New β-lactam antibiotics and β-lactamase inhibitors

Expert Opinion on Therapeutic Patents

Volumn 20, Issue 10, 2010, Pages 1277-1293

  Bush, Karen ^a   MacIelag, Mark J ^b  

^a INDIANA UNIVERSITY   (United States)

^b JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

lactam; lactamase; antibacterial; carbacephem; carbapenem; cephalosporin; monobactam; penem; penicillin

Indexed keywords

AMOXICILLIN PLUS CLAVULANIC ACID; AZTREONAM; BAL 30072; BETA LACTAM ANTIBIOTIC; BETA LACTAMASE INHIBITOR; BIAPENEM; BLI 489; CARBACEPHEM DERIVATIVE; CARBAPENEM DERIVATIVE; CEFTAROLINE; CEFTAZIDIME; CEFTOBIPROLE; CEFTRIAXONE; CEPHALOSPORIN DERIVATIVE; CILASTATIN; CXA 101; ERTAPENEM; FR 264205; IMIPENEM; ME 1071; MEROPENEM; MONOBACTAM DERIVATIVE; NXL 104; PENEM DERIVATIVE; PF 03709270; PIPERACILLIN; SULOPENEM; SULOPENEM ETZADROXIL; TEBIPENEM; TOBRAMYCIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; CLINICAL TRIAL; COMMUNITY ACQUIRED PNEUMONIA; DRUG BIOAVAILABILITY; DRUG MECHANISM; DRUG POTENTIATION; GRAM NEGATIVE BACTERIUM; HOSPITAL INFECTION; HUMAN; LUNG INFECTION; MULTIDRUG RESISTANCE; NONHUMAN; RESPIRATORY TRACT INFECTION; REVIEW;

ANTI-BACTERIAL AGENTS; BACTERIAL INFECTIONS; BETA-LACTAM RESISTANCE; BETA-LACTAMASES; BETA-LACTAMS; DRUG RESISTANCE, MULTIPLE, BACTERIAL; DRUG THERAPY, COMBINATION; GRAM-NEGATIVE BACTERIA; HUMANS;

EID: 77956666195     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.2010.515588     Document Type: Review

References (106)

