Claims
- 1. A 1,4-Substituted cyclic amine derivative (I) represented by the following formula or a pharmacologically acceptable salt thereof:
- 2. A 1,4-Substituted cyclic amine derivative (II) represented by the following formula or a pharmacologically acceptable salt thereof:
- 3. The 1,4-substituted cyclic amine derivative as set forth in claim 1 or 2 or a pharmacologically acceptable salt thereof, wherein m is 0 and p is 2.
- 4. The 1,4-substituted cyclic amine derivative as set forth in any of claims 1 to 3 or a pharmacologically acceptable salt thereof, wherein Y is methine and Z is nitrogen.
- 5. The 1,4-substituted cyclic amine derivative (III) as set forth in any of claims 1 to 4, represented by the following formula or a pharmacologically acceptable salt thereof:
- 6. The 1,4-substituted cyclic amine derivative (IV) as set forth in claim 1, represented by the following formula or a pharmacologically acceptable salt thereof:
- 7. The 1,4-substituted cyclic amine derivative (V) as set forth in claim 6, represented by the following formula or a pharmacologically acceptable salt thereof:
- 8. The 1,4-substituted cyclic amine derivative (VI) as set forth in claim 6, represented by the following formula or a pharmacologically acceptable salt thereof:
- 9. The 1,4-substituted cyclic amine derivative as set forth in claim 1 or a pharmacologically acceptable salt thereof, which is a compound selected from among the following ones:
(1) 1-[1-(4-fluorophenyl)piperidin-4-yl]indoline, (2) 1-[1-(4-fluorobenzyl)piperidin-4-yl]indoline, (3) 1-(1-phenethylpiperidin-4-yl)indoline, (4) 1-[1-(4-bromophenethyl)piperidin-4-yl]indoline, (5) 1-[1-(3-chlorophenethyl)piperidin-4-yl]indoline, (6) 1-[1-(4-chlorophenethyl)piperidin-4-yl]indoline, (7) 1-[1-(2-fluorophenethyl)piperidin-4-yl]indoline, (8) 1-[1-(3-fluorophenethyl)piperidin-4-yl]indoline, (9) 1-[1-(4-fluorophenethyl)piperidin-4-yl]indoline, (10) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]indoline, (11) 1-[1-(3,4-difluorophenethyl)piperidin-4-yl]indoline, (12) 1-[1-(3,5-difluorophenethyl)piperidin-4-yl]indoline, (13) 1-[1-(4-fluorophenylpropyl)piperidin-4-yl]indoline, (14) 1-{1-[2-(4-fluorophenyl)propyl]piperidin-4-yl}indoline, (15) 1-[1-(4-fluorophenylbutyl)piperidin-4-yl]indoline, (16) 1-[1-(4-fluorophenethyl)piperidin-4-yl]methylindoline, (17) 1-{2-[1-(4-fluorophenethyl)piperidin-4-yl]ethyl}indoline, (18) 1-[1-(4-methoxyphenethyl)piperidin-4-yl]indoline, (19) 1-[1-(3-methoxyphenethyl)piperidin-4-yl]indoline, (20) 1-[1-(4-hydroxyphenethyl)piperidin-4-yl]indoline, (21) 1-[1-(4-cyanophenethyl)piperidin-4-yl]indoline, (22) 1-[1-(3-hydroxymethylphenethyl)piperidin-4-yl]indoline, (23) 1-[1-(4-hydroxymethylphenethyl)piperidin-4-yl]indoline, (24) 1-{1-[4-(2-hydroxyethyl)phenethylpiperidin-4-yl}indoline, (25) 1-{4-[(1-hydroxyethyl)phenethyl]piperidin-4-yl}indoline, (26) 1-{1-[4-(2-hydroxyethoxy)phenethyl]piperidin-4-yl}indoline, (27) 1-[1-(4-trifluoromethylphenethyl)piperidin-4-yl]indoline, (28) 1-[1-(4-methanesulfonylphenethyl)piperidin-4-yl]indoline, (29) 1-[1-(4-nitrophenethyl)piperidin-4-yl]indoline, (30) 1-[1-(4-aminophenethyl)piperidin-4-yl]indoline, (31) 1-[1-(4-methylsulfonylaminophenethyl)piperidin-4-yl]indoline and 1-{1-[4-bis(methylsulfonyl)aminophenethyl]piperidin-4-yl}indoline, (32) 1-[1-(4-acetamidophenethyl)piperidin-4-yl]indoline, (33) 1-[1-(4-ethylaminophenethyl)piperidin-4-yl]indoline, (34) 1-[1-(4-hydroxyiminomethylphenethyl)piperidin-4-yl]indoline, (35) 1-[1-(4-aminomethylphenethyl)piperidin-4-yl]indoline, (36) 1-[1-(4-acetamidomethylphenethyl)piperidin-4-yl]-indoline, (37) 1-[1-(4-chloroacetamidomethylphenethyl)piperidin-4-yl]indoline, (38) 1-[1-(4-methanesulfonylaminomethylphenethyl)piperidin-4-yl]indoline, (39) 1-[1-(4-propionylaminomethylphenethyl)piperidin-4-yl]-3-methylindoline, (40) 1-[1-(4-carbamoylphenethyl)piperidin-4-yl]indoline, (41) 1-[1-(4-N-isopropylcarbamoylmethylphenethyl)piperidin-4-yl]indoline, (42) 1-[1-(4-sulfamoylphenethyl)piperidin-4-yl]indoline, (43) 1-{3-[(2-hydroxyethoxy)phenethyl]piperidin-4-yl}indoline, (44) 1-{1-[4-(2-dimethylaminoethoxy)phenethyl]piperidin-4-yl]indoline}, (45) 1-{1-[3,4-di(hydroxymethyl)phenethyl]piperidin-4-yl}indoline, (46) 1-{1-[3,4-(methylenedioxy)phenethyl]piperidin-4-yl}indoline, (47) 1-{1-[2-(4-chlorophenylsulfonylamino)ethyl]piperidin-4-yl}indoline, (48) 