Back to results
US 8,410,146 B2Granted
2-pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors
AssigneeSK Chemicals Co., Ltd.
InventorsJu Young Lee, Jae-Sun Kim, Jung-Hoon Oh, Hoe-chul Jung, Hyun Jung Lee, Sang-hwan Kang, Yong-Hyuk Kim, Sung-hoon Park, Keun-Ho Ryu, Jung Bum Yi, Hun-Taek Kim, Key-An Um, Bong-yong Lee
Life of this patent
Estimating the term…
Abstract
2-pyridyl substituted imidazoles of the formula (I) as shown in claim 1, are provided, which are useful in the treatment of diseases mediated by ALK5 or ALK4 inhibitors or both.
Claims4
A compound of formula (I):
- wherein R1 is naphthyl, anthracenyl, or phenyl optionally substituted with substituents selected from halo, OH, —O—C1-6alkyl, —S—C1-6alkyl, C1-6alkyl, C1-6haloalkyl, —O— (CH2)n-Ph, —S— (CH2)n-Ph, cyano, phenyl, and CO2R, wherein R is H or C1-6alkyl, and n is 0, 1, 2, or 3;
- or R1 is phenyl or pyridyl fused with an aromatic or non-aromatic cyclic ring of 5-7 members wherein said cyclic ring optionally contains up to three heteroatoms, independently selected from N, O and S, and the fused phenyl or pyridyl may be further optionally substituted by halo, OH, —O—C1-6alkyl, —S—C1-6alkyl, C1-6alkyl, C1-6haloalkyl, cyano, phenyl or ═O;
- R2 is H, OH, —O—C1-6alkyl, —S—C1-6alkyl, C1-6alkyl, phenyl, C1-6haloalkyl, NH2, NH(CH2)n-Ph, NH—C1-6alkyl, halo, CN, NO2, CONHR or SO2NHR, wherein R is H or C1-6alkyl, and n is 0, 1, 2, or 3;
- R3 is or R3 is a heteroaromatic cyclic ring optionally substituted
- with substituents selected from halo, OH, —O—C1-6alkyl, —S—C1-6alkyl, C1-6alkyl, C1-6haloalkyl, amino, C1-6alkylamino, di(C1-6alkyl)amino, —O— (CH2)n-Ph, —S— (CH2)n-Ph, cyano, phenyl, and CO2R, wherein R is H or C1-6alkyl, and n is 0, 1, 2, or 3;
- or R3 is phenyl fused with an aromatic or non-aromatic cyclic ring of 5-7 members wherein said cyclic ring optionally contains up to three heteroatoms, independently selected from N, O and S, and the fused phenyl may be further optionally substituted by halo, OH, —O—C1-6alkyl, —S—C1-6alkyl, C1-6alkyl, C1-6haloalkyl, cyano, or phenyl;
- R4 is halo, C1-6haloalkyl, or —SO2C1-6alkyl;
- R5 and R6 are independently H, halo, C1-6alkyl, C3-7cycloalkyl, —(CH2)p—NO2, —(CH2)p—NR7R8, —(CH2)p—CHO, —(CH2)p—CONHOH, —(CH2)p—CN, —(CH2)p—CO2H, (CH2)p—CO2R7, —CH2)p—CONR7R8, —(CH2)p—C(═NR7)NR7R8, —(CH2)p-tetrazole, —(CH2)p—COR7, —(CH2)q—(OR9)2, —(CH2)p—OR7, —(CH2)p—CH═CH—CN, —(CH2)p—CH═CH—CO2H, —(CH2)p—CH═CH—CO2R7, —(CH2)p—CH═CH—CONR7R8, —(CH2)p—NHCOR7, —(CH2)p—NHCO2R7, —(CH2)p—CONHSO2R7, —(CH2)p—NHSO2R7 or —(CH2)p—CH═CH-tetrazole;
- R7 and R8 are independently H, phenyl or C1-6alkyl wherein phenyl or C1-6alkyl is optionally substituted by —(CH2)q—CONHOH, —(CH2)q—CN, —CH2)q—CO2R10, —(CH2)q—CONR11R12, —(CH2)q-tetrazole, —(CH2)r—OR10, —(CH2)r—R13, —(CH2)r—NR11R12;
- or R7 and R8 are taken together to form a non-aromatic cyclic ring of 3-6 members wherein said cyclic ring optionally contains up to three heteroatoms, independently selected from N, O and S;
- R9 is H or C1-6alkyl;
- R10, R11 and R12 are independently H or C1-6alkyl;
- R13 is H or a 3-7 membered heterocyclic ring optionally substituted at one, two or three positions by halo, OH, —O—C1-6alkyl, —S—C1-6alkyl, C1-6alkyl, C1-6haloalkyl, amino, C1-6alkylamino, di(C1-6alkyl)amino, cyano, oxo, carboxy or nitro;
- p is 0, 1, 2, 3, or 4;
- q is 1, 2, 3, or 4;
- r is 2, 3, or 4;
- X is C1-10alkylene, C2-10alkenylene or C2-10alkynylene;
- one of A1 and A2 is N and the other is NR14;
- and
- R14 is H, OH, C1-6alkyl, or C3-7cycloalkyl;
- or a pharmaceutically acceptable salt thereof.
18 more elements
Dependencies are inferred from the claim text.