Novel pyrrolinones as N-methyl-D-aspartate receptor antagonists

European Journal of Medicinal Chemistry

Volumn 40, Issue 4, 2005, Pages 391-400

  Poschenrieder, Hermann ^a   Stachel, Hans Dietrich ^a   Höfner, Georg ^a   Mayer, Peter ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Azafulvenes; Glycine antagonists; Nitrones; Nitronic acid esters; Tetramic acids

Indexed keywords

2 BENZYLIDENE 4 NITRO 5 PHENYLAMINO 1,2 DIHYDROPYRROL 3 ONE; 2 BENZYLIDENE 5 (4 CHLOROPHENYLAMINO) 2H PYRROLE 3,4 DIONE 4 OXIME; 2 BENZYLIDENE 5 METHOXY 2H PYRROLE 3,4 DIONE 4 OXIME; 2 BENZYLIDENE 5 METHOXY 4 METHYLNITRORYL 2,4 DIHYDROPYRROL 3 ONE; 2 BENZYLIDENE 5 METHOXY 4 NITRO 1,2 DIHYDROPYRROL 3 ONE; 2 BENZYLIDENE 5 PHENYLAMINO 2H PYRROLE 3,4 DIONE 4 OXIME; 2 BROMOPHENYLMETHYLENE 3 HYDROXY 4 NITRO 1H PYRROL 5 ONE; 2 BROMOPHENYLMETHYLENE 5 ETHOXY 1,2 DIHYDROPYRROL 3 ONE; 2 BROMOPHENYLMETHYLENE 5 METHOXY 2H PYRROLE 3,4 DIONE 4 OXIME; 2 BROMOPHENYLMETHYLENE 5 METHOXY 4 NITRO 1,2 DIHYDROPYRROL 3 ONE; 2 BROMOPHENYLMETHYLENE 5 PHENYLAMINO 2H PYRROLE 3,4 DIONE 4 OXIME; 2 BROMOPHENYLMETHYLENE 5 PHENYLAMINO 4 NITRO 1,2 DIHYDROPYRROL 3 ONE; 5 BENZYLAMINO 2 BENZYLIDENE 2H PYRROLE 3,4 DIONE 4 OXIME; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; METHYLATION; NONHUMAN; STRUCTURE ACTIVITY RELATION; X RAY DIFFRACTION;

EID: 16244419065     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejmech.2004.11.010     Document Type: Article

References (24)

1. F.G. Salituro, B.L. Harrison, B.M. Baron, P.L. Nyce, K.T. Stewart, and I.A. McDonald J. Med. Chem. 33 1990 2946 2948
2. P.D. Leeson, R. Baker, R.W. Carling, N.R. Curtis, K.W. Moore, and B.J. Williams J. Med. Chem. 34 1991 1243 1252
3. N.J. Sucher, M. Awobuluyi, Y.-B. Choi, and S.A. Lipton Trends Pharmacol. Sci. 17 1996 348 355
4. S.A. Lipton, P.A. Rosenberg, New Engl. J. Med. 330 (1994) 613-622; B.S. Meldrum, Excitatory Amino Acid Transmissions, Alan R. Riss, New York, 1987.
5. S.A. Lipton, P.A. Rosenberg, New Engl. J. Med. 330 (1994) 613-622; B.S. Meldrum, Excitatory Amino Acid Transmissions, Alan R. Riss, New York, 1987.
6. M. Jansen, and G. Dannhardt Eur. J. Med. Chem. 38 2003 661 670
7. G. Dannhardt, and B.K. Kohl Curr. Med. Chem. 5 1998 253 263
8. H. Poschenrieder, G. Höfner, and H.-D. Stachel Arch. Pharm. Pharm. Med. Chem. 332 1999 309 316
9. H. Przewosny, H.-D. Stachel, H. Poschenrieder, US Patent 6,642,267 B2, 2003; H. Przewosny, H.-D. Stachel, H. Poschenrieder, US Patent 6,715,872 B2, 2004.
10. H. Przewosny, H.-D. Stachel, H. Poschenrieder, US Patent 6,642,267 B2, 2003; H. Przewosny, H.-D. Stachel, H. Poschenrieder, US Patent 6,715,872 B2, 2004.
11. H.-D. Stachel, H. Poschenrieder, and E. Immerz-Winkler J. Heterocycl. Chem. 20 1983 935 941
12. B. Eistert, R. Müller, H. Selzer, and E.-A. Hackmann Ber. Dtsch. Chem. Ges. 97 1964 2469 2478
13. E. Breuer Nitrones and nitronic acid derivatives S. Patai Z. Rappoport Nitrones, Nitronates and Nitroxides 1989 Wiley Chichester 139ff
14. J.U. Nef Liebigs Ann. Chem. 280 1894 263 291
15. N. Kornblum, and R.A. Brown J. Am. Chem. Soc. 86 1964 2681 2687
16. T. Severin, and B. Brück Ber. Dtsch. Chem. Ges. 98 1965 3847 3853
17. T. Nielson Nitronic acid derivatives S. Patai Z. Rappoport Nitrones, Nitronates and Nitroxides 1989 Wiley Chichester 1ff
18. H.-D. Stachel, and H. Poschenrieder Arch. Pharm. (Weinheim) 318 1985 311 318
19. G. Höfner, and K.T. Wanner Neurosci. Lett. 226 1997 79 82
20. Y.-C. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099 3108
21. M. Mawer, J.J. Kulagowski, P.D. Leeson, S. Grimwood, and G.R. Marshall Bioorg. Med. Chem. Lett. 5 1995 2643 2648
22. A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, and A. Guagliardi SIR97: a new tool for crystal structure determination and refinement J. Appl. Crystallogr. 32 1999 115 119
23. G.M. Sheldrick SHELXL-97 1997 Universität Göttingen Germany
24. M.N. Burnett, C.K. Johnson, (ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations), Oak Ridge National Laboratory Report ORNL-6895, 1996 (Windows version (L.J. Farrugia, Univ. Glasgow) used).