IP Library › Granted Patent US 12,312,356

Granted Patent B2

US 12,312,356 · App. 18/421,660 · Granted May 27, 2025

Anthelmintic heterocyclic compounds

Inventors: Hannes Fiepko Koolman (Biberach an der Riss, DE); Bart Herlé (Biberach an der Riss, DE); Alan Long (Biberach an der Riss, DE)

C07D487/04 A61P33/10

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Quick Facts

Patent No.: US 12,312,356
App. No.: 18/421,660
Granted: May 27, 2025
Kind: B2

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Abstract

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.

Claims (956)

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

wherein:

L is L1 or L2:

R′ is hydrogen or optionally substituted alkyl;

R 1 is optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted alkenyloxy, optionally substituted alkoxyalkyl, optionally substituted aminoalkyl, optionally substituted alkylaminoalkyl, optionally substituted dialkylaminoalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, 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, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, or optionally substituted dialkylaminocarbonyl;

R 3 is optionally substituted 6- to 10-membered aryl or optionally substituted 5- to 10-membered heteroaryl;

R 4 is independently in each occurrence hydrogen, halogen, cyano, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkylcarbonyl, optionally substituted alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted alkylaminocarbonyl, optionally substituted di(alkyl)aminocarbonyl, optionally substituted alkylcarbonyloxy or optionally substituted alkylcarbonylamino;

R 5 and R 6 are independently in each occurrence hydrogen or C 1 -C 4 -alkyl;

R 7 is hydrogen or C 1 -C 4 -alkyl;

R 8 is hydrogen or optionally substituted alkyl;

R 9 and R 9′ are independently hydrogen or C 1 -C 4 -alkyl; 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 C—R 8 ;

X is O;

Y 1 and Y 6 are each independently N or C;

Y 2 , Y 3 , Y 4 and Y 5 are each independently N, S or —CR 4 —;

W is CR 5 R 6 ,

Z is CR 5 R 6 , O, SO p , or N—R 7 ; 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;

wherein each optional substituent is independently selected from the group consisting of halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano, hydroxyl, amino, C 1 -C 6 -alkylamino, C 1 -C 6 -dialkylamino, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, thiol, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl.

2. The method of claim 1 , wherein R 3 is optionally substituted phenyl or optionally substituted pyridyl.

3. The method of claim 1 , wherein the compound of Formula (I) is a compound of formula (Ie):

wherein:

R 1 is 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, 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 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 or C 1 -C 4 -haloalkyl;

each R 4 is independently hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;

R 5 and R 6 are independently hydrogen, or C 1 -C 3 -alkyl;

R′ is hydrogen or C 1 -C 3 -alkyl;

R 8 is hydrogen;

R 9 and R 9′ are independently hydrogen or C 1 -C 3 -alkyl;

each R 10 is independently halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -haloalkoxy;

Z is CR 5 R 6 or O;

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.

4. The method according to claim 3 , wherein each R 10 is independently halogen and m is 2 or 3.

5. The method according to claim 3 , wherein each R 10 is independently chloro or fluoro; and

m is 2 or 3.

6. The method of claim 3 , wherein:

R′ is hydrogen;

each R 4 is independently hydrogen, halogen or cyano;

R 5 and R 6 are independently hydrogen or C 1 -C 3 -alkyl;

R 9 and R 9′ are independently hydrogen or C 1 -C 3 -alkyl;

each R 10 is independently halogen;

W is CH 2 ;

Z is O;

Y 2 , Y 3 , Y 4 , Y 5 are independently CR 4 or N;

a is 0 or 1; and

m is 2 or 3.

7. The method according to claim 6 , wherein:

R 1 is C 1 -C 4 -alkyl, hydroxy-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; and

each R 10 is independently chloro or fluoro.

8. The method according to claim 7 , wherein:

R 1 is C 1 -C 4 -alkyl or hydroxy-C 1 -C 4 -alkyl;

R 2 is C 1 -C 3 -alkyl.

9. The method according to claim 7 , wherein:

R 1 is —NR a R b ;

R a and R b are independently H or C 1 -C 4 -alkyl; or R a and R b form, with the nitrogen to which they are attached, a 3-, 4-, 5- or 6-membered heterocyclyl group, which may include one or two additional heteroatoms selected from the group consisting of N, O and S and is optionally substituted with one or more halogen, hydroxyl or C 1 -C 3 -alkyl; and

R 2 is C 1 -C 3 -alkyl.

