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Volumn 18, Issue 6, 2014, Pages 717-724

Synthesis of a nucleoside phosphoramidate prodrug inhibitor of HCV NS5B polymerase: Phenylboronate as a transient protecting group

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CHEMISTRY;

EID: 84903196287     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op500042u     Document Type: Article
Times cited : (14)

References (35)
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    • American Association for the Study of Liver Diseases Hepatitis C Guidelines 2012
    • American Association for the Study of Liver Diseases Hepatitis C Guidelines 2012. Gaetano, J. N.; Desai, A. P.; Reau, N. Clin. Med. Insights: Ther. 2012, 4, 39-56
    • (2012) Clin. Med. Insights: Ther. , vol.4 , pp. 39-56
    • Gaetano, J.N.1    Desai, A.P.2    Reau, N.3
  • 6
    • 84903130393 scopus 로고    scopus 로고
    • Accessed 25 November 2013
    • The recent regulatory approval of sofosbuvir has clinically validated this target: http://www.fda.gov/downloads/AdvisoryCommittees/ CommitteesMeetingMaterials/Drugs/AntiviralDrugsAdvisoryCommittee/UCM371877.pdf (Accessed 25 November 2013).
  • 22
    • 84903199828 scopus 로고    scopus 로고
    • Patent Appl. WO2014008236
    • A recent addition to the patent literature demonstrated that using 2 equiv of the uronium reagent HATU with a functionalized phosphoric acid could be used to form this prodrug in 90% yield on 1 g scale. The addition of quinine resulted in a 6.7:1 phosphorus diastereomer mixture. Tran, K.; Eastgate, M. D.; Janey, J.; Chen, K.; Rosso, V. W. Patent Appl. WO2014008236, 2014.
    • (2014)
    • Tran, K.1    Eastgate, M.D.2    Janey, J.3    Chen, K.4    Rosso, V.W.5
  • 31
    • 79960982259 scopus 로고    scopus 로고
    • Beyond preclinical development, the potential for PBA to be a genotoxic impurity in 3 would need to be considered. Methods to control residual arylboronic acids in APIs are discussed in (Accessed 01 April 2014).
    • It remains to be determined whether arylboronic acids in general represent a genotoxic hazard. O'Donovan, M. R.; Mee, C. D.; Fenner, S.; Teasdale, A.; Phillips, D. H. Mutat. Res. 2011, 724, 1-6. Beyond preclinical development, the potential for PBA to be a genotoxic impurity in 3 would need to be considered. Methods to control residual arylboronic acids in APIs are discussed in http://www.andersonsprocesssolutions.com/controlling-residual- arylboronic-acids-as-potential-genotoxic-impurities-in-apis/#-ednref1 (Accessed 01 April 2014).
    • (2011) Mutat. Res. , vol.724 , pp. 1-6
    • O'Donovan, M.R.1    Mee, C.D.2    Fenner, S.3    Teasdale, A.4    Phillips, D.H.5
  • 33
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    • Accessed 07 April 2014
    • Cumulative process mass intensity defined as [total mass of substrates, reagents, and reaction solvents (g)]/[mass of isolated product (g)]. Does not include contributions due to workup, isolation, and purification of products. See PMI calculator: http://www.acs.org/content/acs/en/greenchemistry/industry- business/pharmaceutical.html (Accessed 07 April 2014).
    • PMI Calculator
  • 35
    • 84903177141 scopus 로고    scopus 로고
    • Patent Appl. WO2004052899
    • According to the procedure described in the following patent: Storer, R.; Moussa, A.; Chaudhuri, N.; Waligora, F. Patent Appl. WO2004052899, 2004.
    • (2004)
    • Storer, R.1    Moussa, A.2    Chaudhuri, N.3    Waligora, F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.