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Last Updated: March 28, 2024

Claims for Patent: RE30811


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Summary for Patent: RE30811
Title: Substituted piperidines therapeutic process and compositions
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.
Inventor(s): Dykstra; Stanley J. (Evansville, IN), Minielli; Joseph L. (Evansville, IN)
Assignee: Mead Johnson & Company (Evansville, IN)
Application Number:06/098,008
Patent Claims: 1. 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.

2. The process of claim 1 in which the compound is 4-methoxy-2'[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

3. The process of claim 1 in which the compound is 4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide hydrochloride.

4. The process of claim 1 in which the compound is 4-chloro-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

5. The process of claim 1 in which the compound is 2'-[2(1-methyl-2-piperidyl)ethyl]benzanilide.

6. 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 .]. .Iadd.R.sup.10 .Iaddend. 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.

7. The process of claim 6 in which the compound is 2'-[3-(1-methyl-2-piperidyl)propyl]p-anisanilide.

8. The process of claim 6 in which the compound is 2'-[(1-methyl-2-piperidyl)methyl]-p-anisanilide.

9. 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.

10. The process of claim 9 in which the compound is 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide hydrochloride.

11. 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.

12. The composition of claim 11 in which the active ingredient is 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide.

13. The composition of claim 11 in which the active ingredient is 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide hydrochloride.

14. The composition of claim 11 in which the active ingredient is 4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

15. The composition of claim 11 in which the active ingredient is 4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide hydrochloride.

16. The composition of claim 11 in which the active ingredient is 4-chloro-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

17. The composition of claim 11 in which the active ingredient is 2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

18. 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.

19. The composition of claim 18 in which the active ingredient is 2'-[3-(1-methyl-2-piperidyl)propyl]-p-anisanilide.

20. The composition of claim 18 in which the active ingredient is 2'-[(1 -methyl-2-piperidyl)methyl]-p-anisanilide. .Iadd. 21. 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. .Iaddend..Iadd. 22. 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. .Iaddend.

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