Synthesis of the optical isomers of 4-[1-(4-tert-butylphenyl)-2- oxopyrrolidine-4-yl]methyloxybenzoic acid (S-2) and their biological evaluation as antilipidemic agent

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 11, 1999, Pages 1549-1554

  Ohno, Tomoyasu ^a   Yano, Shin Go ^a   Yamada, Haruo ^a   Shirasaka, Tetsuhiko ^a   Yamamoto, Akira ^a   Kobayashi, Kimiko ^b   Ogawa, Kazuo ^a  

^a TAIHO PHARMACEUTICAL CO LTD   (Japan)

^b INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Antilipidemic agent; Optical isomer; Pharmacokinetics; S 2E; X ray crystallographic

Indexed keywords

4 [1 (4 TERT BUTYLPHENYL) 2 OXO PYRROLIDINE 4 YL]METHYLOXYBENZOIC ACID; ANTILIPEMIC AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; COLUMN CHROMATOGRAPHY; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG POTENCY; DRUG SYNTHESIS; ENANTIOMER; ISOMER; NONHUMAN; OPTICAL ROTATION; ORAL DRUG ADMINISTRATION; RAT; X RAY CRYSTALLOGRAPHY;

EID: 0033453314     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.1549     Document Type: Article

References (17)

1. This paper is dedicated in memory of Dr. Haruo Yamada(deceased 1997). Part I: Watanabe S., Ogawa K., Ohno T., Yano S., Yamada H., Shirasaka T., Eur. J. Med. Chem., 29, 675-686 (1994).
2. Tsujta T., Kuroda M., Shimada Y., Tanzawa K., Arai M., Kaneko I., Tanaka M., Watanabe Y., Fujii S., Biochim. Biophys. Acta, 877, 50-60 (1986).
3. Hoffman W. F. Alberts A. W., Anderson P. S., Chen J. S., Smith R. L., Willard A. K., J. Med. Chem., 29, 849-852 (1986).
4. a) Manniner V., Tenkanen L., Koskinen P., Huttunen J., Manttari M., Heinonen O. P., Frick M. H., Circulation, 85, 37-45 (1992);
5. b) Idem, ibid., 85, 365-367 (1992);
6. c) Castelli W. P., Am. Heart J., 112, 432-437 (1986);
7. d) Assmann G., Schulte H., Am. J. Cardiol, 70, 733-737 (1992).
8. Okamoto Y., Aburatan R., Hatada K., J. Chromatogr., 389, 95-102 (1987). These chiral columns were purchased from Daicel Chemical Co.
9. Main P., E. Hull S. E., Lessinger L., Germain G., Declercq J. P., Woolson M. M., "MULTAN-78, A System of Computer Programs for the Automatic Solution of Crystal Structures from X-Ray Diffraction Data," Universities of York, England and Louvain, Belgium, 1978.
10. a) White E. H., J. Am. Chem. Soc., 76, 4497-4498 (1954);
11. b) Idem, ibid., 77, 6008-6010 (1955).
12. Kusama H., Nishiyama M., Matsubara Y., Ikeda S., Nippon Yakugaku Zasshi, 92, 181-191 (1988).
13. a) Bortz W. M., Steele L. A., Biochim. Biophys. Acta, 306, 85-94 (1973);
14. b) Endo A., Tsujita Y., Kuroda M., Tanzawa K., ibid., 575, 266-276 (1979).
15. This work was performed by the contracted separation with the Daicel Chemical Co.
16. "International Tables for X-Ray Crystallography," Vol. IV, Birmingham: Kynoch Press, 1974.
17. Sakurai T., Kobayashi K., Rikagaku Kenkyusho Hokoku, 55, 69-77 (1979).