1-{1-[2-(4-methoxyphenylsulfonylamino)ethyl]piperidin-4-yl}indoline, (49) 1-{1-[2-(4-pyridyl)ethyl]piperidin-4-yl}indoline, (50) 1-{1-[2-(2-pyridyl)ethyl]piperidin-4-yl}indoline, (51) 1-{1-[2-(3-pyridyl)ethyl]piperidin-4-yl}indoline, (52) 1-{1-[2-(2-methoxy-5-pyridyl)ethyl]piperidin-4-yl}indoline, (53) 1-{1-[2-(3-methoxypyridin-5-yl)ethyl]piperidin-4-yl}indoline, (54) 1-{1-[2-(2-cyanopyridin-5-yl)ethyl]piperidin-4-yl}indoline, (55) 1-{1-[2-(2-hydroxymethylpyridin-5-yl)ethyl]piperidin-4-yl}indoline, (56) 1-{1-[2-(3-hydroxymethylpyridin-5-yl)ethyl]piperidin-4-yl}indoline, (57) 1-[1-(2,6-difluoro-3-pyridylethyl)piperidin-4-yl]indoline, (58) 1-{1-[2-(2-thienyl)ethyl]piperidin-4-yl}indoline, (59) 1-{1-[2-(3-thienyl)ethyl]piperidin-4-yl}indoline, (60) 1-[1-(2-thiazolylethyl)piperidin-4-yl]indoline, (61) 1-[1-(4-methyl-5-thiazolylethyl)piperidin-4-yl]indoline, (62) 1-{1-[(indol-3-yl)ethyl]piperidin-4-yl}indoline, (63) 1-{1-[2-(6-benzothiazolyl)ethyl]piperidin-4-yl}indoline, (64) 1-[1-(5-methoxy-2-thienyl)ethylpiperidin-4-yl]indoline, (65) 1-[1-(2-methoxy-5-thiazolyl)ethylpiperidin-4-yl]indoline, (66) 1-[1-(2-cyano-5-thiazolyl)ethylpiperidin-4-yl]indoline, (67) 1-(1-pyrazinylethylpiperidin-4-yl)indoline, (68) 1-{1-[2-(4-bromopyrazol-1-yl)ethyl]piperidin-4-yl}indoline, (69) 1-{1-[3-(4-fluorophenoxy)propyl]piperidin-4-yl}indoline, (70) 1-{1-[3-(4-hydroxymethylphenoxy)propyl]piperidin-4-yl}indoline, (71) 1-{1-[3-(4-hydroxyethylphenoxy)propyl]piperidin-4-yl}indoline, (72) 1-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}indoline, (73) 1-{1-[4-(4-fluorophenyl)-4-hydroxybutyl]piperidin-4-yl}indoline, (74) 1-[1-(phthalimido-1-yl)ethylpiperidin-4-yl]indoline, (75) 1-[1-(4-fluorobenzamido)ethylpiperidin-4-yl]indoline, (76) 1-{1-[1-(3,4-dimethoxyphenyl)propan-2-yl]piperidin-4-yl}indoline, (77) 1-{1-[(1,4-benzodioxan-2-yl)methyl]piperidin-4-yl}indoline, (78) 1-{1-[3-(3,4-methylenedioxyphenoxy)propyl]piperidin-4-yl}indoline, (79) 1-[1-(4-fluorophenethyl)-3-methylpiperidin-4-yl]indoline, (80) 1-(1-benzyl-3-hydroxymethylpiperidin-4-yl)indoline, (81) 1-[1-(4-fluorophenethyl)-3-hydroxymethylpiperidin-4-yl]indoline, (82) 1-[1-(4-fluorophenethyl)-3-hydroxymethylpiperidin-4-yl]indoline, (83) 1-[2-(4-acetamidomethylphenyl)ethyl]-4-(indan-1-yl)piperidin-1-oxide, (84) 1-[1-ethyl-3-(4-fluorophenoxymethyl)piperidin-4-yl]indoline, (85) 1-[1-ethyl-3-(4-fluorobenzyloxymethyl)piperidin-4-yl]indoline, (86) 1-[1-ethyl-3-(4-fluorobenzyloxymethyl)piperidin-4-yl]indoline, (87) 1-(1-acetylpiperidin-4-yl)indoline-7-carbaldehyde, (88) 1-[1-(4-t-butoxycarbonyl)piperidin-4-yl]-6-bromoindoline, (89) 1-[1-(4-t-butoxycarbonyl)piperidin-4-yl]-6-hydroxymethylindoline, (90) 1-[1-(4-t-butoxycarbonyl)piperidin-4-yl]-6-aminomethylindoline, (91) 1-(1-benzylpiperidin-4-yl)-6-bromoindoline, (92) 1-(1-benzylpiperidin-4-yl)-6-fluoroindoline, (93) 1-(1-benzylpiperidin-4-yl)-6-formylindoline, (94) 1-(1-benzylpiperidin-4-yl)-6-hydroxyiminomethylindoline, (95) 1-(1-benzylpiperidin-4-yl)-6-aminomethylindoline, (96) 1-(1-benzylpiperidin-4-yl)-6-acetamidomethylindoline, (97) 1-[1-(4-methoxyphenethyl)piperidin-4-yl]-6-acetamidomethylindoline, (98) 1-[1-(4-chlorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline, (99) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-5-methoxyindoline, (100) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoindoline, (101) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoindoline, (102) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-chloroindoline, (103) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-fluoroindoline, (104) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyindoline, (105) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-4-methoxyindoline, (106) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methoxyindoline, (107) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-7-methoxyindoline, (108) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6,7-dimethoxyindoline, (109) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-nitroindoline, (110) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminoindoline, (111) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methylaminoindoline, (112) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-ethylaminoindoline, (113) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-isopropylaminoindoline, (114) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-dimethylaminoindoline, (115) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetamidoindoline, (116) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methanesulfonylaminoindoline, (117) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-ethanesulfonylaminoindoline, (118) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-propanesulfonylaminoindoline, (119) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(4-fluorobenzenesulfonylamino)indoline, (120) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(N-methylmethanesulfonylamino)indoline, (121) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyethoxyindoline, (122) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methanesulfonyloxyindoline, (123) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-7-hydroxyethoxyindoline, (124) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-cyanoindoline, (125) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carbamoylindoline, (126) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-pyrrolylcarbonyl)indoline, (127) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetylindoline, (128) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methanesulfonylindoline, (129) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-thiocarbamoylmethylindoline, (130) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-formylindoline, (131) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindoline, (132) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline, (133) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline, (134) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline, (135) 1-[1-(3-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline, (136) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxymethylindoline, (137) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxyethyl)indoline, (138) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxypropyl)indoline, (139) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxy-1-methylethyl)indoline, (140) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxycyclobutyl)indoline, (141) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxycyclopentyl)indoline, (142) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-chloromethylindoline, (143) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-fluoromethylindoline, (144) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-fluoroethyl)indoline, (145) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-cyanomethylindoline, (146) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carboxymethylindoline, (147) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carbamoylmethylindoline, (148) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(methylcarbamoylmethyl)indoline, (149) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(ethylcarbamoylmethyl)indoline, (150) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(n-propylcarbamoylmethyl)indoline, (151) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(isopropylcarbamoylmethyl)indoline, (152) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(isobutylcarbamoylmethyl)indoline, (153) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(t-butylcarbamoylmethyl)indoline, (154) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(cyclopropylcarbamoylmethyl)indoline, (155) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(tetramethylenecarbamoylmethyl)indoline, (156) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-propionylaminomethylindoline, (157) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(n-butyryl)aminomethylindoline, (158) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-isobutyrylaminomethylindoline, (159) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-cyclopropanecarboxamidomethylindoline, (160) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methylsulfonylaminomethylindoline, (161) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-ureidomethylindoline, (162) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-N-methylaminomethylindoline, (163) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-N-methylacetamidomethylindoline, (164) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(N-methylsulfamoylmethyl)indoline, (165) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