Spiro-substituted piperidines as neurokinin receptor antagonists. III. Synthesis of (±)-N-[2-(3,4-dichlorophenyl)-4-(spiro-substituted piperidin- 1'-yl)butyl]-N-methylbenzamides and evaluation of NK1-NK2 dual antagonistic activities

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 10, 1998, Pages 1538-1544

  Kubota, Hirokazu ^a   Kakefuda, Akio ^a   Okamoto, Yoshinori ^a   Fujii, Masahiro ^a   Yamamoto, Osamu ^a   Yamagiwa, Yoko ^a   Orita, Masaya ^a   Ikeda, Ken ^a   Takeuchi, Makoto ^a   Shibanuma, Tadao ^a   Isomura, Yasuo ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

Conformational analysis; NK1 receptor; NK1 NK2 dual antagonist; NK2 receptor; YM 35375; YM 44778

Indexed keywords

N [2 (3,4 DICHLOROPHENYL) 4 (SPIRO[ISOBENZOFURAN 1(3H) 4' PIPERIDIN] 1' YL)BUTYL] N METHYLBENZAMIDE; NEUROKININ; PIPERIDINE DERIVATIVE; SUBSTANCE P; TACHYKININ RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG; YM 44778;

ARTICLE; BINDING AFFINITY; BRONCHOSPASM; DRUG ANTAGONISM; DRUG SYNTHESIS; GUINEA PIG; MAMMAL; MUCUS SECRETION; NONHUMAN; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

EID: 0031740330     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1538     Document Type: Article

References (20)

1. Part I: Kubota H., Fujii M., Ikeda K., Takeuchi M., Shibanuma T., Isomura Y., Chem. Pharm. Bull., 46, 351-354 (1998); part II: Kubota H., Kakefuda A., Nagaoka H., Yamamoto O., Ikeda K., Takeuchi M., Shibanuma T., Isomura Y., Chem. Pharm. Bull., 46, 242-254 (1998).
2. Part I: Kubota H., Fujii M., Ikeda K., Takeuchi M., Shibanuma T., Isomura Y., Chem. Pharm. Bull., 46, 351-354 (1998); part II: Kubota H., Kakefuda A., Nagaoka H., Yamamoto O., Ikeda K., Takeuchi M., Shibanuma T., Isomura Y., Chem. Pharm. Bull., 46, 242-254 (1998).
3. Erspamer V., Trends Neurosci., 4, 267 (1981).
4. Von Euler U. S., Gaddum J. H., J. Physiol., 72, 74-86 (1931); Chang M. M., Leeman S. E., Niall H. D., Nature New Biol., 232, 86-87 (1971).
5. Von Euler U. S., Gaddum J. H., J. Physiol., 72, 74-86 (1931); Chang M. M., Leeman S. E., Niall H. D., Nature New Biol., 232, 86-87 (1971).
6. Kimura S., Okada M., Sugita Y., Kanazawa I., Munekata E., Proc. Jpn. Acad. (B), 59, 101-104 (1983).
7. Nakanishi S., Annu. Rev. Neurosci., 14, 123-136 (1991); Gerard N. P., Bao L., Ping H. X., Gerard C., Regul. Pept., 43, 21-35 (1993).
8. Nakanishi S., Annu. Rev. Neurosci., 14, 123-136 (1991); Gerard N. P., Bao L., Ping H. X., Gerard C., Regul. Pept., 43, 21-35 (1993).
9. Barnes P. J., Lancet, 1, 242-245 (1986); idem, Trends Pharmacol. Sci., 8, 24-27 (1987); idem, Arch. Int. Pharmacodyn., 303, 67-82 (1990); Barnes P. J., Belvisi M. G., Rogers D. F., Trends Pharmacol. Sci., 11, 185-189 (1990).
10. Barnes P. J., Lancet, 1, 242-245 (1986); idem, Trends Pharmacol. Sci., 8, 24-27 (1987); idem, Arch. Int. Pharmacodyn., 303, 67-82 (1990); Barnes P. J., Belvisi M. G., Rogers D. F., Trends Pharmacol. Sci., 11, 185-189 (1990).
11. Barnes P. J., Lancet, 1, 242-245 (1986); idem, Trends Pharmacol. Sci., 8, 24-27 (1987); idem, Arch. Int. Pharmacodyn., 303, 67-82 (1990); Barnes P. J., Belvisi M. G., Rogers D. F., Trends Pharmacol. Sci., 11, 185-189 (1990).
12. Barnes P. J., Lancet, 1, 242-245 (1986); idem, Trends Pharmacol. Sci., 8, 24-27 (1987); idem, Arch. Int. Pharmacodyn., 303, 67-82 (1990); Barnes P. J., Belvisi M. G., Rogers D. F., Trends Pharmacol. Sci., 11, 185-189 (1990).
13. Sekizawa K., Tamaoki J., Graf P. D., Basaum C. B., Borson D. B., Nadel J. A., J. Pharm. Exp. Ther., 243, 1211-1217 (1987).
14. Uchida Y., Nomura A., Ohtsuka M., Hasegawa S., Am. Rev. Respir. Dis., 136, 718-721 (1987).
15. Murai M., Morimoto H., Maeda Y., Kiyotoh S., Nishikawa M., Fujii T., J. Pharm. Exp. Ther., 262, 403-408 (1992).
16. Burkholder T. P., Kudlacz E. M., Le T.-B., Knippenberg R. W., Shatzer S. A., Maynard G. D., Webster M. E., Morgan S. W., Bioorg. Med. Chem. Lett., 6, 951-956 (1996).
17. Burcher E., Buck S. H., Eur. J. Pharmacol., 128, 165-177 (1986).
18. Grant D. M., Cheney B. V., J. Am. Chem. Soc., 89, 5315-5318 (1967).
19. Bax A., Davis D. G., J. Magn. Reson., 63, 207-213 (1985); Kessler H., Griesinger C., Kerssebaum R., Wagner K., Erust R. R., J. Am. Chem. Soc., 109, 607-609 (1987).
20. Bax A., Davis D. G., J. Magn. Reson., 63, 207-213 (1985); Kessler H., Griesinger C., Kerssebaum R., Wagner K., Erust R. R., J. Am. Chem. Soc., 109, 607-609 (1987).