IP Library › Granted Patent US 8,501,794

Granted Patent B2

US 8,501,794 · App. 12/612,504 · Granted Aug 6, 2013

Compounds as cannabinoid receptor ligands

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 8,501,794
App. No.: 12/612,504
Granted: Aug 6, 2013
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

The present application relates to isothiazolylidene containing compounds of Formula (I) wherein R 1 , R 2 , R 3 , R 4 , and L are as defined in the specification, compositions comprising such compounds, and methods for treating conditions and disorders using such compounds and compositions.

Claims (127)

1. A compound selected from the group consisting of:

neopentyl (5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidenecarbamate;

2,2,2-trichloroethyl (5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidenecarbamate;

1-adamantyl (5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidenecarbamate;

N 2 -({[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]amino}carbonyl)-N 1 -3-dimethyl-L-valinamide; and

N-[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N′-(4-methylcyclohexyl)urea;

or a pharmaceutically acceptable salt thereof.

2. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

3. A method for treating pain in a mammal in need of such treatment comprising administering to the mammal a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

4. A method for treating an inflammatory disorder in a mammal in need of such treatment, comprising administering to the mammal a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof.

5. A compound selected from the group consisting of:

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -(2-hydroxyethyl)- 1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1 S,3R)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 1 -(2-hydroxyethyl)- 1,2,2-trimethylcyclopentane- 1,3 -dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -(3-hydroxyp ropyl)- 1,2,2-trimethylcyclopentane- 1,3 -dicarboxamide;

(1 S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -(2-methoxyethyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;, (1 S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -(3-hydroxypropyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide; (1 S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -(2-hydroxyethyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide; (1R,3S)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 1 -(2-hydroxyethyl)-1,2,2-trimethylcyclopentane- 1,3-dicarboxamide ;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol- 5 (2H)-ylidene]- 1,2,2- trimethyl-N 3 -prop-2-ynylcyclopentane- 1,3 -dicarboxamide:

(1 S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol- 5 (2H)-ylidene]- 1,2,2-trimethyl-N 3 -prop-2-ynylcyclopentane-1,3-dicarboxamide: and (1 R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -methoxy-N 3 ,1,2,2-tetramethylcyclopentane- 1,3 -dicarboxamide ;

or a pharmaceutically acceptable salt thereof.

6. A compound selected from the group consisting of:

N-[(5Z)-2-tert-butyl-4-(1-hydroxyethyl)isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide;

N-[(5Z)-2-tert-butyl-4-(1 -ethoxyethyl)isothiazol-5 (2H)-ylidene]-5-chloro-2-methoxybenzamide;

N-[(5Z)-2-tert-butyl-4-(1 -methoxyethyl)isothiazol-5 (2H)-ylidene]-5-chloro-2-methoxybenzamide;

N-[(5Z)-2-tert-butyl-4-[1 -(2,2,2-trifluoro ethoxy)ethyl]isothiazol-5 (2H)-ylidene]-5-chloro-2-methoxybenzamide;

N-[(5 Z)-2-tert-butyl-4-vinylisothiazol-5 (2H)-ylidene]-5-chloro-2-methoxybenzamide;

(1R,3S)-3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-3-hydroxy -1,2,2-trimethylcyclopentanecarboxylic acid;

(1 S,3R)-3- ({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-3-hydroxy-1,2,2-trimethylcyclopentanecarboxylic acid;

methyl (1R,3S)-3-({[(5Z)-4-butyl-2-tert-butylis othiazol-5 (2H)-ylidene]amino}carbonyl)-1,2,2-trimethylcyclopentanecarboxylate;

(1 R,3S)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethylcyclopentane -1,3-dicarboxamide;

(1 S,3R)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethyl-3-(pyrrolidin-1-ylcarbonyl)cyclopentanecarboxamide;

(1 S,3R)-3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid;

(1R,3S)-3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclopentanecarboxylic acid;

ethyl (1 S,3R)-3-({[(5Z)-4-butyl 1-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclopentanecarboxylate;

ethyl (1R,3S)-3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]amino}carbonyl) -2,2,3-trimethylcyclopentanecarboxylate;

methyl (1 S,3R)-3-({[(5Z)-4-butyl-2-tert-butylis othiazol-5 (2H)-ylidene]amino}carbonyl) -2,2,3-trimethylcyclopentanecarboxylate;

(1R,3S)-3-(azetidin-1 -ylcarbonyl)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethylcyclopentanecarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 ,N 3 ,1,2,2-pentamethylcyclopentane-1,3-dicarboxamide;

(1 R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-3-[(3-hydroxyazetidin-1 -yl) carbonyl]-1,2,2-trimethylcyclopentanecarboxamide;

(1R,3S)-3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-1,2,2-trimethylcyclopentanecarboxylic acid;

