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Details for Patent: 4,000,143

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Details for Patent: 4,000,143

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)
Filing Date:Oct 08, 1975
Application Number:05/620,907
Claims:1. A compound selected from the group consisting of substituted piperidines having Formula I ##STR45## 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, ##STR46## 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] -2-thiophenecarboxanilide.

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

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

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

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

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

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

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

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

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

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

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

14. A compound selected from the group consisting of o-aminophenethylpiperidines having the formula ##STR47## and acid addition salts thereof wherein R.sup.1 represents hydrogen, lower alkyl of from 1 to 4 carbon atoms inclusive;

R.sup.2 represents hydrogen or lower alkoxy of from 1 to 4 carbon atoms inclusive;

R.sup.3 represents a lower alkyl of from 1 to 4 carbon atoms inclusive; and

R.sup.4 represents hydrogen, lower alkyl of from 1 to 4 carbon atoms inclusive, or a dialkyl carboxamido wherein the dialkyl groups have from 1 to 4 atoms inclusive.

15. The compound of the group defined in claim 14 which is 2-(o-aminophenethyl)-1-methylpiperidine.

16. The compound of the group defined in claim 14 which is 2-(o-aminophenethyl)-1-methylpiperidine dihydrochloride.

17. The compound 2-[2-[(p-methoxybenzyl)amino]phenethyl]-1-methylpiperidine hemimucate.
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