# US 11,999,742 B2 · Substituted pyrrolo[1,2-b]pyridazines as anthelmintics

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- Number: US 11,999,742 B2
- Document ID: US11999742B2
- Status: Granted
- Kind: B2
- Application number: 18/050,567
- Filed: 2022-10-28
- Published: 2023-05-25
- Granted: 2024-06-04
- Earliest claimed: 2021-11-01
- Applicants: Boehringer Ingelheim Vetmedica GmbH
- Inventors: Hannes Fiepko Koolman; Bart Herlé
- Web page: https://patentgrep.com/patent/US11999742B2

## CPC

- C07D 487/04: Ortho-condensed systems
- C07D 491/052: the oxygen-containing ring being six-membered
- C07D 513/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

This invention provides for compounds of the formula: wherein the variables are defined herein, or salt thereof, compositions comprising these compounds, and methods for the treatment, control and/or prevention of a parasitic infestation and/or infection in an animal in need thereof by administering an effective amount of these compounds to said animal.

## Claims

### Claim 1

A compound of Formula (I):
or a pharmaceutically acceptable salt or stereoisomer thereof,
wherein:
each independently is a single or double bond;
R1 is H, halogen, CN, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), Si(alkyl)3, NRaRb, OH, O(alkyl), O(alkenyl), O(alkynyl), OSi(alkyl)3, O(aryl), SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), Si(alkyl)3, O(alkyl), O(alkenyl), O(alkynyl), O(aryl), OSi(alkyl)3, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;
R1′ is H, halogen, alkyl, or haloalkyl;
R2 is H, halogen, CN, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRaRb, OH, O(alkyl), O(aryl), SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), O(alkyl), O(aryl), S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;
R3 is H, halogen, CN, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRaRb, OH, O(alkyl), O(aryl), SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), O(alkyl), O(aryl), S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;
R4 is H, alkyl, alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRaRb, SF5, S(O)palkyl, cycloalkyl, cycloalkenyl, carbocyclyl-(spirocyclic carbocyclyl), carbocyclyl-(spirocyclic heterocyclyl), heterocyclyl, heterocyclyl-(spirocyclic carbocyclyl), heterocyclyl-(spirocyclic heterocyclyl), aryl, or 5- to 10-membered heteroaryl, wherein the alkyl, alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), S(O)palkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or 5- to 10-membered heteroaryl is optionally substituted with one or more independently selected substituents;
each Ra is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;
each Rb is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents; or
any Ra and Rb, taken together with the nitrogen atom to which they are attached, independently forms a 3- to 8-membered heterocyclyl;
wherein each 3- to 8-membered heterocyclyl independently contains 0, 1, 2, or 3 additional heteroatoms independently selected from the group consisting of N, O, Si, and S; and
wherein each 3- to 8-membered heterocyclyl is optionally and independently substituted with one or more independently selected substituents;
L is (L1), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L 11), (L12), (L13), (L14), (L15), (L16), or (L17):
—C(X)NR′-(L1), —NR′C(X)-(L2), —NR′C(X)NR′-(L3), —S(NR′)(O)CH2-(L4), —CH2S(NR′)(O)-(L5), —S(O)2NR′-(L6), —NR′S(O)2-(L7), —S(O)2CH2-(L8), —CH2S(O)2-(L9), —CH(CF3)NR′-(L10), —NR′CH(CF3)-(L11), —CH(CHF2)NR′-(L12), —NR′CH(CHF2)-(L13),
each X is independently NR′, O, or S;
R′ is H, alkyl, haloalkyl, cycloalkyl, aralkyl, or aryl, wherein the alkyl, haloalkyl, cycloalkyl, aralkyl, or aryl is optionally substituted with one or more independently selected substituents; or
two R′, together with the atoms to which they are attached, form a 2- to 4-membered carbon chain resulting in a 5- to 7-membered heterocyclyl;
Y1 is C, CR5, or N;
Y2 is CR5, —CR5R5′—, N, —NR′—, —O—, or —S—;
Y3 is CR5, —CR5R5′—, N, —NR′—, —O—, or —S—;
Y4 is CR5, —CR5R5′—, N, —NR′—, —O—, or —S—;
Y5 is CR5, —CR5R5′—, N, —NR′—, —O—, or —S—;
Y6 is C, CR5, or N;
W is absent, CR6, —CR6R7—, N, —NR′—, —O—, or —S(O)p—;
W1 is CR6, —CR6R7—, N, —NR′—, —O—, or —S(O)p—;
Z is CR7, —CR6R7—, N, —NR′—, —O—, or —S(O)p—;
Q is CR9;
each R5 is independently H, halogen, CN, NO2, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRcRd, NHC(O)alkyl, OH, O(alkyl), OC(O)alkyl, SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkoxy, aryl, or heteroaryl, wherein each alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), O(alkyl), S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkoxy, aryl, and heteroaryl is optionally and independently substituted with one or more independently selected substituents;
each R5′ is independently H, halogen, CN, NO2, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), NRcRd, NHC(O)alkyl, OH, O(alkyl), OC(O)alkyl, SF5, S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkoxy, aryl, or heteroaryl, wherein each alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH2, C(O)NH(alkyl), C(O)N(alkyl)2, C(O)O(alkyl), O(alkyl), S(O)palkyl, S(O)phaloalkyl, cycloalkyl, cycloalkoxy, aryl, and heteroaryl is optionally and independently substituted with one or more independently selected substituents; or
any R5 and R5′, taken together with the carbon atom to which they are attached, independently forms a 2- to 6-membered chain resulting in a 3- to 7-membered cyclyl;
wherein each 3- to 7-membered cyclyl optionally and independently contains 1 or 2 heteroatoms independently selected from the group consisting of N, O, Si, and S; and
wherein each 3- to 7-membered cyclyl is optionally and independently substituted with one or more independently selected substituents;
each Rc is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;
each Rd is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents; or
any Rc and Rd, taken together with the nitrogen atom to which they are attached, independently forms a 3- to 8-membered heterocyclyl;
wherein each 3- to 8-membered heterocyclyl independently contains 0, 1, 2, or 3 additional heteroatoms independently selected from the group consisting of N, O, Si, and S; and
wherein each 3- to 8-membered heterocyclyl is optionally and independently substituted with one or more independently selected substituents;
each R6 is independently H, halogen, alkyl, alkenyl, alkynyl, O(alkyl), cycloalkyl, or cycloalkoxy, wherein each alkyl, alkenyl, alkynyl, O(alkyl), cycloalkyl, and cycloalkoxy is optionally and independently substituted with one or more independently selected substituents;
each R7 is independently H, halogen, alkyl, alkenyl, alkynyl, O(alkyl), cycloalkyl, or cycloalkoxy, wherein each alkyl, alkenyl, alkynyl, O(alkyl), cycloalkyl, and cycloalkoxy is optionally and independently substituted with one or more independently selected substituents; or
any R6 and R7, taken together with the carbon atom to which they are attached, independently forms a 2- to 6-membered chain resulting in a 3- to 7-membered cyclyl;
wherein each 3- to 7-membered cyclyl optionally and independently contains 1 or 2 heteroatoms independently selected from the group consisting of N, O, Si, and S; and
wherein each 3- to 7-membered cyclyl is optionally and independently substituted with one or more independently selected substituents;
R8 is H or C1-C4 alkyl;
R9 is H, halogen, alkyl, haloalkyl, alkenyl, alkynyl, or cycloalkyl;
each p is independently 0, 1, or 2; and
q is 0 or 1;
wherein each optional substituent is independently selected from the group consisting of halogen, CN, NO2, alkyl, haloalkyl, CH(NH), CH(NOH), C(NH)NH2, C(O)alkyl, C(O)haloalkyl, C(O)NH2, C(O)NH(alkyl), C(O)NH(haloalkyl), C(O)N(alkyl)2, C(O)N(haloalkyl)2, C(O)OH, C(O)O(alkyl), C(O)O(haloalkyl), C(O)OC(O)R, C(O)SR, C(S)NH2, Si(R)3, NH2, NH(alkyl), NHC(NH)NH2, NHNH2, NH(aryl), N(alkyl)2, N(aryl)2, OH, O(alkyl), O(haloalkyl), OC(O)NH2, OC(O)OR, OSi(R)3, OP(O)(OR)(OR), OS(O)2OH, O(aryl), ═O, P(R)3, P(O)R, P(O)(R)2, P(O)(OR)(OR), P(O)(OR)NH2, SH, SF5, S(alkyl), S(haloalkyl), S(O)alkyl, S(O)haloalkyl, S(O)(NH)R, S(O)2alkyl, S(O)2haloalkyl, S(O)2NH2, S(O)2OH, S(O)2O(alkyl), cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl; and
each R is independently alkyl, haloalkyl, or aryl;
with the proviso that no more than three of Y1, Y2, Y3, Y4, Y5, and Y6 are heteroatoms.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein the compound is of Formula (IA):
or a pharmaceutically acceptable salt or stereoisomer thereof,
wherein:
each independently is a single or double bond;
R1 is H, halogen, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, NRaRb, O(alkyl), O(alkenyl), O(alkynyl), cycloalkyl, cycloalkenyl, or heterocyclyl, wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, O(alkyl), O(alkenyl), O(alkynyl), cycloalkyl, cycloalkenyl, or heterocyclyl is optionally substituted with one or more independently selected substituents;
R2 is H, halogen, CN, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, OH, or O(alkyl), wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, or O(alkyl) is optionally substituted with one or more independently selected substituents;
R3 is H, halogen, CN, alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, OH, or O(alkyl), wherein the alkyl, alkyl-NH2, alkyl-NH(alkyl), alkyl-N(alkyl)2, alkyl-O(alkyl), alkenyl, alkynyl, or O(alkyl) is optionally substituted with one or more independently selected substituents;
R4 is cycloalkyl, cycloalkenyl, heterocyclyl, phenyl, or 5- or 6-membered heteroaryl, wherein the cycloalkyl, cycloalkenyl, heterocyclyl, phenyl, or 5- or 6-membered heteroaryl is optionally substituted with one or more independently selected substituents;
L is (L1), (L2), (L6), (L7), (L16), or (17):
—C(X)NR′-(L1), —NR′C(X)-(L2), —S(O)2NR′-(L6), —NR′S(O)2-(L7),
R′ is H, alkyl, haloalkyl, or aralkyl, wherein the alkyl, haloalkyl, or aralkyl is optionally substituted with one or more independently selected substituents; or
Y1 is C or N;
Y2 is CR5 or N;
Y3 is CR5 or N;
Y4 is CR5 or N;
Y5 is CR5 or N;
Y6 is C or N;
W is absent, CR6, or —CR6R7—;
W1 is CR6 or —CR6R7—;
Z is CR7, —CR6R7—, or —O—;
each R5 is independently H, halogen, CN, alkyl, alkenyl, alkynyl, or O(alkyl), wherein each alkyl, alkenyl, alkynyl, and O(alkyl) is optionally and independently substituted with one or more independently selected substituents;
each R5 is independently H, halogen, CN, alkyl, alkenyl, alkynyl, or O(alkyl), wherein each alkyl, alkenyl, alkynyl, and O(alkyl) is optionally and independently substituted with one or more independently selected substituents;
each R6 is independently H, halogen, alkyl, alkenyl, alkynyl, or O(alkyl), wherein each alkyl, alkenyl, alkynyl, and O(alkyl) is optionally and independently substituted with one or more independently selected substituents;
each R7 is independently H, halogen, alkyl, alkenyl, alkynyl, or O(alkyl), wherein each alkyl, alkenyl, alkynyl, and O(alkyl) is optionally and independently substituted with one or more independently selected substituents; or
any R6 and R7, taken together with the carbon atom to which they are attached, independently forms a 2- to 6-membered chain resulting in a 3- to 7-membered cyclyl;
wherein each 3- to 7-membered cyclyl optionally and independently contains 1 or 2 heteroatoms independently selected from the group consisting of N, O, Si, and S; and
wherein each 3- to 7-membered cyclyl is optionally and independently substituted with one or more independently selected substituents; and
R9 is H, halogen, alkyl, or haloalkyl;
wherein each optional substituent is independently selected from the group consisting of halogen, CN, alkyl, haloalkyl, acyl, C(O)alkyl, C(O)haloalkyl, C(O)NH2, C(O)NH(alkyl), C(O)NH(haloalkyl), C(O)N(alkyl)2, C(O)N(haloalkyl)2, C(O)OH, C(O)O(alkyl), C(O)O(haloalkyl), C(S)NH2, Si(R)3, NH2, NH(alkyl), N(alkyl)2, OH, O(alkyl), O(haloalkyl), O(acyl), OSi(R)3, OS(O)2OH, SH, SF5, S(alkyl), S(haloalkyl), S(O)alkyl, S(O)2alkyl, S(O)2haloalkyl, S(O)2O(alkyl), and cycloalkyl.

### Claim 3 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein L is (L1) or (L2):
—C(X)NR′-(L1) or —NR′C(X)-(L2).

### Claim 4 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein each X is independently O or S.

### Claim 5 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
W is —CR6R7—;
W1 is —CR6R7—; and
Z is —O—.

### Claim 6 (depends on 1)

The compound according to claim 1, or a stereoisomer thereof, wherein the compound, or stereoisomer thereof, is of Formula (IA-1):
or a pharmaceutically acceptable salt thereof,
wherein:
is Ring System A, Ring System B, Ring System C, Ring System D, Ring System E, Ring System F, Ring System G, Ring System H, Ring System I, Ring System J, Ring System K, Ring System L, Ring System M, Ring System N, Ring System O, Ring System P, Ring System Q, Ring System R, Ring System S, Ring System T, Ring System U, Ring System V, Ring System W, Ring System X, Ring System Y, Ring System Z, Ring System AA, Ring System AB, Ring System AC, Ring System AD, or Ring System AE:

### Claim 7 (depends on 1)

The compound according to claim 1, wherein the compound is of Formula (Ie):
or a pharmaceutically acceptable salt or stereoisomer thereof,
wherein:
is a single or double bond;
W is absent or —CR6R7—;
each R10 is independently halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl, C(O)C1-C6 alkyl, C(O)C1-C6 haloalkyl, C(O)NH2, C(O)NH(C1-C6 alkyl), C(O)NH(C1-C6 haloalkyl), C(O)N(C1-C6 alkyl)2, C(O)N(C1-C6 haloalkyl)2, C(O)O(C1-C6 alkyl), C(O)O(C1-C6 haloalkyl), NH2, NH(C1-C6 alkyl), N(C1-C6 alkyl)2, OH, O(C1-C4 alkyl), O(C1-C4 haloalkyl), O(phenyl), SF5, S(C1-C6 alkyl), S(C1-C6 haloalkyl), S(O)C1-C6 alkyl, S(O)C1-C6 haloalkyl, S(O)2C1-C6 alkyl, S(O)2C1-C6 haloalkyl, C3-C5 cycloalkyl, 3- to 7-membered heterocyclyl, phenyl, or 5- or 6-membered heteroaryl, wherein each 3- to 7-membered heterocyclyl independently contains 1, 2, or 3 heteroatoms independently selected from the group consisting of N, O, Si, and S; and
m is 0, 1, 2, 3, 4, or 5.

### Claim 8 (depends on 7)

The compound according to claim 7, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
each R10 is independently halogen; and
m is 2 or 3.

### Claim 9 (depends on 7)

The compound according to claim 7, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
R1 is C1-C4 alkyl or NRaRb;
R2 is H, halogen, CN, C1-C3 alkyl or C1-C3 haloalkyl;
R3 is H, halogen, CN, C1-C3 alkyl or C1-C3 haloalkyl;
R′ is H,
W is —CH2—;
W1 is —CH2—;
Z is —O—;
each R10 is independently F or Cl; and
m is 2 or 3.

### Claim 10 (depends on 9)

The compound according to claim 9, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
R1 is C1-C4 alkyl or NRaRb;
R2 is H;
R3 is halogen or C1-C3 alkyl; and
is:

### Claim 11 (depends on 10)

The compound according to claim 10, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R1 is CH(CH3)2, C(CH3)3, N(CH3)2, or azetidin-1-yl, wherein the azetidin-1-yl is optionally substituted with one or more substituents independently selected from the group consisting of F and CH3.

### Claim 12 (depends on 11)

The compound according to claim 11, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R3 is Cl or CH3.

### Claim 13 (depends on 12)

The compound according to claim 12, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R1 is CH(CH3)2, C(CH3)3, or N(CH3)2.

### Claim 14 (depends on 13)

The compound according to claim 13, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
Y2 is CR5;
Y3 is CR5;
Y4 is CR5;
Y5 is CR5; and
each R5 is independently H.

### Claim 15 (depends on 9)

The compound according to claim 9, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
(a) Y2 is N;
Y3 is CR5;
Y4 is CR5; and
Y5 is CR5; or
(b) Y2 is CR5;
Y3 is N;
Y4 is CR5; and
Y5 is CR5; or
(c) Y2 is CR5;
Y3 is CR5;
Y4 is N; and
Y5 is CR5; or
(d) Y2 is CR5;
Y3 is CR5;
Y4 is CR5; and
Y5 is N; or
(e) Y2 is CR5;
Y3 is N;
Y4 is N; and
Y5 is CR5; or
(f) Y2 is CR5;
Y3 is N;
Y4 is CR5; and
Y5 is N; or
(g) Y2 is CR5;
Y3 is CR5;
Y4 is N; and
Y5 is N; or
(h) Y2 is N;
Y3 is N;
Y4 is CR5; and
Y5 is CR5; or
(i) Y2 is N;
Y3 is CR5;
Y4 is N; and
Y5 is CR5.

### Claim 16 (depends on 9)

The compound according to claim 9, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein:
Y2 is CR5;
Y3 is CR5;
Y4 is CR5; and
Y5 is CR5.

### Claim 17 (depends on 1)

A veterinary composition comprising a pharmaceutically acceptable carrier and the compound according to claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof.

### Claim 18 (depends on 17)

The veterinary composition according to claim 17, wherein the veterinary composition further comprises one or more additional active agents.

### Claim 19

A compound or a stereoisomer thereof, wherein the compound, or stereoisomer thereof, is selected from the group consisting of:
or a pharmaceutically acceptable salt thereof.

### Claim 20 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 21 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 22 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 23 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 24 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 25 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 26 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 27 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 28 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 29 (depends on 19)

The compound according to claim 19, wherein the compound is:

### Claim 30 (depends on 19)

A veterinary composition comprising a pharmaceutically acceptable carrier and the compound according to claim 19, or a pharmaceutically acceptable salt or stereoisomer thereof.

### Claim 31 (depends on 30)

The veterinary composition according to claim 30, wherein the veterinary composition further comprises one or more additional active agents.