Asymmetric synthesis of (R)-nilvadipine and (S)-NB 818 via regioselective bromination of chiral 1,4-dihydropyridines as a key step and enzymatic resolution of racemic 2-hydroxymethyl-1,4-dihydropyridine derivatives

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 5, 1997, Pages 869-876

  Ebiike, Hirosato ^a   Maruyama, Kaori ^a   Ozawa, Yumi ^a   Yamazaki, Yukiyoshi ^a   Achiwa, Kazuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

1,4 Dihydropyridine; Calcium antagonist; Enzymatic synthesis

Indexed keywords

1,4 DIHYDROPYRIDINE; 2 HYDROXYMETHYL 1,4 DIHYDROPYRIDINE DERIVATIVE; CALCIUM ANTAGONIST; LEMILDIPINE; NILVADIPINE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHIRALITY; DRUG HYDROLYSIS; DRUG SYNTHESIS; ENZYME SYNTHESIS; ESTERIFICATION; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030919105     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.869     Document Type: Article

References (21)

1. Bossert F., Vater W., Med. Res. Rev., 9, 291-769 (1989).
2. Goldmann F., Stoltefuss J., Angew. Chem. Int. Ed. Engl., 30, 1559-1578 (1991).
3. Goldmann F., Stoltefuss J., Born L., J. Med. Chem., 35, 3341-3344 (1992).
4. Sato Y., Okumura K., Shiokawa Y., Chem. Pharm. Bull., 40, 1799-1807 (1992).
5. Nishikibe M., J. Pharmacol. Exp. Ther., 246, 719-725 (1988).
6. Abe H., Katada K., Orita M., Nishikibe M., J. Pharm. Pharmacol., 43, 22-26 (1991).
7. Arrowsmith J. E., Campbell S. F., Cross P. E., Stubbs J. K., Gardiner R. A., Blackburn K. J., J. Med. Chem., 29, 1696-1702 (1986).
8. Alker D., Denton S. M., Tetrahedron, 46, 3693-3696 (1990).
9. Ebiike H., Terao Y., Achiwa K., Tetrahedron Lett., 32, 5805-5808 (1991).
10. Eisner U., Kuthan J., Chem. Rev., 72, 1-42 (1972).
11. Bossert F., Meyer H., Wehinger E., Angew. Chem. Int. Ed. Engl., 20, 762-769 (1981).
12. Lipase AH, lipase PS and CHE were kindly supplied by Amano Pharmaceutical Co., Ltd.
13. Ebiike H., Maruyama K., Achiwa K., Tetrahedron: Asymmetry, 3, 1153-1156 (1992).
14. Yamazaki Y., Ebiike H., Achiwa K., Chem. Pharm. Bull., 42, 1968-1970 (1994).
15. Ebiike H., Ozawa Y., Achiwa K., Hirose Y., Kariya K., Sasaki I., Kurono Y., Heterocycles, 35, 603-606 (1993).
16. Terao Y., Murata M., Achiwa K., Nishio T., Akamatsu M., Kamimura M., Tetrahedron Lett., 29, 5173-5176 (1988).
17. Murata M., Terao Y., Achiwa K., Nishio T., Seto K., Chem. Pharm. Bull., 37, 2670-2672 (1989).
18. Ebiike H., Achiwa K., Tetrahedron: Asymmetry, 5, 1447-1450 (1994).
19. Yamazaki Y., Achiwa K., Heterocycles, 42, 169-171 (1996).
20. Young S. D., Synthesis, 1984, 617-618.
21. Hankovszky O. H., Sár C. P., Hideg K., Jerkovich G., Synthesis, 1991, 91-97.