IP Library Granted Patent US 7,348,343
Granted Patent B2
US 7,348,343 · App. 11/521,807 · Granted Mar 25, 2008

Amides useful for treating pain

Assignee: Abbott Laboratories Inc.
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Quick Facts
Patent No.
US 7,348,343
App. No.
11/521,807
Granted
Mar 25, 2008
Kind
B2
Abstract

The present invention relates to compounds of formula (I-VII) or a pharmaceutically acceptable salt or prodrug thereof, in which A, L, R 6 , R 7 and R 8 are defined herein. The present invention also relates to methods of treating pain using these compounds and pharmaceutical compositions including these compounds.

Claims (66)

1. A compound of formula (VII)

wherein

X 1 is N or CR 1 ;

X 5 is N or CR 5 ;

X 6 is a bond or CR 6 ;

X 7 is N or CR 7 ;

X 8 is N or CR 8 ;

X 9 is N or CR 9 ;

R 1 , R 5 , and R 9 are independently selected from the group consisting of hydrogen, alkyl, alkoxy, halogen, haloalkyl and heterocycle;

R 7 is hydrogen, alkenyl, alkoxy, alkoxycarbonyl, alkoxysulfonyl, alkyl, alkylcarbonyl, alkoxycarbonylalkyl, alkylsulfonyl, alkylthio, alkynyl, aryl, arylalkyl, aryloxy, arylthio, cyanoalkyl, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylthio, haloalkoxy, haloalkyl, haloalkylsulfonyl, haloalkylthio, halogen, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heterocycle, heterocyclealkyl, hydroxy, hydroxyalkyl, R C R D N—, (R A R B N)carbonyl-, (R A R B N)sulfonyl-; or R A S(O) 2 —;

R 6 and R 8 are independently hydrogen, lower alkenyl, lower alkoxy, lower alkyl, lower alkylthio, lower alkynyl, lower haloalkoxy, lower haloalkyl, lower haloalkylthio, halogen, hydroxy, mercapto, or R A R B N—;

R A and R B are independently alkyl, hydrogen, haloalkyl, or heterocycle; and

R C and R D are independently hydrogen, alkenyl, alkoxycarbonyl, alkyl, alkylcarbonyl, alkynyl, or (NR A R B )carbonyl.

2. A compound according to claim 1 , wherein

X 1 is CR 1 ;

X 5 is CR 5 ;

X 6 is CR 6 ;

X 7 is CR 7 ;

X 8 is CR 8 ;

X 9 is N or CR 9 ;

R 7 and R 8 are independently selected from the group consisting of hydrogen, alkyl, and halogen.

3. A compound according to claim 2 , that is

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (5-fluoro-pyridin-2-yl)-amide;

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (5-chloro-pyridin-2-yl)-amide;

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (5-bromo-pyridin-2-yl)-amide;

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (5-iodo-pyridin-2-yl)-amide; or

3′-Trifluoromethyl-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (5-iodo-pyridin-2-yl)-amide.

4. The compound according to claim 1 , wherein

X 1 is CR 1 ;

X 5 is CR 5 ;

X 6 is CR 6 ;

X 7 is CR 7 ;

X 8 is N;

X 9 is CR 9 ;

R 5 , R 6 , R 9 and R 1 , are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, and halogen;

R 7 is hydrogen, alkenyl, alkoxy, alkoxycarbonyl, alkoxysulfonyl, alkyl, alkylcarbonyl, alkoxycarbonylalkyl, alkylsulfonyl, alkylthio, alkynyl, aryl, arylalkyl, aryloxy, arylthio, cyanoalkyl, cycloalkyl, cycloalkylalkyl, cycloalkyloxy, cycloalkylthio, haloalkoxy, haloalkyl, haloalkylsulfonyl, haloalkylthio, halogen, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroarylthio, heterocycle, heterocyclealkyl, hydroxy, hydroxyalkyl, R C R D N—, (R A R B N)carbonyl-, (R A R B N)sulfonyl-; or R A S(O) 2 —;

R A and R B are independently alkyl, hydrogen, haloalkyl, or heterocycle; and

R C and R D are independently hydrogen, alkenyl, alkoxycarbonyl, alkyl, alkylcarbonyl, alkynyl, or (NR A R B )carbonyl-.

5. A compound according to claim 4 , that is

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (6-trifluoromethyl-pyridin-3-yl)-amide;

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (6-chloro-pyridin-3-yl)-amide;

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-5′-yl)-amide;

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (6-azepan-1-yl-pyridin-3-yl)-amide; or

3′-Trifluoromethyl-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (6-trifluoromethyl-pyridin-3-yl)-amide.

6. The compound according to claim 1 , wherein

X 1 is CR 1 ;

X 5 is CR 5 ;

X 6 is a bond;

X 7 is N;

X 8 is N;

X 9 is CR 9 ;

R 1 , R 9 and R 5 , are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, and halogen.

7. The compound according to claim 6 , that is

3′-Chloro-3,6-dihydro-2H-[1,2′]bipyridinyl-4-carboxylic acid (1-tert-butyl-1H-pyrazol-4-yl)-amide.

8. A compound according to claim 1 , wherein

X 1 is N;

X 5 is CR 5 ;

X 6 is CR 6 ;

X 7 is CR 7 ;

X 8 is N;

X 9 is CR 9 ;

R 6 , R 7 , R 9 and R 5 , are independently selected from the group consisting of hydrogen, alkyl, haloalkyl, and halogen.

9. A compound according to claim 8 , that is

1-pyrimidin-2-yl-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid (6-trifluoromethyl-pyridin-3-yl)-amide.

10. A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (VII) according to claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

11. A method of treating pain in a mammal, comprising administering a therapeutically effective amount of a compound of formula (VII) according to claim 1 or a pharmaceutically acceptable salt thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 9, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030176/0968 →
Continuity (3)
Division 1088738300 · Jul 8, 2004
Provisional Application 6048654800 · Jul 11, 2003
Related Publication 20070010557A1 · Jan 11, 2007