Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-06-09
2003-03-11
Ramsuer, Robert W. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S368400
Reexamination Certificate
active
06531501
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a method of control of parasites in animals, compositions comprising a compound effective for said control and new compounds effective against parasites.
2. Related Art
The state of the art is represented by Hatton et al U.S. Pat. No. 5,232,940, Stetter et al U.S. Pat. No. 5,580,843, Huang et al U.S. Pat. No. 5,556,873, EP 0511845, WO 87/03781, WO 93/06089, WO 94/21606, WO 97/07102, WO 98/24767, WO 98/28277, WO 98/28278, WO 98/28279, EP 0295117, EP 0846686, EP 0659745, WO 97/22593 and EP 0811615.
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.
SUMMARY AND OBJECTS OF THE INVENTION
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 are may be used in lower doses than existing pesticides.
These objects are met in whole or in part by the present invention.
The present invention provides a method of controlling parasites in or on an animal comprising administering orally to the animal a parasiticidally effective, substantially non-emetic amount of a 1-arylpyrazole of formula (I):
wherein:
R
1
is cyano, acetyl, C(S)NH
2
, alkyl, haloalkyl, C(═NOH)NH
2
or C(═NNH
2
)NH
2
;
R
2
is S(O)
n
R
3
, C
2
-C
3
alkenyl, C
2
-C
3
haloalkenyl, cycloalkyl, halocycloalkyl or C
2
-C
3
alkynyl;
R
3
is alkyl or haloalkyl;
R
4
is —N═C(R
5
)—Z—R
6
, —N═C(R
5
)—N(R
7
)—R
8
, or —N(R
9
)—C(R
5
)═NR
6
;
R
5
is hydrogen, alkyl, or alkyl substituted by halogen, alkoxy, haloalkoxy or —S(O)
m
R
15
;
R
6
and R
7
each independently represent hydrogen, alkyl, C
3
-C
5
alkenyl or C
3
-C
5
alkynyl; or
alkyl substituted by one or more halogen, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, cyano or —S(O)
m
R
15
; or alkyl substituted by phenyl or pyridyl each of which is optionally substituted with one or more groups selected from halogen, nitro and alkyl; or
R
6
and R
7
may form together with the nitrogen to which they are attached a 3 to 7 membered ring which may additionally contain one or more heteroatoms selected from oxygen, nitrogen or sulfur;
R
8
is alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, R
14
CO— or —S(O)
t
R
10
;
R
9
, R
10
and R
14
are alkyl or haloalkyl;
R
11
and R
12
are independently selected from halogen, hydrogen, CN and NO
2
;
R
13
is selected from halogen, haloalkyl, haloalkoxy, —S(O)
q
CF
3
, and —SF
5
;
R
15
is alkyl or haloalkyl;
X is selected from nitrogen and C—R
12
;
Z is O, S(O)
a
, or NR
7
;
a, m, n and q are independently selected from 0, 1, and 2; and
t is 0 or 2;
and veterinarily acceptable salts thereof.
In another aspect, the present invention provides a method of controlling parasites in or on an animal comprising administering orally to the animal a parasiticidally effective, substantially non-emetic amount of a 1-arylpyrazole of formula (XX):
wherein:
R
201
is cyano, C(O)alkyl, C(S)NH
2
, alkyl, C(═NOH)NH
2
or C(═NNH
2
)NH
2
;
R
202
is S(O)
h
R
203
, C
2
-C
3
alkenyl, C
2
-C
3
haloalkenyl, cycloalkyl, halocycloalkyl or C
2
-C
3
alkynyl;
R
203
is alkyl or haloalkyl;
R
204
is —N(R
205
)C(O)CR
206
R
207
R
208
, —N(R
205
)C(O)aryl, or —N(R
205
)C(O)OR
207
;
R
205
is alkyl, haloalkyl, cycloalkyl, halocycloalkyl, cycloalkylalkyl, halocycloalkylalkyl, alkoxyalkyl, haloalkoxyalkyl, C
3
-C
5
alkenyl, C
3
-C
5
haloalkenyl, C
3
-C
5
alkynyl, C
3
-C
5
haloalkynyl;
R
206
is hydrogen, halogen, alkoxy, haloalkoxy, alkoxyalkyl, haloalkoxyalkyl, formyloxy, alkylcarbonyloxy, haloalkylcarbonyloxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkyl amino, dialkylamino, haloalkylamino, di(haloalkyl)amino, cycloalkyloxy, halocycloalkyloxy, alkoxyalkoxy, haloalkoxyalkoxy, alkoxyalkoxyalkoxy, aryloxy, or arylalkoxy;
R
207
and R
208
are independently hydrogen, alkyl, haloalkyl, cycloalkyl, or halocycloalkyl; or R
207
and R
208
may form together with the carbon 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
and R
212
are independently selected from halogen, hydrogen, CN and NO
2
;
R
213
is selected from halogen, haloalkyl, haloalkoxy, —S(O)
k
CF
3
, and —SF
5
; and
h and k are independently selected from 0, 1, and 2;
and veterinarily acceptable salts thereof.
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
By the term “veterinarily 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 formulae (I) and (XX) 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.
Unless otherwise specified, alkyl and alkoxy groups here and throughout this specification 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 alkylamino groups have from one to four carbon atoms. The haloalkyl and haloalkoxy 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. Alkenyl, haloalkenyl, alkynyl, and haloalkynyl groups generally contain from 3 to 5 carbon atoms. By the term aryl is generally meant phenyl, pyridyl, furyl, and thiopheneyl (thienyl), each of which is optionally substituted by one or more halogen, alkyl, haloalkyl, nitro, alkoxy, haloalkoxy, hydroxy, amino, alkylamino or dialkylamino. In compounds of formula (I), by the term substituted alkyl is meant alkyl which is substituted by one or more halogen, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, cyano or —S(O)
m
R
15
; or alkyl substituted by phenyl or pyridyl each of which is optionally substituted with one or more groups selected from halogen, nitro and alkyl; wherein R
15
is alkyl or haloalkyl and m is zero, one or two. 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.
The above definitions of alkyl, alkoxy and various-other groups of course pertain not only to those radicals themselves but also to those portions of larger radicals.
Compounds of formula (I) wherein R
4
is —N═C(R
5
)—Z—R
6
, Z is NR
7
and R
6
represents a hydrogen atom may exist as the tautomeric double bond isomer form —NH—C(R
5
)═N—R
7
. It is to be understood that both such forms are embraced by the present invention.
In compounds of formula (XX) the following examples of radicals are provided:
An example of cycloalkylalkyl is cyclopropylmethyl;
an example of cycloalkoxy is cyclopropyloxy;
an example of alkoxyalkyl is CH
3
OCH
2
—;
an example of alkoxyalkoxy is CH
3
OCH
2
O—;
An example of alkoxyalkoxyalkoxy is CH
3
OCH
2
OCH
Chou David Teh-Wei
de Leon Adalberto Perez
Huber Scot Kevin
Malaska Michael James
McComb Susan Marie
Aventis CropScience S.A.
Burns Doane Swecker & Mathis L.L.P.
Ramsuer Robert W.
LandOfFree
Control of arthropods in animals does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Control of arthropods in animals, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Control of arthropods in animals will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3045286