Triazolopyridazines as PAR1 inhibitors, production thereof, and use as medicaments

A compound of formula I

• or a stereoisomeric or tautomeric form thereof, or a physiologically compatible salt of any of them, where
• Q1 is a hydrogen atom, —(C1-C6)-alkyl, —(C3-C6)-cycloalkyl, —OH,
• —O—(C1-C6)-alkyl or —O—(C3-C6)-cycloalkyl, where alkyl and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or
• —O—(C3-C6)-cycloalkyl, where some or all of the hydrogen atoms in alkyl or cycloalkyl may be replaced by fluorine,
• Q2 and Q3 are the same or different and are each independently a hydrogen atom, —(C1-C6)-alkyl or —(C3-C6)-cycloalkyl, where some or all of the hydrogen atoms in alkyl or cycloalkyl may be replaced by fluorine,
• R1, R2 and R3 are the same or different and are each independently a hydrogen atom, —(C1-C6)-alkyl, —(C3-C6)-cycloalkyl, —O—(C1-C8)-alkyl,
• —O—(C3-C6)-cycloalkyl, —(C0-C4)-alkylene-C(O)—N(R11)-R12,
• —(C0-C4)-alkylene-C(O)—O—R11, —(C0-C4)-alkylene-C(O)—R11,
• —(C0-C4)-alkylene-N(R11)-R12, —(C0-C4)-alkylene-N(R11)-C(O)—R12, halogen, OH, —CN, —NO2, —SO2CH3, —SO2CF3, —SF5, —Si[—(C1-C4)-alkyl]3,
• —(C1-C6)-alkylene-O—(C1-C6)-alkyl, —O—(C1-C6)-alkylene-O—(C1-C6)-alkyl,
• —O—(C0-C4)-alkylene-(C6-C14)-aryl where aryl is unsubstituted or mono-, di- or trisubstituted independently by —O—(C1-C6)-alkyl,
• —(C1-C4)-alkyl, OH, —(C3-C6)-cycloalkyl or —O—(C3-C6)-cycloalkyl, —O—(C1-C4)-alkylene-(C3-C6)-cycloalkyl, -(C4-C15)-Het,
• where Het is unsubstituted or mono-, di- or trisubstituted independently by —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or —O—(C3-C6)-cycloalkyl or
• —O—(C1-C6)-alkylene-O—(C1-C6)-alkylene-O—(C1-C6)-alkyl, where alkyl, alkylene and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl, —(C6-C14)-aryl where aryl is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen,
• —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or
• —O—(C3-C6)-cycloalkyl,
• —(C4-C15)-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen, —(C1-C4)-alkyl,
• —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or —O—(C3-C6)-cycloalkyl, or
• —O—(C3-C6)-cycloalkyl, or
• where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine, or
• R1 and R2 or R2 and R3, together with the ring atoms to which they are each bonded, form a 5- to 8-membered ring, where the ring consists only of carbon atoms or 1, 2 or 3 of these atoms are replaced by nitrogen, oxygen or sulfur atoms, where the ring is unsubstituted or mono- or disubstituted independently by —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH,
• —O—(C1-C6)-alkyl or —O—(C3-C6)-cycloalkyl, where some or all of the hydrogen atoms in the 5- to 8-membered ring formed, and in alkyl or cycloalkyl, may be replaced by fluorine,
• R11 and R12 are each independently a hydrogen atom, —(C1-C6)-alkyl,
• —(C3-C6)-cycloalkyl, —(C0-C4)-alkylene-(C6-C14)-aryl where aryl is unsubstituted or mono-, di- or trisubstituted independently by
• —O—(C1-C6)-alkyl, —(C1-C4)-alkyl, OH, —(C3-C6)-cycloalkyl or
• —O—(C3-C6)-cycloalkyl,
• —(C0-C4)-alkylene-(C4-C15)-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen,
• —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or
• —O—(C3-C6)-cycloalkyl,
• —SO2CH3 or —SO2CF3,
• where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine, or
