Nitrogen-containing heteroalicycles with serotonin receptor binding affinity: Development of gastroprokinetic and antiemetic agents

Medicinal Research Reviews

Volumn 19, Issue 1, 1999, Pages 25-73

  Kato, Shiro ^a   Fujiwara, Iwao ^a   Yoshida, Naoyuki ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

5 HT4 receptor agonist; 5 HT3 receptor antagonist; Antiemetic agent; AS 8112; DAT 582; Dopamine D2 antagonism; Gastroprokinetic agent; Mosapride

Indexed keywords

ANTIEMETIC AGENT; CISAPRIDE; DOPAMINE 2 RECEPTOR BLOCKING AGENT; METOCLOPRAMIDE; N [1 METHYL 4 (3 METHYLBENZYL)HEXAHYDRO 1,4 DIAZEPIN 6 YL] 1H INDAZOLE 3 CARBOXAMIDE; PROKINETIC AGENT; SEROTONIN 3 ANTAGONIST; SEROTONIN 4 AGONIST; UNCLASSIFIED DRUG;

DRUG EFFECT; DRUG INDICATION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; NONHUMAN; REVIEW; VOMITING;

ANIMALS; ANTIEMETICS; DRUG DESIGN; GASTROINTESTINAL AGENTS; MOLECULAR STRUCTURE; RECEPTORS, SEROTONIN; SEROTONIN ANTAGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0344628865     PISSN: 01986325     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1098-1128(199901)19:1<25::AID-MED3>3.0.CO;2-E     Document Type: Review

References (157)

