Liver X receptor modulators

Inventors: Chengguo Dong (Staten Island, NY); Yi Fan (Doylestown, PA); Katerina Leftheris (San Diego, CA); Stephen D. Lotesta (Burlington, NJ); Suresh B. Singh (Kendall Park, NJ); Colin M. Tice (Ambler, PA); Wei Zhao (Eagleville, PA); Yajun Zheng (Hockessin, DE); Linghang Zhuang (Chalfont, PA)

Assignee: Vitae Pharmaceuticals, Inc.

C07D487/04 A61K31/4985

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Quick Facts

Patent No.: US 9,006,244
App. No.: 14/385,688
Granted: Apr 14, 2015
Kind: B2

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Abstract

Provided herein are novel compounds and pharmaceutically acceptable salts thereof that are liver X receptor modulators. Also provided are compositions comprising compounds of the invention and a carrier. Additionally, use of the compounds herein and methods for treating a disease or disorder associated with the liver X receptor are further described.

Claims (71)

1. A compound represented by the following structural formula:

or a pharmaceutically acceptable salt thereof, wherein:

X is N or CR c ;

R 1 is alkyl or —NR a R b ;

R 2 is H; halogen; —CN; —NRC(O)R; —C(O)OR; —C(O)NR a R b ; monocyclic heteroaromatic optionally substituted with one or more groups selected from alkyl, —CN, —NRC(O)R, —C(O)OR, —C(O)NR a R b and halogen; monocyclic non-aromatic heterocycle optionally substituted with one or more groups selected from alkyl, halogen, —CN and ═O; or alkyl optionally substituted by one or more groups selected from halogen, hydroxy, alkoxy, —NR a R b , —NRC(O)R, —NRC(O)O(alkyl),

—NRC(O)N(R) 2 , —C(O)OR, thiol, alkylthiol, nitro, —CN, ═O, —OC(O)H,

—OC(O)(alkyl), —OC(O)O(alkyl), —OC(O)N(R) 2 and —C(O)NR a R b ;

R 3 is alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, monocyclic non-aromatic heterocycle, monocyclic heteroaromatic or phenyl, wherein the phenyl, monocyclic non-aromatic heterocycle, and monocyclic heteroaromatic group represented by R 3 are optionally substituted with one or more groups selected from alkyl, halogen, haloalkyl, alkoxy, haloalkoxy, nitro and —CN;

R 4 is halogen, —CN, —OR, —SR, —N(R) 2 , —C(O)R, —C(O)OR, —OC(O)O(alkyl), —C(O)O(haloalkyl), —OC(O)R, —C(O)N(R) 2 , —OC(O)N(R) 2 , —NRC(O)R, —NRC(O)O(alkyl), —S(O)R, —SO 2 R, —SO 2 N(R) 2 , —NRS(O)R, —NRSO 2 R, —NRC(O)N(R) 2 , —NRSO 2 N(R) 2 , haloalkyl, haloalkoxy, cycloalkoxy, cycloalkyl, monocyclic non-aromatic heterocycle, monocyclic heteroaromatic or alkyl, wherein the monocyclic non-aromatic heterocycle, monocyclic heteroaromatic and alkyl group represented by R 4 are optionally substituted with one or more groups selected from —CN, —OR, —SR, —N(R) 2 , ═O, —C(O)R, —C(O)OR, —C(O)O(haloalkyl), —OC(O)R, —OC(O)O(alkyl), —C(O)N(R) 2 , —OC(O)N(R) 2 , —NRC(O)R, —NRC(O)O(alkyl), —S(O)R, —SO 2 R, —SO 2 N(R) 2 , —NRS(O)R, —NRSO 2 R, —NRC(O)N(R) 2 and —NRSO 2 N(R) 2 ;

Each R independently is H or alkyl;

R a and R b are independently H, alkyl or R a and R b can be taken together with the nitrogen to which they are attached to form a monocyclic non-aromatic heterocycle; and

R c is H, alkyl, or halogen.

2. The compound of claim 1 , wherein:

R 3 is alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl or phenyl, wherein the phenyl represented by R 3 is optionally substituted with one or more groups selected from alkyl, halogen, haloalkyl, alkoxy, haloalkoxy, nitro and —CN;

R 4 is halogen, —CN, —OR, —SR, —N(R) 2 , —C(O)R, —C(O)OR, —OC(O)O(alkyl), —C(O)O(haloalkyl), —OC(O)R, —C(O)N(R) 2 , —OC(O)N(R) 2 , —NRC(O)R, —NRC(O)O(alkyl), —S(O)R, —SO 2 R, —SO 2 N(R) 2 , —NRS(O)R, —NRSO 2 R, —NRC(O)N(R) 2 , —NRSO 2 N(R) 2 , haloalkyl, haloalkoxy, cycloalkoxy, cycloalkyl or alkyl, wherein the alkyl group represented by R 4 is optionally substituted with one or more groups selected from —CN, —OR, —SR, —N(R) 2 , ═O, —C(O)R, —C(O)OR, —C(O)O(haloalkyl), —OC(O)R, —OC(O)O(alkyl), —C(O)N(R) 2 , —OC(O)N(R) 2 , —NRC(O)R, —NRC(O)O(alkyl), —S(O)R, —SO 2 R, —SO 2 N(R) 2 , —NRS(O)R, —NRSO 2 R, —NRC(O)N(R) 2 and —NRSO 2 N(R) 2 .

3. The compound of claim 1 , wherein the compound is represented by the following structural formula: