Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals

A compound of formula I,

• 10
• wherein:
• R1 and R4 are each, independently,
• H;
• C1-C10-alkyl, C2-C10-alkenyl or C2-C10-alkynyl, each of which is optionally substituted one or more times by F, OH, C1-C8-alkoxy, C1-C8-alkylmercapto, —CN, COOR6, CONR7R8, phenyl or heteroaryl, wherein the phenyl and heteroaryl are each independently optionally substituted one or more times by halogen, —CN, C1-C3-alkyl, C1-C3-alkoxy or CF3;
• phenyl or heteroaryl, each of which is optionally substituted one or more times by halogen, —CN, C1-C3-alkyl, C1-C3-alkoxy or CF3;
• COR9;
• CONR10R11;
• COOR12;
• CF3;
• halogen;
• —CN;
• NR13R14;
• OR15;
• S(O)mR16;
• SO2NR17R18;
• or
• NO2;
• R2 and R3 are each, independently,
• H;
• halogen;
• —CN;
• C1-C10-alkyl, optionally substituted one or more times by OH, phenyl, or heteroaryl;
• OH;
• C1-C10-alkoxy;
• phenoxy;
• S(O)mR19;
• CF3;
• NO2;
• C1-C10-alkylamino;
• di(C1-C10-alkyl)amino;
• (C1-C6-alkyl)-CONH—;
• phenyl-CONH— or phenyl-SO2—O—, wherein the phenyl is optionally substituted one or more times by halogen, —CN, methyl or methoxy;
• C1-C6-alkyl-SO2—O—;
• (C1-C6-alkyl)-CO—, wherein the C1-C6-alkyl is optionally substituted one or more times by F, di(C1-C3-alkyl)amino, pyrrolidinyl or piperidinyl;
• or
• phenyl-CO—, wherein the phenyl is optionally substituted one or more times by C1-C3-alkyl, halogen or methoxy;
• R5 is Ar or Hetar, each of which is optionally substituted one or more times by
• halogen;
• —CN;
• NH2;
• C1-C10-alkyl, C2-C10-alkenyl, C2-C10-alkynyl, C1-C10-alkoxy, C1-C10-alkylamino or di(C1-C10-alkyl)amino, wherein the alkyl, alkenyl, alkynyl and alkoxy are each independently optionally substituted one or more times by F, OH, C1-C8-alkoxy, aryloxy, C1-C8-alkylmercapto, NH2, C1-C8-alkylamino or di(C1-C8-alkyl)amino;
• C3-C5-alkandiyl;
• phenyl;
• heteroaryl;
• aryl-substituted or heteroaryl-substituted C1-C4-alkyl;
• CF3;
• NO2;
• OH;
• phenoxy;
• benzyloxy;
• (C1-C10-alkyl)-COO—;
• S(O)mR2;
• SH;
• phenylamino;
• benzylamino;
• (C1-C10-alkyl)-CONH—;
• (C1C10-alkyl)-CO—N(C1-C4-alkyl)-;
• phenyl-CONH—;
• phenyl-CO—N(C1-C4-alkyl)-;
• heteroaryl-CONH—;
• heteroaryl-CO—N(C1-C4-alkyl)-;
• (C1-C10-alkyl)-CO—;
• phenyl-CO—;
• heteroaryl-CO—;
• CF3—CO—;
• —OCH2O—;
• —OCF2O—;
• —OCH2CH2O—;
• —CH2CH2O—;
• COOR21;
• CONR22R23;
• C(NH)—NH2;
• SO2NR24R25;
• R26SO2NH—;
• R27SO2N(C1-C6-alkyl)-;
• or
• a residue of a saturated or unsaturated aliphatic, monocyclic 5-membered to 7-membered heterocycle containing 1, 2 or 3 heteroatoms selected from the group consisting of N, O and S, wherein the heterocycle is optionally substituted one or more times by halogen, C1-C3-alkyl, C1-C3-alkoxy, OH, oxo or CF3, and the heterocycle is optionally condensed to the group Ar or the group Hetar;
• wherein all aryl, heteroaryl, phenyl, aryl-containing, heteroaryl-containing and phenyl-containing groups, which are optionally present in the said substituents of the said group Ar or the said group Hetar, can be substituted by one or more substituents selected from the group consisting of halogens, —CN, C1-C3-alkyl, OH, C1-C3-alkoxy, and CF3;
• R6 is H;
• C1-C10-alkyl, optionally substituted one or more times by F, C1-C8-alkoxy or di(C1-C8-alkyl)amino;
• aryl-(C1-C4-alkyl)- or heteroaryl-(C1-C4-alkyl)-either of which is optionally substituted one or more times by halogen, C1-C4-alkyl, C1-C4-alkoxy or di(C1-C6-alkyl)amino;
• R7 is H;
• C1-C10-alkyl, optionally substituted one or more times by F, C1-C8-alkoxy, di(C1-C8-alkyl)amino or phenyl;
• or
• phenyl, indanyl or heteroaryl, each of which is optionally substituted one or more times by halogen, —CN, C1-C3-alkyl, C1-C3-alkoxy or CF3;
• R8 is H or C1-C10-alkyl;
• R9 is C1-C10-alkyl, optionally substituted one or more times by F, C1-C4-alkoxy or di(C1-C3-alkyl)amino;
• or
• phenyl or heteroaryl, each of which is optionally substituted one or more times by C1-C3-alkyl, C1-C3-alkoxy, halogen, —CN or CF3;
• R10, independently from R7, is R7;
• R11, independently from R8, is R8;
• R12, independently from R6, is R6;
• R13 is H;
• C1-C6-alkyl;
• or
• phenyl, benzyl, heteroaryl, (C1-C6-alkyl)-CO—, phenyl-CO—, or heteroaryl-CO—, each of which is optionally substituted one or more times by halogen, —CN, C1-C3-alkyl, C1-C3-alkoxy or CF3;
• R14, independently from R13, is R13;
• R15 is H;
• C1-C10-alkyl;
• (C1-C3-alkoxy)-C1-C3-alkyl-;
• benzyl, phenyl or heteroaryl, each of which is optionally substituted one or more times by halogen, —CN, C1-C3-alkyl, C1-C3-alkoxy or CF3;
• R16 is C1-C10-alkyl, optionally substituted one or more times by F, OH, C1-C8-alkoxy, aryloxy, C1-C8-alkylmercapto, C1-C8-alkylamino or di(C1-C8-alkyl)amino;
• CF3;
• or
• phenyl or heteroaryl, each of which is optionally substituted one or more times by halogen, —CN, C1-C3-alkyl, C1-C3-alkoxy or CF3;
• R17, independently from R7, is R7;
• R18, independently from R8, is R8;
• R19, independently from R16, is R16;
• R20, independently from R16, is R16;
• R21, independently from R6, is R6;
• R22, independently from R7, is R7;
• R23, independently from R8, is R8;
• R24, independently from R7, is R7;
• R25, independently from R8, is R8;
• R26, independently from R16, is R16;
• R27, independently from R16, is R16;
• R30 is H;
• C1-C10-alkyl, C2-C10-alkenyl or C2-C10-alkynyl, each of which is optionally substituted one or more times by F, OH, C1-C8-alkoxy, C1-C8-alkylmercapto, CN, COOR3 CON R32R33 NR34R35, (C1-C8-alkyl)-CONH—, (C1-C8-alkoxy)-CONH—, benzyloxy-CONH—, phenyl or heteroaryl, wherein the phenyl and heteroaryl are each independently optionally substituted one or more times by halogen, —CN, C1-C3-alkyl, C1-C3-alkoxy or CF3;
• or
• phenyl or heteroaryl, each of which is optionally substituted one or more times by halogen, —CN, C1-C3-alkyl, C1-C3-alkoxy or CF3;
• R31, independently from R6, is R6;
• R32, independently from R6, is R6;
• R33, independently from R6, is R6;
• R34, independently from R6, is R6;
• R35, independently from R6, is R6;
• X is NR30, S, O, CH═CH, N═CH or CH═N;
• heteroaryl is a residue of a 5-membered to 10-membered, aromatic, monocyclic or bicyclic heterocycle containing one or more heteroatoms selected from the group consisting of N, O and S;
• the group Hetar is a residue of a 5-membered to 10-membered, aromatic, monocyclic or bicyclic heterocycle containing one or more heteroatoms selected from the group consisting of N, O and S;
• aryl is phenyl, naphth-1-yl or naphth-2-yl;
• the group Ar is phenyl, naphth-1-yl or naphth-2-yl;
• and
• m is 0, 1 or 2;
• or a stereoisomer or a mixture of stereoisomers thereof in any ratio, or a pharmaceutically acceptable salt thereof.