US 5,849,912 A · Biphenyl derivatives

Biphenyl derivatives

AssigneeEisai Co., Ltd.

InventorsKozo Akasaka, Masahiro Yonaga, Akiharu Kajiwara, Kunizo Higurashi, Kohshi Ueno, Satoshi Nagato, Makoto Komatsu, Noritaka Kitazawa, Masataka Ueno, Yoshiharu Yamanishi, Yoshimasa Machida, Yuki Komatsu, Naoyuki Shimomura, Norio Minami, Toshikazu Shimizu, Atsushi Nagaoka

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Abstract

A biphenyl derivative represented by the following formula (I) or a pharmacologically acceptable salt thereof: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are defined in the specification, is clinically useful for treating and ameliorating mental disorders such as cerebrovascular disorder, aggressive behavior due to senile dementia, mental excitation, poriomania, delirium, hallucination, hyperkinesia, schizophrenia, emotional disturbance, depression, neurosis, psychophysiologic disorder and anxiety neurosis. The compounds exhibit dopamine 2 receptor antagonism and/or serotonin 2 receptor antagonism.

Claims6

Dependent claims

A biphenyl compound represented by the following formula (I) or a pharmacologically acceptable salt thereof:

##STR257## wherein R.sup.1 is a halogenated lower alkyl group or a lower alkylsulfonylamino group;
R.sup.2 is a halogen atom or a lower alkoxy group;
R.sup.3 is a halogen atom, a lower alkyl group or a cyano group;
R.sup.4 is a hydrogen atom or a halogen atom;
R.sup.5 is a hydrogen atom, a lower alkyl group or a hydroxy lower alkyl group;
and n is 0.

3 more elements

The biphenyl compound or a pharmacologically acceptable salt thereof which is a compound selected from the group consisting of

