Triazolium salts as PAR1 inhibitors, production thereof, and use as medicaments
The invention relates to novel compounds of formula I where X, A − , Q1, Q2, Q3, R2, R3, R4, R5, R6, R7, R8 and R9 are each as defined below. The compounds of formula I have antithrombotic activity and inhibit especially protease-activated receptor 1 (PAR1). The invention further relates to a process for preparing the compound of formula I and to the use thereof as a medicament.
1. A compound of formula I
or a stereoisomeric or tautomeric form thereof, or a physiologically compatible salt of any of them, where
X is C—R1,
A − is an anion of an organic or inorganic acid,
Q1 is a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-C(O)—O—R11, —(C 0 -C 4 )-alkylene-C(O)—N(R11)-R12, —(C 0 -C 4 )-alkylene-C(O)—R11, —OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, where alkyl and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl or —(C 3 -C 6 )-cycloalkyl, where some or all of the hydrogen atoms in alkyl or cycloalkyl may be replaced by fluorine,
R1, R2, R3 and R4 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —O—(C 1 -C 8 )-alkyl, —O—(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-C(O)—N(R11)-R12, —(C 0 -C 4 )-alkylene-C(O)—O—R11, —(C 0 -C 4 )-alkylene-N(R11)-C(O)—O—R12, —(C 0 -C 4 )-alkylene-C(O)—R11, —(C 0 -C 4 )-alkylene-N(R11)-R12, —(C 0 -C 4 )-alkylene-N(R11)-C(O)—R12, halogen, OH, —CN, —NO 2 ,
—SO 2 CH 3 , —SO 2 CF 3 , —SF 5 , —Si[—(C 1 -C 4 )-alkyl] 3 , —(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —O—(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl where aryl is unsubstituted or mono-, di- or trisubstituted independently by —O—(C 1 -C 6 )-alkyl,
—(C 1 -C 4 )-alkyl, OH, —(C 3 -C 6 )-cycloalkyl or —O—(C 3 -C 6 )-cycloalkyl, —O—(C 1 -C 4 )-alkylene-(C 3 -C 6 )-cycloalkyl, —(C 4 -C 15 )-Het where Het is unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl or —O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, where alkyl, alkylene and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl, —(C 6 -C 14 )-aryl where aryl is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen, —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, —(C 4 -C 15 )-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen, —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, or
—O—(C 3 -C 6 )-cycloalkyl,
where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine, or
R1 and R2, R2 and R3 or R3 and R4, 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 —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl, —(C 0 -C 4 )-alkylene-(C 4 -C 15 )-Het, —SO 2 CH 3 or —SO 2 CF 3 ,
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 —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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,
R5, R6, R7, R8 and R9 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —CN, —NO 2 , —O—(C 1 -C 8 )-alkyl, —O—(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-(CO)—N(R21)-R22, —SO 2 CH 3 , —SO 2 CF 3 , —(C 0 -C 4 )-alkylene-C(O)—O—R21, halogen, —SF 5 , —(C 0 -C 4 )-alkylene-C(O)—R21, —(C 0 -C 4 )-alkylene-N(R21)-R22, —(C 0 -C 4 )-alkylene-N(R21)-C(O)—R22, —(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —Si[—(C 1 -C 4 )-alkyl] 3 , —(C 0 -C 6 )-alkylene-O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —(C 4 -C 15 )-Het, —(C 0 -C 6 )-alkylene-O—(C 1 -C 4 )-alkylene-(C 3 -C 6 )-cycloalkyl or —(C 0 -C 6 )-alkylene-O—(C 0 -C 6 )-alkylene-(C 6 -C 14 )-aryl,
where alkyl, alkylene and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl, —(C 6 -C 14 )-aryl where aryl is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen,
—(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl,
—(C 4 -C 15 )-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen, —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, or —O—(C 3 -C 6 )-cycloalkyl,
where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine, or
R5 and R6, R6 and R7, R7 and R8 or R8 and R9, 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
—(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or
—O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl, —(C 0 -C 4 )-alkylene-(C 4 -C 15 )-Het, —SO 2 CH 3 or —SO 2 CF 3 , 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(O)—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 —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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.
2. A compound as claimed in claim 1 , wherein
X is C—R1,
A − is an anion of an organic or inorganic acid,
Q1 is a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-C(O)—O—R11, —(C 0 -C 4 )-alkylene-C(O)—N(R11)-R12, —(C 0 -C 4 )-alkylene-C(O)—R11, —OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, where alkyl and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl,
—(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl or —(C 3 -C 6 )-cycloalkyl, where some or all of the hydrogen atoms in alkyl or cycloalkyl may be replaced by fluorine,
R1, R2, R3 and R4 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —O—(C 1 -C 8 )-alkyl, —O—(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-C(O)—N(R11)-R12, —(C 0 -C 4 )-alkylene-N(R11)-C(O)—O—R12, —(C 0 -C 4 )-alkylene-C(O)—O—R11, —(C 0 -C 4 )-alkylene-C(O)—R11, —(C 0 -C 4 )-alkylene-N(R11)-R12, —(C 0 -C 4 )-alkylene-N(R11)-C(O)—R12, halogen, OH, —CN, —NO 2 , —SO 2 CH 3 ,
—SO 2 CF 3 , —SF 5 , —Si[—(C 1 -C 4 )-alkyl] 3 ,
—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl,
—O—(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl where aryl is unsubstituted or mono-, di- or trisubstituted independently by —O—(C 1 -C 6 )-alkyl,
—(C 1 -C 4 )-alkyl, OH, —(C 3 -C 6 )-cycloalkyl or —O—(C 3 -C 6 )-cycloalkyl,
—O—(C 1 -C 4 )-alkylene-(C 3 -C 6 )-cycloalkyl, —(C 4 -C 15 )-Het
where Het is unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, or
—O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl,
where alkyl, alkylene and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 4 )-alkyl, —(C 6 -C 14 )-aryl where aryl is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen,
—(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl,
—(C 4 -C 15 )-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen, —(C 1 -C 4 )-alkyl,
—(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, or —O—(C 3 -C 6 )-cycloalkyl,
where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine,
with the proviso that at least one R1, R2, R3 or R4 is not a hydrogen atom or R1 and R2, R2 and R3 or R3 and R4, 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 —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl, —(C 0 -C 4 )-alkylene-(C 4 -C 15 )-Het, —SO 2 CH 3 or —SO 2 CF 3 ,
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—(CO)” 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 —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, R8 and R9 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —CN, —NO 2 , —O—(C 1 -C 6 )-alkyl, —O—(C 3 -C 6 )-cycloalkyl,
—(C 0 -C 4 )-alkylene-(CO)—N(R21)-R22, —SO 2 CH 3 , —SO 2 CF 3 ,
—(C 0 -C 4 )-alkylene-C(O)—O—R21, halogen, —SF 5 ,
—(C 0 -C 4 )-alkylene-C(O)—R21, —(C 0 -C 4 )-alkylene-N(R21)-R22,
—(C 0 -C 4 )-alkylene-N(R21)-C(O)—R22, —(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl,
—(C 0 -C 6 )-alkylene-O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —Si[—(C 1 -C 4 )-alkyl] 3 ,
—(C 0 -C 6 )-alkylene-O—(C 1 -C 4 )-alkylene-(C 3 -C 6 )-cycloalkyl,
—(C 0 -C 6 )-alkylene-O—(C 0 -C 6 )-alkylene-(C 6 -C 14 )-aryl or —(C 4 -C 15 )-Het,
where alkyl, alkylene and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl, —(C 6 -C 14 )-aryl where aryl is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen,
—(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl,
—(C 4 -C 15 )-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen, —(C 1 -C 4 )-alkyl,
—(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, or —O—(C 3 -C 6 )-cycloalkyl,
where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine,
with the proviso that at least one R5, R6, R7, R8 or R9 is not a hydrogen atom, or
R5 and R6, R6 and R7, R7 and R8 or R8 and R9, 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
—(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or
—O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl, —(C 0 -C 4 )-alkylene-(C 4 -C 15 )-Het, —SO 2 CH 3 or —SO 2 CF 3 ,
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(O)—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 —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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.
