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Review

Discovery and optimizing polycyclic pyridone compounds as anti-HBV agents

, , , , , & show all
Pages 715-721 | Received 23 Oct 2019, Accepted 22 Jul 2020, Published online: 09 Aug 2020

References

  • Chan RY, Sung WL, Jeong WJ, et al. Update on hepatitis B virus infection. World J Gastroenterol. 2014;20:13293–13305.
  • Caballero A, Tabernero D, Buti M, et al. Hepatitis B virus: the challenge of an ancient virus with multiple faces and a remarkable replication strategy. Antiviral Res. 2018;158:34–44.
  • Quivy JP, Testoni B, Zoulim F, et al. An inhibitor for use for preventing and/or treating an infection with hepatitis B virus. WO2019043193A1. 2019.
  • Dienstag JL. Hepatitis B virus infection. N Engl J Med. 2008;359:1486–1500.
  • Feng S, Gao L, Han X, et al. Discovery of Small Molecule Therapeutics for Treatment of Chronic HBV Infection. ACS Infect Dis. 2018;4:257–277.
  • Dienstag JL. Hepatitis B virus infection. [Erratum to document cited in CA149:524366]. N Engl J Med. 2010;363:298.
  • Pei Y, Wang C, Yan SF, et al. Past, current, and future developments of therapeutic agents for treatment of chronic Hepatitis B virus infection. J Med Chem. 2017;60:6461–6479.
  • Suto MJ. Treatment of hepatitis B virus infection. US20160303122A1. 2016.
  • Hu K, Cheng Z, Sun G. Application of sodium selenite in preparation of medicine for treating or preventing hepatitis B virus infection. CN104586882A1. 2015.
  • Chahine EB, Sucher AJ, Hemstreet BA. Sofosbuvir/Velpatasvir: the First Pangenotypic Direct-Acting Antiviral Combination for Hepatitis C. Ann Pharmacother. 2017;51:44–53.
  • Greig SL, Deeks ED. Abacavir/dolutegravir/lamivudine single-tablet regimen: a review of its use in HIV-1 infection. Drugs. 2015;75:503–514.
  • Mueller H, Wildum S, Luangsay S, et al. A novel orally available small molecule that inhibits hepatitis B virus expression. J Hepatol. 2018;68:412–420.
  • Cuconati A, Lee AH, Rijnbrand CA, et al. Therapeutic compositions and methods for treating hepatitis B by administering a lipid nanoparticle formulation comprising siRNAs targeting the hepatitis B genome and an interferon. WO2018232330A1. 2018.
  • Wu ZX, Chen FS, Zhou XL, et al. Tenofovir and telbivudine combination therapy rapidly decreases viral loads in immune-tolerant chronic hepatitis B patients awaiting assisted reproduction: an open-label, randomized, controlled study. Eur J Gastroenterol Hepatol. 2019;31:832–835.
  • Cheng J, Han Y, Jiang JD. Establishment of drug-resistant HBV small-animal models by hydrodynamic injection. Acta Pharm Sin B. 2014;4:270–276.
  • Okada M, Enomoto M, Kawada N, et al. Effects of antiviral therapy in patients with chronic hepatitis B and cirrhosis. Expert Rev Gastroenterol Hepatol. 2017;11:1095–1104.
  • Zoulim F, Durantel D. Antiviral therapies and prospects for a cure of chronic hepatitis B. Cold Spring Harbor Perspect Med. 2015;5:a021501.
  • Li X, Zhang L, Tian Y, et al. Novel HIV-1 non-nucleoside reverse transcriptase inhibitors: a patent review (2011-2014). Expert Opin Ther Pat. 2014;24:1199–1227.
  • Zhan P, Liu X. Novel HIV-1 non-nucleoside reverse transcriptase inhibitors: a patent review (2005-2010). Expert Opin Ther Pat. 2011;21:717–796.
  • Dou D, Mandadapu SR, Alliston KR, et al. Design and synthesis of inhibitors of noroviruses by scaffold hopping. Bioorg Med Chem. 2011;19:5749–5755.
  • Klug DM. Hit-to-lead optimization of small molecules for neglected tropical disease therapeutics. 2018.
  • Sun J, Groppi VE, Gui H, et al. High-throughput screening for drugs that modulate intermediate filament proteins. Methods Enzymol. 2016;568:163–185.
  • Zhou T, Block T, Liu F, et al. HBsAg mRNA degradation induced by a dihydroquinolizinone compound depends on the HBV posttranscriptional regulatory element. Antiviral Res. 2018;149:191–201.
  • Chidley C, Haruki H, Pedersen MG, et al. A yeast-based screen reveals that sulfasalazine inhibits tetrahydrobiopterin biosynthesis. Nat Chem Biol. 2011;7:375–383.
  • Gale M, Yan Q. High-throughput screening to identify inhibitors of lysine demethylases. Epigenomics. 2015;7:57–65.
  • Heifetz A, Southey M, Morao I, et al. Computational Methods Used in Hit-to-Lead and Lead Optimization Stages of Structure-Based Drug Discovery. Methods Mol Biol. 2018;1705:375–394.
