Liver X receptor modulators

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 alkyl, monocyclic non-aromatic heterocycle and monocyclic heteroaromatic 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 ;

R 5 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 and monocyclic heteroaromatic group represented by R 5 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 , and wherein the alkyl represented by R 5 is 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 ;

R 6 is H, 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 6 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 ; or

R 5 and R 6 , taken together with the carbon atoms to which they are bonded, form a moncyclic non-aromatic heterocycle optionally substituted with one or more groups selected from alkyl, halogen, hydroxyalkyl, alkoxyalkyl, haloalkyl and ═O; and

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 group 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 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 ;

R 5 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 represented by R 5 is 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 ;

R 6 is H, 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 6 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 2 , wherein the compound is represented by the following structural formula:

or a pharmaceutically acceptable salt thereof.

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

or a pharmaceutically acceptable salt thereof.

5. The compound of claim 4 , wherein the compound is represented by the following structural formula:

or a pharmaceutically acceptable salt thereof.

6. The compound of claim 5 , wherein the compound is represented by the following structural formula:

or a pharmaceutically acceptable salt thereof.

7. The compound of claim 4 , wherein the compound is represented by the following structural formula:

or a pharmaceutically acceptable salt thereof.

8. The compound of claim 7 , wherein the compound is represented by the following structural formula:

or a pharmaceutically acceptable salt thereof.

9. The compound of claim 8 , wherein:

R 1 is methyl or —NH 2 ;

R 2 is H or methyl, wherein the methyl group represented by R 2 is optionally substituted with 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), —C(O)NR a R b and —OC(O)N(R) 2 ;

R 3 is methyl, ethyl, propyl, isopropyl, tert-butyl, sec-butyl, iso-butyl, —CH 2 CF 3 , —CH(CH 2 F) 2 , —CH(CHF 2 ) 2 , —CH(CF 3 ) 2 , —CF(CH 3 ) 2 , —CF 3 , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, —C(OH)(CH 3 ) 2 , —CH(OH)(CH 3 ), or phenyl, wherein the phenyl group represented by R 3 is optionally substituted with one or more groups selected from alkyl, halogen, haloalkyl, alkoxy, haloalkoxy, nitro and —CN; and

R c , where present, is H.

10. The compound of claim 9 , wherein R 2 is H or —CH 2 OH.

11. The compound of claim 10 , wherein:

R 1 is methyl;

R 2 is —CH 2 OH; and

R 3 is isopropyl.

12. The compound of claim 11 , wherein R 4 is halogen, hydroxy, alkyl, cycloalkyl, cycloalkoxy, alkoxy, haloalkoxy, haloalkyl, —N(R) 2 , —C(O)OH, —C(O)O(alkyl), —C(O)O(haloalkyl), —C(O)(alkyl), —C(O)N(R) 2 , —NRC(O)R, —SO 2 N(R) 2 , —OC(O)N(R) 2 , —CN, hydroxyalkyl or dihydroxyalkyl; and R 5 is halogen, hydroxy, cycloalkyl, cycloalkoxy, alkoxy, haloalkoxy, haloalkyl, —N(R) 2 , —C(O)OH, —C(O)O(alkyl), —C(O)O(haloalkyl), —C(O)(alkyl), —C(O)N(R) 2 , —NRC(O)R, —SO 2 N(R) 2 , —OC(O)N(R) 2 , —CN, hydroxyalkyl or dihydroxyalkyl.

13. The compound of claim 12 , wherein R 4 is methyl, ethyl, hydroxy, CF 3 , isopropyl, cyclopropyl, —CH 2 OH, —CH(OH)(CH 2 )(OH), —C(OH)(CH 3 ) 2 , —CH(OH)(CH 3 ), —CH(OH)(CH 2 )(CH 3 ), —CH(OH)(CH 2 ) 2 (CH 3 ), —C(O)NH 2 , —C(O)N(CH 3 ) 2 , —C(O)OH, —C(O)NH(CH 3 ), —C(O)CH 3 , —C(O)CH 2 CH 3 , —C(O)O(CH 2 )(CH 3 ), —C(O)O(tert-butyl), —C(O)O(C)(CH 3 ) 2 (CF 3 ), —NHC(O)CH 3 , —OCHF 2 , —OCF 3 , —OCH 2 CH 3 , —OCH(CH 3 ) 2 or —OCH 3 ; and R 5 is hydroxy, CF 3 , cyclopropyl, —CH 2 OH, —CH(OH)(CH 2 )(OH), —C(OH)(CH 3 ) 2 , —CH(OH)(CH 3 ), —CH(OH)(CH 2 )(CH 3 ), —CH(OH)(CH 2 ) 2 (CH 3 ), —C(O)NH 2 , —C(O)N(CH 3 ) 2 , —C(O)OH, —C(O)NH(CH 3 ), —C(O)CH 3 , —C(O)CH 2 CH 3 , —C(O)O(CH 2 )(CH 3 ), —C(O)O(tert-butyl), —C(O)O(C)(CH 3 ) 2 (CF 3 ), —NHC(O)CH 3 , —OCHF 2 , —OCF 3 , —OCH 2 CH 3 , —OCH(CH 3 ) 2 or —OCH 3 .

14. The compound of claim 13 , wherein R 4 is alkyl, haloalkyl, cycloalkyl, alkoxy, or haloalkoxy.

15. The compound of claim 14 , wherein R 4 is methyl, halogenated methyl, cyclopropyl, —OCHF 2 or —OCH 3 .

16. The compound of claim 15 , wherein R 4 is CF 3 .

17. The compound of claim 16 , where R 5 —C(OH)(CH 3 ) 2 .

18. The compound of claim 1 , wherein the compound is represented by a structural formula selected from

or a pharmaceutically acceptable salt thereof.

19. A pharmaceutical composition comprising a pharmaceutical carrier or diluent and the compound of claim 1 .

20. A compound represented by the following structural formula:

or a salt thereof, wherein:

X is N or CR c ;

R 10 is alkyl or —NR a R b ;

R 20 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 , —C(O)NR a R b , and —O (protecting group);

R 30 is alkyl, haloalkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl or phenyl, wherein the phenyl group represented by R 30 is optionally substituted with one or more groups selected from alkyl, haloalkyl, alkoxy, haloalkoxy, nitro and —CN;

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.

21. The compound of claim 20 , wherein the compound is represented by the following structural formula:

or a salt thereof.

22. The compound of claim 21 , wherein the compound is represented by the following structural formula:

or a salt thereof.

23. The compound of claim 21 , wherein the compound is represented by the following structural formula:

or a salt thereof.

24. The compound of claim 23 , wherein R 10 is —CH 3 .

25. The compound of claim 24 , wherein R 20 is —CH 2 OH, —CH 2 O (protecting group), —COOH, or —C(O)O(alkyl).

26. The compound of claim 25 , wherein R 30 is isopropyl.

27. The compound of claim 26 , wherein R 20 is —CH 2 O(TBDPS) or —C(O)OCH 3 .