N-[(1-piperidinyl)alkyl]arylcarboxamide derivatives

A chemical compound having the formula:

• ##STR86## wherein the group ##STR87## in a member selected from the group consisting of:
• a. a radical having the formula:
• ##STR88## wherein R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• b. a radical having the formula:
• ##STR89## wherein R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• M is selected from the group consisting of hydrogen, lower alkyl, lower alkylcarbonyl and 2-cyanoethyl;
• Y is selected from the group consisting of O, S and lower alkylcarbonylimino;
• and the dotted line indicates that the double bond between the 3-and 4-carbon atoms of the piperidine nucleus is optional, provided that when there is a double bond between said 3-and 4-carbon atoms, then said Y is O and said M is hydrogen;
• c. a radical having the formula:
• ##STR90## wherein R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• and
• d. a radical having the formula:
• ##STR91## wherein R.sup.5 is selected from the group consisting of hydrogen and methyl;
• R.sup.6 is selected from the group consisting of hydrogen and halo;
• and R.sup.7 is selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl.

A pharmaceutical composition in dosage unit form comprising per dosage unit an effective antiemetic or psychotropic amount of a compound selected from the group consisting of a N-[(1-piperidinyl)alkyl]arylcarboxamide derivative having the formula:

• ##STR92## and the pharmaceutically acceptable acid salts thereof, wherein:
• Ar is an aryl radical selected from the group consisting of phenyl, substituted phenyl, 2-thienyl, 2-furanyl, pyridinyl and 1-methyl-2-pyrrolyl, wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro, hydroxy, amino, lower alkylcarbonyloxy and lower alkylcarbonylamino, provided that when more than 1 of said substituents are present only one thereof may be selected from the group consisting of hydroxy, amino, lower alkylcarbonyloxy and lower alkylcarbonylamino;
• R is a member selected from the group consisting of hydrogen and lower alkyl;
• n is an integer of from 2 to 3 inclusive;
• and ##STR93## is a member selected from the group consisting of a. a radical having the formula:
• ##STR94## wherein R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• b. a radical having the formula:
• ##STR95## wherein R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• M is selected from the group consisting of hydrogen, lower alkyl, lower alkylcarbonyl and 2-cyanoethyl;
• Y is selected from the group consisting of O, S and lower alkylcarbonylimino;
• and the dotted line indicates that the double bond between the 3- and 4-carbon atoms of the piperidine nucleus is optional, provided that when there is a double bond between said 3- and 4-carbon atoms, then said Y is O and said M is hydrogen;
• c. a radical having the formula:
• ##STR96## wherein R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• and
• d. a radical having the formula:
• ##STR97## wherein R.sup.5 is selected from the group consisting of hydrogen and methyl;
• R.sup.6 is selected from the group consisting of hydrogen and halo;
• and R.sup.7 is selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• in admixture with a pharmaceutical carrier.

A method of inhibiting emesis or mental disorders which comprises the systemic administration to warm-blooded animals of an effective antimetic or psychotropic amount of a compound selected from the group consisting of a N-[(1-piperidinyl)alkyl]arylcarboxamide derivative having the formula:

• ##STR98## and the pharmaceutically acceptable acid addition salts thereof, wherein:
• Ar is an aryl radical selected from the group consisting of phenyl, substituted phenyl, 2-thienyl, 2-furanyl, pyridinyl and 1-methyl-2-pyrrolyl, wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, trifluoromethyl, nitro, hydroxy, amino, lower alkylcarbonyloxy and lower alkylcarbonylamino, provided that when more than 1 of said substituents are present only one thereof may be selected from the group consisting of hydroxy, amino, lower alkylcarbonyloxy and lower alkylcarbonylamino;
• R is a member selected from the group consisting of hydrogen and lower alkyl;
• n is an integer of from 2 to 3 inclusive;
• and
• the radical ##STR99## is a member selected from the group consisting of a. a radical having the formula:
• ##STR100## wherein R.sup.1 and R.sup.2 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• b. a radical having the formula:
• ##STR101## wherein R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• M is selected from the group consisting of hydrogen, lower alkyl, lower alkylcarbonyl and 2-cyanoethyl;
• Y is selected from the group consisting of O, S and lower alkylcarbonylimino;
• and the dotted line indicates that the double bond between the 3- and 4-carbon atoms of the piperidine nucleus is optional, provided that when there is a double bond between said 3- and 4-carbon atoms, then said Y is O and said M is hydrogen;
• c. a radical having the formula:
• ##STR102## wherein R.sup.3 and R.sup.4 are each independently selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• and
• d. a radical having the formula:
• ##STR103## wherein R.sup.5 is selected from the group consisting of hydrogen and methyl;
• R.sup.6 is selected from the group consisting of hydrogen and halo;
• and R.sup.7 is selected from the group consisting of hydrogen, halo, lower alkyl and trifluoromethyl;
• in admixture with a pharmaceutical carrier.