3. A compound as claimed in claim 1 , wherein
X is C—R1,
A − is an anion of an organic or inorganic acid,
Q1 is a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl,
—(C 0 -C 4 )-alkylene-C(O)—O—R11, —(C 0 -C 4 )-alkylene-C(O)—N(R11)-R12,
—(C 0 -C 4 )-alkylene-C(O)—R11, —OH, —O—(C 1 -C 6 )-alkyl or
—O—(C 3 -C 6 )-cycloalkyl, where alkyl and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl,
—(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl or —(C 3 -C 6 )-cycloalkyl, where some or all of the hydrogen atoms in alkyl or cycloalkyl may be replaced by fluorine,
R1, R2, R3 and R4 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —O—(C 1 -C 8 )-alkyl, —O—(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-C(O)—N(R11)-R12,
—(C 0 -C 4 )-alkylene-C(O)—O—R11, —(C 0 -C 4 )-alkylene-N(R11)-C(O)—O—R12, —(C 0 -C 4 )-alkylene-C(O)—R11, —(C 0 -C 4 )-alkylene-N(R11)-R12, —(C 0 -C 4 )-alkylene-N(R11)-C(O)—R12, halogen, OH, —CN, —NO 2 , —SO 2 CH 3 , —Si[—(C 1 -C 4 )-alkyl] 3 , —(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —O—(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl, —O—(C 1 -C 4 )-alkylene-(C 3 -C 6 )-cycloalkyl, —(C 4 -C 15 )-Het or —O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl,
where alkyl, alkylene and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl,
where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine,
with the proviso that at least one R1, R2, R3 or R4 is not a hydrogen atom or
R1 and R2, R2 and R3 or R3 and R4, together with the ring atoms to which they are each bonded, form a ring selected from the group of 2,3,5,6,7,8-hexahydro-1,2,3a,4,5,8-hexaaza-cyclopenta[b]naphthalyl; 2,6,7,8-tetrahydro-3H-5-oxa-1,2,3a,4,8-pentaaza-cyclopenta[b]naphthalyl; 2,3,6,7-tetrahydro-5,8-dioxa-1,2,3a,4-tetraaza-cyclopenta[b]naphthalyl; 2,3,6,7-tetrahydro-5H-8-oxa-1,2,3a,4,5-pentaaza-cyclopenta[b]naphthalyl; 2,6,7,8-tetrahydro-3H-5-thia-1,2,3a,4,8-pentaaza-cyclopenta[b]naphthalyl; 2,3,6,7,8,9-hexahydro-1,2,3a,4,6,9-hexaazacyclopenta[a]naphthalyl; 2,3-dihydro-5,7-dioxa-1,2,3a,4-tetraaza-s-indacenyl; 2,6,7,8-tetrahydro-3H-cyclopenta[e][1,2,4]triazolo[4,3-b]pyridazinyl; 2,7,8,9-tetrahydro-3H-cyclopenta[d][1,2,4]triazolo[4,3-b]pyridazinyl and 2,3,6a,9a-tetrahydro-[1,3]dioxolo[4,5-d][1,2,4]triazolo[4,3-b]pyridazinyl, where the ring is unsubstituted or mono- or disubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl,
—(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl,
—(C 0 -C 4 )-alkylene-(C 4 -C 15 )-Het, —SO 2 CH 3 or —SO 2 CF 3 ,
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, selected from the group of azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, azepinyl, morpholinyl, thiomorpholinyl, pyrrolidine-2,5-dionyl, piperidine-2,6-dionyl, piperazine-2,6-dionyl, morpholine-3,5-dionyl, pyrrolidin-2-onyl, piperidin-2-onyl, piperazin-2-onyl and morpholin-3-onyl, where the ring is unsubstituted or mono- or disubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, R8 and R9 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH,
—CN, —NO 2 , —O—(C 1 -C 8 )-alkyl, —O—(C 3 -C 6 )-cycloalkyl,
—SO 2 CH 3 , —SO 2 CF 3 , —(C 0 -C 4 )-alkylene-(CO)—N(R21)-R22,
—(C 0 -C 4 )-alkylene-C(O)—O—R21, halogen, —SF 5 ,
—(C 0 -C 4 )-alkylene-C(O)—R21, —(C 0 -C 4 )-alkylene-N(R21)-R22,
—(C 0 -C 4 )-alkylene-N(R21)-C(O)—R22, —(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl,
—(C 0 -C 6 )-alkylene-O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —Si[C 1 -C 4 )-alkyl] 3 ,
—(C 0 -C 6 )-alkylene-O—(C 1 -C 4 )-alkylene-(C 3 -C 6 )-cycloalkyl,
