Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1990-11-29
1993-01-19
Rivers, Diana
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544277, 536 274, 536 2671, C07D47340, C07H 1920
Patent
active
051808242
ABSTRACT:
This invention pertains to novel methods of synthesizing fludarabine, fludarabine phosphate and related nucleoside pharmacologic agents utilizing 6-azido-2-fluoropurine as a novel intermediate.
In particular this invention pertains to a synthesis of fludarabine where the relatively low yield fluorination step is done before the costly coupling step.
REFERENCES:
patent: 4188378 (1980-02-01), Montgomery
patent: 4199574 (1980-04-01), Schaeffer
patent: 4210745 (1980-07-01), Montgomery
patent: 4357324 (1982-11-01), Montgomery et al.
patent: 4609661 (1986-09-01), Verheyden et al.
patent: 4963662 (1990-10-01), Matthes et al.
patent: 4968674 (1990-11-01), Taniyama et al.
Temple et al., "Studies on the Azidoazomethine-Tetrazole Equilibrium, V. 2- and 6-Azidopurines," J. Org. Chem., 1966, 31, 2210-15.
Montgomery et al., "Nucleosides of 2-Fluoroadenine," J. Med. Chem., 1969, 12, 498-504.
Montgomery et a., "The Synthesis of a Metabolically Stable Derivative . . . ," Townsend (ed.), Nucleic Acid Chemistry, pp. 156-160, 1986.
Montgomery et al., "Synthesis of Potential Anticancer Agents, XX, 2-Fluoropurines," JACS, 1960, 82, 463-68.
Eaton et al., "Convenient Synthesis of 2-Fluoroadenine," J. Org. Chem., 1969, 34, 747-48.
Montgomery, "The Chemistry and Biology of Nucleosides of Purines and Ring Analogs," Rideout (ed.), Nucleosides, Nucleotides, and Their Biological Applications, Proc. 5th Intl. Round Table, pp. 19-16, Oct. 20-22, 1982.
Olah et al., "Synthetic Methods and Reactions, 63, Pyridinium . . . ," J. Org. Chem., vol. 44, No. 22, 1979, pp. 3872-3881.
Huang et al., "Analogs of 2'-Deoxyadenosine: Facile Enzymatic Preparation and Growth Inhibitory . . . ," Biochem. Pharm., vol. 30, No. 19, 2663-71, '81.
Carson et al., "Synthesis of 2',3'-Dideoxynucleosides by Enzymatic Transglycosylation," Biochemical and Biophysical Research Communications, vol. 155, No. 2, 1988, pp. 829-834.
LaMontagne et al., "Preparation of 7-Substituted Pyrrolo(2,3-d)pyrimidines and 9-Substituted Purines as Potential Antiparasitic Agents," J. Heterocyclic Chem., 20, 295 (1983).
Glaudemans et al., "Syntheses with Partially Benzylated Sugars, 111, A Simple Pathway to a `cis-Nucleoside`. . . ," J. Org. Chem. vol. 28, Nov. 1963, pp. 3004-3006.
Bauman John G.
Wirsching Randolph C.
Berlex Biosciences Inc.
Rivers Diana
LandOfFree
6-azido-2-fluoropurine, useful in the synthesis of nucleosides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 6-azido-2-fluoropurine, useful in the synthesis of nucleosides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 6-azido-2-fluoropurine, useful in the synthesis of nucleosides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-102947