(1) 1-3-(2-cyanophenyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(2) 1-(2-hydroxyethyl)-4-3-(2-cyanophenyl)-4-chloro-5-(1-fluoropropyl)!phenyl piperazine,
(3) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-ethoxycarbonyl!phenylpiperazine,
(4) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-amino!phenylpiperazine,
(5) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-propanesulfonylamino!phenylpiperazine,
(6) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-ethanesulfonylamino!phenylpiperazine,
(7) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-butanesulfonylamino!phenylpiperazine,
(8) 1-methyl-4-3-(2-cyanophenyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine
(9) 1-ethyl-4-3-(2-cyanophenyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(10) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazin e,
(11) 1-(2-hydroxyethyl)-4-3-(2-chlorophenyl)-4-chloro-5-(1-fluoropropyl)!pheny lpiperazine,
(12) 1-ethyl-4-3-(2-chlorophenyl)-4-chloro-5(1-fluoropropyl)!phenylpiperazine,
(13) 1-methyl-4-3-(2-tolyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(14) 1-(2-hydroxyethyl)-4-3-(2-tolyl)-4-chloro-5-(1-fluoropropyl)!phenylpipera zine,
(15) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(16) 1-methyl-4-3-(2-tolyl)-4-chloro-5-ethanesulfonylamino!phenylpiperazine,
(17) 1-methyl-4-3-(2-tolyl)-4-chloro-5-propanesulfonylamino!phenylpiperazine,
(18) 1-methyl-4-3-(2-tolyl)-4-chloro-5-butanesulfonylamino!phenylpiperazine,
(19) 1-ethyl-4-3-(2-chlorophenyl)-4-chloro-5-ethanesulfonylamino!phenylpiperaz ine,
(20) 1-ethyl-4-3-(2-chlorophenyl)-4-chloro-5-propanesulfonylamino!phenylpipera zine,
(21) 1-ethyl-4-3-(2-chlorophenyl)-4-chloro-5-butanesulfonylamino!phenylpiperaz ine,
(22) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-ethanesulfonylamino!phenylpipera zine,
(23) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-propanesulfonylamino!phenylpiper azine,
(24) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-butanesulfonylamino!phenylpipera zine,
(25) 1-ethyl-4-3-(4-fluorophenyl)-4-methoxy-5-ethanesulfonylamino!phenylpipera zine,
(26) 1-ethyl-4-(3-phenyl-4-methoxy-5-chloromethyl)phenylpiperazine,
(27) 1-ethyl-4-{3-phenyl-4-methoxy-5-1-fluoro-(4-pentenyl)!}phenylpiperazine,
(28) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-fluorobutyl)!phenylpiperazine,
(29) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-fluoropentyl)!phenylpiperazine,
(30) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-fluorobutyl)!phenylpiperazine,
(31) 1-ethyl-4-3-(2-tolyl)-4-fluoro-5-(1-fluorobutyl)!phenylpiperazine,
(32) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-fluoro-3-methylbutyl)!phenylpiperazin e,
(33) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-fluoroethyl)!phenylpiperazine,
(34) 1-methyl-4-3-(2-tolyl)-4-chloro-5-(1-fluorobutyl)!phenylpiperazine,
(35) 1-ethyl-4-3-(2-chlorophenyl)-4-chloro-5-(1-fluorobutyl)!phenylpiperazine,
(36) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1,1-difluoropropyl)!phenylpiperazine,
(37) 1-ethyl-4-(3,5-diphenyl-4-methoxy)phenylpiperazine,
(38) 1-ethyl-4-(3-phenyl-4-methoxy)phenylpiperazine,
(39) 1-ethyl-4-(3,5-diphenyl-4-hydroxy)phenylpiperazine,
(40) 1-ethyl-4-(3-phenyl-4-methoxy-5-propyl)phenylpiperazine,
(41) 1-ethyl-4-(3,5-diphenyl-4-isopropoxy)phenylpiperazine,
(42) 1-ethyl-4-(3-phenyl-4-isopropoxy)phenylpiperazine,
(43) 1-ethyl-4-(3-phenyl-4-hydroxy)phenylpiperazine,
