NZ759633B2 - New azaquinoline derivatives - Google Patents
New azaquinoline derivatives Download PDFInfo
- Publication number
- NZ759633B2 NZ759633B2 NZ759633A NZ75963318A NZ759633B2 NZ 759633 B2 NZ759633 B2 NZ 759633B2 NZ 759633 A NZ759633 A NZ 759633A NZ 75963318 A NZ75963318 A NZ 75963318A NZ 759633 B2 NZ759633 B2 NZ 759633B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- halogen atoms
- halogenoalkyl
- group
- alkoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract 53
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims abstract 3
- 125000005843 halogen group Chemical group 0.000 claims 259
- -1 -OH Chemical group 0.000 claims 92
- 125000004093 cyano group Chemical group *C#N 0.000 claims 92
- 229910052736 halogen Inorganic materials 0.000 claims 85
- 150000002367 halogens Chemical group 0.000 claims 84
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 72
- 125000001424 substituent group Chemical group 0.000 claims 72
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 67
- 229910052739 hydrogen Inorganic materials 0.000 claims 64
- 239000001257 hydrogen Substances 0.000 claims 64
- 150000002431 hydrogen Chemical group 0.000 claims 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 44
- 229910052731 fluorine Inorganic materials 0.000 claims 37
- 239000011737 fluorine Substances 0.000 claims 37
- 125000001072 heteroaryl group Chemical group 0.000 claims 37
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 30
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 25
- 229910052801 chlorine Inorganic materials 0.000 claims 25
- 239000000460 chlorine Chemical group 0.000 claims 25
- 125000004429 atom Chemical group 0.000 claims 24
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 23
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000002950 monocyclic group Chemical group 0.000 claims 16
- 125000001153 fluoro group Chemical group F* 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000001188 haloalkyl group Chemical group 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 9
- 229910052794 bromium Inorganic materials 0.000 claims 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- 229910018482 SF5 Inorganic materials 0.000 claims 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- WNBQDDAKLKODPH-UHFFFAOYSA-N 1,2,4-triazolidine Chemical compound C1NCNN1 WNBQDDAKLKODPH-UHFFFAOYSA-N 0.000 claims 2
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000000676 alkoxyimino group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 claims 1
- ZROILLPDIUNLSE-UHFFFAOYSA-N 1-phenyl-1h-pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1C1=CC=CC=C1 ZROILLPDIUNLSE-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 1
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical compound C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- SOIDQYXQSTZLHM-UHFFFAOYSA-N 6-oxa-1-azabicyclo[3.1.1]heptane Chemical compound C1N2OC1CCC2 SOIDQYXQSTZLHM-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 101100160255 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) YLR154C-H gene Proteins 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004360 trifluorophenyl group Chemical group 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 208000006968 Helminthiasis Diseases 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/502—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with carbocyclic ring systems, e.g. cinnoline, phthalazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Abstract
The present invention covers azaquinoline compounds of general formula (I), with A being (A1) or (A2), and in which T, R1, R2, R3, R4, R5, R6, and Q are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment, control and/or prevention of diseases, in particular of helminth infections, as a sole agent or in combination with other active ingredients.
Claims (20)
1. A compound of formula (I): wherein: 5 A is T is selected from the group consisting of T1, T2, T3, T4, T5, and T6; T 1 T 2 T 3 T 4 T 5 T 6 R1 is ed from the group consisting of hydrogen or methyl, cyano, -CHO, -OH, alkyl, 10 C1-C4-halogenoalkyl having 1 to 5 halogen atoms, alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, C3-C6-halogenocycloalkyl having 1 to 5 halogen atoms, C3-C4-alkenyl, C3-C4-alkynyl, alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C3-alkyl, cyano- C1-C4-alkyl, -NH-C1-C4-alkyl, -N(C1-C4-alkyl)2, NH2-C1-C4-alkyl-, C1-C4-alkyl-NH-C1-C4- alkyl-, (C1-C4-alkyl)2N-C1-C4-alkyl-, C1-C4-alkyl-C(O)-, C1-C4-halogenoalkyl-C(O)- having 1 to 15 5 halogen atoms, C1-C4-alkoxy-C(O)-, benzyloxy-C(O)-, C1-C4-alkoxy-C1-C4-alkyl-C(O)-, - SO2-C1-C4-alkyl,–SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, phenyl-C1-C4-alkyl, optionally tuted by 1, 2, 3, 4, or 5 substituents independently selected from the group consisting of halogen, -OH, -NO2, cyano, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH2, - C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1- C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and heterocyclyl-C1-C4-alkyl, wherein the cyclyl substituent is selected from the group 5 consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is ally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, -OH, -NO2, cyano, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH2, - NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1- 10 C4-halogenoalkyl having 1 to 5 halogen atoms, -S(O)-C1-C4-halogenoalkyl having 1 to 5 n atoms, and 1-C4-halogenoalkyl having 1 to 5 halogen atoms; R2 is selected from the group consisting of hydrogen, halogen, cyano, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), - C(O)-N(C1-C4-alkyl)2, –NR12R13, –OR14, -SR15, -S(O)R15, -SO2R15, 15 C1-C6-alkyl, C3-C6-cycloalkyl, alkenyl, C3-C6-cycloalkenyl, C2-C4-alkynyl, phenyl-C1-C4- alkyl, each of which is optionally substituted by 1, 2, 3, 4, or 5 tuents independently selected from the group consisting of halogen, -OH, -NO2, cyano, C1-C4-alkyl-C(O)-, C1-C4- alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, -NH2, -NH(C1-C4-alkyl), C4- 20 alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and ered 25 heteroaryl, each of which is optionally tuted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, -OH, -NO2, cyano, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH2, - NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1- C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 30 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, phenyl which is optionally substituted by 1, 2, or 3 tuents independently selected from the group ting of halogen, cyano, nitro, -OH, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6- lkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2- 35 C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and a monocyclic or a bicyclic heterocycle selected from the group consisting of 4- to 10-membered heterocycloalkyl, spirocycloalkyl, ered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, 3, or 4 substituents independently ed from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4-alkoxy-C(O)-, - 5 C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-alkyl-C(O)--, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4- alkoxy-C1-C4-alkyl-, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, - NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 n atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 10 halogen atoms, –SO2-C1-C4-halogenoalkyl having 1 to 5 n atoms, and 4- to 10-membered heterocycloalkyl; R3 is selected from the group consisting of hydrogen, halogen, and C1-C4-alkyl; R4 is selected from the group consisting of hydrogen, halogen, -OH, cyano, C1-C4-alkyl, C3-C6- cycloalkyl, halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy-C1-C4-alkyl, C1-C4- 15 alkoxy, C1-C4-alkyl-C(O)-, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1- C4-alkyl, and -SO2-C1-C4-alkyl; R5 is selected from the group consisting of en, halogen, -OH, cyano, C1-C4-alkyl, C3-C6- cycloalkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy-C1-C4-alkyl, C1-C4- alkoxy, alkyl-C(O)-, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1- 20 C4-alkyl, and -SO2-C1-C4-alkyl; R6 is selected from the group ting of hydrogen, halogen, -OH, cyano, C1-C4-alkyl, C3-C6- lkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy-C1-C4-alkyl, C1-C4- alkoxy, C1-C4-alkyl-C(O)-, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1- C4-alkyl, and 1-C4-alkyl; 25 R12 and R13 are ndently selected from the group consisting of hydrogen, -OH, -NH2, -NH(C1-C4-alkyl), C4-alkyl)2, -NH(-C(O)-C1-C4-alkyl), -N(C1-C4- alkyl)(-C(O)-C1-C4-alkyl), C1-C4-alkoxy, C1-C4-alkoxy-C(O)-, C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, -OH, cyano, - 30 COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, -NHC (O)-C1-C4-alkyl, -N(C1-C4-alkyl)(-C(O)-C1-C4-alkyl), C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and -alkoxy)2P(=O)-, heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and ered 5 heteroaryl, each of which is ally substituted by 1, 2, or 3 tuents independently selected from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4- alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 n atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4- halogenoalkoxy having 1 to 5 n atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- 10 C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4- noalkyl having 1 to 5 halogen atoms, phenyl, benzo-C5-C6-cycloalkyl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, C1-C4-alkyl, C1- 15 C4-halogenoalkyl having 1 to 5 n atoms, C1-C4-alkoxy, halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, – S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and 20 a monocyclic or a bicyclic heterocycle selected from the group of 4- to 10-membered heterocycloalkyl, ered heteroaryl, and 6-membered heteroaryl, each of which is ally tuted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)- NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 25 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, – S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms; 30 R14 is selected from the group consisting of -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of n, -OH, cyano, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4- alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4- 35 halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 n atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group consisting of 4- to 10-membered cycloalkyl, 5-membered aryl, and 6-membered 5 heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4- alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4- noalkyl having 1 to 5 halogen atoms, alkoxy, hydroxy-C1-C4-alkyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- 10 C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, 1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 n atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, phenyl, which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 15 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6- cycloalkyl, -NH2, -C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2- C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and a monocyclic or a bicyclic heterocycle selected from the group consisting of 4- to 10-membered 20 heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents ndently selected from the group consisting of halogen, cyano, nitro, -OH, oxo, , -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)- NH(C1-C4-alkyl), N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4-halogenoalkoxy having 1 to 5 25 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - 1-C4-alkyl, 1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, – S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms; R15 is selected from the group consisting of 30 C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, or 3 substituents ndently selected from the group consisting of halogen, -OH, cyano, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4- alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- 35 C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered 5 heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently ed from the group consisting of n, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4- alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 n atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- 10 C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, phenyl, which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 15 halogen atoms, C1-C4-alkoxy, halogenoalkoxy having 1 to 5 halogen atoms, C3-C6- cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2- C1-C4-alkyl, C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and a monocyclic or a ic heterocycle selected from the group consisting of 4- to bered 20 heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally tuted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4-alkoxy-C(O)-, NH2, -C(O)- NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4-halogenoalkoxy having 1 to 5 25 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, – S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms; Q is ed from the group consisting of 6- or 10-membered aryl, and 5- to 10-membered 30 heteroaryl, each of which is ally substituted by 1, 2, 3, 4, or 5 substituents ed from the group consisting of halogen, SF5, cyano, -CHO, nitro, oxo, C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C1-C4-alkoxy, C3-C6-cycloalkyl-C1- C4-alkoxy, cyano-C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH(C1- C4-alkyl), -N(C1-C4-alkyl)2, -NH-SO2-(C1-C4-alkyl), -N(SO2-[C1-C4-alkyl])(C1-C4-alkyl), (C1- 35 C4-alkoxyimino)-C1-C4-alkyl, 4- to 6-membered heterocyclyl, which is optionally substituted with 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, and cyano, -CH2-O-(C1-C4-alkyl), -CH2-NH(C1-C4-alkyl), -CH2-N(C1-C4-alkyl)2, methyl tuted with a 4- to 6-membered heterocyclyl which itself is optionally substituted with 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, and cyano, -CH2-S-(C1-C4-alkyl), -CH2-S(O)-(C1-C4-alkyl), -CH2-SO2-(C1-C4-alkyl), -S-(C1-C4- 5 alkyl), -S(O)-(C1-C4-alkyl), -SO2-(C1-C4-alkyl), -S-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms, -S(O)-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms, -SO2-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms, -CONH(C1-C4-alkyl), C3-C6-cycloalkyl), -NHCO(C1-C4- alkyl), -NHCO(C3-C6-cycloalkyl), and C1-C4-halogenoalkyl) having 1 to 5 halogen atoms; 10 or a stereoisomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing.
2. The compound according to claim 1, wherein, R1 is selected from the group consisting of hydrogen, cyano, -CHO, -OH, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 15 halogen atoms, C3-C6-cycloalkyl, C3-C6-halogenocycloalkyl having 1 to 5 halogen atoms, C3-C4- alkenyl, C3-C4-alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C3-alkyl, cyano-C1-C4- alkyl, -NH-C1-C4-alkyl, -N(C1-C4-alkyl)2, NH2-C1-C4-alkyl-, C1-C4-alkyl-NH-C1-C4-alkyl-, (C1- yl)2N-C1-C4-alkyl-, C1-C4-alkyl-C(O)-, halogenoalkyl-C(O)- having 1 to 5 halogen atoms, C1-C4-alkoxy-C(O)-, benzyloxy-C(O)-, C1-C4-alkoxy-C1-C4-alkyl-C(O)-, -SO2-C1-C4- 20 alkyl,–SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, phenyl-C1-C4-alkyl, ally substituted by 1, 2, 3, 4, or 5 substituents ndently selected from the group consisting of halogen, -OH, -NO2, cyano, halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH2, - NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, 1-C4-alkyl, –S-C1- 25 C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered aryl, each of which is optionally substituted by 1, 2, or 3 substituents independently 30 selected from the group consisting of halogen, -OH, -NO2, cyano, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH2, - NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, C1-C4-alkyl, 1-C4-alkyl, –S-C1- C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 n atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms; 35 R2 is selected from the group consisting of hydrogen, halogen, cyano, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), - C(O)-N(C1-C4-alkyl)2,–NR12R13, –OR14, -SR15, -S(O)R15, -SO2R15, C1-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C3-C6-cycloalkenyl, alkynyl, phenyl-C1-C4- alkyl, each of which is optionally substituted by 1, 2, 3, 4, or 5 substituents independently 5 selected from the group ting of halogen, -OH, -NO2, cyano, C1-C4-alkyl-C(O)-, C1-C4- alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, alkoxy, -NH2, -NH(C1-C4-alkyl), -N(C1-C4- alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4- 10 noalkyl having 1 to 5 halogen atoms, heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and ered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group ting of halogen, -OH, -NO2, cyano, C1-C4-halogenoalkyl having 1 15 to 5 n atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH2, - C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1- C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, phenyl which is optionally substituted by 1, 2, or 3 substituents independently selected from the 20 group consisting of halogen, cyano, nitro, -OH, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6- lkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, C4-alkyl, -S(O)-C1-C4-alkyl, -SO2- C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-halogenoalkyl having 1 to 5 n atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and 25 a monocyclic or a ic heterocycle selected from the group consisting of 4- to 10-membered heterocycloalkyl, heterospirocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, 3, or 4 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4-alkoxy-C(O)-, - C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-alkyl-C(O)-, C1- 30 C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4- alkoxy-C1-C4-alkyl-, halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, - NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 n atoms,–SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and 4- to 10-membered 35 heterocycloalkyl; R3 is selected from the group consisting of hydrogen, halogen, and C1-C4-alkyl; R4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 n atoms, and C1-C4-alkoxy; R5 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy; 5 R6 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy; R12 and R13 are independently selected from the group consisting of hydrogen, -OH, -NH2, -C4-alkyl), -N(C1-C4-alkyl)2, -NH(-C(O)-C1-C4-alkyl), C1-C4- alkoxy, 10 C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, or 3 substituents ndently ed from the group consisting of halogen, -OH, cyano, - COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), N(C1-C4-alkyl)2, -NHC (O)-C1-C4-alkyl, -N(C1-C4-alkyl)-(-C(O)-C1-C4-alkyl), C1-C4-alkyl, halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, 15 C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, 1-C4-alkyl, C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and (C1-C4-alkoxy)2P(=O)-, heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group 20 consisting of 4- to bered heterocycloalkyl, 5-membered heteroaryl, and ered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4- alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4- 25 halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 n atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 n atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, phenyl, benzo-C5-C6-cycloalkyl, each of which is optionally substituted by 1, 2, or 3 substituents 30 independently selected from the group consisting of halogen, cyano, nitro, -OH, C1-C4-alkyl, C1- C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, C4-halogenoalkyl having 1 to 5 halogen atoms, – S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 35 to 5 halogen atoms, and a monocyclic or a bicyclic heterocycle selected from the group of 4- to 10-membered heterocycloalkyl, ered heteroaryl, and 6-membered heteroaryl, each of which is ally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)- 5 NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, y-C1-C4-alkyl, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - S(O)-C1-C4-alkyl, 1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, – S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 10 to 5 halogen atoms; R14 is selected from the group consisting of -NH2, -C4-alkyl), -N(C1-C4-alkyl)2, C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, -OH, cyano, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4- 15 alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 n atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, 20 heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, or 3 tuents independently ed from the group consisting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4- alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4- 25 halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, 30 phenyl, which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, C1-C4-alkyl, halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6- cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2- C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl 35 having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and a monocyclic or a ic heterocycle selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group ting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)- 5 NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, alkoxy, hydroxy-C1-C4-alkyl, C1-C4-halogenoalkoxy having 1 to 5 n atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - S(O)-C1-C4-alkyl, 1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, – S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 10 to 5 halogen atoms; R15 is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, -OH, cyano, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4- 15 alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- yl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, 1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-halogenoalkyl having 1 to 5 halogen atoms and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, 20 heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of n, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4- -C(O)-, -C(O)-NH2, NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4- 25 halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4- halogenoalkoxy having 1 to 5 n atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1- C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4- halogenoalkyl having 1 to 5 halogen atoms, 30 phenyl, which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, -OH, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6- cycloalkyl, -NH2, -C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2- C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1-C4-halogenoalkyl 35 having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and a monocyclic or a bicyclic heterocycle selected from the group consisting of 4- to bered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group ting of halogen, cyano, nitro, -OH, oxo, thiono, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)- 5 NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4-halogenoalkoxy having 1 to 5 n atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, C4-halogenoalkyl having 1 to 5 halogen atoms, – 1-C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 10 to 5 halogen atoms; Q is a substituted phenyl ring of the a (Q1) wherein: 15 Z1, Z2, Z3, Z4, and Z5 are independently selected from the group consisting of hydrogen, halogen, SF5, cyano, -CHO, nitro, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C1-C4-alkoxy, C3-C6-cycloalkyl-C1-C4-alkoxy, cyano-C1-C4- alkoxy, C1-C4-halogenoalkoxy having 1 to 5 n atoms, -NH(C1-C4-alkyl), -N(C1- C4-alkyl)2, -NH-SO2-(C1-C4-alkyl), -N(SO2-[C1-C4-alkyl])(C1-C4-alkyl), (C1-C4- 20 alkoxyimino)-C1-C4-alkyl, 4- to ered heterocyclyl, which is optionally tuted with 1 or 2 substituents selected from the group consisting of fluorine, chlorine, e, methyl, and cyano, -CH2-O-(C1-C4-alkyl), -CH2-NH(C1-C4-alkyl), - CH2-N(C1-C4-alkyl)2, methyl substituted with a 4- to 6-membered heterocyclyl which itself is optionally substituted with 1 or 2 substituents selected from the group consisting 25 of fluorine, chlorine, bromine, methyl, and cyano, -CH2-S-(C1-C4-alkyl), -CH2-S(O)- (C1-C4-alkyl), -CH2-SO2-(C1-C4-alkyl), -S-(C1-C4-alkyl), -S(O)-(C1-C4-alkyl), -SO2-(C1- C4-alkyl), -S-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms, -S(O)-(C1-C4- halogenoalkyl) having 1 to 5 halogen atoms, -SO2-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms, -CONH(C1-C4-alkyl), -CONH(C3-C6-cycloalkyl), -NHCO(C1-C4-alkyl), 30 -NHCO(C3-C6-cycloalkyl), and C1-C4-halogenoalkyl) having 1 to 5 halogen atoms; or Z1 and Z2 form, together with the carbon atoms that they are connected to, a 5- or 6-membered saturated or partially saturated heterocyclic ring, a ered heteroaryl, or a 6- membered heteroaryl, each of which may be optionally tuted with one or two substituents selected from the group consisting of methyl, fluorine, and oxo; and 5 Z3, Z4, and Z5 are independently selected from the group consisting of hydrogen, halogen, SF5, cyano, CHO, nitro, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C1-C4-alkoxy, C3-C6-cycloalkyl-C1-C4-alkoxy, cyano-C1-C4-alkoxy, C1-C4- alkoxy-C(O)-, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH(C1-C4-alkyl), - N(C1-C4-alkyl)2, -NH-SO2-(C1-C4-alkyl), -N(SO2-[C1-C4-alkyl])(C1-C4-alkyl), (C1-C4- 10 alkoxyimino)-C1-C4-alkyl, 4- to 6-membered cycloalkyl which is optionally substituted with 1 or 2 substituents selected from the group consisting of fluorine, methyl, and cyano, -CH2-O-(C1-C4-alkyl), -CH2-NH(C1-C4-alkyl), -CH2-N(C1-C4- alkyl)2, methyl tuted with a 4- to 6-membered heterocycloalkyl which itself is optionally substituted with 1 or 2 substituents selected from the group consisting of 15 fluorine, methyl, and cyano, -CH2-S-(C1-C4-alkyl), -CH2-S(O)-(C1-C4-alkyl), -CH2-SO2- -alkyl), -S-(C1-C4-alkyl), -S(O)-(C1-C4-alkyl), -SO2-(C1-C4-alkyl), -S-(C1-C4- halogenoalkyl) having 1 to 5 halogen atoms, (C1-C4-halogenoalkyl) having 1 to 5 n atoms, -SO2-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms, -CONH(C1- C4-alkyl), -CONH(C3-C6-cycloalkyl), -NHCO(C1-C4-alkyl), -NHCO(C3-C6-cycloalkyl), 20 and -NHCO(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms; or Z2 and Z3 form, together with the carbon atoms that they are connected to, a 5- or 6-membered saturated or partially saturated heterocyclic ring, a 5-membered heteroaryl, or a 6- membered heteroaryl, each of which may be optionally substituted with one or two substituents selected from the group consisting of methyl, fluorine, and oxo; and 25 Z1, Z4, and Z5 are independently ed from the group consisting of hydrogen, halogen, SF5, cyano, CHO, nitro, C1-C4-alkyl, halogenoalkyl having 1 to 5 halogen atoms, hydroxy, alkoxy, C3-C6-cycloalkyl-C1-C4-alkoxy, cyano-C1-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -NHSO2- (C1-C4-alkyl), -N(SO2-[C1-C4-alkyl])(C1-C4-alkyl), -alkoxyimino)-C1-C4- 30 alkyl, 4- to 6-membered heterocycloalkyl which is optionally substituted with 1 or 2 substituents selected from the group consisting of fluorine, methyl, and cyano, -CH2-O- (C1-C4-alkyl), -CH2-NH(C1-C4-alkyl), -CH2-N(C1-C4-alkyl)2, methyl tuted with a 4- to 6-membered heterocycloalkyl which itself is optionally substituted with 1 or 2 substituents selected from the group consisting of fluorine, methyl, and cyano, -CH2-S- 35 (C1-C4-alkyl), -CH2-S(O)-(C1-C4-alkyl), -CH2-SO2-(C1-C4-alkyl), -S-(C1-C4-alkyl), - S(O)-(C1-C4-alkyl), -SO2-(C1-C4-alkyl), -C4-halogenoalkyl) having 1 to 5 halogen atoms, -S(O)-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms, -SO2-(C1-C4- halogenoalkyl) having 1 to 5 halogen atoms, -CONH(C1-C4-alkyl), -CONH(C3-C6- cycloalkyl), -NHCO(C1-C4-alkyl), -NHCO(C3-C6-cycloalkyl), and -NHCO(C1-C4- halogenoalkyl) having 1 to 5 halogen atoms; or Q is a pyridine ring of the a (Q2) 5 (Q2) wherein: Z6, Z7, Z8, and Z9 are ndently ed from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4- alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH(C1-C4-alkyl), and - 10 N(C1-C4-alkyl)2; or Q is a pyrimidine ring of the formula (Q3) wherein: Z10, Z11, and Z12 are independently selected from the group consisting of hydrogen, halogen, 15 cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1- C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH(C1-C4-alkyl), and C4- alkyl)2; or Q is a pyridine ring of the formula (Q4) 20 wherein: Z13, Z14, Z15, and Z16 are independently selected from the group consisting of hydrogen halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4- alkoxy, C1-C4-halogenoalkoxy having 1 to 5 n atoms, C1-C4-hydroxyalkyl, NH2, - NH(C1-C4-alkyl), C4-alkyl)2, -NH-CO-C1-C4-alkyl, and monocyclic heterocycles 5 selected from the group consisting of 4- to 7-membered heterocycloalkyl, and 5- membered heteroaryls having at least one nitrogen atom via which the heteroaryl ring is connected to the pyridine ring, each of which is optionally substituted with 1, 2, or 3 substituents independently selected from the group consisting of n, cyano, nitro, -OH, oxo, , C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, 10 C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, - NH2, -C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, -SO2-C1- C4-alkyl, -S-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms, (C1-C4- halogenoalkyl) having 1 to 5 halogen atoms, and -SO2-(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms; or 15 Q is a pyridine ring of the formula (Q5) wherein: Z17, Z18, Z19, and Z20 are ndently selected from the group consisting of hydrogen, halogen, cyano, alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4- 20 alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH(C1-C4-alkyl), and - N(C1-C4-alkyl)2; or Q is a 5-membered aromatic heterocycle of the formula (Q6) wherein: 25 G1 – G4 are independently selected from the group consisting of N, O, S, C-Z21, and N-Z22, wherein not more than one of G1 – G4 is O, not more than one of G1 – G4 is S, not more than one of G1 – G4 is N-Z22; and wherein each Z21 is independently selected from the group consisting of hydrogen, halogen, cyano, C1- C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, and C1-C4- halogenoalkoxy having 1 to 5 halogen atoms; and each Z22 is independently selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4- 5 halogenoalkyl having 1 to 5 halogen atoms, alkyl-C3-C6-cycloalkyl, and C1-C4- alkoxy-C1-C4-alkyl; or Q is a 5-membered aromatic heterocycle of the formula (Q7) wherein: 10 U1 – U4 are independently selected from the group consisting of N and C-Z23, wherein not more than three of U1 – U4 are N; and wherein each Z23 is independently selected from the group consisting of hydrogen, halogen, cyano, C1- C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, and C1-C4- halogenoalkoxy having 1 to 5 halogen atoms; 15 or a stereoisomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing.
3. The compound according to claim 1, wherein R1 is selected from the group ting of hydrogen, C1-C4-alkyl, C3-C6-cycloalkyl, C3-C4-alkenyl, alkynyl, C1-C4-alkoxy-C1-C4-alkyl, C3-C6-cycloalkyl-C1-C3-alkyl, and cyano-C1-C4-alkyl; 20 R2 is selected from the group consisting of hydrogen, halogen, cyano, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, NH(C1-C4-alkyl), - (C1-C4-alkyl)2;–NR12R13,–OR14, -SR15, 15, 5, C1-C4-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C3-C6-cycloalkenyl, C2-C4-alkynyl, phenyl-C1-C4- alkyl, each of which is optionally substituted by 1, 2, 3, 4, or 5 substituents independently 25 selected from the group consisting of n, -OH, cyano, C1-C4-alkoxy-C(O)-, -C(O)-NH2, - C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)- C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –S(O)-C1- C4-halogenoalkyl having 1 to 5 halogen atoms, and –SO2-C1-C4-halogenoalkyl having 1 to 5 30 halogen atoms, and a monocyclic or a bicyclic heterocycle selected from the group consisting of 4- to bered heterocycloalkyl, heterospirocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, 3, or 4 substituents independently selected from the group ting of halogen, cyano, -OH, oxo, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, - 5 C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4-alkyl)2, C1-C4-alkyl, C1-C4-alkyl-C(O)-, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, hydroxy-C1-C4-alkyl, C1-C4-alkoxy- C1-C4-alkyl-, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, - NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, and 4- to 10-membered heterocycloalkyl; R3 is selected from the group consisting of hydrogen, halogen, and C1-C4-alkyl; 10 R4 is selected from the group ting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- noalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy; R5 is ed from the group ting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy; R6 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- 15 halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy; R12 and R13 are independently selected from the group consisting of en, (O)-C1-C4-alkyl), C1-C4-alkoxy, C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, -OH, 20 cyano, -COOH, alkoxy-C(O)-, -C(O)-NH2, -C(O)-NH(C1-C4-alkyl), -C(O)-N(C1-C4- alkyl)2, -NH-C(O)-C1-C4-alkyl, -N(C1-C4-alkyl)-(-C(O)-C1-C4-alkyl), C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C3-C6-cycloalkyl, -NH2, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, - S(O)-C1-C4-alkyl, -SO2-C1-C4-alkyl, –S-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, – 25 S(O)-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, –SO2-C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and (C1-C4-alkoxy)2P(=O)-, heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl substituent is ed from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents ndently 30 selected from the group consisting of n, cyano, -OH, oxo, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, , benzo-C5-C6-cycloalkyl, each of which is optionally substituted by 1, 2, or 3 tuents independently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, and a monocyclic or a bicyclic heterocycle selected from the group of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is 5 ally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, -OH, oxo, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1- C4-alkoxy, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms; R14 is selected from the group ting of C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 10 2, or 3 substituents independently selected from the group consisting of halogen, -OH, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, and C3-C6-cycloalkyl, and heterocyclyl-C1-C4-alkyl, wherein the heterocyclyl tuent is ed from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered 15 heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, cyano, -OH, oxo, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, alkoxy, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms; R15 is selected from the group consisting of 20 C1-C4-alkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, -OH, cyano, C1-C4- alkyl, halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, and C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, and heterocyclyl-C1-C4-alkyl, wherein the cyclyl substituent is selected from the group 25 consisting of 4- to 10-membered heterocycloalkyl, ered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents ndently selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, alkoxy, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms; Q is a substituted phenyl ring of the formula (Q1) 30 (Q1) wherein: Z1, Z2, Z3, Z4, and Z5 are independently selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C1-C4-alkoxy, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, -NH(C1-C4- 5 alkyl), -N(C1-C4-alkyl)2, 4- to 6-membered heterocyclyl, which is ally substituted with 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, and cyano, -S-(C1-C4-alkyl), -S(O)-(C1-C4-alkyl), and -SO2-(C1-C4- alkyl); or Z1 and Z2 form, together with the carbon atoms that they are connected to, a 5- or 6-membered 10 heterocycloalkyl, a 5-membered heteroaryl, or a 6-membered heteroaryl, each of which may be optionally substituted with one or two substituents selected from the group consisting of methyl, fluorine, and oxo; and Z3, Z4, and Z5 are independently selected from the group consisting of en, halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4-alkoxy, C1- 15 C4-alkoxy-C(O)-, and halogenoalkoxy having 1 to 5 halogen atoms; or Z2 and Z3 form, together with the carbon atoms that they are connected to, a 5- or 6-membered saturated or partially saturated heterocyclic ring, a 5-membered heteroaryl, or a 6- membered heteroaryl, each of which may be ally substituted with one or two substituents selected from the group consisting of , fluorine, and oxo; and 20 Z1, Z4, and Z5 are independently selected from the group consisting of en, halogen, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 n atoms, C1-C4-alkoxy, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms; or a isomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing. 25 4. The compound according to claim 1, n R is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, and C1-C4-alkoxy; R1 is en or C1-C4-alkyl; R2 is selected from the group consisting of hydrogen, halogen,–NR12R13,–OR14, -SR15, -S(O)R15, - 30 C1-C4-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C3-C6-cycloalkenyl, each of which is ally substituted by 1, 2, 3, 4, or 5 substituents independently selected from the group consisting of halogen, cyano, C1-C4-alkoxy-C(O)-, and -C(O)-NH2, and a monocyclic or a bicyclic heterocycle selected from the group consisting of 4- to 10-membered heterocycloalkyl, heterospirocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, 3, or 4 substituents independently ed from the group consisting of halogen, -OH, oxo, -COOH, C1-C4-alkoxy-C(O)-, NH2, C1-C4- 5 alkyl, C1-C4-alkyl-C(O)-, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C1-C4- alkyl-, C1-C4-alkoxy-C1-C4-alkyl-, -NH2, -N(C1-C4-alkyl)2, and 4- to 10-membered heterocycloalkyl; R3 is selected from the group consisting of hydrogen, halogen, and C1-C4-alkyl; R4 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- 10 halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy; R5 is ed from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy; R6 is selected from the group consisting of hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy; 15 R12 and R13 are ndently selected from the group consisting of hydrogen, -NH(-C(O)-C1-C4-alkyl), C1-C4-alkoxy, C1-C4-alkyl, C3-C6-cycloalkyl, -C1-C4-alkyl, each of which is optionally tuted by 1, 2, or 3 substituents independently selected from the group consisting of halogen, -OH, -COOH, C1-C4-alkoxy-C(O)-, -C(O)-NH2, -C(O)-N(C1-C4-alkyl)2, -NH-C(O)-C1-C4-alkyl, C1-C4-alkyl, 20 C1-C4-alkoxy, C3-C6-cycloalkyl, -NH2, -N(C1-C4-alkyl)2, -S-C1-C4-alkyl, -S(O)-C1-C4-alkyl, - SO2-C1-C4-alkyl, and (C1-C4-alkoxy)2P(=O)-, heterocyclyl-C1-C4-alkyl, wherein the cyclyl tuent is selected from the group consisting of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl, each of which is optionally substituted by 1, 2, or 3 substituents independently 25 selected from the group consisting of halogen, cyano, -OH, oxo, C1-C4-alkyl, C1-C4- halogenoalkyl having 1 to 5 halogen atoms, and C1-C4-alkoxy, phenyl and benzo-C5-C6-cycloalkyl, each of which is optionally substituted by 1, 2, or 3 substituents ndently selected from the group ting of n, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, alkoxy, and C1-C4-halogenoalkoxy 30 having 1 to 5 halogen atoms, and a monocyclic or a ic heterocycle selected from the group of 4- to 10-membered heterocycloalkyl, 5-membered heteroaryl, and 6-membered heteroaryl each of which is optionally substituted by 1, 2, or 3 substituents independently ed from the group consisting of halogen, -OH, oxo, cyano, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1- C4-alkoxy, and C1-C4-halogenoalkoxy having 1 to 5 halogen atoms; R14 is selected from the group consisting of C1-C4-alkyl, C3-C6-cycloalkyl, phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 5 2, or 3 substituents independently selected from the group consisting of halogen, -OH, C1-C4- alkyl, C1-C4-alkoxy, and C3-C6-cycloalkyl, and
4- to 10-membered heterocycloalkyl; R15 is ed from the group consisting of C1-C4-alkyl, which is ally tuted by 1, 2, or 3 substituents independently selected 10 from the group ting of -OH and -COOH, and a 6-membered heteroaryl; Q is a substituted phenyl ring of the formula (Q1) wherein: 15 Z1 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, and C1-C4- alkoxy; Z2 is selected from the group consisting of hydrogen, halogen, -OH, C1-C4-alkyl, C1-C4- alkoxy, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -NH(C3-C6-cycloalkyl), C4- alkyl)(C3-C6-cycloalkyl), C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4- 20 noalkoxy having 1 to 5 halogen atoms, -S-(C1-C4-alkyl), and a 4- to 6-membered heterocycloalkyl; Z3 is ed from the group consisting of hydrogen, halogen, C1-C4-alkyl, C1-C4-alkoxy, - NH(C1-C4-alkyl), and -N(C1-C4-alkyl)2; Z4 is selected from the group consisting of hydrogen, halogen, -OH, C1-C4-alkyl, C1-C4- 25 alkoxy, -NH(C1-C4-alkyl), -N(C1-C4-alkyl)2, -NH(C3-C6-cycloalkyl), -N(C1-C4- alkyl)(C3-C6-cycloalkyl), C1-C4-halogenoalkyl having 1 to 5 halogen atoms, C1-C4- halogenoalkoxy having 1 to 5 halogen atoms, -C4-alkyl), and a 4- to 6-membered heterocycloalkyl; and Z5 is selected from the group ting of en, n, C1-C4-alkyl, and C1-C4- alkoxy; or a stereoisomer, a tautomer, or a salt thereof, or a e of any of the foregoing. 5 5. The compound according to claim 1, wherein R1 is hydrogen or methyl; R2 is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, –NR12R13, –OR14, -SR15, 15, -SO2R15, methyl, ethyl, propyl, isopropyl, cyclopropyl, cyclohexyl, yl, cyclopentenyl, 10 cyclohexenyl, each of which is optionally substituted by 1 or 2 substituents independently selected from the group consisting of cyano, ethoxy-C(O)-, and -C(O)-NH2, and a monocyclic or a bicyclic heterocycle selected from the group consisting of azetidine, pyrrolidine, pyrazolidine, imidazolidine, 1,2,4-triazolidine, piperidine, piperazine, tetrahydropyridine, dihydro-2H-pyrane, ydropyrane, 1,2-oxazolidine, 1,2-oxazine, 15 morpholine, thiomorpholine, 3,4-dihydroisoquinoline, 2,3-dihydro-indole, 1,3-dihydroisoindole , 3,9-dioxaazabicyclo[3.3.1]nonane, 6-oxaazabicyclo[3.1.1]heptane, 8-oxa azabicyclo[3.2.1]octane, imidazole, pyrazole, 1,2,4-triazole, 1,2,3-triazole, 4-oxa azaspiro[2.5]octane, each of which is optionally substituted by 1, 2, 3, or 4 substituents independently selected from the group consisting of fluorine, chlorine, cyano, -OH, 20 oxo, -COOH, y-C(O)-, ethoxy-C(O)-, tert-butoxy-C(O)-, -C(O)-NH2, methyl, methyl- C(O)-, trifluoromethyl, ymethyl-, methoxymethyl-, -NH2, -NMe2, and idine; R3 is hydrogen, chlorine, or ; R4 is selected from the group consisting of hydrogen, fluorine, chlorine, cyano, methyl, methoxy, and trifluoromethyl; 25 R5 is selected from the group consisting of hydrogen, fluorine, chlorine, and methyl; R6 is selected from the group consisting of hydrogen, fluorine, chlorine, methyl, and y; R12 and R13 are independently selected from the group consisting of hydrogen, -NH(-C(O)-methyl), methoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, cyclopropyl, cyclobutyl, benzyl, 1-phenylethyl, 30 each of which is optionally substituted by 1, 2, or 3 substituents independently selected from the group consisting of fluorine, -OH, -COOH, methoxy-C(O)-, ethoxy-C(O)-, utoxy-C(O)-, - C(O)-NH2, -C(O)-NMe2, -NH-C(O)-methyl, methyl, methoxy, cyclopropyl, -NH2, NMe2, S- methyl, S(O)-methyl, SO2-methyl, and (EtO)2P(=O)-, heterocyclyl-methyl, heterocyclyl-ethyl, wherein the heterocyclyl substituent is selected from the group consisting of pyrrolidine, morpholine, pyrazole, 1, 2, 4-oxadiazole, pyridine, each of which is optionally substituted by 1 substituent independently selected from the group consisting of fluorine, chlorine, -OH, oxo, and methyl,
5 phenyl, and a monocyclic or a bicyclic heterocycle ed from the group of oxetane, ne, pyrrolidine, morpholine, tetrahydropyrane, pyridine, and pyrazole, each of which is ally tuted by 1 or 2 substituents independently selected from the group consisting of fluorine, chlorine, -OH, oxo, and methyl; 10 R14 is selected from the group ting of methyl, ethyl, isopropyl, butyl, entyl, benzyl, each of which is optionally substituted by 1 or 2 substituents independently ed from the group consisting of fluorine, -OH, methyl, y, and cyclopentyl, and a monocyclic or a bicyclic heterocycle selected from the group consisting of pyrrolidine and 15 tetrahydropyrane; R15 is selected from the group consisting of methyl and ethyl, each of which is optionally substituted by 1 substituent independently selected from the group consisting of -OH and -COOH, and pyridine; 20 Q is a substituted phenyl ring of the formula (Q1) wherein: Z1 and Z5 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, and methoxy; 25 Z2 and Z4 are independently selected from the group consisting of hydrogen, fluorine, chlorine, -OH, methyl, ethyl, -NHMe, -NMe2, oromethyl, methoxy, trifluoromethoxy, -SMe, and morpholinyl; and Z3 is independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, methoxy, and –NMe2; or a stereoisomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing.
6. The compound according to claim 1, wherein, R1 is hydrogen or methyl; 5 R2 is selected from the group ting of hydrogen, ne, fluorine, bromine, -NH2, - NH(CH3), -N(CH3)2, methoxy, ethoxy, methyl, ethyl, propyl, isopropyl, cyclopropyl, and a monocyclic heterocycle selected from the group consisting of azetidine, pyrrolidine, pyrazolidine, imidazolidine, 1,2,4-triazolidine, piperazine, 1,2-oxazolidine, tetrahydropyrane, morpholine, thiomorpholine, imidazole, pyrazole, and 1,2,3-triazole, each of which is optionally 10 substituted by 1, 2, 3, or 4 substituents independently selected from the group consisting of fluorine, -OH, oxo, -COOH, methoxy-C(O)-, ethoxy-C(O)-, tert-butoxy-C(O)-, NH2, methyl, methyl-C(O)-, trifluoromethyl, hydroxymethyl-, methoxymethyl-, -NH2, -NMe2, and pyrrolidine; R3 is hydrogen; 15 R4 is selected from the group consisting of hydrogen, ne, fluorine, methyl, y, and trifluoromethyl; R5 is selected from the group consisting of en, chlorine, fluorine, and methyl; R6 is selected from the group consisting of hydrogen, ne, methyl, and methoxy; Q is a substituted phenyl ring of the formula (Q1) 20 (Q1) wherein: Z1 and Z5 are independently selected from the group consisting of en, fluorine, chlorine, methyl, and methoxy; Z2 and Z4 are independently selected from the group consisting of hydrogen, fluorine, 25 chlorine, -OH, methyl, ethyl, -NHMe, -NMe2, trifluoromethyl, methoxy, trifluoromethoxy, -SMe, and morpholinyl; and Z3 is independently selected from the group consisting of hydrogen, ne, chlorine, methyl, methoxy, and –NMe2; or a stereoisomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing.
7. The nd according to claim 1, wherein: T is selected from T1 – T6 as defined in claim 1; 5 R1 is hydrogen or methyl; R2 is selected from the group consisting of hydrogen, chlorine, fluorine, bromine, -NH(CH3), - 2, methoxy, ethoxy, methyl, ethyl, propyl, isopropyl, cyclopropyl, and a monocyclic heterocycle selected from the group consisting of tetrahydropyrane, morpholine, and thiomorpholine; 10 R3 is hydrogen; R4 is selected from the group consisting of hydrogen, chlorine, ne, , methoxy, and trifluoromethyl; R5 is selected from the group consisting of hydrogen, chlorine, fluorine, and methyl; R6 is selected from the group consisting of hydrogen, fluorine, methyl, and methoxy; 15 Q is selected from the group consisting of phenyl, trifluorophenyl, trichlorophenyl, 2,3,5-trifluorophenyl, 2,3,5-trichlorophenyl, 2,3,6-trifluorophenyl, 2,3,6-trichlorophenyl, 2,3- difluorophenyl, 2,3-dichlorophenyl, 2,4,5-trifluorophenyl, 2,4,5-trichlorophenyl, 2,4,6- trifluorophenyl, 2,4,6-trichlorophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-fluoro chlorophenyl, 2-chlorofluorophenyl, 2-chlorofluorophenyl, 2-fluorochlorophenyl, 2- 20 chlorofluorophenyl, rofluorophenyl, 2-fluorophenyl, 2-chlorophenyl, 3,4,5- trifluorophenyl, trichlorophenyl, 3,4-difluorophenyl, 3,4-dichlorophenyl, 3,5-difluoro chlorophenyl, 3,5-dichlorofluorophenyl, 3,5-difluorophenyl, chlorophenyl, 3-chloro fluorophenyl, 3-chlorofluorophenyl, 3-fluorophenyl, 3-chlorophenyl, 5-chloro-2,4- difluorophenyl, 5-fluoro-2,4-dichlorophenyl, and 5-chlorofluorophenyl; 25 or a stereoisomer, a tautomer, or a salt f, or a mixture of any of the foregoing.
8. The compound according to claim 1, wherein T is selected from the group consisting of T1, T2, and T3; T1 T 2 T 3 or a stereoisomer, a tautomer, or a salt f, or a mixture of any of the foregoing.
9. The compound according to claim 1, wherein 5 R2 is selected from the group consisting of C3-C6 cycloalkyl and azetidine, optionally substituted with fluorine.
10. The compound according to claim 2, wherein R2 is selected from the group consisting of C3-C6 cycloalkyl and azetidine, optionally substituted 10 with ne.
11. The compound according to claim 3, wherein R2 is ed from the group consisting of C3-C6 cycloalkyl and azetidine, optionally substituted with fluorine.
12. The compound according to claim 4, wherein R2 is selected from the group consisting of C3-C6 lkyl and azetidine, optionally substituted with ne. 20
13. The compound according to claim 8, wherein R2 is selected from the group consisting of C3-C6 cycloalkyl and azetidine, optionally substituted with fluorine.
14. A ceutical composition comprising a compound of formula (I) according to claim 1, or a 25 stereoisomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing, and one or more pharmaceutically acceptable excipients.
15. A pharmaceutical composition comprising a compound of formula (I) according to claim 9, or a isomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing, and one or more pharmaceutically acceptable excipients. 5
16. A pharmaceutical composition comprising a compound of formula (I) according to claim 10, or a stereoisomer, a tautomer, or a salt f, or a mixture of any of the foregoing, and one or more pharmaceutically acceptable excipients.
17. A pharmaceutical composition sing a compound of formula (I) according to claim 11, or a 10 isomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing, and one or more pharmaceutically acceptable excipients.
18. A pharmaceutical composition comprising a compound of formula (I) according to claim 12, or a stereoisomer, a tautomer, or a salt thereof, or a mixture of any of the ing, and one or more 15 pharmaceutically acceptable excipients.
19. A ceutical ition comprising a compound of formula (I) according to claim 13, or a stereoisomer, a tautomer, or a salt thereof, or a mixture of any of the foregoing, and one or more pharmaceutically acceptable excipients.
20. A method of preparing a compound of formula (I) according to claim 1, said method comprising the step of reacting an intermediate compound of formula 1N-T1, 1N-T2, 1N-T3, 1N-T4, 1N-T5, or 1N- 25 1N-T1 1N-T2 1N-T3 1N-T4 1N-T5 1N-T6 wherein A, R1, R3, R4, R5, R6, and Q are as d for the compound of formula (I) according to claim with a compound of formula 1F: 5 R2H wherein R2 is NR12R13, OR14, or SR15, each as defined for the compound of formula (I) ing to claim 1; thereby giving a compound of formula (I): 10 (I) wherein T, A, R1, R2, R3, R4, R5, R6, and Q are as defined for the compound of formula (I) according to claim 1; or the step of reacting an intermediate compound of formula 1M-T1, 1M-T2, 1M-T3, 1M-T4, 1M-T5, 15 or 1M-T6: 1M-T1 1M-T2 1M-T3 1M-T4 1M-T5 1M-T6 20 wherein A, R1, R2, R3, R4, R5 and R6 are as defined for the compound of formula (I) according to claim 1, and wherein Hal is chlorine, bromine or iodine; with a compound of formula 1H: Q-B(OR)2 wherein Q is as defined for the compound of formula (I) ing to claim 1, and each R may be individually H or Me or both R are pinacolate; thereby giving a compound of formula (I): 5 (I) n T, A, R1, R2, R3, R4, R5, R6, and Q are as defined for the compound of formula (I) according to claim 1; or the step of reacting an intermediate compound of formula 1W-T1, 1W-T2, 1W-T3, 1W-T4, 1W-T5, 10 or 1W-T6: 1W-T1 1W-T2 1W-T3 1W-T4 1W-T5 1W-T6 15 wherein Q, R2, R3, R4, R5 and R6 are as defined for the compound of formula (I) according to claim 1; with a nd of formula 1V: wherein R1 and A are as defined for the compound of formula (I) according to claim 1; 20 thereby giving a compound of formula (I): wherein T, A, R1, R2, R3, R4, R5, R6, and Q are as defined for the compound of formula (I) according to claim 1; or the step of reacting an ediate compound of a 1X-T1, 1X-T2, 1X-T3, 1X-T4, 1X-T5, or 5 1X-T6: 1X-T1 1X-T2 1X-T3 1X-T4 1X-T5 1X-T6 10 wherein Q, A, R1, R3, R4, R5 and R6 are as defined for the compound of formula (I) according to claim 1; with a compound of formula 1Y: wherein R2 is C1-C4-alkoxy which is optionally substituted as defined for the nd of formula (I) 15 according to claim 1; thereby giving a compound of formula (I): wherein T, A, R1, R3, R4, R5, R6, and Q are as defined for the compound of formula (I) according to claim 1 and R2 is C1-C4-alkoxy which is optionally substituted as defined for the compound of formula 20 (I) according to claim 1; or the step of reacting an intermediate compound of formula 1N-T1, 1N-T2, 1N-T3, 1N-T4, 1N-T5, or 1N-T6: 1N-T1 1N-T2 1N-T3 1N-T4 1N-T5 1N-T6 wherein A, R1, R3, R4, R5, R6, and Q are as d for the nd of formula (I) according to claim with a compound of a 2A: 10 R2Met-X wherein R2 is C1-C4-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C3-C6-cycloalkenyl, C2-C4-alkynyl, phenyl- C1-C4-alkyl, heterocyclyl-C1-C4-alkyl, phenyl or a monocyclic or bicyclic heterocycle, each of which as defined for the compound of formula (I) according to claim 1, Met is magnesium or zinc, and X is 15 chlorine, bromine or iodine; thereby giving a compound of formula (I): wherein T, A, R1, R3, R4, R5, R6, and Q are as defined for the nd of formula (I) according to 20 claim 1 and R2 is C1-C4-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C3-C6-cycloalkenyl, C2-C4-alkynyl or phenyl-C1-C4-alkyl, each of which is optionally substituted as defined for the compound of formula (I) according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP17179149 | 2017-06-30 | ||
| PCT/EP2018/066776 WO2019002132A1 (en) | 2017-06-30 | 2018-06-22 | New azaquinoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ759633A NZ759633A (en) | 2024-05-31 |
| NZ759633B2 true NZ759633B2 (en) | 2024-09-03 |
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