Substituted N-phenylpiperidines and drugs therefrom

• US 5,296,485 A
• Filed: 03/11/1992
• Issued: 03/22/1994
• Est. Priority Date: 05/31/1991
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Schult, Sabine, Lubisch, Wilfried, Behl, Berthold, Kirchengast, Michael
• Primary Examiner(s): Ivy, C. Warren
• Assistant Examiner(s): Chang, Celia
• Application Number:
  US07/849,250
• Time in Patent Office: 741 Days
• Field of Search: 546/193, 546/194, 546/217, 546/191, 546/237, 546/223, 546/229, 546/186, 546/150, 544/360, 544/1, 514/255, 514/307, 514/316, 514/317, 514/318, 514/183
• US Class Current: 514/316
• CPC Class Codes: C07D 211/26 with hydrocarbon radicals, substituted by nitrogen atoms
• CPC Class Codes: C07D 211/56 Nitrogen atoms nitro radicals C07D211/38
• CPC Class Codes: C07D 211/58 attached in position 4
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

Substituted N-phenylpiperidines I ##STR1## (R¹ =H, NO₂, CN, halogen, C₁ -C₄ -alkyl, CF₃, OCF₃, OH, CH₂ OH, COOH, CHO, NH--CHO, NH₂, CO--NH₂, 5-tetrazinyl, R⁴ --O--, R⁴ --O--CH₂ --, R⁴ O--CO--, R⁴ --CO--, R⁴ --NH--CO, R⁴ --CO--NH--, R⁴ --SO₂ --NH--;

R² =H, NO₂, halogen, C₁ -C₄ -alkyl or R⁴ --O--; ##STR2## R⁴ =C₁ -C₄ -alkyl or phenyl which can carry one of the R² radicals;

R⁵, R⁶ =H or one of the R⁴ radicals; R⁷ =one of the R¹ radicals;

n=0 or 1; m=1 or 2; with the proviso that R³ is ##STR3## only when n is 1, and the optical isomers in the case of optical isomerism, and the physiologically tolerated acid addition salts, are suitable as drugs.

Claims

1. A substituted N-phenylpiperidine of the formula I ##STR41## where R¹ is hydrogen, nitro, cyano, halogen, C₁ -C₄ -alkyl, trifluoromethyl, trifluoromethoxy, hydroxyl, hydroxymethyl, hydroxycarbonyl, formyl, formylamino, amino, aminocarbonyl, 5-tetrazinyl, R⁴ --O--, R⁴ --O--CH₂ --, R⁴ --O--CO--, R⁴ --CO--, R⁴ --NH--CO, R⁴ --CO--NH--, R⁴ --SO₂ --NH--;

R² is hydrogen, nitro, halogen, C₁ -C₄ -alkyl or R⁴ --O--;

R³ is one of the following;

##STR42## R⁴ is C₁ -C₄ -alkyl or phenyl which may carry one of the R² radicals;

R⁵ and R⁶ are each hydrogen, C₁ -C₄ -alkyl or phenyl which can carry one of the R² radicals;

R⁷ is one of the R¹ radicals

n is 0 or 1;

m is 1 or 2;

with the proviso that R³ can be ##STR43## only when n is 1, and the optical isomers when there is optical isomerism, and the physiologically tolerated acid addition salts.

2. A pharmaceutical composition which contains as the active substance, 0.1 to 90% by weight of a substituted N-phenylpiperidine of the formula I as claimed in claim 1.

3. An antiarrythmic composition containing conventional auxiliaries and a therapeutically effective amount of an N-phenylpiperidine of the formula I as claimed in claim 1.