1. Bush K, Jacoby GA. Updated functional classification of beta-lactamases. Antimicrob Agents Chemother 2010;54:969-976
2. Page MGP. Emerging cephalosporins. Expert Opin Emerg Drugs 2007;12:511-524
3. Meiji Seika Kaisha. Penicillin-binding protein 2x (PBP2x) trypsin digest crystals and proteins suitable for X-ray crystal structure analysis. JP2007169170; 2007
4. Meiji Seika Kaisha. Crystal of penicillin-binding protein (PBP) 2b from Streptococcus pneumoniae. WO2007114214; 2007
5. Meiji Seika Kaisha. Sequence of Haemophilus and Escherichia penicillin-binding-protein PBP3 transpeptidase domain. JP2008220317; 2008
6. Meiji Seika Kaisha. Preparation of a crystal of the transpeptidase domain of the penicillin-binding-protein 3 of Haemophilus influenzae. JP2009292776; 2009
7. Slocombe B, Basker MJ, Bentley PH, et al. BRL 17421, a novel beta-lactam antibiotic, highly resistant to beta-lactamases, giving high and prolonged serum levels in humans. Antimicrob Agents Chemother 1981;20:38-46
8. Maderazo EG, Judson S, Pasternak H. Late infections of total joint prostheses. A review and recommendations for prevention. Clin Orthopaed Rel Res 1988;229:131-142
9. Hiramatsu K, Asada K, Tateda-Suzuki E, et al. TOC-39 and TOC-50, a novel class of cephalosporin having a hgh binding affinity to the MRSA-specific penicillin-binding protein, PBP2¢. 33rd Interscience Conference Antimicrobial Agents and Chemotherapy; New Orleans, LA; 1993. Abstract 888
10. Hanaki H, Akagi H, Masaru Y, et al. TOC-39, a novel parenteral broad-spectrum cephalosporin with excellent activity against methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother 1995;39:1120-1126
11. Bristol-Myers Squibb Co., USA. Preparation of cephalosporin derivatives for use as antibacterial agents. WO9823621; 1998
12. Fung-Tomc J, Pucci M, Gradelski E, et al. Anti-staphylococcal activity of a novel MRSA (methicillin-resistant Staphylococcus aureus) cephem BMS-247243. 40th Interscience Conference Antimicrobial Agents and Chemotherapy; 2000. Abstract 1063
13. Hecker SJ, Glinka TW, Cho A, et al. Discovery of RWJ-54428 (MC-02,479), a new cephalosporin active against resistant gram-positive bacteria. J Antibiotics 2000;53:1272-1281
14. Fukuoka T, Koga T, Ishii C, et al. Antibacterial activity of CS-023 against MRSA and Pseudomonas aeruginosa. 42nd Interscience Conference Antimicrobial Agents and Chemotherapy; San Diego, CA; 2002. Abstract F-324
15. Kawamoto I, Shimoji Y, Kanno O, et al. Synthesis and structure-activity relationships of novel parenteral carbapenems, CS-023 (R-115685) and related compounds containing an amidine moiety. J Antibiotics 2003;56:565-579
16. Page MGP. Anti-MRSA beta-lactams in development. Curr Opin Pharmacol 2006;6:480-485
17. Noel GJ, Bush K, Bagchi P, et al. A randomized, double-blind trial comparing ceftobiprole medocaril with vancomycin plus ceftazidime for the treatment of patients with complicated skin and skin-structure infections. Clin Infect Dis 2008;46:647-655
18. Noel GJ, Strauss RS, Amsler K, et al. Results of a double-blind, randomized trial of ceftobiprole treatment of complicated skin and skin structure infections caused by gram-positive bacteria. Antimicrob Agents Chemother 2008;52:37-44
19. Talbot GH, Thye D, Das A, et al. Phase 2 study of ceftaroline versus standard therapy in treatment of complicated skin and skin structure infections. Antimicrob Agents Chemother 2007;51:3612-3616
20. Eckburg P, Friedland HD, Lee J, et al. Focus 1 and 2: randomized, double-blinded, multicenter phase 3 trials of the efficacy and safety of ceftaroline (CPT) vs ceftriaxone (CRO) in community-acquired pneumonia (CAP). 49th Interscience Conference Antimicrobial Agents and Chemotherapy; San Francisco, CA; 12-15 September 2009. Abstract L1345a