-acetamidoethyl)indoline, (166) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetamidoethylindoline, (167) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(piperidin-4-yl)methyl]indoline, (168) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(1-acetylpiperidin-4-yl)methyl]indoline, (169) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(1-ethylpiperidin-4-yl)methyl]indoline, (170) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(1-methylpiperidin-4-yl)methyl]indoline, (171) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-pyridyl)indoline, (172) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-thiazolyl)indoline, (173) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-methylpyrrol-2-yl)indoline, (174) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-pyridyl)methyl]indoline, (175) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(2-pyridyl)methyl]indoline, (176) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(3-pyridyl)methyl]indoline, (177) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(3-pyridyl)methyl]indoline, (178) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxy-4-pyridylmethyl)indoline, (179) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(4-pyridylmethyl)indoline, (180) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-pyridylcarbonyl)indoline, (181) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-pyridyl)ethyl]indoline, (182) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(2-pyridyl)ethyl]indoline, (183) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-pyridylcarbonyl)indoline, (184) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-methoxypyridin-3-yl)methyl]indoline, (185) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(2-methoxypyridin-3-yl)methyl]indoline, (186) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-methoxypyridin-6-yl)methyl]indoline, (187) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(2-methoxypyridin-6-yl)methyl]indoline, (188) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-methoxypyridin-5-yl)methyl]indoline, (189) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(2-methoxypyridin-5-yl)methyl]indoline, (190) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-pyridon-5-yl)methyl]indoline, (191) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-dimethylaminopyridin-5-yl)methyl]indoline, (192) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-chloropyridin-5-yl)methyl]indoline, (193) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(2-thiazolyl)-1-hydroxymethyl]indoline, (194) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-thiazolylcarbonyl)indoline, (195) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(4-thiazolyl)-1-hydroxymethyl]indoline, (196) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-(5-thiazolyl)-1-hydroxymethyl]indoline, (197) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(pyrimidin-2-yl)methyl]indoline, (198) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(pyrimidin-5-yl)methyl]indoline, (199) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[1-hydroxy-1-(2-pyrrolyl)methyl]indoline, (200) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-N,N-dimethylaminomethylindoline, (201) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(4-fluorophenyl)indoline, (202) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindoline, (203) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-piperidon-1-yl)methylindoline, (204) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(succinimido-1-yl)methylindoline, (205) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(glutarimido-1-yl)methylindoline, (206) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-imidazolidonyl)methylindoline, (207) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2,4-imidazolidinedion-3-yl)methylindoline, (208) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-oxazolidon-3-yl)methylindoline, (209) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2,4-thiazolidinedion-3-yl)methylindoline, (210) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(pyrrol-1-yl)methylindoline, (211) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(imidazol-1-yl)methylindoline, (212) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1,2,3-triazol-1-yl)methylindoline and 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1,2,3-triazol-2-yl)methylindoline, (213) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1,2,4-triazol-2-yl)methylindoline, (214) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-thiazolyl)methylindoline, (215) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-3-(4-methoxybenzyl)indoline, (216) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-3-methylindoline, (217) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-5-chloro-6-aminoindoline, (218) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-5-chloro-6-methanesulfonylaminoindoline, (219) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-5-chloro-6-methoxyindoline, (220) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]-6-aminoindoline, (221) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]-6-methanesulfonylaminoindoline, (222) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]-6-acetamidoindoline, (223) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]-6-bromoindoline, (224) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]-6-acetamidomethylindoline, (225) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]-6-carbamoylmethylindoline, (226) 1-{1-[3-(4-fluorophenyl)propyl]piperidin-4-yl}-6-acetamidomethylindoline, (227) 1-{1-[4-(4-fluorophenyl)butyl]piperidin-4-yl}-6-acetamidomethylindoline, (228) 1-[1-(4-methoxyphenethyl)piperidin-4-yl]-6-methoxyindoline, (229) 1-[1-(4-methoxyphenethyl)piperidin-4-yl]-6-fluoroindoline, (230) 1-[1-(4-sulfamoylphenethyl)piperidin-4-yl]-6-methoxyindoline, (231) 1-[1-(4-fluorophenoxypropyl)piperidin-4-yl]-6-bromoindoline, (232) 1-[1-(4-fluorophenoxypropyl)piperidin-4-yl]-6-acetamidomethylindoline, (233) 1-{1-[2-(6-benzothiazolyl)ethyl]piperidin-4-yl}-6-methoxyindoline, (234) 1-[1-(4-fluorophenethyl)piperidin-4-yl]thiazolo[5,4-f]indoline, (235) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminothiazolo[5,4-f]indoline, (236) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-7-hydroxy-(4a,7a)-cyclohexanoindoline and 1-[1-(4-fluorophenethyl)piperidin-4-yl]-4-hydroxy-(3b,6a)-cyclohexanoindoline, (237) 1-(1-methylpiperidin-4-yl)-6-(4-fluorobenzenesulfonylamino)indoline, (238) 1-(1-ethylpiperidin-4-yl)-6-(4-fluorobenzenesulfonylamino)indoline, (239) 1-(1-ethylpiperidinyl)-4-(4-fluorophenyl)indoline, (240) 1-(1-ethylpiperidin-4-yl)-3-(4-fluorophenyl)indoline, (241) 1-(1-ethylpiperidin-4-yl)-3-(4-methoxyphenyl)indoline, (242) 1-(1-ethylpiperidin-4-yl)-3-(4-methoxybenzyl)indoline, (243) 1-[(1-ethylpiperidin-4-yl)methyl]-3-(4-methoxybenzyl)indoline, (244) 1-(1-ethylpiperidin-4-yl)-3-(4-fluorobenzylindoline, (245) 1-(1-ethylpiperidin-4-yl)-3-(3-pyridylmethyl)indoline, (246) 1-(1-ethylpiperidin-4-yl)-3-(3-methoxyphenethyl)indoline, (247) 1-(1-ethylpiperidin-4-yl)-3-(3-fluorophenethyl)indoline, (284) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-5,6-methylenedioxyindoline, (285) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindole, (286) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(N-isopropylcarbamoylmethyl)indole, (287) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-methylpyrrol-2-yl)indole, (288) 1-[1-(4-acetamidomethylphenethyl)piperidin-4-yl]indole, (289) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-cyanoindole, (290) 1-[1-(4-fluorophenethyl)-3-methylpiperidin-4-yl]indole, (291) 1-[1-(4-fluorophenethyl)homopiperidin-4-yl]-6-methoxyindoline, (292) 1-[1-(4-fluorophenethyl)pyrrolidin-3-yl]-6-methoxyindoline, (293) 3,3-dimethyl-1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoindoline, (294) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(ethylcarbamoylmethyl)indole, (295) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[N-(cyclopropylcarbamoyl)methyl]indole, (296) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[N-(isobutylcarbamoyl)methyl]indole, (297) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(n-propylcarbamoylmethyl)indole, (298) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(tetramethylenecarbamoylmethyl)indole, (299) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]-6-carbamoylmethylindole, (300) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-hydroxyethyl)carbamoylmethylindole, (301) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-dimethylcarbamoylmethylindole, (302) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(4-hydroxypiperidin-1-ylcarbonylmethyl)indole, (303) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[bis(2-hydroxyethyl)carbamoylmethyl]indole, (304) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1,3-dihydroxypropan-2-yl)carbamoylmethylindole, (305) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carbamoylmethylindole, (306) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(carbamoylmethyl)carbamoylmethylindole, (307) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-dimethylaminoethyl)carbamoylmethylindole, (308) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-cyanomethylcarbamoylmethylindole, (309) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-methoxyethyl)carbamoylmethylindole, (310) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-fluoroethyl)carbamoylmethylindole, (311) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[2-(ethylcarbamoyl)ethyl]indole, (312) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[2-(pyrrolidin-1-yl)ethyl]carbamoylmethylindole, (313) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[2-(morpholin-4-yl)ethyl]carbamoylmethylindole, (314) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(pyridin-4-yl)methylcarbamoylmethylindole, (315) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[2-(pyridin-2-yl)ethyl]carbamoylmethylindole, (316) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methylcarbamoylmethylindole, (317) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-methoxypyridin-5-ylcarbonyl)indole, (318) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(2-methoxypyridin-5-yl)hydroxymethyl]indole, (319) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxyproyl)indole, (320) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxy-1-methylethyl)indoline, (321) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-hydroxypropyl)indole, (322) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methanesulfonamidomethylindole, (323) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-isopropylsulfonamidomethylindole, (324) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-n-propylsulfonamidomethylindole, (325) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-chloropropyl)sulfonamidomethylindole, (326) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1,3-propanesultam-2-yl)methylindole, (327) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-propionylaminomethylindole, (328) 3-chloro-1-[1-(4-fluorophenethyl)-piperidin-4-yl]-6-acetamidomethylindole, (329) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(4-hydroxybutyroylamidomethyl)indole, (330) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyethoxyindole, (331) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methanesulfonylindole, (332) 1-[1-(2,6-difluoro-3-pyridylethyl)piperidin-4-yl]indole, (333) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-fluoroindole, (334) 1-[1-(4-fluorophenethyl)piperidin-4-yl]thiazolo[5,4-f]indole, (335) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(N-methylmethanesulfonylamino)indole, (336) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methanesulfonyloxyindole, (337) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-carbamoylindole, (338) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(N-methylsulfamoylmethyl)indole, (339) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetamidoindole, (340) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1,2-dihydroxypropan-3-yl)carbamoylmethylindole, (341) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(pyridin-2-yl)methylcarbamoylmethylindole, (342) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-methylcarbamoylmethylindole, (343) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-(1-acetylpiperidin-4-yl)methylcarbamoylmethylindole, (344) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-ethylcarbamoylmethylindole, (345) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-ethylpiperidin-4-yl)methylcarbamoylmethylindole, (346) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-(2-hydroxyethyl)carbamoylmethylindole, (347) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1,3-dioxolan-2-ylmethyl)carbamoylmethylindole, (348) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-aminomethylindole, (349) 1-[1-(4-chlorophenethyl)piperidin-4-yl]-6-acetamidomethylindole, (350) 1-[1-(3-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindole, (351) 