N-benzylpiperidine amides

• US 5,028,616 A
• Filed: 09/05/1989
• Issued: 07/02/1991
• Est. Priority Date: 09/05/1989
• Status: Expired due to Fees

• Current Assignee: GD Searle LLC (Pfizer Inc.)
• Original Assignee: GD Searle LLC (Pfizer Inc.)
• Inventors: Fowler, Kerry W., Desai, Bipinchandra N.
• Primary Examiner(s): Ramsuer, Robert W.
• Assistant Examiner(s): Haley, Jacqueline
• Application Number:
  US07/402,951
• Time in Patent Office: 665 Days
• Field of Search: 514/321, 514/329, 546/197, 546/224
• US Class Current: 514/321
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links

Abstract

N-benzylpiperidine amides, which have activity as Class III antiarrhythmic agents, acting by prolonging cardiac action potential repolarization. The invention further provides for compositions incorporating the compounds and methods of their use, as well as providing for pharmaceutically acceptable salts of the compounds.

Claims

1. A compound of the formula ##STR27## or the pharmaceutically acceptable non-toxic salts thereof, or the hydrated forms thereof, wherein R¹ benzodioxolyl;

R² is absent or is an alkyl from 1-10 carbon atoms;

n is an integer of from zero to three; and

R³ and R⁴ are independently hydrogen, halogen, halogen substituted alkyl of from one to ten carbon atoms in length, arylalkoxy of from one to ten carbon atoms in length wherein aryl may be substituted by halogen or alkyl of one to ten carbon atoms in length, or alkoxy of one to ten carbon atoms in length.

2. The compound as claimed in claim 1, wherein n is one.

3. The compound as claimed in claim 1, wherein R³ is alkoxy.

4. The compound as claimed in claim 2, wherein R³ is methoxy.

5. The compound as claimed in claim 3, wherein R³ is para-methoxy.

6. The compound as claimed in claim 1, wherein R⁴ is hydrogen.

7. A compound as claimed in claim 1, of the formula ##STR28##

8. A compound as claimed in claim 1, of the formula ##STR29##

9. A pharmaceutical composition useful for regulating cardiac arrhythmias comprising an effective amount of a compound according to claim 1, together with one or more non-toxic pharmaceutically acceptable carriers.

10. The composition as claimed in claim 9, wherein said compound is N-[1-(phenylmethyl)-4-piperidinyl]-1,3-benzodioxole-5-carboxamide.

11. The composition as claimed in claim 9, wherein said compound is N-[1-[(4-methylphenyl)methyl]-4-piperidinyl]-1,3-benzodioxole-5-carboxamide.

12. A method of regulating cardiac arrhythmias in a mammal, comprising administering to said mammal a pharmacologically effective amount of a compound as claimed in claim 1.

13. The method as claimed in claim 12, wherein said compound is N-[1-(phenylmethyl)-4-piperidinyl]-1,3-benzodioxole-5-carboxamide.

14. The method as claimed in claim 12, wherein said compound is N-[1-[(4-methoxyphenyl)methyl]-4-piperidinyl]-1,3-benzodioxole-5-carboxamide.

15. A method of prolonging repolarization of cardiac cells during a cardiac action potential, comprising administering to such mammal a pharmacologically effective amount of a compound as claimed in claim 1.