Topics in Current Chemistry

, 374:77 | Cite as

Process Chemistry in Antiviral Research

  • Yong-Li Zhong
  • Nobuyoshi Yasuda
  • Hongming Li
  • Mark McLaughlin
  • David Tschaen
Review
Part of the following topical collections:
  1. Antiviral Drug Research

Abstract

This article reviews antiviral therapies that have been approved for human use during the last decade, with a focus on the process chemistry that enabled access to these important drugs. In particular, process chemistry highlights from the practical syntheses of the HCV drugs sofosbuvir (Gilead), grazoprevir (Merck), and elbasvir (Merck), the HIV therapy darunavir (Tibotec) and the influenza treatment peramivir (BioCryst) are presented.

Keywords

Process chemistry Antivirals HCV HIV Influenza Practical synthesis Asymmetric synthesis Sofosbuvir Grazoprevir Elbasvir Darunavir Peramivir 

References

  1. 1.
    Lawrence CM, Menon S, Eilers BJ, Bothner B, Khayat R, Douglas T, Young MJ (2009) J Biol Chem 284:12599CrossRefGoogle Scholar
  2. 2.
    Breitbart M, Rohwer F (2005) Trends Microbiol 13:278CrossRefGoogle Scholar
  3. 3.
    Koonin EV, Senkevich TG, Dolja VV (2006) Biol Direct 1:29CrossRefGoogle Scholar
  4. 4.
    Littler E, Oberg B (2005) Antivir Chem Chemother 16:155CrossRefGoogle Scholar
  5. 5.
    Foser S, Schacher A, Weyer KA, Brugger D, Dietel E, Marti S, Schreitmüller T (2003) Protein Expr Purif 30:78CrossRefGoogle Scholar
  6. 6.
    Gabrielsen B, Phelan MJ, Barthel-Rosa L, See C, Huggins JW, Kefauver DF, Monath TP, Ussery MA, Chmurny GN et al (1992) J Med Chem 35:3231CrossRefGoogle Scholar
  7. 7.
    Zakharieva RD, Galabov AS, Nikolova N (1994) Bioorg Med Chem Lett 4:2831CrossRefGoogle Scholar
  8. 8.
    Luo X-Y, Yin B-L, Ye Z-H (2001) Jingxi Huagong 18:27Google Scholar
  9. 9.
    Yang Z-J, Ding L, Tang Z-G, Duan Z-T (2002) Jingxi Huagong 19:300Google Scholar
  10. 10.
    Cai Y, Xia R, Yang X, Qu G (2009) Zhongguo Yiyao Gongye Zazhi 40:881Google Scholar
  11. 11.
    Liepold B, Jung T, Holig P, Schroeder R, Sever NE, Lafountaine J, Sinclair BD, Gao Y, Wu J, Erickson BK, et al (2011) PCT Int. Appl. WO 2011156578 A1 20111215Google Scholar
  12. 12.
    DeGoey DA, Randolph JT, Liu D, Pratt J, Hutchins C, Donner P, Krueger AC, Matulenko M, Patel S, Motter CE, Nelson L, Keddy R, Tufano M, Caspi DD, Krishnan P, Mistry N, Koev G, Reisch TJ, Mondal R, Pilot-Matias T, Gao Y, Beno DWA, Maring CJ, Molla A, Dumas E, Campbell A, Williams L, Collins C, Wagner R, Kati WM (2014) J Med Chem 57:2047CrossRefGoogle Scholar
  13. 13.
    Ku Y, McDaniel KF, Chen HJ, Shanley JP, Kempf DJ, Grampovnik DJ, Sun Y, Liu D, Gai Y, Or YS et al (2010) PCT Int Appl WO 2010030359 A2 20100318Google Scholar
  14. 14.
    Casarez A, Ji M, Kim CU, Sheng XC, Wu Q (2011) US Pat Appl US 20110135604 A1 20110609Google Scholar
  15. 15.
    Bellani P, Frigerio M, Castoldi P (2001) PCT Int Appl WO 2001021603 A1 20010329Google Scholar
  16. 16.
    Jin L, Xu Z, Jiang H (2004) Faming Zhuanli Shenqing Gongkai Shuomingshu CN 1554647 A 20041215Google Scholar
  17. 17.
    Liu H, Ilevbare GA, Cherniawski BP, Ritchie ET, Taylor LS, Edgar KJ (2014) Carbohydr Polym 100:116CrossRefGoogle Scholar
  18. 18.
