Derivatives of piperidinedione for protecting the myocardium presenting an anti-arrythmic activity, and pharmaceutical compositions

• US 4,721,710 A
• Filed: 03/10/1986
• Issued: 01/26/1988
• Est. Priority Date: 11/08/1982
• Status: Expired due to Fees

• Current Assignee: Sanofi
• Original Assignee: Sanofi
• Inventors: Cautreels, Werner, Gautier, Patrick, Bernhart, Claude
• Primary Examiner(s): Ramsuer, Robert W.
• Application Number:
  US06/838,255
• Time in Patent Office: 687 Days
• Field of Search: 544/130, 546/16, 546/112, 546/142, 546/187, 546/193, 514/234, 514/316, 514/318
• US Class Current: 514/235.5
• CPC Class Codes: A61P 9/06 Antiarrhythmics
• CPC Class Codes: C07C 255/00 Carboxylic acid nitriles cyanogen or compounds thereof C01C3/00
• CPC Class Codes: C07D 213/57 Nitriles
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

The present invention relates to derivatives of piperidinedione of formula: ##STR1## in which R is alkyl or forms with N a possibly substituted morpholino or piperidino group, n=2 or 3, R₁, R₂, R₃ and R₄ represent H or lower alkyl; R₃ and R₄ taken together may represent (CH₂)_m where m=4 or 5 and R₂ and R₃ taken together may represent (CH₂)_p where p=3 or 4 and in this case R₁ and R₄ =H, R₅ is H or alkyl. It also relates to a process for manufacturing the product of formula (I) and to the drugs containing a product of formula (I).

Claims

1. Derivatives of piperidinedione represented by the formula:

##STR33## in which;

R represents a straight or branched alkyl group having from 2 to 5 atoms of carbon;

or the group ##STR34## represents a morpholino or piperidino group possibly substituted by 1 to 4 methyl groups;

n=2 or 3;

R₁ and R₂ considered independently represent an atom of hydrogen or a lower alkyl group,

R₃ and R₄ considered independently represent hydrogen or a lower alkyl group;

R₅ designates hydrogen or a lower alkyl group;

the piperidinedione substitutes the pyridyl group in the 2'"'"' position;

or salts of said derivatives with pharmaceutically acceptable acids, and wherein at least one of R₁, R₂, R₃ or R₄ is other than hydrogen.

2. The derivatives of claim 1 in the form of a diastereoisomer or an optical isomer or a mixture of these isomers.

3. The compound of claim 1 wherein R is isopropyl, n is 2, R₁ and R₂ are hydrogen, R₃ and R₄ are methyl, and R₅ is hydrogen.

4. The compound of claim 1 wherein R is isopropyl, n is 2, R₁, R₂ and R₃ are hydrogen, R₄ is isobutyl and R₅ is hydrogen.

5. The compound of claim 1 wherein R is isopropyl, n is 2, R₁, R₂ and R₃ are hydrogen, R₄ is ethyl and R₅ is hydrogen.

6. The compound of claim 1 wherein R is isopropyl, n is 2, R₁, R₂ and R₃ are hydrogen, R₄ is tertiary butyl and R₅ is hydrogen.

7. The compound of claim 1 wherein R is propyl, n is 2, R₁ and R₂ are hydrogen, R₃ and R₄ are methyl, and R₅ is hydrogen.

8. The compound of claim 1 wherein R is isopropyl, n is 3, R₁ and R₂ are hydrogen, R₃ and R₄ are ethyl, and R₅ is hydrogen.

9. A pharmaceutical composition for protection of the myocardium containing a myocardium protecting amount of a compound according to claim 1 together with a pharmaceutically acceptable carrier.