US 6,191,135 B1Granted

Neurokinin antagonists

AssigneeBoehringer Ingelheim GmbH

InventorsHorst Dollinger, Gerd Schnorrenberg, Hans Briem, Birgit Jung, Georg Speck

Life of this patent

Estimating the term…

Abstract

The invention relates to new compounds of general formula and the pharmaceutically acceptable salts thereof, wherein A, B, Z, R1, R2, R3 and m are defined as in the specification, processes for preparing them and pharmaceutical compositions containing these compounds. The compounds are valuable neurokinin (tachykinin) antagonists.

Claims9

Dependent claims

A compound selected from:

3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl]-amine;
N-3,5-Bistrifluoromethylbenzyl-N-[2-(2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl]-acetamide;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-phenylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[(2-phenyl-2-(4-(2,6-dimethylphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-hydroxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-methoxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(3-methoxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-methoxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2,4-dimethoxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(3,5-dimethoxyphenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-(methylthio)phenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-fluorophenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-fluorophenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-trifluoromethylphenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-nitrophenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-chlorobenzyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(3,4-methylenedioxybenzyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(9-fluorenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-methylphenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2,3-dimethylphenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-chlorophenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-benzylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(1-phenylethyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-benzhydrylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-phenylethyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-phenylethyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(3,4-methylenedioxybenzyl)-piperazine-1-yl)-ethyl]-amine
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-pyridyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-quinolinyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-methylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-methylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(1-propyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-allylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-propyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-cyclopentylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-cyclohexyl-piperazine-1-yl)-ethyl]-amine;
2-Methoxybenzyl-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
2-Chlorobenzyl-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
1-(3,4-Dichlorophenyl)-2′-(2-methoxyphenyl)-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine;
3,5-Bistrifluoromethylbenzyl-[2-(3-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(4-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(3,4,5-trimethoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(4-methylphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[3-phenyl-2-(4-cyclohexylpiperazine-1-yl)-propyl]-amine;
3,5-Bistrifluoromethylbenzyl-[3,3-diphenyl-2-(4-cyclohexylpiperazine-1-yl)-propyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-naphthyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(4-chlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(3,4-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl]-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(4-fluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl[]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-trifluoromethylhenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(3,5-bistrifluoromethylphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-cyclohexylethyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-indanyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(1,2,3,4-tetrahydronaphth-2-yl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-hydroxyethyl)-piperazine-1-yl)-ethyl]-amine;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-3,5-bistrifluoromethylbenzamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-phenylacetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(4-methoxyphenyl)-acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(4-chlorophenyl)-acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,4-dichlorophenyl)-acetamide;
N-[2-(3,4-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-[3-(2-propyloxy)-phenyl]-acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(-2-trifluoromethylphenyl)-acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
2-(3,5-Bistrifluoromethylphenyl)-2-(2-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-diethylamine;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-3,5-bistrifluoromethylbenzamide;
2-(3,5-Bistrifluoromethylphenyl)-2′-(2-methoxyphenyl)-2′-(4-cycloheptylpiperazine-1-yl)-diethylamine;
N-[2-(3,4-dichlorophenyl)-2-(4-(2-phenylethyl)-piperazine-1-yl)-ethyl]-2-[3-(2-propyloxy)-phenyl]-acetamide;
N-[2-(2-Methoxyphenyl)2-(4-(2-indanyl)piperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-([2-(2-Methoxyphenyl)-2-(4-(1,2,3,4-tetrahydronaphth-2-yl)piperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-cyclohexylhomopiperazine-1-yl)-ethyl]-amine;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylhomopiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethyl-phenyl)-acetamide;
2-(3,5-Bistrifluoromethylphenyl)-2′-phenyl-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine
N-Phenyl-N′-[2-phenyl-2-(4-methylpiperazine-1-yl)-ethyl]-urea;
N-2-Methoxyphenyl-N′-[2-phenyl-2-(4-methylpiperazin-1-yl)-ethyl]-urea;
N-2-Chlorophenyl)-N′-[2-phenyl-2-(4-methylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-methylpiperazine-1-yl)-ethyl]-urea;