10. The method according to claim 9 , wherein:

R a and R b are independently C 1 -C 3 -alkyl.

11. The method according to claim 9 , wherein:

R a and R b form with the nitrogen to which they are attached a 3-, 4-, 5- or 6-membered ring which is optionally substituted with one or more halogen, hydroxyl or C 1 -C 3 -alkyl.

12. A method for the treatment, control and/or prevention of an endoparasitic infection in an animal in need thereof, which comprises administering to said animal an effective amount of 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

or is hydrogen;

Cmpd.

Ring

R 1

R 2

R 3

System

271

i-Pr

3,5-di-Cl—Ph

326

i-Pr

327

i-Pr

326-0

i-Pr

324

i-Pr

325

i-Pr

323

i-Pr

t-Bu

175

i-Pr

3,5-di-F—Ph

A407

i-Pr

2,6-di-F—Ph

A406

i-Pr

2,6-di-Cl—Ph

A413

i-Pr

2,4-di-F—Ph

A408

3,5-di-Cl—Ph

A412

i-Pr

4-F—Ph

A410

i-Pr

3-Cl-4-F—Ph

A411

i-Pr

3,5-di-Cl—Ph

A409

—N(CH 3 ) 2

3,5-di-Cl—Ph

A414

i-Pr

3,5-di-Cl—Ph

306

t-Bu

3,5-di-Cl—Ph

297

t-Bu

3,5-di-Cl—Ph

365

i-Pr

cyclopropyl

371

i-Pr

370

i-Pr

366

i-Pr

cyano

369

i-Pr

308

prop-1-en-2-

3,5-di-Cl—Ph

364

i-Pr

3,5-di-Cl—Ph

352

i-Pr

3,5-di-Cl—Ph

320-0

i-Pr

3,5-di-F—Ph

345

i-Pr

2,3,5-tri-F—Ph

344

i-Pr

2,3,5-tri-F—Ph

294

i-Pr

3,5-di-Cl—Ph

320

i-Pr

3,5-di-F—Ph

277

2-F-prop-2-

3,5-di-F—Ph

323-0

i-Pr

—CH 2 CH(CH 3 ) 2

298-0

t-Bu

CF 3

3-Cl—Ph

299-0

t-Bu

CF 3

3-Cl—Ph

299

t-Bu

CF 3

3,5-di-Cl—Ph

298

t-Bu

CF 3

3,5-di-Cl—Ph

304-0

i-Pr

3,5-di-

Cl—Ph

321

i-Pr

4-F—Ph

3,5-di-F—Ph

322

i-Pr

304

i-Pr

3,5-di-Cl—Ph

307

prop-1-en-2-

3,5-di-F—Ph

296

i-Pr

CF 3

3,5-di-Cl—Ph

295

i-Pr

CF 3

3,5-di-Cl—Ph

293

i-Pr

2,3-di-Cl—Ph

276

i-Pr

CF 3

3,5-di-F—Ph

274

i-Pr

2,3-di-Cl—Ph

273

i-Pr

3-F—Ph

272

i-Pr

3-Cl-5-F—Ph

275

i-Pr

3,5-di-F—Ph

279

prop-1-en-2-

3,5-di-F—Ph

174

2,6-di-F—Ph

A400

1,1-

3,5-di-Cl—Ph

difluoroethyl

A401

CF 3

3,5-di-Cl—Ph

373

i-Pr

372-0

i-Pr

A402

i-Pr

3,5-di-Cl—Ph

A403

i-Pr

—CH 2 OH

3,5-di-Cl—Ph

A404

i-Pr

—CF 2 CF 3

3,5-di-Cl—Ph

394

—OCH 3

3,5-di-Cl—Ph

398

—OCH 2 CH 3

3,5-di-Cl—Ph

A405

—CHF 2

3,5-di-Cl—Ph

573

t-Bu

2,3,5-tri-F—Ph

559

i-Pr

—CN

3,5-di-Cl—Ph

614

t-Bu

3,5-di-Cl—Ph

AAA,

451

—N(CH 3 ) 2

CF 3

3,5-di-Cl—Ph

572

t-Bu

2,5-di-Cl-4-F—Ph

528

i-Pr

2,5-di-Cl-4-F—Ph

571

t-Bu

2,4,5-tri-F—Ph

574

t-Bu

2,3-di-Cl-5-F—Ph

A415

i-Pr

3,5-di-Cl—Ph

A416

i-Pr

3,5-di-Cl—Ph

A417

i-Pr

3,5-di-Cl—Ph

A418

i-Pr

3,5-di-Cl—Ph

A419

i-Pr

3,5-di-Cl—Ph

A420

i-Pr

3,5-di-Cl—Ph

560

i-Pr

—CHF 2

3,5-di-Cl—Ph

305

i-Pr

—CHF 2

3,5-di-Cl—Ph

A421

2,6-di-Cl-4-F

A422

2,3,5-tri-F—Ph

420

t-Bu

3,5-di-Cl—Ph

A423

i-Pr

3,5-di-Cl—Ph

A424

i-Pr

3,5-di-Cl—Ph

523

