Parasiticidal dihydroisoxazole compounds
View Patent ↗Provided are dihydroisoxazole compounds I useful for controlling parasites both in animals and agriculture. Further provided are methods for controlling parasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling parasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. Also provided are compounds and processes useful for making the dihydroisoxazole compounds. wherein A is
1. A compound, or a salt thereof, of formula I
wherein A is
n is 0 or 1;
R 1 is phenyl substituted with 2 or 3 of the same or different halo atoms;
R 2 is, at each occurrence, hydrogen;
R 3 is
p is, at each occurrence, independently 0 or 1;
R 4 is
R 5 is
and
R 6 is hydrogen, C 1 -C 5 haloalkyl, C 1 -C 5 cyanoalkyl, or C 2 -C 5 alkynyl.
2. The compound of claim 1 , or salt thereof, wherein
R 1 is phenyl substituted 3 times with the same or different of chloro and fluoro;
n is 0;
R 3 is —CH 2 —R 4 ;
R 4 is —C(O)—R 5 ;
and R 6 is difluoroethyl, cyanomethyl, or ethylmethyl.
3. The compound of claim 2 or salt thereof, wherein R 1 is
4. The compound of claim 3 or salt thereof, wherein R 3 is
5. The compound of claim 3 or salt thereof, wherein R 3 is
6. The compound of claim 3 or salt thereof, wherein R 3 is
7. The compound of claim 1 , or salt thereof, being 3-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-(prop-2-ynylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxamide.
8. The compound of claim 1 , or salt thereof, being (S)-3-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-(prop-2-ynylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxamide.
9. A formulation comprising a compound of claim 1 , or a salt thereof, and one or more acceptable carriers.
10. A formulation comprising a compound of claim 2 , or a salt thereof, and one or more acceptable carriers.
11. The formulation of claim 10 , further comprising an additional active ingredient.
12. The formulation of claim 11 , wherein the formulation is an injectable formulation.
13. A formulation comprising a compound of claim 4 , or a salt thereof, and one or more acceptable carriers.
14. The formulation of claim 13 further comprising an additional active ingredient.
15. The formulation of claim 14 , wherein the formulation is an injectable formulation.
16. A formulation comprising a compound of claim 6 , or a salt thereof, and one or more acceptable carriers.
17. The formulation of claim 16 , further comprising an additional active ingredient.
18. The formulation of claim 17 , wherein the formulation is an injectable formulation.
19. A formulation comprising a compound of claim 8 , or a salt thereof, and one or more acceptable carriers.
20. The formulation of claim 19 , further comprising an additional active ingredient.
21. The formulation of claim 20 , wherein the formulation is an injectable formulation.
22. A method of controlling a parasite infestation in or on a non-human mammal in need thereof comprising administering an effective amount of a compound of claim 1 , or salt thereof, to said animal.
23. The method of claim 22 , wherein said non-human mammal is a dog or cat, and said parasite is a flea or tick.
24. The method of claim 23 , wherein the administering is parenteral administration.
25. A method of controlling a parasite infestation in or on a non-human mammal in need thereof comprising administering an effective amount of a compound of claim 2 , or salt thereof, to said animal.
26. The method of claim 25 , wherein said non-human mammal is a dog or cat, and said parasite is a flea or tick.
27. The method of claim 26 , wherein the administering is parenteral administration.
28. A method of controlling a parasite infestation in or on a non-human mammal in need thereof comprising administering an effective amount of a compound of claim 4 , or salt thereof, to said animal.
29. The method of claim 28 , wherein said non-human mammal is a dog or cat, and said parasite is a flea or tick.
30. The method of claim 29 , wherein the administering is parenteral administration.
31. A method of controlling a parasite infestation in or on a non-human mammal in need thereof comprising administering an effective amount of a compound of claim 6 , or salt thereof, to said animal.
32. The method of claim 31 , wherein said non-human mammal is a dog or cat, and said parasite is a flea or tick.
33. The method of claim 32 , wherein the administering is parenteral administration.
34. A method of controlling a parasite infestation in or on a non-human mammal in need thereof comprising administering an effective amount of a compound of claim 8 , or salt thereof, to said animal.
35. The method of claim 34 , wherein said non-human mammal is a dog or cat, and said parasite is a flea or tick.
36. The method of claim 35 , wherein the administering is parenteral administration.