N-Phenyl-N′-[2-(2-methoxyphenyl)-2-(4-methylpiperazine-1-yl)-ethyl)-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-methylpiperazin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(1-propyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-allylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-propyl)piperazin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cyclopentylpiperazine-1-yl)-ethyl]-urea;
N-Phenyl-N′-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-2-Chlorophenyl-N′-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-2-Methoxyphenyl-N′-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(3,4-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluormethylphenyl-N′-[3-phenyl-2-(4-cyclohexylpiperazine-1-yl)-prop-1-yl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[3,3-diphenyl-2-(4-cyclohexylpiperazine-1-yl)-prop-1-yl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cycloheptylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-cyclohexylethyl)piperazine-1-yl)-ethyl]-urea;
N-Phenyl-N′-[2-phenyl-2-(4-phenylpiperazine-1-yl)-ethyl)-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-phenylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2,6-dimethylphenyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-hydroxyphenyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-methoxyphenyl)piperazine-1-yl-ethyl)-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(3-methoxyphenyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′[-2-phenyl-2-(4-(4-methoxyphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2,4-dimethoxyphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(3,5-dimethoxyphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-methylthio)phenyl)piperazine-1-yl)-ethyl)-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-fluorophenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(4-fluorophenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(4-trifluoromethylphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(4-nitrophenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(4-chlorobenzyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(3,4-methylenedioxybenzyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(9-fluorenyl)piperazine-1-yl)-ethyl)-urea;
N-Phenyl-N′-[2-2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl)-urea;
N-2-Chlorophenyl-N′-[2-2-methoxyphenyl-2-4-(phenylpiperazine-1-yl)-ethyl]-urea;
N-2-Methoxyphenyl-N′-[2-2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl)]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-2-methylphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl-2-(4-(2,3-dimethylphenyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl-2-(4-(2-chlorophenylipiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4 benzyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl-2-(4-benzylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(3,4-methylenedioxybenzyl-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-phenylethyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethyl-phenyl-N′-[2-(2-methoxyphenyl-2-(4-2-phenylethyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-2-methoxyphenyl)-2-(4-(1-phenylethyl)-piperazine-1-yl)-ethyl]-urea;
N-Phenyl-N′-[2-(2-methoxyphenyl)-2-(4-benzhydrylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-[4-2-indanyl)piperazine-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′[-2-(2-methoxyphenyl-2-(4-1,2,3,-tetrahydronaphth-2-yl)piperazine-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′[-2-(2-methoxyphenyl)-2-(4-benzhydrylpiperazine-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-pyridyl)piperazine-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-pyrimidyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-quinolinyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cyclohexylhomopiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-(4-chlorophenyl)ethyl)piperazine-1-yl)ethyl]-urea
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-(4-chlorophenyl)ethyl)piperazine-1-yl)-ethyl]-amine;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-(4-methoxyphenyl)ethyl)piperazine-1-yl)ethyl]-urea;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-(4-methoxyphenyl)ethyl)piperazine-1-yl)ethyl]-amine;
N-[2-Phenyl-2-(4-(2-cyclopropylethyl)piperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethyl-phenyl)-acetamide;
N-[2-Phenyl-2-(4-(2-phenylpropyl)piperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethyl-phenyl)-acetamide;
N-[2-Phenyl-2-(4-ethylpiperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-[2-Thien-3-yl-2-(4-cyclohexylpiperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-[2-Thien-2-yl-2-(4-cyclohexylpiperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-[2-Phenyl-2-(4-(2-(3,4-dichlorophenyl)ethyl)piperazine-1-yl)ethyl]-2-(3,5-bistrifluoro-methylphenyl)-acetamide;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2-methoxyphenyl);-2-(4-cyclohexylpiperazine-1-yl)-diethylamine;
N-[2-(3,4-Dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoro-methylphenyl)acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3-(2-propyloxy)phenyl)acetamide;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2,6-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)ethyl]-urea;
N-[2-(2,6-Dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
3,5-Bistrifluoromethylbenzyl-[2-(2,6-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2,3-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)ethyl]-urea;
3,5-Bistrifluoromethylbenzyl-[2-(2,3-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
N-[2-(2,3-Dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(1-naphthyl)-2-(4-cyclohexylpiperazine-1-yl)ethyl]-urea
N-[2-(1-Naphthyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2,3-dichlorophenyl)-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2,3-dichlorophenyl)-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2,6-dichlorophenyl)-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-dimethylphenyl)acetamide;
N-[2-(3,4-Dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-dimethylphenyl)acetamide;
N-[2-(2,6-Difluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-[2-(2-Fluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-[2-(3-Fluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-(2,3-Difluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-[2-(3,5-Difluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-Phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide
and the pharmaceutically acceptable salts thereof.

161 more elements

A compound selected from:

N-[2-(2-Methoxyphenyl)-2-piperidin-1-yl-ethyl]-3,5-bistrifluoromethylbenzamide;
N-[2-(2-Methoxyphenyl)-2-piperidin-1-yl-ethyl]-2-phenylacetamide;
2-Phenyl-2′-(2-methoxyphenyl)-2′-piperidin-1-yl-diethylamine;
N-[2-(2-Methoxyphenyl)-2-piperidin-1-yl-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
2-(3,5-Bistrifluoromethylphenyl)-2′-(2-methoxyphenyl)-2′-piperidine-1-yl-diethylamine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(2-methylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(3-methylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-methylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(3,5-dimethylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-hydroxypiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(3-phenylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(3-phenylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-phenylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-benzylpiperidine-1-yl)-ethyl)-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-cyclohexylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(3-hydroxypiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-piperidin-1-yl)-piperidin-1-yl)-ethyl]-amine;
N-[2-(2-Methoxyphenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-3,5-bistrifluoromethyl-benzamide;
N-[2-(2-Methoxyphenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethyl-phenyl)-acetamide;
N-[2-(3,4-Dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
3,5-Bistrifluoromethylbenzyl-(2-(3,4-dichlorophenyl)-2-(4-(piperidine-1-yl)-piperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-(2-(2-methoxyphenyl)-2-(4-(3-indolyl)-piperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-isoindolinyl)-piperidine-1-yl)-ethyl]-amine;
N-[2-(2-Methoxyphenyl)-2-(4-(2-isoindolinyl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethyl-phenyl)-acetamide;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(1,2,3,4-tetrahydroisoquinoline-2-yl)piperidine-1-yl)-ethyl]-amine;
N-[2-(2-Methoxyphenyl)-2-(4-(1,2,3,4-tetrahydroisoquinoline-2-yl)-piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-Phenyl-N′-[2-(2-methoxyphenyl)-2-(piperidin-1-yl)-ethyl]-urea;
N-2,5-Dimethylphenyl-N′-[2-(2-methoxyphenyl-2-piperidin-1-yl)-ethyl]-urea;
N-2-Methylphenyl-N′-[2-(2-methoxyphenyl)-2-(piperidin-1-yl)-ethyl]-urea;
N-2-Chlorophenyl-N′-[2-(2-methoxyphenyl)-2-(piperidin-1-yl)-ethyl]-urea;
N-3,4-Dichlorophenyl-N′-[2-(2-methoxyphenyl)-2-(piperidin-1-yl)-ethyl]-urea;
N-2-Methoxyphenyl-N′-[2-(2-methoxyphenyl)-2-(piperidin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-piperidin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(piperidin-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(2-methylpiperidin-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(3-methylpiperidin-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-methylpiperidin-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cyclohexylpiperidin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-5,dimethylpiperidin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(3-phenylpiperidin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-phenylpiperidin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-benzylpiperidin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-(2-(2-methoxyphenyl)-2-(4-piperidin-1-yl)-piperidin-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-4-dichlorophenyl)-2-(4-piperidin-1-yl)-piperidin-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl-2-(4-(2-isoindolinyl)-piperidin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-piperidin-1-yl)-ethyl]-urea;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(3-hydroxymethylpiperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-hydroxyethyl)piperidine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(1-naphthyl)-2-(4-cyclohexylpiperidine-1-yl)-ethyl]-amine;
N-[2-(2-Methoxyphenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3-(2-propyloxy)phenyl)acetamide;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-propylpiperidine-1-yl)-ethyl]-urea;
N-[2-(3,4-Dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3-(2-propyloxy)phenyl)acetamide;
1-(3,5-Bistrifluoromethylphenyl)-2′-(3,4-dichlorophenyl)-2′-(4-(piperidine-1-yl)piperidine-1-yl)-diethylamine;
1-(3,5-Bistrifluoromethylphenyl)-2′-(3,4-dichlorophenyl)-2′-(4-(piperidine-1-yl)piperidine-1-yl)-diethylamine;
N-[2-(3,4-Dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-dimethyl-phenyl)acetamide
N-[2-(2-Methoxyphenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-dimethylphenyl)acetamide;
3,5-Bistrifluoromethylbenzyl-[2-(2,6-dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-amine;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2,6-dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)ethyl]-urea;
N-[2-(2,6-Dichlorophenyl)2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2,3-dichlorophenyl)-2′-(4-(piperidine-1-yl)piperidine-1-yl)-diethylamine;
N-[2-(2,3-Dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluorimethylphenyl)acetamide;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2,6-dichlorophenyl)-2′-(4-(piperidine-1-yl)piperidine-1-yl)-diethylamine;
3,5-Bistrifluoromethylbenzyl-[2-(2,3-dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-amine;
N-[2-(3,4-Dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-3,5-bistrifluoromethylbenzamide;
N-[2-(2-Fluorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-(3-Fluorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-(4-Fluorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-(2,3-Difluorophenyl)-2-(4-(piperidine1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-(3,4-Difluorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
2-(3,5-Bistrifluoromethylphenyl)-2′-(3,4-dichlorophenyl)-2′-(4-(piperidine-1-yl)piperidine-1-yl)-diethylamine;
N-[2-(2,4-Difluorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-(3,4-Dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-N-methyl-3,5-bistrifluoromethylbenzamide;
N-[2-(3,4-Dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-N-methyl-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-(2,3-Methylendioxyphenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-[2-(3,4-Methylendioxyphenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
2-(3,5-Bistrifluoromethylphenyl)-2′-(2,3-methylendioxyphenyl)-2′-(4-(piperidine-1-yl)piperidine-1-yl)-diethylamine;
2-(3,5-Bistrifluoromethylphenyl)-2′-(3,4-methylendioxyphenyl)-2′-(4-(piperidine-1-yl)piperidine-1-yl)-diethylamine;
N-3,5-Bistrifluoromethylbenzyl-N-[2-(2,3-dichlorophenyl)-2-(4-(piperidine-1-yl)piperidine-1-yl)-ethyl]acetamide;
2-(3,5-Bistrifluoromethylphenyl)-2′-(3,4-dichlorophenyl)-2′-(4-(piperidine-1-yl)piperidine-1-yl)diethylmethylamine;
N-[2-(3,4-Dichlorophenyl)-2-(4-(morpholine-4-yl)piperidine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide
and the pharmaceutically acceptable salts thereof.