t-Bu

2,6-di-Cl-4-F—Ph

A425

i-Pr

3,5-di-Cl—Ph

A426

i-Pr

3,5-di-Cl—Ph

526

t-Bu

2,3-di-Cl-5-F—Ph

527

i-Pr

2,4,6-tri-F—Ph

524

t-Bu

2,4,6-tri-F—Ph

525

t-Bu

2,3,5-tri-F—Ph

414-0

i-Pr

3,5-di-Cl—Ph

514

i-Pr

3,5-di-Cl—Ph

A427

i-Pr

3,5-di-Cl—Ph

A428

i-Pr

3,5-di-Cl—Ph

A429

i-Pr

3,5-di-Cl—Ph

A430

i-Pr

3,5-di-Cl—Ph

418

t-Bu

3,5-di-Cl—Ph

513

i-Pr

3,5-di-Cl—Ph

513-0

i-Pr

3,5-di-Cl—Ph

511

3,5-di-Cl—Ph

512

—N(CH 3 ) 2

3,5-di-Cl—Ph

A431

i-Pr

3,5-di-Cl—Ph

450

CF 3

3,5-di-Cl—Ph

A432

i-Pr

3,5-di-Cl—Ph

A473

i-Pr

3,5-di-Cl—Ph

A433

i-Pr

3,5-di-Cl—Ph

A434

i-Pr

3,5-di-Cl—Ph

AA,

A435

i-Pr

3,5-di-Cl—Ph

AB,

A436

i-Pr

Hy-

drogen,

A437

i-Pr

3,5-di-Cl—Ph

AC,

A438

i-Pr

3,5-di-Cl—Ph

AD,

A439

i-Pr

3,5-di-Cl—Ph

AF,

A440

i-Pr

3,5-di-Cl—Ph

AG,

A441

i-Pr

3,5-di-Cl—Ph

AH,

A442

i-Pr

3,5-di-Cl—Ph

AE,

A443

i-Pr

3,5-di-Cl—Ph

AJ,

A445

i-Pr

3,5-di-Cl—Ph

AK,

A446

i-Pr

3,5-di-Cl—Ph

AL,

A447

i-Pr

3,5-di-Cl—Ph

AM,

A448

i-Pr

3,5-di-Cl—Ph

AO,

A449

i-Pr

3,5-di-Cl—Ph

AQ,

A450

i-Pr

3,5-di-Cl—Ph

AR,

A451

i-Pr

3,5-di-Cl—Ph

AP,

A452

i-Pr

3,5-di-Cl—Ph

AS,

A472

i-Pr

3,5-di-Cl—Ph

AT,

A453

i-Pr

3,5-di-Cl—Ph

AN,

A454

i-Pr

3,5-di-Cl—Ph

AU,

419

i-Pr

3,5-di-Cl—Ph

397-0

OCH 2 CH═CH 2

3,5-di-Cl—Ph

A455

i-Pr

3,5-di-Cl—Ph

AW,

A456

i-Pr

3,5-di-Cl—Ph

AX,

A457

i-Pr

3,5-di-Cl—Ph

AY,

A458

i-Pr

3,5-di-Cl—Ph

AZ,

395

—OCHF 2

3,5-di-Cl—Ph

A459

3,5-di-Cl—Ph

A464

—N(CH 3 ) 2

2,6-di-Cl-4-F—Ph

A462

—N(CH 3 ) 2

2,4,6-tri-F—Ph

A463

—N(CH 3 ) 2

2,3-di-Cl-5-F—Ph

A460

—N(CH 3 ) 2

2,3,5-tri-F—Ph

A461

—N(CH 3 ) 2

2,3,5-tri-Cl—Ph

A, or

558

i-Pr

—C(O)CH 3

3,5-di-Cl—Ph

13. The method of claim 1 , wherein the endoparasitic infection is caused by Dirofilaria immitis.

14. The method of claim 3 , wherein the endoparasitic infection is caused by Dirofilaria immitis.

15. The method of claim 7 , wherein the endoparasitic infection is caused by Dirofilaria immitis.

16. The method of claim 12 , wherein the endoparasitic infection is caused by Dirofilaria immitis.

17. The method of claim 1 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Anoplocephala, Ancylostoma, Necator, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Cyathostomum, Cylicocyclus, Cylicodontophorus, Cylicostephanus, Craterostomum, Dictyocaulus, Dipetalonema, Dipylidium, Dirofilaria, Dracunculus, Echinococcus, Enterobius, Fasciola, Filaroides, Habronema, Haemonchus, Metastrongylus, Moniezia, Necator, Nematodirus, Nippostrongylus, Oesophagostomum, Onchocerca, Ostertagia, Oxyuris, Parascaris, Schistosoma, Strongylus, Taenia, Toxocara, Strongyloides, Toxascaris, Trichinella, Trichuris, Trichostrongylus, Triodontophorus, Uncinaria, Wuchereria , and combinations thereof.

