Studies on Pyrrolidinones. Synthesis of Some Bioisosteres of 3,3,5-Trimethylcyclohexyl Pyroglutamate

Journal of Heterocyclic Chemistry

Volumn 34, Issue 1, 1997, Pages 279-283

  Rigo, Benoît ^a   Laruelle, Claude ^b  

^a Ecole des Hautes Etudes d'Ingenieur   (France)

^b CL Pharma   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345717410     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340142     Document Type: Article

References (22)

1. Panmedica S.A., French Patent 2,572,399 (1986); Chem. Abstr., 105, 227298p (1986).
2. Panmedica S.A., French Patent 2,572,399 (1986); Chem. Abstr., 105, 227298p (1986).
3. Panmedica S.A., European Patent 261,017 (1988); Chem. Abstr., 110, 213345t (1989); T. Clerc, M. Jomier, M. Chautan, H. Portugal, M. Senft, A. M. Pauli, C. Laruelle, O. Morel, H. Lafont and F. Chanussot, Eur. J. Pharmacol., 235, 59 (1993); C. Esnault-Dupuy, H. Lafont, F. Chanussot, M. Chautan, J. Hauton and C. Laruelle in Liver cells and Drugs, A. Guillouzo ed, INSERM/John Libbey-Eurotext Ltd., Paris, 1988, pp 99-102; T. Clerc, V. Sharra, N. Diaconescu, H. Lafont, G. Jadot, C. Laruelle and F. Chanussot, Brit. J. Pharm., 114, 624 (1995).
4. Panmedica S.A., European Patent 261,017 (1988); Chem. Abstr., 110, 213345t (1989); T. Clerc, M. Jomier, M. Chautan, H. Portugal, M. Senft, A. M. Pauli, C. Laruelle, O. Morel, H. Lafont and F. Chanussot, Eur. J. Pharmacol., 235, 59 (1993); C. Esnault-Dupuy, H. Lafont, F. Chanussot, M. Chautan, J. Hauton and C. Laruelle in Liver cells and Drugs, A. Guillouzo ed, INSERM/John Libbey-Eurotext Ltd., Paris, 1988, pp 99-102; T. Clerc, V. Sharra, N. Diaconescu, H. Lafont, G. Jadot, C. Laruelle and F. Chanussot, Brit. J. Pharm., 114, 624 (1995).
5. Panmedica S.A., European Patent 261,017 (1988); Chem. Abstr., 110, 213345t (1989); T. Clerc, M. Jomier, M. Chautan, H. Portugal, M. Senft, A. M. Pauli, C. Laruelle, O. Morel, H. Lafont and F. Chanussot, Eur. J. Pharmacol., 235, 59 (1993); C. Esnault-Dupuy, H. Lafont, F. Chanussot, M. Chautan, J. Hauton and C. Laruelle in Liver cells and Drugs, A. Guillouzo ed, INSERM/John Libbey-Eurotext Ltd., Paris, 1988, pp 99-102; T. Clerc, V. Sharra, N. Diaconescu, H. Lafont, G. Jadot, C. Laruelle and F. Chanussot, Brit. J. Pharm., 114, 624 (1995).
6. Panmedica S.A., European Patent 261,017 (1988); Chem. Abstr., 110, 213345t (1989); T. Clerc, M. Jomier, M. Chautan, H. Portugal, M. Senft, A. M. Pauli, C. Laruelle, O. Morel, H. Lafont and F. Chanussot, Eur. J. Pharmacol., 235, 59 (1993); C. Esnault-Dupuy, H. Lafont, F. Chanussot, M. Chautan, J. Hauton and C. Laruelle in Liver cells and Drugs, A. Guillouzo ed, INSERM/John Libbey-Eurotext Ltd., Paris, 1988, pp 99-102; T. Clerc, V. Sharra, N. Diaconescu, H. Lafont, G. Jadot, C. Laruelle and F. Chanussot, Brit. J. Pharm., 114, 624 (1995).