    Liu H, Xu L, Hui H, Vivian R, Callebaut C, Murray BP, Hong A, Lee MS, Tsai LK, Chau JK et al (2014) Bioorg Med Chem Lett 24:989CrossRefGoogle Scholar
  19. 19.
    Benedetti F, Berti F, Norbedo S (2002) J Org Chem 67:8635CrossRefGoogle Scholar
  20. 20.
    Adamo I, Benedetti F, Berti F, Campaner P (2006) Org Lett 8:51CrossRefGoogle Scholar
  21. 21.
    Menche D, Arikan F, Li J, Rudolph S (2007) Org Lett 9:267CrossRefGoogle Scholar
  22. 22.
    Flentge CA, Hutchinson DK, Betebenner DA, Degoey DA, Donner PL, Kati WM, Krueger AC, Liu D, Liu Y, Longenecker KL et al (2009) PCT Int Appl WO 2009039134 A1 20090326Google Scholar
  23. 23.
    Shekhar S, Franczyk TS, Barnes DM, Dunn TB, Haight AR, Chan VS (2013) US Pat Appl US 20130224149 A1 20130829Google Scholar
  24. 24.
    Link JO, Taylor JG, Xu L, Mitchell M, Guo H, Liu H, Kato D, Kirschberg T, Sun J, Squires N, Parrish J, Keller T, Yang Z-Y, Yang C, Matles M, Wang Y, Wang K, Cheng G, Tian Y, Mogalian E, Mondou E, Cornpropst M, Perry J, Desai MC (2014) J Med Chem 57:2033CrossRefGoogle Scholar
  25. 25.
    Scott RW, Vitale JP, Matthews KS, Teresk MG, Formella A, Evans JW (2013) US Pat Appl US 20130324740 A1 20131205Google Scholar
  26. 26.
    Scott RW, Vitale JP, Matthews KS, Teresk MG, Formella A, Evans JW (2013) PCT Int Appl WO 2013184702 A1 20131212Google Scholar
  27. 27.
    Scott RW, Wang F, Shi B, Mogalian E (2013) US Pat Appl US 20130324496 A1 20131205Google Scholar
  28. 28.
    Scott RW, Wang F, Shi B, Mogalian E (2013) PCT Int Appl WO 2013184698 A1 20131212Google Scholar
  29. 29.
    Raboisson PJ-MB, De Kock HA, Hu L, Vendeville SMH, Tahri A, Surleraux DLNG, Simmen KA, Nilsson KM, Samuelsson BB, Rosenquist AAK et al (2007) PCT Int Appl WO 2007014926 A1 20070208Google Scholar
  30. 30.
    Horvath A, Depre DPM, Ormerod DJ (2008) PCT Int Appl WO 2008092955 A1 20080807Google Scholar
  31. 31.
    Stokbroekx SCM, Leys C, Swinney KA, Wuyts S, Horvath A (2008) PCT Int Appl WO 2008092954 A2 20080807Google Scholar
  32. 32.
    Raboisson P, de Kock H, Rosenquist A, Nilsson M, Salvador-Oden L, Lin T-I, Roue N, Ivanov V, Wahling H, Wickstrom K et al (2008) Bioorg Med Chem Lett 18:4853CrossRefGoogle Scholar
  33. 33.
    Horvath A, Ormerod DJ, Depre DM, Cerpentier V (2010) PCT Int Appl WO 2010072742 A1 20100701Google Scholar
  34. 34.
    Ormerod, DJ, Depre DPM, Horvath A (2011) PCT Int Appl WO 2011113859 A1 20110922Google Scholar
  35. 35.
    Depre DPM, Ormerod DJ, Horvath A (2013) PCT Int Appl WO 2013041655 A1 20130328Google Scholar
  36. 36.
    Horvath A, Wuyts S, Depre DPM, Couck WLJ, Cuypers JLJ, Harutyunyan S, Binot GFS (2013) PCT Int Appl WO 2013061285 A1 20130502Google Scholar
  37. 37.
    Babine RE, Chen SH, Lamar JE, Snyder NJ, Sun XD, Tebbe MJ, Victor F, Wang QM, Yip YYM, Collado I et al (2002) PCT Int Appl WO 2002018369 A2 20020307Google Scholar
  38. 38.