—(C 0 -C 6 )-alkylene-O—(C 0 -C 6 )-alkylene-(C 6 -C 14 )-aryl or —(C 4 -C 15 )-Het,
where alkyl, alkylene and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl, —(C 6 -C 14 )-aryl where aryl is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen,
—(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl,
—(C 4 -C 15 )-Het where Het is unsubstituted or mono-, di-, tri-, tetra- or pentasubstituted independently by halogen, —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-cycloalkyl, or —O—(C 3 -C 6 )-cycloalkyl,
where some or all of the hydrogen atoms in alkyl, alkylene or cycloalkyl may be replaced by fluorine,
with the proviso that at least one R5, R6, R7, R8 or R9 is not a hydrogen atom, or
R5 and R6, R6 and R7, R7 and R8 or R8 and R9, together with the ring atoms to which they are each bonded, form a 5- to 8-membered ring selected from the group of 2,3-dihydrobenzo[1,4]dioxinyl; 3,4-dihydro-2H-benzo[1,4]oxazinyl; 1,2,3,4-tetrahydroquinoxalinyl; benzo[1,3]dioxol; 3,4-dihydro-2H-benzo[1,4]thiazinyl and 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepinyl,
where the ring is unsubstituted or mono- or disubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl,
—(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl,
—(C 0 -C 4 )-alkylene-(C 4 -C 15 )-Het, —SO 2 CH 3 or —SO 2 CF 3 ,
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(O)—R22” fragments represent a 5- to 8-membered ring selected from the group of azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, azepinyl, morpholinyl, thiomorpholinyl, pyrrolidine-2,5-dionyl, piperidine-2,6-dionyl, piperazine-2,6-dionyl, morpholine-3,5-dionyl, pyrrolidin-2-onyl, piperidin-2-onyl, piperazin-2-onyl and morpholin-3-onyl, where the ring is unsubstituted or mono- or disubstituted independently by —(C 1 -C 4 )-alkyl, —(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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.
4. A compound as claimed in claim 1 , wherein
X is C—R1,
A − is an anion of an organic or inorganic acid,
Q1 is a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl,
—(C 0 -C 4 )-alkylene-C(O)—O—R11, —(C 0 -C 4 )-alkylene-C(O)—N(R11)-R12,
—(C 0 -C 4 )-alkylene-C(O)—R11, —OH, —O—(C 1 -C 6 )-alkyl or
—O—(C 3 -C 6 )-cycloalkyl, where alkyl and cycloalkyl are each unsubstituted or mono-, di- or trisubstituted independently by —(C 1 -C 4 )-alkyl,
—(C 3 -C 6 )-cycloalkyl, OH, —O—(C 1 -C 6 )-alkyl or —O—(C 3 -C 6 )-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, —(C 1 -C 6 )-alkyl or —(C 3 -C 6 )-cycloalkyl, where some or all of the hydrogen atoms in alkyl or cycloalkyl may be replaced by fluorine,
R1, R2, R3 and R4 are the same or different and are each independently a hydrogen atom, —(C 1 -C 4 )-alkyl, —O—(C 1 -C 8 )-alkyl, —O—(C 3 -C 6 )-cycloalkyl, —(C 0 -C 4 )-alkylene-C(O)—N(R11)-R12, —(C 0 -C 4 )-alkylene-C(O)—O—R11, —CF 3 , —(C 0 -C 4 )-alkylene-N(R11)-C(O)—O—R12, —(C 0 -C 4 )-alkylene-N(R11)-R12, chlorine, —O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —O—(C 0 -C 4 )-alkylene-(C 6 -C 14 )-aryl or —(C 4 -C 15 )-Het where Het is selected from the group of acridinyl, azepinyl, azetidinyl, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzothiazolyl, benzotriazolyl, benzisoxazolyl, benzisothiazolyl, carbazolyl, 4aH-carbazolyl, carbolinyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, dibenzofuranyl, dibenzothiophenyl, dihydrofuran[2,3-b]tetrahydrofuranyl, dihydrofuranyl, dioxolyl, dioxanyl, 