Patent ID: 6218394
Filing Date: 2001-04-17
Classification: A61P,C07C,C07D

Abstract:
A 4-aryl-1-(indanmethyl or dihydrobenzothiophenemethyl)-piperazine compound of Formula I ##STR12##wherein one of X and Y is CH.sub.2 and the other is selected from the group consisting of CH.sub.2 and S;Z is N;Ar is selected from the group consisting of phenyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 2-pyrimidyl, 1-indolyl, 2-indolyl, 3-indolyl, 1-indol-2-onyl, 3-indol-2-onyl, 3-benzofuranyl,3 2-benzothiophenyl, 3-benzothiophenyl, 1-naphthyl, and 2-naphthyl, wherein each Ar group can be optionally substituted with halogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxy, lower alkylsulfonyl, cyano, trifluoromethyl, trifluromethylsulfonyloxy, cycloalkyl, cycloalkyl-lower-alkyl, nitro, amino, lower alkylamino, di-lower alkylamino, acylamino wherein said acyl moiety is selected from the group consisting of formyl, lower alkyl carbonyl, cycloalkyl carbonyl, and cycloalkyl-lower alkyl or C.sub.1-2 alkylenedioxy;R.sup.1 is selected from the group consisting of hydrogen, lower alkyl, lower alkenyl, lower alkynyl, cycloalk(en)yl, cycloalk(en)yl-lower alk(en/yn)yl, phenyl, phenyl-lower alkyl, acyl selected from the group consisting of formyl, lower alkyl carbonyl, cycloalkyl carbonyl, and cycloalkyl-lower alkyl carbonyl, thioacyl wherein said acyl moiety is selected from the group consisting of formyl, lower alkyl carbonyl, cycloalkyl carbonyl, and cycloalkyl-lower alkyl, lower alkylsulfonyl, trifluoromethylsulfonyl, and phenylsulfonyl; orR.sup.1 is a group R.sup.9 VCO-- where V is O or S and R.sup.9 is lower alkyl, cycloalkyl, cycloalkyl-lower-alkyl or phenyl, orR.sup.1 is a group R.sup.10 R.sup.11 NCO-- or R.sup.10 R.sup.11 NCS-- wherein R.sup.10 and R.sup.11 are independently selected from the group consisting of hydrogen, lower alkyl, cycloalkyl, cycloalkyl-lower-alkyl and phenyl, or R.sup.10 and R.sup.11 taken together with the N-atom to which they are linked, form a pyrrolidinyl, piperidinyl or perhydroazepin group;R.sup.2 is hydrogen, lower alkyl, cycloalkyl or cycloalkyl-lower-alkyl; or R.sup.1 and R.sup.2 taken together with the N-atom to which they are linked form a group, ##STR13##wherein Q is C.dbd.O, C.dbd.S or CH.sub.2 ; T is NH, S, O or CH.sub.2 ; and m is 1-4, inclusive;R.sup.3 -R.sup.5 are independently selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkylcarbonyl, phenylcarbonyl, halogen substituted phenylcarbonyl, lower alkoxy, lower alkylthio, hydroxy, lower alkylsulfonyl, cyano, trifluoromethyl, cycloalkyl, cycloalkyl-lower-alkyl and nitro;R.sup.6 and R.sup.7 are each hydrogen or lower alkyl or they can be linked together to form a 3-7 membered carbocyclic ring;R.sup.8 is hydrogen or lower alkyl;wherein any alkyl, cycloalkyl or cycloalkylalkyl group present can be optionally substituted with one or two hydroxy groups, which can be optionally esterified with an aliphatic or aromatic carboxylic acid; and any aryl substituent present can be optionally substituted with halogen, lower alkyl, lower alkoxy, lower alkylthio, hydroxy, lower alkylsulfonyl, cyano, trifluoromethyl, trifluoromethylsulfonyloxy, cycloalkyl, cycloalkyl-lower-alkyl or nitro;or a pharmaceutically acceptable acid addition salt thereof.