    Maltais F, Jung YC, Chen M, Tanoury J, Perni RB, Mani N, Laitinen L, Huang H, Liao S, Gao H et al (2009) J Med Chem 52:7993–8001CrossRefGoogle Scholar
  39. 39.
    Tanoury GJ, Chen M, Cochran JE, Looker A, Jurkauskas V (2010) US Pat Appl US 20100063252 A1 2010031Google Scholar
  40. 40.
    Tanoury GJ, Chen M, Cochran JE, Looker A, Jurkauskas V (2010) PCT Int Appl WO 2010126881 A1 20101104Google Scholar
  41. 41.
    Delaney WE, Mo H, Zhong W (2010) US Pat Appl US 20100324059 A1 20101223Google Scholar
  42. 42.
    Ruijter E, Orru R, Znabet A, Polak M, Turner N (2011) PCT Int Appl WO 2011103933 A1 20110901Google Scholar
  43. 43.
    Liu Y, Usui A, Shirakawa S, Maruoka K (2012) Asian J Org Chem 1:180CrossRefGoogle Scholar
  44. 44.
    Mantegazza S, Attolino E, Allegrini P (2013) PCT Int Appl WO 2013131978 A1 20130912Google Scholar
  45. 45.
    Allegrini P, Brunoldi E, Attolino E (2013) PCT Int Appl WO 2013182636 A1 20131212Google Scholar
  46. 46.
    Hoeferl-Prantz K, Felzmann W, Wilhelm T, Benito-Garagorri D (2013) PCT Int Appl WO 2013189980 A1 20131227Google Scholar
  47. 47.
    Hoeferl-Prantz K, Felzmann W (2013) PCT Int Appl WO 2013189978 A1 20131227Google Scholar
  48. 48.
    Iqbal J, Dahanukar VH, Oruganti S, Kandagatla B, Kunhimon SKU, Sagyam RR, Ireni B, Kondepudi VVSM, Muttavarapu MM, Bucchikonda R, et al (2014) PCT Int Appl WO 2014045263 A2 20140327Google Scholar
  49. 49.
    Tanoury GJ, Chen M, Dong Y, Forslund R, Jurkauskas V, Jones AD, Belmont D (2014) Org Process Res Dev 18:1234CrossRefGoogle Scholar
  50. 50.
    Njoroge FG, Chen KX, Shih N-Y, Piwinski JJ (2008) Acc Chem Res 41:50CrossRefGoogle Scholar
  51. 51.
    Morris WJ, Muppalla KK, Cowden C, Ball RG (2013) J Org Chem 78:706CrossRefGoogle Scholar
  52. 52.
    Venkatraman S, Bogen SL, Arasappan A, Bennett F, Chen K, Jao E, Liu Y-T, Lovey R, Hendrata S, Huang Y et al (2006) J Med Chem 49:6074CrossRefGoogle Scholar
  53. 53.
    Wu G, Xie J, Rashatasakhon P, Chen FX, Poirier M, Sprague VM (2007) US Pat Appl US 20070149459 A1 20070628Google Scholar
  54. 54.
    Wong GSK, Lee H-C, Vance JA, Tong W, Iwama T (2008) PCT Int Appl WO 2008079216 A1 20080703Google Scholar
  55. 55.
    Park J, Vater EJ, Dong S, Iwama T, Raghavan RR, Lee H-C, Wong GSK (2008) PCT Int Appl WO 2008082486 A2 20080710Google Scholar
  56. 56.
    Li T, Liang J, Ambrogelly A, Brennan T, Gloor G, Huisman G, Lalonde J, Lekhal A, Mijts B, Muley S et al (2012) J Am Chem Soc 134:6467CrossRefGoogle Scholar
  57. 57.
    Bhalerao DS, Arkala AKR, Madhavi YV, Nagaraju M, Gade SR, Kumar UKS, Bandichhor R, Dahanukar VH (2015) Org Process Res Dev 19:1559CrossRefGoogle Scholar
  58. 58.
    Ludovici DW, De Corte BL, Kukla MJ, Ye H, Ho CY, Lichtenstein MA, Kavash RW, Andries K, de Béthune M-P, Azijin H, Pauwels R, Lewi PJ, Heeres J, Koymans LMH, de Jonge MR, Can Aken KJA, Daeyaert FFD, Das K, Arnold E, Janssen PAJ (2001) Biorg Med Chem Lett 11:2235CrossRefGoogle Scholar
  59. 59.
