Novel hetaryl-phenylenediamine-pyrimidines as protein kinase inhibitors

Compounds of the general formula (I) with building blocks A, B, C and D,

• in which
• R1 is halogen, —CF3, —OCF3, C1-C4-alkyl or nitro,
• R2 is a C1-C10-alkyl, C2-C10-alkenyl or C2-C10-alkynyl radical, a C3-C7-cycloalkyl or a heterocyclyl ring having 3 to 7 ring atoms, in each case optionally substituted one or more times, identically or differently, by hydroxy, —NR8R9, —NR7—C(O)—R12, —NR7—C(O)—OR12, —NR7—C(O)—NR8R9 or a monocyclic or bicyclic heteroaryl which is optionally itself substituted one or more times by hydroxy or a C1-C6-alkyl radical.
• R3 is
• (i) hydroxy, halogen, cyano, nitro, —CF3, —OCF3, —C(O)NR8R9, —C(S)NR8R9, —NR8R9, —NR7—C(O)—R2, —NR7—C(O)—OR2, —NR7—C(O)—NR8R9 or —NR7—SO2—R12 and/or
• (ii) a C1-C5-alkyl and/or C1-C5-alkoxy radical which is optionally substituted one or more times, identically or differently, by halogen, hydroxy, C1-C6-alkoxy, —CF3, —OCF3 or —NR8R9,
• m is 0-3,
• R4 and R5 are independently of one another
• (iii) hydrogen, —NHR8, —OR8, halogen, —(CO)—NR8R9 and/or
• (iv) a C1-C4-alkyl, C3-C5-alkenyl, C3-C5-alkynyl radical or a C3-C6-cycloalkyl ring, in each case optionally themselves substituted one or more times, identically or differently, by hydroxy, —NR8R9, cyano, halogen, —CF3, C1-C6-alkoxy, —OCF3 and/or C1-C6-alkyl,
• X and Y are independently of one another
• —O—, —S—, —S(O)—, —S(O)2— or —NR5—, where
• R15 is hydrogen or a C1-C6-alkyl radical, C3-C8-cycloalkyl or a heterocyclyl ring having 3 to 8 ring atoms, in each case optionally substituted one or more times, identically or differently, by hydroxy, —NR10R11, cyano, halogen, —CF3, C1-C6-alkoxy and/or —OCF3, or
• if X is —NR15—,
• —NR15— and R2 preferably alternatively together form a 3 to 6 membered ring which, in addition to the nitrogen atom, optionally comprises a further heteroatom, is optionally substituted one or more times, identically or differently, by hydroxy, C1-C6-alkyl, C1-C6-alkoxy,
• —C(O)R12, —SO2R12, halogen or the group —NR8R9, optionally comprises 1 or 2 double bonds, and/or is interrupted by a —C(O) group.
• Q is a monocyclic or bicyclic heteroaryl ring,
• R6 is
• (iii) hydrogen or
• (iv) a C1-C4-alkyl, C3-C5-alkenyl, C3-C5-alkynyl or C1-C5-alkoxy radical, a C3-C6-cycloalkyl or phenyl ring, a heterocyclyl ring having 3 to 6 ring atoms or a monocyclic heteroaryl ring, in each case optionally themselves substituted one or more times, identically or differently, by hydroxy, —NR8R9, cyano, halogen, —CF3, C1-C6-alkoxy and/or —OCF3.
• R7 is hydrogen,
• R8 and R9 are independently of one another
• hydrogen and/or a C1-C5-alkyl, C2-C5-alkenyl radical, a C3-C7-cycloalkyl and/or phenyl ring and/or a monocyclic heteroaryl ring, in each case optionally substituted one or more times, identically or differently, by hydroxy, —NR10R11, —NR7—C(O)—R12 and/or C1-C6-alkoxy, or
• R8 and R9 form together with the nitrogen atom a 5- to 7-membered ring which, in addition to the nitrogen atom, optionally comprises 1 further heteroatom and which may be substituted one or more times, identically or differently, by hydroxy, —NR10R11 and/or C1-C6-alkoxy.
• R10 and R11 are independently of one another hydrogen or a C1-C6-alkyl radical which is optionally substituted one or more times, identically or differently, by hydroxy, halogen or C1-C6-alkoxy,
• R12 is a C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl radical, a C3-C7-cycloalkyl or phenyl ring, a heterocyclyl ring having 3 to 8 ring atoms or a monocyclic heteroaryl ring, in each case optionally themselves substituted one or more times, identically or differently, by hydroxy, halogen, nitro, —NR8R9, C1-C6-alkyl and/or C1-C6-alkoxy.
• R13 and R14 are independently of one another a C1-C6-alkyl, C2-C6-alkenyl and/or C2-C6-alkynyl radical, a C3-C7-cycloalkyl and/or phenyl ring, a heterocyclyl ring having 3 to 8 ring atoms and/or a monocyclic heteroaryl ring, in each case optionally themselves substituted one or more times, identically or differently, by hydroxy, —NR8R9 and/or C1-C6-alkoxy.
• R16 is a C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl radical, a C3-C7-cycloalkyl or phenyl ring, a heterocyclyl ring having 3 to 8 ring atoms or a monocyclic heteroaryl ring, in each case optionally themselves substituted one or more times, identically or differently, by hydroxy, —NR8R9, cyano, halogen, —CF3, C1-C6-alkoxy and/or —OCF3,
• and the salts, diastereomers and enantiomers thereof.