21. Amsler KM, Davies TA, Shang W, et al. In vitro activity of ceftobiprole against pathogens from two phase 3 clinical trials of complicated skin and skin structure infections. Antimicrob Agents Chemother 2008;52:3418-3423
22. Forest Laboratories Holdings Ltd. Compositions and methods of treatment comprising ceftaroline. WO2010025328, 2010
23. Shandong Kbp Biomedical Co. Preparations of cephalosporin derivatives for treatment of infectious diseases. CN101245077; 2008
24. Toda A, Ohki H, Yamanaka T, et al. Synthesis and SAR of novel parenteral anti-pseudomonal cephalosporins: discovery of FR264205. Bioorg Med Chem Lett 2008;18:4849-4852
25. Livermore DM, Mushtaq S, Ge Y, et al. Activity of cephalosporin CXA-101 (FR264205) against Pseudomonas aeruginosa and Burkholderia cepacia group strains and isolates. Intl J Antimicrob Agents 2009;34:402-406
26. Boucher HW, Talbot GH, Bradley JS, et al. Bad bugs, no drugs: no ESKAPE! An update from the Infectious Diseases Society of America. Clin Infect Dis 2009;48:1-12
27. Landman D, Bratu S, Kochar S, et al. Evolution of antimicrobial resistance among Pseudomonas aeruginosa, Acinetobacter baumannii and Klebsiella pneumoniae in Brooklyn. NY J Antimicrob Chemother 2007;60:78-82
28. Astellas Pharma, Inc. Preparation of cephem compounds for therapeutic use in antimicrobial pharmaceutical compositions. WO2007119511; 2007
29. Shionogi & Co. Preparation of cephalosporins having catechol group as antibacterial agents. WO2010050468; 2010
30. Harris AM. Catechol-substituted cephalosporins. Curr Opin Invest Drugs 1993;2:109-118
31. Nikaido H, Rosenberg EY. Cir and Fiu proteins in the outer membrane of Escherichia coli catalyze transport of monomeric catechols: study with beta-lactam antibiotics containing catechol and analogous groups. J Bacteriol 1990;172:1361-1367
32. Curtis NA, Eisenstadt RL, East SJ, et al. Iron-regulated outer membrane proteins of Escherichia coli K-12 and mechanism of action of catechol-substituted cephalosporins. Antimicrob Agents Chemother 1988;32:1879-1886
33. Trine Pharmaceuticals, Inc., USA. Preparation of carbacephem beta-lactam antibiotics for the treatment of bacterial infections. WO2004-US13054; 2004
34. Glinka T, Blais J, Dudley M, et al. A novel series of 3-heteroarylthio carbacephems with activity against resistant Gram-positive bacteria. 45th Interscience Conference Antimicrobial Agents and Chemotherapy; San Francisco, CA; 2005. Abstract 1455
35. Griffith D, Dudley MN, Glinka T, et al. Preclinical pharmacokinetics and serum protein binding of BP-102 and other members of a novel series of carbacephems active against resistant Gram positive bacteria. 45th Interscience Conference Antimicrobial Agents and Chemotherapy; San Francisco, CA; 2005. Abstract F-1458.
36. Jones RN, Sader HS, Fritsche TR, et al. Antimicrobial activity of BP-102, a novel carbacephem, tested against H. influenzae, M. catarrhalis and various Gram-positive cocci. 45th Interscience Conference Antimicrobial Agents and Chemotherapy; San Francisco, CA; 2005. Abstract F-1457
37. Blanca Pharmaceuticals. Preparation of carbacephem beta-lactam antibiotics and beta-lactamase inhibitors. US2008146535; 2008
38. Achaogen. Carbacephem beta-lactam antibiotics. WO2009055696; 2009
39. Achaogen. Carbacephem beta-lactam antibiotics. WO2010030811; 2010
40. Achaogen. Carbacephem beta-lactam antibiotics. WO2010030810; 2010
41. Gootz T, Retsema J, Girard A, et al. In vitro activity of CP-65,207, a new penem antimicrobial agent, in comparison with those of other agents. Antimicrob Agents Chemother 1989;33:1160-1166
42. Retsema J, Girard A, Anderson M, et al. In vitro and in vivo evaluation of a new penem antibiotic: CP-65,207. 38th Interscience Conference Antimicrobial Agents and Chemotherapy; San Diego, CA; 1988. Abstract 221
43. Pfizer Products, Inc. Preparation of penem prodrugs for the treatment of bacterial infections. WO2008059367; 2008
44. Wujcik CE, Kadar EP. Reduction of in-source collision-induced dissociation and thermolysis of sulopenem prodrugs for quantitative liquid chromatography/electrospray ionization mass spectrometric analysis by promoting sodium adduct formation. Rapid Commun Mass Spectrom 2008;22:3195-3206
45. Clinical Trials.gov 2009. Available from http://clinicaltrials. gov/ct2/show?term=sulopenem&rank=1 [Cited 3 August 2010]
46. Clinical trials.gov; 2010. Available from: http://clinicaltrials. gov/ct2/show/NCT00759564?term=sulopenem&rank=2 [Cited 3 August 2010]
47. Upchurch J, Rosemore M, Tosiello R, et al. Randomized double-blind study comparing 7-and 10-day regimens of faropenem medoxomil with a 10-day cefuroxime axetil regimen for treatment of acute bacterial sinusitis. Otolaryngol Head Neck Surg 2006;135:511-517
48. Amplyx Pharmaceuticals. Antimicrobials. WO2010065110; 2010
49. Germany. Bactericidal anti-MRSA active pharmaceutical composition containing carbapenems. WO2008141764; 2008
50. Meiji Seika Kaisha. Preparation of 2-ethenylthiocarbapenem derivatives as antibacterial agents. WO2006109823; 2006
51. Meiji Seika Kaisha. Preparation carbapenems and oral antibacterial agents containing them. JP2008074803; 2008
52. Kobayashi R, Konomi M, Hasegawa K, et al. In vitro activity of tebipenem, a new oral carbapenem antibiotic, against penicillin-nonsusceptible Streptococcus pneumoniae. Antimicrob Agents Chemother 2005;49:889-894
53. Plantan I, Selic L, Mesar T, et al. 4-Substituted trinems as broad spectrum beta-lactamase inhibitors: structure-based design, synthesis, and biological activity. J Med Chem 2007;50:4113-4121
54. Lek Pharmaceuticals D.D. Antibacterial combination of a tricyclic carbapenem and an antibiotic. WO2008098955; 2008
55. LEK Pharmaceuticals D.D. Preparation of new trinem antibiotics and inhibitors of beta-lactamases. WO2009153297; 2009
56. Lek Pharmaceuticals D.D. Use of inhibitor of beta-lactamases and its combination with beta-lactam antibiotics for treatment of bacterial infection. WO2009095387; 2009
57. Lek Pharmaceuticals D.D. Antibacterial combination of a tricyclic carbapenem and an antibiotic. EP1958630; 2008
58. Paukner S, Hesse L, Prezelj A, et al. In vitro activity of LK-157, a novel tricyclic carbapenem as broad-spectrum beta-lactamase inhibitor. Antimicrob Agents Chemother 2009;53:505-511
59. Lek Pharmaceuticals D.D. Use of inhibitor of beta-lactamases and its combination with beta-lactam antibiotics for treatment of bacterial infection. EP2085084; 2009
60. Basilea Pharmaceutica A.-G. Useful combinations of monobactam antibiotics with beta-lactamase inhibitors. WO2007065288; 2007
61. Basilea Pharmaceutica A.-G. Combination medicaments for treating bacterial infections. WO2008116813; 2008
62. Basilea Pharmaceutica A.-G. Process for the preparation of 2-(primary-/secondary-amino)hydrocarbyl)-carbamoyl-7-oxo-2,6-diazabicyclo[3.2.0. ] heptane-6-sulfonic acid derivatives. WO2009071638; 2009
63. Russo TA, Page MG, Beanan J, et al. BAL30072 is active against Acinetobacter baumannii in a rat soft-tissue infection model. 49th Interscience Conference Antimicrobial Agents and Chemotherapy; San Francisco, CA; 12-15 September 2009. Abstract F1-1486
64. Page MGP, Heim J. New molecules from old classes: revisiting the development of beta-lactams. IDrugs 2009;12:561-565
65. Page MGP, Dantier C, Desarbre E. In vitro properties of BAL30072, a novel siderophore sulfactam with activity against multiresistant gram-negative bacilli. Antimicrob Agents Chemother 2010;54:2291-2302
