IP Library › Granted Patent US 6,992,099
Granted Patent B2
US 6,992,099 · App. 10/406,491 · Granted Jan 31, 2006

Control of arthropods in animals

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Quick Facts
Patent No.
US 6,992,099
App. No.
10/406,491
Granted
Jan 31, 2006
Kind
B2
Abstract

A method of controlling parasites in or on an animal comprising administering to the animal a parasiticidally effective, substantially non-emetic 1-arylpyrazole.

Claims (196)

1. A compound having the formula (II):

wherein:

R 21 is cyano, C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH, HC(O)O—, R 25 C(O)O—, R 25 OC(O)O—, R 25 R 25 N—C(O)—O— or R 25 S(O) n C(O)O—;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, hetaryl optionally substituted, arylalkyl optionally substituted, hetarylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

or two groups R 25 form together with the nitrogen to which they are attached a 3 to 7 membered ring which optionally has one or more additional heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

r is selected from the group consisting of 0, 1 and 2; and

when R 21 is cyano, m is selected from the group consisting of 1 and 2, or

when R 21 is other than cyano, m is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof;

provided that when R 21 is cyano, then R 24 is not R 25 R 25 —N—C(O)—O—.

2. A compound according to claim 1 , wherein:

R 21 is cyano;

R 22 is S(O) m R 23 ;

R 23 is haloalkyl;

R 24 is OH;

X is C—R 32 ;

R 31 and R 32 are independently selected from halogen;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 , and —SF 5 ;

r is selected from the group consisting of 0, 1, and 2; and

m is selected from the group consisting of 1 and 2.

3. A compound according to claim 2 , wherein R 23 is CF 3 .

4. The compound according to claim 2 , which is 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfinyl-5-hydroxypyrazole.

5. The compound according to claim 2 , which is 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-4-trifluoromethylsulfonyl-5-hydroxypyrazole.

6. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound of formula (II) as defined in claim 1 , or a veterinarily acceptable salt thereof, and a veterinarily acceptable carrier therefor.

7. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 2 , and a veterinarily acceptable carrier therefor.

8. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 3 , and a veterinarily acceptable carrier therefor.

9. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 4 , and a veterinarily acceptable carrier therefor.

10. A composition comprising a parasiticidally effective substantially non-emetic amount of a compound as defined in claim 5 , and a veterinarily acceptable carrier therefor.

11. A compound having the formula (II):

wherein:

R 21 is cyano, C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH, HC(O)O—, R 25 C(O)O—, R 25 OC(O)O—, R 25 R 25 N—C(O)—O— or R 25 S(O) n C(O)O—;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, hetaryl optionally substituted, arylalkyl optionally substituted, hetarylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

or two groups R 25 form together with the nitrogen to which they are attached a 3 to 7 membered ring which optionally has one or more additional heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof;

provided that when R 21 is cyano, then R 24 is not R 25 R 25 —N—C(O)—O—.

12. A compound having the formula (II):

wherein:

R 21 is cyano;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH, HC(O)O—, R 25 C(O)O—, R 25 OC(O)O— or R 25 S(O) n C(O)O—;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, hetaryl optionally substituted, arylalkyl optionally substituted, hetarylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

or two groups R 25 form together with the nitrogen to which they are attached a 3 to 7 membered ring which optionally has one or more additional heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof.

13. A compound having the formula (II):

wherein:

R 21 is C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH, HC(O)O—, R 25 C(O)O—, R 25 OC(O)O— or R 25 S(O) n C(O)O— or R 25 S(O) n C(O)O—;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, hetaryl optionally substituted, arylalkyl optionally substituted, hetarylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

or two groups R 25 form together with the nitrogen to which they are attached a 3 to 7 membered ring which optionally has one or more additional heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 0, 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof.

14. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound of formula (II) as defined in claim 11 , or a veterinarily acceptable salt thereof, and a veterinarily acceptable carrier therefor.

15. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 12 , and a veterinarily acceptable carrier therefor.

16. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 13 , and a veterinarily acceptable carrier therefor.

