Synthesis of LIAZAL(TM), a retinoic acid metabolism blocking agent (RAMBA) with potential clinical applications in oncology and dermatology

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 3, 1998, Pages 267-272

  Freyne, E ^a   Raeymaekers, A ^a   Venet, M ^b   Sanz, G ^b   Wouters, W ^a   De Coster, R ^a   Van Wauwe, J ^a  

^a JANSSEN RESEARCH FOUNDATION   (Belgium)

^b Janssen Cilag ^*  (France)

Author keywords

[No Author keywords available]

Indexed keywords

LIAROZOLE FUMARATE; RETINOIC ACID; ANTINEOPLASTIC AGENT; CYTOCHROME P450; DERMATOLOGICAL AGENT; ENZYME INHIBITOR; IMIDAZOLE DERIVATIVE; LIAROZOLE; RETINOIC ACID 4 HYDROXYLASE; RETINOIC ACID 4-HYDROXYLASE;

ANIMAL TISSUE; ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; HAMSTER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; TISSUE LEVEL; VITAMIN METABOLISM; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; METABOLISM; SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CYTOCHROME P-450 ENZYME SYSTEM; DERMATOLOGIC AGENTS; ENZYME INHIBITORS; HUMANS; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; RATS; TRETINOIN;

EID: 0032477599     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00004-3     Document Type: Article

References (21)

1. 1. De Luca, L.M. FASEB J. 1991, 5, 2924.
2. 2. Lotan, R. FASEB J. 1996, 10, 1031.
3. 3. Cunliffe, W.J. Biochem. Soc. Trans. 1986, 14, 943.
4. 4. Griffiths, C.E.M.; Fischer, G.J.; Finkel, L.J.; Voorhees, J.J. Brit. J. Dermatol. 1992, 127, 21.
5. 5. Muindi, J.; Frankel, S.R.; Miller, W.H. Jr.; Jakubowski, A.; Scheinberg, D.A.; Young, C.W.; Dmitrovsky, E.; Warrell, R.P. Jr. Blood 1992, 79, 299.
6. 6. Van Wauwe, J.; Coene, M.-C.; Cools, W.; Goossens, J.; Lauwers, W.; Lejeune, L.; Van Hove, C.; Van Nyen, G. Biochem. Pharmacol. 1994, 47, 737.
7. 7. Napoli, J.L. FASEB J. 1996, 10, 993.
8. 8. White, J.A.; Guo, Y.D.; Baetz, K.; Beckett-Jones, B.; Bonasoro, J.; Hsu, K.E.; Dilworth, F.J.; Jones, G.; Petkovich, M. J. Biol. Chem. 1996, 271, 29922.
9. 9. Vanden Bossche, H.; Willemsens, G. Retinoids : 10 years on ; Saurat, J.H., Ed. ; Karger : Basle, 1990, 79.
10. 10. Wouters, W.; Van Dun, J.; Dillen, A.; Coene, M.-C.; Cools, W.; De Coster, R. Cancer Res. 1992, 52, 2841.
11. 11. Krekels, M.D.W.G.; Zimmerman, J.; Janssens, B.; Van Ginckel, R.; Van Hove, C.; Coene, M.-C.; Wouters, W. Prostate 1995, 29, 317.
12. 12. Van Wauwe, J.P.; Coene, M.C.; Goossens, J.; Van Nijen, G.; Cools, W.; Lauwers, W. J. Pharmacol. Exp. Ther. 1988, 245, 718.
13. 13. Raeymaekers, A.H.M.; Freyne, E.J.E.; Sanz, G.C. Novel (1H-imidazol-1-ylmethyl) substituted benzimidazole derivatives, EP-0,260,744.
14. 14. Nishida, S. J. Org. Chem. 1967, 32, 2697.
15. 15. Van Wauwe, J.P.; Van Nyen, G.; Coene, M.-C.; Stoppie, P.; Cools, W.; Goossens, J.; Borghgraef, P.; Janssen, P.A.J. J. Pharmacol. Exp. Ther. 1992, 261, 773.
16. 16. Vanden Bossche, H. J. Steroid Biochem. Mol. Biol. 1992, 43, 1003.
17. 17. Vanden Bossche, H.; Willemsens, G.; Schreuders, H.; Coene, M.-C.; Van Hove, C.; Cools, W. In Human cells in in vitro pharmaco-toxicology. Present status in Europe ; Rogiers, V.; Sonck, W.; Shephard, E.; Vercruysse, A.; eds. VUB Press, Brussels, 1993, 61.
18. 18. Krekels, M.D.W.G.; Verhoeven, A.; van Dun, J.; Cools, W.; Van Hove, C.; Dillen, L.; Coene, M.-C.; Wouters, W. Br. J. Cancer 1997, 75, 1098.
19. 19. Van Heusden, J.; Borgers, M.; Ramaekers, F.; Xhonneux, B.; Wouters, W.; De Coster, R.; Smets, G. Eur. J. Cell Biol. 1996, 71, 89.
20. 20. Smets, G.; Van Ginckel, R.; Daneels, G.; Moeremans, M.; Van Wauwe, J.; Coene, M.-C.; Ramaekers, F.C.S.; Scalken, J.A.; Borgers, M.; De Coster, R. Prostate (N.Y.) 1995, 27, 129.
21. 21. Dijkman, G.A.; Reindert, J.A.; Van Moorselaar, R.J.A.; Van Ginckel, R.; Van Stratum, P.; Wouters, L.; Debruyne, F.M.J.; Schalken, J.A.; De Coster, R. J. Urology 1994, 151, 217.