78 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/499,913Filed 8 Feb 2000 · continuation
Priority: DE 44 33 20817 Sep 1994
Granted: 20 Feb 2001
Term ends: Not estimatedThe source records don’t support an estimate.

Classification33 codes

C07D 213/74
Nitrogen atoms: amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/08
Drugs for disorders of the alimentary tract or the digestive system: for nausea, cinetosis or vertigo; Antiemetics

Family

Application08/473,423Parent of this division · filed 7 Jun 1995
Application08/905,251Parent of this division · filed 2 Aug 1997
Application09/250,342Parent of this continuation · filed 16 Feb 1999
Application09/250,342Parent of this division
US 5,985,881 AParent of this division
US 5,696,123 AParent of this division
US 6,235,732 B1Related patent
US 6,191,135 B1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound selected from:

3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl]-amine;
N-3,5-Bistrifluoromethylbenzyl-N-[2-(2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl]-acetamide;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-phenylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[(2-phenyl-2-(4-(2,6-dimethylphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-hydroxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-methoxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(3-methoxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-methoxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2,4-dimethoxyphenyl)piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(3,5-dimethoxyphenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-(methylthio)phenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-fluorophenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-fluorophenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-trifluoromethylphenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-nitrophenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(4-chlorobenzyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(3,4-methylenedioxybenzyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(9-fluorenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-methylphenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2,3-dimethylphenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-chlorophenyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-benzylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(1-phenylethyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-benzhydrylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-phenylethyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-phenylethyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(3,4-methylenedioxybenzyl)-piperazine-1-yl)-ethyl]-amine
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-pyridyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-quinolinyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-methylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-methylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(1-propyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-allylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-propyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-cyclopentylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-cyclohexyl-piperazine-1-yl)-ethyl]-amine;
2-Methoxybenzyl-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
2-Chlorobenzyl-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
1-(3,4-Dichlorophenyl)-2′-(2-methoxyphenyl)-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine;
3,5-Bistrifluoromethylbenzyl-[2-(3-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(4-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(3,4,5-trimethoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(4-methylphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[3-phenyl-2-(4-cyclohexylpiperazine-1-yl)-propyl]-amine;
3,5-Bistrifluoromethylbenzyl-[3,3-diphenyl-2-(4-cyclohexylpiperazine-1-yl)-propyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-naphthyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(4-chlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(3,4-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl]-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(4-fluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl[]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-trifluoromethylhenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(3,5-bistrifluoromethylphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-cyclohexylethyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-indanyl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(1,2,3,4-tetrahydronaphth-2-yl)-piperazine-1-yl)-ethyl]-amine;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-(2-hydroxyethyl)-piperazine-1-yl)-ethyl]-amine;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-3,5-bistrifluoromethylbenzamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-phenylacetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(4-methoxyphenyl)-acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(4-chlorophenyl)-acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,4-dichlorophenyl)-acetamide;
