New nonsteroidal steroid 5α-reductase inhibitors. Syntheses and structure-activity studies on carboxamide phenylalkyl-substituted pyridones and piperidones

Archiv der Pharmazie

Volumn 333, Issue 5, 2000, Pages 145-153

  Hartmann, Rolf W ^a   Reichert, Martin ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

3 and 5 substituted 1 methyl 2 pyridones; 3 and 5 substituted 1 methyl 2 piperidones; Nonsteroidal inhibitors; Rat and human steroid 5 reductase

Indexed keywords

8 CHLORO 1,2,3,4,4A,5,6,10B OCTAHYDRO 4 METHYLBENZO[F]QUINOLIN 3(2H) ONE; ANDROSTANOLONE; ETHYL 4 (1 METHYL 2 OXOPIPERID 5 YL)BENZOIC ACID; FINASTERIDE; N,N BIS(1 METHYLETHYL) 4 [3 (1,2 DIHYDRO 1 METHYL 2 OXOPYRID 5 YL)PROPYL]BENZAMIDE; PIPERIDONE DERIVATIVE; PYRIDONE DERIVATIVE; STEROID 5ALPHA REDUCTASE; STEROID 5ALPHA REDUCTASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN TISSUE; MALE; NONHUMAN; PRIORITY JOURNAL; PROSTATE HYPERTROPHY; RAT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; ENZYME INHIBITORS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MOLECULAR STRUCTURE; PIPERIDONES; PROSTATE; PROSTATIC HYPERPLASIA; PYRIDONES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; TESTOSTERONE; TESTOSTERONE 5-ALPHA-REDUCTASE;

EID: 0034091406     PISSN: 03656233     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-4184(20005)333:5<145::AID-ARDP145>3.0.CO;2-Q     Document Type: Article

References (30)

1. R.J. Thurlow, Emerging Drugs 1998, 3, 225-246.
2. B. Kenny, S. Ballard, J. Blagg, D. Fox, J. Med. Chem. 1997, 40, 1293-1315.
3. S. Andersson, D.W. Russell, Proc. Natl. Acad. Sci. 1990, 87, 3640-3644.
4. S. Andersson, D.M. Berman, E.P. Jenkins, D.W. Russel, Nature 1991, 554, 159-161.
5. X. Li, C. Chen, S.M. Singh, F. Labrie, Steroids 1995, 60, 430-441.
6. M.J. Sharp, F.G. Fang, Bioorg. Med. Chem. Lett. 1998, 8, 3291-3294.
7. A. Guarna, E.G. Occhiato, G. Danza, A. Conti, M. Serio, Steroids 1998, 65, 355-361.
8. X.S. Fei, W.S. Tian, Q.Y. Chen, Bioorg. Med. Chem.Lett. 1997, 7, 3113-3118.
9. S.V. Frye, Curr. Pharm. Des. 1996, 2, 59-84.
10. Y.Z. Ling, J.S. Li, K. Kato, Y. Liu, X. Wang, G.T. Klus, K. Marat, J.P. Nnane, A.M. Brodie, Bioorg. Med. Chem. 1998, 6, 1683-1693.
11. G.H. Rasmusson, G.F. Reynolds, N.G. Steinberg, E. Walton, G.F. Patel, T. Liang, M.A. Cascieri, A.H. Cheung, J.R. Brooks, C. Berman, J. Med. Chem. 1986, 29, 2298-2315.
12. D.H. Peters, E.M. Sorkin, Drugs 1993, 46, 177-208.
13. M.J. Marberger, Urol. 1998, 51, 677-686.
14. M.C. Uygur, E. Gür. A.I. Arik, U. Altug, D. Erol, Androl. 1998, 30, 5-10.
15. A. Guarna, E.G. Occhiato, D. Scarpi, R. Tsai, A. Comerci, R. Mancina, M. Serio, Bioorg. Med. Chem. Lett. 1998, 8, 2871-2876.
16. H. Takami, N. Kishibayashi, A. Ishi, T. Kumazawa, Bioorg. Med. Chem. 1998, 6, 2441-2448.
17. E.C.R. Smith, L.A. McQuaid, R.L. Goode, A.M. McNulty, B.L. Neubauer, V.P. Rocco, J.E. Audia, Bioorg. Med. Chem.Lett. 1998, 8, 395-398.
18. K.S. Hirsch, C.D. Jones, J.E. Audia, S. Andersson, L.A. McQuaid, N.B. Stamm, B.L. Neubauer, P. Pennington, R.E. Toomey, D.W. Russel, Proc. Natl. Acad. Sci. 1993, 90, 5277-5281.
19. C.D. Jones, J.E. Audia, D.E. Lawhorn, L.A. McQuaid, B.L. Neubauer, A.J. Pike, P.A. Pennigton, N.B. Stamm, R.E. Toomey, K.S. Hirsch, J. Med. Chem. 1993, 36, 421-423.
20. R.W. Hartmann, M. Reichert, S. Göhring, Eur. J. Med. Chem. 1994, 29, 807-817.
21. L. Kattner, S. Göhring, R.W. Hartmann, Arch. Pharm. Pharm. Med. Chem. 1995, 328, 239-245.
22. E. Baston, R.W. Hartmann, Bioorg. Med. Chem. Lett. 1999, 9, 1601-1606.
23. E. Baston, A. Palusczak, R.W. Hartmann, Eur. J. Med. Chem. 2000, 35, in press.
24. F. Picard, E. Baston, W. Reichert, R.W. Hartmann, Bioorg. Med. Chem. 2000, in press.
25. M. Terashima, H. Kakimi, M. Ishikura, K. Kamata, Chem. Pharm. Bull. 1983, 31, 4573-4577.
26. M. Ishikura, M. Kamada, M. Terashima, Heterocycles 1984, 22, 265-268.
27. H. Tomisawa, R. Fujita, H. Hongo, H. Kato, Chem. Pharm. Bull. 1974, 22, 2091-2096.
28. G.W. Gribble, R.M. Leese, Synthesis 1977, 172-176.
29. T. Liang, M.A. Cascieri, A.H. Cheung, G.F. Reynolds, G.H. Rasmusson, Endocrinology 1985, 117, 571-579.
30. S.J. Cook, N.C. Rawlings, R.J. Kennedy, Steroids 1982, 40, 369-380.