Triazolopyridazines as PAR1 inhibitors, production thereof, and use as medicaments
View Patent ↗The invention relates to novel compounds of formula I where R1, R2, R3, R4, R5, R6, R7, R8, Q1, Q2 and Q3 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 method for the treatment of a disorder associated with thromboses, embolisms, hypercoagulability, fibrotic changes or inflammatory disorders, the method comprising administering to a patient in need thereof an effective dose of a compound
or a stereoisomeric or tautomeric form thereof, or a physiologically compatible salt of any of them, where
Q1 is a hydrogen atom, —(C 1 -C 6 )-alkyl, —(C 3 -C 6 )-cycloalkyl, —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 and R3 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-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, 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 —(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,
R11and 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 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, —(C 0 -C 4 )-alkylene-(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, —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,
R4, R5, R6, R7 and R8 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, —(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 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, or —(C 4 -C 15 )-Het where Het 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,
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
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 —(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 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, —(C 0 -C 4 )-alkylene-(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, —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. The method as claimed in claim 1 , wherein the disorder is myocardial infarction, angina pectoris and other types of acute coronary syndrome, stroke, peripheral vascular disorders, deep vein thrombosis, pulmonary embolism, embolic or thrombotic events caused by cardiac arrhythmias, cardiovascular events such as restenosis following revascularization and angioplasty and similar procedures such as stent implantations and bypass operations or reduction of the risk of thrombosis following surgical procedures such as knee and hip joint operations or procedures leading to contact of blood with foreign surfaces, such as for dialysis patients and patients with indwelling catheters or disseminated intravascular coagulation, sepsis and other intravascular events associated with inflammation, atherosclerosis, diabetes and the metabolic syndrome and the sequelae thereof, tumor growth and tumor metastasis, inflammatory and degenerative articular disorders such as rheumatoid arthritis and arthrosis, impairments of the hemostatic system such as fibrin deposits, fibrotic changes in the lung such as chronic obstructive pulmonary disease, adult respiratory distress syndrome or fibrin deposits in the eye following eye operations or prevention and/or treatment of scarring.
3. The method as claimed in claim 1 , wherein for the compound of formula (I):
Q1, 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 and R3 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-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, or
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 or R3 is not a hydrogen atom 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 —(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, 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 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, —(C 0 -C 4 )-alkylene-(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, —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 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, —(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, —(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 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, or —(C 4 -C 15 )-Het where Het 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,
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, or
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 R4, R5, R6, R7 or R8 is not a hydrogen atom, 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 —(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 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, —(C 0 -C 4 )-alkylene-(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, —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.
4. The method as claimed in claim 1 , wherein for the compound of formula (I):
Q1, 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 and R3 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-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, or
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 or R3 is not a hydrogen atom or
R1 and R2 or R2 and R3, 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]naphthalene; 2,6,7,8-tetrahydro-3H-5-oxa-1,2,3a,4,8-pentaaza-cyclopenta[b]naphthalene; 2,3,6,7-tetrahydro-5,8-dioxa-1,2,3a,4-tetraaza-cyclopenta[b]naphthalene; 2,3,6,7-tetrahydro-5H-8-oxa-1,2,3a,4,5-pentaaza-cyclopenta[b]naphthalene; 2,6,7,8-tetrahydro-3H-5-thia-1,2,3a,4,8-pentaaza-cyclopenta[b]naphthalene; 2,3,6,7,8,9-hexahydro-1,2,3a,4,6,9-hexaazacyclopenta[α]naphthalene; 2,3-dihydro-5,7-dioxa-1,2,3a,4-tetraaza-s-indacene; 2,6,7,8-tetrahydro-3H-cyclopenta[e][1,2,4]triazolo[4,3-b]pyridazine; 2,7,8,9-tetrahydro-3H-cyclopenta[d][1,2,4]triazolo[4,3-b]pyridazine and 2,3,6a,9a-tetrahydro-[1,3]dioxolo[4,5-d][1,2,4]triazolo[4,3-b]pyridazine, 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 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 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, —(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, —(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, or
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 R4, R5, R6, R7 or R8 is not a hydrogen atom, 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 selected from the group of 2,3-dihydrobenzo[1,4]dioxin; 3,4-dihydro-2H-benzo[1,4]oxazine; 1,2,3,4-tetrahydroquinoxaline; benzo[1,3]dioxole; 3,4-dihydro-2H-benzo[1,4]thiazine and 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine,
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 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 alkyl or cycloalkyl may be replaced by fluorine.