(44) 1-ethyl-4-2-methoxy-3-phenyl-5-(3-hydroxypropyl)!phenylpiperazine,
(45) 1-hydroxyethyl-4-(3,5-diphenyl-4-methoxy)phenylpiperazine,
(46) 1-ethyl-4-3-(4-fluorophenyl)-4-methoxy-5-propyl)!phenylpiperazine,
(47) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-hydroxyethyl)!phenylpiperazine,
(48) 1-ethyl-4-2-methoxy-3-phenyl-5-(2-hydroxyethyl)!phenylpiperazine,
(49) 1-ethyl-4-3-phenyl-4-methoxy-5-(3-methoxypropyl)!phenylpiperazine,
(50) 1-ethyl-4-3-phenyl-4-methoxy-5-(3-methoxymethoxypropyl)!phenylpiperazine,
(51) 1-ethyl-4-(3-phenyl-4-methoxy-5-ethyl)phenylpiperazine,
(52) 1-ethyl-4-3-phenyl-4-methoxy-5-(3-cyanopropyl)!phenylpiperazine,
(53) 1-(2-fluoroethyl)-4-3-(4-fluorophenyl)-4-methoxy-5-propyl!phenylpiperazin e,
(54) 1-ethyl-4-3-(4-methoxyphenyl)-4-methoxy-5-propyl!phenylpiperazine,
(55) 1-ethyl-4-(3-phenyl-4-methoxy-5-methoxycarbonyl)phenylpiperazine,
(56) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-hydroxypropyl)!phenylpiperazine,
(57) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-fluoroethyl)!phenylpiperazine,
(58) 1-ethyl-4-3-phenyl-4-methoxy-5-(3-fluoropropyl)!phenylpiperazine,
(59) 1-ethyl-4-3-(4-fluorophenyl)-4-methoxy-5-isopropyl!phenylpiperazine,
(60) 1-ethyl-4-3-(4-fluorophenyl)-4-methoxy-6-isopropyl!phenylpiperazine,
(61) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-hydroxyisopropyl)!phenylpiperazine,
(62) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-butoxypropyl)!phenylpiperazine,
(63) 1-ethyl-4-(3-phenyl-4-methoxy-5-propionyl)phenylpiperazine,
(64) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-hydroxypropyl)!phenylpiperazine,
(65) 1-ethyl-4-3-(2-fluorophenyl)-4-methoxy-5-propyl!phenylpiperazine,
(66) 1-ethyl-4-3-(4-trifluoromethylphenyl)-4-methoxy-5-propyl!phenylpiperazine
(67) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-fluoroisopropyl)!phenylpiperazine,
(68) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-hydroxyisopropyl)!phenylpiperazine,
(69) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-fluoropropyl)!phenylpiperazine,
(70) 1-ethyl-4-(3-phenyl-4-methoxy-5-cyano)phenylpiperazine,
(71) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-furanyl)!phenylpiperazine,
(72) 1-ethyl-4-3-(2,4-difluorophenyl)-4-methoxy-5-propyl!phenylpiperazine,
(73) 1-ethyl-4-(3-phenyl-4-methoxy-5-phenylacetyl)phenylpiperazine,
(74) 1-ethyl-4-3-phenyl-4-methoxy-5-(4-fluorophenyl)acetyl!phenylpiperazine,
(75) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-hydroxyphenethyl)!phenylpiperazine,
(76) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-tetrahydrofuranyl)!phenylpiperazine,
(77) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-fluorophenethyl)!phenylpiperazine,
(78) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-pyridyl)!phenylpiperazine,
(79) 1-ethyl-4-{3-phenyl-4-methoxy-5-4-fluoro-(1hydroxyimino)phenethyl!}phenyl piperazine,
(80) 1-ethyl-4-{3-phenyl-4-methoxy-5-1-fluoro-2-(2-pyridyl)ethyl!}phenylpipera zine,
(81) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-propenyl)!phenylpiperazine,
(82) 1-ethyl-4-3-(3-fluorophenyl)-4-methoxy-5-propyl!phenylpiperazine,
(83) 1-ethyl-4-(3-phenyl-4-methoxy-5-hydroxymethyl)phenylpiperazine,
(84) 1-ethyl-4-3-phenyl-4-methoxy-5-(4-pyridyl)acetyl!phenylpiperazine,
(85) 1-ethyl-4-(3-phenyl-4-methoxy-5-methanesulfinyl)phenylpiperazine,
(86) 1-ethyl-4-(3-phenyl-4-methoxy-5-ethanesulfinyl)phenylpiperazine,
(87) 1-ethyl-4-(3-phenyl-4-methoxy-5-formyl)phenylpiperazine,
