Control of arthropods in animals

Details Control of arthropods in animals Control of arthropods in animals

2000-12-04

2003-05-27

Weddington, Kevin E. (Department: 1614)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

Reexamination Certificate

active

06569886

ABSTRACT:

The present invention relates to a method of control of parasites in animals, compositions comprising a compound effective for the said control and compounds effective against parasites.
It is generally a goal of agronomists and veterinarians to possess sufficient means to control pests, particularly arthropods, when they attempt to invade or attack mammals, particularly domestic animals and/or livestock. A classical method of controlling such pests has been the use of topical and/or systemic pesticides on or in the domestic animal which is being attacked. Generally effective treatments include the oral administration of insect growth regulators, such as lufenuron, or antihelminth compounds such as an ivermectin or an avermectin, or the topical application of the insecticide fipronil. It is advantageous to apply pesticides to animals in oral form so as to prevent the possible contamination of humans or the surrounding environment. It is an object of the present invention to provide new pesticides which may be used in domestic animals.
Another object of the invention is to provide safer pesticides for domestic animals.
Another object of the invention is to provide new pesticides for domestic animals that may be used in lower doses than existing pesticides.
These objects are met in whole or in part by the present invention.
U.S. Pat. No. 5,079,370, EP-A 0,846,686, WO 98/24769 and WO 97/28126 disclose the use of arylpyrazoles as parasiticidal agents. However, these references are completely silent on the problem that anti parasitical agents often elicit emesis in the animal to be protected or cured from the parasites.
The present invention provides a method of controlling parasites in or on an animal comprising administering, preferably orally, to the animal a parasiticidally effective, substantially non-emetic amount of a 1-arylpyrazole of formula (I):
wherein:
R
201
is cyano, C(O)alkyl, C(S)NH
2
, C(NH)OR
203
, C(NH)SR
203
, alkyl, C(═NOH)NH
2
, C(═NNH
2
)NH
2
, C(O)NH
2
, C(O)NHR
205
, C(O)NR
205
R
206
, haloalkyl or heterocyclyl from the group:
optionally substituted by R
203
;
R
202
is S(O)
h
R
203
, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, cycloalkyl, halocycloalkyl, cycloalkyl-alkyl , C
2
-C
6
alkynyl, nitro or imidazol-2-yl optionally substituted by alkyl, alkoxy, haloalkyl, halogen, cyano and/or nitro;
R
203
is alkyl or haloalkyl;
R
204
is —OH, R
205
O—, HC(O)O—, R
205
C(O)O—, R
205
OC(O)O—, NH
2
C(O)O—, R
205
NHC(O)O—, R
205
R
206
NC(O)O—, R
205
S(O)
n
C(O)O—, R
206
SO
2
O—, aryl-SO
2
O—, (C
4
-C
7
)-oxacycloalkyloxy, R
205
R
206
N—C(NR
205
)—O—, R
205
R
206
N—C(NH)—O—, R
205
NH—C(NR
205
)—O—, R
205
NH—C(NH)—O—, R
205
N═CH—O—, R
205
N═C(R
206
)—O—, R
205
NH—C(S)—O—, R
205
R
206
N—C(S)—O—;
R
205
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, C
2
-C
6
alkinyl;
R
206
is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, alkoxyalkyl, haloalkoxyalkyl, aryl optionally substituted, hetaryl optionally substituted, arylalkyl optionally substituted, hetarylalkyl optionally substituted;
or R
205
and R
206
may form together with the nitrogen to which they are attached a 3 to 7 membered ring which additionally may contain one or more heteroatoms selected from nitrogen, oxygen and sulfur;
X
1
is selected from nitrogen and C—R
212
;
R
211
, R
212
are independently selected from halogen, hydrogen, CN, C
1
-C
3
alkyl and NO
2
;
R
213
is selected from halogen, haloalkyl, haloalkoxy, —S(O)
k
CF
3
, and —SF
5
or forms a ring with R
214
;
R
214
is hydrogen or may constitute together with R
213
a group of OCF
2
O, CF
2
OCF
2
, CF
2
OCF
2
O and CF
2
CF
2
O, which forms together with the carbons they are attached to a five to six membered ring; and
h, k and n are independently selected from 0, 1, and 2;
and veterinarily acceptable salts thereof.
By the term “veterinariiy acceptable salts” is meant salts the anions of which are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, e.g. formed by compounds of formula (I) containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.
When R
204
is OH the pyrazole structure can also be exhibited by its tautomeric form as pyrazolon structure.
Unless otherwise specified, alkyl and alkoxy groups are straight chain or branched and are generally lower alkyl and alkoxy groups, that is having from one to six carbon atoms, preferably from one to four carbon atoms. Generally, the haloalkyl, haloalkoxy and haloalkylamino groups have from one to four carbon atoms. Halogen means F, Cl, Br, and I, preferably F and Cl. The haloalkyl and haloalkoxy and haloalkylamino groups can bear one or more halogen atoms; preferred groups of this type include —CF
3
and —OCF
3
. Cycloalkyl groups generally have from 3 to 6 carbon atoms, preferably from 3 to 5 carbon atoms and may be substituted by one or more halogen atoms. Preferably in compounds of formula (I), alkyl groups are generally substituted by from one to five halogen atoms, preferably from one to three halogen atoms. Chlorine and fluorine atoms are preferred.
In compounds of formula (I) the following examples of radicals are provided:
An example of cycloalkylalkyl is cyclopropylmethyl;
an example of cycloalkoxy is cyclopropyloxy; and
an example of alkoxyalkyl is CH
3
OCH
2
—.
Generally, in dialkylamino or di(haloalkyl)amino radicals, the alkyl and haloalkyl groups on nitrogen may be chosen independently of one another.
Generally, the term “aryl” means a carbocyclic aromatic radical having preferably 6 to 14, in particular 6 to 12, carbon atoms, for example phenyl, naphthyl or biphenylyl, preferably phenyl;
the term “heterocyclyl” preferably a hetaryl or heteroaliphatic ring system, “hetaryl” preferably being understood as meaning an aryl radical in which at least one CH group is replaced by N and/or at least two adjacent CH groups are replaced by S, NH or O, for example a radical of thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4triazine, 1,2,4,5-triazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine or 4H-quinolizine;
and the term “heteroaliphatic ring system” preferably a (C
3
-C
8
)cycloalkyl radical in which at least one carbon unit is replaced by O, S or a group NR′ and R′ is hydrogen, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkanoyl, (C
1
-C
4
)alkoxycarbonyl, (C
1
-C
4
)alkylsulfonyl, (C
1
-C
4
)alkoxy or aryl;
The substituents with which the various aliphatic, cycloaliphatic, aromatic and heterocyclic ring systems can be provided are, for example, halogen, nitro, cyano, di-(C
1
-C
4
)alkylamino, (C
1
-C
4
)alkyl, (C
1
-C
8
)cycloalkyl, (C
1
-C
4
)trialkylsilyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkoxy-(C
1
-C
4
)alkyl, (C
1
-C
2
)alkoxy-[CH
2
CH
2
O]
0,1,2
-ethoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfinyl, (C
1
-C
4
)alkylsulfonyl, phenyl, benzyl, phenoxy, halophenoxy, (C
1
-C
4
)alkylphenoxy, (C
1
-C
4
)alkoxyphenoxy, phenylthio, heterocyclyl, heterocyclylthio or heterocyclyloxy, it being possible for one o

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