Erratum: Discovery of 2-Pyridinone Aminals: A Prodrug Strategy to Advance a Second Generation of HIV-1 Integrase Strand Transfer Inhibitors (Journal of Medicinal Chemistry (2015) 58 (8154-8165) DOI: 10.1021/acs.jmedchem.5b01037);Discovery of 2-Pyridinone Aminals: A Prodrug Strategy to Advance a Second Generation of HIV-1 Integrase Strand Transfer Inhibitors

Journal of Medicinal Chemistry

Volumn 58, Issue 20, 2015, Pages 8154-8165

  Raheem, Izzat T ^a   Walji, Abbas M ^a   Klein, Daniel ^a   Sanders, John M ^a   Powell, David A ^a,b   Abeywickrema, Pravien ^a   Barbe, Guillaume ^b   Bennet, Amrith ^a   Clas, Sophie Dorothee ^c   Dubost, David ^a   Embrey, Mark ^a   Grobler, Jay ^a   Hafey, Michael J ^a   Hartingh, Timothy J ^a   Hazuda, Daria J ^a   Miller, Michael D ^a   Moore, Keith P ^a   Pajkovic, Natasa ^a   Patel, Sangita ^a   Rada, Vanessa ^a   Rearden, Paul ^a   Schreier, John D ^a   Sisko, John ^a   Steele, Thomas G ^a   Truchon, Jean François ^b   Wai, John ^a   Xu, Min ^a   Coleman, Paul J ^a   more..

^a MERCK RESEARCH LABORATORIES   (United States)

^b MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^c PharmaSolv Consulting   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRIDINONE AMINAL DERIVATIVE; INTEGRASE INHIBITOR; MK 0536; PRODRUG; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG; INTEGRASE; P31 INTEGRASE PROTEIN, HUMAN IMMUNODEFICIENCY VIRUS 1;

ANTIVIRAL ACTIVITY; ARTICLE; DOG; DRUG ABSORPTION; DRUG DOSE INCREASE; DRUG ISOLATION; DRUG SYNTHESIS; METAL BINDING; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION; ANIMAL; AREA UNDER THE CURVE; CHEMICAL STRUCTURE; DOSE RESPONSE; DRUG DESIGN; DRUG EFFECTS; ENZYMOLOGY; GENETICS; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; METABOLISM; RAT; SYNTHESIS;

ANIMALS; AREA UNDER CURVE; DOGS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HIV-1; HUMANS; MODELS, MOLECULAR; PRODRUGS; PYRIDONES; RATS;

EID: 84945434626     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01957     Document Type: Erratum

References (35)

1. Rowley, M. The Discovery of Raltegravir, an Integrase Inhibitor for the Treatment of HIV Infection Prog. Med. Chem. 2008, 46, 1-28 10.1016/S0079-6468(07)00001-X
2. Evering, T. H.; Markowitz, M. Raltegravir (MK-0518): An Integrase Inhibitor for the Treatment of HIV-1 Drugs Today 2007, 43, 865-877 10.1358/dot.2007.43.12.1146063
3. Dayam, R. G. R.; Al-Mawsawi, L. Q.; Neamati, N. HIV-1 Integrase Inhibitors: 2005-2006 Update Med. Res. Rev. 2008, 28, 118-154 10.1002/med.20116
4. Karmon, S. L.; Markowitz, M. Next-generation Integrase Inhibitors: Where to After Raltegravir? Drugs 2013, 73, 213-228 10.1007/s40265-013-0015-5
5. Croxtall, J. D.; Scott, L. J. Raltegravir: In Treatment-naive Patients with HIV-1 Infection Drugs 2010, 70, 631-642 10.2165/11204590-000000000-00000
6. Métifiot, M.; Marchand, C.; Pommier, Y. HIV Integrase Inhibitors: 20-year Landmark and Challenges Adv. Pharmacol. 2013, 67, 75-105 10.1016/B978-0-12-405880-4.00003-2
7. Di Santo, R. Inhibiting the HIV Integration Process: Past, Present, and the Future J. Med. Chem. 2014, 57, 539-566 10.1021/jm400674a
8. Klibanov, O. M. Elvitegravir, an Oral HIV Integrase Inhibitor, for the Potential Treatment of HIV Infection Curr. Opin. Investig. Drugs 2009, 10, 190-200
9. Reviriego, C. Elvitegravir for the Treatment of HIV Infection Drugs Today 2014, 50, 209-217 10.1358/dot.2014.050.03.2122120
10. Katlama, C.; Murphy, R. Dolutegravir for the Treatment of HIV Expert Opin. Invest. Drugs 2012, 21, 523-530 10.1517/13543784.2012.661713
11. Bar-Magen, T.; Sloan, R. D.; Donahue, D. A.; Kuhl, B. D.; Zabeida, A.; Xu, H.; Oliveira, M.; Hazuda, D. J.; Wainberg, M. A. Identification of Novel Mutations Responsible for Resistance to MK-2048, a Second-generation HIV-1 Integrase Inhibitor J. Virol. 2010, 84, 9210-9216 10.1128/JVI.01164-10
12. Wiscount, C. M.; Williams, P. D.; Tran, L. O.; Embrey, M. W.; Fisher, T. E.; Sherman, V.; Homnick, C. F.; Staas, D. D.; Lyle, T. A.; Wai, J. S.; Vacca, J. P.; Wang, Z.; Felock, P. J.; Stillmock, K. A.; Witmer, M. V.; Miller, M. D.; Hazuda, D. J.; Day, A. M.; Gabryelski, L. J.; Ecto, L. T.; Schleif, W. A.; DiStefano, D. J.; Kochansky, C. J.; Anari, M. R. 10-Hydroxy-7,8-dihydropyrazino[1′,2′:1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-diones: Potent, Orally Bioavailable HIV-1 Integrase Strand-transfer Inhibitors with Activity Against Integrase Mutants Bioorg. Med. Chem. Lett. 2008, 18, 4581-4583 10.1016/j.bmcl.2008.07.037
13. Quashie, P. K.; Sloan, R. D.; Wainberg, M. A. Novel Therapeutic Strategies Targeting HIV Integrase BMC Med. 2012, 10, 34 10.1186/1741-7015-10-34
14. Vacca, J.; Fisher, T.; Embrey, M.; Hazuda, D.; Miller, M.; Felock, P.; Witmer, M.; Gabryelski, L. J.; Lyle, T. A. Discovery of MK-2048: Subtle Changes Confer Unique Resistance Properties to a Series of Tricyclic Hydroxypyrrole Integrase Strand Transfer Inhibitors. Presented at the 4th IAS Conference, Sydney, Australia, 2007. Talk WEPEA088.
15. Wai, J.; Fisher, T.; Embrey, M.; Egbertson, M.; Vacca, J.; Hazuda, D.; Miller, M.; Witmer, M.; Gabryelski, L.; Lyle, T. Next Generation of Inhibitors of HIV-1 Integrase Strand Transfer Inhibitor: Structural Diversity and Resistance Profiles. Presented at the CROI, Los Angeles, CA, 2007. Talk #87.
16. Métifiot, M.; Johnson, B.; Smith, S.; Zhao, X. Z.; Marchand, C.; Burke, T.; Hughes, S.; Pommier, Y. MK-0536 Inhibits HIV-1 Integrases Resistant to Raltegravir Antimicrob. Agents Chemother. 2011, 55, 5127-5133 10.1128/AAC.05288-11
17. Egbertson, M. S.; Wai, J. S.; Cameron, M.; Hoerrner, R. S. Discovery of MK-0536: A Potential Second-Generation HIV-1 Integrase Strand Transfer Inhibitor with a High Genetic Barrier to Mutation. In Antiviral Drugs: From Basic Discovery through Clinical Trials; Kazmierski, W. M., Ed.; John Wiley & Sons, Inc.: New York, 2011; pp 163-180.
18. Tang, H.; Hussain, A.; Leal, M.; Mayersohn, M.; Fluhler, E. Drug Metab. Dispos. 2007, 35, 1886-1893 10.1124/dmd.107.016188
19. Hare, S.; Vos, A. M.; Clayton, R. F.; Thuring, J. W.; Cummings, M. D.; Cherepanov, P. Molecular Mechanisms of Retroviral Integrase Inhibition and the Evolution of Viral Resistance Proc. Natl. Acad. Sci. U. S. A. 2010, 107, 20057-20062 10.1073/pnas.1010246107
20. Hare, S.; Gupta, S. S.; Valkov, E.; Engelman, A.; Cherepanov, P. Retroviral Intasome Assembly and Inhibition of DNA Strand Transfer Nature 2010, 464, 232-236 10.1038/nature08784
21. Hare, S.; Smith, S. J.; Métifiot, M.; Jaxa-Chamiec, A.; Pommier, Y.; Hughes, S. H.; Cherepanov, P. Structural and Functional Analyses of the Second-generation Integrase Strand Transfer Inhibitor Dolutegravir (S/GSK1349572) Mol. Pharmacol. 2011, 80, 565-572 10.1124/mol.111.073189
22. Métifiot, M.; Maddali, K.; Johnson, B. C.; Hare, S.; Smith, S. J.; Zhao, X. Z.; Marchand, C.; Burke, T. R.; Hughes, S. H.; Cherepanov, P.; Pommier, Y. Activities, Crystal Structures, and Molecular Dynamics of Dihydro-1H-isoindole Derivatives, Inhibitors of HIV-1 Integrase ACS Chem. Biol. 2013, 8, 209-217 10.1021/cb300471n
23. Desimmie, B. A.; Demeulemeester, J.; Suchaud, V.; Taltynov, O.; Billamboz, M.; Lion, C.; Bailly, F.; Strelkov, S. V.; Debyser, Z.; Cotelle, P.; Christ, F. 2-Hydroxyisoquinoline-1,3(2H,4H)-diones (HIDs), Novel Inhibitors of HIV Integrase with a High Barrier to Resistance ACS Chem. Biol. 2013, 8, 1187-1194 10.1021/cb4000426
24. SZYBKI, version 1.8.0.1; OpenEye Scientific Software, Inc.: Santa Fe, NM, 2013; www.eyesopen.com.
25. Alorati, A. D.; Bio, M. M.; Brands, K. M. J.; Cleator, E.; Davies, A. J.; Wilson, R. D.; Wise, C. S. A Practical and Scaleable Synthesis of 1R,5S-Bicyclo[3.1.0]hexan-2-one: The Development of a Catalytic Lithium 2,2,6,6-Tetramethylpiperidide (LTMP) Mediated Intramolecular Cyclopropanation of (R)-1,2-Epoxyhex-5-ene Org. Process Res. Dev. 2007, 11, 637-641 10.1021/op700042w
26. Takeda, H.; Honma, M.; Ida, R.; Sawada, T.; Nakada, M. Catalytic Asymmetric Intramolecular Cyclopropanation of 2-diazo-6-heptenoic Acid Esters Synlett 2007, 4, 579-582 10.1055/s-2007-967964
27. Stella, V. J.; Borchardt, R. T.; Hageman, M. J.; Oliyai, R.; Maag, H.; Tilley, J. Prodrugs: Challenges and Rewards Part 1 and Part 2; Springer: New York, 2007.
28. Rautio, J.; Kumpulainen, H.; Heimbach, T.; Oliyai, R.; Oh, D.; Järvinen, T.; Savolainen, J. Prodrugs: Design and Clinical Applications Nat. Rev. Drug Discovery 2008, 7, 255-270 10.1038/nrd2468
29. Clark, D. E. J. Pharm. Sci. 1999, 88, 807-814 10.1021/js9804011
30. Sherer, E. C.; Verras, A.; Madeira, M.; Hagmann, W. K.; Sheridan, R. P.; Roberts, D.; Bleasby, K.; Cornell, W. Mol. Inf. 2012, 31, 231-245 10.1002/minf.201100157
31. Fung, E. N.; Zheng, N.; Arnold, M. E.; Zeng, J. Effective Screening Approach to Select Esterase Inhibitors used for Stabilizing Ester-containing Prodrugs Analyzed by LC-MS/MS Bioanalysis 2010, 2, 733-743 10.4155/bio.10.30
32. Walji, A. M.; Sanchez, R. I.; Clas, S. D.; Nofsinger, R.; de Lera Ruiz, M.; Li, J.; Bennet, A.; John, C.; Bennett, D. J.; Sanders, J. M.; Di Marco, C. N.; Kim, S. H.; Balsells, J.; Ceglia, S. S.; Dang, Q.; Manser, K.; Nissley, B.; Wai, J. S.; Hafey, M.; Wang, J.; Chessen, G.; Templeton, A.; Higgins, J.; Smith, R.; Wu, Y.; Grobler, J.; Coleman, P. J. Discovery of MK-8970: An Acetal Carbonate Prodrug of Raltegravir with Enhanced Colonic Absorption ChemMedChem 2015, 10, 245-252 10.1002/cmdc.201402393
33. Nofsinger, R.; Clas, S.-D.; Sanchez, R. I.; Walji, A. M.; Manser, K.; Nissley, B.; Balsells, J.; Nair, A.; Dang, Q.; Bennett, D. J.; Hafey, M.; Wang, J.; Higgins, J.; Templeton, A.; Coleman, P.; Grobler, J.; Smith, R.; Wu, Y. Design of Prodrugs to Enhance Colonic Absorption by Increasing Lipophilicity and Blocking Ionization Pharmaceuticals 2014, 7, 207-219 10.3390/ph7020207
34. Thomas, J. D.; Sloan, K. B. Overcoming Steric Effects in the Coupling Reaction of Alkoxycarbonyloxymethyl (AOCOM) Halides with Phenols: An Efficient Synthesis of AOCOM Phenolic Prodrugs Tetrahedron Lett. 2007, 48, 109-112 10.1016/j.tetlet.2006.10.160
35. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliand, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The Protein Data Bank Nucleic Acids Res. 2000, 28, 235-242