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Claims for Patent: 3,931,195

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Claims for Patent: 3,931,195

Title: Substituted piperidines
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:05/384,341
Patent Claims: 1. A compound selected from the group consisting of substituted piperidines having Formula I and Formula XII ##SPC22## ##SPC23##

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 cinnamoyl or ##SPC24##

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;

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 ##SPC25##

wherein

R.sup.10 is methoxy;

A is a divalent radical selected from the group consisting ##EQU3## --(CH.sub.2).sub.3 --; and a pharmaceutically acceptable salt thereof.

2. The compound of the group defined in claim 1 which is 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide.

3. The compound of the group defined in claim 1 which is 2'-[2-(1-methyl-2-piperidyl)ethyl]cinnamanilide hydrochloride.

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

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

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

7. The compound of the group defined in claim 1 which is 2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide hydrochloride.

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

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

10. The compound of the group defined in claim 1 which is 4-(methylthio)-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

11. The compound of the group defined in claim 1 which is 4-(methylthio)-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide hydrochloride.

12. The compound of the group defined in claim 1 which is 3-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

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

14. The compound of the group defined in claim 1 which is 4-dimethylamino-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

15. A compound selected from the group consisting of substituted piperidines having Formula XII ##SPC26##

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 ##SPC27##

wherein

R.sup.10 is methoxy;

A is a divalent radical selected from the group consisting ##EQU4## and a pharmaceutically acceptable salt thereof.

16. The compound of the group defined in claim 1 which is 2'-[3-(1-methyl-2-piperidyl)propyl]-p-anisanilide.

17. The compound of the group defined in claim 1 which is 2'-[(1-methyl-2-piperidyl)methyl]-p-anisanilide.

18. The compound of the group defined in claim 1 which is 4-methoxy-2'-[2-(1-methyl-2-piperidyl)propyl]benzanilide.

19. The compound of the group defined in claim 1 which is 2'-[1-hydroxy-3-(1-methyl-2-piperidyl)propyl]-p-anisanilide.

20. The compound of the group defined in claim 1 which is 3,4-dimethoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

21. The compound of the group defined in claim 1 which is 2'-[2-(1-methyl-2-piperidyl)ethyl]-3,4,5-trimethoxybenzanilide.

22. The compound of the group defined in claim 1 which is 2'-[2-(2-piperidyl)ethyl]-p-anisanilide.

23. The compound of the group defined in claim 1 which is 2'-[2-(1-methyl-2-piperidyl)ethyl]-p-toluanilide.

24. The compound of the group defined in claim 1 which is 4-(t-butyl)-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

25. The compound of the group defined in claim 1 which is 3,5-dimethoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide.

26. The compound of the group defined in claim 1 which is 4-methoxy-4',5'-methylenedioxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanili de.

27. The compound of the group defined in claim 1 which is 2'-[1-(1-methyl-2-piperidyl)ethyl]-p-anisanilide.

28. A compound selected from the group consisting of substituted piperidines having the formula ##SPC28##

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.
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