1. Bradley PB, Engel G, Feniuk W, Fozard JR, Humphrey PPA, Middlemiss DN, Mylecharane EJ, Richardson BP, Saxena PR. Neuropharmacol 1986;25:563.
2. Dumuis A, Sebben M, Bockaert J. Eur J Pharmacol 1989;162:381.
3. Humphrey PPA, Hartig P, Hoyer, D. Trends Pharmacol Sci 1993;14:233.
4. Plassat JL, Boschert U, Amlaiky N, Hen R. EMBO J 1992;11:4779.
5. Watson S, Girdlestone D. Trends Pharmacol Sci 1994;15:51.
6. Lucas JJ, Hen R. Trends Pharmacol Sci 1995;16:246.
7. (a) Pinder RM, Brogden RN, Sawyer PR, Avery GS. Drugs 1976; 12:81;
8. (b) Albibi R, McCallum RW. Ann Intern Med 1983;98:86;
9. (c) McRitchie B, McClelland CM, Cooper SM, Turner DH, Sanger GJ. In: Mechanisms of gastrointestinal motility and secretion. Bennett, A, Velo, GP, editors. New York: Plenum; 1984. p. 287.
10. Sanger GJ, King FD. Drug Design Deliv 1988;3:273.
11. Craig DA, Clark DE. J Pharmacol Exp Ther 1990;252:1378.
12. Baxter GS, Craig DA, Clark DE. Naunyn-Schmiedeberg's Arch Pharmacol 1991;343:439.
13. Andrews PLR, Rapeport WG, Sanger GJ. Trends Pharmacol Sci 1988;9:334.
14. Schuurkes JAJ, Van Nueten JM, Van Daele PG, Reyntjens AJ, Janssen PAJ. J Pharmacol Exp Ther 1985;234:775.
15. Massingham R, Bou J, Roberts DJ. J Auto Pharmac 1985;5:41.
16. Van Daele GHP, DeBruyn MFL, Sommen FM, Janssen M, Van Nueten JM, Shuurkes JAJ, Niemegeers CJE, Leysen JE. Drug Dev Res 1986;8:225.
17. McCallum RW, Prakas C, Campoli-Richards DM, Goa KL. Drugs 1988;36:652.
18. Flynn DL, Zabrowski DL, Becker DP, Nosal R, Villamil CI, Gullikson GW, Moummi C, Yang D-C. J Med Chem 1992;35:1486.
19. (a) Butler A. Hill JM, Ireland SJ, Jordan CC, Tyers MB. Br J Pharmacol 1988;94:397;
20. (b) Milne, RJ, Heel, RC. Drugs 1991;41:574.
21. (a) King FD, Sanger GJ. Drugs Future 1989;14:875;
22. (b) Bermudez J, Fake CS, Joiner GF, Joiner KA, King FD, Miner WD, Sanger GJ. J Med Chem 1990;33:1924;
23. (c) Bermudez J, Dabbs S, Joiner KA, King FD. ibid 1990;33:1929;
24. (d) Idem, ibid 1990;33:1932;
25. (3) Plosker, GL, Goa, KL. Drugs 1991;42:805.
26. Bockaert J, Fozard JR, Dumuis A, Clarke DE. Trends Pharmacol Sci 1992;13:141.
27. Elswood CJ, Bunce KT, Humphrey PPA. Eur J Pharmacol 1995;196:149.
28. McLean PG, Coupar IM, Molenaar P. Br J Pharmacol 1995;115:47.
29. Reeves JJ, Bunce KT, Humphrey PPA. Br J Pharmacol 1991;103:1067.
30. Idres S, Delarue C, Lefebvre H, Vaudry H. Mol Rrain Res 1991;10:251.
31. Tonini M, Messori E, Franceschetti GP, Rizzi CA, Castoldi AF, Coccini T, Candura SM. Br J Pharmacol 1994;113:1.
32. Waikar MV, Ford APD, Clarke DE. Br J Pharmacol 1994;111:213.
33. Kaumann AJ. Naunyn-Schmiedeberg's Arch Pharmacol 1990;342:619.
34. Villalón CM, den Boer MO, Heiligers JPC, Saxena PR. Br J Pharmacol 1990;100:665.
35. Kaumann AJ, Sanders L, Brown AM, Murray KJ, Brown MJ. Br J Pharmacol 1990;100:879.
36. Kaumann AJ, Sanders L, Brown AM, Murray KJ, Brown MJ. Naunyn-Schmiedeberg's Arch Pharmacol 1991;344:150.
37. Bart JA, Branchek T, Weinshank RL. WO 94 09,828, 1994; Chem Abstr 1994;121:126145m.