N-[2-(3,4-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-[3-(2-propyloxy)-phenyl]-acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(-2-trifluoromethylphenyl)-acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
2-(3,5-Bistrifluoromethylphenyl)-2-(2-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-diethylamine;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-3,5-bistrifluoromethylbenzamide;
2-(3,5-Bistrifluoromethylphenyl)-2′-(2-methoxyphenyl)-2′-(4-cycloheptylpiperazine-1-yl)-diethylamine;
N-[2-(3,4-dichlorophenyl)-2-(4-(2-phenylethyl)-piperazine-1-yl)-ethyl]-2-[3-(2-propyloxy)-phenyl]-acetamide;
N-[2-(2-Methoxyphenyl)2-(4-(2-indanyl)piperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-([2-(2-Methoxyphenyl)-2-(4-(1,2,3,4-tetrahydronaphth-2-yl)piperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
3,5-Bistrifluoromethylbenzyl-[2-(2-methoxyphenyl)-2-(4-cyclohexylhomopiperazine-1-yl)-ethyl]-amine;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylhomopiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethyl-phenyl)-acetamide;
2-(3,5-Bistrifluoromethylphenyl)-2′-phenyl-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine
N-Phenyl-N′-[2-phenyl-2-(4-methylpiperazine-1-yl)-ethyl]-urea;
N-2-Methoxyphenyl-N′-[2-phenyl-2-(4-methylpiperazin-1-yl)-ethyl]-urea;
N-2-Chlorophenyl)-N′-[2-phenyl-2-(4-methylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-methylpiperazine-1-yl)-ethyl]-urea;
N-Phenyl-N′-[2-(2-methoxyphenyl)-2-(4-methylpiperazine-1-yl)-ethyl)-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-methylpiperazin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(1-propyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-allylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-propyl)piperazin-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cyclopentylpiperazine-1-yl)-ethyl]-urea;
N-Phenyl-N′-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-2-Chlorophenyl-N′-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-2-Methoxyphenyl-N′-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(3,4-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluormethylphenyl-N′-[3-phenyl-2-(4-cyclohexylpiperazine-1-yl)-prop-1-yl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[3,3-diphenyl-2-(4-cyclohexylpiperazine-1-yl)-prop-1-yl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cycloheptylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-cyclohexylethyl)piperazine-1-yl)-ethyl]-urea;
N-Phenyl-N′-[2-phenyl-2-(4-phenylpiperazine-1-yl)-ethyl)-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-phenylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2,6-dimethylphenyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-hydroxyphenyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-methoxyphenyl)piperazine-1-yl-ethyl)-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(3-methoxyphenyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′[-2-phenyl-2-(4-(4-methoxyphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2,4-dimethoxyphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(3,5-dimethoxyphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-methylthio)phenyl)piperazine-1-yl)-ethyl)-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-fluorophenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(4-fluorophenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(4-trifluoromethylphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(4-nitrophenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(4-chlorobenzyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(3,4-methylenedioxybenzyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(9-fluorenyl)piperazine-1-yl)-ethyl)-urea;
N-Phenyl-N′-[2-2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl)-urea;
N-2-Chlorophenyl-N′-[2-2-methoxyphenyl-2-4-(phenylpiperazine-1-yl)-ethyl]-urea;
N-2-Methoxyphenyl-N′-[2-2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-phenylpiperazine-1-yl)-ethyl)]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-2-methylphenyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl-2-(4-(2,3-dimethylphenyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl-2-(4-(2-chlorophenylipiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4 benzyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl-2-(4-benzylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(3,4-methylenedioxybenzyl-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-phenylethyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethyl-phenyl-N′-[2-(2-methoxyphenyl-2-(4-2-phenylethyl)-piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-2-methoxyphenyl)-2-(4-(1-phenylethyl)-piperazine-1-yl)-ethyl]-urea;
