375
Views
29
CrossRef citations to date
0
Altmetric
Review

Oxazolidinone antimicrobials: a patent review (2012-2015)

&
Pages 591-605 | Received 01 Feb 2016, Accepted 07 Mar 2016, Published online: 04 Apr 2016

References

  • Torrice M. Antibacterial boom and bust. C&EN. 2013;91:34–37.
  • Butler MS, Blaskovich MA, Cooper MA. Antibiotics in the clinical pipeline in 2013. J Antibiot. 2013;66:571–591.
  • Butler MS, Cooper MA. Antibiotics in the clinical pipeline in 2011. J Antibiot. 2011;64:413–425.
  • Freire-Moran L, Aronsson B, Manz C, et al. Critical shortage of new antibiotics in development against multidrug-resistant bacteria-Time to react is now. Drug Res Update. 2011;14:118–124.
  • Theuretzbacher U. Accelerating resistance, inadequate antibacterial drug pipelines and international responses. Int J Antimicrob Agents. 2012;39:295–299.
  • Piddock LJV. The crisis of no new antibiotics – what is the way forward? Lancet Infect Dis. 2012;12:249–253.
  • Davies SC. Chief medical officer annual report [ cited 2016 Jan 11]. Available from: https://www.gov.uk/government/ publications/chief-medical-officer-annual-report-volume-2
  • Frieden T. Director, U.S. Centers for Disease Control and Prevention [ cited 2016 Jan 11]. Available from: http://www.cdc.gov/AB4F87A3-79A9-4312-94C1-98280AA2A41F/FinalDownload/DownloadId-F25F5D61DAD7062F381AD2837FD8F59B/AB4F87A3-79A9-4312-94C1-98280AA2A41F/drugresistance/threat-report-2013/pdf/ar-threats-2013-508.pdf
  • O’Neill J. UK review on antimicrobial resistance. Securing new drugs for future generations – the pipeline of antibiotics. 2015 [cited 2016 Feb 24]. Available from: http://amr-review.org/sites/default/files/SECURING%20NEW%20DRUGS%20FOR%20FUTURE%20GENERATIONS%20FINAL%20WEB_0.pdf
  • O’Neill J. UK review on antimicrobial resistance. Safe, secure and controlled: managing the supply chain of antimicrobials. 2015 [cited 2016 Feb 24]. Available from: http://amr-review.org/sites/default/files/SafeSecureandControlledShortPaper.pdf
  • O’Neill J. UK review on antimicrobial resistance. Antimicrobial resistance: tackling a crisis for the health and wealth of nations. 2014 [cited 2016 Feb 24]. Available from: http://amr-review.org/sites/default/files/AMR%20Review%20Paper%20-%20Tackling%20a%20crisis%20for%20the%20health%20and%20wealth%20of%20nations_1.pdf
  • Moellering RC, Fishman N. Antimicrobial resistance prevention initiative: proceedings of an expert panel of resistance. Am J Infect Control. 2006;34(5 Suppl):A1–S79.
  • Fauci AS, Touchette NA, Folkers GK. Emerging infectious diseases: a 10-Year perspective from the National Institute of allergy and infectious diseases. Emerg Infect Dis. 2005;11:519–525.
  • Ager S, Gould K. Clinical update on linezolid in the treatment of Gram-positive bacterial infections. Infect Drug Res. 2012;5:87–102.
  • Bassetti M, Righi E. Development of novel antibacterial drugs to combat multiple resistant organisms. Arch Surg. 2015;400:153–165.
  • Holmes NE, Howden BP. What’s new in the treatment of serious MRSA infection? Curr Opin Infect Dis. 2014;27:471–478.
  • Xu H-B, Jiang R-H, Li L, et al. Linezolid in the treatment of MDR-TB: a retrospective clinical study. Int J Tuberc Lung Dis. 2012;16:358–363.
  • Xu H-B, Jiang R-H, Li L, et al. Linezolid-containing regimens for the treatment of drug-resistant tuberculosis in South African children. Int J Tuberc Lung Dis. 2012;16:1588–1593.
  • Leach KL, Brickner SJ, Noe MC, et al. Linezolid, the first oxazolidinone antibacterial agent. Ann N Y Acad Sci. 2011;1222:49–54.
  • Lawrence KR, Adra M, Gillman PK. Serotonin toxicity associated with the use of linezolid: A review of postmarketing data. Clin Infect Dis. 2006;42:1578–1583.
  • Meck JV, Martin DS, D’Aunno DS, et al. Pressor response to intravenous tyramine is a marker of cardiac, but not vascular, adrenergic function. J Cardiovasc Pharmacol. 2003;41:126–131.
  • Shaw KJ, Barbachyn MR. The oxazolidinones: past, present and future. Ann N Y Acad Sci. 2011;1241:48–70.
  • Balaji G, Maharani B, Ravichandran V, et al. Linezolid induced black hairy tongue. Indian J Pharmacol. 2014;46:653–654.
  • Shinabarger DL, Marotti KR, Murray RW, et al. Mechanism of action of oxazolidinones: effects of linezolid and eperezolid on translation reactions. Antimicrob Agents Chemother. 1997;41:2132–2136.
  • Ippolito JA, Kanyo ZF, Wang D, et al. Crystal structure of the oxazolidinone antibiotic linezolid bound to the 50S ribosomal subunit. J Med Chem. 2008;51:3353–3356.
  • Gu B, Kelesidis T, Tsiodras S, et al. The emerging problem of linezolid-resistant Staphylococcus. J Antimicrob Chemother. 2013;68:4–11.
  • Mendes RE, Flamm RK, Hogan PA, et al. Summary of linezolid activity and resistance mechanisms detected during the 2012 LEADER surveillance program for the United States. Antimicrob Agents Chemother. 2014;58:1243–1247.
  • Mendes RE, Deshpande LM, Jones RN. Linezolid update: stable in vitro activity following more than a decade of clinical use and summary of associated resistance mechanisms. Drug Resist Updates. 2014;17:1–12.
  • Shore AC, Brennan OM, Ehricht R, et al. Identification and characterization of the multidrug resistance gene cfr in a Panton–Valentine leukocidin-positive sequence type 8 methicillin-resistant Staphylococcus aureus IVa (USA300) isolate. Antimicrob Agents Chemother. 2010;54:4978–4984.
  • LaMarre J, Mendes RE, Szal T, et al. The genetic environment of the cfr gene and the presence of other mechanisms account for the very high linezolid resistance of Staphylococcus epidermidis isolate 426-3147L. Antimicrob Agents Chemother. 2013;57:1173–1179.
  • Sivextro approval history June 2014 [ cited 2016 Jan 11]. Available from: http://www.drugs.com/history/sivextro.html
  • Kisgen JJ, Mansour H, Unger NR, et al. Tedizolid: A new oxazolidinone antimicrobial. Am J Health-Syst Pharm. 2014;71:621–633.
  • Rybak JM, Marx K, Martin CA. Early experience with tedizolid: clinical efficacy, pharmacodynamics and resistance. Pharmacotherapy. 2014;34:1198–1208.
  • Locke JB, Finn J, Hilgers M, et al. Structure-activity relationships of diverse oxazolidinones for linezolid-resistant Staphylococcus aureus strains possessing the cfr methyltransferase gene or ribosomal mutations. Antimicrob Agents Chemother. 2010;54:5337–5343.
  • Locke JB, Zurenko GE, Shaw KJ, et al. Tedizolid for the management of human infections: in vitro characteristics. Clin Infect Dis. 2014;58(Suppl 1):S35–S42.
  • Rybak JM, Barber KE, Rybak MJ. Current and prospective treatments for multidrug-resistant Gram positive infections. Expert Opin Pharmacother. 2013;14:1919–1932.