    Joshi S, Maikap GC, Titirmare S, Chaudhari A, Gurjar MK (2010) Org Process Res Dev 14:657CrossRefGoogle Scholar
  60. 60.
    Merluzzi VJ, Hargrave KD, Labadia M, Grozinger K, Skoog M, Wu JC, Shih C-K, Eckner K, Hattox S, Adams J, Rosehthal AS, Faanes R, Eckner RJ, Koup RA, Sullivan JL (1990) Science 250:1411CrossRefGoogle Scholar
  61. 61.
    Schneider H, Christmann A US Pat (1996) US005569760 A 19961029Google Scholar
  62. 62.
    Boswell RF, Gupton BF, Lo YS US Pat Appl (2004) US20040002603 A1 20040101Google Scholar
  63. 63.
    Janssen PAJ, Lewi PJ, Arnold E, Daeyaert F, de Jonge M, Heeres J, Koymans L, Vinkers M, Guillemont J, Pasquier E, Kukla M, Ludovici D, Fenkel YV, Hughes SH, Medaer B, De Knaep F, Bohets H, De Clerck F, Lampo A, Williams P, Stoffels P (2005) J Med Chem 48:1901CrossRefGoogle Scholar
  64. 64.
    Schils DPR, Willems JJM, Medaer BPAMJ, Pasquier ETJ, Janseen PAJ, Heeres J, Leenders RGG (2004) PTC Int Appl WO 2004016581 A1 20040228Google Scholar
  65. 65.
    Guillemont J, Pasquier E, Palandjian P, Vernier D, Gaurrand S, Lewi PJ, Heeres J, de Jonge MR, Koymans LMH, Daeyaert FFD, Vinkers MH, Arnold E, Das K, Pauwels R, Andries K, de Béthune M-P, Bettens E, Hertogs K, Wigerinck P, Timmerman P, Jansssen PAJ (2005) J Med Chem 48:2072CrossRefGoogle Scholar
  66. 66.
    Stevens PTA, Peeters J, Vandecruys RPG, Stappers AE, Copmans AH (2006) PTC Int Appl WO 2006024668 A1 20060309Google Scholar
  67. 67.
    Judge TM, Phillip G, Morris JK, Lovasz KD, Romines KR, Luke GP, Tulinsky J, Tustin JM, Chrusciel RA, Dolak LA, Mizsak A, Watt W, Morris J, Vander Velde SL, Strohbach JW, Gammill RB (1997) J Am Chem Soc 119:3627CrossRefGoogle Scholar
  68. 68.
    Turner SR, Strohbach JW, Tommasi RA, Arisstoff PA, Johnson PD, Skulnick HI, Dolak LA, Seest EP, Tomich PK, Bohanon MJ, Horng M-M, Lynn JC, Chong K-T, Hinshaw RR, Watenpaugh KD, Janakiraman MN, Thaisrivongs S (1998) J Med Chem 41:3467CrossRefGoogle Scholar
  69. 69.
    Fors KS, Gage JR, Heier RF, Kelly RC, Perraullt WR, Wicnienski N (1998) J Org Chem 63:7348CrossRefGoogle Scholar
  70. 70.
    Lou S, Moquist PN, Schaus SE (2007) J Am Chem Soc 129:15398CrossRefGoogle Scholar
  71. 71.
    Price DA, Gayton S, Selby MD, Ahman J, Haycock-Lewandowski S, Stammen BL, Warren A (2005) Tetrahedron Lett 46:5005CrossRefGoogle Scholar
  72. 72.
    Ahman J, Birch M, Haycock-Lewandowski SJ, Long J, Wilder A (2008) Org Process Res Dev 12:1104CrossRefGoogle Scholar
  73. 73.
    Johns BA, Kawasuji T, Weatherhead JG, Taishi T, Temelkoff DP, Yoshida H, Akiyama T, Taoda Y, Murai H, Kiyama R, Fuji M, Tanimoto N, Jeffrey J, Foster SA, Yoshinaga T, Seki T, Kobayashi M, Sato A, Johnson MN, Garvey EP, Fujiwara T (2013) J Med Chem 56:5901CrossRefGoogle Scholar
  74. 74.
    Yoshida H, Taoda Y, Johns BA (2010) PCT Int Appl WO 2010068253 A1 20100617Google Scholar
  75. 75.
    Johns BA, Duan M, Hakogi T (2010) PCT Int Appl WO2010068262 A1 20100617Google Scholar
  76. 76.
