Pyridazino[3,4-b][1,5]benzoxazepin-5(6H)-ones: Synthesis and biological evaluation

Antiviral Chemistry and Chemotherapy

Volumn 7, Issue 6, 1996, Pages 300-312

  Barth, B ^a   Dierich, M ^a   Heinisch, G ^a   Jenny, V ^a   Matuszczak, B ^a   Mereiter, K ^b   Planer, R ^a   Schopf I ^a   Stoiber, H ^a   Traugott, T ^a   Aufschnaiter, P V ^a  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

HIV; non nucleosides; pyridazino 3,4 b 1,5 benzoxazepin 5(6H) ones; rev erse transcriptase inhibitors

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; NEVIRAPINE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; VIRUS ENZYME;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

EID: 10544230205     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632029600700603     Document Type: Article

References (17)

1. Adams, J., and Merluzzi, V.J. (1993) Discovery of nevirapine, a nonnucleoside inhibitor of HIV-1 reverse transcriptase. In The Search for Antiviral Drugs. Adams, J., and Merluzzi, V.J. (eds.). Birkehäuser, pp. 45-70.
2. Barth, B., Dierich, M., Heinisch, G., Matuszczak, B., Mereiter, K., Soder, J., and Stoiber, H. (submitted, 1996) Novel oxazolo[3′,2′:1,2]pyrrolo[3,4-d]pyridazines and imidazolo [1′,2′:1,2]pyrrolo[3,4-d]pyridazines: synthesis and biological evaluation. Arch Pharm Med Chem.
3. Boyode, B.P., Sinet, M., Farese, A., Forestier-Roux, M.-A., Condom, R., Ayi, I.A., Kirn, A., Moog, C., and Guedj, R. (1995) Synthesis and antiviral evaluation of fluorinated dipyridodiazepinones and dipyridodiazepines (nevirapine derivatives). Antiviral Chem Chemother 6: 162-168.
4. De Clercq, E. (1994a) Non-nucleoside reverse transcriptase inhibitors (NNRTIs). Exp Opin Invest Drugs 3: 253-271.
5. De Clercq, E. (1994b) Resistance of human immunodeficiency virus type 1 (HIV-1) to non-nucleoside HIV-1-specific reverse transcriptase inhibitors. Int J Immunotherapy 10: 145-158.
6. De Clercq, E. (1995) Antiviral therapy for human immunodeficiency virus infections. Clin Microbiol Rev 8: 200-239.
7. Hargrave, K.D., Proudfoot, J.R., Grozinger, K.G., Cullen, E., Kapadia, S.R., Patel, U.R., Fuchs, V.U., Mauldin, S.C., Vitous, J., Behnke, M.L., Klunder, J.M., Pal, K., Skiles, J.W., McNeil, D.W., Rose, J.M., Chow, G.G., Skoog, M.T., Wu, J.C., Schmidt, G., Engel, W.W., Eberlein, W.G., Saboe, T.D., Campbell, S.J., Rosenthal, A.S., and Adams, J. (1991) Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 1. Tricyclic pyrido- and dipyridodiazepinones. J Med Chem 34: 2231-2241.
8. Heinisch, G. (1973) Synthesen und Reaktionen von Pyridazinderivaten. Monatsh Chem 104: 953-962.
9. Heinisch, G., Matuszczak, B., and Mereiter, K. (1994) A novel type of 1,2-diazine → 1,2-diazole ring contraction. Heterocycles 38: 2081-2089.
10. Kelly, T.A., Proudfoot, J.R., McNeil, D.W., Patel, U.R., David, E., Hargrave, K.D., Grob, P.M., Cardozo, M., Agarwal, A., and Adams, J. (1995) Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. 5, 4-Substituted and 2, 4-disubstituted analogs of nevirapine. J Med Chem 38: 4839-4847.
11. Klunder, J.M., Hargrave, K.D., West, M.A., Cullen, E., Pal, K., Behnke, M.L., Kapadia, S.R., McNeil, D.W., Wu, U.C., Chow, J.G., and Adams, J. (1992) Novel non-nucleoside inhibitors of HIV-1 reverse transcriptase. 2. Tricyclic pyridobenzoxazepinones and dibenzoxazepinones. J Med Chem 35: 1887-1897.
12. Kohlstaedt, L.A., Wang, J., Friedman, J.M., Rice, P.A., and Steitz, T.A. (1992) Crystal structure at 3.5 Å resolution of HIV-1 reverse transcriptase complexed with an inhibitor. Science 256: 1783-1790.
13. Proudfoot, U.R., Hargrave, K.D., Kapadia, S.R., Patel, U.R., Grozinger, K.G., McNeil, D.W., Cullen, E., Cardozo, M., Tong, L., Kelly, T.A., Rose, J., David, E., Mauldin, S.C., Fuchs, V.U., Vitous, J., Hoermann, M.A., Klunder, J.M., Raghavan, P., Skiles, J.W., Mui, P., Richman, D.D., Sullivan, J.L., Shin, C.-K., Grab, P.M., and Adams, J. (1995a) Novel non-nucleoside inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. 4. 2-Substituted dipyridodiazepinones as potent inhibitors of both wild-type and cysteine-181 HIV-1 reverse transcriptase enzymes. J Med Chem 38: 4830-4838.
14. Proudfoot, J.R., Patel, U.R., Kapadia, S.R., and Hargrave, K.D. (1995b) Novel non-nucleoside inhibitors of (HIV-1) reverse transcriptase. 3. Dipyrido[2,3-b:2′,3′-e]diazepinones. J Med Chem 36: 1406-1410.
15. Ried, W., and Eichhorn, T.A. (1988) Synthese neuer potentiell analgetisch bzw. antibiotisch wirksamer Pyridazino[4,3-c][1,3]oxazinone und Pyrimido[4,5-c]pyridazinone. Arch Pharm (Weinheim) 321: 527-532.
16. Sheldrick, G.M. (1976) SHELX76. Program for crystal structure determination. University of Cambridge, England.
17. Usha, R., Bhadbhade, M.M., Venkatesan, K., Nagarajan, K., David, J. (1982) Structure and conformation of an antidepressant drug, nitroxazepine hydrochloride monohydrate. Acta Cryst B38: 1854-1857.