Thiazolidinones and the use therof as polo-like kinase inhibitors

Compounds of general formula I

• in which
• X and Y are the same or different and stand for hydrogen, aryl, cyano, C3-C6-cycloalkyl or for the group —COOR4, —CONR15—(CH2)n—R25, —COOR25, —CONR15R16 or —COR13,
• R1, R11, R12
• R15 R16
• R19 and R20 are the same or different and stand for hydrogen, C1-C10-alkyl, C2-C10 alkenyl, C2-C10-alkinyl, (COOR14)—(CH2)n—, (C3-C6-cycloalkyl)-C1-C4-alkylene, C3-C6-cycloalkyl, phenylsulfonyl, phenyl-C3-C6-cycloalkyl, C1-C10-alkanoyl, C1-C6-alkoxy-C1-C6-alkylene, C1-C4-alkoxycarbonyl-C1-C4-alkylene, hydroxy-C1-C4-alkylene, —C1-C6-alkyl-O—Si(phenyl)2—C1-C6-alkyl, or for the group COOR14, —COR13, —SO2R18, —(CH2)n—NR15R16 or —(CH2)n—C(CH3)q—(CH2)nNR15R16 or —NR11R12, or
• or for aryl, heteroaryl, heterocyclyl, aryl-C1-C4-alkylene, heteroaryl-C1-C4-alkylene, aryloxy-C1-C4-alkylene, heteroaryloxy-C1-C4-alkylene or aryl-C1-C4-alkylenoxy-C1-C4-alkylene that is optionally substituted in one or more places in the same way or differently with C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, phenyl, cyano, halogen, hydroxy, C1-C4-alkoxy, phenoxy, benzyloxy, C1-C4-alkylsulfanyl, benzylsulfanyl, phenylsulfanyl, dimethylamino, acetylamino, trifluoromethyl, trifluoromethoxy, trifluoromethylsulfanyl, acetyl, —CO—C1-C6-alkyl, 1-iminoethyl or nitro, or for C1-C10-alkyl that is substituted in one or more places with fluorine,
• R2 and R3 are the same or different and stand for hydrogen, C1-C6-alkyl, hydroxy-C1-C6-alkylene, C3-C6-cyclohexyl or for the group —COOR14, —CONR15R16, —COR13, —SO2R18, —NR11R12, —(CH2)n-A,
• or for aryl, hetaroaryl or heterocyclyl that is optionally substituted in one or more places in the same way or differently with C1-C6-alkyl, C3-C6-cycloalkyl, halo-C1-C6-alkyl, halo-C1-C6-alkoxy, halogen, cyano, hydroxy-C1-C6-alkylene, hydroxy-C1-C6-alkylenoxy, aryl, heteroaryl, heterocyclyl, —C1-C6-alkyl-COOR8 or with the group —OR10, —COR13, —COOR14, —NR11R12, —NR11—CO—NR11R12—NR11—CO—R13, —NR11—SO2—R13, —(CH2)n—CO—NR15R16, —SR10 or —SO2R18,
• R4 R8, R9, R10,
• R13, R14, R17
• and R18 are the same or different and stand for hydrogen, C1-C10-alkyl, hydroxy-C1-C6-alkylenoxy-C1-C6-alkylene, C1-C6-alkoxy-CO—C1-C6-alkylene, —(CH2)n-CO—NR15R16, C2-C10-alkenyl, C2-C10-alkinyl, (C3-C6-cycloalkyl)-C1-C4-alkylene, halo-C1-C6-alkyl, hydroxy-C1-C6-alkylene, (COOR14)—(CH2)n—, hydroxy-(CH2)n—O—(CH2)n, C3-C6-cycloalkyl, C1-C10-alkanoyl, or for the group —NR11R12, —(CH2)n—CO—R25, —(CH2)n—NR15R16, COOR14—(CH2)n— or —COR13, or for aryl, heteroaryl, heterocyclyl, aryl-C1-C4-alkylene, heteroaryl-C1-C4-alkylene, aryloxy-C1-C4-alkylene, heteroaryloxy-C1-C4-alkylene or aryl-C1-C4-alkylenoxy-C1-C4-alkylene that is optionally substituted in one or more places in the same way or differently with C1-C6-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, phenyl, cyano, halogen, hydroxy-C1-C6-alkyl, C1-C4-alkoxy, phenoxy, benzyloxy, C1-C4-alkylsulfanyl, benzylsulfanyl, phenylsulfanyl, dimethylamino, acetylamino, trifluoromethyl, trifluoromethoxy, trifluoromethylsulfanyl, acetyl, —CO—C1-C6-alkyl, 1-iminoethyl or nitro, or for C1-C10-alkyl that is substituted in one or more places with fluorine or for the group NR11R12, —COR13, —SO2R18, —(CH2)n—NR15R16, —(CH2)n—C(CH3)q—(CH2)nNR15R16 or