    Sumio Y, Okamoto K, Masui M, Yamada D, Igarashi F (2012) PCT Int Appl WO2012018065 A1 20120209Google Scholar
  77. 77.
    Sato M, Kawakami H, Motomura T, Aramaki H, Matsuda T, Yamashita M, Ito Y, Matsuzaki Y, Yamataka K, Ikeda S, Shinkai H (2009) J. Med. Chem 52:4869CrossRefGoogle Scholar
  78. 78.
    Satoh M, Motomura T, Matsuda T, Kondo K, Ando K, Matsuda K, Miyake S, Uehara H (2005) PTC Int Appl WO 2005113508 A1 20051201Google Scholar
  79. 79.
    Pcion D, Tomasi C, Whitcomb MC, Dowdy ED, Fu W, Macleod P (2014) PTC Int Appl WO 2014022707 A1 20140206Google Scholar
  80. 80.
    Rádl S, Stach J, Piŝa O, Cinibulk J, Havliček J, Zajícová M, Pekárek TJ (2015) Heterocycl Chem. doi: 10.1002/jhet.2477 Google Scholar
  81. 81.
    Summa V, Petrocchi A, Bonelli F, Crescenzi B, Donghi M, Ferrara M, Fiore F, Gardelli C, Gonzalez Paz O, Hazuda DJ, Jones P, Kinzel O, Laufer R, Monteagudo E, Muraglia E, Nizi E, Orvieto F, Pace P, Pescatore G, Scarpelli R, Stillmock K, Witmer MV, Rowley MJ (2008) J Med Chem 51:5843CrossRefGoogle Scholar
  82. 82.
    Pye PJ, Zhong Y-L, Jones GO, Reamer RA, Houk KN, Askin D (2008) Angew Chem Int Ed 47:4134CrossRefGoogle Scholar
  83. 83.
    Humphrey GR, Pye PJ, Zhong Y-L, Angelaud R, Askin D, Belyk KM, Maligres PE, Mancheno DE, Miller RA, Reamer RA, Weissman SA (2011) Org Process Res Dev 15:73CrossRefGoogle Scholar
  84. 84.
    Gulabrao DP, Siddheshwar WK, Shivnath BS, Pankaj SP, Mangesh SD, Ashok TC, Swapnil PS, Golak CM, Mukund KG (2012) Org Process Res Dev 16:1422CrossRefGoogle Scholar
  85. 85.
    Xu L, Liu H, Murray BP, Callebaut C, Lee MS, Hong A, Stickley RG, Tsai LK, Stray KM, Wang Y, Rhodes GR, Desai MC (2010) ACS Med Chem Lett 1:209CrossRefGoogle Scholar
  86. 86.
    Xu L, Liu H, Hong A, Vivian R, Murray BP, Callebaut C, Choi Y-C, Lee MS, Chau J, Tsai LK, Stray KM, Strickley RG, Wang J, Tong L, Swaminathan S, Rhodes GR, Desai MC (2014) Biorg Med Chem Lett 24:995CrossRefGoogle Scholar
  87. 87.
    Polniaszek R, Pfeiffer S, Yu R, Cullen A, Dowdy E, Tran D, Kent K, Zhou Z, Cordeau D, Easton L (2010) PCT Int Appl WO 2010115000 A2 20101007Google Scholar
  88. 88.
    Bisacchi GS, Chao ST, Bachard C, Daris JP, Innaimo S, Jacobs GA, Kocy O, Lapointe P, Martel A, Merchant Z, Slusarchyk WA, Sundeen JE, Young MG, Colonno R, Zahler R (1997) Biorg Med Chem Lett 7:127CrossRefGoogle Scholar
  89. 89.
    Pendri YR, Shi Z, Patel RN, Chan YY, Rijhwani SK, Singh AK, Wang S, Stojanovic M, Polniaszek R, Lewis C, Thottathil J, Chen C-PH, Krishnamurty D, Zhou MX, Vermishetti P, Banerjee A, Kucera DJ, Patel SS, Evans JM, Liang J, Kronenthal DR, Powers GL, Prasad SJ, Bien JT (2012) EU pat Appl EP 2433941A1 20120328Google Scholar
  90. 90.
    Zhou MX, Reiff EA, Vemishetti P, Pendri YR, Singh AK, Prasad SJ, Dhokte UP, Qian X, Mountford P, Hartung KB, Sailes H (2005) US pat Appl US 20050272932 A1 20051208Google Scholar
  91. 91.
