Novel potassium channel openers. Part 4: Transformation of the 1,4- benzoxazine skeleton into 1,4-benzothiazine, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroquinoxaline, indoline, and 1,5-benzoxazepine

Bioorganic and Medicinal Chemistry

Volumn 8, Issue 2, 2000, Pages 393-404

  Matsumoto, Yuzo ^a,b   Tsuzuki, Ryuji ^a   Matsuhisa, Akira ^a   Yoden, Toru ^a   Yamagiwa, Yoko ^a   Yanagisawa, Isao ^a   Shibanuma, Tadao ^a   Nohira, Hiroyuki ^b  

^a ASTELLAS PHARMA INC   (Japan)

^b SAITAMA UNIVERSITY   (Japan)

Author keywords

Antihypertension; Cardiovascular activity; Potassium channel openers; Vasodilators

Indexed keywords

1,2,3,4 TETRAHYDROQUINOLINE DERIVATIVE; BENZOTHIAZINE DERIVATIVE; CROMAKALIM; OXAZEPINE DERIVATIVE; POTASSIUM CHANNEL STIMULATING AGENT; QUINOXALINE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ANTIHYPERTENSIVE ACTIVITY; ARTERY CONSTRICTION; ARTICLE; DOG; DRUG SYNTHESIS; DRUG TRANSFORMATION; FEMALE; MALE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; DOGS; FEMALE; MALE; POTASSIUM CHANNELS;

ANIMALIA; CANIS FAMILIARIS;

EID: 0033999086     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00292-8     Document Type: Article

References (35)

1. Gopalakrishnan M., Janis R.A., Triggle D.J. Drug Dev. Res. 28:1993;95.
2. Ulrich Q. Trends Pharmacol. Sci. 14:1993;332.
3. For reviews of potassium channel activators, Cook N. S. Trends Pharmacol. Sci. 1988, 9, 21.
4. Robertson, D. W.; Steinberg, M. I. Ann. Reports Med. Chem. 1989, 91-100.
5. Quast U., Cook N.S. Trends Pharmacol. Sci. 10:1989;431.
6. Robertson D.W., Steinberg M.I. J. Med. Chem. 33:1990;1529.
7. Edwards G., Weston A.H. Trends Pharmacol. Sci. 11:1990;417.
8. Evans, J. M.; Longman, S. D. Ann. Reports Med. Chem. 1991, 73.
9. Longman S.D., Hamilton T.C. Med. Res. Rev. 12:1992;73.
10. Gopalakrishnan M., Janis R.A., Triggle D.J. Drug Devel. Res. 28:1993;95.
11. Atwal K.S. Drug. Devel. Res. 33:1994;250.
12. Evans J.M., Taylor S.G. Prog. Med. Chem. 31:1994;411.
13. Pirotte B., Fontaine J., Lebrun P. Cur. Med. Chem. 2:1995;573.
14. Raeburn D., Karlson J-A. Prog. Drug. Res. 37:1991;161.
15. Edwards G., Henshaw M., Miller M., Weston A.H. Br. J. Pharmacol. 102:1991;679.
16. Buhl A.E., Waldon D.J., Conrad S.J., Mulholland M.J., Shull K.L., Kubicek M.F., Johnson G.A., Brunden M.N., Stefanski K.J., Stehle R.G., Gadwood R.C., Kamdar B.V., Thomasco L.M., Schostarez H.J., Schwartz T.M., Diani A.R. J. Invest. Dermatol. 98:1992;315.
17. Escande D., Cavero I. Trends Pharmacol. Sci. 13:1992;269.
18. Hamilton T.C., Beerahee A., Moen J.S., Price P.K., Ramji J.V., Clapham J.C. Cardiovascular Drug Rev. 11:1993;199.
19. Ashwood V.A., Buckingham R.E., Cassidy F., Evans J.M., Faruk E.A., Hamilton T.C., Nash D.J., Stemp G., Willcocks K. J. Med. Chem. 29:1986;2194.
20. Peterson H.J., Nielsen C.K., Martelli E.A. J. Med. Chem. 21:1978;773.
21. Sakai K. Jpn. J. Pharmacol. 30:1980;881.
22. Brown T.J., Chapman R.F., Cook D.C., Hart T.W., Mclay I.M., Jordan R., Mason J.S., Palfreyman M.N., Walsh R.J.A., Withnall M.T., Aloup J.C., Cavero I., Farge D., James C., Mondot S. J. Med. Chem. 35:1992;3613.
23. Price C.C., Stacy G.W. J. Am. Chem. Soc. 68:1946;498.
24. Ward, E. R.; Jonson, C. D.; Hawkins, J. G. J. Chem. Soc. 1960, 894.
25. Evans A.R., Martin R., Taylor G.A., Yap C.H.M. J. Chem. Soc. Perkin Trans. 1. 7:1987;1635.
26. Lai, J. T. Synthesis 1982, 71.
27. Ainsworth, D. P.; Suschitzky H. J. Chem. Soc. (c), 1966, 111.
28. Holck, J. P.; Kampe, W.; Mertens, A.; Muller, B.; Strein, K.; Sponer, G. Ger. Offen. DE3417643, 1985 (Chem. Abst. 1986, 104, 186410c).
29. Sam, J.; Valentine, J. L.; Aboul-enein, M. N. J. Pharm. Sci. 1971, 60, 1370.
30. Uchida, Y.; Sugimoto, T. Myakkangaku. 1984, 24, 133.
31. Buckle, D. R.; Eggleston, D. S.; Houge-Frydrych, C. S. S.; Pinto, I. L.; Readshaw, S. A.; Smith, D. G.; Webster, R. A. B. J. Chem. Soc. Perkin Trans. 1 1991, 2763.
32. Tripos, Inc., 1699 S. Hanley Road St. Louis, MO 63144-2913, USA.
33. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
34. For previous paper in this series see: Part 1, Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Takayama, K.; Yoden, T.; Uchida, W.; Asano, M.; Fujita, S.; Yanagisawa, I.; Fujikura, T. Chem. Pharm. Bull. 1996, 44, 103; Part 2, Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Masuda, N.; Yamagiwa, Y.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Chem. Pharm. Bull. 1999, 47, 971.
35. For previous paper in this series see: Part 1, Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Takayama, K.; Yoden, T.; Uchida, W.; Asano, M.; Fujita, S.; Yanagisawa, I.; Fujikura, T. Chem. Pharm. Bull. 1996, 44, 103; Part 2, Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Masuda, N.; Yamagiwa, Y.; Yanagisawa, I.; Shibanuma, T.; Nohira, H. Chem. Pharm. Bull. 1999, 47, 971.