3-arylamino pyridine derivatives

1. A compound of formula (II),

or a pharmaceutically acceptable salt thereof,

wherein:

R 1 , R 2 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are independently selected from hydrogen, halogen, cyano, nitro, azido, —OR 3 , —NR 4 C(O)OR 6 , —OC(O)R 3 , —NR 4 S(O) j R 6 , —S(O) j NR 3 R 4 , —S(O) j NR 4 C(O)R 3 , —C(O)NR 4 S(O) j R 6 , S(O) j R 6 , —NR 4 C(O)R 3 , —C(O)NR 3 R 4 , —NR 5 C(O)NR 3 R 4 , —NR 5 C(NCN)NR 3 R 4 , —NR 3 R 4 , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl or —S(O) j (C 1 -C 6 alkyl);

provided that R 12 is not OH, and R 13 , R 14 are not C 1 -C 10 alkyl;

R 3 is selected from hydrogen, trifluoromethyl, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkylalkyl, where each alkyl, alkenyl, alkynyl and cycloalkyl is unsubstituted or substituted with primary amino, aminocarbonyl, carboxyl, cyano, halogen, hydroxy, nitro or trihalomethyl;

R 4 is selected from hydrogen or C 1 -C 6 alkyl, whereby alkyl may be unsubstituted or substituted with primary amino, aminocarbonyl, carboxyl, cyano, halogen, hydroxy, nitro or trihalomethyl;

R 5 is selected from hydrogen or C 1 -C 6 alkyl, whereby alkyl may be unsubstituted or substituted with primary amino, aminocarbonyl, carboxyl, cyano, halogen, hydroxy, nitro or trihalomethyl;

R 6 is selected from trifluoromethyl, C 1 -C 10 alkyl or C 3 -C 10 cycloalkyl;

W is selected from —C(O)OR 15 , —C(O)NR 4 R 15 , —C(O)NR 4 OR 15 , —C(O)NR 4 S(O) j R 6 , —C(O)NR 4 NR 4 R 15 , —NR′C(O)R′, —NR′S(O) j R′, —NRC(O)NR′R″, NR′S(O) j NR′R″ or —C(O)NR 4 NR 4 C(O)R 15 ;

provided that W is not C(O)OH;

R 15 is independently selected from hydrogen, trifluoromethyl, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl or heterocyclylalkyl, where each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl and heterocyclyl is unsubstituted or substituted with primary amino, aminocarbonyl, carboxyl, cyano, halogen, hydroxy, nitro, trihalomethyl, O—C 1 -C 4 alkyl or NR′R″;

R′ and R″ are independently selected from hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, aryl or arylalkyl;

X is N or N + O − ; and

j is 1 or 2, with the proviso that 3-Phenylamino-isonicotinic acid methyl ester and 3-Oxo-3-(3-phenylamino-pyridin-4-yl)-propionic acid ethyl ester are not included.

2. A compound of formula (II) according to claim 1 , wherein:

R 1 , R 2 , R 9 , R 10 , R 11 , R 12 , R 13 and R 14 are independently selected from hydrogen, halogen, cyano, nitro, azido, —OR 3 , —NR 4 C(O)OR 6 , —OC(O)R 3 , —NR 4 S(O) j R 6 , —S(O) j NR 3 R 4 , —S(O) j NR 4 C(O)R 3 , —C(O)NR 4 S(O) j R 6 , S(O) j R 6 , —NR 4 C(O)R 3 , —C(O)NR 3 R 4 , —NR 5 C(O)NR 3 R 4 , —NR 5 C(NCN)NR 3 R 4 , —NR 3 R 4 , C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl or —S(O) j (C 1 -C 6 alkyl);

provided that R 12 is not OH, and R 13 , R 14 are not C 1 -C 10 alkyl;

R 3 is selected from hydrogen, trifluoromethyl, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl or C 3 -C 10 cycloalkylalkyl, where each alkyl, alkenyl, alkynyl and cycloalkyl is unsubstituted or substituted with primary amino, aminocarbonyl, carboxyl, cyano, halogen, hydroxy, nitro or trihalomethyl;

R 4 is selected from hydrogen or C 1 -C 6 alkyl, whereby alkyl may be unsubstituted or substituted with primary amino, aminocarbonyl, carboxyl, cyano, halogen, hydroxy, nitro or trihalomethyl;

R 5 is selected from hydrogen or C 1 -C 6 alkyl, whereby alkyl may be unsubstituted or substituted with primary amino, aminocarbonyl, carboxyl, cyano, halogen, hydroxy, nitro or trihalomethyl;

R 6 is selected from trifluoromethyl, C 1 -C 10 alkyl or C 3 -C 10 cycloalkyl;

W is —C(O)OR 15 , —C(O)NR 4 R 15 , —C(O)NR 4 OR 15 or —C(O)NR 4 S(O) j R 6 ;

provided that W is not C(O)OH;

R 15 is independently selected from hydrogen, trifluoromethyl, C 1 -C 10 alkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl or heterocyclylalkyl, where each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl and heterocyclyl is unsubstituted or substituted with primary amino, aminocarbonyl, carboxyl, cyano, halogen, hydroxy, nitro, trihalomethyl, O—C 1 -C 4 alkyl or NR′R″;

R′ and R″ are independently selected from hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, aryl or arylalkyl;

X is N or N + O − ; and

j is 1 or 2.

3. The compound of Formula (II) according to claim 1 , wherein:

R 1 , R 2 , R 9 and R 11 are independently selected from hydrogen, halo, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, cyano, nitro, OR 3 or NR 3 R 4 , where each alkyl, alkenyl, alkynyl, cycloalkyl is optionally substituted with one to five halogens;

R 10 and R 12 are independently selected from hydrogen, halo, C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, cyano, nitro, azido, NR 4 SO 2 R 6 , SO 2 NR 3 R 4 , SO 2 R 6 , C(O)NR 3 R 4 , —S(O) j NR 4 C(O)R 3 , —C(O)NR 4 S(O) j R 6 , OR 3 , NR 3 R 4 or —S(C 1 -C 2 alkyl) substituted with 1 to 5 F;

R 13 and R 14 are independently selected from H, F, Cl, C 1 -C 4 alkyl, C 3 -C 4 cycloalkyl, C 2 -C 4 alkenyl or C 2 -C 4 alkynyl, where each alkyl, alkenyl, cycloalkyl, alkynyl is optionally substituted with one to five halogens;

W is —C(O)OR 15 , —C(O)NR 4 R 15 , —C(O)NR 4 OR 15 , —C(O)(C 2 -C 10 alkyl) or —C(O)NR 4 S(O) j R 6 ;

R 15 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkenyl or C 4 -C 6 cycloalkylalkyl, where alkyl or alkenyl is optionally substituted by 1 or 2 of OH, O—C 1 -C 4 alkyl or NR′R″; and

R′ and R″ are each independently selected from hydrogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, aryl or arylalkyl.

4. The compound of Formula (II) according to claim 1 , wherein:

R 1 is independently selected from H and F;

R 2 is independently selected from hydrogen, F, Cl or Me, where the methyl group is optionally substituted with one to three fluorines;

R 9 is independently selected from H, F or Cl;

R 10 is independently selected from H, F, Cl, Br, nitro, Me or OMe, where the methyl groups are optionally substituted with one to three fluorines, SO 2 NR 3 R 4 or C(O)NR 3 R 4 , wherein R 3 and R 4 are independently C 1 -C 6 alkyl, optionally substituted by 1 or 2 alkyl amino or O-alkyl, or R 3 and R 4 taken together form a cyclic ring with 1 or 2 N atoms and optionally an O atom, said ring being optionally substituted by 1 or 2 alkyl amino or O-alkyl;

R 11 is independently selected from H, F, Cl, Br, Me or OMe, where the methyl groups are optionally substituted with one to three fluorines;

R 12 is independently selected from H, F, Cl, Br, nitro, Me, SCF 3 , SCHF 2 , SCH 2 F, SO 2 NR 3 R 4 , C(O)NR 3 R 4 or OMe, where the methyl groups are optionally substituted with one to three fluorines, wherein R 3 and R 4 are independently C 1 -C 6 alkyl, optionally substituted by 1 or 2 alkyl amino or O-alkyl, or R 3 and R 4 taken together form a cyclic ring with 1 or 2 N atoms and optionally an O atom, said ring being optionally substituted by 1 or 2 alkyl amino or O-alkyl;

R 13 is independently selected from H and F;

R 14 is independently selected from H and F;

W is —C(O)NR 4 OR 15 , and

R 15 is C 1 -C 4 alkyl or C 1 -C 4 alkenyl optionally substituted with 1 to 3 substituents OH, O-Me, NH 2 , N(methyl) 2 or N(ethyl) 2 .

5. The compound of Formula (II) according to claim 1 , wherein:

W is —C(O)NR 4 OR 15 ;

R 4 is hydrogen;

R 15 is selected from C 1 -C 4 alkyl or C 1 -C 4 alkenyl that may be further substituted by 1 or 2 of OH, O—C 1 -C 4 alkyl or NR′R″; and

R′ and R″ are independently hydrogen, methyl or ethyl.

6. A pharmaceutical composition which comprises a compound of claim 1 and a pharmaceutically acceptable excipient.