    Spadari S, Maga G, Focher F, Ciarrocchi G, Manservigi R, Arcamone F, Capobianco M, Carcuro A, Colonna F, Iotti S, Garbesi A (1992) J Med Chem 35:4214CrossRefGoogle Scholar
  92. 92.
    Chaudhuri NC, Moussa A, Stewart A, Wang J, Storer R (2005) Org Process Res Dev 9:457CrossRefGoogle Scholar
  93. 93.
    Cercus J, Foulkes M, Heinz T, Niederer D, Schmitz B WO2007/104793Google Scholar
  94. 94.
    Laninamivir: Honda T, Kobayashi Y, Masuda T, Yamashita M, Arai M (2002) US pat US 6340702 B1 20020122Google Scholar
  95. 95.
    Nakamura Y, Murakami M, Yamaoka M, Wakayama M, Umeo K (2008) PTC Int Appl WO 2008126943 A2 20081023Google Scholar
  96. 96.
    Dach R, Song JJ, Roschangar F, Samstag W, Senanayake CH (2012) Org Process Res Dev 16:1697–1706CrossRefGoogle Scholar
  97. 97.
    Yasuda N (ed) (2011) The art of process chemistry. Wiley-VCH, WeinheimGoogle Scholar
  98. 98.
    Zhong Y-L, Tucker TJ, Yin JJ (2011) In: Huang XH, Aslanian RG (eds) Case studies in modern drug discovery and development. Wiley-VCH, Weinheim, p 257Google Scholar
  99. 99.
    WHO (2015) HCV epidemic update: July 2015Google Scholar
  100. 100.
    WHO (1999) Wkly Epidemiol Rec 74: 425427Google Scholar
  101. 101.
    Liang TJ, Heller T (2004) Gastroenterology 127:S62CrossRefGoogle Scholar
  102. 102.
    Lavanchy D (2009) Liver Int 29(suppl 1):74CrossRefGoogle Scholar
  103. 103.
    Adachi T, Ago H, Habuka N (2002) Biochem Biophys Acta 39:1601Google Scholar
  104. 104.
    Shepard CW, Alter MJ (2005) Lancet 5:524CrossRefGoogle Scholar
  105. 105.
    Calvaruso V, Mazza M, Almasio PL (2011) Expert Opin Drug Saf 10:429CrossRefGoogle Scholar
  106. 106.
    Gane EJ, Stedman CA, Hyland RH, Ding X, Svarovskaia E, Symonds WT, Hindes RG, Berrey MM (2013) N Engl J Med 368:34CrossRefGoogle Scholar
  107. 107.
    Clark JL, Hollecker L, Mason XJC, Stuyver LJ, Tharnish PM, Lostia S, McBrayer XTR, Schinazi RF, Watanabe KA, Otto MJ, Furman PA, Stec WJ, Patterson SE, Pankiewicz KW (2005) J Med Chem 48:5504 (and references cited therein) CrossRefGoogle Scholar
  108. 108.
    Sofia MJ, Bao D, Chang W, Du J, Nagarathnam D, Rachakonda S, Reddy PG, Ross BS, Wang P, Zhang H-R, Bansal S, Espiritu C, Keilman M, Lam AM, Micolochick Steuer HM, Niu C, Otto MJ, Furman PA (2010) J Med Chem 53:7202 (and references cited therein) CrossRefGoogle Scholar
  109. 109.
    Wang P, Chun B-K, Rachakonda S, Du J, Khan S, Shi J, Stec W, Cleary D, Ross BS, Sofia MJ (2009) J Org Chem 74:6819 (and references cited therein) CrossRefGoogle Scholar
  110. 110.
    Peifer M, Berger R, Shurtleff VW, Conrad JC, MacMillan DWC (2014) J Am Chem Soc 136:5900CrossRefGoogle Scholar
  111. 111.
    Simonovich SP, Van Humbeck JF, MacMillan DWC (2012) Chem Sci 3:58CrossRefGoogle Scholar
  112. 112.
    Nakayama K, Thompson WJ (1990) J Am Chem Soc 112:6936CrossRefGoogle Scholar
  113. 113.
    Wozniak LA, Okruzsek A (2003) Chem Soc Rev 32:158 (and references cited therein) CrossRefGoogle Scholar
  114. 114.