5. The method as claimed in claim 1 , wherein for the compound of formula (I):
Q1, Q2 and Q3 are the same and are each a hydrogen atom,
R1, R2 and R3 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-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-N(R11)-R12, halogen, —O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl, —O—(C 0 -C 4 )-alkylenephenyl or —O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkylene-O—(C 1 -C 6 )-alkyl,
where alkyl or alkylene is in each case unsubstituted or mono- or disubstituted by —O—(C 1 -C 6 )-alkyl,
where some or all of the hydrogen atoms in alkyl or alkylene may be replaced by fluorine,
with the proviso that at least one R1, R2 or R3 is not a hydrogen atom,
R11 and R12 are each independently a hydrogen atom or —(C 1 -C 6 )-alkyl, or R11 and R12 in the “N(R11)-R12” fragment is a 5- to 8-membered ring selected from the group of azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, azepinyl, imidazolyl, 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,
R4, R5, R6, R7 and R8 are the same or different and are each independently a hydrogen atom, —(C 1 -C 6 )-alkyl, OH, —O—(C 1 -C 8 )-alkyl, halogen, —SF 5 , —(C 0 -C 4 )-alkylene-N(R21)-R22, —(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 )-alkylenephenyl,
where alkyl or alkylene is in each case unsubstituted or mono- or disubstituted by —O—(C 1 -C 6 )-alkyl,
with the proviso that at least one R4, R5, R6, R7 or R8 is not a hydrogen atom, or
R4 and R5, R5 and R6, R6 or R7 or R7 and R8, together with the ring atoms to which they are each bonded, form a five- to eight-membered ring selected from the group of 2,3-dihydrobenzo[1,4]dioxin; 3,4-dihydro-2H-benzo[1,4]oxazine; 1,2,3,4-tetrahydro-quinoxaline; benzo[1,3]dioxole; 3,4-dihydro-2H-benzo[1,4]thiazine and 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine,
where the ring is unsubstituted or mono- or disubstituted by —(C 1 -C 4 )-alkyl,
R21 and R22 are each independently a hydrogen atom or —(C 1 -C 6 )-alkyl, or
R21 and R22 in the “N(R21)-R22” fragment represent a 5- to 8-membered ring selected from the group of azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, azepinyl, imidazolyl, 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.
6. The method as claimed in claim 1 , wherein the compound is selected from:
2-(6-chloro-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-isopropoxy-[1,2,4]triazolo[4,3-b]-pyridazin-2-yl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-methoxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
2-(6-ethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-(4-methoxy-3-morpholin-4-yl-5-trifluoro-methylphenyl)ethanone,
N-[3-[2-(6-ethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)acetyl]-5-(pentafluorosulfanyl)phenyl]-N-methylacetamide,
N-[3-[2-(6-ethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)acetyl]-5-(pentafluorosulfanyl)phenyl]acetamide,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-ethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclopentyloxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclobutoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-phenoxy-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
2-(6-benzyloxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclohexyloxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-[3-imino-6-(2,2,2-trifluoroethoxy)-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-cyclopropylmethoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]-1-[3-methylamino-5-(pentafluorosulfanyl)phenyl]ethanone,
2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]-1-[3-methoxy-5-(pentafluorosulfanyl)phenyl]ethanone,
1-(3-tert-butyl-5-ethoxymethylphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-cyclopropylmethoxymethylphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-4,5-diethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-ethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-propoxymethylphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-4,5-bis(cyclopropylmethoxy)phenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]-1-(3-methoxy-5-trifluoromethylphenyl)ethanone,
1-(3-tert-butyl-5-methoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-cyclopropylmethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-cyclobutyl-methoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-benzyloxymethyl-5-tert-butylphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-cyclo-hexylmethoxy-4,5-dimethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
2-(6-butoxy-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-(3-tert-butyl-5-methoxymethylphenyl)ethanone,
1-(3-chloro-5-methoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(8-tert-butyl-4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-piperidin-1-yl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-diethylamino-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]-1-(3-isopropyl-5-methoxyphenyl)ethanone,
1-(3-cyclohexylmethoxy-5-ethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-bromo-5-methoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-[3-(3,3-dimethylbutoxy)-5-methoxyphenyl]-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-[3-(3,3-dimethylbutoxy)-5-ethoxyphenyl]-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-cyclohexylmethoxy-5-methoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-bromo-4,5-dimethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
2-(6-diethylamino-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-[3-methoxy-5-(pentafluorosulfanyl)phenyl]ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(3-imino-6-morpholin-4-yl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-chloro-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-imidazol-1-yl-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-(5-bromo-2,3-dimethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-methoxyphenyl)-2-{3-imino-6-[2-(2-methoxyethoxy)ethoxy]-[1,2,4]triazolo[4,3-b]pyridazin-2-yl}ethanone,
1-(3-chloro-4,5-dimethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-diethylamino-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-[3-tert-butyl-5-(2-methoxyethoxy)phenyl]-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-methoxyphenyl)-2-[3-imino-6-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-methoxymethylphenyl)-2-[3-imino-6-(2-methoxyethoxy)-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]-1-[3-morpholin-4-yl-5-(pentafluorosulfanyl)phenyl]ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-ethoxy-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
2-[6-(1-ethylpropoxy)-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]-1-(5-methoxy-3-pentafluorosulfanylphenyl)ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-chloro-3-imino-[1,2,4]triazolo[4,3-b]-pyridazin-2-yl)ethanone,
1-[3-tert-butyl-5-(2-methoxyethoxymethyl)phenyl]-2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]-1-[3-(2-methoxyethoxy)-5-(pentafluorosulfanyl)phenyl]ethanone,
2-(6-ethoxy-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-[3-methoxy-5-(pentafluorosulfanyl)phenyl]ethanone,
2-[6-(1-ethylpropoxy)-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]-1-[3-(3-methoxypropoxy)-5-(pentafluorosulfanyl)phenyl]ethanone,
N,N-diethyl-2-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-6-chloro-3-imino-2,3-dihydro-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxamide,
N,N-diethyl-6-chloro-3-imino-2-{2-[3-methoxy-5-(pentafluorosulfanyl)phenyl]-2-oxoethyl}-2,3-dihydro-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxamide,
2-(6-ethyl-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-[3-methoxy-5-(pentafluorosulfanyl)phenyl]ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-ethyl-3-imino-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
1-[3-tert-butyl-5-(3-methoxypropoxy)phenyl]-2-[6-(1-ethylpropoxy)-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-[3-tert-butyl-5-(2-methoxyethoxy)phenyl]-2-[6-(1-ethylpropoxy)-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-cyclopropylmethoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-(3-tert-butyl-5-methoxyphenyl)-2-[6-(1-ethylpropoxy)-3-imino-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
1-[3-tert-butyl-5-(3-methoxypropoxy)phenyl]-2-[6-(1-ethylpropoxy)-3-imino-7-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone,
2-(6-chloro-3-imino-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)-1-[3-methoxy-5-(pentafluorosulfanyl)phenyl]ethanone,
1-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-(6-chloro-3-imino-7,8-dimethyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone,
N,N-diethyl-6-chloro-3-imino-2-{2-[3-methoxy-5-(pentafluorosulfanyl)-phenyl]-2-oxoethyl}-2,3-dihydro-[1,2,4]triazolo[4,3-b]pyridazine-7-carboxamide, N,N-diethyl-2-[2-(3-tert-butyl-4-methoxy-5-morpholin-4-ylphenyl)-2-oxoethyl]-6-chloro-3-imino-2,3-dihydro-[1,2,4]triazolo[4,3-b]pyridazine-7-carboxamide,
1-[3-tert-butyl-5-(3-methoxypropoxy)phenyl]-2-(6-ethoxy-3-imino-7-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl)ethanone, and
1-[3-tert-butyl-5-(2-methoxyethoxy)phenyl]-2-[6-(1-ethylpropoxy)-3-imino-7-methyl-[1,2,4]triazolo[4,3-b]pyridazin-2-yl]ethanone.
7. The method as claimed in claim 1 , wherein the disorder is a disorder associated with thrombosis.
8. The method as claimed in claim 1 , wherein the disorder is myocardial infarction.