18. The method of claim 3 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Anoplocephala, Ancylostoma, Necator, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Cyathostomum, Cylicocyclus, Cylicodontophorus, Cylicostephanus, Craterostomum, Dictyocaulus, Dipetalonema, Dipylidium, Dirofilaria, Dracunculus, Echinococcus, Enterobius, Fasciola, Filaroides, Habronema, Haemonchus, Metastrongylus, Moniezia, Necator, Nematodirus, Nippostrongylus, Oesophagostomum, Onchocerca, Ostertagia, Oxyuris, Parascaris, Schistosoma, Strongylus, Taenia, Toxocara, Strongyloides, Toxascaris, Trichinella, Trichuris, Trichostrongylus, Triodontophorus, Uncinaria, Wuchereria , and combinations thereof.

19. The method of claim 7 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Anoplocephala, Ancylostoma, Necator, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Cyathostomum, Cylicocyclus, Cylicodontophorus, Cylicostephanus, Craterostomum, Dictyocaulus, Dipetalonema, Dipylidium, Dirofilaria, Dracunculus, Echinococcus, Enterobius, Fasciola, Filaroides, Habronema, Haemonchus, Metastrongylus, Moniezia, Necator, Nematodirus, Nippostrongylus, Oesophagostomum, Onchocerca, Ostertagia, Oxyuris, Parascaris, Schistosoma, Strongylus, Taenia, Toxocara, Strongyloides, Toxascaris, Trichinella, Trichuris, Trichostrongylus, Triodontophorus, Uncinaria, Wuchereria , and combinations thereof.

20. The method of claim 12 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Anoplocephala, Ancylostoma, Necator, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Cyathostomum, Cylicocyclus, Cylicodontophorus, Cylicostephanus, Craterostomum, Dictyocaulus, Dipetalonema, Dipylidium, Dirofilaria, Dracunculus, Echinococcus, Enterobius, Fasciola, Filaroides, Habronema, Haemonchus, Metastrongylus, Moniezia, Necator, Nematodirus, Nippostrongylus, Oesophagostomum, Onchocerca, Ostertagia, Oxyuris, Parascaris, Schistosoma, Strongylus, Taenia, Toxocara, Strongyloides, Toxascaris, Trichinella, Trichuris, Trichostrongylus, Triodontophorus, Uncinaria, Wuchereria , and combinations thereof.

21. The method of claim 1 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Haemonchus contortus, Ostertagia circumcincta, Trichostrongylus axei, Trichostrongylus colubriformis, Cooperia curticei, Nematodirus battus, Ancylostoma duodenale, Ancylostoma ceylanicum, Ancylostoma braziliensis, Ascaris lumbricoides, Brugia malayi, Brugia timori, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Hymenolepis nana, Onchocerca volvulus, Strongyloides fuelleborni, Strongyloides stercoralis, Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichuris trichiura, Wuchereria bancrofti , and combinations thereof.