1-[1-(4-methoxyphenethyl)piperidin-4-yl]-6-acetamidomethylindole, (352) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindole, (353) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2,4-imidazolidinedion-3-yl)methylindole, (354) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-isobutyrylaminomethylindole, (355) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-imidazolidonyl)methylindole, (356) 1-{1-[4-(4-fluorophenyl)butyl]piperidin-4-yl}-6-acetamidomethylindole, (357) 1-[1-(2,4-difluorophenethyl)piperidin-4-yl]-6-acetamidomethylindole, (358) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(2-pyrrolidon-1-yl)methylindole, (359) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-N-methylacetamidomethylindole, (360) 1-{1-[3-(4-fluorophenyl)propyl]piperidin-4-yl}-6-acetamidomethylindole, (361) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-N-methylaminomethylindole, (362) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(n-butyryl)aminomethylindole, (363) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-cyclopropanecarboxamidomethylindole, (364) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyacetamidomethylindole, (365) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-difluoroacetamidomethylindole, (366) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-fluoroacetamidomethylindole, (367) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-chloropropionylamino)methylindole, (368) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-imidazocarbonylaminomethylindole, (369) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-hydroxypropionylamino)methylindole, (370) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-3-formyl-6-acetamidomethylindole, (371) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-3-hydroxyimino-6-acetamidomethylindole, (372) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-3-hydroxymethyl-6-acetamidomethylindole, (373) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-chloroacetamidomethylindole, (374) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-bromoacetamidomethylindole, (375) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(N,N-dimethylaminoacetamido)methylindole, (376) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[(piperidin-1-yl)acetamido]methylindole, (377) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-bromopropionylamino)methylindole, (378) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-N,N-dimethylaminopropionyl)aminomethylindole, (379) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-[3-(piperidin-1-yl)propionylamino]methylindole, (380) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-propionylaminomethylindole, (381) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-fluoroacetamidomethylindole, (382) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-(3-hydroxypropionylamino)methylindole, (383) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-hydroxyacetamidomethylindole, (384) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methoxycarbonylaminomethylindole, (385) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-N,N-dimethylaminocarbonylaminomethylindole, (386) 1-{1-[2-(3-pyridyl)ethyl]piperidin-4-yl}-6-acetamidomethylindole, (387) 3-cyano-1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetamidomethylindole, (388) 1-{4-[(1-hydroxyethyl)phenethyl]piperidin-4-yl}-6-acetamidomethylindole, (389) 1-[1-(4-bromophenethyl)piperidin-4-yl]-6-acetamidomethylindole, (390) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-formylindole, (391) 1-[1-(2-fluorophenethyl)piperidin-4-yl]-6-hydroxymethylindole, (392) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(1-hydroxyethyl)indole, (393) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-ureidomethylindole, (394) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-methylureido)methylindole, (395) 3,3-dimethyl-1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-acetamidoindoline, (396) 2,2-dimethyl-1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-methoxyindoline, and (397) 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-(3-methylureido)methylindole.
- 10. A pharmaceutical composition comprising the 1,4-substituted cyclic amine derivative as set forth in claim 1 or a pharmacologically acceptable salt thereof and a carrier.
