8-Heteroaryl xanthine adenosine A 2B receptor antagonists

Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C544S269000, C544S270000, C544S118000, C436S501000, C436S804000, C548S243000

Reexamination Certificate

active

10357865

ABSTRACT:
The present invention relates generally to compounds of the formula (I):wherein:X is a five or six-membered heteroaromatic ring, containing one to four heteroatoms, selected from nitrogen, oxygen, or sulfur, provided that at least one heteroatom is nitrogen; andG1and G2are independently CH or N.The present invention also relates to the preparation of the compounds, pharmaceutical formulations thereof, and their use in medicine as potent or selective A2Badenosine receptor antagonists and their uses for treating asthma, autoimmune diseases and retinal vascular diseases.

REFERENCES:
patent: 4567183 (1986-01-01), Sunshine et al.
patent: 4593095 (1986-06-01), Snyder et al.
patent: 4772607 (1988-09-01), Badger et al.
patent: 5424297 (1995-06-01), Rubio et al.
patent: 5935964 (1999-08-01), Baraldi et al.
patent: 6117878 (2000-09-01), Linden
patent: 6825349 (2004-11-01), Kalla et al.
patent: 6977300 (2005-12-01), Kalla et al.
patent: 2004/0176399 (2004-09-01), Elzein et al.
patent: 2005/0065341 (2005-03-01), Wang et al.
patent: 2005/0101778 (2005-05-01), Kalla et al.
patent: 2005/0261316 (2005-11-01), Kalla et al.
patent: 0 267 607 (1987-11-01), None
patent: 956855 (1999-11-01), None
Mueller, J. Med Chem 36(22) pp. 3341-3349.
International Search Report dated Sep. 2, 2003, issued in corresponding PCT Patent Application No. PCT/US03/03224.
Baraldi et al. (1996), “Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]-pyrimidine derivatives: potent and selective A2A adenosine antagonists”, J Med Chem. 39: 1164-1171.
Baraldi et al. (1998), “Design, synthesis and biological evaluation of a second generation of pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]- pyrimidines as potent and selective A2A adenosine receptor antagonists”, J Med Chem 41: 2126-2133.
Baraldi et al. (1999), “Pyrazolo[4,3-e] 1,2,4-triazolo[1,5c]pyrimidine derivatives as highly potent and selective human A3 adenosine receptor antagonists”, J Med Chem 42: 4473-4478.
Baraldi et al. (2000). “A3 Adenosine receptor ligands; history and perspectives”, Med Res Rev 20: 103-128.
Baraldi et al. (2001). “Pyrazolo[4,3-e] 1,2,4-triazolo[1,5-c]pyrimidine derivatives as adenosine receptor ligands: a search for A2B adenosine receptor”, Drug Dev Res., 53, 225-235.
Boyle et al. (1996), “Inhibition of synoviocyte collagenase gene expression by adenosine receptor stimulation”, Arthritis Rheum 39: 923-930.
Bradford M M. (1976), “A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein dye-binding”, Anal Biochem 72: 248-254.
Cheng Y. C. and Prusoff W. H. (1973), “Relationships between the inhibition constant (K.sub.i) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction”, Biochem. Pharmacol., 22: 3099-3 108.
Daly et al. (1983), “Subclasses of adenosine receptors in the central nervous system: interaction with caffeine and related methylxanthines”, Cell Mol Neurobiol 3: 69-80.
De Zwart et al. (1999), “Potent antagonist for the human adenosine A2B receptor. Derivatives of the triazolotriazine adenosine receptor antagonist ZM241385 with high affinity”, Drug Dev Res 48: 95-103.
Dubey et al. (1996), “Adenosine inhibits growth of rat aortic smooth muscle cells: possible role of A2B receptors”, Hypertension 27: 786-793.
Feoktistov I, and Biaggioni I. 1995, “Adenosine A2B receptors evoke interleukine-S secretion in human mast cells: an enprofylline-sensitive mechanism with implication for asthma”, J. Clin Invest 96: 1979-1986.
Feoktistov I, and Biaggioni I. (1997), “Adenosine A2B receptors”, Pharmacol Rev49: 381-402.
