Synthesis and serotonin 2 (5-HT2) receptor antagonist activity of 5- aminoalkyl-substituted pyrrolo [3,2-c]azepines and related compounds

Chemical and Pharmaceutical Bulletin

Volumn 48, Issue 5, 2000, Pages 623-635

  Mizuno, Akira ^a   Ogata, Atsuto ^a   Kamei, Tomoe ^a   Shibata, Makoto ^a   Shimamoto, Tetsuo ^a   Hayashi, Yasuhiro ^a   Nakanishi, Kyoko ^a   Takiguchi, Chikako ^a   Oka, Naomi ^a   Inomata, Norio ^a  

^a SUNTORY LTD   (Japan)

Author keywords

Antiplatelet aggregation; Pyrrolo 3,2 c azepine; Serotonin 2 receptor antagonist; SUN C5174

Indexed keywords

5 [3 [4 (4 FLUOROPHENYL)PIPERAZIN 1 YL]PROPYL] 8 HYDROXY 1 METHYL 1,4,5,6,7,8 HEXAHYDROPYRROLO[3,2 C]AZEPIN 4 ONE; ADENOSINE DIPHOSPHATE; COLLAGEN; PYRROLE DERIVATIVE; SEROTONIN 2 ANTAGONIST; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; GUINEA PIG; HYPERTENSION; LUNG EMBOLISM; MALE; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; THROMBOCYTE AGGREGATION; THROMBOCYTE RICH PLASMA;

EID: 0034073140     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.48.623     Document Type: Article

References (51)