7. Panmedica S.A., European Patent 261,017 (1988); Chem. Abstr., 110, 213345t (1989); T. Clerc, M. Jomier, M. Chautan, H. Portugal, M. Senft, A. M. Pauli, C. Laruelle, O. Morel, H. Lafont and F. Chanussot, Eur. J. Pharmacol., 235, 59 (1993); C. Esnault-Dupuy, H. Lafont, F. Chanussot, M. Chautan, J. Hauton and C. Laruelle in Liver cells and Drugs, A. Guillouzo ed, INSERM/John Libbey-Eurotext Ltd., Paris, 1988, pp 99-102; T. Clerc, V. Sharra, N. Diaconescu, H. Lafont, G. Jadot, C. Laruelle and F. Chanussot, Brit. J. Pharm., 114, 624 (1995).
8. Unilever N.V., German Patent 2,707,814 (1977); Chem. Abstr., 87, 189314r (1977).
9. Unilever N.V., German Patent 2,707,814 (1977); Chem. Abstr., 87, 189314r (1977).
10. Ferlux S.A., French Patent 2,273,533 (1974); Chem. Abstr., 85, 32835x (1976).
11. Ferlux S.A., French Patent 2,273,533 (1974); Chem. Abstr., 85, 32835x (1976).
12. E. R. Wagner, R. G. Dull, L. G. Mueller, B. J. Allen, A. A. Renzi, D. J. Rytter, J. W. Barnhart and C. Byers, J. Med. Chem., 20, 1007 (1977).
13. B. Rigo, C. Lespagnol and M. Pauly, J. Heterocyclic Chem., 25, 49 (1988) and references cited therein.
14. N. Kolocouris and B. Rigo, Chim. Chronika, New Series, 11, 309 (1982).
15. B. Rigo and N. Kolocouris, J. Heterocyclic Chem., 20, 893 (1983).
16. B. Rigo, C. Lespagnol and M. Pauly, J. Heterocyclic Chem., 25, 59 (1988); B. Rigo, A. Kolocouris and N. Kolocouris, J. Heterocyclic Chem., 32, 1489 (1995); B. Rigo, B. Erb, S. El Ghammarti, P. Gautret and D. Couturier, J. Heterocyclic Chem., 32, 1599 (1995).
17. B. Rigo, C. Lespagnol and M. Pauly, J. Heterocyclic Chem., 25, 59 (1988); B. Rigo, A. Kolocouris and N. Kolocouris, J. Heterocyclic Chem., 32, 1489 (1995); B. Rigo, B. Erb, S. El Ghammarti, P. Gautret and D. Couturier, J. Heterocyclic Chem., 32, 1599 (1995).
18. B. Rigo, C. Lespagnol and M. Pauly, J. Heterocyclic Chem., 25, 59 (1988); B. Rigo, A. Kolocouris and N. Kolocouris, J. Heterocyclic Chem., 32, 1489 (1995); B. Rigo, B. Erb, S. El Ghammarti, P. Gautret and D. Couturier, J. Heterocyclic Chem., 32, 1599 (1995).
19. P. Cauliez, B. Rigo, D. Passeur and D. Couturier, J. Heterocyclic Chem., 28, 1143(1991).
20. For related Mannich reactions, see: B. Rigo, E. Fossaert, J. de Quillacq and N. Kolocouris, J. Heterocyclic Chem., 21, 1381 (1984); B. Rigo, J. de Quillacq, E. Fossaert and N. Kolocouris, J. Heterocyclic Chem., 21, 1393 (1984).
21. For related Mannich reactions, see: B. Rigo, E. Fossaert, J. de Quillacq and N. Kolocouris, J. Heterocyclic Chem., 21, 1381 (1984); B. Rigo, J. de Quillacq, E. Fossaert and N. Kolocouris, J. Heterocyclic Chem., 21, 1393 (1984).
22. In this test, the ratio of serum heparin precipitating lipoproteins (HPL) to that obtained for serum cholesterol is calculated. Reduction in the HPL/cholesterol ratio below 0.92 indicates a decrease in atherogenic low-density betalipoproteins and/or possible increase in HDL.