US 6,605,620 B1 · Cyclic amine compounds and pharmaceutical composition containing the same

Abstract

A cyclic amine compound by the following general formula (1): wherein, R1, R2 and R3 each independently represent a hydrogen atom or an alkoxy group W1 and W2 each independently represent N or CH; X represents O, NR4, CONR4 or NR4CO; R4 represents a hydrogen atom, or an alkyl, aryl, heteroaryl, aralkyl, or heteroaralkyl group; and l, m and n each represents a number of 0 or 1, a salt thereof and a hydrate thereof are provided. These compounds have inhibitory effects on both cell adhesion and cell infiltration and are useful as anti-asthmatic agents, anti-allergic agents, anti-rheumatic agents, anti-arteriosclerotic agents, anti-inflammatory agents, anti-Sjogren's syndrome agents or the like.

A cyclic amine selected from the group consisting of:

4-[N-(4-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzoyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine,
4-[N-(4-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzoyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine,
4-[N-(4-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzoyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine,
4-[N-(4-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N-(4-Ethoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Ethoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Ethoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-(4-Ethoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Ethoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Ethoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Ethoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Ethoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N-(4-Butoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Butoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Butoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-(4-Butoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Butoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Butoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Butoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Butoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N-(3-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(3-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(3-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-(3-Methoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(3-Methoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(3-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-(3-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(3-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N-(2-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(2-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(2-Methoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(2-Methoxyphenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(2-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-(2-Methoxyphenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(2,3-Dimethoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[4-(Trifluoromethoxy)phenyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[4-(Trifluoromethoxy)phenyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-[4-(Trifluoromethoxy)phenyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-[4-(Trifluoromethoxy)phenyl]-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[4-(Trifluoromethoxy)phenyl]-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-[4-(Trifluoromethoxy)phenyl]-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-[4-(Trifluoromethoxy)phenyl]-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-[4-(Trifluoromethoxy)phenyl]-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-4-[N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-N-(4-methylthiophenyl)amino]piperidine trihydrochloride,
1-[[3-(3,4,5-Trimethoxyphenyl)pyridin-5-yl]methyl]-4-[N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-N-(4-methylthiophenyl)amino]piperidine trihydrochloride,
1-[3-(3,4,5-Trimethoxyphenyl)benzyl]-4-[N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-N-(4-methylthiophenyl)amino]piperidine dihydrochloride,
1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-4-[N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]-N-(4-methylthiophenyl)amino]piperidine trihydrochloride,
1-[[3-(3,4,5-Trimethoxyphenyl)pyridin-5-yl]methyl]-4-[N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]-N-(4-methylthiophenyl)amino]piperidine trihydrochloride,
1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-4-[N-[3-(3,4,5-trimethoxyphenyl)benzyl]-N-(4-methylthiophenyl)amino]piperidine dihydrochloride,
1-[[3-(3,4,5-Trimethoxyphenyl)pyridin-5-yl]methyl]-4-[N-[3-(3,4,5-trimethoxyphenyl)benzyl ]-N-(4-methylthiophenyl)amino]piperidine dihydrochloride,
1-[3-(3,4,5-Trimethoxyphenyl)benzyl]-4-[N-[3-(3,4,5-trimethoxyphenyl)benzyl]-N-(4-methylthiophenyl)amino]piperidine hydrochloride,
1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-4-[N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-N-(4-methylphenyl)amino]piperidine trihydrochloride,
1-[[3-(3,4,5-Trimethoxyphenyl)pyridin-5-yl]methyl]-4-[N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-N-(4-methylphenyl)amino]piperidine trihydrochloride,
1-[3-(3,4,5-trimethoxyphenyl)benzyl]-4-[N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-N-(4-methylphenyl)amino]piperidine dihydrochloride,
1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-4-[N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]-N-(4-methylphenyl)amino]piperidine trihydrochloride,
1-[[3-(3,4,5-Trimethoxyphenyl)pyridin-5-yl]methyl]-4-[N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]-N-(4-methylphenyl)amino]piperidine trihydrochloride,
1-[[2-(3,4,5-Trimethoxyphenyl)pyridin-4-yl]methyl]-4-[N-[3-(3,4,5-trimethoxyphenyl)benzyl]-N-(4-methylphenyl)amino]piperidine dihydrochloride,
1-[[3-(3,4,5-Trimethoxyphenyl)pyridin-5-yl]methyl]-4-[N-[3-(3,4,5-trimethoxyphenyl)benzyl]-N-(4-methylphenyl)amino]piperidine dihydrochloride,
1-[3-(3,4,5-Trimethoxyphenyl)benzyl]-4-[N-[3-(3,4,5-trimethoxyphenyl)benzyl]-N-(4-methylphenyl)amino]piperidine hydrochloride,
