IP Library › Granted Patent US 12,391,682

Granted Patent B2

US 12,391,682 · App. 17/630,742 · Granted Aug 19, 2025

Isoquinoline derivatives and their use for the treatment of parasitic infections

Inventors: Bernd Alig (Koenigswinter, DE); Walter Huebsch (Wuppertal, DE); Nils Griebenow (Dormagen, DE); Hans-Georg Schwarz (Dorsten, DE); Wei Zhuang (Monheim am Rhein, DE); Daniel Kulke (Leverkusen, DE); Claudia Boehm (Hannover, DE); Iring Heisler (Duesseldorf, DE); Isa Jana Irina Janssen (Wiesbaden, DE); Kirsten Boerngen (Cologne, DE)

Assignee: Elanco Animal Health GmbH

C07D413/14 C07D405/12

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Quick Facts

Patent No.: US 12,391,682
App. No.: 17/630,742
Granted: Aug 19, 2025
Kind: B2

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Abstract

The present invention covers new isoquinoline compounds of general formula (I): in which A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and Q are as defined herein, methods of preparing the compounds, intermediate compounds useful for preparing the compounds of formula (I), pharmaceutical compositions and combinations comprising the compounds of formula (I) and the use of the compounds of formula (D) 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 (360)

1. A compound of formula (I):

in which:

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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 -C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl, —S(O)—C 1 -C 4 -halogenoalkyl and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R p is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

X, Y are independently selected from the group consisting of C 7 R 8 , O, S, and N-R 9 , wherein at least one of X and Y is CR 7 R 8 , or

X, Y form together a ring member selected from the group consisting of —C(O)—O—, —C(O)—NR 9 —, —S(O)—NR 9 —, —SO 2 —NR 9 — and —SO 2 —O—,

R 1 is selected from the group consisting of hydrogen, cyano, —CHO, —OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogenocycloalkyl having 1 to 5 halogen atoms, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl, cyano-C 1 -C 4 -alkyl, —NH—C 1 -C 4 -alkyl, —N(C 1 -C 4 -alkyl) 2 , NH 2 -C 1 -C 4 -alkyl-, C 1 -C 4 -alkyl-NH—C 1 -C 4 -alkyl-, (C 1 -C 4 -alkyl) 2 N—C 1 -C 4 -alkyl-, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -halogenoalkyl-C(O)— having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C(O)—, benzyloxy-C(O)—, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-C(O)—, —SO 2 —C 1 -C 4 -alkyl, and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

phenyl-C 1 -C 4 -alkyl, optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, —OH, —NO 2 , cyano, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms; and

heterocyclyl-C 1 -C 4 -alkyl, wherein the heterocyclyl substituent of the heterocyclyl-C 1 -C 4 -alkyl 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, —NO 2 , cyano, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R 2 is selected from the group consisting of

hydrogen, halogen, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 ;

—NR 12 R 13 ;

—OR 14 ;

—SR 15 , —S(O)R 15 , —SO 2 R 15 ;

C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkenyl, C 2 -C 4 -alkynyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, —OH, —NO 2 , cyano, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH(C(O)—C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl)(C(O)—C 1 -C 4 -alkyl), —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

heterocyclyl-C 1 -C 4 -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, —NO 2 , cyano, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 -C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, and 4- to 10-membered heterocycloalkyl,

R 3 is hydrogen or C 1 -C 4 -alkyl,

R 4 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -alkyl-C(O)—, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, and —SO 2 —C 1 -C 4 -alkyl,

R 5 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -alkyl-C(O)—, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, and —SO 2 —C 1 -C 4 -alkyl,

R 6 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -alkyl-C(O)—, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, and —SO 2 —C 1 -C 4 -alkyl,

R 7 is selected from the group consisting of hydrogen, —OH, fluorine, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 8 is selected from the group consisting of hydrogen, —OH, fluorine, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

or R 7 and R 8 together form an oxo group (═O),

or R 7 and R 8 form, together with the carbon atom to which they are attached, a 3- to 6-membered ring selected from the group consisting of C 3 -C 6 -cycloalkyl and 3- to 6-membered heterocycloalkyl,

R 9 is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and C 1 -C 4 -alkoxy,

R 10 is selected from the group consisting of hydrogen, —OH, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 11 is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

or R 10 and R 11 form, together with the carbon atom to which they are attached, a 3- to 6-membered ring selected from the group consisting of C 3 -C 6 -cycloalkyl and 3- to 6-membered heterocycloalkyl,

R 12 and R 13 are independently selected from the group consisting of

hydrogen, —OH, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH(—C(O)—C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl)(-C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C(O)—;

C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , —NH—C(O)—C 1 -C 4 -alkyl, —N(C 1 -C 4 -alkyl)(-C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and (C 1 -C 4 -alkoxy) 2 P(═O)—;

heterocyclyl-C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

phenyl, benzo-C 5 -C 6 -cycloalkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, —OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl 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 optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, —OH, oxo, thiono, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 -C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R 14 is selected from the group consisting of

—NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 ;

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

heterocyclyl-C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 -C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 -C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R 15 is selected from the group consisting of

hydrogen;

heterocyclyl-C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

Q is selected from the group consisting of 6- or 10-membered aryl and 5- to 10-membered heteroaryl, each of which is optionally substituted by 1, 2, 3, 4 or 5 substituents selected from the group consisting of halogen, SF 5 , cyano, —CHO, nitro, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkoxy, cyano-C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH—SO 2 —(C 1 -C 4 -alkyl), —N(SO 2 —[C 1 -C 4 -alkyl])(C 1 -C 4 -alkyl), (C 1 -C 4 -alkoxyimino)-C 1 -C 4 -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, —CH 2 —O—(C 1 -C 4 -alkyl), —CH 2 —NH(C 1 -C 4 -alkyl), —CH 2 —N(C 1 -C 4 -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, —CH 2 —S—(C 1 -C 4 -alkyl), —CH 2 —S(O)—(C 1 -C 4 -alkyl), —CH 2 —SO 2 —(C 1 -C 4 -alkyl), —S—(C 1 -C 4 -alkyl), —S(O)—(C 1 -C 4 -alkyl), —SO 2 —(C 1 -C 4 -alkyl), —S—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —S(O)—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —SO 2 —(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —CONH(C 1 -C 4 -alkyl), —CONH(C 3 -C 6 -cycloalkyl), —NHCO(C 1 -C 4 -alkyl), —NHCO(C 3 -C 6 -cycloalkyl), —NHCO(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms,

wherein when Y is O, S or N—R 9 , none of R 7 , R 8 , R 10 and R 11 is —OH or C 1 -C 4 -alkoxy, and wherein when X is O, S or N—R 9 , none of R 7 and R 8 is —OH or C 1 -C 4 -alkoxy;

or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

2. The compound of claim 1 , wherein:

A is A1 or A2,

o is 0, 1, 2, 3 or 4,

R p is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

X, Y are independently selected from the group consisting of C 7 R 8 , O, S, and N-R 9 , wherein at least one of X and Y is CR 7 R 8 , or

X, Y form together a ring member selected from the group consisting of —C(O)—O—, —C(O)—NR 9 —, —S(O)—NR 9 —, —SO 2 —NR 9 — and —SO 2 —O—,

R 2 is selected from the group consisting of

hydrogen, halogen, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 ;

—NR 12 R 13 ;

—OR 14 ;

—SR 15 , —S(O)R 15 , —SO 2 R 15 ;

heterocyclyl-C 1 -C 4 -alkyl, wherein the heterocyclyl substituent of the heterocyclyl-C 1 -C 4 -alkyl 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, —NO 2 , cyano, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 -C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and 4- to 10-membered heterocycloalkyl,

R 3 is hydrogen, or C 1 -C 4 -alkyl,

R 4 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), and —N(C 1 -C 4 -alkyl) 2 ,

R 5 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), and —N(C 1 -C 4 -alkyl) 2 ,

R 6 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), and —N(C 1 -C 4 -alkyl) 2 ,

R 7 is selected from the group consisting of hydrogen, —OH, fluorine, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 8 is selected from the group consisting of hydrogen, —OH, fluorine, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

or R 7 and R 8 together form an oxo group (═O),

R 9 is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and C 1 -C 4 -alkoxy,

R 10 is selected from the group consisting of hydrogen, —OH, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 11 is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 12 and R 13 are independently selected from the group consisting of

hydrogen, —OH, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH(—C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkoxy;

C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , —NH—C(O)—C 1 -C 4 -alkyl, —N(C 1 -C 4 -alkyl)-(—C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and (C 1 -C 4 -alkoxy) 2 P(═O)-;

heterocyclyl-C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 4 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

phenyl, benzo-C 5 -C 8 -cycloalkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, —OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, Ca-Co-cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R 14 is selected from the group consisting of

—NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 ;

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), -N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

heterocyclyl-C 1 -C 4 -alkyl, wherein the heterocyclyl substitutent 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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C-C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C)—C 4 -alkyl) 2 , —S-C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R 15 is selected from the group consisting of

hydrogen;

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, ˜C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

heterocyclyl-C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)-, —C(O)-NH 2 , C(O)-NH(C 1 -C 4 -alkyl), —C(O)-N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

Q is a substituted phenyl ring of formula (Q1)

in which:

Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are independently selected from the group consisting of hydrogen, halogen, SF 5 , cyano, —CHO, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkoxy, cyano-C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH—SO 2 —(C 1 -C 4 -alkyl), —N(SO 2 -[C 1 -C 4 -alkyl])(C 1 -C 4 -alkyl), (C 1 -C 4 -alkoxyimino)-C 1 -C 4 -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, —CH 2 —O—(C 1 -C 4 -alkyl), —CH 2 —NH(C 1 -C 4 -alkyl), —CH 2 -N(C 1 -C 4 -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, —CH 2 —S—(C 1 -C 4 -alkyl), —CH 2 —S(O)—(C 1 -C 4 -alkyl), —CH 2 —SO 2 —(C 1 -C 4 -alkyl), —S—(C 1 -C 4 -alkyl), —S(O)—(C 1 -C 4 -alkyl), —SO 2 —(C 1 -C 4 -alkyl), —S 2 —(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —S(O)—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —SO 2 —(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —CONH(C 1 -C 4 -alkyl), —CONH(C 3 -C 6 -cycloalkyl), —NHCO(C 1 -C 4 -alkyl), —NHCO(C 3 -C 6 -cycloalkyl), and NHCO(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, or

Z 2 and Z 4 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

Z 3 , Z 4 , and Z 5 are independently selected from the group consisting of hydrogen, halogen, SF 5 , cyano, CHO, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkoxy, cyano-C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C(O)—, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH—SO 2 —(C 1 -C 4 -alkyl), —N(SO 2 —[C 1 -C 4 alkyl]) (C 1 -C 4 -alkyl), (C 1 -C 4 -alkoxyimino)-C 1 -C 4 -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, —CH 2 —O-(C 1 -C 4 -alkyl), —CH 2 —NH(C 1 -C 4 -alkyl), —CH 2 —N(C 1 -C 4 -alkyl) 2 , methyl substituted 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, ˜CH 2 —S—(C 1 -C 4 -alkyl), —CH 2 —S(O)—(C 1 -C 4 -alkyl), —CH 2 —SO 2 —(C 1 -C 4 -alkyl), —S—(C 1 -C 4 -alkyl), —S(O)—(C 1 -C 4 -alkyl), —SO 2 —(C 1 -C 4 -alkyl), —S—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —S(O)—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —SO 2 —(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —CONH(C 1 -C 4 -alkyl), —CONH(C 1 -C 4 -cycloalkyl), —NHCO(C 1 -C 4 -alkyl), —NHCO(C 3 -C 6 -cycloalkyl), and —NHCO(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, or

Z 2 and Z 3 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

Z 1 , Z 4 , and Z 5 are independently selected from the group consisting of hydrogen, halogen, SF 5 , cyano, CHO, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkoxy, cyano-C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH—SO 2 —(C 1 -C 4 -alkyl), —N(SO 2 -[C 1 -C 4 -alkyl]) (C 1 -C 4 -alkyl), (C 1 -C 4 -alkoxyimino)-C 1 -C 4 -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, —CH 2 -O-(C 1 -C 4 -alkyl), —CH 2 —NH(C 1 -C 4 -alkyl), —CH 2 -N(C 1 -C 4 -alkyl) 2 , methyl substituted 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, —CH 2 —S—(C 1 -C 4 -alkyl), —CH 2 —S(O)—(C 1 -C 4 -alkyl), —CH 2 —SO 2 —(C 1 -C 4 -alkyl), —S-(C 1 -C 4 -alkyl), —S(O)—(C 1 -C 4 -alkyl), —SO 2 —(C 1 -C 4 -alkyl), —S—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —S(O)—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —SO 2 —(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —CONH(C 1 -C 4 -alkyl), —CONH(C 3 -C 6 -cycloalkyl), —NHCO(C 1 -C 4 -alkyl), —NHCO(C 3 -C 6 -cycloalkyl), halogenoalkyl) having 1 to 5 halogen atoms, or

Q is a pyridine ring of formula (Q2)

in which:

Z 6 , Z 7 , Z 8 and Z 9 are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, and —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , or

Q is a pyrimidine ring of formula (Q3)

in which:

Z 10 , Z 11 and Z 12 are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH(C 1 -C 4 -alkyl), and —N(C 1 -C 4 -alkyl) 2 , or

Q is a pyridine ring of formula (Q4)

in which:

Z 13 , Z 14 , Z 15 and Z 16 are independently selected from the group consisting of hydrogen halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -hydroxyalkyl, NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH—CO-C 1 -C 4 -alkyl, and monocyclic heterocycles selected from the group consisting of 4- to 7-membered heterocycloalkyl or 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 halogen, cyano, nitro, —OH, oxo, thiono, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 5 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —S(O)—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, and —SO 2 —(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, or

Q is a pyridine ring of formula (Q5)

in which:

Z 17 , Z 18 , Z 19 and Z 20 are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH(C 1 -C 4 -alkyl), and —N(C 1 -C 4 -alkyl) 2 , or

Q is a 5-membered aromatic heterocycle of formula (Q6)

in which:

T 1 -T 4 are independently selected from the group consisting of N, O, S, C-Z 21 and N-Z 22 , wherein not more than one of T 1 -T 4 is O, not more than one of T 1 -T 4 is S, not more than one of T 1 -T 4 is N-Z 22 , and wherein

each Z 21 is independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, and C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, and

each Z 22 is independently selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkyl-C 5 -C 6 -cycloalkyl, and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or

Q is a 5-membered aromatic heterocycle of formula (Q7)

in which:

U 1 -U 4 are independently selected from the group consisting of N and C-Z 23 , wherein not more than three of U 1 -U 4 are N, and wherein

each Z 23 is independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms,

wherein when Y is O, S or N-R 9 , none of R 7 , R 8 , R 10 and R 11 is —OH, and wherein when X is O, S or N—R 9 , none of R 7 and R 8 is —OH,

or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

3. The compound of claim 1 , wherein:

A is A1 or A2,

o is 0, 1 or 2,

R is selected from the group consisting of halogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy, cyano, and C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R p is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

X, Y are independently selected from the group consisting of CR RN, O, S, and N-R o , wherein at least one of X and Y is CR 7 R 8 ,

R 1 is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl, and cyano-C 1 -C 4 -alkyl,

R 2 is selected from the group consisting of

hydrogen, halogen, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), C(O)—N(C 1 -C 4 -alkyl) 2 ,

—NR 12 R 13 ,

—OR 14 ;

—SR 15 , —S(O)R 15 , —SO 2 R 15 ;

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 5 -C 6 -cycloalkenyl, C 2 -C 4 -alkynyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, —OH, cyano, C 1 -C 4 -alkoxy —C(O)-, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy; —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH(C(O)—C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) (C(O)—C 1 -C 4 -alkyl), —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 -C 4 -C 4 -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, —OH, oxo, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , and 4- to 10-membered heterocycloalkyl,

R 3 is hydrogen or C 1 -C 4 -alkyl,

R 7 is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

R 8 is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

or R 7 and R 8 together form an oxo group (═O),

R 9 is C 1 -C 4 -alkyl,

R 10 is selected from the group consisting of hydrogen, —OH, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 11 is hydrogen,

R 12 and R 13 are independently selected from the group consisting of hydrogen, —NH(—C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkoxy;

C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , —NH—C(O)—C 1 -C 4 -alkyl, —N(C 1 -C 4 -alkyl)-(—C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, Ca-Ce-cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and (C 1 -C 4 -alkoxy) 2 P(═O)—;

phenyl, benzo-C 5 -C 6 -cycloalkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms; and

R 14 is selected from the group consisting of

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, and phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, and heterocyclyl-C 1 -C 4 -alkyl, wherein the heterocyclyl substitutent 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, —OH, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms;

R 15 is selected from the group consisting of

hydrogen;

C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms;

Q is a substituted phenyl ring of formula (Q1)

in which;

Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH(C 1 -C 4 -alkyl), ˜N(C 1 -C 4 -alkyl) 2, 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, —S—(C 1 -C 4 -alkyl), —S(O)—(C 1 -C 4 -alkyl), —SO 2 —(C 1 -C 4 -alkyl), S-(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —S(O)—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, and —SO 2 (C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, or

Z 1 and Z 2 form, together with the carbon atoms that they are connected to, a 5- or 6-membered 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

Z 3 , Z 4 , and Z 5 are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C(O)—, and C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, or

Z 1 , Z 4 , and Z 5 are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, and/or a stereoisomer, tautomer, N-oxide, hydrate, solvate, and/or salt thereof, and/or a mixture thereof.

4. The compound according to of claim 1 , wherein:

A is A1 or A2,

o is 0, 1 or 2,

R is selected from the group consisting of halogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R p is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

X is selected from the group consisting of CR 7 R 8 , O, S, and N—R 9 ,

Y is CR 7 R 8 or O,

R 1 is hydrogen or C 1 -C 4 -alkyl,

R 2 is selected from the group consisting of

hydrogen, halogen, —C(O)—N(C 1 -C 4 -alkyl);

—NR 12 R 13 ;

—OR 14 ;

—SR 15 , —S(O)R 15 , —SO 2 R 15 ;

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkenyl, each of which is optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, —OH, cyano, C 1 -C 4 -alkoxy-C(O)-and-C(O)—NH 2 , C 1 -C 4 -alkoxy, —NH 2 , —N(C)-C 4 -alkyl) 2 , —N(C 1 -C 4 -alkyl) (C(O)—C 1 -C 4 -alkyl); and

a monocyclic or a bicycle 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, —OH, oxo, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C 4 -C 4 -alkyl-, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, —NH 2 , —N(C 1 -C 4 -alkyl) 2 , and 4- to 10-membered heterocycloalkyl,

R 3 is hydrogen or C 1 -C 4 -alkyl,

R 5 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, and C 1 -C 4 -alkoxy,

R 6 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, and C 1 -C 4 -alkoxy,

R 7 is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

R 8 is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

or R 7 and R 8 together form an oxo group (═O),

R 9 is C 1 -C 4 -alkyl,

R 10 is selected from the group consisting of hydrogen, —OH and C 1 -C 4 -alkyl, is hydrogen,

R 12 and R 13 are independently selected from the group consisting of

hydrogen, —NH(—C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkoxy;

C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—N(C 1 -C 4 -alkyl) 2 , —NH—C(O)—C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl, —NH 2 , —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, and (C 1 -C 4 -alkoxy) 2 P(═O)-;

phenyl and benzo-C 3 -C 6 -cycloalkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenoalkoxy 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, —OH, oxo, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms,

R 14 is selected from the group consisting of

4- to 10-membered heterocycloalkyl,

R 15 is selected from the group consisting of

hydrogen;

C 1 -C 4 -alkyl, which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of —OH and —COOH; and

a 6-membered heteroaryl,

Q is a substituted phenyl ring of formula (Q1)

in which:

Z 1 and Z 5 are independently selected from the group consisting of hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, and C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms

Z 2 and Z 4 are independently selected from the group consisting of hydrogen, halogen, cyano, —OH, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —S—(C 1 -C 4 -alkyl)S-(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, and a 4- to 6-membered heterocycloalkyl, and

Z 3 is selected from the group consisting of hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, and —N(C 1 -C 4 -alkyl) 2 , or

Z 1 and Z 2 form, together with the carbon atoms that they are connected to, a 5-membered heterocycloalkyl or a 5-membered heteroaryl, each of which may be optionally substituted with one or two substituents selected from the group consisting of methyl, fluorine and oxo,

Z 3 and Z 5 are hydrogen, and

Z 4 is selected from the group consisting of hydrogen and C 1 -C 4 -alkoxy-C(O)— or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

5. The compound of claim 1 , wherein:

A is selected from the group consisting of

R 1 is hydrogen or methyl,

R 2 is selected from the group consisting of

hydrogen, chlorine, iodine, —C(O)—N(CH 3 ) 2 ,

—NR 12 R 13 ;

—OR 14 ;

—SR 15 , —S(O)R 15 , —SO 2 R 15 ;

methyl, ethyl, propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, ethenyl, propenyl, cyclopentenyl, cyclohexenyl, each of which is optionally substituted by 1 or 2 substituents independently selected from the group consisting of —OH, cyano, ethoxy —C(O)—, —C(O)—NH 2 , methoxy, NH 2 , N(CH 3 ) 2 , and N(CH 3 )(C(O)CH 3 ); and

a monocyclic or a bicyclic heterocycle selected from the group consisting of azetidine, oxetane, pyrrolidine, tetrahydrofurane, pyrazolidine, imidazolidine, 1,2,4-triazolidine, piperidine, piperazine, tetrahydropyrane, tetrahydropyridine, dihydro-2H-pyrane, 1,2-oxazolidine, 1,2-oxazine, morpholine, thiomorpholine, 3,4-dihydroisoquinoline, 2,3-dihydro-indole, 1,3-dihydro-isoindoel, 3,9-dioxa-7-azabicyclo[3.3.1]nonane, 6-oxa-3-azabicyclo[3.1.1]heptane, 8-oxa-3-azabicyclo[3.2.1]octane, thiophene, imidazole, pyrazole, 1,2,4-triazole, 1,2,3 triazole, 1,2,3,4-tetrazole, pyridine, dihydropyridine, pyrimidine, tetrahydropyrimidine, and 4-oxa-7-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, oxo, —COOH, methoxy-C(O)—, ethoxy-C(O)—, tert-butoxy-C(O)—, —C(O)—NH 2 , methyl, methyl-C(O)—, difluoromethyl, trifluoromethyl, hydroxymethyl-, methoxymethyl-, —NH 2 , —NMe 2 , and pyrrolidine,

R 3 is hydrogen or methyl,

R 4 is selected from the group consisting of hydrogen, fluorine, chlorine, —OH, cyano, methyl, methoxy, trifluoromethyl, trifluoromethoxy and NH 2 ,

R 5 is selected from the group consisting of hydrogen, fluorine, chlorine, —OH, cyano, methyl, methoxy and trifluoromethyl,

R 6 is selected from the group consisting of hydrogen, fluorine, chlorine, —OH, cyano, methyl and methoxy,

R 12 and R 13 are independently selected from the group consisting of

hydrogen, —NH(—C(O)-methyl), methoxy;

cyclopropyl, cyclobutyl, benzyl, 1-phenylethyl, 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)—, tert-butoxy-C(O)—, —C(O)—NH 2 , —C(O)—NMe 2 , —NH—C(O)-methyl, methyl, methoxy, cyclopropyl, —NH 2 , NMe 2 , S-methyl, S(O)-methyl, SO 2 -methyl, and (EtO) 2 P(═O)—;

heterocyclyl-methyl, heterocyclyl-ethyl, wherein the heterocyclyl substituent is selected from the group consisting of oxetane, tetrahydrofurane, tetrahydropyrane pyrrolidine, morpholine, pyrazole, imidazole, 1,2,4-oxadiazole, and pyridine, each of which is optionally substituted by 1 substituent independently selected from the group consisting of fluorine, chlorine, —OH, oxo and methyl;

phenyl;

2,3-dihydro-1H-indene, and

a monocyclic heterocycle selected from the group consisting of oxetane, thietane, pyrrolidine, morpholine, tetrahydropyrane, pyridine and pyrazole, each of which is optionally substituted by 1 or 2 substituents independently selected from the group consisting of fluorine, chlorine, —OH, oxo, and methyl;

R 14 is selected from the group consisting of

methyl, ethyl, isopropyl, butyl, cyclopentyl, benzyl, each of which is optionally substituted by 1 or 2 substituents independently selected from the group consisting of fluorine, —OH, methyl, methoxy and cyclopentyl; and

a monocyclic heterocycle selected from the group consisting of pyrrolidin and tetrahydropyran,

R 15 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,

Q is a substituted phenyl ring of formula (Q1)

in which:

Z 1 and Z 5 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, trifluoromethyl and methoxy,

Z 2 and Z 4 are independently selected from the group consisting of hydrogen, fluorine, chlorine, —OH, cyano, methyl, ethyl, tert-butyl, —NHMe, —NMe 2 , trifluoromethyl, methoxy, trifluoromethoxy, —SMe, 2,2,2-trifluoroethyl) sulfanyl and morpholinyl, and

Z 3 is independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, methoxy, difluoromethoxy and —NMe 2 ,

or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

6. The compound of claim 1 , wherein:

A is selected from the group consisting of

or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

7. The compound of claim 1 , wherein:

R 2 is selected from the group consisting of

hydrogen, chlorine, iodine, —C(O)—N(CH 3 ) 2 ,

—NR 12 R 13 ;

—OR 14 ;

—SR 15 , —S(O) R 15 , —SO 2 R 15 ;

a monocyclic or a bicyclic heterocycle selected from the group consisting of azetidine, oxetane pyrrolidine, tetrahydrofurane, pyrazolidine, imidazolidine, 1,2,4-triazolidine, piperidine, piperazine, tetrahydropyridine, dihydro-2H-pyrane, 1,2-oxazolidine, 1,2-oxazine, morpholine, thiomorpholine, 3,4-dihydroisoquinoline, 2,3-dihydro-indole, 1,3-dihydro-isoindoel, 3,9-dioxa-7-azabicyclo[3.3.1]nonane, 6-oxa-3-azabicyclo[3.1.1]heptane, 8-oxa-3-azabicyclo[3.2.1]octane, thiophene, imidazole pyrazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, pyridine, dihydropyridine pyrimidine, tetrahydropyrimidine, and 4-oxa-7-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, oxo, —COOH, methoxy-C(O)—, ethoxy-C(O)— tert-butoxy-C(O)—, —C(O)—NH 2 , methyl, methyl-C(O))—, difluoromethyl, trifluoromethyl, hydroxymethyl-, methoxymethyl-, —NH 2 , —NMe 2 , and pyrrolidine,

R 12 and R 13 are independently selected from the group consisting of

hydrogen, —NH(—C(O)-methyl), methoxy;

cyclopropyl, cyclobutyl, benzyl, 1-phenylethyl, 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)—, tert-butoxy-C(O)—, —C(O)—NH 2 , —C(O)—NMe 2 , —NH—C(O)-methyl, methyl, methoxy, cyclopropyl, —NH 2 , NMe 2 , S-methyl, S(O)-methyl, SO 2 -methyl, and (EtO) 2 P(═O)-;

phenyl;

2,3-dihydro-1H-indene, and

R 14 is selected from the group consisting of

a monocyclic heterocycle selected from the group consisting of pyrrolidin and tetrahydropyran,

R 15 is selected from the group consisting of

methyl and ethyl, each of which is optionally substituted by 1substituent independently selected from the group consisting of —OH and —COOH; and

pyridine,

or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

8. The compound of claim 1 , wherein:

Q is a substituted phenyl ring of formula (Q1)

in which:

Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , 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, —S—(C 1 -C 4 -alkyl), —S(O)—(C 1 -C 4 -alkyl), —SO 2 —(C 1 -C 4 -alkyl), —S—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, —S(O)—(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, and —SO 2 —(C 1 -C 4 -halogenoalkyl) having 1 to 5 halogen atoms, or

or a stereoisomers, tautomers, N-oxides, hydrates, solvates, or salts thereof, or mixtures of same.

9. The compound of claim 1 , wherein:

Q is a substituted phenyl ring of formula (Q1)

in which:

Z 1 and Z 5 are independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, methoxy and trifluoromethyl,

Z 3 is independently selected from the group consisting of hydrogen, fluorine, chlorine, methyl, methoxy, difluoromethoxy and —NMe 2 ,

or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

10. The compound of claim 1 , wherein:

A is A3 or A4

wherein

R p is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl;

or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

11. A method of preparing the compound of formula (I) of claim 1 , said method comprising allowing an intermediate compound of formula 1C:

wherein Hal is halogen,

to react with a compound of formula 1D:

Q-B(OR) 2 1D,

in which each R may be individually H or Me or both R are pinacolate,

thereby giving a compound of formula (I):

12. A compound of formula 1C:

in which:

R 2 is as defined for the compound of formula (I) according to claim 1 ,

wherein A, R 1 , R 3 , R 4 , R 5 , and R 6 are

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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl, —S(O)—C 1 -C 4 -halogenoalkyl and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R p is selected from the group consisting of hydrogen and C 1 -C 4 -alkyl,

X, Y are independently selected from the group consisting of CR 7 R 8 , O, S, and N—R 9 , wherein at least one of X and Y is CR 7 R 8 , or

X, Y form together a ring member selected from the group consisting of —C(O)—O—, —C(O)—NR 9 —, —S(O)—NR 9 —, —SO 2 —NR 9 — and —SO 2 —O—,

R 1 is selected from the group consisting of hydrogen, cyano, ˜CHO, —OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogenocycloalkyl having 1 to 5 halogen atoms, C 5 -C 4 -alkenyl, C 1 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkyl, cyano-C 1 -C 4 -alkyl, —NH—C 1 -C 4 -alkyl, —N(C 1 -C 4 -alkyl) 2 , NH 2 -C 1 -C 4 -alkyl-, C 1 -C 4 -alkyl-NH—C 1 -C 4 -alkyl-, (C 1 -C 4 -alkyl) 2 N—C 1 -C 4 -alkyl-, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -halogenoalkyl-C(O)-having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C(O)—, benzyloxy-C(O)—C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-C(O)—, —SO 2 —C 1 -C 4 -alkyl, and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

heterocyclyl-C 1 -C 4 -alkyl, wherein the heterocyclyl substituent of the heterocyclyl-C 1 -C 4 -alkyl 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, —NO 2 , cyano, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 - halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R 2 is selected from the group consisting of

hydrogen, halogen, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 ;

—NR 12 R 13 ;

—OR 14 ;

—SR 15 , —S(O)R 15 , —SO 2 R 15 ;

C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkenyl, C 2 -C 4 -alkynyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, —OH, —NO 2 , cyano, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 1 , —NH(C(O)—C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl)(C(O)—C 1 -C 4 -alkyl), —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

heterocyclyl-C 1 -C 4 -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, —NO 2 , cyano, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO-C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), -N(C 1 -C 4 -alkyl) 2 , —S-C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -alkyl-C(O)—, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, and 4- to 10-membered heterocycloalkyl,

R 3 is hydrogen or C 1 -C 4 -alkyl,

R 4 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -alkyl —C(O)—, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, and —SO 2 —C 1 -C 4 -alkyl, optionally hydrogen and hale en, optionally fluorine and chlorine;

R 5 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -alkyl —C(O)—, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, and —SO 2 —C 1 -C 4 -alkyl,

R 6 is selected from the group consisting of hydrogen, halogen, —OH, cyano, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 4 -alkyl —C(O)—, —NH 2 , —NH(C)-C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, and —SO 2 —C 1 -C 4 -alkyl,

R 7 is selected from the group consisting of hydrogen, —OH, fluorine, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 8 is selected from the group consisting of hydrogen, —OH, fluorine, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

or R 7 and R 8 together form an oxo group (═O),

R 9 is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and C 1 -C 4 -alkoxy,

R 10 is selected from the group consisting of hydrogen, —OH, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 11 is selected from the group consisting of hydrogen, C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy,

R 12 and R 13 are independently selected from the group consisting of hydrogen, —OH, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —NH(—C(O)—C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl)(—C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C(O)—;

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , —NH—C(O)—C 1 -C 4 -alkyl, —N(C 1 -C 4 -alkyl) (—C(O)—C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —SO═C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and (C 1 -C 4 -alkoxy) 2 P(═O)—;

heterocyclyl-C 1 -C 4 -alkyl, wherein the heterocyclyl substituent of the heterocyclyl-C 1 -C 4 -alkyl 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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C—C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

phenyl, benzo-C 1 -C 4 -cycloalkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, cyano, nitro, —OH, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, Ca-Cr-cycloalkyl, —NH 2 , —NH(C)-C 4 -alkyl), ˜N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO—C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R 14 is selected from the group consisting of

—NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 ;

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, ˜C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl), C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 5 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 3 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S-C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C)-C 4 -alkyl), —C(O)—N(C)-C 4 -alkyl) 1 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

R 15 is selected from the group consisting of

hydrogen;

C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, phenyl-C 1 -C 4 -alkyl, each of which is optionally substituted by 1, 2 or 3 substituents independently selected from the group consisting of halogen, —OH, cyano, —COOH, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -Ce-cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms;

heterocyclyl-C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 , —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 2 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -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, C 1 -C 4 -alkoxy-C(O)—, —C(O)—NH 2 —C(O)—NH(C 1 -C 4 -alkyl), —C(O)—N(C 1 -C 4 -alkyl) 2 , C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 3 -C 6 -cycloalkyl, —NH 2 , —NH(C 1 -C 4 -alkyl), —N(C 1 -C 4 -alkyl) 1 , —S—C 1 -C 4 -alkyl, —S(O)—C 1 -C 4 -alkyl, —SO 2 —C 1 -C 4 -alkyl, —S—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms, —S(O)—C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms and —SO 2 —C 1 -C 4 -halogenoalkyl having 1 to 5 halogen atoms,

wherein when Y is O, S or N-R 9 , none of R 7 , R 8 , R 10 and R 11 is —OH or C 1 -C 4 -alkoxy, and wherein when X is O, S or N—R 9 , none of R 7 and R 8 is —OH or C 1 -C 4 -alkoxy;

and

Hal is halogen,

or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof.

13. A pharmaceutical composition comprising the compound of formula (I) of claim 1 or a stereoisomer, tautomer, N-oxide, hydrate, solvate, or salt thereof, or a mixture thereof and one or more pharmaceutically acceptable excipients.

14. A method for the control or treatment of a helminthic infection comprising administering an effective amount of the compound of formula (I) claim 1 to a subject in need thereof.

15. A method for the control or treatment of a helminthic infection comprising administering an effective amount of the pharmaceutical composition of claim 13 .

Assignments (2)

CHANGE OF NAME Recorded May 7, 2025

From: BAYER ANIMAL HEALTH GMBH

To: ELANCO ANIMAL HEALTH GMBH

Reel/Frame 071053/0606 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 27, 2022

From: ALIG, BERND; HUEBSCH, WALTER; GRIEBENOW, NILS; SCHWARZ, HANS-GEORG; ZHUANG, WEI; KULKE, DANIEL; BOEHM, CLAUDIA; HEISLER, IRING; JANSSEN, ISA JANA IRINA; BOERNGEN, KIRSTEN

To: BAYER ANIMAL HEALTH GMBH

Reel/Frame 058796/0515 →

Priority Claims (1)

EP 19189099 · Jul 30, 2019 · regional

Continuity (1)

Related Publication 20220274971A1 · Sep 1, 2022

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