1. a) Fitzgerald D. J., Roy L., Catella F., Fitzgerald G. A., N. Engl. J. Med., 315, 983-989 (1986);
2. b) Fuster V., Steele P. M., Chesebro J. H., J. Am. Coll. Cardiol., 5, 175B-184B (1985);
3. c) Harrison M. J. G., Circulation, 81 (Suppl. 1), 1-20-1-21 (1990).
4. a) Davies M. J., Thomas A. C., Br. Heart J., 53, 363-373 (1985);
5. b) Hamm C. W., Kupper W., Lorenz R. L., Weber P. C., Wober W., J. Am. Coll. Cardiol., 10, 998-1004 (1987).
6. a) van Nueten J. M., Fed. Proc., 42, 223-227 (1983);
7. b) De Clerck, F., David J.-L., Janssen P. A. J., Agents Actions, 12, 388-397 (1982);
8. c) De Clerck, F., Herman A. G., Fed. Proc., 42, 228-232 (1983).
9. a) Vanhoutte P. M., Fed. Proc., 42, 233-237 (1983);
10. b) Cohen M. L., Fuller R. W., Eiley K. S., J. Pharmacol. Exp. Ther., 218, 421-425 (1981);
11. c) De Cree J., Leempoels J., Demoen B., Roels V., Verhaegen H., Agents Actions, 16, 313-317 (1985).
12. a) Sigal S. L., Gellman J., Sarembock I. J., LaVeau P. J., Chen Q. S., Cabin H. S., Ezekowitz M. D., Arterioscler. Thromb., 11, 770-783 (1991);
13. b) Golino P., Piscione F., Willerson J. T., Cappelli-Bigazzi M., Focaccio A., Villari B., Indolfi C., Russolillo E., Condorelli M., Chiariello M., New Eng. J. Med., 324, 641-648 (1991);
14. c) Shimokawa H., Vanhoutte P. M., J. Am. Coll. Cardiol., 17, 1197-1202 (1991);
15. d) Crowley S. T., Dempsey E. C., Horwitz K. B., Horwitz L. D., Circulation, 90, 1908-1918 (1994).
16. a) van de Wal H. J., Wijn P. F., van Lier H. J., Skotnicki S. H., Microcirc. Endothelium Lymphatics, 2, 657-685 (1985);
17. b) Bush L. R., J. Pharmacol. Exp. Ther., 240, 674-682 (1987).
18. a) Fozard J. R., J. Cardiovasc. Pharmacol., 4, 829-838 (1982);
19. b) Cohen M. L., Fuller R. W., Kurz K. D., Hypertension (Dallas), 5, 676-681 (1983).
20. a) Kikumoto R., Hara H., Ninomiya K., Osakabe M., Sugano M., Fukami H., Tamao Y., J. Med. Chem., 33, 1818-1823 (1990);
21. b) Hara H., Shimada H., Kitajima A., Tamao Y., Arzneim. Forsch., 41, 616-620 (1991).
22. Mizuno M., Inomata N., Miya M., Kamei T., Shibata M., Tatsuoka T., Yoshida M., Takiguchi C., Miyazaki T., Chem. Pharm. Bull., 47, 246-256 (1999).
23. a) Shioiri T., Yokoyama Y., Kasai Y., Yamada S., Tetrahedron, 32, 2211-2217 (1976);
24. b) Takuma S., Hamada Y., Shioiri T., Chem. Pharm. Bull., 30, 3147-3153 (1982) and references therein.
25. The signals of the two aromatic protons of 8 appeared at almost the same position, and were lower than those of 7.
26. 1H-NMR data of both isomers. The signal of the C-7 methylene proton of 15 appeared at δ 3.05 and was shifted to lower field compared to that the (Z)-isomcr (δ 2.91) by the anisotropic effect of the oxygen atom on the oxime moiety.
27. a) Buffalo R. R., Waddell J. E., Yaden E. L., J. Pharmacol. Exp. Ther., 221, 309-314 (1982);
28. b) Jenkin R. A., Baldi M. A., Iwanov V., Moulds R. F. W., J. Cardiovasc. Pharmacol., 18, 566-573 (1991);
29. c) Itoh T., Kitamura K., Kuriyama H., J. Physiol. (London), 345, 409-422 (1983);
30. d) Ishikawa S., Jpn. J. Pharmacol., 35, 19-25 (1984);
31. e) Fujii K., Kuriyama H., J. Pharmacol. Exp. Ther., 235, 764-770 (1985).
32. a) Pleiffer C. C., Science, 124, 29-31 (1956);
33. b) Lehmann F. P. A., Quant. Struct. Act. Relat., 6, 57-65 (1987).
34. a) van Leusen A. M., Siderius H., Hoogenboom B. E., van Leusen D., Tetrahedron Lett., 52, 5337-5340 (1972);
35. b) Holland G. F., U. S. Patent 4282242 (1981) [Chem. Abstr., 95, 187068e (1981)].
36. Huisgen R., Laschtuvka E., Chem. Ber., 93, 65-81 (1960).
37. Otsuka Pharmaceutical Co., Ltd., Jpn. Kokai Tokkyo Koho, JP81 49361 (1981) [Chem. Abstr., 96, 69027p (1982)].
38. Yevich J. P., New J. S., Smith D. W., Lobeck W. G., Catt J. D., Minielli J. L., Eison M. S., Taylor D. P., Riblet L. A., Temple D. J., Jr., J. Med. Chem., 29, 359-369 (1986).
39. Berman M.-C., Bonte J.-P., Lesieur-Demarquilly I., Debaert M., Lesieur D., Leinot M., Benoit J., Labrid C., Eur. J. Med. Chem. Chim. Ther., 17, 85-88 (1982).
40. Guida W. C., Mathre D. J., J. Org. Chem., 45, 3172-3176 (1980).
41. Andersen H. J., Nagy H., Can. J. Chem., 50, 1961-1965 (1972).
42. Leysen J. E., Niemegeers C. J. E., van Nueten J. M., Laduron P. M., Mol. Pharmacol., 21, 301-314 (1982).
43. Greengrass P., Bremner R., Eur. J. Pharmacol., 55, 323-326 (1979).
44. Peroutka S. J., J. Neurochem., 47, 529-540 (1986).
45. Broadhurst A. M., Alexander B. S., Wood M. D., Life Sci., 43, 83-92 (1988).
46. Bylund D. B., Snyder S. H., Mol. Pharmacol., 12, 568-580 (1976).
47. Köhler C., Hall H., Ögren S.-O., Gawell L., Biochem. Pharmacol., 34, 2251-2259 (1985).
48. Yamamura H. I., Snyder S. H., Proc. Natl. Acad. Sci. U.S.A., 71, 1725-1729 (1974).
49. Tran V. T., Chang R. S. L., Snyder S. H., Proc. Natl. Acad. Sci. U.S.A., 75, 6290-6294 (1978).
50. Gajtkowski G. A., Norris D. B., Rising T. J., Wood T. P., Nature (London), 304, 65-67 (1983).
51. Hara H., Kitajima A., Shimada H., Tamano Y., Thromb. Haemostas., 66, 484-188 (1991).