IP Library Granted Patent US 8,404,719
Granted Patent B2
US 8,404,719 · App. 13/323,029 · Granted Mar 26, 2013

Substituted piperidinylcarbonylbenzenesulfonamides as calcium channel blockers

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Quick Facts
Patent No.
US 8,404,719
App. No.
13/323,029
Granted
Mar 26, 2013
Kind
B2
Abstract

The present application relates to calcium channel inhibitors comprising compounds of formula (I), formula (II), formula (III), or formula (IV), wherein L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R c are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

Claims (32)

1. A compound of formula (I) or formula (II),

or a pharmaceutically acceptable salt thereof, wherein

R 1 is X, and R 2 is Y;

X is (ii);

G 1 is azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl or azepanyl, wherein G 1 is connected through the nitrogen atom of said azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl or azepanyl;

Y is —NR c Ar 1 , —NR c Ar 2 —Ar 1 , —NR c CH(Ar 1 ) 2 , —NR c (CR a R b ) p CH(Ar 1 ) 2 , —NR c (CR a R b ) p CH(Ar 1 ) 2 , —NR c —G 2 , —NR c —G 2 —Ar 1 , (iii), (iv), (v) or (vi);

Ar 1 , at each occurrence, is independently aryl or heteroaryl, wherein said aryl and heteroaryl are unsubstituted or substituted with 1, 2, 3, 4, or 5 substituents selected from alkoxy, alkyl, cyano, haloalkyl, halogen, or —N(alkyl) 2 ;

Ar 2 is aryl or heteroaryl, wherein said aryl and heteroaryl are unsubstituted or substituted with 1, 2, 3, or 4 substituents selected from alkoxy, alkyl, cyano, haloalkyl, or halogen;

G 2 is cycloalkyl;

R a and R b are at each occurrence independently hydrogen, alkyl, or hydroxyalkyl;

R c is hydrogen or alkyl;

p is 1, 2, 3, or 4; and

R 3 , R 4 , R 5 and R 6 are each independently hydrogen, alkoxy, alkyl, or halogen.

2. The compound according to claim 1 of formula (I), or a pharmaceutically acceptable salt thereof.

3. The compound according to claim 2 of formula (I), or a pharmaceutically acceptable salt thereof, wherein

G 1 is pyrrolidinyl or piperidinyl;

R 2 is Y;

Y is NR c Ar 1 ;

R c is hydrogen; and

Ar 1 is aryl, wherein said aryl is unsubstituted or substituted with 1, 2, or 3 substituents selected from haloalkyl and halogen.

4. The compound according to claim 1 , or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of:

N-(4-fluorophenyl)-3-[(4-pyrrolidin-1-ylpiperidin-1-yl)carbonyl]benzenesulfonamide;

N-phenyl-3-[(4-pyrrolidin-l-ylpiperidin-l-yl)carbonyl]benzenesulfonamide;

3-[(4-pyrrolidin-l-ylpiperidin-l-yl)carbonyl]-N- [4-(trifluoromethyl)phenyl]benzenesulfonamide;

3-[(4-pyrrolidin-l-ylpiperidin-l-yl)carbonyl]-N- [3-(trifluoromethyl)phenyl]benzenesulfonamide;

N-(3-fluorophenyl)-3-[(4-pyrrolidin-1-ylpiperidin-1-yl)carbonyl]benzenesulfonamide;

N-(2-fluorophenyl)-3-[(4-pyrrolidin-1-ylpiperidin-1-yl)carbonyl]benzenesulfonamide;

3-(1,4′-bipiperidin-l′-ylcarbonyl)-N-(4-fluorophenyl)benzenesulfonamide;

3-(1,4′-bipiperidin-l′-ylcarbonyl)-N-(2-fluorophenyl)benzenesulfonamide;

3-(1,4′-bipiperidin-l′-ylcarbonyl)-N-(3-fluorophenyl)benzenesulfonamide; and

3-(1,4′-bipiperidin-l′-ylcarbonyl)-N-[4-(trifluoromethyl)phenyl]benzenesulfonamide

5. A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I) or formula (II) according to claim 1 , or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030237/0597 →