Discovery and optimization of 2-aryl oxazolo-pyrimidines as adenosine kinase inhibitors using liquid phase parallel synthesis

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 8, 2004, Pages 1997-2000

  Bauser, M ^a   Delapierre, G ^a,b   Hauswald, M ^a   Flessner, T ^a   D'Urso, D ^a   Hermann, A ^a   Beyreuther, B ^a   De Vry, J ^a   Spreyer, P ^a   Reissmuller E ^a   Meier, H ^a  

^a BAYER PHARMA AG   (Germany)

^b CEA LETI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE KINASE INHIBITOR; NUCLEOSIDE; PYRIMIDINE DERIVATIVE;

ARTICLE; DERIVATIZATION; DRUG SYNTHESIS; INFLAMMATION; ISCHEMIA; LIQUID; NERVE DEGENERATION; PAIN; SCREENING; SEIZURE; STRUCTURE ACTIVITY RELATION;

ADENOSINE KINASE; ENZYME INHIBITORS; MOLECULAR STRUCTURE; OXAZOLES; PYRIMIDINES;

EID: 12144289666     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.01.082     Document Type: Article

References (17)

1. All compounds prepared were chromatographically purified and analyzed using either HPLC-MS or NMR Jacobsen M.A. Expert Opin. Ther. Patents. 12:2002;489.
2. Sebastiao A.M., Ribeiro J.A. TIPS. 21:2000;341.
3. Kowaluk E.A., Bhagwat S.S., Jarvis F.J. Current Pharm. Design. 4:1998;404.
4. Gomes J.A., Li X., Pan H.L., Eisenach J.C. Anesthesiology. 1999;1072.
5. Johannson B., Halldner L., Dunwiddie T.V., Masino S.A., Poelchen W., Gimenez-Llort L., Escorihuela R.M., Fernandez-Teruel A., Wiesenfeld-Hallin Z., Xu X.J., Hardemark A., Betsholz C., Herlenius E., Fredholm B.B. PNAS. 98:2001;9407.
6. Mathews I.I., Erion M.D., Ealick S.E. Biochemistry. 37:1998;15607.
7. Zhu C.Z., Mikusa J., Chu K.L., Cowart M., Kowaluk E.A., Jarvis M.F., McGaraughty S. Brain Research. 905:2001;104.
8. Cowart M., Lee C.-H., Gfesser G.A., Bayburt E.K., Bhagwat S.S., Stewart A.O., Yu H., Kohlhaas K.L., McGaraughty S., Wismer C.T., Mikusa J., Zhu C., Alexander K.M., Jarvis M.F., Kowaluk E.A. Bioorg. Med. Chem. Lett. 11:2001;84.
9. Gomtsyan A., Didomenico S., Lee C.H., Matulenko M.A., Kim K., Kowaluk E.A., Wismer C.T., Mikusa J., Yu H., Kohlhaas K., Jarvis M.F., Bhagwat S.S. J. Med. Chem. 45:2002;3639.
10. Tolman R.L., Robins R.K., Townsend L.B. J. Am. Chem. Soc. 91:1969;2102.
11. Patil V.D., Towsend L.B. J. Heterocyclic Chem. 1971;503.
12. Bold, G.; Manley, P. W.; Martin-Kohler, A.; Sequin, U. WO Patent WO 02/092604 2002.
13. Zeng L., Burton L., Yung K., Sushan B., Kassel D.B. J. Chromatogr. A. 794:1998;4.
14. Bauser M. J. Chrom. Sci. 40:2002;292.
15. 50 values are marked with a # Yamada Y., Goto H., Ogasawara N. Biochim. Biophys. Acta. 616:1980;199.
16. Schenke, T.; Petersen, U.; Eur. Pat. Appl. EP 393424A2 1990.
17. The racemic bis-pyrrolidine was separated into the enantiomeres by chromatography, using Daicelphase Chiralcel OD as stationary phase and iso-hexane/iso-propanole (80/20 v/v and 0,05% Diethylamine) as mobil phase.