Claims for Patent: 3,931,195

Summary 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.