Patent
Antibacterial agents
| العنوان: | Antibacterial agents |
|---|---|
| Patent Number: | 8,084,615 |
| تاريخ النشر: | December 27, 2011 |
| Appl. No: | 11/928122 |
| Application Filed: | October 30, 2007 |
| مستخلص: | Antibacterial compounds of formula I are provided: [chemical expression included] As well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of the compounds. |
| Inventors: | Andersen, Niels H. (Seattle, WA, US); Bowman, Jason (Quincy, IL, US); Erwin, Alice L. (Somerville, MA, US); Harwood, Eric A. (Seattle, WA, US); Kline, Toni (Seattle, WA, US); Mdluli, Khisimuzi E. (New York, NY, US); Ng, Simon (Walnut Creek, CA, US); Pfister, Keith B. (San Ramon, CA, US); Shawar, Ribhi (Phoenixville, PA, US); Wagman, Allan S. (Belmont, CA, US); Yabannavar, Asha (Lafayette, CA, US) |
| Assignees: | University of Washington (Seattle, WA, US), Novartis Vaccines and Diagnostics, Inc. (Emeryville, CA, US) |
| Claim: | 1. A compound according to the formula VII: [chemical expression included] or a pharmaceutically acceptable salt or ester thereof, wherein D is substituted or unsubstituted heteroaryl; G is absent or selected from the group consisting of —C≡C—, and —C≡C—C≡C—; and A is an amino acid side chain. |
| Claim: | 2. A pharmaceutical composition comprising: the compound of claim 1 , or a pharmaceutically acceptable salt or ester thereof; and a pharmaceutically acceptable excipient. |
| Claim: | 3. A method of treating infection in a subject comprising: administering an effective amount of the compound of claim 1 , or a pharmaceutically acceptable salt or ester thereof, to the subject. |
| Current U.S. Class: | 546/309 |
| Patent References Cited: | 2772281 November 1956 Holly et al. 5925659 July 1999 Patchett et al. 6218389 April 2001 Almstead et al. 6228988 May 2001 Floyd et al. 6281245 August 2001 Patel et al. 6358987 March 2002 Beckett et al. 7358359 April 2008 Andersen et al. 2001/0053555 December 2001 Patel et al. 2004/0229955 November 2004 Andersen et al. 2006/0154988 July 2006 Andersen et al. 2007/0244197 October 2007 Andersen et al. 2008/0269221 October 2008 Andersen et al. 2009/0163496 June 2009 Andersen et al. 2009/0247506 October 2009 Andersen et al. 2011/0172174 July 2011 Andersen et al. WO-9626223 August 1996 97/05105 February 1997 WO-97/05105 February 1997 97/42179 November 1997 WO-9742179 November 1997 98/15525 April 1998 WO-98/15525 April 1998 WO-9818754 May 1998 WO-9822494 May 1998 99/06340 February 1999 WO-99/06340 February 1999 WO-9939704 August 1999 WO-9957097 November 1999 WO 00/02904 January 2000 WO 00/44373 August 2000 WO 00/59874 October 2000 WO-0061134 October 2000 WO 02/30873 April 2002 WO-0250081 June 2002 WO-03/004488 January 2003 WO-2004007444 January 2004 WO 2004/062601 July 2004 |
| Other References: | Burger's Medicinal Chemistry and Drug Discovery 5th vol. I, (1995), Manfred E. Wolff ed., John Wiley & Sons, NY, p. 975-977. cited by examiner Modern Pharmaceutics 3rd ed., (1996), Gilbert S. Banker et al, ed., Marcel Dekker, Inc., NY, p. 596. cited by examiner U.S. Appl. No. 11/837,327, filed Aug. 10, 3007, Unknown. cited by other U.S. Appl. No. 11/981,279, filed Oct. 31, 2007, Unknown. cited by other U.S. Appl. No. 11/289,658. cited by other U.S. Appl. No. 11/894,208, Andersen et al. cited by other Jackman et al., Antibacterial Agents that Target Lipid a Biosynthesis in Gram-Negative Bacteria, J. Biological Chemistry 275(15):11002-11009 (2000). cited by other Khan et al., “A Facile and Convenient Solid-Phase Procedure for Synthesizing Nucleotide Hydroxamic Acids,” Tetrahedron Letters 39:8031-8034 (1998). cited by other Kline et al., “Potent Novel In Vitro Inhibitors of the Pseudomonas aeruginosa Deacetylase LpxC,”J Med. Chem. 45:3112-3129 (2002). cited by other Mellor et al., “N-Fmoc-Aminooxy-2-Chlorotrityl Polystyrene Resin: A Facile Solid-Phase Methodology for Synthesis of Hydroxamic Acids,” Tetrahedron Letters 38(18):3311-3314 (1997). cited by other Ngu et al., “A New and Efficient Solid Phase Synthesis of Hydroxamic Acids,” J Org. Chem. 62:7088-7089 (1997). cited by other Pirrung et al., “A Convenient Procedure for the Preparation of Amino Acid Hydroxamates from Esters,” J. Org. Chem. 60:8084-8085 (1995). cited by other Pirrung et al., “Inhibition of the Antibacterial Target UPD-(3-0-acy1)-N-acetyglucosamine Deacetylase (LpxC): Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups,” Journal of Medical Chemistry 45(19):4359-4370 (2002). cited by other Angus et al., “Outer Membrane Permeability in Pseudomonas aeruginosa: Comparison of a Wild-type with an Antibiotic-supersusceptible Mutant,” Antimocriob. Agents Chemother. 21(2):299-309 (1982). cited by other Bergeron et al., “Effects of C-4 Stereochemistry and C-4′ Hydroxylation on the Iron Clearing Efficiency and Toxicity of Desferrithiocin Analogues,” J. Med. Chem. 42:2432-2440 (1999). cited by other Boyce et al., “Total Synthesis of Thiangazole, a Novel Naturally Occurring HIV-1 Inhibitor from Polyangium sp,” Tetrahedron 51(26):7321-7330 (1995). cited by other Brooks & Summers, “Modulators of Leukotriene Biosynthesis and Receptor Activation,” J. Med. Chem. 39(14):2629-2654 (1996). cited by other Charette & Chua, “Mild Method for the Synthesis of Thiazolines from Secondary and Tertiary Amides,” J. Org. Chem. 63:908-909 (1998). cited by other Fernandez et al., “Novel Synthesis of 2-Thiazolines,” Tetrahedron Lett. 41:3381-3384 (2000). cited by other Galéotti et al., “Synthesis of Peptidyl Aldehydes from Thiazolidines,” Tetrahedron Left. 38(14):2459-2462 (1997). cited by other Hyland et al., “Cloning, Expression, and Purification of UDP-3-O-Acyl-GlcNA c Deacetylase from Pseudomonas aeruginosa: A Metalloamidase of the Lipid A Biosynthesis Pathway,” J. Bacteriol. 179(6):2029-2037 (1997). cited by other Ito et al., “Synthetic Reactions by Complex Catalysts. XXXI. A Novel and Versatile Method of IIeterocycle Synthesis,” J. Am. Chem. Soc. 95(13):4447-4448 (1973). cited by other Ito et al., “Synthetic Reactions by Complex Catalysts XXXV. A Facile Synthetic Method of Cyclic Imino Ethers and Imino Thioethers,” Syn. Commun. 4(2):97-103 (1974). cited by other Jeng & De Lombaert, “Endothelin Converting Enzyme Inhibitors,” Curr. Pharma. Design 3:597-614 (1997). cited by other Jones, R.N., “Resistance Patterns Among Nosocomial Pathogens,” Chest 119(2)(Supplement):397S-404S (2001). cited by other Matsuda et al., “Nucleosides and Nucleotides. 95. Improved Synthesis of 1-(2-Azido-2-deoxy-β-D-arabinofuranosyl)cytosine (Cytarazid) and -thymine. Inhibitory Spectrum of Cytarazid on the Growth of Various Human Tumor Cells In Vitro,” J. Med. Chem. 34:999-1002 (1991). cited by other Nikaido, H., “Antibiotic Resistance Caused by Gram-negative Multidrug Efflux Pumps,” Clin. Infect. Dis. 27(Suppl 1):S32-S41 (1998). cited by other Pattenden & Thom, “Naturally Occurring Linear Fused Thiazoline-thiazole Containing Metabolites: Total Synthesis of (−)-Didehydromirabazole A, a Cytotoxic Alkaloid from Blue-Green Algae,” J. Chem. Soc. Perkin Trans. 