Substituted piperidines therapeutic process and compositions
AssigneeMead Johnson & Company
InventorsStanley J. Dykstra, Joseph L. Minielli
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Abstract
The compounds are of the heterocyclic class of 2-phenethylpiperidines having an amido substituent in the ortho position of the phenethyl moiety. Substituents in the ortho position include formamido, benzamido, cinnamamido, 2-thiophenecarboxamido, alkanesulfonamido and alkanoylamido. They are useful as antiarrhythmic and/or antiserotonin agents. The novel compounds are prepared by reaction of appropriately substituted o-aminophenethylpiperidines and the carbonyl or sulfonyl halides or anhydrides. Typical embodiments of this invention are 4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide and 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide.
Claims22
A process for eliciting an antiarrhythmic effect in a mammal in need of said effect which comprises systemic administration to said mammal of a non-toxic effective antiarrhythmic dose of from about 0.01 to 20 mg./kg. of body weight of said mammal of a compound from the group consisting of a substituted piperidine having Formula I ##STR38## wherein R.sup.1 represents hydrogen
- R.sup.2 represents hydrogen or methylenedioxy attached in the benzenoid 4,5-position
- R.sup.3 represents hydrogen or methyl
- R.sup.4 represents hydrogen
- R.sup.5 is selected from the group consisting of lower alkanoyl of from 1 to 4 carbon atoms inclusive, lower alkanesulfonyl of from 1 to 4 carbon atoms inclusive, cinnamoyl, ##STR39## wherein R.sup.7 is selected from the group consisting of hydrogen, chlorine, dimethylamino, alkylthio of from 1 to 4 carbon atoms inclusive, alkyl of from 1 to 4 carbon atoms inclusive, methoxy, 3,4-dimethoxy, 3,5-dimethoxy, and 3,4,5-trimethoxy;
- and a pharmaceutically acceptable salt thereof.
A process for eliciting an antiarrhythmic effect in a mammal in need of said effect which comprises systemic administration to said mammal of a non-toxic effective dose of from about 0.01 to 20 mg./kg. of body weight of said mammal of a compound selected from the group consisting of a substituted piperidine having Formula XII ##STR40## wherein R.sup.8 represents lower alkyl of 1 to 4 carbon atoms inclusive;
- R.sup.9 is selected from the group consisting of cinnamoyl or ##STR41## wherein [Rd.sup.10 ] R.sup.10 is methoxy;
- A is a divalent radical selected from the group consisting of --CH.sub.2 --, ##STR42## and --(CH.sub.2).sub.3 --;
- and a pharmaceutically acceptable salt thereof.
A process for eliciting an antiserotonin effect in a mammal in need of said effect which comprises systemic administration to said mammal of a non-toxic antiserotonin effective dose of from about 0.01 to 20 mg./kg. of body weight of said host of the compound 2'-[2-(1-methyl-2-piperidyl)ethyl]-cinnamanilide or a pharmaceutically acceptable acid addition salt thereof.
A pharmaceutical composition in dosage unit form suitable for systemic administration to a mammal comprising a pharmaceutical carrier containing from 1 to 500 milligrams of an active ingredient selected from the group consisting of a compound having Formula I ##STR43## wherein R.sup.1 represents hydrogen;
- R.sup.2 represents hydrogen or methylenedioxy attached in the benzenoid 4,5-position;
- R.sup.3 represents hydrogen or methyl;
- R.sup.4 represents hydrogen;
- R.sup.5 is selected from the group consisting of lower alkanoyl of from 1 to 4 carbon atoms inclusive, lower alkanesulfonyl of from 1 to 4 carbon atoms inclusive, cinnamoyl, ##STR44## wherein R.sup.7 is selected from the group consisting of hydrogen, chlorine, dimethylamino, alkylthio of from 1 to 4 carbon atoms inclusive, alkyl of from 1 to 4 carbon atoms inclusive, methoxy, 3,4-dimethoxy, 3,5-dimethoxy, and 3,4,5-trimethoxy
- and a pharmaceutically acceptable salt thereof.
A pharmaceutical composition in dosage unit form suitable for systemic administration to a mammal comprising a pharmaceutical carrier containing 1 to 500 milligrams of active ingredient selected from the group consisting of a compound having Formula XII ##STR45## wherein R.sup.8 represents lower alkyl of 1 to 4 carbon atoms inclusive;
- R.sup.9 is selected from the group consisting of cinnamoyl or ##STR46## wherein R.sup.10 is methoxy;
- A is a divalent radical selected from the group consisting of --CH.sub.2 --, ##STR47## and --(CH.sub.2).sub.3 --;
- and a pharmaceutically acceptable salt thereof.
A process for eliciting an antiarrhythmic effect in a mammal in need of said effect which comprises systemic administering to said mammal of a non-toxic effective antiarrhythmic dose of from about 0.01 to 20 mg./kg. of body weight of said mammal of 4-hydroxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.
A pharmaceutical composition in dosage unit form suitable for systemic administration to a mammal comprising a pharmaceutical carrier containing from 1 to 500 milligrams of an active ingredient consisting of 4-hydroxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.
Dependencies are inferred from the claim text.