Substituted oxidole derivatives as protein tyrosine and as protein serine/threonine kinase inhibitors

A compound of formula (I):

• wherein
• X is N, CH, or C(C1-6 aliphatic);
• R1 and R2 together with the carbon atoms to which they are bound form a thiazole or thiazole substituted by halogen or oxo;
• R3 is hydrogen, C1-6 aliphatic, hydroxy, hydroxy C1-6 aliphatic, di-C1-6 aliphatic amino, di-C1-6 aliphatic aminocarbonyl, di-C1-6 aliphatic aminosulfonyl, C1-6 alkoxy, Aryl, Aryloxy, hydroxy-Aryl, or halogen, where Aryl is as defined below;
• R4 is R7-sulfonyl, R7-sulfonyl-C1-12 aliphatic, R7-aminosulfonyl, R7-aminosulfonyl-C1-12 aliphatic, R7-sulfonylamino, R7-sulfonylamino-C1-12 aliphatic, (R8)1-3-Arylamino, (R8)1-3-Arylsulfonyl, (R8)1-3-Aryl-aminosulfonyl, (R8)1-3-Aryl-sulfonylamino or pyridyl-amino, where R7, R8, and Aryl are as defined below;
• R5 is hydrogen;
• R7 is pyridyl, pyridyl-C1-12-aliphatic, pyridyl-C1-12-alkoxy, di-pyridyl-C1-12-alkoxy Aryl, Aryl-C1-12-aliphatic, Aryl-C1-12-alkoxy, or Aryl-carbonyl, where Aryl is as defined below;
• R8 is hydrogen or halo-C1-6 aliphatic;
• Aryl is phenyl, or naphthyl;
• and the pharmaceutically acceptable salts, solvates, or prodrugs thereof in either crystalline or amorphous form.

A compound of formula (I):

• wherein
• X is N, CH, or CCH3;
• R1 and R2 together with the carbon atoms to which they are bound form a fused thiazole or thiazole optionally substituted by halogen or oxo;
• R3 is hydrogen, C1-6 aliphatic, hydroxy, hydroxy C1-6 aliphatic, di-C1-6 aliphatic amino, di-C1-6 aliphatic aminocarbonyl, di-C1-6 aliphatic aminosulfonyl C1-6 alkoxy, Aryloxy, or halogen, where Aryl is as defined below;
• R4 is R7-sulfonyl, R7-sulfonyl C1-6-aliphatic, R7-aminosulfonyl, R7-aminosulfonyl C1-6 aliphatic, R7-C1-6 aliphatic aminosulfonyl-C1-6 aliphatic, Aryl, pyridyl, or R8-Aryl-aminosulfonyl, where R7, R8, and Aryl are as defined below;
• R5 is hydrogen;
• R7 is Aryl-carbonyl, Aryl, Aryl-C1-6-alkoxy, Aryl-C1-6-aliphatic, pyridyl, pyridyl-C1-6-alkoxy, di-pyridyl-C1-6-alkoxy, pyridyl-C1-6-aliphatic, or di-pyridyl-C1-6-aliphatic;
• R8 is trifluoromethyl;
• Aryl is phenyl;
• and the pharmaceutically acceptable salts, solvates, or prodrugs thereof in either crystalline or amorphous form.

A compound of formula (I):

• wherein
• X is CH;
• R1 and R2 together with the carbon atoms to which they are bound form a fused thiazole or thiazole optionally substituted by halogen, nitro, cyano, C1-12 alkoxy, carbonyl-C1-12 alkoxy or oxo;
• R3 is hydrogen, C1-12 aliphatic, hydroxy, hydroxy C1-12 aliphatic, di-C1-12 aliphatic amino, di-C1-12 aliphatic aminocarbonyl, di-C1-12 aliphatic aminosulfonyl, C1-12 alkoxy, Aryl, Aryloxy, hydroxy-Aryl, or halogen, where Aryl is as defined below;
• R4 is R7-aminosulfonyl, R7-aminosulfonyl-C1-12 aliphatic, R7-sulfonylamino, R7-sulfonylamino-C1-12 aliphatic, (R8)1-3-Aryl-aminosulfonyl, or (R8)1-3-Aryl-sulfonylamino, where R7, R8, or Aryl are as defined below;
• R5 is hydrogen;
• R7 is pyridyl, pyridyl-C1-12-aliphatic, pyridyl-C1-12-alkoxy, di-pyridyl-C1-12-alkoxy Aryl, Aryl-C1-12-aliphatic, Aryl-C1-12-alkoxy, or Aryl-carbonyl, where Aryl is as defined below;
• R8 is hydrogen, nitro, cyano, C1-12 alkoxy, halo, carbonyl-C1-12 alkoxy or halo-C1-12 aliphatic;
• Aryl is phenyl, naphthyl, phenanthryl or anthracenyl;
• and the pharmaceutically acceptable salts, solvates, or prodrugs thereof in either crystalline or amorphous form.