Progress towards novel adenosine receptor therapeutics gleaned from the recent patent literature

Bibliography

• Bayer Schering Pharma AG. Preparation of 4-phenyl-3,5-dicyanopyridines as cardiovascular agents. WO2009100827; 2009
   Google Scholar
• Bayer Healthcare AG. Preparation of 4-amino-3,5-dicyano-2-thiopyridines as cardiovascular agents. WO2008064789; 2008
   Google Scholar
• Bayer Healthcare AG. Preparation of 3,4′-bipyridines and related compounds as adenosine receptor ligands. WO2008028590; 2008
   Google Scholar
• Bayer Healthcare AG. Preparation of 3,5-dicyano-2-thiopyridines as cardiovascular agents. WO2008064788; 2008
   Google Scholar
• Bayer Healthcare AG. Synthesis of dipeptoid prodrugs for use in the treatment of cardiovascular illnesses. WO2009015811; 2009
   Google Scholar
• Bayer Healthcare AG. Preparation of prodrug phenylpyridinethiols as cardiovascular agents. WO2009015812; 2009
   Google Scholar
• Bayer A-G. Preparation of 2-thio-3,5-dicyano-4-phenyl-6-aminopyridines as adenosine A1 receptor agonists. DE10238113; 2003
   Google Scholar
• Tendera M, Sosnoswki M, Gaszeewska-Zurek E, The oral adenosine A1 receptor agonist, BAY 68-4986, reduces heart rate at peak exercise in patients with chronic stable angina [abstract]. J Am Coll Cardiol 2010;49:825-6
   Google Scholar
• Bayer Schering Pharma AG. Cyanopyridine derivatives as adenosine receptor agonists and antagonists and their preparation and use in the treatment of cardiovascular diseases. WO2009080198; 2009
   Google Scholar
• Bayer Schering Pharma AG. Azabicyclic compounds as adenosine receptor agonists and antagonists and their preparation and use in the treatment of cardiovascular diseases. WO2009080197; 2009
   Google Scholar
• King Pharmaceuticals Research and Development Inc. Allosteric adenosine A1 receptor enhancer pharmaceutical compositions for the treatment of pain. WO2008147939; 2008
   Google Scholar
• Baraldi PG, Moorman A. Preparation of substituted 2-amino-3-aroylthiophenes as allosteric modulators of the A1 adenosine receptor. US2008119460; 2008
   Google Scholar
• King Pharmaceuticals Research and Development, Inc. Combination therapy using an allosteric adenosine A1 receptor enhancer with an opioid analgesic or AMPA/kainate antagonists for the treatment of pain. WO2008051760; 2008
   Google Scholar
• King Pharmaceuticals Research and Development, Inc. Preparation of 3-aroylthiophene-2-amines as allosteric enhancers of the A1 adenosine receptor. WO2009137782; 2009
   Google Scholar
• Goeblyoes A, Ijzerman AP. Allosteric modulation of adenosine receptors. Purinergic Signal 2009;5(1):51-61
   PubMedGoogle Scholar
• Baraldi PG, Iaconinoto MA, Moorman AR, Allosteric enhancers for A1 adenosine receptor. Mini Rev Med Chem 2007;7(6):559-69
   PubMedGoogle Scholar
• Romagnoli R, Baraldi PG, Carrion MD, Synthesis and biological evaluation of 2-amino-3-(4-Chlorobenzoyl)-4-[N-(substituted) piperazin-1-yl]thiophenes as potent allosteric enhancers of the A1 adenosine receptor. J Med Chem 2008;51(18):5875-9
   PubMedGoogle Scholar
• Baraldi PG, Pavani MG, Leung E, Synthesis and biological characterization of [3H] (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(4-chlorophenyl)methanone, the first radiolabeled adenosine A1 allosteric enhancer. Bioorg Med Chem Lett 2006;16(5):1402-4
   PubMedGoogle Scholar
• De Vry J, Kuhl E, Franken-Kunkel P, Pharmacological characterization of the chronic constriction injury model of neuropathic pain. Eur J Pharmacol 2004;491(2-3):137-48
   PubMedGoogle Scholar
• King Pharmaceuticals Research and Development, Inc. Crystals of (2-amino-4,5,6,7-tetrahydrobenzo[b]thien-3-yl) (4-chlorophenyl)methanone and dosage forms comprising the same. US2009023799; 2009