17. A compound according to claim 1 , having the formula (II):

wherein:

R 21 is cyano, C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH, HC(O)O—, R 25 C(O)O—, R 25 OC(O)O—, R 25 R 25 N—C(O)—O— or R 25 S(O) n C(O)O—;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, arylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

r is selected from the group consisting of 0, 1 and 2; and

when R 21 is cyano, m is selected from the group consisting of 1 and 2, or

when R 21 is other than cyano, m is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof;

provided that when R 21 is cyano, then R 24 is not R 25 R 25 —N—C(O)—O—.

18. A compound according to claim 11 , having the formula (II):

wherein:

R 21 is cyano, C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH, HC(O)O—, R 25 C(O)O—, R 25 OC(O)O—, R 25 R 25 N—C(O)—O— or R 25 S(O) n C(O)O—;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, arylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof;

provided that when R 21 is cyano, then R 24 is not R 25 R 25 —N—C(O)—O—.

19. A compound according to claim 12 , having the formula (II):

wherein:

R 21 is cyano;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH, HC(O)O—, R 25 C(O)O—, R 25 OC(O)O— or R 25 S(O) n C(O)O—;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, arylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof.

20. A compound according to claim 13 , having the formula (II):

wherein:

R 21 is C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH, HC(O)O—, R 25 C(O)O—, R 25 OC(O)O—, R 25 R 25 N—C(O)—O— or R 25 S(O) n C(O)O—;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, arylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 0, 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof.

21. A compound according to claim 1 , having the formula (II):

wherein:

R 21 is cyano, C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, arylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

r is selected from the group consisting of 0, 1 and 2; and

when R 21 is cyano, m is selected from the group consisting of 1 and 2, or

when R 21 is other than cyano, m is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof.

22. A compound according to claim 11 , having the formula (II):

wherein:

R 21 is cyano, C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, arylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof.

23. A compound according to claim 12 , having the formula (II):

wherein:

R 21 is cyano;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, arylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof.

24. A compound according to claim 13 , having the formula (II):

wherein:

R 21 is C(═S)NH 2 , C(═NOH)NH 2 or C(═NNH 2 )NH 2 ;

R 22 is S(O) m R 23 ;

R 23 is alkyl or haloalkyl;

R 24 is OH;

R 25 is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, adamantyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, haloalkylaminoalkyl, di(haloalkyl)aminoalkyl, aryl optionally substituted, arylalkyl optionally substituted, C 2 –C 6 alkenyl or C 2 –C 6 alkynyl;

X is C—R 32 ;

R 31 and R 32 are independently selected from the group consisting of halogen, hydrogen, CN, C 1 –C 3 alkyl and NO 2 ;

R 33 is selected from the group consisting of halogen, haloalkyl, haloalkoxy, —S(O) r CF 3 and SF 5 ;

m is selected from the group consisting of 0, 1 and 2; and

r is selected from the group consisting of 0, 1 and 2;

or a veterinarily acceptable salt thereof.

25. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound of formula (II) as defined in claim 17 , or a veterinarily acceptable salt thereof, and a veterinarily acceptable carrier therefor.

26. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 18 , and a veterinarily acceptable carrier therefor.

27. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 19 , and a veterinarily acceptable carrier therefor.

28. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 20 , and a veterinarily acceptable carrier therefor.

29. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound of formula (II) as defined in claim 21 , or a veterinarily acceptable salt thereof, and a veterinarily acceptable carrier therefor.

30. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 22 , and a veterinarily acceptable carrier therefor.

31. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound of formula (II) as defined in claim 23 , or a veterinarily acceptable salt thereof, and a veterinarily acceptable carrier therefor.

32. A composition comprising a parasiticidally effective, substantially non-emetic amount of a compound as defined in claim 24 , and a veterinarily acceptable carrier therefor.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 15, 2016
From: MERIAL LIMITED
To: MERIAL, INC.
Reel/Frame 039024/0908 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2011
From: BAYER CROPSCIENCE SA
To: MERIAL LIMITED
Reel/Frame 026375/0867 →