• R11 and R12 in the “N(R11)-R12” and “N(R11)-C(O)—R12” fragments represent a 5- to 8-membered ring which is formed together with the nitrogen atom “N” or the “N—C(O)” group to form cyclic amines, imides or lactams which contain up to 2 further heteroatoms from the group of N, O and S, where the ring is unsubstituted or mono- or disubstituted independently by —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or —O—(C3-C6)-cycloalkyl, where some or all of the hydrogen atoms in the 5- to 8-membered ring formed, and in alkyl or cycloalkyl, may be replaced by fluorine,
• R4, R5, R6, R7 and R8 are the same or different and are each independently a hydrogen atom, —(C1-C6)-alkyl, —(C3-C6)-cycloalkyl, OH,
• —CN, —NO2, —O—(C1-C8)-alkyl, —O—(C3-C6)-cycloalkyl,
• —(C0-C4)-alkylene-(CO)—N(R21)-R22, —SO2CH3, —SO2CF3,
• —(C0-C4)-alkylene-C(O)—O—R21, halogen, —SF5,
• —(C0-C4)-alkylene-C(O)—R21, —(C0-C4)-alkylene-N(R21)-R22,
• —(C0-C4)-alkylene-N(R21)-C(O)—R22, —(C1-C6)-alkylene-O—(C1-C6)-alkyl,
• —(C0-C6)-alkylene-O—(C1-C6)-alkylene-O—(C1-C6)-alkyl, —Si[—(C1-C4)-alkyl]3,
• —(C0-C6)-alkylene-O—(C1-C4)-alkylene-(C3-C6)-cycloalkyl,
• —(C0-C6)-alkylene-O—(C0-C6)-alkylene-(C6-C14)-aryl where aryl is unsubstituted or mono-, di- or trisubstituted independently by —O—(C1-C6)-alkyl, —(C1-C4)-alkyl, OH,
• —(C3-C6)-cycloalkyl or —O—(C3-C6)-cycloalkyl, or —(C4-C15)-Het where Het is unsubstituted or mono-, di- or trisubstituted independently by —O—(C1-C6)-alkyl,
• —(C1-C4)-alkyl, OH, —(C3-C6)-cycloalkyl or —O—(C3-C6)-cycloalkyl,
• where alkyl, alkylene and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl, —(C6-C14)-aryl where aryl is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen,
• —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or
• —O—(C3-C6)-cycloalkyl,
• —(C4-C15)-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen, —(C1-C4)-alkyl,
• —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or —O—(C3-C6)-cycloalkyl, or
• —O—(C3-C6)-cycloalkyl,
• where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine, or
• R4 and R5, R5 and R6, R6 and R7 or R7 and R8, together with the ring atoms to which they are each bonded, form a 5- to 8-membered ring, where the ring consists only of carbon atoms or 1, 2 or 3 of these atoms are replaced by nitrogen, oxygen or sulfur atoms, where the ring is unsubstituted or mono- or disubstituted independently by —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or
• —O—(C3-C6)-cycloalkyl, where some or all of the hydrogen atoms in the 5- to 8-membered ring formed, and in alkyl or cycloalkyl, may be replaced by fluorine,
• R21 and R22 are each independently a hydrogen atom, —(C1-C6)-alkyl,
• —(C3-C6)-cycloalkyl, —(C0-C4)-alkylene-(C6-C14)-aryl where aryl is unsubstituted or mono-, di- or trisubstituted independently by
• —O—(C1-C6)-alkyl, —(C1-C4)-alkyl, OH, —(C3-C6)-cycloalkyl or
• —O—(C3-C6)-cycloalkyl,
• —(C0-C4)-alkylene-(C4-C15)-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen,
• —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or
• —O—(C3-C6)-cycloalkyl,
• —SO2CH3 or —SO2CF3,
• where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine, or
• R21 and R22 in the “N(R21)-R22” and “N(R21)-C(0)-R22” fragments represent a 5- to 8-membered ring which is formed together with the nitrogen atom “N” or the “N—C(O)” group to form cyclic amines, imides or lactams which contain up to 2 further heteroatoms from the group of N, O and S, where the ring is unsubstituted or mono- or disubstituted independently by —(C1-C4)-alkyl, —(C3-C6)-cycloalkyl, OH, —O—(C1-C6)-alkyl or —O—(C3-C6)-cycloalkyl, where some or all of the hydrogen atoms in the 5- to 8-membered ring formed, and in alkyl or cycloalkyl, may be replaced by fluorine.