4-[N-[4-(Trifluoromethyl)phenyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[4-(Trifluoromethyl)phenyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-[4-(Trifluoromethyl)phenyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-[4-(Trifluoromethyl)phenyl]-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-(4-(Trifluoromethyl)phenyl]-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-[4-(Trifluoromethyl)phenyl]-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N-(4-Bromophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Bromophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Bromophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-(4-Bromophenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Bromophenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Bromophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Bromophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Bromophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N-(4-Chlorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Chlorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Chlorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-(4-Chlorophenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Chlorophenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Chlorophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Chlorophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Chlorophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N-(3,4-Difluorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(3,4-Difluorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(3,4-Difluorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-(3,4-Difluorophenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(3,4-Difluorophenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(3,4-Difluorophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-(3,4-Difluorophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(3,4-Difluorophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N-(4-Fluorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Fluorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Fluorophenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine dihydrochloride,
4-[N-(4-Fluorophenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Fluorophenyl)-N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]amino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Fluorophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4[N-(4Fluorophenyl)-N-[3(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[[3-(3,4,5trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Fluorophenyl)-N-[3-(3,4,5-trimethoxyphenyl)benzyl]amino]-1-[3-(3,4,5-trimethoxyphenyl)benzyl]piperidine hydrochloride,
4-[N[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-N-phenylamino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]-N-phenylamino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]-N-phenylamino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine trihydrochloride,
4-[N-[3-(3,4,5-trimethoxyphenyl)benzyl]-N-phenylamino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine dihydrochloride,
4-[N-[3-(3,4,5-trimethoxyphenyl)benzyl]-N-phenylamino]-1-[[3-(3,4,5-trimethoxyphenyl)pyridin-5-yl]methyl]piperidine dihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[(2-phenylpyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[(2-phenylpyridin-4-yl)methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[(2-phenylpyridin-4-yl)methyl]amino]-1-[(2-phenylpyridin-4-yl) methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(2-methoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(2-methoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(2-methoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(2-methoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3-methoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3-methoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3-methoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3-methoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
1-[[2-(4-Ethoxyphenyl)pyridin-4-yl]methyl]-4-[N-(4-methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine trihydrochloride,
4-[N-[[2-(4-Ethoxyphenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
1-[[2-(4-Ethoxyphenyl)pyridin-4-yl]methyl]-4-[N-[[2-(4-ethoxyphenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4-dimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3,4-dimethoxyphenyl)pyridin-4-yl]methyl]amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-(4-Methoxyphenyl)-N-[[2-(3,4-dimethoxyphenyl)pyridin-4-yl]methyl]amino]-[[2-(3,4-dimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
1-[[2-(2-Fluorophenyl)pyridin-4-yl]methyl]-4-[N-(4-methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine trihydrochloride,
4-[N-[[2-(2-Fluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[[2-(2-Fluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(2-fluorophenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
1-[[2-(3-Fluorophenyl)pyridin-4-yl]methyl]-4-[N-(4-methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine trihydrochloride,
4-[N-[[2-(3-Fluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[[2-(3-Fluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3-fluorophenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
1-[[2-(4-Fluorophenyl)pyridin-4-yl]methyl]-4-[N-(4-methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine trihydrochloride,
4-[N-[[2-(4-Fluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[[2-(4-Fluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(4-fluorophenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
1-[[2-(3,4-Difluorophenyl)pyridin-4-yl]methyl]-4-[N-(4-methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine trihydrochloride,
4-[N-[[2-(3,4-Difluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[[2-(3,4-Difluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,4-difluorophenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
1-[[2-(3,5-Difluorophenyl)pyridin-4-yl]methyl]-4-[N-(4-methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine trihydrochloride,
4-[N-[[2-(3,5-Difluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[[2-(3,5-Difluorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,5-difluorophenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
1-[[2-(4-Chlorophenyl)pyridin-4-yl]methyl]-4-[N-(4-methoxyphenyl)-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amino]piperidine trihydrochloride,
4-[N-[[2-(4-Chlorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine trihydrochloride,
4-[N-[[2-(4-Chlorophenyl)pyridin-4-yl]methyl]-N-(4-methoxyphenyl)amino]-1-[[2-(4-chlorophenyl)pyridin-4-yl]methyl]piperidine trihydrochloride, and salts thereof and hydrates thereof.

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Cyclic amine compounds and pharmaceutical composition containing the same

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Cyclic amine compounds and pharmaceutical composition containing the same

Life of this patent

Abstract

Claims6