Heterocyclically substituted benzoylureas, process for their preparation and their use as pharmaceuticals

A compound of the formula I,

• wherein
• R1 and R2 are each independently H, O—(C1–C6)-alkyl, CO—(C1–C6)-alkyl, COO—(C1–C6)-alkyl, (C1–C6)-alkylene-COOH, (C1–C6)-alkylene-COO—(C1–C6)-alkyl or (C1–C6)-alkyl, wherein said (C1–C6)-alkyl is optionally substituted by OH, O—(C1–C4)-alkyl, NH2, NH(C1–C4)-alkyl or N[(C1–C6)-alkyl]2;
• R3 and R4 are each independently F, Cl, Br, OH, NO2, CN, (C1–C6)-alkyl, O—(C1–C4)-alkyl, O—(C2–C6)-alkenyl or (C2–C6)-alkynyl, wherein said (C1–C6)-alkyl, O—(C1–C4)-alkyl, O—(C2–C6)-alkenyl and (C2–C6)-alkynyl are optionally mono- or polysubstituted by F, Cl or Br;
• R5 is H, F, Cl, Br, OH, NO2, CN, (C1–C6)-alkyl, O—(C1–C4)-alkyl, CO—(C1–C6)-alkyl, (C0–C6)-alkylene-COOH, (C0–C6)-alkylene-COO—(C1–C6)-alkyl, SO2—(C1–C6)-alkyl, O—(C2–C6)-alkenyl or (C2–C6)-alkynyl, wherein said (C1–C6)-alkyl, O—(C1–C4)-alkyl, CO—(C1–C6)-alkyl, (C0–C6)-alkylene-COOH, (C0–C6)-alkylene-COO—(C1–C6)-alkyl, SO2—(C1–C6)-alkyl, O—(C2–C6)-alkenyl and (C2–C6)-alkynyl are optionally mono- or polysubstituted by F, Cl or Br;
• A is H, F, Cl, Br, OH, NO2, CN, (C1–C6)-alkyl, CO—(C1–C6)-alkyl, (C1–C6)-alkylene-COOH, (C1–C6)-alkylene-COO(C1–C6)-alkyl, SO2—(C1–C6)-alkyl, (C2–C6)-alkenyl, (C2–C6)-alkynyl, O—(C1–C6)-alkyl, S(O)1-2—(C1–C6)-alkyl-, NH—(C1–C6)-alkyl, N—[(C1–C6)-alkyl]2, COO—(C1–C6)-alkyl, CONH2, CONH—(C1–C6)-alkyl, CON—[(C1–C6)-alkyl]2, SO2NH2, SO2NH—(C1–C6)-alkyl, SO2N—[(C1–C6)-alkyl]2 or NHCOR6,
• wherein said (C1–C6)-alkyl, CO—(C1–C6)-alkyl, (C1–C6)-alkylene-COOH, (C1–C6)-alkylene-COO(C1–C6)-alkyl, SO2—(C1–C6)-alkyl, (C2–C6)-alkenyl, (C2–C6)-alkynyl, O—(C1–C6)-alkyl, S(O)1-2—(C1–C6)-alkyl-, NH—(C1–C6)-alkyl, N—[(C1–C6)-alkyl]2, COO—(C1–C6)-alkyl, CONH—(C1–C6)-alkyl, CON—[(C1–C6)-alkyl]2, SO2NH—(C1–C6)-alkyl and SO2N—[(C1–C6)-alkyl]2 are optionally mono- or polysubstituted by F, Cl, Br, COOH, COO—(C1–C6)-alkyl, CONH2, CONH—(C1–C6)-alkyl, CON[(C1–C6)-alkyl]2 or OCO—(C1–C6)-alkyl;
• R6 is H, (C1–C6)-alkyl, (C3–C7)-cycloalkyl, (C3–C7)-cycloalkyl-(C1–C4)-alkylene, (C2–C6)-alkenyl, (C2–C6)-alkynyl, (C1–C6)-alkylene-COO—(C1–C6)-alkyl, (C1–C6)-alkylene-CO—(C1–C6)-alkyl, (C0–C6)-alkylene-COOH, (C1–C6)-alkylene-CONH2, (C6–C10)-aryl, (C1–C4)-alkylene-(C6–C10)-aryl, heteroaryl, (C1–C4)-alkylene-heteroaryl or CO-heteroaryl, wherein said (C1–C6)-alkyl, (C3–C7)-cycloalkyl, (C3–C7)-cycloalkyl-(C1–C4)-alkylene, (C2–C6)-alkenyl, (C2–C6)-alkynyl, (C1–C6)-alkylene-COO—(C1–C6)-alkyl, (C1–C6)-alkylene-CO—(C1–C6)-alkyl, (C0–C6)-alkylene-COOH and (C1–C6)-alkylene-CONH2 are optionally mono- or polysubstituted by F, Cl, Br, O(C1–C4-alkyl), COO—(C1–C4-alkyl) or N—[(C1–C4)-alkyl]2 and said (C6–C10)-aryl, (C1–C4)-alkylene-(C6–C10)-aryl, heteroaryl, (C1–C4)-alkylene-heteroaryl and CO-heteroaryl are optionally mono- or polysubstituted by F, Cl, Br, NO2, CN, O—(C1–C4-alkyl), S—COO(C1–C4-alkyl), COO—(C1–C4-alkyl), N—[(C1–C4)-alkyl]2 or (C1–C6)-alkyl;
• n is 0, 1, 2 or 3;
• m is 1, 2, 3, 4 or 5;
• o is 0, 1, 2 or 3;
• Het is a heterocyclic 4- to 7-membered ring which may contain up to four N, O or S heteroatoms and wherein said heterocyclic 4- to 7-membered ring is optionally substituted by R7, R8 and R9, with the proviso that said heterocyclic 4- to 7-membered ring cannot be pyrrole;
• and
• R7, R8, and R9 are each independently H, F, Cl, Br, (C1–C6)-alkyl, O—(C1–C6)-alkyl, O—(C2–C6)-alkenyl, O—(C2–C6)-alkynyl, OH, oxo, O—(C1–C6)-alkyl, NH2, NH—(C1–C6)-alkyl, N—[(C1–C6)-alkyl]2, COOH, CO—(C1–C6)-alkyl, COO—(C1–C6)-alkyl, CONH2, CONH—(C1–C6)-alkyl, CON—[(C1–C6)-alkyl]2, (C0–C6)-alkylene-aryl or (C1–C6)-alkylene-COO—(C1–C6)-alkyl, wherein said (C1–C6)-alkyl, O—(C1–C6)-alkyl, O—(C2–C6)-alkenyl, O—(C2–C6)-alkynyl, O—(C1–C6)-alkyl, NH—(C1–C6)-alkyl, N—[(C1–C6)-alkyl]2, CO—(C1–C6)-alkyl, COO—(C1–C6)-alkyl, CONH—(C1–C6)-alkyl, CON—[(C1–C6)-alkyl]2, (C0–C6)-alkylene-aryl and (C1–C6)-alkylene-COO—(C1–C6)-alkyl are optionally substituted by COOH, CONH2, CONH—(C1–C6)-alkyl, CON—[(C1–C6)-alkyl]2, OCO—(C1–C6)-alkyl, F, Cl, (C1–C6)-alkyl or O—(C1–C6)-alkyl;
• and two radicals selected from said R7, R8 and R9 may optionally be bonded together to form a ring fused onto said heterocyclic 4- to 7-membered ring;
• and pharmaceutically acceptable salts thereof.