   Google Scholar
• Laska EM, Sunshine A, Mueller F, Caffeine as an analgesic adjuvant. JAMA 1984;251:1711-8
   PubMed Web of Science ®Google Scholar
• ReGen Therapeutics plc Transdermal therapy. WO2008056139; 2008
   Google Scholar
• Revolymer Ltd. Medicated chewing gum. WO2008104547; 2008
   Google Scholar
• Novacardia, Inc. KW-3902 conjugates that do not cross the blood-brain barrier and their use as diuretics. WO2008024277; 2008
   Google Scholar
• Perry R, Fetherston J. Yersina pestis – etiologic agent of plague. Clin Microbiol Rev 1997;10:35-66
   PubMed Web of Science ®Google Scholar
• Wilson C, Batra V. Lipopolysaccharide binds to and activates A1 adenosine receptors on human pulmonary artery endothelial cells. J Endotox Res 2002;8:263-71
   PubMedGoogle Scholar
• Neely C, Jin J, Keith I. A1-adenosine receptor antagonists block endotoxin-induced lung injury. Am J Physiol 1997;272:L353-61
   PubMed Web of Science ®Google Scholar
• Nadeem A, Obiefuna P, Wilson C, Adenosine A1 receptor antagonist versus montelukast on airway reactivity and inflammation. Eur J Pharmacol 2006;551:116-24
   PubMedGoogle Scholar
• Endacea, Inc. Methods using an A1 adenosine receptor antagonist for preventing and treating tissue injury and sepsis associated with Yersinia pestis infection. US20090048155; 2009
   Google Scholar
• Santen Pharmaceutical Co., Ltd. Therapeutic agent for glaucoma comprising adenosine A2A receptor agonist as active ingredient. WO2008133129; 2008
   Google Scholar
• Santen Pharmaceutical Co., Ltd. Preparation of adenosine nucleoside analogs as therapeutic agent for glaucoma. WO2008130520; 2008
   Google Scholar
• Novartis AG. Preparation of purine nucleoside derivatives as A2A receptor agonists. WO2008006563; 2008
   Google Scholar
• Biovitrum AB. Preparation of nucleosides as therapeutic compounds for the treatment of pain and inflammation. WO2008000745; 2008
   Google Scholar
• Biovitrum AB. 2′,3′-Methylidene acetal adenosine prodrugs of improved oral absorption and their use as therapeutic analgesic or antiinflammatory compounds. WO2008000743; 2008
   Google Scholar
• Pgxhealth. Substituted 4-piperidine-1-carboxylic acid esters as A2A R agonists and therapeutic uses thereof. US2009162292; 2009
   Google Scholar
• Azam F, Ibn-Rajab IA, Alruiad AA. Adenosine A2A receptor antagonists as novel anti-Parkinsonian agents: a review of structure-activity relationships. Pharmazie 2009;64(12):771-95
   PubMedGoogle Scholar
• Pinna A. Novel investigational adenosine A2A receptor antagonists for Parkinson's disease. Expert Opin Invest Drugs 2009;18(11):1619-31
   PubMedGoogle Scholar
• Morelli M, Carta AR, Jenner P. Adenosine A2A receptors and Parkinson's disease (adenosine receptors in health and disease). Handb Exp Pharmacol 2009;193:589-615
   PubMedGoogle Scholar
• Schering Corp. Preparation of aminoquinoxalines and aminoquinolines as adenosine A2A receptor antagonists. WO2009111442; 2009
   Google Scholar
• Schering Corp. Preparation of 1,2,4-triazolo[4,3-c]pyrimidin-3-ones and pyrazolo[4,3-e]-1,2,4-triazolo[4,3-c]pyrimidin-3-ones as adenosine A2A receptor antagonists for treatment of CNS disorders. WO2009111449; 2009
   Google Scholar
• Schering Corp. Preparation of triazoloquinazolinamines as adenosine A2A receptor antagonists. WO2008002596; 2009
   Google Scholar
• Janssen Pharmaceutica. Arylindenopyrimidines and their use as adenosine A2A receptor antagonists. WO2009055548; 2009
   Google Scholar
• Janssen Pharmaceutica Preparation of arylindenopyrimidines and their use as adenosine A2A receptor antagonists. WO2009055308; 2009