(88) 1-ethyl-4-3-phenyl-4-methoxy-5-(1,3-dioxan-2-yl)!phenylpiperazine,
(89) 1-ethyl-4-(3-phenyl-4-methoxy-5-cyclopropaneacetyl)phenylpiperazine,
(90) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-pyridylcarbonyl)!phenylpiperazine,
(91) 1-ethyl-4-(3-phenyl-4-methoxy-5-amino)phenylpiperazine,
(92) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-ethoxycarbonylethyl)!phenylpiperazine,
(93) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-pyridyl)hydroxymethyl!phenylpiperazine,
(94) 1-ethyl-4-(3-phenyl-5-propyl-6-methoxy)phenylpiperazine,
(95) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-acetylethyl)!phenylpiperazine,
(96) 1-ethyl-4-{3-phenyl-4-methoxy-5-1-(2-pyridylmethoxy)propyl!}phenylpiperaz ine,
(97) 1-ethyl-4-3-(2-tolyl)-4-methoxy-5-propyl!phenylpiperazine,
(98) 1-ethyl-4-(3-phenyl-4-methoxy-5-propylamino)phenylpiperazine,
(99) 1-(3-phenyl-4-hydroxy-5-phenylacetyl)phenylpiperazine,
(100) 1-ethyl-4-(3-phenyl-4-methoxy-5-benzylsulfinyl)phenylpiperazine,
(101) 1-ethyl-4-(3-phenyl-4-methoxy-5-benzenesulfonylamino)phenylpiperazine,
(102) 1-ethyl-4-{3-phenyl-4-methoxy-5-1-fluoro-2-(4-pyridyl)ethyl!}phenylpipera zine,
(103) 1-ethyl-4-3-phenyl-4-methoxy-5-(N-ethanesulfonyl-N-methylamino)!phenylpip erazine,
(104) 1-ethyl-4-(3-phenyl-4-methoxy-5-ethylaminosulfonyl)phenylpiperazine,
(105) 1-ethyl-4-(3-phenyl-4-methoxy-5-aminosulfonyl)phenylpiperazine,
(106) 1-(3-phenyl-4-methoxy-5-phenylacetyl)phenylpiperazine,
(107) 1-benzyl-4-(3-phenyl-4-methoxy-5-phenylacetyl)phenylpiperazine,
(108) 1-ethyl-4-3-phenyl-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(109) 1-hydroxyethyl-4-(3-phenyl-4-methoxy-5-phenylacetyl)phenylpiperazine,
(110) 1-ethyl-4-3-phenyl-5-(1-fluoropropyl)!phenylpiperazine,
(111) 1-ethyl-4-(3-phenyl-5-propionyl)phenylpiperazine,
(112) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(113) 1-ethyl-4-3-(2-methoxyphenyl)-4-methoxy-5-propyl!phenylpiperazine,
(114) 1-ethyl-4-(3-phenyl-4-methoxy-5-ethanesulfonyl)phenylpiperazine,
(115) 1-ethyl-4-(3-phenyl-4-methoxy-5-dimethylaminosulfonyl)phenylpiperazine,
(116) 1-ethyl-4-3-phenyl-4-methoxy-5-(1-pyrrolidinylsulfonyl)!phenylpiperazine,
(117) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(2,2,2-trifluoroethyl)sulfonylamino!phen ylpiperazine,
(118) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(4-fluorophenylsulfonylamino)!phenylpipe razine,
(119) 1-ethyl-4-3-phenyl-4-chloro-5-(1-hydroxypropyl)!phenylpiperazine,
(120) 1-ethyl-4-(3-phenyl-4-chloro-5-ethanesulfonyl)phenylpiperazine,
(121) 1-ethyl-4-(3-phenyl-4-chloro-5-propionyl)phenylpiperazine,
(122) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-pyrrolidylsulfonyl)!phenylpiperazine,
(123) 1-ethyl-4-{3-2-(4-fluorotolyl)!-4-chloro-5-(1-fluoropropyl)}phenylpiperaz ine,
(124) 1-ethyl-4-3-(2-methoxyphenyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazin e,
(125) 1-ethyl-4-3-(2,4-difluorophenyl)-4-chloro-5-(1-fluoropropyl)!phenylpipera zine,
(126) 1-ethyl-4-3-(2-methoxymethylphenyl)-4-chloro-5-(1-fluoropropyl)!phenylpip erazine,
(127) 1-ethyl-4-{3-2-(4-fluorotolyl)!-4-chloro-5-cyclopropaneaminosulfonyl}phen ylpiperazine,
(128) 1-ethyl-4-3-phenyl-4-chloro-5-(1-methylpropyl)!phenylpiperazine,
(129) 1-ethyl-4-{3-2-(4-fluorotolyl)!-4-chloro-5-cyclopropylmethylsulfonyl}phen ylpiperazine,
(130) 1-ethyl-4-(3-phenyl-4-fluoro-5-ethanesulfonyl)phenylpiperazine,
(131) 1-3-(4-pyridyl)propyl!-4-3-(2-tolyl)-4-chloro-5-(1-fluoropropyl)!phenylp iperazine,
