Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2007-05-16
2010-06-15
Desai, Rita J (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
Reexamination Certificate
active
07737164
ABSTRACT:
The present invention relates generally to compounds providing antibacterial therapeutic agents and preparations, and related methods of using and making antibacterial compounds. Antibacterial compounds of the present invention include chalcone, alkylpyrimidine, aminopyrimidine and cyanopyridine compounds and derivatives thereof exhibiting minimum inhibitory concentrations (MIC) similar to or less than conventional antibacterial compounds in wide use. For example, the present invention provides chalcone and cyanopyridine compounds, and derivatives thereof, exhibiting high antibacterial activities having multiple electron withdrawing group substituents, such as halogens and fluorinated alky groups, and optionally having hydroxyl and/or alkoxyl groups substituents.
REFERENCES:
patent: 2007/0128658 (2007-06-01), Blackwell et al.
patent: 4-279568 (1992-10-01), None
patent: WO 98/15532 (1998-04-01), None
patent: WO2006/084056 (2006-08-01), None
Elagamey et al Collection of Czechoslovak Chemical Communications 1990, 55, 524-534.
Yamaguchi et al J. Het. Chem. 1998, 35, 805-810.
Andrews, J.M. (2001) “Determination of Miniumum Inhibitory Concentrations,”J. Antimicrob. Chemother. 48(Supp. 1):5-16.
Barnick et al. (1979) “A Convenient Direct Method for the Preparation of β-Keto-Acids,”Synthesis79:787-788.
Bassler et al. (2006) “Bacterially Speaking,”Cell125:237-246.
Bassler et al. (1995) “Intracellular Communication in MarineVibrioSpecies: Density-Dependent Regulation of the Expression of Bioluminescence,” In;Two Component Signal Transduction, Hoch et al. Eds., Am. Soc. Microbiol., Washington D.C., pp. 431-435.
Bassler et al. (1993) “Intercellular Signalling inVibrio harveyi: Sequence and Function of Genes Regulating Expression of Luminescence,”Mol. Microbiol. 9(4):773-786.
Bassler et al. (1994) “Multiple Signaling Systems Controlling Expression of Luminescence inVibrio Harvey: Sequenceand Function of Genes Encoding a Second Sensory Pathway,”Mol. Micobiol. 13(2):273-286.
Bauer et al. (1966)Tech Bull. Reg. Med. Technologists36:49-52.
Behrendt et al. (1999) “Phootomodulation of the Conformation of Cyclic Peptides with Azobenzene Moieties in the Peptide Backbone,”Angew. Chem. Int. Ed. Engl. 38:2771-2774.
Blackwell, H.E. (2006) “Hitting the SPOT: Small Molecule Macroarrays Advance Combinatorial Synthesis,”Curr. Opin. Chem. Biol. 10:203-212.
Blackwell et al. (2003) “Out of the Oil Bath and into the Oven—Microwave-Assisted Combinatorial Chemistry Heats Up,”Org. Biomol. Chem. 1:1251-1555.
Bowman et al. (2006) “Efficient Synthesis of Small Molecule Macroarrays: Optimization of the Macroarray Synthesis Platform and Examination of Microwave and Conventional Heating Methods,”Tetrahedron62:4715-4727.
Bowman et al. (2006) “Discovery of Fluorescent Cyanopyridine and Deazalumazine Dyes Using Small Molecule Macroarrays,”Org. Lett. 8:1645-1648.
Bowman et al. (2004) “Microwave-Accelerated SPOT-Synthesis on Cellulose Supports,”Org. Lett. 6(12):2019-2022.
Carpino et al. (1972) “The 9-Fluorenylmethoxycarbonyl Amino-Protecting Group,”J. Org. Chem. 37 (22):3404-3409.
Eberhard et al. (1986) “Analogs of the Autoinducer of Bioluminescence in Vibrio fischeri,”Arch. Microbiol. 146:35-40.
Eberhard et al. (2000) “Chemical Synthesis of Bacterial Autoinducers and Analogs,”Methods Enzymol. 305:301-315.
Fleming et al. (Nov. 13, 1995) “Chemical Reagents in Photoaffinity Labeling,”Tetrahedron51(46):12479-12520.
Fray et al. (1999) “Plants Genetically Modified to ProdiceN-acylhomoserine Lactones Communicate with Bacteria,”Nat. Biotechnol. 17:1017-1020.
Frezza et al. (2006) “Synthesis and Biological Evaluatioon of Homoserine Lactone Derived Ureas as Antafonists of Bacterial Quorum Sensing,”Bioorg. Med. Chem. 14:4781-4791.
Fuqua et al. (2002) “Listening in on Bacteria: Acyl-Homoserine Lactone Signaling,”Nat. Rev. Mol. Cell Biol. 3:685-695.