(1R,3S)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 1 ,1,2,2-tetramethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 3 -[(5Z) -4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 1 ,N 1 ,1,2,2-pentamethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]tetramethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-3-[(3,3-difluoroazetidin-1 -yl)carbonyl]-1,2,2-trimethylcyclopentanecarboxamide;

methyl (1R,3S)-3-({[(5Z)-4-butyl-2-tert-butylis othiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclopentanecarboxylate;

neopentyl (5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidenecarbamate;

2,2,2-trichloroethyl(5 Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidenecarbamate;

1 -adamantyl(5 Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidenecarbamate;

N 2 -({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H) -ylidene]amino}carbonyl)-N 1 -3-dimethyl-L -valinamide;

N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene](4-methylcyclohexyl)urea;

N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-2-{[(2S)-1 -methylpyrrolidin-2-yl]methoxy}-5-(trifluoromethyl)benzamide;

N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N′-cyano-2-{[(2S)-1-methylpyrrolidin -2-yl]methoxy}-5-(trifluoromethyl)benzenecarboximidamide;

N-[(5 Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-2-{[(2S)-5-oxopyrrolidin-2-yl]methoxy}-5-(trifluoromethyl)benzamide;

N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-2-{[(4R)-2-oxo-1,3-oxazolidin-4-yl]methoxy}-5- (trifluoromethyl)benzamide;

N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-2-[(1-methylpiperidin-2-yl)methoxy]-5-(trifluoromethyl)benzamide;

N-[(5 Z)-2-tert-butyl-4-isobutylisothiazol-5 (2H)-ylidene]-2-{[(2S) -1 -methylpyrrolidin-2-yl]methoxy}-5-(trifluoromethyl)benzamide;

N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-2-(pyrazin-2-ylmethoxy) -5-(trifluoromethyl)benzamide;

N-[(5Z)-2-tert-butyl-4-isobutylisothiazol-5 (2H)-ylidene]-2- (pyrazin-2-ylmethoxy)-5-(trifluoromethyl)benzamide;

N-[(5Z)-2-tert-butyl-4-isobutylisothiazol-5 (2H)-ylidene]-2- (pyridin-2-ylmethoxy)-5-(trifluoromethyl)benzamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -ethyl-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H) -ylidene]-1,2,2-trimethyl-N 3 -propylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -(2-hydroxyethyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

methyl (1 S,3R)-3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-1,2,2-trimethylcyclopentanecarboxylate;

(1 S,3R)-3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-1,2,2-trimethylcyclopentanecarboxylic acid;

(1R,3S)-N 1 -[(5Z) -4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -isopropyl-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -cyclobutyl-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -cyclopropyl-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1 S,3R)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 1 ,1,2,2-tetramethylcyclop entane-1,3-dicarboxamide;

(1 S,3R)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 1 -ethyl-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1 S,3R)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethyl-N 1 -propylcyclopentane-1,3-dicarboxamide;

(1 S,3R)-N 3 -[(5Z) -4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 1 -(2-hydroxyethyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z) -4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-N 3 -(3-hydroxypropyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide; and

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -[(2R)- tetrahydrofuran-2-ylmethyl]cyclopentane-1,3-dicarboxamide;

or a pharmaceutically acceptable salt thereof.

7. A compound selected from the group consisting of:

methyl (1 S,3R)-3-({[(5Z) -4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclopentylcarbamate;

ethyl (1 S,3R) -3-({[(5Z) -4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclopentylcarbamate;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-3-(4,5-dihydro-1,3-oxazol-2-y1)-1,2,2-trimethylcyclopentanecarboxamide;

(1S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N 3 -1,2,2- tetramethylcyclopentane-1,3-dicarboxamide;

(1S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -propylcyclopentane-1,3-dicarboxamide;

(1S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N 3 -(2-methoxyethyl)-1, 2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N 3 -(3-hydroxypropyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1S,3R)-3-(azetidin-1-ylcarbonyl)-N-[(5Z)-4-bu 1-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethylcyclopentanecarboxamide;

(1S,3R)-N 1 -[(5Z)-4-bu 1-2-tert-butylisothiazol-5(2H)-ylidene]-N 3 , N 3 ,1,2,2-pentamethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-3-(4,5-dihydro-1,3-oxazol-2-y1)-2,2,3-trimethylcyclopentanecarboxamide;

(1S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N 3 -cyclobutyl-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -[(2S) -tetrahydrofuran-2-yl-methyl]cyclopentane-1,3-dicarboxamide;

(1S,3R)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 1 -[(2S) -tetrahydrofuran-2-ylmethyl]cyclopentane-1,3-dicarboxamide;

(1S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N 3 -(2-hydroxyethyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N 1 -ethyl-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 3 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N 1 -(2-hydroxyethyl)-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1S,3R)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-3-(4,5-dihydro-1,3-oxazol-2-y1)-1,2,2-trimethylcyclopentanecarboxamide;