- 11. An agent for treating, ameliorating and preventing diseases against which serotonin antagonism is efficacious, which contain as the active ingredient the 1,4-substituted cyclic amine derivative as set forth in claim 1 or a pharmacologically acceptable salt thereof.
- 12. An agent for treating, ameliorating and preventing spastic paralysis, which contain as the active ingredient the 1,4-substituted cyclic amine derivative as set forth in claim 1 or a pharmacologically acceptable salt thereof.
- 13. A muscle relaxant which contains as the active ingredient the 1,4-substituted cyclic amine derivative as set forth in claim 1 or a pharmacologically acceptable salt thereof.
- 14. A process for producing a 1,4-substituted cyclic amine derivative (X) represented by the following formula:
- 15. A process for producing 1,4-substituted cyclic amine derivative (X), as set forth in claim 1, which comprises reacting a fused cyclic amine (VII) represented by the following formula:
- 16. A 4-substituted cyclic amine derivative (XX) represented by the following formula:
- 17. A method for treating a disease to which serotonin antagonism is efficacious, which comprises administering an effective dose of the 1,4-substituted cyclic amine derivative as set forth in claim 1, or a pharmacologically acceptable salt thereof to a person.
- 18. Use of the 1,4-substituted cyclic amine derivative as set forth in claim 1, or a pharmacologically acceptable salt thereof for treating a disease to which serotonin antagonism is efficacious.
- 19. The 1,4-substituted cyclic amine derivative as set forth in claim 1, in which the bond represented by the following formula in the formula (I): ______
- 20. The 1,4-substituted cyclic amine derivative as set forth in claim 1, in which m is 0 in the formula (I), represented by the formula (XXII):
- 21. The 1,4-substituted cyclic amine derivative as set forth in claim 1, in which m is 1 to 6 in the formula (I) or a pharmacologically acceptable salt thereof.
- 22. The 1,4-substituted cyclic amine derivative as set forth in claim 1, selected from the group consisting of:
(16) 1-[1-(4-fluorophenethyl)piperidin-4-yl]methylindoline, (17) 1-{2-[1-(4-fluorophenethyl)piperidin-4-yl]ethyl}indoline, (243) 1-[(1-ethylpiperidin-4-yl)methyl]-3-(4-methoxybenzyl)indoline, (342-5) 1-[1-(2-fluorophenethylpiperidin-4-yl)]-6-(methylcarbamoylmethyl)indole, and pharmacologically acceptable salts thereof.
- 23. A 1,4-substituted cyclic amine derivative represented by the formula (XXIII):
- 24. The 1,4-substituted cyclic amine derivative as set forth in claim 23, selected from: (256) 7-[1-(4-fluorophenethyl) piperidin-4-ylidene]-5,6-dihydropyrindine and (265) 5-[1-(4-fluorophenethyl)piperidin-4-ylidene]-7-methyl-5,6-dihydrocy clopentapyrazine or a pharmacologically acceptable salt thereof.
- 25. The 1,4-substituted cyclic amine derivative as set forth in claim 1, of the formula (XXIV):
Priority Claims (2)
Number |
Date |
Country |
Kind |
9-98433 |
Mar 1997 |
JP |
|
9-366764 |
Dec 1997 |
JP |
|
Parent Case Info
[0001] This application is a division of co-pending application Ser. No. 09/367,227, filed on Aug. 11, 1999, to which priority is claimed under 35 U.S.C. § 120. application Ser. No. 09/367,227 is the 35 U.S.C. § 371 national phase of PCT International Application No. PCT/JP98/01481, filed on Mar. 31, 1998. The entire contents of each of the above-identified applications are hereby incorporated by reference. This application also claims 35 U.S.C. § 119 priority to Applications Nos. 9-98433 and 9-366764 filed in Japan on Mar. 31, 1997 and Dec. 26, 1997, respectively.
Divisions (1)
|
Number |
Date |
Country |
Parent |
09367227 |
Aug 1999 |
US |
Child |
09859517 |
May 2001 |
US |