Benzimidazol-2-amines as midh1 inhibitors
AssigneeBayer Pharma Aktiengesellschaft
InventorsHartmut REHWINKEL, Marcus BAUSER, Katja ZIMMERMANN, Stefan KAULFUß, Roland NEUHAUS
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Abstract
The present invention relates to benzim-idazol-2-amines of general formula (I) in which R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are as defined herein, to methods of preparing said compounds, to intermediate compounds useful for preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds and to the use of said compounds for manufacturing a pharmaceutical composition for the treatment or prophylaxis of a disease, in particular of neoplasms, as a sole agent or in combination with other active ingredients.
Claims27
A compound of formula (I)
- in which:
- R1 represents a halogen atom or group selected from:
- C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy, cyano, (C1-C6-alkyl)-S—, and (C1-C6-haloalkyl)-S—;
- R2 represents a hydrogen atom;
- R3 represents a hydrogen atom;
- R4 represents a hydrogen atom;
- R5 represents a hydrogen atom;
- R6 represents a group selected from:
- R13OC(═O)—(C1-C6-alkyl)-, R13OC(=O)—(C2-C6-alkenyl)-, R13OC(═O)—(C1-C6-alkoxy)-, R14(R15)NC(=O)—(C1-C6-alkyl)-, R14(R15)NC(═O)—(C2-C6-alkenyl)-, R14(R15)NC(═O)—(C1-C6-alkoxy)-, —C(═O)OR13, —C(═O)N(R14)R15, and —C(═O)N(R14)S(═O)2R16;
- R7 represents a hydrogen atom or a halogen atom or a C1-C3-alkyl group;
- R8 represents a C1-C3-alkyl group;
- R9, R10 , and R11
- are independently of each other selected from:
- hydrogen and C1-C3-alkyl;
- R12 represents a hydrogen atom;
- R13 represents a hydrogen atom or a group selected from:
- C1-C6-alkyl, C3-C6-cycloalkyl, HO—(C2-C6-alkyl)-, and (C1-C3-alkoxy)-(C2-C6-alkyl)-;
- R14 and R15
- are independently of each other selected from:
- hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, HO—(C2-C6-alkyl)-, (C1-C3-alkoxy)-(C2-C6-alkyl)-, C1-C6-haloalkyl, H2N-(C2-C6-alkyl)-, (C1-C3-alkyl)N(H)(C2-C6-alkyl)-, (C1-C3-alkyl)2N(C2-C6-alkyl)-, R13OC(═O)—(C1-C6-alkyl)-, 4- to 6-membered heterocycloalkyl, phenyl, heteroaryl, phenyl-(C1-C6-alkyl)-, and heteroaryl-(C i-C6-alkyl)-;
- wherein phenyl and heteroaryl groups are optionally substituted with one or two substituents, which are independently of each other selected from:
- C1-C3-alkyl, C3-C6-cycloalkyl, C1-C3-alkoxy, C3-C6-cycloalkyloxy, C1-C3-haloalkyl, C1-C3-haloalkoxy, halogen, cyano, —C(═O)OR13, and —C(═O)NH2;
- and, wherein said 4-6-membered heterocycloalkyl group is optionally substituted with one substituent selected from:
- C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, amino, hydroxy, halogen, and cyano;
- or said 4-6-membered heterocycloalkyl group is optionally substituted with one or two halogen atoms;
- or
- R14 and R15
- together with the nitrogen atom to which they are attached form a 4-6-membered heterocycloalkyl;
- said 4-6-membered heterocycloalkyl being optionally substituted with one substituent selected from:
- C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy, C1-C3-haloalkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, amino, hydroxy, halogen, and cyano;
- or said 4-6-membered heterocycloalkyl being optionally substituted with one or two halogen atoms;
- R16 represents a hydrogen atom or a group selected from:
- C1-C6-alkyl, HO—(C1-C6-alkyl)-, C3-C6-cycloalkyl, HO—(C3-C6-cycloalkyl)-, C1-C6-haloalkyl, (C1-C3-alkoxy)-(C1-C6-alkyl)-, phenyl, heteroaryl, and 4- to 6-membered heterocycloalkyl;
- wherein phenyl and heteroaryl groups are optionally substituted with one or two substituents, which are independently of each other selected from:
- C1-C3-alkyl, C3-C6-cycloalkyl, C1-C3-alkoxy, C3-C6-cycloalkyloxy, C1-C3-haloalkyl, C1-C3-haloalkoxy, halogen, cyano, —C(═O)OR13, and —C(═O)N(R14)R15;
- or a stereoisomer, a tautomer, an N-oxide, a hydrate, a solvate, or a salt thereof, or a mixture of same.
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25-26 (canceled)
Dependencies are inferred from the claim text.