   Google Scholar
• King Pharmaceuticals Research and Development, Inc. Preparation of pyrrolotriazolopyrimidine derivs. as adenosine A2A receptor antagonists. WO2008121748; 2008
   Google Scholar
• Neustadt BR, Hao J, Lindo N, Potent, selective, and orally active adenosine A2A receptor antagonists: arylpiperazine derivatives of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines. Bioorg Med Chem Lett 2007;17(5):1376-80
   PubMed Web of Science ®Google Scholar
• Neustadt BR, Liu H, Hao J, Potent and selective adenosine A2A receptor antagonists: 1,2,4-Triazolo[1,5-c]pyrimidines. Bioorg Med Chem Lett 2009;19(3):967-71
   PubMed Web of Science ®Google Scholar
• Hodgson RA, Bertorelli R, Varty GB, Characterization of the potent and highly selective A2A receptor antagonists preladenant and SCH412348 [7-[2-[4-2,4-difluorophenyl]-1-piperazinyl]ethyl]-2-(2-furanyl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine] in rodent models of movement disorders and depression. J Pharmacol Exp Ther 2009;330(1):294-303
   PubMed Web of Science ®Google Scholar
• Gillespie RJ, Bamford SJ, Botting R, Antagonists of the human A2A adenosine receptor. 4. Design, synthesis, and preclinical evaluation of 7-aryltriazolo[4,5-d]pyrimidines, J Med Chem 2009;52(1):33-47
   PubMed Web of Science ®Google Scholar
• Biogen Idec MA, Inc. Preparation of [1,2,3]triazolo[4,5-d]pyrimidine compounds as purine receptor antagonists. WO2008088927; 2008
   Google Scholar
• CV Therapeutics, Inc. Thienopyrimidinedione derivatives as A2A adenosine receptor antagonists and their preparation, pharmaceutical compositions and use in the treatment of diseases. WO2008070529; 2008
   Google Scholar
• Adenosine Therapeutics. Preparation of purine derivatives as selective antagonists of A2A adenosine receptors. WO2008011007; 2008
   Google Scholar
• Neurocrine Biosciences, Inc. Preparation of pyrimidines as adenosine A2A receptor antagonists. WO2008116185; 2008
   Google Scholar
• Neurocrine Biosciences, Inc. Substituted pyrimidines as adenosine receptor antagonists. WO2008070661; 2008
   Google Scholar
• Press NJ, Gessi S, Borea PA, Therapeutic potential of adenosine receptor antagonists and agonists. Expert Opin Ther Pat 2007;17(8):979-91
   PubMedGoogle Scholar
• Almirall. Preparation of 5-phenyl-6-(pyridin-4-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one derivatives as A2B adenosine receptor antagonists. WO2008080461; 2008
   Google Scholar
• Adenosine Therapeutics. Preparation of pyrrolo[3,2-d]pyrimidines as selective antagonists of A2B adenosine receptor. US7470697; 2008
   Google Scholar
• Caruso M, Varani K, Tringali G, Adenosine and adenosine receptors: their contribution to airway inflammation and therapeutic potential in asthma. Curr Med Chem 2009;16(29):3875-85
   PubMedGoogle Scholar
• Feoktistov I, Biaggioni I. Adenosine A2B receptors. Pharmacol Rev 1997;48:381-402
   Google Scholar
• Fozard JR, Hannon JP. Species differences in adenosine-induced bronchoconstrictor responses. Clin Exp Allergy 2000;30:1213-20
   PubMedGoogle Scholar
• Elzein E, Kalla RV, Li X, Discovery of a novel A2B adenosine receptor antagonist as a clinical candidate for chronic inflammatory airway diseases. J Med Chem 2008;51(7):2267-78
   PubMedGoogle Scholar
• CV Therapeutics, Inc. Preparation of purinedione derivatives as A2B adenosine receptor antagonists for the treatment of cancer. WO2009088518; 2009
   Google Scholar
• Bar-Yehuda S, Stemmer SM, Madi L, The A3 adenosine receptor agonist CF102 induces apoptosis of hepatocellular carcinoma via de-regulation of the Wnt and NF-kB signal transduction pathways. Int J Oncol 2008;33(2):287-95