    Oka N, Wada T (2011) Chem Soc Rev 40:5829 (and references cited therein) CrossRefGoogle Scholar
  115. 115.
    Ross BS, Reddy PG, Zhang H-R, Rachakonda S, Sofia MJ (2011) J Org Chem 76:8311 (and references cited therein) CrossRefGoogle Scholar
  116. 116.
    Zeuzem S, Ghalib R, Rajender Reddy K, Pockros PJ, Ari ZB, Zhao Y, Brown DD, Wan S, DiNubile MJ, Nguyen B-Y, Robertson MN, Wahl J, Barr E, Butterton JR (2015) Ann Intern Med 163:1CrossRefGoogle Scholar
  117. 117.
    Dore G, Altice F, Litwin AH, Dalgard O, Gane EJ, Shibolet O, Luetkemeyer A, Nahass R, Peng C-Y, Conway B, Grebely J, Howe AY, Nguyen B-Y, Wahl J, Barr E, Robertson M, Platt HL (2015) C-EDGE CO-STAR: efficacy of grazoprevir and elbasvir in persons who inject drugs (PWID) receiving opioid agonist therapy. AASLD Liver Meeting, San Francisco, abstract 40Google Scholar
  118. 118.
    Harper S, McCauley JA, Rudd MT, Ferrara M, DiFilippo M, Crescenzi B, Koch U, Petrocchi A, Holloway MK, Butcher JW, Romano JJ, Bush KJ, Gilbert KF, McIntyre CJ, Nguyen KT, Nizi E, Carroll SS, Ludmerer SW, Burlein C, DiMuzio JM, Graham DJ, McHale CM, Stahlhut MW, Olsen DB, Monteagudo E, Cianetti S, Giuliano C, Pucci V, Trainor N, Fandozzi CM, Rowley M, Coleman PJ, Vacca JP, Summa V, Liverton NJ (2012) Med Chem Lett 3:332CrossRefGoogle Scholar
  119. 119.
    Yu X, Sun D (2013) Molecules 18:6230 (and references cited therein) CrossRefGoogle Scholar
  120. 120.
    Kuethe JT, Zhong Y-L, Yasuda N, Beutner GL, Linn K, Kim MM, Marcune B, Dreher SD, Humphrey G, Pei T (2013) Org Lett 15:4174CrossRefGoogle Scholar
  121. 121.
    Bassan EM, Baxter CA, Beutner GL, Emerson KM, Fleitz FL, Johnson S, Keen S, Kim MM, Kuethe JT, Leonard WR, Mullens PR, Muzzio DJ, Roberge C, Yasuda N (2012) Org Process Res Dev 16:87 (and references cited therein) CrossRefGoogle Scholar
  122. 122.
    Coburn CA, Meinke PT, Chang W, Fandozzi CM, Graham DJ, Hu B, Huang Q, Kargman S, Kozlowski J, Liu R, McCauley JA, Nomeir AA, Soll RM, Vacca JP, Wang D, Wu H, Zhong B, Olsen DB, Ludmerer SW (2013) Chem Med Chem 8:1930CrossRefGoogle Scholar
  123. 123.
    Li G, Fronczek FR, Antilla JC (2008) J Am Chem Soc 130:12216CrossRefGoogle Scholar
  124. 124.
    Vellalath S, Coric I, List B (2010) Angew Chem Int Ed 49:9749CrossRefGoogle Scholar
  125. 125.
    Li T-Z, Wang X-b, Sha F, Wu X-Y (2013) Tetrahedron 69:7314CrossRefGoogle Scholar
  126. 126.
    Hashimoto T, Nakatsu H, Takiguchi Y, Maruoka K (2013) J Am Chem Soc 135:16010CrossRefGoogle Scholar
  127. 127.
    Honjo T, Phipps RJ, Rauniyar V, Toste FD (2012) Angew Chem Int Ed 51:9684CrossRefGoogle Scholar
  128. 128.
    Mangion I, Chen C-Y, Li H, Maligres P, Chen Y, Christensen M, Cohen R, Jeon I, Klapars A, Krska S, Nguyen H, Reamer RA, Sherry BD, Zavialov I (2014) Org Lett 16:2310CrossRefGoogle Scholar
  129. 129.
    Li H, Chen C-Y, Nguyen H, Cohen R, Maligres P, Yasuda N, Mangion I, Zavialov I, Reibarkh M, Chung JJ (2014) Org Chem 79:8533 and references therein CrossRefGoogle Scholar
  130. 130.
