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

C536S028200, C514S043000

Reexamination Certificate

active

07858774

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), Vorbruggen et al.
patent: 3891623 (1975-06-01), Vorbruggen et al.
patent: 4082911 (1978-04-01), Vorbruggen
patent: 4209613 (1980-06-01), Vorbruggen
patent: 6642206 (2003-11-01), Ramasamy et al.
patent: 6887855 (2005-05-01), Ionescu et al.
patent: 6943249 (2005-09-01), Ionescu et al.
patent: 7038038 (2006-05-01), Ionescu et al.
patent: 7078518 (2006-07-01), Ionescu et al.
patent: 114716 (1964-11-01), None
patent: 116297 (1965-04-01), None
patent: 1922702 (1969-11-01), None
patent: 2012888 (1971-09-01), None
patent: 2123632 (1972-09-01), None
patent: 1227691 (1971-04-01), None
Niedballa et al. J. Org. Chem. vol. 39, No. 25, 1974.
Winkley et al. J. Org. Chem. 35(2), pp. 491-495, 1970.
Vorbruggen et al. Chem. Ber. 114, 1234-1255 (1981).
Vorbruggen et al. Chem. Ber. 114, 1279-1286 (1981).
Ault, Techniques and Experiments for Organic Chemistry, Edition 6, University Science Books, 1998, pp. 59-60.
Gaubert et al. Nucleosides, Nucleotides, & Nucleic Acids, 20(4-7), 837-840 (2001).
Beisler et al.,J. Carbohydrates Nucleosides Nucleotides, 4(5): 281-99 (1977).
Beisler,J. Med. Chem., 21(2): 204-08 (1978).
Chan, K.K. et al.,J. Pharm. Sci., 68(7): 807-12 (1979).
Gaubert et al.,Nucleosides, Nucleotides&Nucleic Acids, 20(4-7): 837-40 (2001).
Kornblith et al.,J. Clin Oncol., 20(10): 2441-52 (2002).
Niedballa et al.,J. Org. Chem., 39(25): 3672-74 (1974).
Piskala et al.,Collect. Czech. Chem. Commun., 29: 2060-76 (1964).
Piskala et al.,Nucleic Acid Chem., 1: 435-41 (1978).
Piskala et al.,Nucleic Acids Research, Special Pub. No. 1: s17-20 (1975).
Silverman et al.,J. Clin. Oncol., 20(10): 2429-40 (2002).
Vorbruggen et al.,Chem. Ber., 114: 1279-86 (1981).
Vorbruggen et al.inOrganic Reactions, vol. 55, 100 (L.A. Paquette ed., John Wiley & Sons, New York, 2000).
Vorbruggen et al.,Chem. Ber., 114: 1234-55 (1981).
Winkley et al.,J. Org. Chem., 35(2): 491-95 (1970).
Wittenburg et al.,Zeitschrift fur Chemie, 4: 303-04 (1964).
Zaitseva et al.,Bioorg. &Med. Chem. Lett., 5(24): 2999-3002 (1995).
International Search Report for WO2004/82618, dated Sep. 21, 2004.
Office Action in U.S. Appl. No. 10/390,526, mailed Dec. 3, 2003.
Office Action in U.S. Appl. No. 10/390,526, mailed Oct. 21, 2004.
Office Action in U.S. Appl. No. 10/390,526, mailed Apr. 6, 2005.
Notice of Allowability in U.S. Appl. No. 10/390,526, mailed Dec. 1, 2005.
Office Action in U.S. Appl. No. 11/381,275, mailed Mar. 8, 2007.
Office Action in U.S. Appl. No. 11/381,275, mailed Dec. 18, 2007.
Office Action in U.S. Appl. No. 10/390,578, mailed Jul. 1, 2004.
Notice of Allowability in U.S. Appl. No. 10/390,578, mailed Dec. 29, 2004.
Notice of Allowability in U.S. Appl. No. 11/052,615, mailed Mar. 9, 2006.
Office Action in U.S. Appl. No. 11/458,365, mailed Mar. 12, 2007.
Office Action in U.S. Appl. No. 11/458,365, mailed Feb. 27, 2008.
Office Action in U.S. Appl. No. 11/458,365, mailed Nov. 28, 2008.
Office Action in U.S. Appl. No. 11/458,365, mailed Aug. 4, 2009.
Notice of Allowability in U.S. Appl. No. 11/458,365, mailed Jan. 26, 2010.
Notice of Allowability in U.S. Appl. No. 10/390,530, mailed May 13, 2005.
Office Action in U.S. Appl. No. 11/198,550, mailed Aug. 1, 2007.
Office Action in U.S. Appl. No. 11/198,550, mailed May 12, 2008.
Office Action in U.S. Appl. No. 11/198,550, mailed Oct. 2, 2008.
Notice of Allowability in U.S. Appl. No. 11/198,550, mailed Feb. 24, 2009.
Notice of Allowability in U.S. Appl. No. 11/198,550, mailed Jul. 31, 2009.
Notice of Allowability in U.S. Appl. No. 11/198,550, mailed Dec. 2, 2009.

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-4202156

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