38. Eglen RM, Hegde SS. Exp Opin Invest Drugs 1996;5:373.
39. Drugs Future 1985;10:553.
40. Alphin RS, Proakis AG, Leonard CA, Smith WL, Dannenburg WN, Kinnier WJ, Johnson DN, Sancilio LF, Ward JW. Dig Dis Sci 1986;31:524.
41. Prietol J, Moragues J, Spickett RG, Vega A, Colombo M, Salazar W, Roberts DJ. J Pharm Pharmac 1977;29:147.
42. Drugs Future 1984;9:497.
43. Hadley MS, King FD. EP 0,013,138, 1980.
44. Hadley MS, King FD, McRitchie B, Turner DH, Watts EA. J Med Chem 1985;28:1843.
45. 38.(a) Drugs Future 1986;12:1009;
46. (b) Dunbar AW, McClelland CM, Sanger GJ. Br J Pharmacol 1986;88:319;
47. (c) Sanger GJ. Br J Pharmacol 1987;91:77.
48. Gullikson GW, Virina MA, Loeffler RF, Yang D-C, Goldstin B, Wang S-X, Moummi C, Flynn DL, Zabrowski DL. J Pharmacol Exp Ther 1993;264:240.
49. Kato S, Morie T, Hino K, Ron K, Naruto S, Yoshida N, Karasawa T, Matsumoto J. J Med Chem 1990;33:1406.
50. Picciola G. Boll Chim Farm 1980;119:141.
51. Loftus F. Synth Commun 1980;10:59.
52. Scarpignato C, Capovilla T, Bertaccini G. Arch Int Pharmacodyn 1980;246:286.
53. Jacoby HI, Brodie DA. Gastroenterol 1967;52:676.
54. Janssen PAJ, Niemegeers CJE, Schellekens KHL. Arzneim-Forsch 1965;15:1196.
55. List SJ, Seeman P. Proc Natl Acad Sci USA 1981;78:2620.
56. Kato S, Morie T, Yoshida N, Matsumoto J. Chem Pharm Bull 1992;40:1470.
57. Kato S, Morie T, Kon K, Yoshida N, Karasawa T, Matsumoto J. J Med Chem 1991;34:616.
58. Kato S, Morie T, Harada H. Yoshida N, Matsumoto J. Chem Pharm Bull 1992;40:652.
59. Kato S, Morie T, Yoshida N. Chem Pharm Bull 1995;43:699.
60. Yoshida N, Omoya H, Oka M, Furukawa K, Ito T, Karasawa T. Arch Int Pharmacodyn Ther 1989;300:51.
61. Yoshida N, Kato S, Ito T. Drugs Future 1993;18:513.
62. Dewar MJS, Zoebisch GE, Healy EF, Stewart JJP. J Am Chem Soc 1985;107:3902.
63. SYBYL, version 6.1; Tripos Associates, 1699 S. Hanley Rd, Suite 303, St. Louis, MO 63144.
64. Morie T, Kato S, Harada H, Yoshida N, Matsumoto J. Chem Pharm Bull 1994;42:877.
65. Morie T, Kato S, Harada H, Matsumoto J. Heterocycles 1994;38:1033.
66. Howe R, Leigh T, Rao BS, Todd AH. J Med Chem 1976;19:1074.
67. Craig DA, Clarke DE. J Pharmacol Exp Ther 1990;252:1378.
68. Morie T, Kato S, Harada H, Yoshida N, Fujiwara I, Matsumoto J. Chem Pharm Bull 1995;43:1137.
69. Hatanaka M, Kawaguchi A, Nitta H, Ishimaru T. Synthesis, 1985;688.
70. Omodei-Sale A, Toja E. Farmaco Ed Sci 1975;30:650.
71. Bailey DM, Wood D, Johnson RE, McAuliff JP, Bradford JC, Arnold A. J Med Chem 1972;15:344.
72. Morie T, Kato S, Harada H, Yoshida N, Fujiwara I, Watanabe K, Matsumoto J. J Chem Soc Perkin Trans 1 1994;2565.
73. Brown GR, Foubister AJ, Stribling D. J Chem Soc Perkin Trans 1 1987;547.
74. Piper JP, Johnston TP. J Org Chem 1963;28:981.
75. Sharma S, Iyer RN, Anand N. Indian J Chem 1975;13:468.
76. Schipper ES, Boehme WR, Graeme ML, Siegnund E, Chinery E. J Med Pharm Chem 1961;4:79.
77. Brown GR, Foubister AJ, Wright B. J Chem Soc Perkin Trans 1 1987;553.
78. Berkes D, Decroix B. Bull Soc Chim Fr 1994;131:986.
79. Deo NM, Crooks PA. Synth Commun 1995;25:691.
80. Perrio-Huard C, Ducandas C, Lasne MC, Moreau B. J Chem Soc Perkin Trans 1 1996;2925.
81. Yoshida N, Omoya H, Furukawa K, Oka M, Ito T. Jpn Pharmacol Ther 1993;21:3013.
82. Yoshida N, Ito T, Karasawa T, Itoh Z. J Pharmacol Exp Ther 1991;257:781.
83. Yoshida N, Ito T. Neurogastroenterol Mot 1994;6:167.
84. Mine Y, Yoshikawa T, Oku S, Nagai R, Yoshida N, Hosoki K. J Pharmacol Exp Ther 1997;283:1000.
85. Yoshiwaka T, Yoshikawa N, Mine Y, Hosoki K. Jpn J Pharmacol 1998;77:53.
86. Karasawa T, Yoshida N, Furukawa K, Omoya H, Ito T. Eur J Pharmacol 1990;183:2181.
87. Jenkins JR, Gibson J. Care 1996;24:728.
88. Ahmad SR, Wolfe SM. Lancet 1995;345:508.
89. Kii Y, Ito T. J Cardiovasc Pharmacol 1997;29:670.
90. Puisieux FL, Adamantidis MM, Dumotier BM, Dupuis BA. Br J Pharmacol 1996;117:1377.
91. Carlsson L, Amos GJ, Andersson B, Drews L, Duker G, Wadstedt G. J Pharmacol Exp Ther 1997;282:220.
92. Laszlo J, Lucas Jr VS. N Engl J Med 1981;305:948.
93. Huys J, Troch M, Bourguignon RP, Smets PH. Curr Med Res Opin 1985;9:400.
94. Gralla RJ, Itri LM, Pisko SE, Squillante AE, Kelsen DP, Braun Jr DW, Bordin LA, Braun TJ, Young CW. N Engl J Med 1981;305:905.
95. Plezia PM, Alberts DS, Kessler J, Aapro MS, Graham V, Surwit EA. Cancer Treat Rep 1984;68:1493.
96. Kris MG, Gralla RJ, Tyson LB, Clark RA, Kelsen DP, Reilly LK, Groshen S, Bosl JG, Kalman LA. Cancer 1985;55:527.
97. Indo T, Ando K. Arch Neurol 1982;39:494.
98. Harrington RA, Hamilton CW, Brogden RN, Linkewich JA, Romankiewicz JA, Heel RC. Drugs 1983; 25:451.
99. Kris MG, Tyson LB, Gralla RJ, Clark RA, Allen JC, Reilly LK. N Engl J Med 1983;309:433.
100. Leopold NA. Neurology 1984;34:238.
101. Fozard JR, Mobarok Ali ATM. Eur J Pharmacol 1978;49:109.
102. Miner WD, Sanger GJ. Br J Pharmacol 1986;88:497.
103. Fozard JR. Trends Pharmacol Sci 1987;8:44.
104. Tyers MB, Bunce KT, Humphrey PPA. Eur J Cancer Clin Oncol 1989;25(Suppl 1):S15.
105. 96.(a) Richardson BP, Engel G, Donatsch P, Stadler PA. Nature (London) 1985;316:126;
106. (b) Costall B, Domeney AM, Naylor RJ, Tattersall FD. Neuropharmacol 1986;25:959;
107. (c) Leibundgut U, Lancranjan, I. Lancet 1987;1:1198.
108. Smith WL, Sancilio LF, Owera-Atepo JB, Naylor RJ, Lambert L. J Pharm Pharmacol 1988;40:301.
109. Smith WL, Alphin RS, Jackson CB, Sancilio LF. J Pharm Pharmacol 1989;41:101.
110. Kilpatrick GJ, Jones BJ, Tyers MB. Nature (London) 1987;330:746.
111. Costall B, Domeney AM, Naylor RJ, Tyers MB. Br J Pharmacol 1987;92:881.
112. Jones BJ, Costall B, Domeney AM, Kelly ME, Naylor RJ, Oakley NR, Tyers MB. Br J Pharmacol 1988; 93:985.
113. Cooper SJ, Abbott A. Trends Pharmacol Sci 1988;9:269.
114. 103.(a) Steadnab CJ, Talley NJ, Phillips SF, Mulvihill C. Gastroenterology 1990;98:A394;
115. (b) Maxton DG, Haigh CG, Whorwell PJ. ibid 1991;100:A468.
116. Prior A, Read NW. Gut 1990;31:A1174.
117. Yoshida N, Ito T, Itoh Z. J Gastrointest Motility 1991;3:209.
118. Fozard JR. Naunyn-Schmiedeberg's Arch Pharmacol 1984;326:36.
119. Cohen ML, Bloomquist W, Gidda JS, Lacefield W. J Pharmacol Exp Ther 1989;248:197.
120. Harada H, Morie T, Hirokawa Y, Yoshida N, Kato S. Chem Pharm Bull 1995;43:1364.
121. Harada H, Morie T, Hirokawa Y, Terauchi H, Fujiwara I, Yoshida N, Kato S. Chem Pharm Bull 1995; 43:1912.
122. Kon T, Kato S, Morie T, Karasawa T, Yoshida N. Jpn Kokai Tokkyo Koho JP 02,256,670 [90,256,670].
123. Yoshida N, Omoya H, Kato S, Ito T. Eur J Pharmacol 1992;216:435.
124. Saari WS, Raab AW, King SW. J Org Chem 1971;36:1711.
125. Mitsunobu O. Synthesis 1981;1.
126. Harada H, Hirokawa Y, Morie T, Kato S. Heterocycles 1995;41:363.
127. Biere H, Redmann U. Eur J Med Chem 1976;11:351.
128. 116.(a) Jukar E, Rissi E. Helv Chim Acta 1962;45:2383;
129. (b) Cortes S, Kohn H. J Org Chem 1983;48:2246.
130. Tamura N, Matsusita Y, Yoshioka K, Ochiai M. Tetrahedron 1988;44:3231.
131. Kato S, Harada H, Morie T. J Heterocyclic Chem 1995;32:637.
132. 119.(a) Snyder HR, Kirchner CB, Hinman RL. J Am Chem Soc 1952;74:2009;
133. (b) Ferrari M, Ripa G, Sisti MJ. J Heterocyclic Chem 1989;26:531;
134. (c) Yoshida T, Matsuura N, Yamamoto K, Doi M, Shimada K, Morie T, Kato S. Heterocycles 1996;43:2701.
135. Harada H, Morie T, Hirokawa Y, Kato S. Chem Pharm Bull 1996;44:2205.
136. Morie T, Harada H, Kato S. Synth Commun 1997;27:559.
137. Arnold Z, Sauliová J, Krchnák V. Collect Czech Chem Commun 1973;38:2633.
138. Harada H, Morie T, Hirokawa Y, Kato S. Tetrahedron: Asymmetry 1997;8:2367.
139. Kato S, Harada H, Morie, T. J Chem Soc Perkin Trans 1 1997;3219.
140. Kato S, Morie T, Ito T, Yoshida N. Jpn Kokai Tokkyo Koho JP 05,230,057 [93,230,057]: Chem Abstr 1994;120:164242c.
141. Collet A, Brienne M-J, Jacques J. Chem Rev 1980;80:215.
142. Smrt J, Beránek J, Sicher J, Skoda J, Hess VF, Sorm F. Experientia 1957;13:291.
143. Willems JGH, Hersmis MC, de Gelder R, Smits JMM, Hammink JB, Donnerholt FJ, Thijs L, Zwanenburg B. J Chem Soc Perkin Trans 1 1997;963.
144. Kato S, Morie T. Jpn Kokai Tokkyo Koho JP 07,138,239 [95,138,239].
145. Yoshida N, Omoya H, Ito T. J Pharmacol Exp Ther 1992;260:1159.
146. 131.(a) Brogden RN, Carmine AA, Heel RC, Speight TH, Avery GS. Drugs 1982;24:360;
147. (b) Davis RH, Clench MH, Mathiae JR. Dig Dis Sci 1988;33:1505.
148. Triozzi PL, Laszlo J. Drugs 1987;34:136.
149. Hirokawa Y, Morie T, Yamazaki H, Yoshida N, Kato S. Bioorg Med Chem Lett 1998;8:619.
150. Hirokawa Y, Yoshida N, Kato S. Bioorg Med Chem Lett, 1998;8:1551.
151. Coldwell MC, Gadre A, Lerman J, King FD, Nash D. Bioorg Med Chem Lett 1995;5:39.
152. Kilpatrick GJ, Jones BJ, Tyers MB. Eur J Pharmacol 1989;159:157.
153. Yoshikawa T, Yoshida N, Omoya H, Kato S, Hosoki K. Jpn J Pharmacol 1997;73:216P.
154. Yoshida N, Yoshikawa T, Omoya H, Kato S, Hosoki K. ibid 1997;73:216P.
155. Yoshida N, Yoshikawa T, Hosoki K. Life Sci 1996;57:PL347.
156. Yoshikawa T, Yoshida N, Hosoki K. Eur J Pharmacol 1996;301:143.
157. Robinson OPW. J Postgrad Med 1973;49:77.