66. Bush K, Freudenberger JS, Sykes RB. Interaction of azthreonam and related monobactams with beta-lactamases from gram-negative bacteria. Antimicrob Agents Chemother 1982;22:414-420
67. Glade Organics Private Ltd. Synergistic antibacterial combinations of aztreonam with meropenem or ertapenem. WO2010064261; 2010
68. Page MGP, Desarbre E, Geier C, et al. Activity of monobactam beta-lactamase inhibitor combinations against beta-lactam-resistant Gram-negative bacteria. 47th Interscience Conference Antimicrobial Agents and Chemotherapy; Chicago, IL; 17-20 September 2007. Abstract F1-311
69. Page MGP, Desarbre E, Geier C, et al. Activity of BAL30376 against Gram-negative bacteria. 47th Interscience Conference Antimicrobial Agents and Chemotherapy; Chicago, IL; 17-20 September 2007. Abstract F1-312
70. Bush K, Macalintal C, Rasmussen BA, et al. Kinetic interactions of tazobactam with beta-lactamases from all major structural classes. Antimicrob Agents Chemother 1993;37:851-858
71. Wyeth. Bicyclic 6-alkylidene-penem beta-lactamase inhibitors and beta-lactam antibiotic combination: a broad spectrum antibiotic. WO2007016134; 2007
72. Wyeth. Tricyclic 6-alkylidene-penem beta-lactamase inhibitors and beta-lactam antibiotic combination for treatment of resistant infections. US2007027130; 2007
73. Petersen PJ, Jones CH, Venkatesan AM, et al. Efficacy of piperacillin combined with the penem beta-lactamase inhibitor BLI-489 in murine models of systemic infection. Antimicrob Agents Chemother 2009;53:1698-1700
74. Petersen PJ, Jones CH, Venkatesan AM, et al. Establishment of in vitro susceptibility testing methodologies and comparative activities of piperacillin in combination with the penem {beta}-lactamase inhibitor BLI-489. Antimicrob Agents Chemother 2009;53:370-384
75. Southern Methodist University. Preparation and antibacterial activity of beta-lactamase inhibitory compounds. US2010009954; 2010
76. Orchid Chemicals & Pharmaceuticals Ltd. Preparation of 2-substituted methyl penam derivatives for the treatment of bacterial infections. US2008015156; 2008
77. Miossec C, Poirel L, Livermore D, et al. In vitro activity of the new beta-lactamase inhibitor NXL104: restoration of ceftazidime (CAZ) efficacy against carbapenem-resistant Enterobacteriaceae strains. 47th Interscience Conference Antimicrobial Agents and Chemotherapy; Chicago, IL; 17-20 September 2007. Abstract F1-318
78. Livermore DM, Mushtaq S, Warner M, et al. NXL104 combinations versus Enterobacteriaceae with CTX-M extended-spectrum beta-lactamases and carbapenemases. J Antimicrob Chemother 2008;62:1053-1056
79. Novexel. Use of (1R,2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide, 7-oxo-6-(sulfooxy)-, monosodium salt as a diagnostic reagent for detecting serine beta-lactamases. EP2135959; 2009
80. Levasseur P, Girard AM, Miossec C, et al. Efficacy of NXL104 (previously AVE1330A), a novel broad spectrum beta-lactamase inhibitor, in combination with ceftazidime (CAZ) in murine septicaemia and pneumonia. 45th Interscience Conference Antimicrobial Agents and Chemotherapy; San Francisco, CA; 2005
81. Novexel. New nitrogen-heterocyclic compounds, their preparation and their use as antibacterial drugs. WO2008142285; 2008
82. Merck & Co., Inc. 7-Oxo-2,6-Diazabicyclo[3.2.0]heptane-6-sulfonic acid derivatives as beta-lactamase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of bacterial infections. WO2008039420; 2008
83. Merck & Co., Inc. Preparation of sulfooxydiazabicyclooctanecarboxamide derivatives and analogs for use as beta-lactamase inhibitors. WO2009091856 2009