  • Moellering RC Jr. Tedizolid: a novel oxazolidinone for Gram-positive infections. Clin Infect Dis. 2014;58(Suppl 1):S1–S3.
  • Flanagan S, Bartizal K, Minassian SL, et al. In vitro, in vivo, and clinical studies of tedizolid to assess the potential for peripheral or central monoamine oxidase interactions. Antimicrob Agents Chemother. 2013;57:3060–3066.
  • Zhanel GG, Love R, Adam H, et al. Tedizolid: A novel oxazolidinone with potent activity against multidrug-resistant Gram-positive pathogens. Drugs. 2015;75:253–270.
  • Im WB, Choi SH, Park J-Y, et al. Discovery of torezolid as a novel 5-hydroxymethyl oxazolidinone antibacterial agent. Eur J Med Chem. 2011;46:1027–1039.
  • Michalska K, Karpiuk I, Krol M, et al. Recent development of potent analogues of oxazolidinone antibacterial agents. Bioorg Med Chem. 2013;21:577–591.
  • Phillips OA, Sharaf L, D’Silva R, et al. Evaluation of the monoamine oxidases inhibitory activity of a small series of 5-(azole)methyl oxazolidinones. Eur J Pharm Sci. 2015;71:56–61.
  • Phillips OA, D’Silva R, Bahta TO, et al. Synthesis and biological evaluation of novel 5-(hydroxamic acid)methyl oxazolidinone derivatives. Eur J Med Chem. 2015;106:120–131.
  • Stokes SS, Morningstar M, Kocis H, et al. New antibacterial agents: patent applications published in 2010. Pharm Pat Analyst. 2012;1:601–620.
  • Keating TA, Lister T, Verheijen JC. New antibacterial agents: patent applications published in 2011. Pharm Pat Analyst. 2014;3:87–112.
  • Rib-X Pharmaceuticals, Incorporated. Biaryl heterocyclic compounds and methods of making and using the same. EP1656 370. 2012.
  • Rib-X Pharmaceuticals, Incorporated. Biaryl heterocyclic compounds and methods of making and using the same. US2012/0010200. 2012.
  • Rib-X Pharmaceuticals, Incorporated. Biaryl heterocyclic compounds and methods of making and using the same. US2014/0073624. 2014.
  • Rib-X Pharmaceuticals, Incorporated. Biaryl heterocyclic compounds and methods of making and using the same. EP2492 264. 2012.
  • Melinta Therapeutics Incorporated. Biaryl heterocyclic compounds and methods of making and using the same. US2015/0072970. 2015.
  • Dong-A ST Co. Limited. Oxazolidinone derivatives. US8420676. 2013.
  • Dong-A ST Co. Limited. Oxazolidinone derivatives. US9163043. 2015.
  • Dong-A ST Co. Limited. Novel oxazolidinone derivatives. US2014/0350059. 2015.
  • Xuanzhu Pharma Co. Limited. Biaryl heterocyclic substituted oxazolidinone antibacterial drug. EP2762479. 2014.
  • Trius Therapeutics, Incorporated. Oxazolidinone containing dimer compounds, compositions and methods to make and use. US8580767. 2013.
  • Actelion Pharmaceuticals Limited. Oxazolidinone antibiotic derivatives. US8114867. 2012.
  • Actelion Pharmaceuticals Limited. Oxazolidinone antibiotics. EP2905283. 2015.
  • Actelion Pharmaceuticals Limited. Tricyclic oxazolidinone antibiotic compounds. EP2344495. 2014.
  • Xuanzhu Pharmac Inc. Limited. Oxazolidinone antibiotics containing fused ring. EP2762480. 2014.
  • Katoh I, Aoki T, Suzuki H et al. Oxazolidinone derivative having fused ring. US2011/0098471. 2011.
  • Entasis Therapeutics Limited. Fused, spirocyclic heteroaromatic compounds for the treatment of bacterial infections. WO2015/181637. 2015.
