Compounds and methods for treating nematode infections

Patent metadata

Field	Value
Publication number	US-11364234-B2
Application number	US-201916565917-A
Country	US
Kind code	B2
Filing date	Sep 10, 2019
Priority date	Sep 12, 2018
Publication date	Jun 21, 2022
Grant date	Jun 21, 2022

Abstract

The present application relates to the treatment of nematode infections. For example, the application relates to the use of compounds of Formula I and/or II as defined herein for treatment of a nematode infection or a disease, disorder or condition arising from a nematode infection:

First claim

The invention claimed is:

1. A method of treating or preventing a nematode infection comprising administering an effective amount of a compound of Formula I

and/or a pharmaceutically acceptable salt and/or solvate thereof to a subject in need thereof
wherein:
L is C 0-4 alkylene;
R 1 is C 4-8 cycloalkyl or C 4-8 cycloalkene, each of which is unsubstituted or substituted with one or two substituents independently selected from C 1-4 alkyl, C 1-4 fluoroalkyl and C 1-4 alkyl substituted with Cl or CN; and
R 2 is H, NO 2 , Cl, F or CN.

2. The method of claim 1 , wherein L is CH 2 .

3. The method of claim 1 , wherein the compound of Formula I is selected from

4. The method of claim 1 , wherein the infection is an infection of a nematode of a species selected from Cooperia oncophora, Haemonchus contortus , and Caenorhabditis elegans.

5. The method claim 1 , wherein the subject is selected from a human, a mammal, a bird, a plant, a seed, and soil.

6. A method of treating or preventing a disease, disorder or condition arising from a nematode infection comprising administering an effective amount a compound of Formula I

and/or a pharmaceutically acceptable salt and/or solvate thereof to a subject in need thereof
wherein:
L is C 0-4 alkylene;
R 1 is C 4-8 cycloalkyl or C 4-8 cycloalkene, each of which is unsubstituted or substituted with one or two substituents independently selected from C 1-4 alkyl, C 1-4 fluoroalkyl and C 1-4 alkyl substituted with Cl or CN; and
R 2 is H, NO 2 , Cl, F or CN.

7. The method of claim 6 , wherein L is CH 2 .

8. The method of claim 6 , wherein the compound of Formula I is selected from

9. The method of claim 6 , wherein the infection is an infection of a nematode of a species selected from Cooperia oncophora, Haemonchus contortus , and Caenorhabditis elegans.

10. The method claim 6 , wherein the subject is selected from a human, a mammal, a bird, a plant, a seed, and soil.

11. The method of claim 10 , wherein the subject is selected from a plant, a seed and soil and the composition is administered through one or more means selected from pre-planting, post-planting, as a feed additive, a drench, an external application, a pill and by injection.

12. The method of claim 1 , wherein the infection is an infection of a nematode of a genus selected from Ancylostoma, Dirofilaria, Toxocara, Ascaris, Uncinaria, Parascaris, Trichostrongylus, Oesophagostomum, Dictyocaulus, Cooperia and Haemonchus.

13. The method of claim 12 , wherein the infection is an infection of a nematode of a species selected from Ancylostoma caninum, Dirofilaria immitis, Toxocara canis, Toxocara cati, Ascaris suum, Cooperia oncophora and Haemonchus contortus.

14. The method of claim 1 , wherein the subject is human.

15. The method of claim 1 , wherein the subject is a domesticated animal.

16. The method of claim 6 , wherein the infection is an infection of a nematode of a genus selected from Ancylostoma, Dirofilaria, Toxocara, Ascaris, Uncinaria, Parascaris, Trichostrongylus, Oesophagostomum, Dictyocaulus, Cooperia and Haemonchus.

17. The method of claim 16 , wherein the infection is an infection of a nematode of a species selected from Ancylostoma caninum, Dirofilaria immitis, Toxocara canis, Toxocara cati, Ascaris suum, Cooperia oncophora and Haemonchus contortus.

18. The method of claim 6 , wherein the subject is human.

19. The method of claim 6 , wherein the subject is a domesticated animal or is livestock.

20. The method of claim 15 , wherein the subject is livestock.

Assignees

• Governing Council Univ Toronto
• Ontario Institute For Cancer Res Oicr

Inventors

• Roy Peter
• Harrington Sean
• Pyche Jacob
• Kulke Daniel
• Luciani Genna M
• Burns Andrew
• Lautens Mark
• Ross Rachel
• Uehling David

Classifications

• A61K31/505

  Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim · CPC title

• A61K31/44

  Non condensed pyridines; Hydrogenated derivatives thereof · CPC title

• A01N43/60

  1,4-Diazines; Hydrogenated 1,4-diazines · CPC title

• A61K31/445 Primary

  Non condensed piperidines, e.g. piperocaine · CPC title

• A61K31/495 Primary

  having six-membered rings with two {or more} nitrogen atoms as the only ring heteroatoms, e.g. piperazine {or tetrazines}(A61K31/48 takes precedence {; with three nitrogen atoms A61K31/53}) · CPC title