   PubMed Web of Science ®Google Scholar
• Can-Fite Biopharma Ltd. Method using an adenosine A3 receptor (A3AR) agonist for inducing hepatocyte proliferation, and uses thereof. WO2009050707; 2009
   Google Scholar
• Can-Fite Biopharma Ltd. Methotrexate combination with A3 adenosine receptor agonist for the treatment of cancer. WO2008023362; 2008
   Google Scholar
• United States Dept. of the Army. Methods using adenosine A3 receptor agonists to protect skeletal muscle against injury. US2008312180; 2008
   Google Scholar
• Kim Y, de Castro S, Gao Z-G, Novel 2- and 4-substituted 1H-Imidazo[4,5-c]quinolin-4-amine derivatives as allosteric modulators of the A3 adenosine receptor. J Med Chem 2009;52(7):2098-108
   PubMedGoogle Scholar
• Gao Z-G, Ye K, Goblyos A, Flexible modulation of agonist efficacy at the human A3 adenosine receptor by the imidazoquinoline allosteric enhancer LUF6000. BMC Pharmacol 2008;8:20
   PubMedGoogle Scholar
• Heitman LH, Goeblyos A, Zweemer AM, A series of 2,4-disubstituted quinolines as a new class of allosteric enhancers of the adenosine A3 receptor. J Med Chem 2009;52(4):926-31
   PubMedGoogle Scholar
• The Government of the USA, represented by the Secretary, Dept. of Health and Human Services. Preparation of imidazoquinolinamines as A3 adenosine receptor allosteric modulators. US2009054476; 2009
   Google Scholar
• Universiteit Leiden, Neth.; Can-Fite Biopharma Ltd. Preparation of 2,4-disubstituted quinoline derivatives A3 adenosine receptor allosteric modulators. WO2010020981; 2010
   Google Scholar
• Ravn J, Qvortrup K, Rosenbohm C, Design, synthesis, and biological evaluation of LNA nucleosides as adenosine A3 receptor ligands Bioorg Med Chem 2007;15(16):5440-7
   PubMedGoogle Scholar
• Santaris Pharma. Preparation of locked nucleosides as adenosine receptor antagonists. WO2008006369; 2008
   Google Scholar
• Tosh DK, Jacobson KA, Jeong LS. Nucleoside-based adenosine A3 receptor antagonists as drug candidates. Drugs Future 2009;34(1):43-52
   Google Scholar
• FM Therapeutics Co. Preparation of adenosine nucleoside analogs for the prevention and treatment of the inflammatory diseases. WO2008108508; 2008
   Google Scholar
• Addex Pharma. Preparation of heteroaryl derivatives as therapeutic antagonists of adenosine A3 receptor. WO2009010871; 2009
   Google Scholar
• Sanofi-Aventis. Preparation of triazolo[1,5-a]quinolines as adenosine A3 receptor ligands for treating disease. WO2008149168; 2008
   Google Scholar
• Nell P, Albrecht-Küpper B. The adenosine A1 receptor and its ligands. Prog Med Chem 2009;47:163-201
   PubMedGoogle Scholar
• Vu CB, Kiesman WF, Conlon PR, Tricyclic imidazoline derivatives as potent and selective adenosine A1 receptor antagonists, J Med Chem 2006;49(24):7132-9
   PubMedGoogle Scholar
• Patel RAG, Glover DK, Broisat A, Reduction in myocardial infarct size at 48 hours after brief intravenous infusion of ATL-146e, a highly selective adenosine A2A receptor agonist. Am J Physiol Heart Circ Physiol 2009;297(2 Pt 2):H637-42
   Google Scholar
• Eckle T, Krahn T, Grenz A, Cardioprotection by ecto-5′-nucleotidase (CD73) and A2B adenosine receptors. Circulation 2007;115:1581-90
   PubMed Web of Science ®Google Scholar
• Choi, WJ, Lee HW, Design and synthesis of N6-substituted-4′-thioadenosine- 5′-uronamides as potent and selective human A3 adenosine receptor agonists. Bioorg Med Chem 2009;17(23):8003-11
   PubMedGoogle Scholar
• Okamura T, Kurogi Y, Hashimoto K, Structure-activity relationships of adenosine A3 receptor ligands: new potential therapy for the treatment of glaucoma. Bioorg Med Chem Lett 2004;14(14):3775-9
   PubMedGoogle Scholar