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Volumn 6, Issue 17, 2004, Pages 2901-2904

Synthesis of BILN 2061, an HCV NS3 protease inhibitor with proven antiviral effect in humans

Author keywords

[No Author keywords available]

Indexed keywords

BILN 2061; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 4444345444     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0489907     Document Type: Article
Times cited : (101)

References (43)
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    • (b) The Hepatits C Viruses; Hagedorn, C. H., Rice, C. M., Eds.; Springer: Berlin, 2000; Curr. Top. Microbiol. Immunol. 242.
    • Curr. Top. Microbiol. Immunol. , vol.242
  • 23
    • 0142023994 scopus 로고    scopus 로고
    • For reviews on olefin metathesis, see: (a) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (b) Trnka, T. M.; Grubbs, R. H.; Acc. Chem. Res. 2001, 34, 18. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 4592
    • Schrock, R.R.1    Hoveyda, A.H.2
  • 24
    • 0034746687 scopus 로고    scopus 로고
    • For reviews on olefin metathesis, see: (a) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (b) Trnka, T. M.; Grubbs, R. H.; Acc. Chem. Res. 2001, 34, 18. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 18
    • Trnka, T.M.1    Grubbs, R.H.2
  • 25
    • 0142023994 scopus 로고    scopus 로고
    • For reviews on olefin metathesis, see: (a) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592. (b) Trnka, T. M.; Grubbs, R. H.; Acc. Chem. Res. 2001, 34, 18. (c) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3012
    • Fürstner, A.1
  • 30
    • 0000989392 scopus 로고
    • The Perkin Reaction and Related Reactions
    • Adams, R., Bachmann, E. W., Fieser, L. F., Johnson, J. R., Snyder, H. R., Eds.; John Wiley & Sons: New York, Chapter 8, and references therein
    • For a discussion on the Perkin related reactions, see: Johnson, J. R. The Perkin Reaction and Related Reactions. In Organic Reactions; Adams, R., Bachmann, E. W., Fieser, L. F., Johnson, J. R., Snyder, H. R., Eds.; John Wiley & Sons: New York, 1942; Vol, 1, Chapter 8, pp 210-255 and references therein.
    • (1942) Organic Reactions , vol.1 , pp. 210-255
    • Johnson, J.R.1
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    • 4444364622 scopus 로고    scopus 로고
    • note
    • Byproduct 10 was likely formed by reaction of an enolate derived from 8 with acetic anhydride. When acetic anhydride was replaced by bulkier anhydrides (e.g., isobutyric anhydride) to try to minimize the side reaction leading to 10, the rate of the Perkin reaction was considerably decreased and the reaction profile was less clean.
  • 40
    • 4444350158 scopus 로고    scopus 로고
    • Boehringer Ingelheim (Canada) Ltd. U.S. Patent 6,608,027, 2003
    • Alternatively, a fully assembled 4-hydroxy-7-methoxy-2-thiazolylquinoline can be coupled to the macrocyclic substrate as described in: Tsantrisos, Y. S.; Cameron, D,; Faucher, A.-M.; Ghiro, E.; Goudreau, N.; Halmos, T.; Llinàs-Brunet, M. Boehringer Ingelheim (Canada) Ltd. U.S. Patent 6,608,027, 2003; Chem. Abstr. 139:197768.
    • Chem. Abstr. , vol.139 , pp. 197768
    • Tsantrisos, Y.S.1    Cameron, D.2    Faucher, A.-M.3    Ghiro, E.4    Goudreau, N.5    Halmos, T.6    Llinàs-Brunet, M.7
  • 42
    • 4444229758 scopus 로고    scopus 로고
    • Liu, K.-C.; Lu, W.-C.; Lee, L.-C. Taiwan Yaoxue Zazhi 1979, 31, 80; Chem. Abstr. 94:174832.
    • Chem. Abstr. , vol.94 , pp. 174832
  • 43
    • 4444222025 scopus 로고    scopus 로고
    • note
    • N2 reaction of mesylated 4-hydroxyproline by 4-hydroxyquinoline derivatives produces a small amount of elimination byproduct that is difficult to separate from the desired substitution product (data not shown).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.