(1S,3R)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-3-(4,5-dihydro-1,3-oxazol-2-y1)-2,2,3-trimethylcyclopentanecarboxamide;

(1R,3S)-N 3 -benzyl-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -(pyridin-2-ylmethyl)cyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -(pyridin-3-ylmethyl)cyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -(pyridin-4-ylmethyl)cyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -prop-2-ynylcyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -(2,2,2-trifluoroethyl)cyclopentane-1,3-dicarboxamide;

(1S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -prop-2-ynylcyclopentane-1,3-dicarboxamide;

(1S,3R)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-1,2,2-trimethyl-N 3 -(2,2,2-trifluoroethyl)cyclopentane-1,3-dicarboxamide;

(1R,3S)-N 1 -[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-N 3 -methoxy-N 3 ,1,2,2-tetramethylcyclopentane-1,3-dicarboxamide;

(1 S,3R)-N-[(5Z)-4-bu 1-2-tert-butylisothiazol-5(2H)-ylidene]-3-(5,6-dihydro-4H-1,3-oxazin -2-yl)-1,2,2-trimethylcyclopentanecarboxamide;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]-3-(5,6-dihydro-4H-1,3-oxazin -2-yl)-1,2,2-trimethylcyclopentanecarboxamide;

N-[(1 S,3R) -3- ({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl) -2,2,3-trimethylcyclopentyl]pyrrolidine-1-carboxamide;

(1 R,3S)-3-[(aminocarbonyl) amino]-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H) -ylidene]-1,2,2-trimethylcyclopentanecarboxamide;

(1 R,3S)-3-[(aminocarbonyl) amino]-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H) -ylidene]-2,2,3-trimethylcyclopentanecarboxamide;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-2,2,3-trimethyl-3-{[(methylamino) carbonyl]amino }cyclopentanecarboxamide;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethyl-3-(morpholin -4-ylcarbonyl)cyclopentanecarboxamide;

(1 R,3S)-N 1 -[(5Z) -4-bu 1-2-tert-butylisothiazol-5 (2H) -ylidene]-1,2,2-trimethyl-N 3 -pyrrolidin -1 -ylcyclopentane-1,3-dicarboxamide;

N-[(1 S,3R) -3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl) -2,2,3-trimethylcyclop entyl]morpholine-4-carboxamide;

N-[(1 S,3R) -3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl) -2,2,3-trimethylcyclopentyl]benzamide;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethyl-3-{[(methylamino)carbonyl]amino }cyclopentanecarboxamide;

(1 S,3R)-3-[(aminocarbonyl) amino]-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethylcyclopentanecarboxamide;

(1 S,3R)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethyl-3-{[(methylamino) carbonyl]amino }cyclopentanecarboxamide;

N-[(1R,3S) -3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclop entyl]benzamide;

(1R,3S)-3-(acetylamino)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethylcyclopentanecarboxamide;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-3-({[(2-hydroxyethyl)amino]carbonyl}amino) -1,2,2-trimethylcyclopentanecarboxamide;

(1 R,3S)-N- [(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-3-[({[(2S) -2-hydroxyp ropyl]amino}carbonyl) amino]-1,2,2-trimethylcyclopentanecarboxamide;

(1 R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-3-[({[(2R)-2-hydroxyp ropyl]amino}carbonyl) amino]-1,2,2-trimethylcyclopentanecarboxamide;

N-[(1 S,3R) -3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclopentyl]-3-hydroxyazetidine-1 -carboxamide;

N-[(1 S,3R) -3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl) -2,2,3-trimethylcyclopentyl]-3,3-difluoroazetidine-1 -carboxamide;

N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-2-(2-hydroxy-2-methylpropoxy)-5-(trifluoromethyl)benzamide;

N-[(1 S,3R)-3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)-2,2,3-trimethylcyclopentyl]azetidine-1 -carboxamide;

(1R,3S)-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-1,2,2-trimethyl-3-({[methyl(phenyl)amino]carbonyl}amino)cyclopentanecarboxamide;

methyl 3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]amino}carbonyl)adamantane-1-carboxylate;

3-({[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H) -ylidene]amino}carbonyl) adamantane-1 -carboxylic acid; and

2-[(tert-butylamino)oxy]-N-[(5Z)-4-butyl-2-tert-butylisothiazol-5 (2H)-ylidene]-5-(trifluoromethyl)benzamide;

or a pharmaceutically acceptable salt thereof.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 17, 2013

From: ABBOTT LABORATORIES

To: ABBVIE INC.

Reel/Frame 030235/0856 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2010

From: CARROLL, WILLIAM A.; DART, MICHAEL J.; KOLASA, TEODOZYJ; LI, TONGMEI; NELSON, DEREK W.; PATEL, MEENA V.; PEDDI, SRIDHAR; PEREZ-MEDRANO, ARTURO; WANG, XUEQING

To: ABBOTT LABORATORIES

Reel/Frame 024470/0293 →