Feoktistov I, Biaggioni I. (1998), “Pharmacological characterization of adenosine A2B receptors”, Biochem Pharmacol 55: 627-633.
Feoktistov et al. (1998), “Adenosine A2B receptors as therapeutic targets”, Drug Dev. Res 45: 198-206.
Haynes et al. (1995), “Adenosine-induced vasodilation receptor characterization in pulmonary circulation”, Am J Physiol 26S: H1862-H1868.
Jacobson et al. (1999), “1,3-Dialkylxanthine derivatives having high potency as antagonists at human A2B adenosine receptors”, Drug Dev. Res 47: 45-53.
Ji X-D. and Jacobson K A. (1999), “Use of triazolotriazine [3H]-ZM241385 as a radioligand at recombinant human A2B adenosine receptors”, Drug Des Discov 16: 217-226.
Ji X-D. Kim Y-C, Ahem D. G., Linden J., Jacobson K A. (2001), “[3H]-MRS-1754, a selective antagonist radioligand for A2B adenosine receptors”, Biochem Pharmacol, 61: 657-663.
Kim Y-C. et al. (1998) “Derivatives of the triazoloquinazoline adenosine antagonist (CGS 15943) having high potency at the human A2B and A3 receptor subtypes”, J Med Chem 41: 2835-2845.
Kim Y-C et al. (1999), “Acyl-hydrazide derivatives of a xanthine carboxylic congener (XCC) as selective antagonists at human A.sub.2B adenosine receptors”, Drug Dev Res 47: 178-188.
Kim Y-C et al.. (2000), “Anilide derivatives of an 8-phenylxanthine carboxylic congener are highly potent and selective antagonists at human A.sub.2B adenosine receptors”, J Med Chem 43: 1165-1172.
Klotz et al. (1998), “Comparative pharmacology of human adenosine receptor subtypes characterization of stably transfected receptors in CHO cells”, Naunyn-Schmied. Arch Pharm. 357:1-9.
Londos et al. (1980), “Subclasses of external adenosine receptors”, Proc Natl Acad Sci USA 77: 2551-2554.
Marquardt et al.. (1994), “Cloning of two adenosine receptor subtypes from mouse bone marrow derived mast cells”, J Immunol 152: 4508-4515.
Mateo et al. (1995), “5-(N-ethylcarboxamido)-adenosine inhibits Ca2+, influx and activates a protein phosphatase in bovine adrenal chromaffin cells”, J Neurochem 64: 77-84.
Murthy et al. (1995), “Adenosine A1, and A.sub.2B receptors coupled to distinct interactive signaling pathways in intestinal muscle cells”, J Pharmacol Exp Ther 274: 243-2-46.
Munson et al. (1980), “Ligand: a versatile computerized approach for the characterization of ligand binding systems”, Anal. Biochem., 107: 220-239.
Varani et al. (1998), “[3H]-SCH58261 labelling of functional A2A adenosine receptors in human neutrophil membranes”, Br. J. Pharmacol., 123: 1723-1731.
Varani et al. (2000), “[3H]-MRE3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A3 adenosine receptors”, Mol. Pharmacol., 57: 968-975.
Zocchi et al. (1996), “Binding of the radioligand [3H]-SCH58261, a new non-xanthine A2A adenosine receptor antagonist, to rat striatal membranes”, Br J Pharmacol. 117: 1381-1386.
Apr. 28, 2005, Supplementary European Search Report for EP 03 71 0831.
Hayallah et al., Feb. 14, 2002, “1,8-Disubstituted Xanthine Derivatives: Synthesis of potent A2B-selective Adenosine Receptor Antagonists”, J. of Med. Chemistry, vol. 45, No. 7, pp. 1500-1510.
Kim et al., Apr. 25, 2002, “Structure-activity Relationships at Human and Rat A2B Adenosine Receptors of Xanthine Derivatives Substituted at 1-, 3, 7-, and 8-positions”, J. of Med. Chemistry. vol. 45, No. 11, 23, pp. 2131-2138.

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

8-Heteroaryl xanthine adenosine A 2B receptor antagonists does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 8-Heteroaryl xanthine adenosine A 2B receptor antagonists, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 8-Heteroaryl xanthine adenosine A 2B receptor antagonists will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3751989

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