(132) 1-propyl-4-3-(2-tolyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(133) 1-ethyl-4-3-(2-hydroxymethylphenyl)-4-chloro-5-(1-fluoropropyl)!phenylpip erazine,
(134) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-propanesulfonylamino!phenylpiperazine,
(135) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-dimethylaminosulfonyl!phenylpiperazine,
(136) 1-ethyl-4-3-(2-tolyl)-4-fluoro-5-methanesulfonyl!phenylpiperazine,
(137) 1-ethyl-4-3-(2-chloro-4-fluorophenyl)-4-chloro-5-(1-fluoropropyl)!phenylp iperazine,
(138) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-ethylpropyl)!phenylpiperazine,
(139) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-methanesulfonyl!phenylpiperazine,
(140) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-propanesulfonyl!phenylpiperazine,
(141) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-fluoro-4-pentenyl)!phenylpiperazine,
(142) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-propylaminosulfonyl!phenylpiperazine,
(143) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-ethanesulfonylamino!phenylpiperazine,
(144) 1-ethyl-4-3-(2-chlorophenyl)-4-chloro-5-(2,2,2-trifluoroethyl)sulfonylami no!phenylpiperazine,
(145) 1-ethyl-4-3-(2-tolyl)-4-cyano-5-(1-fluoropropyl)!phenylpiperazine,
(146) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(3-chloropropyl)sulfonylamino!phenylpipe razine,
(147) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-phenylaminosulfonyl!phenylpiperazine,
(148) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-benzyloxymethyl!phenylpiperazine,
(149) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-propoxymethyl!phenylpiperazine,
(150) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(4-pyridyl)methoxymethyl!phenylpiperazin e,
(151) 1-ethyl-4-(3-phenyl-4-methoxy-5-propanesulfonyl)phenylpiperazine,
(152) 1-ethyl-4-(3-phenyl-4-methoxy-5-butanesulfonyl)phenylpiperazine,
(153) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-fluoroethane)sulfonyl!phenylpiperazine,
(154) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-ethoxymethyl!phenylpiperazine,
(155) 1-methyl-4-3-(2-tolyl)-4-chloro-5-(1-hydroxybutyl)!phenylpiperazine,
(156) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-allyloxymethyl!phenylpiperazine,
(157) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-cyclopropylmethoxymethyl!phenylpiperazin e,
(158) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1-pyrrolidinyl)!phenylpiperazine,
(159) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-(1-fluorobutyl)!phenylpiperazine
(160) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-benzylsulfonylamino!phenylpipera zine,
(161) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-propanesulfonyl!phenylpiperazine
(162) 1-ethyl-4-{3-phenyl-4-methoxy-5-3-(4-fluorophenoxy)propane!sulfonyl}pheny lpiperazine,
(163) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-isopropylsulfonylamino!phenylpip erazine,
(164) 1-ethyl-4-3-phenyl-4-methoxy-5-(2-cyanoethylsulfonyl)!phenylpiperazine,
(165) 1-ethyl-4-(3-phenyl-4-chloro-5-propanesulfonylamino)phenylpiperazine,
(166) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-difluoromethyl!phenylpiperazine,
(167) 1-ethyl-4-3-phenyl-4-methoxy-5-(1,1-difluoropropyl)!phenylpiperazine,
(168) 1-ethyl-4-3-(4-methoxyphenyl)-4-chloro-5-propanesulfonylamino!phenylpiper azine,
(169) 1-methyl-4-3-(2-chlorophenyl)-4-chloro-5-methanesulfonylamino!phenylpiper azine,
