Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2007-11-06
2007-11-06
Jiang, S. Anna (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S027400, C536S028540
Reexamination Certificate
active
11086545
ABSTRACT:
The present invention is directed to the process for the preparation of 2′-deoxy-2′-halo-β-L-arabinofuranosyl nucleosides, and in particular, 2′-deoxy-2′-fluoro-β-L-arabinofuranosyl thymine (L-FMAU), from L-arabinose, which is commercially available and less expensive than L-ribose or L-xylose, in ten steps. All of the reagents and starting materials are inexpensive and no special equipment is required to carry out the reactions.
REFERENCES:
patent: 5565438 (1996-10-01), Chu et al.
patent: 5567688 (1996-10-01), Chu et al.
patent: 5587362 (1996-12-01), Chu et al.
patent: 5808040 (1998-09-01), Chu et al.
patent: 6512107 (2003-01-01), Chu et al.
patent: 6870048 (2005-03-01), Sznaidman
patent: WO 95/20595 (1995-03-01), None
[R] Wright et al., “Nucleosides. LXIV. Fluoro Sugar Analogs of Arabinosyl- and Xylosylcytosines,” Journal of Medicinal Chemistry, 13, 269-272 (Mar. 1970).
(S) Aldrich Chemical Co., “Handbook of Fine Chemicals and Laboratory Equipment,” Milkwaukee, WI, 2000-2001, only p. 1479 supplied.
Wright et al., “Nucleosides. LXIV. Fluoro Sugar Analogs of Arabinosyl- and Xylosylcytosines,”Journal of Medicinal Chemistry, 13, 269-272 (Mar. 1970).
Albano, E.L., et al., “The synthesis of certain derivatives of 2-fluoro-D-ribose, 2-deoxy-2-fluoro-D-ribose, and 2-doexy-2-fluoro-D-arabinose,”Carbohyd. Res., 19:63-70 (1971).
Albert, M., et al., “A novel direct route to 2-deoxy-2-fluoro-aldoses and their corresponding derivatives,”Tetrahedron, 54:4839-4848 (1998).
Balog, A., et al., “A practical asymmetric synthesis of a pseudomonic acid precursor from D-arabinose or D-xylose,”Synthetic Comm., 26(5):935-944 (1996).
Bols, M., et al., “Preparation of 2,3-epoxyaldonolactones and their conversion into 2-fluoro-2-deoxy-aldonolactones and -sugars,”Acta Chem. Scand., 44(3):252-256 (1990).
Chu, C.K., et al., “Use of 2′-fluoro-5-methyl-β-L-arabinofuranosyluracil as a novel antiviral agents for hepatitis B virus and Epstein-Barr virus,”Antimicrobial Agents Chemother., 39(4):979-981 (Apr. 1995).
Du, J., et al., “A practical synthesis of L-FMAU from L-arabinose,”Nucleosides&Nucleosides, 18(2):187-195 (1999).
Fristad, W.E., et al., “Conversion of alkenes to 1,2-diazides and 1,2-diamines,”J. Org. Chem., 50:3647-3649 (1985).
MA, T., et al., “Structure-activity relationships of 1-(2-deoxy-2-fluoro-β-L-aradinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents,”J. Med. Chem., 39(14):2835-2843 (1996).
Ryan, K.J., et al., “[55] 9-β-L-Ribofuranosyladenine (‘L-adenosine’): configurational inversion within a furanoid ring,”Synthetic Procedures in Nucleic Acid Chemistry, vol. 1 (Interscience Publishers, New York, NY, 1968) pp. 163-167.
Smiatacz, Z., et al., “Configuration and conformation of the products of reaction of 3,4-di-O-Acetyl-2-deoxy-2-nitroso-β-D-arabinopyranosyl chloride with pyrazole,”Carbohydr. Res., 172:171-182 (1988).
Sznaidman, M. L., et al., “New synthesis of L-FMAU from L-arabinose,”Nucleosides, Nucleotides&Nucleic Acids, 21(2), 155-163 (2002).
Vargha, L., et al., “Uber die Substitution von Tosyloxy-Gruppen durch Acetoxy-Gruppen in Polyoxy Verbindungen,”Chem. Ber., 87(9):1351-1356 (1954).
Wright, J.A., et al., “Nucleosides. LX. Fluorocarbohydrates. XXII. Synthesis of 2-deoxy-2-fluoro-D-arabinose and 9-(2-deoxy-2-fluoro-α- and -β-D-arabinofuranosyl)adenines,”J. Org. Chem., 34(9):2632-2636, Sep. 1969.
Wysocki, R.J., et al., “A more expedient approach to the synthesis of anti-HIV-active 2,3-dideoxy-2-fluoro-b-D-threo-pentofuranosyl,”Synthesis, 11:1005-1008 (Nov. 1991).
Bukwang Pharmaceuticals Ind Co., Ltd.
Crane L. E.
Jiang S. Anna
King & Spalding LLP
LandOfFree
Process for the preparation of... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3886213