2-substituted-1-deaza purine derivatives with adenosine...

Details 2-substituted-1-deaza purine derivatives with adenosine... 2-substituted-1-deaza purine derivatives with adenosine...

2008-03-04

2008-03-04

Seaman, Margaret D. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S118000

Reexamination Certificate

active

07338964

ABSTRACT:
The present invention relates to 2-substituted-1-deaza purine derivatives as adenosine receptor modulating agents, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said purine derivatives.The compounds have the general formula (1)wherein the symbols have the meanings given in the specification.

REFERENCES:
patent: 4977144 (1990-12-01), Fujimoto et al.
patent: 354180 (1989-07-01), None
patent: 0 354 180 (1990-02-01), None
patent: 2004-217582 (2004-05-01), None
patent: WO 2002/31176 (2002-04-01), None
patent: WO 2004/069185 (2004-08-01), None
patent: WO 2006/027366 (2006-03-01), None
Holy et al., J. Med.Chem., “Structure-Antiviral Activity Relationship in the Series of Pyrimidine and Purine N-[2-(2-Phosphonomethoxy)ethyl] Nucleotide Analogues. 1. Derivatives Substituted at the Carbon Atoms of the Base”, 1999, vol. 42, pp. 2064-2986.
Francis et al., Canadian Journal of Chemistry, “A general synthesis of 5,7-diaminoimidazo[4,5-b]pyridine ribosides (“′2-amino-1-deazaadenosines”) from 5-amino-4-imidazolecarboxamide riboside (AICA riboside)”, 1992, vol. 70, pp. 1288-1295.
Hess et la., Expert Opin. Ther. Patents, “Recent advances in adenosine receptor antagonist research”, 2001, vol. 11, pp. 1533-1561.
Baraldi et al., Expert opin. Ther. Patents, “Allosteric modulators for the A1-adenosine receptor”, 2004, vol. 14, pp. 71-79.
Yan et al., Expert Opin. Emerging Drugs, “Adenosine receptor agonists: from basic medicinal chemistry to clinical development”, 2003, vol. 8, pp. 537-576.
Francis, J.E., et al., “A general synthesis of 5,7-diaminoimidazo[4,5-b]pyridine ribosides (“2-amino-1-deazaadenosines”) from 5-amino-4-imidazolecarboxamide riboside (AICA riboside),” Canadian J. Chem. 70, pp. 1288-1295, (1992).
Camaioni, E., et al., “New Substituted 9-Alkylpurines as Adenosine Receptor Ligands,” Bioorganic & Medicinal Chemistry 6(5), pp. 523-533 (1998).
Wanner, M.J., et al., “2-Nitro Analogues of Adenosine and 1-Deazaadenosine: Synthesis and Binding Studies at the Adenosine A1,A2Aand A3Receptor Subtypes,” Bioorganic & Medicinal Chemistry Letters, vol. 10, No. 18, pp. 2141-2144 (2000).
Sullivan, G.W., et al., “Cyclic AMP-dependent inhibition of human neutrophil oxidative activity by substituted 2-propynlcyclohexyl adenosine A2Areceptor agonists,” British Journal of Pharmacology, vol. 132, No. 5, (Mar. 3, 2001), pp. 1017-1026 (XP002322595).
Niiya et al., “2-(N′-Alkylidenehydrazino) Adenosines: Potent and Selective Coronary Vasodilators,” Journal of Medicinal Chemistry, vol. 35, No. 24, (1992), pp. 4557-4561.
Medicinal Chemistry: “Principles and Practice,” (1994), ISBN 0-85186-494-5, Ed.: F.D. King, p. 215.
Stella, J., “Prodrugs As Therapeutics,” Expert Opin. Ther. Patents, 14(3), pp. 277-280 (2004).
Ettmayer, P., et al., “Lessons Learned from Marketed and Investigational Prodrugs,” J. Med. Chem., 47 (10), pp. 2393-2404, (2004).
Cristalli et al., “Improved Synthesis and Antitumor Activity of 1-Deazaadenosine” J. Med. Chem. (1987), 30, pp. 1686-1688.
Itoh et al., “Studies on the Chemical synthesis of Potential Antimetabolites Regioselective Introduction of a Chlorine Atom into the Imidazo [4,5-b]pyridine Nucleus (1),” J. Heterocyclic Chem. (1982), 19, pp. 513-517.
Deghati et al., “Mild and Regioselective Nitration of 1-deazapurine Nucleosides using TBAN/TFAA,” Tetrahedron Letters (2000), 41, pp. 569-573.
Wanner et al., “Synthesis and Properties of 2-nitrosoadenosine,” J. Chem. Soc. Perkin Trans 1, (2001), pp. 1908-1915.
Townsend, A., et al., “A Threonine Residue in the Seventh Transmemebrane Domain of the Human A1Adenosine Receptor Mediates Specific Agonist Binding,” Biol. Chem., 269, p. 2373-2376 (1994).
