Pyridinium trifluoroacetate/N-methylimidazole as an efficient activator for oligonucleotide synthesis via the phosphoramidite method

Organic Process Research and Development

Volumn 4, Issue 3, 2000, Pages 182-189

  Eleuteri, Alessandra ^a   Capaldi, Daniel C ^a   Krotz, Achim H ^a   Cole, Douglas L ^a   Ravikumar, Vasulinga T ^a  

^a ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034394330     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op9900378     Document Type: Article

References (57)

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9. Several oligonucleotide phosphorothioates are in various phases of human clinical trials, e.g., ISIS 2922 has successfully completed Phase III trials, an NDA was submitted and approved, making it the first antisense drug to reach the market, ISIS 2302, ISIS 3521, and ISIS 5132 are in Phase II stages, and several are in Phase I trials. In all, about 20 antisense drugs are being evaluated in the clinic.
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29. (b) Claesen. C.; Tesser, G. I.; Dreef, C. E.; Marugg, J. E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1984, 25, 1307-1310. Chlorotrimethylsilane: Dabkowski, W.; Tworowska, I.; Michalski, J.; Cramer, F. J. Chem. Soc., Chem. Commun. 1997, 877-878. 4,5-Dicyanoimidazole: Vargeese, C.; Carter, J.; Yegge, J.; Krivjansky, S.; Settle, A.; Kropp, E.; Peterson, K.; Pieken, W. Nucleic Acids Res. 1998, 26. 1046-1050. Benzimidazolium triflate: Hayakawa, Y.; Kataoka, M.; Noyori, R. J. Org. Chem. 1996, 61, 7996-7997. Imidazolium triflate: (a) Kataoka, M.; Heidenhain, S.; Hayakawa, Y. Nucleic Acids Symp. Series No 37, 1997, 21-22.
30. (b) Claesen. C.; Tesser, G. I.; Dreef, C. E.; Marugg, J. E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1984, 25, 1307-1310. Chlorotrimethylsilane: Dabkowski, W.; Tworowska, I.; Michalski, J.; Cramer, F. J. Chem. Soc., Chem. Commun. 1997, 877-878. 4,5-Dicyanoimidazole: Vargeese, C.; Carter, J.; Yegge, J.; Krivjansky, S.; Settle, A.; Kropp, E.; Peterson, K.; Pieken, W. Nucleic Acids Res. 1998, 26. 1046-1050. Benzimidazolium triflate: Hayakawa, Y.; Kataoka, M.; Noyori, R. J. Org. Chem. 1996, 61, 7996-7997. Imidazolium triflate: (a) Kataoka, M.; Heidenhain, S.; Hayakawa, Y. Nucleic Acids Symp. Series No 37, 1997, 21-22.
31. (b) Claesen. C.; Tesser, G. I.; Dreef, C. E.; Marugg, J. E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1984, 25, 1307-1310. Chlorotrimethylsilane: Dabkowski, W.; Tworowska, I.; Michalski, J.; Cramer, F. J. Chem. Soc., Chem. Commun. 1997, 877-878. 4,5-Dicyanoimidazole: Vargeese, C.; Carter, J.; Yegge, J.; Krivjansky, S.; Settle, A.; Kropp, E.; Peterson, K.; Pieken, W. Nucleic Acids Res. 1998, 26. 1046-1050. Benzimidazolium triflate: Hayakawa, Y.; Kataoka, M.; Noyori, R. J. Org. Chem. 1996, 61, 7996-7997. Imidazolium triflate: (a) Kataoka, M.; Heidenhain, S.; Hayakawa, Y. Nucleic Acids Symp. Series No 37, 1997, 21-22.
32. (b) Hayakawa, Y.; Kataoka, M. J. Am. Chem. Soc. 1998, 120, 12395-12401. Pyridinium hydrochloride/imidazole: Gryaznov, S. M.; Letsinger, R. L. Nucleic Acids Res. 1992, 20, 1879-1882. Pyridinium tetrafluoroborate and N-methylimidazolium trifluroborate: Brill, W. K. D.; Nielsen, J.; Caruthers, M. H. J. Am. Chem. Soc. 1991, 113, 3972-3980. N-methylanilinium trichloroacetate: Fourrey, J.-L.; Varenne, J.; Fontaine, C.; Guittet, E.; Yang. Z. W. Tetrahedron Lett. 1987, 28, 1769-1772.
33. (b) Hayakawa, Y.; Kataoka, M. J. Am. Chem. Soc. 1998, 120, 12395-12401. Pyridinium hydrochloride/imidazole: Gryaznov, S. M.; Letsinger, R. L. Nucleic Acids Res. 1992, 20, 1879-1882. Pyridinium tetrafluoroborate and N-methylimidazolium trifluroborate: Brill, W. K. D.; Nielsen, J.; Caruthers, M. H. J. Am. Chem. Soc. 1991, 113, 3972-3980. N-methylanilinium trichloroacetate: Fourrey, J.-L.; Varenne, J.; Fontaine, C.; Guittet, E.; Yang. Z. W. Tetrahedron Lett. 1987, 28, 1769-1772.
34. (b) Hayakawa, Y.; Kataoka, M. J. Am. Chem. Soc. 1998, 120, 12395-12401. Pyridinium hydrochloride/imidazole: Gryaznov, S. M.; Letsinger, R. L. Nucleic Acids Res. 1992, 20, 1879-1882. Pyridinium tetrafluoroborate and N-methylimidazolium trifluroborate: Brill, W. K. D.; Nielsen, J.; Caruthers, M. H. J. Am. Chem. Soc. 1991, 113, 3972-3980. N-methylanilinium trichloroacetate: Fourrey, J.-L.; Varenne, J.; Fontaine, C.; Guittet, E.; Yang. Z. W. Tetrahedron Lett. 1987, 28, 1769-1772.
35. (b) Hayakawa, Y.; Kataoka, M. J. Am. Chem. Soc. 1998, 120, 12395-12401. Pyridinium hydrochloride/imidazole: Gryaznov, S. M.; Letsinger, R. L. Nucleic Acids Res. 1992, 20, 1879-1882. Pyridinium tetrafluoroborate and N-methylimidazolium trifluroborate: Brill, W. K. D.; Nielsen, J.; Caruthers, M. H. J. Am. Chem. Soc. 1991, 113, 3972-3980. N-methylanilinium trichloroacetate: Fourrey, J.-L.; Varenne, J.; Fontaine, C.; Guittet, E.; Yang. Z. W. Tetrahedron Lett. 1987, 28, 1769-1772.
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57. Cost of the new activator is <$75/kg, whereas 1H-tetrazole is ∼$950/kg at 100 kg scale.