  • Legochem Biosciences, Inc. Method for the preparation of (R)-3-(3-fluoro-4-(1-methyl-5,6-dihydro-1,2,4-triazin-4-(1H)-yl)phenyl)-5-substitutedmethyl)oxazolidin-2-one deivatives. US2013/0005967. 2013.
  • Jeong J-W, Jung S-J, Lee H-H, et al. In vitro and in vivo activities of LCB01-0371, a new oxazolidinone. Antimicrob Agents Chemother. 2010;54:5359–5362.
  • The PEW Charitable Trusts. Antibiotics currently in clinical development. 2015 Dec 17 [cited 2016 Jan 25]. Available from: http://www.pewtrusts.org/en/multimedia/data-visualizations/2014/antibiotics-currently-in-clinical-development
  • Lee Pharma Limited. Novel oxazolidinone antibacterial compound. WO2015/068173. 2015.
  • Morphochem Aktiengesellschaft Fur Kombinatorische Chemie. Oxazolidinone-quinolone hybrid antibacterials for the parenteral treatment or prophylaxis of bacterial diseases. WO2014/191075. 2014.
  • Locher HH, Seiler P, Chen X, et al. In vitro and in vivo antibacterial evaluation of cadazolid, a new antibiotic for treatment of Clostridium difficile infections. Antimicrob Agents Chemother. 2014;58:892–900.
  • Kali A, Charles MVP, Srirangaraj S. Cadazolid: a new hope in the treatment of Clostridium difficile infections. Australas Med J. 2015;8:253–262.
  • University of South Florida. Derivative N-thiolated 2-oxazolidinone antibiotics. US8703963. 2014.
  • Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Nanjing Changao Pharmaceutical Science and Technology Company Limited. Benzoxazine oxazolidinones compound, preparation method and application thereof. US 2015/0336984. 2015.
  • Sichuan University and Sichua Gooddoctor Pharmaceutical Group Company Limited. Oxazolidinone compounds and their uses in preparation of antibiotics. US 2014/0142144. 2014.
  • Council of Scientific and Industrial Research. Sila analogs of oxazolidinone derivatives and synthesis thereof. US 2014/0296133. 2014.
  • Pandit N, Singla RK, Shrivastava B. Current updates on oxazolidinone and its significance. Internat J Med Chem. 2012; 2012(Article ID 159285):1–24.
  • Venkanna G, Madhusudhan G, Mukkanti K, et al. A facile construction of 5-methylazido-3-aryl 2-oxazolidinone: a key precursor for the synthesis of Linezolid. Der Pharma Chemica. 2012;4(1):428–436.
  • Tammana R, Vemula KK, Guruvindapalli R, et al. An expeditious construction of 3-aryl-5-(substituted methyl)-2-oxazolidinones: a short and efficient synthesis of Linezolid. ARKIVOC. 2012;vi:45–56.
  • Brickner SJ, Hutchinson DK, Barbachyn MR, et al. Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant gram-positive bacterial infections. J Med Chem. 1996;39:673–679.
  • Lee Pharma Limited. Novel process for preparation of linezolid and its novel intermediates. EP2595968. 2015.
  • Lee Pharma Limited. Novel process for preparation of linezolid and its novel intermediates. US2013/0324719. 2013.
  • Lee Pharma Limited. Novel process for preparation of linezolid and its novel intermediates. WO2012/114355. 2012.
  • Reddy PK, Mukkanti K, Rao DM. A novel synthesis of oxazolidinone derivatives (A Key Intermediate of Linezolid). Orient J Chem. 2013;29:1015–1019.
  • Medscape Medical News (2016). Big Pharma pledges to develop new antibiotics, with help [cited 2016 Jan 27]. Available from: http://www.medscape.com/viewarticle/857627?nlid=98083_1842&src=wnl_edit_medp_wir&uac=35373HV&spon=17&impID=970260&faf=1

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.