US 12,435,068 B2 · Anthelmintic compounds

Abstract

The present invention relates to novel compounds of general formula (I): with A being A1 or A2: and in which T, X, Y, Ro, R1, R10 and R11 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 the treatment, control and/or prevention of diseases, in particular of helminth infections, as a sole agent or in combination with other active ingredients.

A compound of formula (I)

wherein:
A is A1 or A2,
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:
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.

57 more elements

Anthelmintic compounds

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Anthelmintic compounds

Life of this patent

Abstract

Claims14