Back to results
US 2014/0179738 A1Published application
N-Substituted-Heterocycloalkyloxybenzamide Compounds and Methods of Use
AssigneeRigel Pharmaceuticals, Inc.
InventorsRajinder Singh, Jiaxin Yu, Hui Hong, Sambaiah Thota, Xiang Xu, Ihab S. Darwish
Life of this patent
Estimating the term…
Abstract
The present invention provides N-substituted-heterocycloalkyloxybenzamide compounds, as well as pharmaceutical compositions and methods of use. One embodiment of the invention is a compound having the structure in which R1, R2, R3, R4, T, n, w and x are as described herein. In certain embodiments of the invention, a compound of the present invention activates the AMPK pathway, and can be used to treat metabolism-related disorders and conditions.
Claims25
1-69. (canceled)
A compound having the structural formula
- or a pharmaceutically acceptable salt or N-oxide thereof, wherein
- each R3 is independently selected from halo, cyano, —(C1-C4 fluoroalkyl), —O—(C1-C4 fluoroalkyl), acyl, carboxylate, carboxamide and nitro;
- w is 0, 1, 2 or 3;
- each R4 is independently selected from —(C1-C6 alkyl), —(C1-C6 fluoroalkyl), -halogen, —NO2 and —CN, and two R4 on the same carbon optionally combine to form oxo;
- x is 0, 1, 2, 3 or 4;
- each R5 is independently selected from —(C1-C6 alkyl), —(C1-C6 fluoroalkyl), —(C0-C6 alkyl)-L-R7, —(C0-C6 alkyl)-NR8R9, —(C0-C6 alkyl)-OR10, —(C0-C6 alkyl)-S(O)0-2R10, -halogen, —NO2 and —CN;
- y is 0, 1, 2, 3 or 4;
- G is a single bond, —CH2— or —C(O)—;
- v is 0, 1, 2, 3 or 4;
- each R15 is independently selected from —(C1-C6 alkyl), —(C1-C6 fluoroalkyl), -halogen, —NO2 and —CN, and two R15 on the same carbon optionally combine to form oxo;
- and
- R17 is optionally-substituted aryl;
- in which
- each L is independently selected
- from —NR9C(O)O—, —NR9C(O)—NR9—, —NR9C(O)S—, —NR9C(O)—, —NR9C(S)O—, —NR9C(S)—NR9—, —NR9C(S)S—, —NR9C(S)—, —OC(O)NR9—, —SC(O)NR9—, —C(S)NR9—, —OC(S)NR9—, —SC(S)NR9—, —C(S)NR9—, —S(O)0-2—, —C(O)O, —OC(O)—, —C(S)O—, —OC(S)—, —C(O)S—, —SC(O)—, —C(S)S—, —SC(S)—, —OC(O)O—, —SC(O)O—, —OC(O)S—, —SC(S)O—, —OC(S)S—, —NR9C(NR9)NR9—, —NR9SO2—, —SO2NR9— and —NR9SO2NR9—,
- each R7, R8 and R1° is independently selected from H, —(C1-C6 alkyl), —(C1-C6 fluoroalkyl), —(C0-C6 alkyl)-L-(C0-C6 alkyl), —(C0-C6 alkyl)-NR9(C0-C6 alkyl), —(C0-C6 alkyl)-O—(C0-C6 alkyl) and —(C0-C6 alkyl)-S(O)0-2—(C0-C6 alkyl),
- each R9 is independently selected from —H, —(C1-C4 alkyl) and —C(O)—(C1-C4 alkyl), and
- each R16 is independently selected from —(C1-C6 alkyl), —(C1-C6 fluoroalkyl), and two R16 on the same carbon optionally combine to form oxo;
- provided that the compound is not
- N-(1-benzylpiperidin-4-yl)-3-chloro-4-(1-(4-methoxybenzyl)piperidin-4-yloxy)benzamide;
- N-(1-benzylpiperidin-4-yl)-4-(1-benzylpiperidin-4-yloxy)-3-methoxybenzamide;
- or
- N-(1-benzylpiperidin-4-yl)-3-(1-benzylpiperidin-4-yloxy)benzamide.
20 more elements
Dependencies are inferred from the claim text.