Practical synthesis of BILA 2157 BS, a potent and orally active renin inhibitor: Use of an enzyme-catalyzed hydrolysis for the preparation of homochiral succinic acid derivatives

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6622-6634

  Beaulieu, Pierre L ^a   Gillard, James ^a   Bailey, Murray ^a   Beaulieu, Christian ^a   Duceppe, Jean Simon ^a   Lavallée, Pierre ^a   Wernic, Dominik ^a  

^a BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BILA 2157 BS; RENIN INHIBITOR; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DRUG HYDROLYSIS; DRUG HYDROXYLATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032885570     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990321x     Document Type: Article

References (36)

1. Greenlee, W. J. Med. Res. Rev. 1990, 10, 173.
2. Rosenberg, S. H. Renin Inhibitors. In Progress in Medicinal Chemistry; Ellis, G. P., Luscombe, D. K., Eds.; Elsevier: New York, 1995; Vol. 32, p 32.
3. 1,2
4. Most notable are nonpeptide AII receptor antagonists such as losartan; see, for example: (a) Buchholz, R. A.; Lefker, B. A.; Ravi Kiron, M. A. Ann. Rep. Med. Chem. 1993, 28, 69.
5. (b) Greenlee, W. J.; Siegl, P. K. S. Ann. Rep. Med. Chem. 1982, 27, 59.
6. Boger, J. Ann. Rep. Med. Chem. 1985, 20, 257.
7. Simoneau, B.; Lavallée, P.; Anderson, P. C.; Bailey, M.; Bantle, G.; Berthiaume, S.; Chabot, C.; Fazal, G.; Halmos, T.; Ogilvie, W.; Poupart, M.-A.; Thavonekham, B.; Xin, Z.; Thibeault, D.; Bolger, G.; Panzenbeck, M.; Winquist, R.; Jung, G. L. Bioorg. Med. Chem. 1999, 7, 489.
8. Beaulieu, P. L.; Lavallée, P.; Abraham, A.; Anderson, P. C.; Boucher, C.; Bousquet, Y.; Duceppe, J.-S.; Gillard, J.; Gorys, V.; Grand-Maître, C.; Grenier, L.; Guindon, Y.; Guse, I.; Plamondon, L.; Soucy, F.; Valois, S.; Wernic, D.; Yoakim, C. J. Org. Chem. 1997, 62, 3440.
9. Luly, J. R.; BaMaung, N.; Soderquist, J.; Fung, A. K. L.; Stein, H.; Kleinert, H. D.; Marcotte, P. A.; Egan, D. A.; Bopp, B.; Merits, I.; Bolis, G.; Greer, J.; Perun, T. J.; Plattner, J. J. J. Med. Chem. 1988, 31, 2264.
10. (a) Morton, H. E.; Leanna, M. R. Tetrahedron Lett. 1993, 34, 4481.
11. (b) Leanna, M. R.; Morton, H. E. Tetrahedron Lett. 1993, 34, 4485.
12. Simoneau, B.; Lavallée, P.; Bailey, M.; Duceppe, J.-S.; Grand-Maître, C.; Grenier, L.; Ogilvie, W. W.; Poupart, M.-A.; Thavonekham, B. Can. J. Chem., in press.
13. BILA 2157 BS exists in solution as a mixture of several rotamers, due to the presence of two tertiary amide functionalities. Coupled to a high peptidic content, this phenomena confers amorphous physical properties to the molecules which have not allowed purification of the inhibitor by crystallization.
14. (a) Luly, J. R.; Hsiao, C.-N.; BaMaung, N.; Plattner, J. J. J. Org. Chem. 1988, 53, 6109.
15. (b) Rosenberg, S. H.; Spina, K. P.; Woods, K. W.; Polakowski, J.; Martin, D. L.; Yao, Z.; Stein, H. H.; Cohen, J.; Barlow, J. L.; Egan, D. A.; Tricarico, A.; Baker, W. R.; Kleinert, H. D. J. Med. Chem. 1993, 36, 449.
16. For other approaches to the synthesis of 4, including scale-up of a modified cyanohydrin route, see: (c) Schwindt, M. A.; Belmont, D. T.; Carlson, M.; Franklin, L. C.; Hendrickson, V. S.; Karrick, G. L.; Poe, R. W.; Sobieray, D. M.; Van De Vusse, J. J. Org. Chem. 1996, 61, 9564 and references therein.
17. Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron: Asymmetry 1994, 5, 625.
18. (a) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in industry. The commercial manufacture and applications of optically active compounds; John Wiley: New York, 1992.
19. (b) Collins, A. N.; Sheldrake, G. N.; Crosby, J. Chirality in industry II. Developments in the manufacture and applications of optically active compounds; John Wiley: New York, 1997.
20. (a) Bailey, M. D. U.S. Patent 5 808 085, 1998.
21. (b) Bailey, M.; Adamson, D.; Halmos, T.; Grand-Maître, C. Tetrahedron: Asymmetry 1999, in press.
22. Similar enzymatic hydrolysis protocols for succinate derivatives have been reported by other groups: (c) Wirz, B.; Soukup, M. Tetrahedron: Asymmetry 1997, 8, 187.
23. (d) Ozaki, E.; Sakashita, K. Chem. Lett. 1997, 741.
24. (e) Guibé-Jampel, E.; Rousseau, G.; Salaün, J. J. Chem. Soc., Chem. Commun. 1987, 1080.
25. Singh, R. K. Synthesis 1986, 54.
26. (a) Enzymes in synthetic organic chemistry; Wong, C. H., Whitesides, G. M., Eds.; Elsevier Science, Inc.: New York, 1994.
27. (b) Enzyme catalysis in organic synthesis. A comprehensive handbook; Drauz, K., Waldmann, H., Eds.; VCH Publishers: New York, 1995; Vol. 1.
28. (a) Alcalase is a crude enzyme preparation whose main component (Subtilisin A, Subtilisin Carlsberg) is a serine endopeptidase. The crude Alcalase 2.4 L enzyme preparation is available in bulk from Novo Nordisk Biochem North America, Inc., Franklinton, NC 27525.
29. (b) Since the extent of conversion for these reactions was not accurately measured, only approximate E values can be determined for these two substrates; see: Chen, C.-H.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
30. (a) Schröder, M. Chem. Rev. 1980, 80, 187.
31. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768.
32. 1 double bond underwent attack (presumably from the least hindered side) and a single isomer of the bromo derivative, with the relative stereochemistries shown below, was isolated (tentative structure based on MS and NMR). Formula represented
33. Bodansky, M. In Principles of Peptide Synthesis; Springler-Verlag: New York, 1984.
34. The authors have deposited atomic coordinates for this structure with the Cambridge Cristallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.
35. Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927.
36. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.