2H,6H-1,5,2-dithiazinyl, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isobenzofuranyl, isoquinolinyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isothiazolidinyl, 2-isothiazolinyl, isothiazolyl, isoxazolyl, isoxazolidinyl, 2-isoxazolinyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolidinyl, oxazolyl, oxothiolanyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxathiinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyroazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridooxazolyl, pyridoimidazolyl, pyridothiazolyl, pyridothiophenyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrahydropyridinyl, 6H-1,2,5-thiadiazinyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianthrenyl, thiazolidinyl, thiazolinyl, thiazolyl, thienyl, thienoimidazolyl, thienooxazolyl, thienopyrrol, thienopyridin, thienothiazolyl, thienothiophenyl, thiomorpholinyl, triazinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl and xanthenyl,
where alkylene is unsubstituted or monosubstituted by —(C 1 -C 4 )-alkyl or —(C 3 -C 6 )-cycloalkyl, or some or all of the hydrogen atoms in alkylene are replaced by fluorine,
R11 and R12 are each independently a hydrogen atom or —(C 1 -C 6 )-alkyl,
R5, R6, R7, R8 and R9 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-alkyl, OH, —O—(C 1 -C 8 )-alkyl, chlorine, bromine, —SF 5 , —(C 0 -C 4 )-alkylene-N(R21)-R22, —(C 4 -C 15 )-Het, —(C 0 -C 4 )-alkylene-N(R21)—C(O)—R22, —CF 3 —(C 0 -C 6 )-alkylene-O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —(C 0 -C 6 )-alkylene-O—(C 1 -C 4 )-alkylene-(C 3 -C 6 )-cycloalkyl or —(C 0 -C 6 )-alkylene-O—(C 0 -C 6 )-alkylene-(C 6 -C 14 )-aryl,
where alkylene is unsubstituted or monosubstituted by
—O—(C 1 -C 6 )-alkyl,
with the proviso that at least one R5, R6, R7, R8 or R9 is not a hydrogen atom,
R5 and R6, R6 and R7, R7 and R8 or R8 and R9, together with the ring atoms to which they are each bonded, form a morpholine ring, where the ring is unsubstituted or monosubstituted by —(C 1 -C 4 )-alkyl,
R21 and R22 are each independently a hydrogen atom or
—(C 1 -C 6 )-alkyl.
5. A compound as claimed in claim 1 , wherein the compound is a physiologically compatible salt of a compound selected from the group consisting of:
3-amino-1-[2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl]-6-trifluoromethyl-[1,2,4]triazolo[4,3-a]pyridin-1-ium,
3-amino-1-[2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl][1,2,4]triazolo[4,3-a]pyridin-1-ium,
3-amino-1-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-6-trifluoromethyl-[1,2,4]triazolo[4,3-a]pyridin-1-ium,
3-amino-1-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-5-methyl-7-trifluoromethyl-[1,2,4]triazolo[4,3-a]pyridin-1-ium,
3-amino-5-chloro-1-{2-[3-methylamino-5-(pentafluorosulfanyl)phenyl]-2-oxoethyl}-[1,2,4]triazolo[4,3-a]pyridin-1-ium,
3-amino-7-ethoxy-6-ethoxycarbonyl-1-{2-[3-methylamino-5-(pentafluorosulfanyl)phenyl]-2-oxoethyl}-[1,2,4]triazolo[4,3-a]pyridin-1-ium,
3-amino-1-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-7-ethoxy-6-ethoxycarbonyl-[1,2,4]triazolo[4,3-a]pyridin-1-ium,
3-amino-1-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-7-ethoxy-6-methylcarbamoyl-[1,2,4]triazolo[4,3-a]pyridin-1-ium,
3-amino-1-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-6-ethoxy-[1,2,4]triazolo[4,3-a]pyridin-1-ium, and
3-amino-1-[2-(8-tert-butyl-4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-2-oxoethyl]-6-ethoxy-[1,2,4]triazolo[4,3-a]pyridin-1-ium.
6. A pharmaceutical composition comprising at least one compound as claimed in claim 1 and a pharmaceutically acceptable carrier.