Synthetic molecules as DprE1 inhibitors: A patent review

References

• Natarajan A, Beena PM, Devnikar AV, et al. A systemic review on tuberculosis. Indian J. Tuberc. 2020;67(3):295–311.
   PubMedGoogle Scholar
• World Health Organization. Global tuberculosis report. 2019. Available from: https://www.who.int/tb/publications/global_report/en/ (Accessed on September 15, 2020).
   Google Scholar
• Lee JY, Kim BJ, Koo HK, et al. Diagnostic potential of IgG and IgA responses to mycobacterium tuberculosis antigens for discrimination among active tuberculosis, latent tuberculosis infection, and non-infected individuals. Microorganisms. 2020;8(7):979.
   Web of Science ®Google Scholar
• Ben Amar J, Dhahri B, Aouina H, et al. Traitement de la tuberculose treatment of tuberculosis]. Rev Pneumol Clin. 2015;71(2–3):122–129.
   PubMedGoogle Scholar
• Parekh MJ, Schluger NW. Treatment of latent tuberculosis infection. Ther Adv Respir Dis. 2013;7(6):351–356.
   PubMed Web of Science ®Google Scholar
• Unissa AN, Subbian S, Hanna LE, et al. Overview on mechanisms of isoniazid action and resistance in Mycobacterium tuberculosis. Infect Genet Evol. 2016;45:474–492.
   PubMed Web of Science ®Google Scholar
• Vasava MS, Bhoi MN, Rathwa SK, et al. Drug development against tuberculosis: past, present and future. Indian J. Tuberc. 2017;64(4):252–275.
   PubMedGoogle Scholar
• Keam SJ. Pretomanid: first approval. Drugs. 2019;79(16):1797–1803.
   PubMed Web of Science ®Google Scholar
• Rabahi MF, Jlrd SJ, Ferreira ACG, et al. Tuberculosis treatment. J. Bras. Pneumol. 2017;43(6):472–486. PMID: 29340497; PMCID: PMC5792048 Erratum in: J. Bras. Pneumol. 2018;44(4):340
   PubMed Web of Science ®Google Scholar
• WHO consolidated guidelines on tuberculosis: Module 4: Treatment - Drug-resistant tuberculosis treatment [Internet]. Geneva: World Health Organization; 2020. PMID: 32603040.
   Google Scholar
• WHO consolidated guidelines on drug-resistant tuberculosis treatment. Geneva: World Health Organization; 2019. PMID: 30946559.
   Google Scholar
• Singh R, Dwivedi SP, Gaharwar US, et al. Recent updates on drug resistance in Mycobacterium tuberculosis. J Appl Microbiol. 2020;128(6):1547–1567.
   PubMed Web of Science ®Google Scholar
• Campaniço A, Moreira R, Lopes F. Drug discovery in tuberculosis. new drug targets and antimycobacterial agents. Eur J Med Chem. 2018;150:525–545.
   PubMed Web of Science ®Google Scholar
• Lamichhane G. Novel targets in M. tuberculosis: search for new drugs. Trends Mol Med. 2011;17(1):25–33.
   PubMed Web of Science ®Google Scholar
• Shetye GS, Franzblau SG, Cho S. New tuberculosis drug targets, their inhibitors, and potential therapeutic impact. Transl Res. 2020;220:68–97.
   PubMed Web of Science ®Google Scholar
• Riccardi G, Pasca MR, Chiarelli LR, et al. The DprE1 enzyme, one of the most vulnerable targets of Mycobacterium tuberculosis. Appl Microbiol Biotechnol. 2013;97(20):8841–8848.
   PubMed Web of Science ®Google Scholar
• Trefzer C, Rengifo-Gonzalez M, Hinner MJ, et al. Benzothiazinones: prodrugs that covalently modify the decaprenylphosphoryl-β-D-ribose 2ʹ-epimerase DprE1 of Mycobacterium tuberculosis. J Am Chem Soc. 2010;132(39):13663–13665.
   PubMed Web of Science ®Google Scholar
• Makarov V, Manina G, Mikusova K, et al. Benzothiazinones kill Mycobacterium tuberculosis by blocking arabinan synthesis. Science. 2009;324(5928):801–804.
   PubMed Web of Science ®Google Scholar
• Hoagland DT, Liu J, Lee RB, et al. New agents for the treatment of drug-resistant Mycobacterium tuberculosis. Adv Drug Deliv Rev. 2016;102:55–72.
   PubMed Web of Science ®Google Scholar
• Buroni S, Pasca MR, Al DJLR, et al. Antituberculars which target decaprenylphosphoryl-β-D-ribofuranose 2ʹ-oxidase DprE1: state of art. Appl Microbiol Biotechnol. 2012;94(4):907–916.
   PubMed Web of Science ®Google Scholar
• Mikusová K, Makarov V, Neres J. DprE1–from the discovery to the promising tuberculosis drug target. Curr Pharm Des. 2014;20(27):4379–4403. .
