Preparation of optically active succinic acid derivatives. II. Efficient and practical synthesis of KAD-1229

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 2, 1998, Pages 337-340

  Yamaguchi, Toshiaki ^a   Yanagi, Takashi ^a   Hokari, Hiroshi ^a   Mukaiyama, Yuko ^a   Kamijo, Tetsuhide ^a   Yamamoto, Iwao ^b  

^a KISSEI PHARMACEUTICAL CO LTD   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

(2S) 2 benzyl 3 (cis hexahydroisoindolin 2 ylcarbonyl)propionic acid; (S) 2 benzylsuccinic acid; KAD 1229; Potent hypoglycemic effect

Indexed keywords

AMINE; BENZYLSUCCINIC ACID; ESTER; HEXAHYDROISOINDOLINE; MITIGLINIDE; SUCCINIC ACID; SUCCINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; HYPOGLYCEMIA; OPTICAL ROTATION;

EID: 0031915118     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.337     Document Type: Article

References (17)

1. Yamaguchi T., Yanagi T., Hokari H., Mukaiyama Y., Kamijo T., Yamamoto I., Chem. Pharm. Bull., 45, 1518-1520 (1997).
2. a) Ohnota H., Koizumi T., Tsutsumi N., Kobayashi M., Inoue S., Sato S., J. Pharmacol. Exp. Ther., 269, 489-495 (1994);
3. b) Mogami H., Shibata H., Nobusawa R., Ohnota H., Sato S., Miyazaki J., Kojima I., Eur. J. Pharmacol. Mol. Pharmacol. Sect., 269, 293-298 (1994);
4. c) Ohnota H., Kobayashi M., Koizumi T., Katsuno K., Sato F., Azisawa T., Biochem. Pharmacol., 49, 165-171 (1995);
5. d) Ohnota H., Koizumi T., Kobayashi M., Momose Y., Sato F., Can. J. Physiol. Pharmacol., 73, 1-6 (1995);
6. e) Kinukawa M., Ohnota H., Azisawa T., Br. J. Pharmacol., 117, 1702-1706 (1996);
7. f) Ohnota H., Kitamura T., Kinukawa M., Hamano S., Shibata N., Miyata H., Ujiie A., Jpn. J. Pharmacol., 71, 315-323 (1996).
8. a) Rice L. M., Grogan C. H., J. Org. Chem., 20, 1687-1694 (1955);
9. b) Otzenberger R. D., Lipkowitz K. B., Mundy B. P., J. Org. Chem., 39, 319-321 (1974).
10. a) Kawano H., Ishii Y., Ikariya T., Saburi M., Yoshikawa S., Uchida Y., Kumobayashi H., Tetrahedron Lett., 28, 1905-1908 (1987);
11. b) Morimoto T., Chiba M., Achiwa K., ibid., 30, 735-738 (1989);
12. c) Jendralla H., ibid., 32, 3671-3672 (1991);
13. d) Saburi M., Takeuchi H., Ogasawara M., Tsukahara T., Ishii Y., Ikariya T., Takahashi T., Uchida Y., J. Organomet. Chem., 428, 155-167 (1992);
14. d) Shao L., Takeuchi K., Ikemoto M., Kawai T., Ogasawara M., Takeuchi H., Kawano H., Saburi M., ibid., 435, 133-147 (1992);
15. e) Jendralla H., Henning R., Seuring B., Herchen J., Kultizscher B., Wunner J., Synlett, 1992, 155-157.
16. Hashimoto N., Aoyama T., Shioiri T., Chem. Pharm. Bull., 29, 1475-1478 (1981).
17. Ito Y., Kamijo T., Harada H., Matsuda F., Terashima S., Tetrahedron Lett., 31, 2731-2734 (1990).