Nicotinamide derivatives as a new class of gastric (H+/K+)-ATPase inhibitors. II. Synthesis and structure-activity relationships of 2-[(2,4- dimethoxyhenzyl)sulfinyl]-N-(4-pyridinyl)pyridine-3-carboxamides

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 6, 1997, Pages 1027-1038

  Terauchi, Hideo ^a   Tanitame, Akihiko ^a   Tada, Keiko ^a   Nakamura, Keiji ^a   Seto, Yasuhiro ^a   Nishikawa, Yoshinori ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

(H+ K+) ATPase inhibitor; 2 (2,4 dimethoxybenzyl) sulfinyl N (4 pyridinyl)pyridine 3 carboxamide; 7 ethoxycoumarin deethylase; antisecretory activity

Indexed keywords

2 [(2,4 DIMETHOXYBENZYL)SULFINYL] N (2,5 DIMETHYL 4 PYRIDINYL)PYRIDINE 3 CARBOXAMIDE; 2 [(2,4 DIMETHOXYBENZYL)SULFINYL] N (2,6 DIMETHYL 4 PYRIDINYL)PYRIDINE 3 CARBOXAMIDE; 7 ETHOXYCOUMARIN DEETHYLASE; CYTOCHROME P450; HISTAMINE; NICOTINAMIDE DERIVATIVE; OMEPRAZOLE; PROTON PUMP INHIBITOR; PYRIDINE 3 CARBOXAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG COMPETITION; DRUG POTENCY; ENZYME INHIBITION; INHIBITION KINETICS; INTRADUODENAL DRUG ADMINISTRATION; MALE; NONHUMAN; RABBIT; RAT; STOMACH ACID SECRETION; STRUCTURE ACTIVITY RELATION;

EID: 0030814319     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.1027     Document Type: Article

References (36)

1. Part 1 of this series: Terauchi H., Tanitame A., Tada K., Nakamura K., Seto Y., Nishikawa Y., J. Med. Chem., 40, 313-321 (1997).
2. a) Fellenius E., Berglindh T., Sachs G., Olbe L., Elander B., Sjöstrand S-E., Wallmark B., Nature (London), 290, 159-161 (1981);
3. b) Olbe L., Berglindh T., Elander B., Helander H., Fellenius E, Sjöstrand S. E., Sundell G., Wallmark B., Scand. J. Gastroenterol., 14 (Suppl. 55), 131-135 (1979).
4. a) Satoh H., Inatomi N., Nagaya H., Inada I., Nohara A., Nakamura N., Maki Y., J. Pharmacol. Exp. Ther., 248, 806-815 (1989);
5. b) Kubo K., Oda K., Kaneko T., Satoh H., Nohara A., Chem. Pharm. Bull., 38, 2853-2858 (1990).
6. Kohl B., Sturm E., Senn-Bilfinger J., Alexander Simon W., Krüger U., Schaefer H., Rainer G., Figala V., Kelemm K., J. Med. Chem., 35, 1049-1057 (1992).
7. Fujisaki H., Shibata H., Oketani K., Murakami M., Fujimoto M., Wakabayashi T., Yamatsu I., Yamaguchi M., Sakai H., Takeguchi N., Biochem. Pharmacol. 42, 321-328 (1991).
8. Ife R.J., Dyke C. A., Keeling D. J., Meenan E., Meeson M. L., Parsons M. E., Price C. A., Theobald C. J., Underwood A. H., J. Med. Chem., 32, 1970-1977 (1989).
9. a) Figala V., Klemm K., Kohl B., Krüger U., Rainer G., Schaefer H., Senn-Bilfinger J., Sturm E., J. Chem. Soc., Chem. Commun., 1986, 125-127;
10. b) Lindberg P., Nordberg P., Alminger T., Brändström A., Wallmark B., J. Med. Chem., 29, 1327-1329 (1986);
11. c) Sturm E., Krüger U., Senn-Bilfinger J., Figala V., Kelemm K., Koni B., Rainer G., Schaefer H., J. Org. Chem., 52, 4573-4581 (1987);
12. d) Senn-Bilfinger J., Krüger U., Sturm E., Figala V., Klemm K., Kohl B., Rainer G., Schaefer H., Blake T. J., Darkin D. W., Ife R. J., Leach C. A., Mitchell R. C., Pepper E. S., Salter C. J., Viney N. J., Huttner G., Zsolnai L., ibid., 52, 4582-4592 (1987);
13. e) Krüger U., Senn-Bilfinger J., Sturm E., Figala V., Klemm K., Kohl B., Rainer G., Schaefer H., Blake T. J., Darkin D. W., Ife R. J., Leach C. A., Mitchell R. C., Pepper E. S., Salter C. J., Viney N. J., ibid., 55, 4163-4168 (1990).
14. Weidmann K., Herling A. W., Lang H. J., Scheunemann K. H., Rippel R., Nimmesgern H., Scholl T., Bickel M., Metzger H., J. Med. Chem., 35, 438-450 (1992).
15. a) Yamada M., Yura T., Morimoto M., Harada T., Yamada K., Honma Y., Kinoshita M., Sugiura M., J. Med. Chem., 39, 596-604 (1996);
16. b) Kinoshita M., Satoh N., Magaribuchi T., Sugiura M., Tamaki H., Jpn. J. Pharmacol., 61 (Suppl. I), 104 (1993).
17. Nakamura R., Uchiyama K., Ishikawa M., Sekido S., Jpn. J. Pharmacol., 64 (Suppl. I), 280 (1994).
18. a) Yamada S., Goto T., Yamaguchi T., Aihara K., Kogi K., Narita S., Chem. Pharm. Bull., 43, 421-431 (1995);
19. b) Yamaguchi T., Aihara K., Kogi K., Jpn. J. Pharmacol., 58 (Suppl. I), 280 (1992).
20. a) Okabe S., Akimoto Y., Yamasaki S., Kuwahara K., Jpn. J. Pharmacol., 55, 477-491 (1991).
21. Andelstein G. W., Yen C. H., Haack R. A., Yu S., Gulloikson G., Price D. V., Anglin C., Decktor D. L., Tsai H., Keith R. H., J. Med. Chem., 31, 1215-1220 (1988).
22. Uchida M., Chihiro M., Morita S., Kanbe T., Yamashita H., Yamasaki K., Yabuuchi Y., Nakagawa K., Chem. Pharm. Bull., 37, 2109-2116 (1989).
23. Uchida M., Chihiro M., Morita S., Yamashita H., Yamasaki K., Kanbe T., Yabuuchi Y., Nakagawa K., Chem. Pharm. Bull., 38, 1575-1586 (1989).
24. Chenery R. J., Ayrton A., Oldham H. G., Norman S. J., Standring P., Biochem. Pharmacol., 37, 1407-1414 (1988) and references cited therein.
25. Kobayashi Y., Matsuura Y., Kotani E., Iio T., Fukuda T., Aoyagi T., Tobinaga S., Yoshida T., Kuroiwa Y., Biochem. Pharmacol., 43, 2151-2159 (1992).
26. Terauchi H., Tanitame A., Tada K., Nishikawa Y., Heterocycles 43, 1719-1734 (1996).
27. Dabrowski J., Jasiobedzki W., Jaworski T., Medron M., Terpinski J., Pol. Patent 45711 (1962) [Chem. Abstr., 58, 9033c (1963)].
28. Talik Z., Roczniki Chem., 1961, 35, 475-488 [Chem. Abstr., 57, 15066b (1961)].
29. Talik Z., Roczniki Chem., 1961, 35, 475-488 [Chem. Abstr., 57, 15066b (1961)].
30. Walker G. N., Moore M. A., Weaver B. N., J. Org. Chem., 26, 2740-2747 (1961).
31. Itai T., Ogura H., Yakugaku Zasshi, 75, 292-297 (1955).
32. Kato T., Niitsuma T., Chem. Pharm. Bull., 13, 963-968 (1965).
33. Honma Y., Sekine Y., Hashiyama T., Takeda M., Ono Y., Tsuzurahama K., Chem. Pharm. Bull., 30, 4314-4324 (1982).
34. Fryklund J., Wallmark B., Larsson H., Helander H. F., Biochem. Pharmacol., 33, 273-280 (1984).
35. Berglindh T., Heiander H. F., Öbrink K. J., Acta Physiol. Scand., 97, 401-414 (1976).
36. Reiners J. J., Jr., Cantu A. R., Pavone A., Smith S.C., Gardner C. R., Laskin D. L., Anal. Biochem., 188, 317-324 (1990).