N-Phenyl-N′-[2-(2-methoxyphenyl)-2-(4-benzhydrylpiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-[4-2-indanyl)piperazine-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′[-2-(2-methoxyphenyl-2-(4-1,2,3,-tetrahydronaphth-2-yl)piperazine-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′[-2-(2-methoxyphenyl)-2-(4-benzhydrylpiperazine-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-pyridyl)piperazine-1-yl-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-pyrimidyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-(2-quinolinyl)piperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2-methoxyphenyl)-2-(4-cyclohexylhomopiperazine-1-yl)-ethyl]-urea;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-(4-chlorophenyl)ethyl)piperazine-1-yl)ethyl]-urea
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-(4-chlorophenyl)ethyl)piperazine-1-yl)-ethyl]-amine;
N-3,5-Bistrifluoromethylphenyl-N′-[2-phenyl-2-(4-(2-(4-methoxyphenyl)ethyl)piperazine-1-yl)ethyl]-urea;
3,5-Bistrifluoromethylbenzyl-[2-phenyl-2-(4-(2-(4-methoxyphenyl)ethyl)piperazine-1-yl)ethyl]-amine;
N-[2-Phenyl-2-(4-(2-cyclopropylethyl)piperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethyl-phenyl)-acetamide;
N-[2-Phenyl-2-(4-(2-phenylpropyl)piperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethyl-phenyl)-acetamide;
N-[2-Phenyl-2-(4-ethylpiperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-[2-Thien-3-yl-2-(4-cyclohexylpiperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-[2-Thien-2-yl-2-(4-cyclohexylpiperazine-1-yl)ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide;
N-[2-Phenyl-2-(4-(2-(3,4-dichlorophenyl)ethyl)piperazine-1-yl)ethyl]-2-(3,5-bistrifluoro-methylphenyl)-acetamide;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2-methoxyphenyl);-2-(4-cyclohexylpiperazine-1-yl)-diethylamine;
N-[2-(3,4-Dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoro-methylphenyl)acetamide;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3-(2-propyloxy)phenyl)acetamide;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2,6-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)ethyl]-urea;
N-[2-(2,6-Dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
3,5-Bistrifluoromethylbenzyl-[2-(2,6-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(2,3-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)ethyl]-urea;
3,5-Bistrifluoromethylbenzyl-[2-(2,3-dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-amine;
N-[2-(2,3-Dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-3,5-Bistrifluoromethylphenyl-N′-[2-(1-naphthyl)-2-(4-cyclohexylpiperazine-1-yl)ethyl]-urea
N-[2-(1-Naphthyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2,3-dichlorophenyl)-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2,3-dichlorophenyl)-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine;
1-(3,5-Bistrifluoromethylphenyl)-2′-(2,6-dichlorophenyl)-2′-(4-cyclohexylpiperazine-1-yl)-diethylamine;
N-[2-(2-Methoxyphenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-dimethylphenyl)acetamide;
N-[2-(3,4-Dichlorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-dimethylphenyl)acetamide;
N-[2-(2,6-Difluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-[2-(2-Fluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-[2-(3-Fluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-(2,3-Difluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluormethylphenyl)acetamide;
N-[2-(3,5-Difluorophenyl)-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)acetamide;
N-[2-Phenyl-2-(4-cyclohexylpiperazine-1-yl)-ethyl]-2-(3,5-bistrifluoromethylphenyl)-acetamide
and the pharmaceutically acceptable salts thereof.

161 more elements

Facts

Application

09/499,913Filed 8 Feb 2000 · continuation

Priority

DE 44 33 20817 Sep 1994

Granted

20 Feb 2001

Term ends

Not estimatedThe source records don’t support an estimate.

Classification33 codes

C07D 213/74
Nitrogen atoms: amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/08
Drugs for disorders of the alimentary tract or the digestive system: for nausea, cinetosis or vertigo; Antiemetics

Family

Application08/473,423Parent of this division · filed 7 Jun 1995

Application08/905,251Parent of this division · filed 2 Aug 1997

Application09/250,342Parent of this continuation · filed 16 Feb 1999

Application09/250,342Parent of this division

US 5,985,881 AParent of this division

US 5,696,123 AParent of this division

US 6,235,732 B1Related patent

US 6,191,135 B1This patent

From the US filing history. Foreign family members aren’t listed.