    Li H, Belyk KM, Yin J, Chen Q, Hyde A, Ji Y, Oliver S, Tudge MT, Campeau L-C, Campos KR (2015) J Am Chem Soc 137:13728CrossRefGoogle Scholar
  131. 131.
    UNAIDS/WHO (2014) AIDS epidemic update: July 2014Google Scholar
  132. 132.
    Weiss RA (1993) Science 260:1273CrossRefGoogle Scholar
  133. 133.
    Douek DC, Roederer M, Koup RA (2009) Annu Rev Med 60:471CrossRefGoogle Scholar
  134. 134.
    Surleraux DLNG, Tahri A, Verschueren WG, Pille GME, de Kock HA, Jonckers THM, Peeters A, De Meyer S, Azijn H, Pauwels R, de Bethune M-P, King NM, Prabu-Jeyabalan M, Schiffer CA, Wigerinck PBTP (2005) J Med Chem 48:1813CrossRefGoogle Scholar
  135. 135.
    Liu C, Ng JS, Behling JR, Yen CH, Campbell AL, Fuzail KS, Yonan EE, Mehrotra DV (1997) Org Process Res Dev 1:45CrossRefGoogle Scholar
  136. 136.
    Ghosh AK, Kincaid JF, Cho W, Walters DE, Krishnan K, Hussain KA, Koo Y, Cho H, Rudall C, Holland L, Buthod J (1998) Bio Med Chem Lett 8:687CrossRefGoogle Scholar
  137. 137.
    Ghosh AK, Chen Y (1995) Tetrahedron Lett 36:505CrossRefGoogle Scholar
  138. 138.
    Quaedflieg PJLM, Kesteleyn BRR, Wigerinck PBTP, Goyvaerts NMF, Vijn RJ, Liebregts CSM, Kooistra JHMH, Cusan C (2005) Org Lett 7:5917CrossRefGoogle Scholar
  139. 139.
    Kesteleyn BRR, Surleraux DLNG (2003) PTC Int Appl WO 03022853 A1 20030320Google Scholar
  140. 140.
    Quaedflieg PJLM, Kesteleyn BRR, Vijn RJ, Liebregts CSM, Kooistra JHMH, Lommen FAM (2005) PTC Int Appl WO 2005095410 A1 20051013Google Scholar
  141. 141.
    Yu RH, Polniaszek RP, Becker MW, Cook CM, Yu LHL (2007) Org Process Res Dev 11:972CrossRefGoogle Scholar
  142. 142.
    Canoy WL, Cooley BE, Corona JA, Lovelace TC, Millar A, Weber AM, Xie A, Zhang Y (2008) Org Lett 10:1103CrossRefGoogle Scholar
  143. 143.
    WHO (2015) Influenza epidemic update: December 2015Google Scholar
  144. 144.
    WHO fact sheets: Influrnza (Bird Flu) and Highly Pathogenic Avian Influenza A (H5N1) VirusGoogle Scholar
  145. 145.
    Babu YS, Chand P, Bantia S, Kotian P, Dehghani A, El-Kattan Y, Lin TH, Hutchison TL, Elliott AJ, Parker CD, Ananth SL, Horn LL, Laver GW, Montgomery JA (2000) J Med Chem 43:3482CrossRefGoogle Scholar
  146. 146.
    Chand P, Kotian PL, Dehghani A, El-Kattan Y, Lin T-H, Hutchison TL, Babu YS, Bantia S, Elliot AJ, Montgomery JA (2001) J Med Chem 44:4379CrossRefGoogle Scholar
  147. 147.
    Babu YS, Chand P, Montgomery JA (1999) PTC Int Appl WO 9933781A1 19990708Google Scholar
  148. 148.
    Abdel-Magid AF, Bichsel H-U, Korey DJ, Laufer GG, Lehto EA, Mattei S, Rey M, Schultz TM, Maryanoff C (2001) PTC Int Appl WO 0100571 A1 20010104Google Scholar
  149. 149.
    Zhu Y, Wang Y, Qi T, Liu W (2012) Faming Zhuanli Shenqing Gongkai Shuomingshu CN 102757465 A 20090923Google Scholar

Copyright information

© Springer International Publishing Switzerland 2016

Authors and Affiliations

  1. 1.Department of Process ChemistryMerck and Co., Inc.RahwayUSA

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