USRE30811EExpiredUtility

Substituted piperidines therapeutic process and compositions

Assignee: BRISTOL MYERS COPriority: Mar 3, 1971Filed: Nov 28, 1979Granted: Dec 1, 1981

Est. expiryMar 3, 1991(expired)· nominal 20-yr term from priority

Inventors:Stanley J. Dykstra Joseph L. Minielli

C07D 211/02C07D 213/50C07D 211/28C07D 213/40C07D 211/78C07D 211/26C07D 213/26C07D 213/38C07D 213/30C07D 211/22C07D 213/82C07D 211/60

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References

Claims

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.

Claims

exact text as granted — not AI-modified

What is claimed is: 
     
       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 1  represents hydrogen R 2  represents hydrogen or methylenedioxy attached in the benzenoid 4,5-position   R 3  represents hydrogen or methyl   R 4  represents hydrogen   R 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 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&#39;[2-(1-methyl-2-piperidyl)ethyl]benzanilide. 
     
     
       3. The process of claim 1 in which the compound is 4-methoxy-2&#39;-[2-(1-methyl-2-piperidyl)ethyl]benzanilide hydrochloride. 
     
     
       4. The process of claim 1 in which the compound is 4-chloro-2&#39;-[2-(1-methyl-2-piperidyl)ethyl]benzanilide. 
     
     
       5. The process of claim 1 in which the compound is 2&#39;-[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 8  represents lower alkyl of 1 to 4 carbon atoms inclusive; R 9  is selected from the group consisting of cinnamoyl or ##STR41## wherein .[.Rd 10  .]. .Iadd.R 10  .Iaddend. is methoxy;   A is a divalent radical selected from the group consisting of --CH 2  --, ##STR42## and --(CH 2 ) 3  --; and a pharmaceutically acceptable salt thereof.   
     
     
       7. The process of claim 6 in which the compound is 2&#39;-[3-(1-methyl-2-piperidyl)propyl]p-anisanilide. 
     
     
       8. The process of claim 6 in which the compound is 2&#39;-[(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&#39;-[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&#39;-[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 1  represents hydrogen; R 2  represents hydrogen or methylenedioxy attached in the benzenoid 4,5-position;   R 3  represents hydrogen or methyl; R 4  represents hydrogen;   R 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 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&#39;-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide. 
     
     
       13. The composition of claim 11 in which the active ingredient is 2&#39;-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide hydrochloride. 
     
     
       14. The composition of claim 11 in which the active ingredient is 4-methoxy-2&#39;-[2-(1-methyl-2-piperidyl)ethyl]benzanilide. 
     
     
       15. The composition of claim 11 in which the active ingredient is 4-methoxy-2&#39;-[2-(1-methyl-2-piperidyl)ethyl]benzanilide hydrochloride. 
     
     
       16. The composition of claim 11 in which the active ingredient is 4-chloro-2&#39;-[2-(1-methyl-2-piperidyl)ethyl]benzanilide. 
     
     
       17. The composition of claim 11 in which the active ingredient is 2&#39;-[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 8  represents lower alkyl of 1 to 4 carbon atoms inclusive; R 9  is selected from the group consisting of cinnamoyl or ##STR46## wherein R 10  is methoxy;   A is a divalent radical selected from the group consisting of --CH 2  --, ##STR47## and --(CH 2 ) 3  --; and a pharmaceutically acceptable salt thereof.   
     
     
       19. The composition of claim 18 in which the active ingredient is 2&#39;-[3-(1-methyl-2-piperidyl)propyl]-p-anisanilide. 
     
     
       20. The composition of claim 18 in which the active ingredient is 2&#39;-[(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&#39;-[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&#39;-[2-(1-methyl-2-piperidyl)ethyl]benzanilide. .Iaddend.

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