Synthesis of 5-azacytidine

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C536S124000, C536S028500, C536S028100, C536S023100, C536S024310, C536S024330, C536S022100, C514S049000, C514S085000, C514S269000, C424S045000, C424S450000

Reexamination Certificate

active

07038038

ABSTRACT:
The present invention provides a method for the preparation of 5-azacytidine, wherein 5-azacytidine is represented by the structure:The method involves the silylation of 5-azacytosine, followed by the coupling of silylated 5-azacytosine to a protected β-D-ribofuranose derivative. The coupling reaction is catalyzed by trimethylsilyl trifluoromethanesulfonate (TMS-Triflate).

REFERENCES:
patent: 3350388 (1967-10-01), Sorm et al.
patent: 3817980 (1974-06-01), Vorbrüggen et al.
patent: 3891623 (1975-06-01), Vorbrüggen et al.
patent: 4082911 (1978-04-01), Vorbrüggen
patent: 4209613 (1980-06-01), Vorbrüggen
patent: 6642206 (2003-11-01), Ramasamy et al.
patent: 1922702 (1971-04-01), None
patent: 2012888 (1971-09-01), None
patent: 1227691 (1971-04-01), None
Winkley et al. “Direct glycosylation of 1,3,5-triazinones.” J . Org. Chem. 35(2), 491-95, 1970.
Vorbruggen et al. “Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts.” Chem. Ber. 114, 1234-55, 1981.
Beisler, Journal of Medicinal Chemistry, 21(2):204 (1978).
Niedballa & Vorbrüggen, Journal of Organic Chemistry, 39(25):3672 (1974).
Kornblith et al., J. Clin Oncol. 20:2441 (2002).
Piskala & Sorm, Collect. Czech. Chem. Commun. 29:2060 (1964).
Piskala & Sorm, Nucleic Acid Chemistry 1: 435 (1978).
Piskala & Sorm, Nucleic Acids Research, Special Publication No. 1: s17 (1975).
Silverman et al., J. Clin Oncol. 20: 2429 (2002).
Vorbrüggen et al, Chem. Ber. 114: 1234 (1981).
Vorbrüggen & Bennua, Chem Ber. 114: 1279 (1981).
Vorbrüggen & Ruh-Pohlenz in Organic Reactions, vol. 55, p. 100 (L.A. Paquette Ed., John Wiley & Sons, New York, 2000).
Winkley & Robins, Journal of Organic Chemistry, 35(2):491 (1970).
Wittenburg, Z. Chem. 4:303 (1964).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Synthesis of 5-azacytidine does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of 5-azacytidine, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of 5-azacytidine will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3614785

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.