Anthelmintic heterocyclic compounds
This invention provides for compounds of the formula: wherein the variables are defined herein, or salt thereof, compositions comprising these compounds, and method for the treatment, control or prevention of a parasitic infestation or infection in an animal in need thereof by administering an effective amount of these compounds to said animal.
1. A compound of Formula (I):
wherein:
L is L1, L2, L3, L4, L5, L6, L7, L8, L9, L10, L11, L12, L13, L14 or L15:
R′ is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl;
R 1 is hydrogen, cyano, halogen, hydroxyl, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkynyloxy, optionally substituted alkoxyalkyl, optionally substituted aminoalkyl, optionally substituted alkylaminoalkyl, optionally substituted dialkylaminoalkyl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkoxy, optionally substituted heterocyclyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —SO p (optionally substituted alkyl or haloalkyl), —SF 5 , or —NR a R b , wherein R a and R b are independently H or optionally substituted alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O, Si and S and may be optionally substituted;
R 2 is hydrogen, cyano, halogen, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl; optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkoxy, optionally substituted heterocyclyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —SO p (optionally substituted alkyl or haloalkyl), —SF 5 , or —NR a R b , wherein R a and R b are independently H or optionally substituted alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O, Si and S and may be optionally substituted;
R 3 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted dialkylaminocarbonyl, —S(O) p (optionally substituted alkyl), —SF 5 , optionally substituted heterocyclyl, optionally substituted 6- to 10-membered aryl, optionally substituted 5- to 10-membered heteroaryl, a spirocyclic heterocyclyl-carbocyclyl group, a spirocyclic heterocyclyl-heterocyclyl group, a spirocyclic carbocyclyl-carbocyclyl group, a spirocyclic carbocyclyl-heterocyclyl group or —NR a R b , wherein R a and R b are independently H or optionally substituted alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O, Si and S and may be optionally substituted;
R 4 and R 4′ are independently in each occurrence, hydrogen, halogen, cyano, nitro, hydroxyl, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted cycloalkyl, optionally substituted cycloalkoxy, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, or optionally substituted di(alkyl)aminocarbonyl, optionally substituted alkylcarbonyloxy, optionally substituted alkylcarbonylamino, optionally substituted aryl, optionally substituted heteroaryl, —SF 5 , —SO p (optionally substituted alkyl or haloalkyl); or R 4 together with R 4′ together form a 2-6-membered chain optionally containing one or two heteroatoms selected from the group consisting of N, O, Si and S to form carbocyclic or heterocyclic ring together with the carbon atom to which they are attached; or —NR c R d , wherein R c and R d are independently H or optionally substituted alkyl; or R c and R d may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O, Si and S and may be optionally substituted;
R 8 is hydrogen, halogen, alkyl, haloalkyl, cycloalkyl, alkenyl or alkynyl;
R 9 and R 9′ are independently hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or cycloalkoxy, or R 9 together with R 9′ form a 2-6-membered chain optionally containing one or two heteroatoms selected from the group consisting of N, O, Si and S to form carbocyclic or heterocyclic ring together with the carbon atom to which they are attached;
Q is N or C—R 8 ;
X is O, S or N—R′;
Y 1 and Y 6 are each independently N, C, or —CR 4 —;
Y 2 , Y 3 , Y 4 and Y 5 are each independently N, NR′, S, O, —CR 4 — or CR 4 R 4′ ;
W is CR 5 R 6 , O, SO p , or N—R 7 ,
Z is CR 5 R 6 , O, SO p , or N—R 7 ,
wherein
R 5 and R 6 are independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or cycloalkoxy; or R 5 together with R 6 form a 2-6-membered chain optionally containing one or two heteroatoms selected from the group consisting of N, O, Si and S to form carbocyclic or heterocyclic ring together with the carbon atom to which they are attached;
R 7 is hydrogen or C 1 -C 4 -alkyl; and
wherein at most three of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 are heteroatoms;
a is 0 or 1;
q is 0 or 1;
p is independently in each occurrence is 0, 1, or 2; and
the dashed bonds ( ) signifies a single or double bond;
or a pharmaceutically acceptable salt thereof.
2. The compound of Formula (I) of claim 1 ,
wherein:
R 1 is hydrogen, cyano, halogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, hydroxy-C 1 -C 6 -alkyl, hydroxy-C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, amino-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -haloalkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -haloalkylaminocarbonyl, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heteroaryl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 3 -C 8 -cycloalkenyl, optionally substituted C 3 -C 8 -cycloalkyloxy, optionally substituted 3- to 7-membered heterocyclyl, —SF 5 , —SO p (optionally substituted C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl), or —NR a R b wherein R a and R b are independently H or optionally substituted C 1 -C 6 -alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
R 2 is hydrogen, cyano, halogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, optionally substituted phenyl; optionally substituted phenyloxy, optionally substituted 5- or 6-membered heteroaryl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 3 -C 8 -cycloalkenyl, optionally substituted C 3 -C 8 -cycloalkyloxy, optionally substituted 3- to 7-membered heterocyclyl containing from one to three heteroatoms selected from the group consisting of N, O and S, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -haloalkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -haloalkylaminocarbonyl, —SO p (optionally substituted C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl), SF 5 , or —NR a R b wherein R a and R b are independently H, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
R 3 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 3 -C 8 -cycloalkenyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -haloalkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -haloalkylaminocarbonyl, —SF 5 , —S(O)p(C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl), optionally substituted 3- to 7-membered heterocyclyl containing from one to three heteroatoms selected from the group consisting of N, O and S; optionally substituted phenyl, optionally substituted 5- to 10-membered heteroaryl, a 5- to 11-membered spirocyclic heterocyclyl-carbocyclyl group, a 5- to 11-membered spirocyclic heterocyclyl-heterocyclyl group, a 5- to 11-membered spirocyclic carbocyclyl-carbocyclyl group, a 5- to 11-membered spirocyclic carbocyclyl-heterocyclyl group, or —NR a R b , wherein R a and R b are independently H, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
R 4 and R 4′ are independently in each occurrence, hydrogen, halogen, cyano, nitro, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted C 3 -C 8 -cycloalkyloxy, optionally substituted C 1 -C 6 -alkylcarbonyl, optionally substituted C 1 -C 6 -alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted C 1 -C 6 -alkylaminocarbonyl, optionally substituted di(C 1 -C 6 -alkyl)aminocarbonyl, optionally substituted C 1 -C 6 -alkylcarbonyloxy, optionally substituted C 1 -C 6 -alkylcarbonylamino, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, —SF 5 , —SO p (optionally substituted C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl); or R 4 together with R 4′ together form a 2-6-membered chain optionally containing one or two heteroatoms selected from the group consisting of N, O, Si and S to form carbocyclic or heterocyclic ring together with the carbon atom to which they are attached; or —NR c R d , wherein R c and R d are independently H, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or R c and R d may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
R 8 is hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl;
R 9 and R 9′ are independently hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or C 3 -C 8 -cycloalkoxy, or R 9 together with R 9′ form a 2-6-membered chain optionally containing one or two heteroatoms selected from the group consisting of N, O, Si and S to form carbocyclic or heterocyclic ring together with the carbon atom to which they are attached; and
R′ is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, optionally substituted C 3 -C 8 -cycloalkyl, or optionally substituted phenyl.
3. The compound of Formula (I) according to claim 1 or 2 , wherein
R 1 is hydrogen, cyano, optionally substituted C 1 -C 4 -alkyl, optionally substituted C 1 -C 4 -alkoxy, optionally substituted C 2 -C 4 -alkenyl, optionally substituted C 2 -C 4 -alkynyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted, saturated or unsaturated 5-, 6-, or 7-membered heterocycle, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryloxy, optionally substituted C 1 -C 4 -alkylcarbonyl, optionally substituted C 1 -C 4 -alkoxycarbonyl, aminocarbonyl, optionally substituted C 1 -C 4 -alkylaminocarbonyl, optionally substituted C 1 -C 4 -dialkylaminocarbonyl, optionally substituted SO p (optionally substituted alkyl or haloalkyl), amino, —NH-optionally substituted C 1 -C 4 -alkyl, or —NR a R b , wherein R a and R b are independently optionally substituted alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-5-, 6-, 7-, or 8-membered-heterocyclyl group, which may be optionally substituted, and may include one or two additional heteroatoms selected from the group consisting of N, O and S;
R′ is hydrogen or C 1 -C 4 -alkyl;
R 2 is hydrogen, halogen, cyano, nitro, —OH, optionally substituted C 1 -C 4 -alkyl, optionally substituted C 1 -C 4 -alkoxy, optionally substituted C 3 -C 8 -cycloalkyl, amino, NH-optionally substituted C 1 -C 4 -alkyl, —SF 5 , or —NR a R b , wherein R a and R b are independently optionally substituted C 1 -C 4 -alkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3, 4, 5, 6, 7, or 8 membered-heterocyclyl group, which may be optionally substituted, and may include one or two additional heteroatoms selected from the group consisting of N, O and S; —SO p (optionally substituted C 1 -C 4 -alkyl or haloalkyl);
R 3 is optionally substituted C 1 -C 4 -alkyl, optionally substituted phenyl, optionally substituted 5- to 10-membered heteroaryl, optionally substituted C 3 -C 8 -cycloalkyl, a 5- to 11-membered spirocyclic heterocyclyl-carbocyclyl group, a 5- to 11-membered spirocyclic heterocyclyl-heterocyclyl group, a 5- to 11-membered spirocyclic carbocyclyl-carbocyclyl group, or a 5- to 11-membered spirocyclic carbocyclyl-heterocyclyl group; and
each R 4 is independently hydrogen, halogen, cyano, nitro, hydroxyl, optionally substituted C 1 -C 4 -alkyl, optionally substituted C 1 -C 4 -alkoxy, optionally substituted C 3 -C 8 -cycloalkyl, amino, NH-optionally substituted C 1 -C 4 -alkyl, —SF 5 , or —NR c R d , wherein R c and R d are independently optionally substituted C 1 -C 4 -alkyl; or R c and R d may form, with the nitrogen to which they are attached, a 3, 4, 5, 6, 7, or 8 membered-heterocyclyl group, which may be optionally substituted and may include one or two additional heteroatoms selected from the group consisting of N, O and S, SO p (optionally substituted C 1 -C 4 -alkyl or haloalkyl.
4. The compound of Formula (I) according to claim 1 or 2 , wherein Q is N.
5. The compound of Formula (I) according to claim 1 or 2 , wherein Q is C—R 8 .
6. The compound of Formula (I) according to claim 1 or 2 , wherein X is O.
7. The compound of Formula (I) according to claim 1 or 2 , wherein X is S.
8. The compound of Formula (I) according to claim 1 or 2 , wherein a is 1 and q is 1.
9. The compound of Formula (I) according to claim 1 or 2 , wherein a is 0 and q is 0.
10. The compound of Formula (I) according to claim 1 or 2 , wherein a is 1 and q is 0.
11. The compound of Formula (I) according to claim 1 or 2 , wherein:
L is L1;
R′ is hydrogen or C 1 -C 4 -alkyl;
R 1 is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, hydroxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -haloalkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -haloalkylaminocarbonyl, di-C 1 -C 4 -alkylaminocarbonyl, di-C 1 -C 6 -haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heteroaryl or optionally substituted 5- or 6-membered heterocyclyl containing 1 to 3 N, S or O heteroatoms or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5- or 6-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
R 2 is hydrogen, halogen, —SF 5 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, optionally substituted C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -haloalkylaminocarbonyl, di-C 1 -C 4 -alkylaminocarbonyl, di-C 1 -C 4 -haloalkylaminocarbonyl, —SO p (optionally substituted C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl), or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
R 3 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, optionally substituted C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -haloalkylaminocarbonyl, di-C 1 -C 4 -alkylaminocarbonyl, di-C 1 -C 4 -haloalkylaminocarbonyl, —SO p (optionally substituted C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl), —SF 5 , optionally substituted 3- to 7-membered heterocyclyl containing from one to three heteroatoms selected from the group consisting of N, O and S; optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, a 5- to 11-membered spirocyclic heterocyclyl-carbocyclyl group, a 5- to 11-membered spirocyclic heterocyclyl-heterocyclyl group, a 5- to 11-membered spirocyclic carbocyclyl-carbocyclyl group, wherein each ring of said spirocyclic group contains 3, 4, 5 or 6 ring atoms; or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5-, 6-, 7-, or 8-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
R 4 is independently in each occurrence, hydrogen, halogen, —SF 5 , C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, —SO p (optionally substituted C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl), or —NR c R d wherein R c and R d are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
R 8 is hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
X is O or S;
Z is O; and
W is CR 5 R 6 .
12. The compound of Formula (I) according to claim 11 , wherein a is 1 and q is 1.
13. The compound of Formula (I) according to claim 11 , wherein a is 0 or 1 and q is 0.
14. The compound of Formula (I) according to claim 11 , which is represented by the compound of formula (Ie):
wherein:
each R 10 is independently halogen, cyano, hydroxyl, optionally substituted C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -haloalkoxy-C 1 -C 6 -alkyl, optionally substituted phenyl, optionally substituted phenyloxy, optionally substituted 5- or 6-membered heteroaryl, optionally substituted 5- to 6-membered heterocyclyl containing from one to three heteroatoms selected from the group consisting of N, O, Si and S, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, C 1 -C 6 -haloalkylaminocarbonyl, di-C 1 -C 6 -alkylaminocarbonyl, di-C 1 -C 6 -haloalkylaminocarbonyl, C 1 -C 6 -alkylthio, C a -C 6 haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, amino, C 1 -C 6 -alkylamino, di-C 1 -C 6 -alkylamino, or SF 5;
R 1 is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, hydroxy-C 1 -C 4 -alkyl, alkoxy-C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, aminocarbonyl, C 1 -C 4 -alkylaminocarbonyl, C 1 -C 4 -haloalkylaminocarbonyl, di-C 1 -C 4 -alkylaminocarbonyl, di-C 1 -C 6 -haloalkylaminocarbonyl, optionally substituted 5- or 6-membered heterocyclyl containing 1 to 3 N, S or O heteroatoms or —NR a R b wherein R a and R b are independently H, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; or R a and R b may form, with the nitrogen to which they are attached, a 3-, 4-, 5- or 6-membered-heterocyclyl group, which may include one to three additional heteroatoms selected from the group consisting of N, O and S and may be optionally substituted;
R 2 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, —SO p (optionally substituted C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl), —SF 5 , or —NR a R b wherein R a and R b are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
R 4 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, —SO p (optionally substituted C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl), —SF 5 , or —NR c R d wherein R c and R d are independently H, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;
R 5 and R 6 are independently hydrogen, halogen, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl;
R′ is hydrogen or C 1 -C 3 -alkyl;
R 8 is hydrogen;
R 9 and R 9′ are independently hydrogen, halogen, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl;
Y 2 , Y 3 , Y 4 , Y 5 are independently CR 4 or N;
a is 0 or 1; and
m is 0, 1, 2, or 3.
15. The compound according to claim 14 , wherein each R 10 is independently halogen and m is 2 or 3.
16. The compound according to claim 14 , wherein each R 10 is independently chloro or fluoro and m is 2 or 3.
17. The compound according to claim 14 , wherein:
each R 10 is independently chloro or fluoro;
m is 2 or 3;
R 1 is C 1 -C 4 -alkyl or —NR a R b ;
R 2 is hydrogen, halogen, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl;
W is CH 2 ;
Z is O; and
R 9 and R 9′ are each hydrogen.
18. The compound according to claim 14 , wherein
R 1 C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, amino, C 1 -C 4 -alkylamino, di(C 1 -C 4 -alkyl)amino, morpholino, pyranyl, tetrahydropyranyl, or dihydropyranyl;
R 2 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 haloalkyl; and
R 4 is independently in each occurrence hydrogen, halogen, C 1 -C 4 -alkyl or C 1 -C 4 haloalkyl.
19. The compound according to claim 18 , wherein
R 1 C 1 -C 4 -alkyl, di(C 1 -C 4 -alkyl)amino, morpholino, pyranyl, tetrahydropyranyl, or dihydropyranyl;
R 2 is hydrogen, halogen, C 1 -C 3 -alkyl or C 1 -C 3 haloalkyl; and
R 4 is independently in each occurrence hydrogen, halogen, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl;
R 10 is chloro or fluoro; and
m is 2 or 3.
20. The compound of any of claims 14 to 17 , wherein each of Y 2 , Y 3 , Y 4 and Y 5 are independently —C—R 4 .
21. The compound of any of claims 14 to 17 , wherein Y 2 is N; and Y 3 , Y 4 and Y 5 are independently —C—R 4 .
22. The compound of any of claims 14 to 17 , wherein Y 3 is N; and Y 2 , Y 4 and Y 5 are independently —CR 4 .
23. The compound of any of claims 14 to 17 , wherein Y 4 is N and Y 2 , Y 3 and Y 5 are independently —CR 4 .
24. The compound of any of claims 14 to 17 , wherein Y 5 is N and Y 2 , Y 3 and Y 4 are independently —CR 4 .
25. The compound of any of claims 14 to 17 , wherein Y 2 and Y 3 are N; and Y 4 and Y 5 are independently —CR 4 .
26. The compound of any of claims 14 to 17 , wherein Y 3 and Y 4 are N; and Y 2 and Y 5 are independently —CR 4 .
27. The compound of any of claims 14 to 17 , wherein Y 4 and Y 5 are N; and Y 2 and Y 3 are independently —CR 4 .
28. The compound of any of claims 14 to 17 , wherein Y 2 and Y 4 are N; and Y 3 and Y 5 are independently —CR 4 .
29. The compound of any of claims 14 to 17 , wherein Y 3 and Y 5 are N; and Y 2 and Y 4 are independently —CR 4 .
30. The compound of any of claims 14 to 17 , wherein Y 3 and Y 4 are N; and Y 2 and Y 5 are independently —CR 4 .
31. A compound of formula (I);
wherein R 1 , R 2 , R 3 and L are shown in the table below;
L1 is:
wherein X is oxygen and R′ is hydrogen;
L2 is:
wherein X is oxygen and R′ is hydrogen;
“Me” is methyl;
“i-Pr” is isopropyl;
“t-Bu” is tert-butyl;
prop- 1 -en- 2 -yl is
2 -F-prop- 2 -yl represents the group
1 , 1 -difluoroethyl represents the group
and the group
Cmpd.
Ring
#
L
R3
R2
R3
System
271
L1
i-Pr
Me
3,5-di-Cl—Ph
A
326
L1
i-Pr
Me
A
327
L1
i-Pr
Me
A
326-0
L1
i-Pr
Me
A
324
L1
i-Pr
Me
A
325
L1
i-Pr
Me
A
323
L1
i-Pr
Me
t-Bu
A
175
L1
i-Pr
Me
3,5-di-F—Ph
A
A407
L1
i-Pr
Me
2,6-di-F—Ph
A
A406
L1
i-Pr
Me
2,6-di-Cl—Ph
A
A413
L1
i-Pr
Me
2,4-di-F—Ph
A
A408
L1
Me
3,5-di-Cl—Ph
A
A412
L1
i-Pr
Me
4-F—Ph
A
A410
L1
i-Pr
Me
3-Cl-4-F—Ph
A
A411
L1
i-Pr
Me
3,5-di-Cl—Ph
C
A409
L1
—N(CH 3 ) 2
Me
3,5-di-Cl—Ph
A
A414
L1
i-Pr
Me
3,5-di-Cl—Ph
D
306
L1
t-Bu
Me
3,5-di-Cl—Ph
A
297
L1
t-Bu
Me
3,5-di-Cl—Ph
B
365
L1
i-Pr
Me
cyclopropyl
A
371
L1
i-Pr
Me
A
370
L1
i-Pr
Me
A
366
L1
i-Pr
Me
CN
A
369
L1
i-Pr
Me
A
308
L1
prop-1-en-2-
Me
3,5-di-Cl—Ph
B
yl
364
L1
i-Pr
Me
3,5-di-Cl—Ph
E
352
L1
i-Pr
H
3,5-di-Cl—Ph
A
320-0
L1
i-Pr
Me
3,5-di-F—Ph
F
345
L1
i-Pr
Me
2,3,5-tri-F—Ph
A
344
L1
i-Pr
Me
2,3,5-tri-F—Ph
B
294
L1
i-Pr
Me
3,5-di-Cl—Ph
B
320
L2
i-Pr
Me
3,5-di-F—Ph
A
277
L1
2-F-prop-2-
Me
3,5-di-F—Ph
A
yl
323-0
L1
i-Pr
Me
—CH 2 CH(CH 3 ) 2
A
298-0
L1
t-Bu
CF 3
3-Cl—Ph
B
299-0
L1
t-Bu
CF 3
3-Cl—Ph
A
299
L1
t-Bu
CF 3
3,5-di-Cl—Ph
B
298
L1
t-Bu
CF 3
3,5-di-Cl—Ph
A
304-0
L1
i-Pr
3,5-di-Cl—Ph
Cl
B
321
L1
i-Pr
4-F—Ph
3,5-di-F—Ph
A
322
L1
i-Pr
Me
A
304
L1
i-Pr
Cl
3,5-di-Cl—Ph
B
307
L1
prop-1-en-2-
Me
3,5-di-F—Ph
B
yl
296
L1
i-Pr
CF 3
3,5-di-Cl—Ph
B
295
L1
i-Pr
CF 3
3,5-di-Cl—Ph
A
293
L1
i-Pr
Me
2,3-di-Cl—Ph
B
276
L1
i-Pr
CF 3
3,5-di-F—Ph
A
274
L1
i-Pr
Me
2,3-di-Cl—Ph
A
273
L1
i-Pr
Me
3-F—Ph
A
272
L1
i-Pr
Me
3-Cl-5-F—Ph
A
275
L1
i-Pr
Me
3,5-di-F—Ph
B
279
L1
prop-1-en-2-
Me
3,5-di-F—Ph
A
yl
174
L1
H
H
2,6-di-F—Ph
A
A400
L1
1,1-
Me
3,5-di-Cl—Ph
A
difluoroethyl
A401
L1
CF 3
Me
3,5-di-Cl—Ph
A
373
L1
i-Pr
Me
A
372-0
L1
i-Pr
Me
A
A402
L1
i-Pr
Me
3,5-di-Cl—Ph
G
A403
L1
i-Pr
—CH 2 OH
3,5-di-Cl—Ph
A
A404
L1
i-Pr
—CF 2 CF 3
3,5-di-Cl—Ph
A
394
L1
—OCH 3
H
3,5-di-Cl—Ph
A
398
L1
—OCH 2 CH 3
H
3,5-di-Cl—Ph
A
A405
L1
—CHF 2
Me
3,5-di-Cl—Ph
A
573
L1
t-Bu
Cl
2,3,5-tri-F—Ph
A
559
L1
i-Pr
—CN
3,5-di-Cl—Ph
A
614
L1
t-Bu
Me
3,5-di-Cl—Ph
AAA
451
L1
—N(CH 3 ) 2
CF 3
3,5-di-Cl—Ph
A
572
L1
t-Bu
Cl
2,5-di-Cl-4-F—Ph
A
528
L1
i-Pr
Me
2,5-di-Cl-4-F—Ph
A
571
L1
t-Bu
Cl
2,4,5-tri-F—Ph
A
574
L1
t-Bu
Cl
2,3-di-Cl-5-F—Ph
A
A415
L1
i-Pr
Me
3,5-di-Cl—Ph
H
A416
L1
i-Pr
Me
3,5-di-Cl—Ph
I
A417
L1
i-Pr
Me
3,5-di-Cl—Ph
J
A418
L1
i-Pr
Me
3,5-di-Cl—Ph
K
A419
L1
i-Pr
Me
3,5-di-Cl—Ph
L
A420
L1
i-Pr
Me
3,5-di-Cl—Ph
M
560
L1
i-Pr
—CHF 2
3,5-di-Cl—Ph
A
305
L1
i-Pr
—CHF 2
3,5-di-Cl—Ph
B
A421
L1
Me
2,6-di-Cl-4-F
A
A422
L1
Me
2,3,5-tri-F—Ph
A
420
L1
t-Bu
Cl
3,5-di-Cl—Ph
A
A423
L1
i-Pr
Me
3,5-di-Cl—Ph
N
A424
L1
i-Pr
Me
3,5-di-Cl—Ph
0
523
L1
t-Bu
Me
2,6-di-Cl-4-F—Ph
A
A425
L1
i-Pr
Me
3,5-di-Cl—Ph
P
A426
L1
i-Pr
Me
3,5-di-Cl—Ph
Q
526
L1
t-Bu
Me
2,3-di-Cl-5-F—Ph
A
527
L1
i-Pr
Me
2,4,6-tri-F—Ph
A
524
L1
t-Bu
Me
2,4,6-tri-F—Ph
A
525
L1
t-Bu
Me
2,3,5-tri-F—Ph
A
414-0
L2
i-Pr
Me
3,5-di-Cl—Ph
R
514
L2
i-Pr
Me
3,5-di-Cl—Ph
E
A427
L1
i-Pr
Me
3,5-di-Cl—Ph
S
A428
L1
i-Pr
Me
3,5-di-Cl—Ph
T
A429
L1
i-Pr
Me
3,5-di-Cl—Ph
U
A430
L1
i-Pr
Me
3,5-di-Cl—Ph
V
418
L1
t-Bu
H
3,5-di-Cl—Ph
A
513
L2
i-Pr
Me
3,5-di-Cl—Ph
A
513-0
L2
i-Pr
Me
3,5-di-Cl—Ph
F
511
L1
H
3,5-di-Cl—Ph
A
512
L1
—N(CH 3 ) 2
H
3,5-di-Cl—Ph
A
A431
L1
i-Pr
Me
3,5-di-Cl—Ph
W
450
L1
CF 3
3,5-di-Cl—Ph
A
A432
L1
i-Pr
Me
3,5-di-Cl—Ph
X
A473
L1
i-Pr
Me
3,5-di-Cl—Ph
Y
A433
L1
i-Pr
Me
3,5-di-Cl—Ph
Z
A434
L1
i-Pr
Me
3,5-di-Cl—Ph
AA
A435
L1
i-Pr
Me
3,5-di-Cl—Ph
AB
A436
L1
L1
i-Pr
Me
N/A (H)
A437
L1
i-Pr
Me
3,5-di-Cl—Ph
AC
A438
L1
i-Pr
Me
3,5-di-Cl—Ph
AD
A439
L1
i-Pr
Me
3,5-di-Cl—Ph
AF
A440
L1
i-Pr
Me
3,5-di-Cl—Ph
AG
A441
L1
i-Pr
Me
3,5-di-Cl—Ph
AH
A442
L1
i-Pr
Me
3,5-di-Cl—Ph
AE
A443
L1
i-Pr
Me
3,5-di-Cl—Ph
AJ
A445
L1
i-Pr
Me
3,5-di-Cl—Ph
AK
A446
L1
i-Pr
Me
3,5-di-Cl—Ph
AL
A447
L1
i-Pr
Me
3,5-di-Cl—Ph
AM
A448
L1
i-Pr
Me
3,5-di-Cl—Ph
AO
A449
L1
i-Pr
Me
3,5-di-Cl—Ph
AQ
A450
L1
i-Pr
Me
3,5-di-Cl—Ph
AR
A451
L1
i-Pr
Me
3,5-di-Cl—Ph
AP
A452
L1
i-Pr
Me
3,5-di-Cl—Ph
AS
A472
L1
i-Pr
Me
3,5-di-Cl—Ph
AT
A453
L1
i-Pr
Me
3,5-di-Cl—Ph
AN
A454
L1
i-Pr
Me
3,5-di-Cl—Ph
AU
419
L1
i-Pr
Cl
3,5-di-Cl—Ph
A
397-0
L1
OCH 2 CH═CH 2
Me
3,5-di-Cl—Ph
A
A455
L1
i-Pr
Me
3,5-di-Cl—Ph
AW
A456
L1
i-Pr
Me
3,5-di-Cl—Ph
AX
A457
L1
i-Pr
Me
3,5-di-Cl—Ph
AY
A458
L1
i-Pr
Me
3,5-di-Cl—Ph
AZ
395
L1
—OCHF 2
Me
3,5-di-Cl—Ph
A
A459
L1
Me
3,5-di-Cl—Ph
A
A464
L1
—N(CH 3 ) 2
Me
2,6-di-Cl-4-F—Ph
A
A462
L1
—N(CH 3 ) 2
Me
2,4,6-tri-F—Ph
A
A463
L1
—N(CH 3 ) 2
Me
2,3-di-Cl-5-F—Ph
A
A460
L1
—N(CH 3 ) 2
Me
2,3,5-tri-F—Ph
A
A461
L1
—N(CH 3 ) 2
Me
2,3,5-tri-Cl—Ph
A
558
L1
i-Pr
—C(O)CH 3
3,5-di-Cl—Ph
A.
32. A veterinary composition comprising the compound of claim 1 or a pharmaceutically or a veterinarily acceptable salt thereof and a veterinarily acceptable carrier.
33. A veterinary composition comprising the compound of claim 1 or a pharmaceutically or a veterinarily acceptable salt thereof, one or more additional active agent(s), and a veterinarily acceptable carrier.
34. A method for the treatment, control and/or prevention of a parasitic infection or infestation in an animal in need thereof, which comprises administering to said animal an effective amount of the compound of claim 1 , or a pharmaceutically or a veterinarily acceptable salt thereof.
35. A compound having the formula:
or a pharmaceutically acceptable salt thereof.
36. A compound of the formula
37. The compound according to claim 35 having the formula
38. A compound of the formula
39. A compound of the formula
40. A compound of the formula
41. A compound of the formula