• or
• R2 and R3,
• R11 and R12,
• R15 and R16
• and
• R19 and R20, in each case independently of one another, together form a 3- to 10-membered ring, which optionally can contain one or more nitrogen, oxygen or sulfur atoms,
• or
• R3 stands for hydrogen,
• and
• R2 stands for the group -(L-M), in which
• L stands for a group —C(O)—, —S(O)2, —C(O)N(R7)—, —S(O)2N(R7)—, —C(S)N(R7)—, —C(S)N(R7)C(O)O—, —C(O)O— or —C(O)S—, and
• M stands for hydrogen, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkinyl, (C3-C6-cycloalkyl)-C1-C4-alkylene, C3-C6-cycloalkyl, phenyl-C3-C6-cycloalkyl, C1-C10-alkanoyl, C1-C4-alkoxy-C1-C4-alkylene, C1-C4-alkoxycarbonyl-C1-C4-alkylene, hydroxy-C1-C10-alkylene, or for aryl, heteroaryl, heterocyclyl, aryl-C1-C4-alkylene, heteroaryl-C1-C4-alkylene, aryloxy-C1-C4-alkylene, heteroaryloxy-C1-C4-alkylene or aryl-C1-C4-alkylenoxy-C1-C4-alkylene that is optionally substituted in one or more places in the same way or differently with C1-C4-alkyl, C2-C6-alkenyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, phenyl, cyano, halogen, phenoxy, benzyloxy, halo-C1-C4-alkoxy, halo-C1-C6-alkyl, nitro, —C1-C6-alkylCOOR8, —C2-C6-alkenylCOOR8, —C2-C6-alkinylCOOR8, —C1-C6-alkylOR9, —C2-C6-alkenylOR9, —C1-C6-alkinylOR9 or with the group —OR10, —NR11R12, —COR13, —COOR14, —CONR15R16, —SR17, —SO2R18, SO2NR19R20 or —C(NH)(NH2), or for C1-C10-alkyl that is substituted in one or more places with fluorine, and
• R7 stands for hydrogen, C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkinyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)-C1-C4-alkylene, aryl-C1-C4-alkylene,
• A stands for optionally substituted aryl, heteroaryl or heterocyclyl,
• R22 stands for hydrogen, hydroxy-C1-C6-alkyl, or for the group —OR10, —NR11R12, —COR13, —CONR15R16, —SO2R18, —NR15—(C═S)—NR16—(CH2)n—R24, —NR15—(C═O)—NR16—(CH2)n—R24,
• R23 stands for hydrogen or C1-C6-alkyl,
• R24 stands for hydrogen, phenyl, C1-C6-alkoxy or for the group —(CH2)n—COO—C1-C6-alkyl,
• R25 stands for the group —OR10 or for C2-C6-alkenyl, phenyl, pyridyl, imidazolyl, morpholinyl, piperidinyl, C3-C6-cycloalkyl or
• that is optionally substituted in one or more places in the same way or differently with halogen, C1-C6-alkyl, hdyroxy-C1-C6-alkyl or with the group —OR10 or —COOR14,
• m, p, k, in each case independently of one another, stand for 0 or 1,
• n stands for 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
• q stands for 1 or 2, as well as their stereoisomers, mixtures of stereosiomers and their salts.