US 12,435,068 B2
Anthelmintic compounds
Nils Griebenow, Dormagen (DE); Walter Huebsch, Wuppertal (DE); Hans-Georg Schwarz, Dorsten (DE); Wei Zhuang, Monheim am Rhein (DE); Bernd ALig, Koenigswinter (DE); Adeline Koehler, Langenfeld (DE); Daniel Kulke, Leverkusen (DE); Iring Heisler, Duesseldorf (DE); and Thomas Ilg, Monheim (DE)
Assigned to Elanco Animal Health GmbH, Monheim am Rhein (DE)
Appl. No. 17/287,548
Filed by Elanco Animal Health GmBh, Monheim am Rhein (DE)
PCT Filed Oct. 23, 2019, PCT No. PCT/EP2019/078835
§ 371(c)(1), (2) Date Apr. 22, 2021,
PCT Pub. No. WO2020/083971, PCT Pub. Date Apr. 30, 2020.
Claims priority of application No. 18202419 (EP), filed on Oct. 24, 2018.
Prior Publication US 2021/0380566 A1, Dec. 9, 2021
Int. Cl. C07D 405/14 (2006.01); A61P 33/10 (2006.01); C07D 241/42 (2006.01); C07D 249/18 (2006.01); C07D 311/58 (2006.01); C07D 311/68 (2006.01); C07D 405/12 (2006.01); C07D 409/12 (2006.01); C07D 471/04 (2006.01); C07D 495/04 (2006.01)
CPC C07D 405/14 (2013.01) [A61P 33/10 (2018.01); C07D 241/42 (2013.01); C07D 249/18 (2013.01); C07D 311/58 (2013.01); C07D 311/68 (2013.01); C07D 405/12 (2013.01); C07D 409/12 (2013.01); C07D 471/04 (2013.01); C07D 495/04 (2013.01)] 14 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein:
A is A1 or A2,

OG Complex Work Unit Chemistry
o is 0, 1, 2, 3 or 4;
R is selected from the group consisting of hydrogen, 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, —S—C1-C4-halogenoalkyl, —S(O)—C1-C4-halogenoalkyl and —SO2—C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
X, Y are independently selected from the group consisting of CR7R8, O, S, and N—R9, wherein at least one of X and Y is CR7R8,
or
X, Y form together a ring member selected from the group consisting of —C(O)—O—, —C(O)—NR9—, —S(O)—NR9—, —SO2—NR9— and —SO2—O—;
T is selected from the group consisting of T1, T2, T3, T4, T5, T6, T7, T8a, and T8b:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
L is selected from the group consisting of O and NR9;
M is selected from the group consisting of C═O and CR7R8;
U is selected from the group consisting of CR7 and N;
V is selected from the group consisting of CR7 and N;
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 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-C4-alkyl)2N—C1-C4-alkyl-, C1-C4-alkyl-C(O)—, C1-C4-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-alkyl, and —SO2—C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
phenyl-C1-C4-alkyl, optionally substituted 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, —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;
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 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 halogen atoms and —SO2—C1-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;
C1-C6-alkyl, C3-C6-cycloalkyl, C2-C4-alkenyl, C3-C6-cycloalkenyl, C2-C4-alkynyl or phenyl-C1-C4-alkyl, each of which is optionally substituted by 1, 2, 3, 4 or 5 substituents 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), —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;
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 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 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 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 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, 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-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 halogen atoms, —S(O)—C1-C4-halogenoalkyl having 1 to 5 halogen atoms, —SO2—C1-C4-halogenoalkyl having 1 to 5 halogen atoms, and 4- to 10-membered heterocycloalkyl;
R3 is selected from the group consisting of hydrogen, halogen or C1-C4-alkyl;
R4 is selected from the group consisting of hydrogen, 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, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C1-C4-alkyl-C(O)—, —NH2, —NH(C1-C4-alkyl), —N(C1-C4-alkyl)2, —S—C1-C4-alkyl, —S—C1-C4-halogenoalkyl having 1 to 5 halogen atoms —S(O)—C1-C4-alkyl, —SO2—C1-C4-alkyl;
R5 is selected from the group consisting of hydrogen, 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, C1-C4-alkyl-C(O)—, —NH2, —NH(C1-C4-alkyl), —N(C1-C4-alkyl)2, —S—C1-C4-alkyl, —S(O)—C1-C4-alkyl, —SO2—C1-C4-alkyl;
R6 is selected from the group consisting of hydrogen, 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, C1-C4-halogenoalkoxy having 1 to 5 halogen atoms, C1-C4-alkyl-C(O)—, —NH2, —NH(C1-C4-alkyl), —N(C1-C4-alkyl)2, —S—C1-C4-alkyl, —S—C1-C4-halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C1-C4-alkyl, —SO2—C1-C4-alkyl;
R7 is selected from the group consisting of hydrogen, —OH, halogen, C1-C4-alkyl and C1-C4-alkoxy;
R8 is selected from the group consisting of hydrogen, —OH, halogen, C1-C4-alkyl and C1-C4-alkoxy;
or R7 and R8 form, together with the carbon atom to which they are attached, a 3- to 6-membered ring selected from the group consisting of C3-C6-cycloalkyl and 3- to 6-membered heterocycloalkyl;
R9 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms and C1-C4-alkoxy;
R10 is selected from the group consisting of hydrogen, —OH, C1-C4-alkyl and C1-C4-alkoxy;
R11 is selected from the group consisting of hydrogen, C1-C4-alkyl and C1-C4-alkoxy;
or R10 and R11 form, together with the carbon atom to which they are attached, a 3- to 6-membered ring selected from the group consisting of C3-C6-cycloalkyl and 3- to 6-membered heterocycloalkyl,
R12 and R13 are independently selected from the group consisting of hydrogen, —OH, —NH2, —NH(C1-C4-alkyl), —N(C1-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, —COOH, C1-C4-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, —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 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 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-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;
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-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 halogen atoms and —SO2—C1-C4-halogenoalkyl having 1 to 5 halogen atoms;
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 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-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,
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 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-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 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-alky)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 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;
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, —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
a monocyclic or a bicyclic 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 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-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,
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-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 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 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-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;
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, —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
a monocyclic or a bicyclic 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 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-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,
R16 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms and C1-C4-alkoxy;
R17 is selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms and C1-C4-alkoxy;
Q is selected from the group consisting of 6- to 10-membered aryl and 5- to 10-membered heteroaryl, each of which is substituted by 1, 2, 3, 4 or 5 substituents selected from the group consisting of halogen, SFs, cyano, —CHO, oxo, C1-C4-alkyl, C1-C4-hydroxyalkyl, C1-C4-halogenoalkyl having 1 to 5 halogen atoms, —OH, 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_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 substituted 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-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), —NHCO(C3-C6-cycloalkyl), —NHCO(C1-C4-halogenoalkyl) having 1 to 5 halogen atoms;
wherein when Y is O, S or N—R9, none of R7, R8, R10 and R11 is —OH, and wherein
when X is O, S or N—R9, none of R7 and R8 is —OH;
and/or a stereoisomer, tautomer, N-oxide, hydrate, solvate, and/or a salt thereof,
and/or a mixture thereof.