  • Deprez-Poulain R, Deprez B. Facts, figures and trends in lead generation. Curr Top Med Chem. 2004;4:569–580.
  • Han X, Jiang M, Yang S. Novel 2-oxo-6,7-dihydrobenzo[a]quinolizine-3-carboxylic acid derivatives for the treatment and prophylaxis of hepatitis b virus infection. WO2016128335A1. 2016.
  • Fu J, Jin X, Lee P, et al. Preparation of polycyclic pyridone compounds as antivirals. WO2018047109A1. 2018.
  • Javanbakht H, Najera I, Wildum S, et al. Preparation of dihydrobenzoquinolizine carboxylic acid derivatives for use as HBsAg and HBV capsid assembly inhibitors. WO2017108630A1. 2017.
  • Chen Y. Pyridine derivatives as novel therapeutic agents for the treatment of HBV infection and their preparation. WO2018022282A1. 2018.
  • Chen L, Zhai P, Shao Q, et al. Preparation of isoquinolinone compounds useful as antiviral drugs. WO2018019297A1. 2018.
  • Fu J. 8,9-Fused 2-oxo-6,7-dihydropyridoisoquinoline compounds as antivirals and their preparation. WO2017216686A1. 2017.
  • Fu J, Jin X, Lee P, et al. Preparation of pentacyclic pyridone compounds as antivirals. WO2017216685A1. 2017.
  • Cheng Z, Han X, Liang C, et al. Preparation of novel tricyclic 4-pyridone-3-carboxylic acid derivatives for the treatment and prophylaxis of hepatitis B virus infection. WO2017013046A1. 2017.
  • Aktoudianakis E, Canales E, Chin E, et al. Preparation of pyridophthalazine compounds for the treatment of hepatitis b virus infection. WO2017205115A1. 2017.
  • Cheng Z, Liang C, Yang S, et al. Preparation of 6,7-dihydropyrido[2,1-a]phthalazin-2-ones for the treatment and prophylaxis of hepatitis B virus infection. WO 2017017043 A1. 2017.
  • Brown N, Jacoby E. On scaffolds and hopping in medicinal chemistry. Mini-Rev Med Chem. 2006;6:1217–1229.
  • BoehmH-J, Flohr A, Stahl M. Scaffold hopping. Drug Discov Today. 2004;1:217–224.
  • Sun H, Tawa G, Wallqvist A. Classification of scaffold-hopping approaches. Drug Discov Today. 2012;17:310–324.
  • Mauser H, Guba W. Recent developments in de novo design and scaffold hopping. Curr Opin Drug Discovery Dev. 2008;11:365–374.
  • Schneider G, Schneider P, Renner S. Scaffold-hopping: how far can you jump? QSAR Comb Sci. 2006;25:1162–1171.
  • Langdon SR, Ertl P, Brown N. Bioisosteric Replacement and Scaffold Hopping in Lead Generation and Optimization. Mol Inform. 2010;29:366–385.
  • Moon S, Masada K, Nozaki K. Reversible Polymer-Chain Modification: ring-Opening and Closing of Polylactone. J Am Chem Soc. 2019;141:10938–10942.
  • Ritchie TJ, Macdonald SJF. Heterocyclic replacements for benzene: maximising ADME benefits by considering individual ring isomers. Eur J Med Chem. 2016;124:1057–1068.
  • Fabian L, Martini MF, Sarduy ES, et al. Evaluation of quinoxaline compounds as ligands of a site adjacent to S2 (AS2) of cruzain. Bioorg Med Chem Lett. 2019;29:2197–2202.
  • Meanwell NA. Synopsis of Some Recent Tactical Application of Bioisosteres in Drug Design. J Med Chem. 2011;54:2529–2591.
  • Nijampatnam B, Liotta DC. Recent advances in the development of HBV capsid assembly modulators. Curr Opin Chem Biol. 2019;50:73–79.
  • Rammelt C, Bilen B, Zavolan M, et al. PAPD5, a noncanonical poly(A) polymerase with an unusual RNA-binding motif. RNA. 2011;17:1737–1746.
  • Zhang BY, Chai DP, Wu YH, et al. Potential drug targets against hepatitis B virus based on both virus and host factors. Curr Drug Targets. 2019;20:1636–1651.
  • Vyas VK, Ghate M, Patel K, et al. Homology modeling, binding site identification and docking study of human angiotensin II type I (Ang II-AT1) receptor. Biomed Pharmacother. 2015;74:42–48.
  • Wispelaere M, Du G, Donovan KA, et al. Small molecule degraders of the hepatitis C virus protease reduce susceptibility to resistance mutations. Nat Commun. 2019;10:3468.
  • Chan AH, Lee WG, Spasov KA, et al. Covalent inhibitors for eradication of drug-resistant HIV-1 reverse transcriptase: from design to protein crystallography. Proc Natl Acad Sci USA. 2017;114:9725–9730.
  • Windsor IW, Palte MJ, Lukesh JC 3rd, et al. Sub-picomolar inhibition of HIV-1 protease with a boronic acid. J Am Chem Soc. 2018;140:14015–14018.

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