Amino methylated 2-pyridinones

Details Amino methylated 2-pyridinones Amino methylated 2-pyridinones

2011-03-29

2011-03-29

Chandrakumar, Nizal S (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

07915417

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: 7411066 (2008-08-01), Hultgren et al.
patent: 84850 (1971-10-01), None
patent: 0133038 (1985-02-01), None
Stevensson et al. Journal of Combinatorial Chemistry, 2000, 2(6), 736-748.
Dorwald F. A. Side Reactions in Organic Synthesis, 2005, Wiley: VCH, Weinheim p. IX of Preface p. 1-15.
Pemberton et al. Journal of Organic Chemistry (2004), 69, 7830-7835.
Emtenas et al. Journal of Organic Chemistry , 2001, 66, 6756-6761.
Aggarwal, “Catalytic Asymmetric Synthesis of Epoxides from Aldehydes Using Sulfur Ylides with in Situ Generation of Diazocompounds,” 2001, Angew Chem Int Ed, 40(8):1430-1433.
Agnew, “Modern Variants of the Mannich Reaction,” 1998, Angew Chem Inc, 37:1044-1070.
Almqvist et al., “Alternative Way of Synthesizing Thiazoline Derivatives,” 1998, Tetrahedron Letters, 29:2293-2294.
Alterman, “Fast Microwave-Assisted Preparation of Aryl and Vinyl Nitriles and the CorrespondingTetrazoles from Organo-halides,” 2000, J Org Chem, 65:7984-7989.
Arvela, “Rapid Cyanation of Aryl Iodides in Water Using Microwave Promotion,” 2003, Org Biomol Chem, 1:1119-1121.
Arvela, “Rapid Easy Cyanation of Aryl Bromides and Chlorides Using Nickel Salts in Conjunction with Microwave Promotion,” 2003, J Org Chem, 68:9122-9125.
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 Perkins 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 Perkins I, pp. 522-528.
Barker et al. “3:6-Disubstituted Fluorenes. Part II. The Preparation of 3:6-diaminofluorene from Fluorene, and the Attempted Internuclear Cyclisation of Derivatives of 4:4-′diaminodiphenylmethane,” 1954, J Chem Soc, pp. 870-873.
Bohme, 1976, “Methyleniminium Salts,” Advanced Organic Chemistry, 9:107-223.
Bohme, “Uber die Spaltung von Aminalen and a-Dialkylamino-athern mit Carbonsaurehalogeniden,” 1960, Chemische Berichte, (93):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, 19:1297-1300.
Brown, “Selective Reductions. 29. A Simple Technique to Achieve an Enhanced Rate of Reduction of Representative Organic Compounds by Borane-Dimethyl Sulfide,” 1982, J Org Chem, 47:3153-3163.
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, 55:5991-6000.
Butler, “4.13 Tetrazoles,” 1984, Comprehensive Heterocyclic Chemistry, 5:791-838, Katritzky and Rees, Eds., Pergamon Press, Oxford, England.
Capps et al. “Synthesis of Bicyclic Pyridone and Dihydropyridone Analogues of B-Lactam Antiobiotics,” 1991, J Chem Soc Perkins I, pp. 3077-3086.
Casinovi et al. “A New Antibiotic Produced by Strain ofAspergillus flavipes,” 1968, Tetrahedron Letters, 27:3175-3178.
Cha, “Reaction of Aluminum Hydride-Triethylamine Complex with Selected Organic Compounds Containing Representative Functional Groups,” 1993, J Org Chem, 58:3974-3979.
Clive, “Synthesis of Racemic Brevioxime and Related Model Compounds,” 2000, J Org Chem, 65:4923-4929.
Cox, “Synthesis of Isotopically Labelled 3-Amino-2-Phenylpropionic Acid and Its Role as a Precursor in the Biosynthesis of Tenellin and Tropic Acid, ” 1991, J Chem Soc Perkins I, pp. 2537-2540.
Ellis, “Cyanation of Aromatic Halides,” 1987, Chem Rev, 87:779-794.
Emtenas, “An Enantioselective Ketene-Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones,” 2001, J Comb Chem, 66:6756-6761.
Emtenas, “Design and Parallel Solid-Phase Synthesis of Ring-Fused 2-Pyridinones that Target Pilus Biogenesis in Pathogenic Bacteria,” 2002, J Comb Chem, 4:630-639.
Emtenas, “Efficient Microwave Assisted Synthesis of Optically Active Bicyclic 2-Pyridinones via Δ-thiazolines,” 2003, Molecular Diversity, 7:165-169.
Fang et al. “Total synthesis of the angiotensin-converting enzyme inhibitor A58365A: On the Use of Pyroglutamate as a Chiral Educt,” 1989, Tetrahedron Letters, 30(28):3621-3624.
Groutas et al. “Substituted 2-Pyrones, 2-Pyridones, and Other Congeners of Elasnin as Potential Agents for the Treatment of Chronic Obstructive Lung Diseases” J. Med. Chem., 28:1106 (1985).
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, 13:4001-4005.
Head et al. “Validate: A New Method for the Receptor Based Prediction of Binding Affinities of Novel Ligands,” 1996, J. American Chemical Society, 118:3959-3969.
Heaney, “The Generation of Iminium Ions Using Chlorosilanes and their Reactions with Electron Rich Aromatic Heterocycles,” 1997, Tetrahedron Letters, 53(8):2941-2958.
Jin, “Palladium-Catalyzed Cyanation Reactions of Aryl Chlorides,” 2000, Tetrahedron Letters, 41:3271-3273.
Karlsson et al. “Binding Peptides in Solution by theEscherichia coliChaperone PapD as Revealed Using an Inhibition ELISA and NMR Spectroscopy,” 1998, Bioorgan & Med Chem, 6:2085-2101.
Khanapure, “Intramolecular Sulfur-Assisted NaBH4 Reduction of Esters Synthesis of 5-oxo-ETE and 5-oxo-12-HETE,” 2000, Tetrahedron Letters, 41:5653-5657.
Kuehn et al. “Structural Basis of Pilus Subunit Recognition by the PapD Chaperone,” 1993, Science, 262:1234-1241.
Lange, “A New Mild Method for the Synthesis of Amidines,” 1999, Tetrahedron Letters, 40:7067-7070.
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, 59:2253-2258.
Lee, “Targeting Virulence for Antimicrobial Chemotherapy,” 2003, Curr Opin in Pharm, 3:513-519.
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, 39:2327-2330.
Li, “The 2-Pyridone Antibacterial Agents: Bacterial Topoisomerase Inhibitors,” 2000, Med Res Rev, 20:231-293.
Linn et al. “Solid Phase Synthesis of 1,3,5-Trisubstituted Pyridin-2-ones,” 1999, Tetrahedron Letters, 40:2227-2230.
Mannich, “Ueber ein Kondensationprodukt aus Formaldehyd, Ammoniak and Antipyrin,” 1912, W. Arch. Pharm, pp. 647-667

Affiliated with

Also associated with

Rating

Amino methylated 2-pyridinones does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Amino methylated 2-pyridinones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Amino methylated 2-pyridinones will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2619954