2-thiazolines,” 2003, Molecular Diversity, 7, pp. 165-169.
Hanessian, “Design and Synthesis of Conformationally Constrained Amino Acids as Versatile Scaffolds and Peptide Mimetics,” 1997, Tetrahedron, 53(38), pp. 12789-12854.
Hasvold, “Pyridone-Containing Farnesyltransferase Inhibitors: Synthesis and Biological Evaluation,” 2003, Bioorganic Med Chem Letters, 13, pp. 4001-4005.
Heaney, “The Generation of Iminium Ions Using Chlorosilanes and their Reactons with Electron Rich Aromatic Heterocycles,” 1997, Tetrahedron 53(8), pp. 2941-2958
Jin, “Palladium-Catalyzed Cyanation Reactions of Aryl Chlorides,” 2000, Tetrahedron Letters, pp. 3271-3273.
Khanapure, “Intramolecular Sulfur-Assisted NaBH4 Reduction of Esters Synthesis of 5-oxo-ETE and 5-oxo-12-HETE,” 2000, Tetrahedron Letterers, 41, 5653-5657
Lange, “A New Mild Method for the Synthesis of Amidines,” 1999, Tetrahedron Letters 40, pp. 7067-7070.
Leadbeater, “Ionic Liquids as Reagents and Solvents in Conjunction with Microwave Heating: Rapid Synthesis of Alkyl Halides from Alcohols and Nitriles from Aryl Halides,” 2003, Tetrahedron, 59, pp. 2253-2258.
Lee, “Targeting Virulence for Antimicrobial Chemotherapy,” 2003, Curr Opin in Pharm, 3, pp. 513-519.
Letinois, “Heterogeneous Rhodium-Catalyzed Hydrogenation Conditions for the Highly Effective Synthesis of 1,3-Oxazolidines from 1,2-Amino Alcohols and Nitriles,” 1998, Tetrahedron Letters, 39, pp. 2327-2330.
Li, “The 2-Pyridone Antibacterial Agents: Bacterial Topoisomerase Inhibitors,” 2000, Med Res Rev, 20, pp. 231-293.
Mannich, “Ueber ein Kondensationprodukt aus Formaldehyd, Ammoniak und Antipyrin,” 1912, W. Arch. Pharm, pp. 647-667 German Text Only Available.
Marlett, “Dimethylethylamine-Alane and N-Methylpyrrolidine-Alane. A Convenient Synthesis of Alane, A Useful Selective Reducing Agent in Organic Synthesis,” 1990, J Org Chem, 55, pp. 2968-2969.
Mojtahedi, “Microwave-Assisted Aminomethylation of Electron-Rich Compounds Under Solvent-Free Condition,” 2000, Synthetic Comm, 30(1), pp. 69-72.
Mulvey, “Adhesion and Entry of UropathogenicEscherichia coli,” 2002, Cell Microbiol, 4(5), pp. 257-271.
Nagarajan, “Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Topoisomerase I Inhibitors Featuring Polyamine Side Chains on the Lactam Nitrogen,” 2003, J Med Chem, 46, pp. 5712-5724.
Padwa, “An Isomunchnone-Based Method for the Synthesis of Highly Substituted 2(1H)-Pyridones,” 1999, J Org Chem, 64, pp. 8648-8659.
Patel, “Synthesis of Some 6-Substituted Aminopyridin-2(H)-ones & Their Derivatives,” 1987 Indian J of Chem, 26B, pp. 1099-1101.
Patrick, “Class I Broad-Spectruc Antibiotics—Ampicillin and Amoxycillin (Beechams 1964),” , 2001, An Introduction to Medicinal Chemistry, 2nd Ed, pp. 400-402, Oxford University Press.
Rounds, “Hydrolysis in the Absence of Bulk Water 2. Chemoselective Hydrolysis of Nitriles Using Tetrahalophthalic Acids,” 1988, Tetrahedron Letters, 29(50), pp. 6557-6560.
Sharifi, “Solvent-Free Aminoaklylation of Phenols and Indoles Assisted by Microwave Irradiation,” 2001, Monatshefte fur Chemie, 132, pp. 875-880.
Sundermeier, “Palladium-Catalyzed Cyanation of Aryl Halides: Recent Developments sand perspectives,” 2003, Eur J Inorg Chem, pp. 3513-3526.
Svensson, “Design and Evaluation of Pilicides: Potential Novel Antibacterial Agents Directed Against UropathogenicEscherichia
Aberg Veronica
Almqvist Fredrik
Hultgren Scott J.
Larsson Andreas
Pemberton Nils
Chandrakumar Nizal S
Seaman D. Margaret
Senniger Powers LLP
Washington University
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