Fuqua et al. (2001) “Regulation of Gene Expression by Cell-to-Cell Communication: Acyl-Homoserine Lactone Quorum Sensing,”Ann. Rev. Genet. 35:439-468.
Kappe, C.O. (2004) “Controlled Microwave Heating in Modern Organic Synthesis,”Angew Chem. Int. Ed. 43:6250-6284.
Kappel et al. (2005) “A Convenient Orthogonally Cleavable Methionine Handle for Anchoring Amines to Polymeric Supports,”J. Comb. Chem. 7:78-84.
Koch et al. (2005) “The LuxR Receptor: The Sites of Interaction with Quorum-Sensing Signals and Inhibitors,”Microbiology151:3589-3602.
Lee et al. (2006) “Activity of Purified QscR, aPseudomonas aeruginosaOrphan Quorum-Sensing Transcription Factor,”Mol. Microbiol. 59:602-609.
Ley et al. (Aug. 2002) “New Tools and Concepts for Modern Organic Synthesis,”Nat. Rev. Drug. Discov. 1(8):573-586.
Lin et al. (2006) “Rapid Synthesis of Diketopiperazine Macroarrays via Ugi Four-Component Reactions on Planar Solid Supports,”Chem. Commun. :2884-2886.
Lin et al. (20055) “Small Molecule Macroarray Construction via Ugi Four-Component Reactions,”Org. Lett. 7:4455-4458.
Matsui et al. (1992)J. Chem. Soc. Perk. Trans. 2:201-206.
Ni et al. (2004) “Recent Advances in Therapeutic Chalcones,”Exp. Opin. Ther. Patents14:1669-1691.
Nielsen et al. (2005) “Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action,”J. Med. Chem. 48:2667-2677.
Nielson et al. (2004) “Antibacterial Chalcones—Bioisosteric Replacement of the 4′ -hydroxy Group,”Bioorg. Med. Chem. 12:3047-3054.
Nogrady (1985) “Pro-Drugs and Soft Drugs,” In;Medicinal Chemistry A Biochemical Approach, Oxford Press, New York, pp. 388-392.
Powers et al. (1998) “Automated Parallel Synthesis of Chalcone-Based Screening Libraries,”Tetrahedron54:4085-4096.
Rajvaidya et al. (2004) “Synthesis and Microbiological Activities of Some Pyrazoles and Cyanopyridines,”Indian J. Chem. 43B:906-908.
Rathke et al (Oct. 1985) “Synthesis of β-Keto Acids and Methyls Ketones UsingBis(trimethylsily) Malonate and Triethylamine in the Presence of Lithium or Magnesium Halides,”Synth. Commun. 15(12):1039-1049.
Schultz et al. (2003) “Mechanism and Dynamics of Azobenzene Photoisomerization,”J. Am. Chem. Soc. 125(27):8098-8099.
Tsiodras et al. (Jul. 2001) “Linezolid Resistance in a Clinical Isolate ofStaphylococcus aureus,” Lancet358:207-208.
Bowden et al. (1990) “Structure-Activity Relations. Part 5. Antibacterial Activity of a Series of Substituted (E)-3-(4-Phenylbenzoyl)acrylic Acids, -Chalcones, -2-Hydroxychalcones and -α-Bromochalcones; Addition of Cyteine to Substitutes 3-Benzoylacrylic Acids and Related Compounds,”J. Chem. Res. (S) 377.
Bowden et al. (1990) “Structure-Activity Relations. Part 5. Antibacterial Activity of a Series of Substituted (E)-3-(4-Phenylbenzoyl)acrylic Acids, -Chalcones, -2-Hydroxychalcones and α-Bromochalcones; Addition of Cyteine to Substitutes 3-Benzoylacrylic Acids and Related Compounds,”J. Chem. Res. (M) 2801-2830.
Bowden et al. (1979) “Structure-Activity Relations. Part 4. Reactivity and Anti-Bacterial Activity of 3-Aroylacrylic Acids and Their Methyl Esters,”J. Chem. Res. (S) 8.
Krohnke, F. (1976) “The Specific Synthesis of Pyridines and Oligopyridines,”Synthesis:1-24.
Dobaria, A. V. et al. (2002) “Synthesis and antimicrobial screening of cyanopyridines,” J. Indian Chem. Soc. 79:772-773.
International Search Report and Written Opinion PCT/US2007/069069.
International Preliminary Report on Patentability PCT/US2007/069069.
Marzinzik et al. (1998) “Key Intermediates in Combinatorial Chemistry: Access to Various Heterocycles from α,β-Unsaturated Ketones on the Solid Phase,”J. Org. Chem. 63:723-727.
Misra et al. (19
Blackwell Helen E.
Bowman Matthew D.
O'Neill Jennifer C.
Stringer Joseph R.
Desai Rita J
Greenlee Winner and Sullivan P.C.
Mabry John
Wisconsin Alumni Research Foundation
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