1629-1636 (1993). cited by other Raman et al., “Titanium(IV)-mediated Tandem Deprotection-Cyclodehydration of Protected Cysteine N-Amides: Biomimetic Syntheses of Thiazoline- and Thiazole-containing Heterocycles,” Org. Lett. 2(21):3289-3292 (2000). cited by other Righi et al., “Solution- and Solid-phase Synthesis of 4-Hydroxy-4,5-dihydroisoxazole Derivatives from Enantiomerically Pure N-Tosyl-2,3-aziridine Alcohols,” Org. Lett. 4(4):497-500 (2002). cited by other Sahm et al., “Evaluation of Current Activities of Fluoroquinolones Against Gram-negative Bacilli Using Centralized In Vitro Testing and Electronic Surveillance,” Antimicrob. Agents Chemother. 45(1):267-274 (2001). cited by other Shen & Thomas, “Synthesis of 1,3-Diyncs via Palladium-catalyzed Reaction of 1,1-Dibromo-1-alkenes,” Org. Lett. 2(18):2857-2860 (2000). cited by other Shen & Wang, “The Stille Reaction of 1,1-Dibromo-1-alkenes: Preparation of Trisubstituted Alkenes and Internal Alkynes,” J. Org. Chem. 64:8873-8879 (1999). cited by other Skotnicki et al., “Design Strategies for the Identification of MMP-13 and TACE Inhibitors,” Curr. Opin. Drug Dis. Dev. 6(5):742-759 (2003). cited by other Wipf et al., “Thiolysis of Oxazolines: A New, Selective Method for the Direct Conversion of Peptide Oxazolines into Thiazolines,” Tetrahedron Left. 36(36):6395-6398 (1995). cited by other Witte & Seeliger, “Cyclische Imidsäurcester aus Nitrilen and Aminoalkoholen,” Liebigs Ann. Chem. 996-1009 (1974). cited by other Wyckoff et al., “Antibacterial and Anti-inflammatory Agents That Target Endotoxin,” Trends Microbiol. 6(4):154-159 (1998). cited by other Zask et al., “Inhibition of Matrix Metalloproteinases: Structure Based Design,” Curr. Pharma. Design 2:624-661 (1996). cited by other Zhang et al., “Design, Combinatorial Chemical Synthesis and In vitro Characterization of Novel Urea Based Gelatinase Inhibitors,” Bioorg. Med. Chem. Lett. 9:2823-2826 (1999). cited by other U.S. Appl. No. 12/563,697, Andersen et al. cited by other Chen et al., “Carbohydroxamido-Oxazolidines: Antibacterial Agents That Target Lipid A Biosynthesis,” Bioorg. Med. Chem. Lett. 9:313-18 (1999). cited by other International Preliminary Report on Patentability for PCT/US2004/000433 (Jul. 8, 2005). cited by other International Search Report for PCT/US2004/000433 (Jan. 19, 2005). cited by other Nicolaus, “Symbiotic Approach to Drug Design,” in Decision Making in Drug Research 173-86 (F. Gross ed., 1983). cited by other Pirrung et al., “High-Throughput Catch-and-Release Synthesis of Oxazoline Hydroxamates. Structure—Activity Relationships in Novel Inhibitors of Escherichia coli LpxC: In Vitro Enzyme Inhibition and Antibacterial Properties,” J. Am. Chem. Soc. 125:1575-86 (2003). cited by other Supplementary Partial European Search Report for European Patent Application No. 04700887.5 (Sep. 27, 2006). cited by other Supplementary Partial European Search Report for European Patent Application No. 04700887.5 (Jan. 2, 2007). cited by other Written Opinion of the International Searching Authority for PCT/US2004/000433 (Jan. 19, 2005). cited by other Banker et al., Modern Pharmaceutics, 3rd Edition: p. 596 (1996); Marcel Dekker, Inc., NY. cited by other Kline et al., Journal of Medicinal Chemistry, 45(14):3112-3129 (2002). “Potent, novel in vitro inhibitors of the Pseudomonas aeruginosa deacetylase LpxC.” cited by other Wolff, Manfred E., editor; Burger's Medicinal Chemistry and Drug Discovery, Fifth Edition, vol. I: Principles and Practice: pp. 975-977 (1995); John Wiley & Sons, Inc., NY. cited by other |
| Primary Examiner: | Davis, Brian J |
| Attorney, Agent or Firm: | Parent, Annette S. |
| رقم الانضمام: | edspgr.08084615 |
| قاعدة البيانات: | USPTO Patent Grants |
| الوصف غير متاح. |