Back to results
US 2017/0247371 A1Published application
One class of pyrazolone compounds and use thereof
AssigneeShanghai Institute of Materia Medica, Chinese Academy of Sciences
InventorsFajun NAN, Jia LI, Jingya LI, Mei ZHANG, Dakai CHEN, Lina ZHANG, Runtao ZHANG, Zhifu XIE
Life of this patent
Estimating the term…
Abstract
Provided are a class of pyrazolone compounds and a use thereof. In particular, a compound represented by formula I is provided, wherein the definition of each variable group is as described in the description. The compounds of formula (I) have a direct AMPK-activating activity and can significantly promote the phosphorylation of AMPK and ACC of L6 myocytes and HepG2 cells in a dose-dependent manner.
Claims15
A compound of formula I, or a pharmaceutically acceptable salt thereof:
- wherein R1 is selected from the group consisting of:
- H, C1-C4 alkyl, 6- to 12-membered aryl group or 5-10 membered heteroaryl in which hydrogen atoms on the group are optionally substituted with one or more substituents selected from the group consisting of:
- halogen, C1-C4 alkyl, C1-C4 halogen substituted alkyl, adamantyl, hydroxyl, amino, nitro, substituted or unsubstituted acetoxy group (AcO), carboxyl, C1-C4 alkoxy, C1-C4 haloalkoxy, cyano, substituted or unsubstituted phenyl, and —SO2—NH2;
- wherein the term “substituted” refers to one or more hydrogen atoms on a group are substituted with substituents selected from the group consisting of:
- halogen, trifluoromethyl, hydroxy, amino, C1-C4 alkyl, C1-C4 alkoxy, adamantyl, and cyano;
- R2 is selected from the group consisting of:
- H and C1-C4 alkyl, or R2 is none;
- R3 is selected from the group consisting of:
- H and C1-C4 alkyl, or R3 is none;
- R4 is selected from the group consisting of:
- H, C1-C4 alkyl, C1-C4 haloalkyl, halogen, hydroxy, amino, nitro, AcO, carboxyl, C1-C4 alkoxy, and cyano;
- R5 is selected from the group consisting of:
- H, C1-C4 alkyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, phenyl, C1-C4 alkylene phenyl, wherein hydrogen atoms on phenyl or C1-C4 alkylene phenyl are optionally substituted by one or more substituents selected from the group consisting of:
- hydroxy, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C7 cycloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy;
- wherein when R5 is a phenyl-containing group, the hydrogen atoms of two adjacent carbons on the phenyl are optionally substituted by “—O—(CH2)nO—”, wherein n=1, 2 or 3;
- n1 is 0, 1, or 2;
- n2 is 0, 1, 2, or 3;
- n3 is 0, 1, or 2;
- X is selected from the group consisting of:
- O and NR8, wherein R8 is selected from the group consisting of:
- H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C7 cycloalkyl, phenyl, and C1-C4 alkylene phenyl;
- and
- a dashed line is a chemical bond or none.
20 more elements
A compound of formula Ia:
- wherein
- R3 is selected from the group consisting of:
- H and C1-C4 alkyl, or R3 is none;
- R4 is selected from the group consisting of:
- H, C1-C4 alkyl, C1-C4 haloalkyl, halogen, hydroxy, amino, nitro, AcO, carboxyl, C1-C4 alkoxy, and cyano;
- R5 is selected from the group consisting of:
- H, C1-C4 alkyl, C3-C7 cycloalkyl, C1-C4 alkylene-C3-C7 cycloalkyl, phenyl, C1-C4 alkylene phenyl, wherein hydrogen atoms on phenyl or C1-C4 alkylene phenyl are optionally substituted by one or more substituents selected from the group consisting of:
- hydroxy, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C3-C7 cycloalkyl, C1-C4 alkoxy, and C1-C4 haloalkoxy;
- wherein when R5 is a phenyl-containing group, the hydrogen atoms of two adjacent carbons on the phenyl are optionally substituted by “—O—(CH2)nO—”, wherein n=1, 2 or 3;
- n1 is 0, 1, or 2;
- n2 is 0, 1, 2, or 3;
- n3 is 0, 1, or 2;
- X is selected from the group consisting of:
- O and NR8.
11 more elements
(canceled)
Dependencies are inferred from the claim text.