(170) 1-ethyl-4-3-(2,4-dichlorophenyl)-4-chloro-5-propanesulfonylamino!phenylpi perazine,
(171) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-(1,3-dithian-2-yl)!phenylpiperazine,
(172) 1-ethyl-4-3-phenyl-4-chloro-5-propanesulfonyl!phenylpiperazine,
(173) 1-ethyl-4-3-(2-tolyl)-4-chloro-5-propanesulfonylaminomethyl!phenylpiperaz ine,
(174) 1-methyl-4-3-(4-fluorophenyl)-4-methoxy-5-propanesulfonyl!phenylpiperazin e,
(175) 1-ethyl-4-3-(2-ethylphenyl)-4-chloro-5-propanesulfonylamino!phenylpiperaz ine,
(176) 1-hydroxyethyl-4-3-(4-fluorophenyl)-4-methoxy-5-ethanesulfonyl!phenylpipe razine,
(177) 1-ethyl-4-3-(2-formylphenyl)-4-chloro-5-propanesulfonylamino!phenylpipera zine,
(178) 1-ethyl-4-3-(2-cyanophenyl)-4-chloro-5-propanesulfonylamino!phenylpiperaz ine,
(179) 1-(2-pyridylethyl)-4-3-(4-fluorophenyl)-4-methoxy-5-ethanesulfonyl!phenyl piperazine,
(180) 1-(2-pyridylmethyl)-4-3-(4-fluorophenyl)-4-methoxy-5-ethanesulfonyl!pheny lpiperazine,
(181) 1-(3-pyridylmethyl)-4-3-(4-fluorophenyl)-4-methoxy-5-ethanesulfonyl!pheny lpiperazine,
(182) 1-(4-pyridylethyl)-4-3-(4-fluorophenyl)-4-methoxy-5-ethanesulfonyl!phenyl piperazine,
(183) 1-3-(4-fluorophenyl)-4-methoxy-5-ethanesulfonyl!phenylpiperazine,
(184) 1-(2-fluoroethyl)-4-3-(4-fluorophenyl)-4-methoxy-5-ethanesulfonyl!phenylp iperazine,
(185) 1-ethyl-4-3-(2-chlorophenyl)-4-chloro-5-(1-propenyl)!phenylpiperazine,
(186) 1-ethyl-4-3-(2-chlorophenyl)-4-chloro-5-(1-chloropropyl)!phenylpiperazine
(187) 1-methyl-4-3-phenyl-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(188) 1-methyl-4-3-(2-hydroxymethylphenyl)-4-chloro-5-(1-fluoropropyl)!phenylpi perazine,
(189) 1-ethyl-4-3-(2-fluoromethylphenyl)-4-chloro-5-(1-fluoropropyl)!phenylpipe razine,
(190) 1-methyl-4-{3-(2-fluoromethylphenyl)-4-chloro-5-1-fluoropropyl!}phenylpip erazine,
(191) 1-ethyl-4-{3-2-(4-fluorotolyl)!-4-chloro-5-1-fluoropropyl!}phenylpiperaz ine,
(192) 1-2-(2-pyridyl)ethyl!-4-3-(2-tolyl)-4-chloro-5-(1-fluoropropyl)!phenylpi perazine,
(193) 1-2-(2-pyridyl)ethyl!-4-3-(2-cyanophenyl)-4-chloro-5-(1-fluoropropyl)!ph enylpiperazine,
(194) 1-ethyl-4-3-(2,6-xylyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(195) 1-ethyl-4-{3-(2-trifluoromethylphenyl)-4-chloro-5-1-fluoropropyl!}phenylp iperazine,
(196) 1-ethyl-4-3-(2-ethylphenyl)-4-chloro-5-(1-fluoropropyl)!phenylpiperazine,
(197) 1-(2-hydroxyethyl)-4-3-(2-ethylphenyl)-4-chloro-5-(1-fluoropropyl)!phenyl piperazine,
(198) 1-(2-hydroxyethyl)-4-{3-(2-trifluoromethylphenyl)-4-chloro-5-1-fluoroprop yl!}phenylpiperazine,
(199) 1-methyl-4-{3-(2-tolyl)-4-chloro-5-1-fluoropropyl!}phenylpiperazine, and
(200) 1-(2-hydroxyethyl)-4-{3-2-(4-fluorotolyl)!-4-chloro-5-1-fluoropropyl!}ph enylpiperazine.

197 more elements

Dependencies are inferred from the claim text.

Facts

Application

08/855,790Filed 12 May 1997 · continuation

Priority

JP 6-8103029 Mar 1994

Granted

15 Dec 1998

Term ends

Not estimatedThe source records don’t support an estimate.

Classification25 codes

C07D 213/30
Radicals substituted by singly-bound oxygen or sulphur atoms: oxygen atoms
A61P 25/18
Drugs for disorders of the nervous system: antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
C07D 213/26
With substituted hydrocarbon radicals attached to ring carbon atoms: radicals substituted by halogen atoms or nitro radicals
C07D 213/38
Radicals substituted by singly-bound nitrogen atoms: having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom