IP Library › Granted Patent US 12,503,474
Granted Patent B2
US 12,503,474 · App. 18/622,428 · Granted Dec 23, 2025

Substituted pyrrolo[1,2-b]pyridazines as anthelmintics

Inventors: Hannes Fiepko Koolman (Biberach an der Riss, DE); Bart Herlé (Biberach an der Riss, DE)
C07D487/04C07D491/052C07D513/04
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Quick Facts
Patent No.
US 12,503,474
App. No.
18/622,428
Granted
Dec 23, 2025
Kind
B2
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 (161)

1 . A method for the prevention, control, and/or treatment of a parasitic infection in an animal in need thereof, wherein the method comprises administering to the animal an effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt or stereoisomer thereof,

wherein:

each is independently a single bond or double bond;

R 1 is H, halogen, CN, alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), Si(alkyl) 3 , NR a R b , OH, O(alkyl), O(alkenyl), O(alkynyl), OSi(alkyl) 3 , O(aryl), SF 5 , S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , 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) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;

R 1 ′ is H, halogen, alkyl, or haloalkyl;

R 2 is H, halogen, CN, alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), NR a R b , OH, O(alkyl), O(aryl), SF 5 , S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), O(alkyl), O(aryl), S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;

R 3 is H, halogen, CN, alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), NR a R b , OH, O(alkyl), O(aryl), SF 5 , S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl, wherein the alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), O(alkyl), O(aryl), S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkenyl, cycloalkoxy, heterocyclyl, aryl, or heteroaryl is optionally substituted with one or more independently selected substituents;

R 4 is H, alkyl, alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), NR a R b , SF 5 , S(O) p alkyl, S(O) p haloalkyl, 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)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, or 5- to 10-membered heteroaryl is optionally substituted with one or more independently selected substituents;

each R a is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;

each R b is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents; or

any R a and R b , 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), (L11), (L12), (L13), (L14), (L15), (L16), or (L17):

—C(X)NR′-(L1), —NR′C(X)-(L2), —NR′C(X)NR′-(L3), —S(NR′) (O)CH 2 -(L4), —CH 2 S(NR′) (O)-(L5), —S(O) 2 NR′-(L6), —NR'S(O) 2 -(L7), —S(O) 2 CH 2 -(L8), —CH 2 S(O) 2 -(L9), —CH(CF 3 )NR′-(L10), —NR′CH(CF 3 )-(L11), —CH(CHF 2 )NR′-(L12), —NR′CH(CHF 2 )-(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;

Y 1 is C, CR 5 , or N;

Y 2 is CR 5 , —CR 5 R 5 ′—, N, —NR′—, —O—, or —S—;

Y 3 is CR 5 , —CR 5 R 5 ′—, N, —NR′—, —O—, or —S—;

Y 4 is CR 5 , —CR 5 R 5 ′—, N, —NR′—, —O—, or —S—;

Y 5 is CR 5 , —CR 5 R 5 ′—, N, —NR′—, —O—, or —S—;

Y 6 is C, CR 5 , or N;

W is absent, CR 6 , —CR 6 R 7 —, N, —NR 8 —, —O—, or —S(O) p —;

W 1 is CR 6 , —CR 6 R 7 , N, —NR 8 —, —O—, or —S(O) p —;

Z is CR 7 , —CR 6 R 7 —, N, —NR 8 —, —O—, or —S(O) p —;

Q is CR 9 or N;

each R 5 is independently H, halogen, CN, NO 2 , alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), NR c R d , NHC(O)alkyl, OH, O(alkyl), OC(O)alkyl, SF 5 , S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkoxy, aryl, or heteroaryl, wherein each alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), NHC(O)alkyl, O(alkyl), OC(O)alkyl S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkoxy, aryl, and heteroaryl is optionally and independently substituted with one or more independently selected substituents;

each R 5 ′ is independently H, halogen, CN, NO 2 , alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), NR c R d , NHC(O)alkyl, OH, O(alkyl), OC(O)alkyl, SF 5 , S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkoxy, aryl, or heteroaryl, wherein each alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, C(O)alkyl, C(O)NH 2 , C(O)NH(alkyl), C(O)N(alkyl) 2 , C(O)O(alkyl), NHC(O)alkyl, O(alkyl), OC(O)alkyl, S(O) p alkyl, S(O) p haloalkyl, cycloalkyl, cycloalkoxy, aryl, and heteroaryl is optionally and independently substituted with one or more independently selected substituents; or

any R 5 and R 5 ′, 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 carbocyclyl or heterocyclyl;

wherein each 3- to 7-membered carbocyclyl or heterocyclyl 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 carbocyclyl or heterocyclyl is optionally and independently substituted with one or more independently selected substituents;

each R c is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;

each R d is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents; or

any R c and R d , 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 R 6 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 R 7 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 R 6 and R 7 , 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 carbocyclyl or heterocyclyl;

wherein each 3- to 7-membered carbocyclyl or heterocyclyl 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 carbocyclyl or heterocyclyl is optionally and independently substituted with one or more independently selected substituents;

R 8 is H or C 1 -C 4 alkyl;

R 9 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, NO 2 , alkyl, haloalkyl, CH(NH), CH(NOH), C(NH)NH 2 , C(O)alkyl, C(O)haloalkyl, C(O)NH 2 , 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)SR, C(S)NH 2 , Si(R) 3 , NH 2 , NH(alkyl), NHC(NH)NH 2 , NHNH 2 , NH(aryl), N(alkyl) 2 , N (aryl) 2 , OH, O(alkyl), O(haloalkyl), OSi(R) 3 , O(aryl), ═O, SH, SF 5 , S(alkyl), S(haloalkyl), S(O)alkyl, S(O)haloalkyl, S(O) 2 alkyl, S(O) 2 haloalkyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl, and heteroaryl; and

each R is independently alkyl, haloalkyl, or aryl;

with the proviso that no more than three of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 are heteroatoms.

2 . The method of claim 1 , wherein:

(a) the method is for preventing a parasitic infection in an animal in need thereof; and

(b) the parasitic infection is caused by Dirofilaria immitis.

3 . The method of claim 1 , wherein the compound is of Formula (IA):

or a pharmaceutically acceptable salt or stereoisomer thereof,

wherein:

each is independently a single bond or double bond;

R 1 is H, halogen, CN, alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, NR a R b , O(alkyl), O(alkenyl), O(alkynyl), cycloalkyl, cycloalkenyl, or heterocyclyl, wherein the alkyl, alkyl-NH 2 , 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;

R 1 ′ is H, halogen, alkyl, or haloalkyl;

R 2 is H, halogen, CN, alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, OH, or O(alkyl), wherein the alkyl, alkyl-NH 2 , 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;

R 3 is H, halogen, CN, alkyl, alkyl-NH 2 , alkyl-NH(alkyl), alkyl-N(alkyl) 2 , alkyl-O(alkyl), alkenyl, alkynyl, OH, or O(alkyl), wherein the alkyl, alkyl-NH 2 , 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;

R 4 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;

each R a is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents;

each R b is independently H or alkyl, wherein each alkyl is optionally and independently substituted with one or more independently selected substituents; or

any R a and R b , 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), (L6), (L7), (L16), or (L17):

C(X)NR′-(L1), —NR′C(X)-(L2), —S(O) 2 NR′-(L6), —NR'S(O) 2 -(L7),

each X is independently NR′, O, or S;

R′ is H, alkyl, haloalkyl, or aralkyl, wherein the alkyl, haloalkyl, or aralkyl is optionally substituted with one or more independently selected substituents;

Y 1 is C or N;

Y 2 is CR 5 or N;

Y 3 is CR 5 or N;

Y 4 is CR 5 or N;

Y 5 is CR 5 or N;

Y 6 is C or N;

W is absent, CR 6 , or —CR 6 R 7 —;

W 1 is CR 6 or —CR 6 R 7 —;

Z is CR 7 , —CR 6 R 7 —, or —O—;

Q is CR 9 or N;

each R 5 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 R 5 ′ 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 R 6 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 R 7 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 R 6 and R 7 , 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 carbocyclyl or heterocyclyl;

wherein each 3- to 7-membered carbocyclyl or heterocyclyl 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 carbocyclyl or heterocyclyl is optionally and independently substituted with one or more independently selected substituents;

R 9 is H, halogen, alkyl, or haloalkyl;

wherein each optional substituent is independently selected from the group consisting of halogen, CN, alkyl, haloalkyl, C(O)alkyl, C(O)haloalkyl, C(O)NH 2 , 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)NH 2 , Si(R) 3 , NH 2 , NH(alkyl), N(alkyl) 2 , OH, O(alkyl), O(haloalkyl), OSi(R) 3 , SH, SF 5 , S(alkyl), S(haloalkyl), S(O)alkyl, S(O) 2 alkyl, S(O) 2 haloalkyl, and cycloalkyl; and

each R is independently alkyl, haloalkyl, or aryl;

with the proviso that no more than three of Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , and Y 6 are N.

4 . The method of claim 1 , wherein L is (L1) or (L2):

—C(X)NR′-(L1) or —NR′C(X)-(L2).

5 . The method of claim 1 , wherein each X is independently O or S.

6 . The method of claim 1 , wherein:

W is —CR 6 R 7 —;

W 1 is —CR 6 R 7 —; and

Z is —O—.

7 . The method of claim 1 , wherein Q is CR 9 .

8 . The method of claim 1 , wherein Q is N.

9 . The method of claim 1 , 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:

10 . The method of claim 1 , wherein the compound is of Formula (Ie):

or a pharmaceutically acceptable salt or stereoisomer thereof,

wherein:

is a single bond or double bond;

W is absent or —CR 6 R 7 —;

each R 10 is independently halogen, CN, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C(O)C 1 -C 6 alkyl, C(O)C 1 -C 6 haloalkyl, C(O)NH 2 , C(O)NH(C 1 -C 6 alkyl), C(O)NH(C 1 -C 6 haloalkyl), C(O)N(C 1 -C 6 alkyl) 2 , C(O)N(C 1 -C 6 haloalkyl) 2 , C(O)O(C 1 -C 6 alkyl), C(O)O(C 1 -C 6 haloalkyl), NH 2 , NH(C 1 -C 6 alkyl), N(C 1 -C 6 alkyl) 2 , OH, O(C 1 -C 4 alkyl), O(C 1 -C 4 haloalkyl), O(phenyl), SF 5 , S(C 1 -C 6 alkyl), S(C 1 -C 6 haloalkyl), S(O)C 1 -C 6 alkyl, S(O)C 1 -C 6 haloalkyl, S(O) 2 C 1 -C 6 alkyl, S(O) 2 C 1 -C 6 haloalkyl, C 3 -C 8 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.

11 . The method of claim 10 , wherein:

each R 10 is independently halogen; and

m is 2 or 3.

12 . The method of claim 10 , wherein:

R 1 is C 1 -C 4 alkyl or NR a R b ;

R 1 ′ is H;

R 2 is H, halogen, C 1 -C 3 alkyl, or C 1 -C 3 haloalkyl;

R 3 is H, halogen, C 1 -C 3 alkyl, or C 1 -C 3 haloalkyl;

W is —CH 2 —;

W 1 is —CH 2 —;

Z is —O—;

each R 10 is independently F or C 1 ; and

m is 2 or 3.

13 . The method of claim 12 , wherein:

R 1 is C 1 -C 4 alkyl or NR a R b ;

R 2 is H;

R 3 is halogen or C 1 -C 3 alkyl; and

14 . The method of claim 13 , wherein R 1 is CH(CH 3 ) 2 , C(CH 3 ) 3 , N(CH 3 ) 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 CH 3 .

15 . The method of claim 13 , wherein:

Y 2 is CR 5 ;

Y 3 is CR 5 ;

Y 4 is CR 5 ; and

Y 5 is CR 5 .

16 . A method for the prevention, control, and/or treatment of a parasitic infection in an animal in need thereof, wherein the method comprises administering to the animal an effective amount of a compound selected from the group consisting of A461-A524, A527-A529, A531-A533, A535, A536 a , A536 b , A537-A560, A568, and A569:

or a pharmaceutically acceptable salt thereof.

17 . The method of claim 16 , wherein:

(a) the method is for preventing a parasitic infection in an animal in need thereof; and

(b) the parasitic infection is caused by Dirofilaria immitis.

18 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

19 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

20 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

21 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

22 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

23 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

24 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

25 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

26 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

27 . The method of claim 16 , wherein the compound is:

or a pharmaceutically acceptable salt thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2024
From: HERLÉ, BART; KOOLMAN, HANNES FIEPKO
To: BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG
Reel/Frame 068593/0436 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2024
From: BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG
To: BOEHRINGER INGELHEIM VETMEDICA GMBH
Reel/Frame 068594/0582 →
Continuity (3)
Division 18050567 · Oct 28, 2022
Provisional Application 63263367 · Nov 1, 2021
Related Publication 20240254133A1 · Aug 1, 2024
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