84. Nagarajan R, Pratt RF. Thermodynamic evaluation of a covalently bonded transition state analogue inhibitor: inhibition of beta-lactamases by phosphonates. Biochemistry 2009;43:9664-9673
85. Merck & Co., Inc., USA; Methylgene, Inc. Sulfonylamidomethylphosphonates as inhibitors of beta-lactamases for decreasing of bacterial resistance to antibiotics. WO2007139729; 2007
86. Merck & Co., Inc., USA; Methlgene, Inc. (Hetero) arylsulfonamidomethylphosphonate derivatives as beta-lactamase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of bacterial infection. WO2008073142; 2008
87. Protez Pharmaceuticals. Beta-lactamase inhibitors. WO2009064413; 2009
88. Wouters J, Fonze E, Vermeire M, et al. Crystal structure of Enterobacter cloacae 908R class C beta-lactamase bound to iodo-acetamido-phenyl boronic acid, a transition-state analogue. Cell Molec Life Sci 2003;60:1764-1773
89. Chen Y, Minasov G, Roth TA, et al. The deacylation mechanism of AmpC beta-lactamase at ultrahigh resolution. J Amer Chem Soc 2006;128:2970-2976
90. Merck & Co., Inc., USA. Succinic acid derivative metallo-beta- lactamase inhibitors, their preparation, and their use in treating bacterial infections. WO2001030149; 2000
91. Toney JH, Hammond GG, Fitzgerald PM, et al. Succinic acids as potent inhibitors of plasmid-borne IMP-1 metallo-beta-lactamase. J Biolog Chem 2001;276:31913-31918
92. Meiji Seika Kaisha. Preparation of maleic acid derivatives as metallo-beta-lactamase inhibitors. US2008090825; 2008
93. Morinaka A, Ohkuma K, Matsumoto K, et al. In vivo efficacy of ME1071, a novel metallo-beta-lactamase (MBL) inhibitor, in combination with carbapenems agasint MBL-producing Pseudomonas aeruginosa in a murine pneumonia model. 49th Interscience Conference Antimicrobial Agents and Chemotherapy; San Francisco, CA; 12-15 September 2009. Abstract F1-1491
94. Meiji Seika Kaisha. Pharmaceutical compositions containing maleic acid derivatives and cephem antibiotics. JP2009040743; 2009
95. Kim SK, Sims CL, Wozniak SE, et al. Antibiotic resistance in bacteria: novel metalloenzyme inhibitors. Chem Biol Drug Design 2009;74:343-348
96. Can. Preparation of naphthohydrazides, benzohydrazides and pyridohydrazides as inhibitors of Class B and Class D beta-lactamases. WO2009114921; 2009
97. Roll DM, Yang Y, Wildey MJ, et al. Inhibition of metallo-beta-lactamases by pyridine monothiocarboxylic acid analogs. J Antibiotics 2010;63:255-257
98. Orchid Chemicals & Pharmaceuticals Ltd. Process for the preparation of a cephalosporin antibiotic. IN2003MA00502; 2007
99. Orchid Chemicals & Pharmaceuticals Ltd. An improved process for the preparation of a cephalosporin antibiotic. IN2005CH00052; 2007
100. Orchid Chemicals & Pharmaceuticals Ltd. Novel electrochemical system for chlorination of azetidinone derivatives. IN2002MA00639; 2007
101. Orchid Chemicals & Pharmaceuticals Ltd. Improved process for the preparation of the carbapenem antibiotic imipenem. IN2005CH01178; 2007
102. Orchid Chemicals & Pharmaceuticals Ltd. Process for the preparation of beta-lactam antibiotic Faropenem. WO2008035153; 2008
103. Ranbaxy Laboratories Ltd. Processes for the preparation of penems and their intermediates. WO2007004028; 2007
104. Zhejian Jinhua Conba Bio-Pharm Co., Ltd. Method for synthesis of antibacterial agent sodium faropenem. CN1884284; 2006
105. Jacoby G, Bush K. Beta-lactamase classification and amino acid sequences for TEM, SHV and OXA extended-spectrum and inhibitor resistant enzymes; 2010. Available from: http://www.lahey. org/Studies/ [Cited 4 August 2010]
106. Pournaras S, Poulou A, Voulgari E, et al. Detection of the new metallo-beta-lactamase VIM-19 along with KPC-2, CMY-2 and CTX-M-15 in Klebsiella pneumoniae. J Antimicrob Chemother 2010;65:1604-1607