Luthin, D.R., et al., “Characterization of Two Affinity States of Adenosine A2aReceptors with a New Radioligand, 2-[2-(4-Amino-3-[125I]iodophenyl)ethylamino]adenosine,” Mol. Pharmacol., 47, p. 307 (1995).
Stehle, J.H., et al., “Molecular Cloning and Expression of the cDNA for a Novel A2-Adenosine Receptor Subtype,” Mol. Endocrinol., 6, p. 384, (1992).
Salvatore, C.A., et al., “Molecular Cloning and Characterization of the Human A3Adenosine Receptor,” Proc. Natl. Acad. Sci. USA, 90, pp. 10365-10369 (1993).
Hess, S., “Recent Advances in Adenosine Receptor Antagonist Research”, Expert Opin. Ther. Patents, 11, pp. 1547-1562, (2001).
Jacobsen, M.A., “Adenosine Receptor Agonists,” Expert Opin. Ther. Patents, 12(4), pp. 489-501, (2002).
Cristalli, G., et al., II “Purine and Deazapurine n=Nucleosides: Synthetic Approaches, Molecular Modeling and Biological Activity,” Farmaco, 58, pp. 193-204, (2003).
Klotz, K., et al., “9-Ethyladenine Derivatives as Adenosine Receptor Antagonists: 2- and 8-substitution results in distinct selectivities, Naunyn-Schmiedeberg's Archives of Pharmacology,” 367, pp. 629-634 (2003).
Ginger-Sorolla, A., et al., “Fluorine-containing and Purines: Synthesis and Properties of Trifluoromethyl Pyrimidines and Purines1,” JACS 80, pp. 5744-5752, (1958).
Kaiser, C., et al., “A Synthesis of 2-Amino-6-trifluoromethyl-purine,” J. Org. Chem. 24, pp. 113-114, (1959).
Nagano, H., et al., “Fluorine-Containing Potential Anticancer Agents. II.1aSyntheses of Some Trifluoromethylpurines and Trifluoromethylthiazolopyrimidines1b,” J. of Med. Chem, Amer. Chem. Soc., vol. 7, no., pp. 215-220, (1964).
Kobayashi, Y., et al. “Studies on Organic Fluorine Compounds. Part 35.1Trifluoromethyl-ation of Pyrimidine- and Purine-nucleosides with Trifluoromethyl-Copper Complex,” J. Chem. Soc. Perkin 1, pp. 2755-2761, (1980).
Green, A.R., et al., “The Effect of the C-6 Substituent on the Regioselectivity of N-Alkylation of 2-Aminopurines,” Tetrahedron vol. 46, No. 19 pp. 6903-6914, (1990).
Hockova, D., et al., “Synthesis of Cytostatic Activity of Nucleosides and Acyclic Nucleoside Analogues Derived from 6-(Trifluoromethyl)purines,” Tetrahedron 55, pp. 11109-11118, (1990).
Veliz, E.A., et al. “Synthesis and Analysis of RNA Containing 6-Trifluoromethylpurine Ribonucleoside,” Organic Letters, vol. 3, No. 19, pp. 2969-2972 (2001).
Hocek, M., et al., “Perfluoraoalkylation of 6-Iodopurines By Trimethyl(Perfluoroalkyl)Silanes. Synthesis of 6-(Perfluoroalkyl)Purine Bases, Nucleosides and Acyclic Nucleotide Analogues,” Collection of Czechoslovak Chemical Communications, 64, p. 229-241, (1999).
Ueeda, M. et al., “2-Alkoxyadenosines: Potent and Selective Agonists at the Coronary Artery A2Adenosine Receptor,” J. Med. Chem., 34, pp. 1334-1339, (1991).
Rodenko, B., et al., “Solid Phase Synthesis of C2,N6-disubstituted adenosine analogues,” J. Chem. Soc., Perkin Trans., 1, (2002), pp. 1247-1252.
Rodenko, B., et al., “The Mechanism of Selective Purine C-Nitration Revealed: NMR Studies Demonstrate Formation and Radical Rearrangement of an N7-Nitramine Intermediate,” J. A.M. Chem. Soc., (2005), 127, pp. 5957-5963.
Gao Z.G., et al., “2-Substituted Adenosine Derivatives: Affinity and Efficacy at Four Subtypes of Human Adenosine Receptors,” Biochemical Pharmacology 68 (2004) pp. 1985-1993.
Nanner, M.J., et al., “2-Nitro Analogues of Adenosine and 1-Deazaadenosine: Synthesis and Binding Studies at the Adenosine A1, A2Aand A3Receptor Subtypes,” Bio. & Med. Chem. Letter, 10, pp. 2141-2144 (2000).
Search Report for PCT/EP2005/054405 dated Jan. 2, 2006.
Search Report for PCT/EP2005/054404 dated Jan. 16, 2006.
Co-pending U.S. Appl. No. 11/219,818, filed Sep. 7, 2005.
English language Derwent Abstract for JP 2004-217582.

Affiliated with

Also associated with

Rating

2-substituted-1-deaza purine derivatives with adenosine... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 2-substituted-1-deaza purine derivatives with adenosine..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 2-substituted-1-deaza purine derivatives with adenosine... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2803903