   PubMed Web of Science ®Google Scholar
• Gawad J, Bonde C. Decaprenyl-phosphoryl-ribose 2ʹ-epimerase (DprE1): challenging target for antitubercular drug discovery. Chem Cent J. 2018;12(1):72. .
   PubMedGoogle Scholar
• Makarov V, Mikušová K. Development of Macozinone for TB treatment: an update. Appl Sci. 2020;10(7):2269. .
   Google Scholar
• Mariandyshev AO, Khokhlov AL, Smerdin SV, et al. [The main results of clinical trials of the efficacy, safety and pharmacokinetics of the perspective antituberculosis drug makozinone (PBTZ169)]. Ter Arkh. 2020;92(3):61–72.
   PubMed Web of Science ®Google Scholar
• Hariguchi N, Chen X, Hayashi Y, et al. OPC-167832, a novel carbostyril derivative with potent antituberculosis activity as a DprE1 inhibitor. antimicrob. Agents Chemother. 2020;64(6):e02020–19.
   PubMed Web of Science ®Google Scholar
• Kb S, Kumari A, Shetty D, et al. Structure based pharmacophore modelling approach for the design of azaindole derivatives as DprE1 inhibitors for tuberculosis. J Mol Graph Model. 2020;101:107718.
   PubMed Web of Science ®Google Scholar
• Lluis BP, inventor; Glaxosmithkline intellectual property development limited, assignee. antituberculosis agent. United States Patent US 10624893 B2. 2020, April 21.
   Google Scholar
• Carlos AG, inventor; Glaxosmithkline intellectual property development limited, assignee. novel tetrazole compounds and their use in the treatment of tuberculosis. United States Patent Application Publication US 20200231555 A1. 2020, July 23.
   Google Scholar
• Esther PDF, inventor; GlaxoSmithKline intellectual property development limited, assignee. novel compounds. United States Patent Application Publication US20200170997A1. 2020, June 4.
   Google Scholar
• Esther PDF, inventor; GlaxoSmithKline intellectual property development limited, assignee. novel compounds. United States Patent Application Publication US20200253967A1. 2020, August 13.
   Google Scholar
• David BA, inventor; GlaxoSmithKline intellectual property development limited, assignee. sanfetrinem or a salt or ester thereof for use in treating Mycobacterial infection. United States Patent Application Publication US20200289462A1. 2020. September 17.
   Google Scholar
• Esther PDF, inventor; GlaxoSmithKline intellectual property development limited, assignee. novel compounds. International Publication Number WO2019034700A1. 2019, February 21.
   Google Scholar
• Carlos AG, inventor; GlaxoSmithKline intellectual property development limited, assignee. novel tetrazole compounds and their use in the treatment of tuberculosis. International Publication Number WO2019034729A1. 2019, February 21.
   Google Scholar
• Florian K, inventor; leibniz-institu fur naturstoff-forschung und infektionsbiologie E.V. Hans-Knoell institut, assignee. new antimicrobial compounds, their use for the treatment of mammalian infections and a new metabolic mechanism. International Publication Number WO2018055048A1. 2018, March 29.
   Google Scholar
• Yoshikazu H, inventor; Otsuka pharmaceutical company limited, assignee. pharmaceutical composition. Japanese Patent Application Publication JP2017141224A. 2017, August 17.
   Google Scholar
• Makarov AV, inventor; Alere International, assignee. Benzothiazinone derivatives and their use as antibacterial agents. United States Patent US7863268B2. 2011, January 4.
   Google Scholar
• Shimizu H, inventor; Otsuka Pharmaceutical Co., Ltd., assignee. heterobicyclic compounds and their use for the treatment of tuberculosis. United States Patent US10053446B2. 2018, August 21.
   Google Scholar
• Shimizu H, inventor; Otsuka Pharmaceutical Co., Ltd., assignee. heterobicyclic compounds and their use for the treatment of tuberculosis. United States Patent US10464926B2. 2019, November 5.
   Google Scholar
• Shirude PS, inventor; global alliance for TB drug development, assignee. azaindole compounds, synthesis thereof, and methods of using the same. United States Patent US9163020B2. 2015, October 20.
   Google Scholar
• Makarov V, inventor; ecole polytechnique federale de lausanne, assignee. 2-piperazin-1-yl-4H-1,3-benzothiazin-4-one derivatives and their use for the treatment of mammalian infections. United States Patent US8796264B2. 2014, August 5.
   Google Scholar
• Changlun A, inventor; Qingdao Jiao pharmaceutical technology company limited, assignee. azaindole amide compounds and preparation method and application thereof. Chinese Patent Application Publication CN111393435A. 2020, July 10.
   Google Scholar
• Chunhua Q, inventor; Soochow University, assignee. Benzothiazinone derivatives, preparation method thereof, and application as antituberculosis drugs. Chinese Patent Application Publication CN111303075A. 2020, June 19.