22. The method of claim 3 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Haemonchus contortus, Ostertagia circumcincta, Trichostrongylus axei, Trichostrongylus colubriformis, Cooperia curticei, Nematodirus battus, Ancylostoma duodenale, Ancylostoma ceylanicum, Ancylostoma braziliensis, Ascaris lumbricoides, Brugia malayi, Brugia timori, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Hymenolepis nana, Onchocerca volvulus, Strongyloides fuelleborni, Strongyloides stercoralis, Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichuris trichiura, Wuchereria bancrofti , and combinations thereof.

23. The method of claim 7 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Haemonchus contortus, Ostertagia circumcincta, Trichostrongylus axei, Trichostrongylus colubriformis, Cooperia curticei, Nematodirus battus, Ancylostoma duodenale, Ancylostoma ceylanicum, Ancylostoma braziliensis, Ascaris lumbricoides, Brugia malayi, Brugia timori, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Hymenolepis nana, Onchocerca volvulus, Strongyloides fuelleborni, Strongyloides stercoralis, Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichuris trichiura, Wuchereria bancrofti , and combinations thereof.

24. The method of claim 12 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Haemonchus contortus, Ostertagia circumcincta, Trichostrongylus axei, Trichostrongylus colubriformis, Cooperia curticei, Nematodirus battus, Ancylostoma duodenale, Ancylostoma ceylanicum, Ancylostoma braziliensis, Ascaris lumbricoides, Brugia malayi, Brugia timori, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Hymenolepis nana, Onchocerca volvulus, Strongyloides fuelleborni, Strongyloides stercoralis, Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichuris trichiura, Wuchereria bancrofti , and combinations thereof.

25. A method for the treatment, control and/or prevention of an endoparasitic infection in an animal in need thereof, which comprises administering to said animal an effective amount of a compound of the formula:

or a pharmaceutically acceptable salt thereof.

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

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

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

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

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

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

32. The method of claim 25 , wherein the endoparasitic infection is caused by Dirofilaria immitis.

33. The method of claim 25 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Anoplocephala, Ancylostoma, Necator, Ascaris, Brugia, Bunostomum, Capillaria, Chabertia, Cooperia, Cyathostomum, Cylicocyclus, Cylicodontophorus, Cylicostephanus, Craterostomum, Dictyocaulus, Dipetalonema, Dipylidium, Dirofilaria, Dracunculus, Echinococcus, Enterobius, Fasciola, Filaroides, Habronema, Haemonchus, Metastrongylus, Moniezia, Necator, Nematodirus, Nippostrongylus, Oesophagostomum, Onchocerca, Ostertagia, Oxyuris, Parascaris, Schistosoma, Strongylus, Taenia, Toxocara, Strongyloides, Toxascaris, Trichinella, Trichuris, Trichostrongylus, Triodontophorus, Uncinaria, Wuchereria , and combinations thereof.

34. The method of claim 25 , wherein the endoparasitic infection is caused by a parasite selected from the group consisting of Haemonchus contortus, Ostertagia circumcincta, Trichostrongylus axei, Trichostrongylus colubriformis, Cooperia curticei, Nematodirus battus, Ancylostoma duodenale, Ancylostoma ceylanicum, Ancylostoma braziliensis, Ascaris lumbricoides, Brugia malayi, Brugia timori, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Hymenolepis nana, Onchocerca volvulus, Strongyloides fuelleborni, Strongyloides stercoralis, Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichuris trichiura, Wuchereria bancrofti , and combinations thereof.

Assignments (5)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 29, 2025

From: BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG

To: BOEHRINGER INGELHEIM VETMEDICA GMBH

Reel/Frame 070971/0046 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2025

From: HERLE, BART

To: BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG

Reel/Frame 070434/0510 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 7, 2025

From: KOOLMAN, HANNES FIEPKO

To: BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG

Reel/Frame 070434/0756 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 23, 2024

From: LONG, ALAN

To: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

Reel/Frame 068051/0580 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 23, 2024

From: BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC.

To: BOEHRINGER INGELHEIM VETMEDICA GMBH

Reel/Frame 068051/0698 →

Continuity (3)

Continuation 17324288 · May 19, 2021

Provisional Application 63031656 · May 29, 2020

Related Publication 20240166653A1 · May 23, 2024

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