   Google Scholar
• Chunhua Q, inventor; Soochow University, assignee. Benzothiazinone compound, preparation method thereof, and application as antituberculosis medicine. Chinese Patent Application Publication CN111269197A. 2020, June 12.
   Google Scholar
• Haihong H, inventor; institute of materia medica, Chinese academy of medical sciences, assignee. 2-arylamino-substituted thienylimide ester compound and preparation method and application thereof. Chinese Patent Application Publication CN110759889A. 2020, February 7.
   Google Scholar
• Desai R, inventor; Cadila healthcare limited, assignee. Condensed azaheteroaryl compounds having antibacterial activity against tuberculosis bacteria. International Publication Number WO2019239382A1. 2019, December 19.
   Google Scholar
• Huiyuan G, inventor; institute of medicinal biotechnology, Chinese academy of medical sciences, assignee. diazospiro fragment-containing imidazo[1,2-alpha]pyridine-3-amide compound and preparation method and application thereof. Chinese Patent Application Publication CN109503631A. 2019, March 22.
   Google Scholar
• Jie C, inventor; Wuhan Huajie century biopharmaceutical company limited, assignee. DprE1 enzyme inhibitor. Chinese Patent Application Publication CN108623527A. 2018, October 9.
   Google Scholar
• Lin D, inventor; Chengdu Normal University, assignee. Nitrofuran antituberculous component. Chinese Patent Application Publication CN108558858A. 2018, September 21.
   Google Scholar
• Chao G, inventor; Sichuan University, assignee. Benzothiazine derivative, a preparation method, and uses thereof. Chinese Patent Application Publication CN108456204A. 2018, August 28.
   Google Scholar
• Nikolaevich CV, inventor; FGBUN Institut Organicheskogo Sinteza im. I. Ya. Postovskogo Uralskogo Otdeleniya RAN, assignee. 5-Fluoro-2-(4-ethoxycarbonyldipiperazine-1-yl)-1,3-benzothiazine-4-one, which has anti-tuberculosis activity. Russian Patent RU2663848C1. 2018, August 10.
   Google Scholar
• Florian K, inventor; Leibniz-Institu fur naturstoff-forschung und infektionsbiologie E.V. Hans-Knoell Institut, assignee. new antimicrobial compounds, their use for the treatment of mammalian infections and a new metabolic mechanism. European Patent Application Publication EP3515920A1. 2019, July 31.
   Google Scholar
• Borisovna BO Inventor; FED Gosudarstvennoe Unitarnoe Predpriyatie Gosudarstvennyj Ordena Trudovogo Krasnogo Znameni Nauchno, assignee. Quaternary ammonium derivatives of 2-aminothiophen-3-carboxylates having antituberculosis activity. Russian Patent RU2629369C1. 2017, August 29.
   Google Scholar
• Miller MJ, inventor; University of Notre Dame DU LAC, assignee. 1,3-Benzothiazinone, sulfoxide, and sulfone compounds with electrophilic substituent. United States Patent US9708339B2. 2017, Jul 18.
   Google Scholar
• Miller MJ, inventor; University of Notre Dame DU LAC, assignee. 1,3-benzothiazinone sulfoxide and sulfone compounds. United States Patent US9481683B2. 2016, November 1.
   Google Scholar
• Chatterjee AK, inventor; the California institute for biomedical research, assignee. compounds for treatment of drug-resistant and persistent tuberculosis. United States Patent Application Publication US20160194299A1. 2016, July 7, 2016.
   Google Scholar
• Yuquan W, inventor; Sichuan university, assignee. benzothiazine-thione derivatives, preparation method thereof and purpose thereof. Chinese Patent CN102276598B. 2014, November 5.
   Google Scholar
• Yulevich LA, inventor; FED gosudarstvennoe uchrezhdenie fed issledovatelskij tsentr fundamentalnye osnovy biotekhnologii, assignee. Pyranoindoles with antituberculosis activity. Russian Patent RU2675240C1. 2018, December 18.
   Google Scholar
• Shirude PS, inventor; foundation for neglected disease research, assignee. benzimidazoles derivatives as antituberculosis agents. International Publication Number WO2020188405A1. 2020, September 24.
   Google Scholar
• Bandodkar B, Shandil RK, Bhat J, et al. Two decades of TB drug discovery efforts - what have we learned? Appl Sci. 2020;10(16):5704.
   Google Scholar
• Mikušová K, Ekins S. Learning from the past for TB drug discovery in the future. Drug Discov Today. 2017;22(3):534–545.
   PubMed Web of Science ®Google Scholar
• Degiacomi G, Belardinelli JM, Pasca MR, et al. Promiscuous targets for antitubercular drug discovery: the paradigm of DprE1 and MmpL3. Appl Sci. 2020;10(2):623.
   Google Scholar