Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1996-09-25
2002-05-28
Pak, John (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S156000, C514S210010, C514S211010, C514S212010, C514S218000, C514S222200, C514S228800, C514S241000, C514S247000, C514S277000, C514S359000, C514S396000, C514S397000, C514S399000, C514S403000, C514S406000, C514S772000, C514S772100, C514S772300, C514S875000, C514S937000, C514S946000, C514S947000, C514S964000, C514S970000, C514S971000, C514S975000
Reexamination Certificate
active
06395765
ABSTRACT:
The present invention relates to a composition for the treatment and protection of animals which are infested with parasites or likely to be infested with them.
More particularly, the aim of the invention is to control and eliminate the parasites which infest pets, and especially cats and dogs.
Pets are often infested with one or more of the following parasites:
cat and dog fleas (Ctenocephalides felis, Ctenocephalides sp. and the like),
ticks (Rhipicephalus sp., Ixodes sp., Dermacentor sp., Amblyoma sp. and the like)
galls (Demodex sp., Sarcoptes sp., Otodectes sp. and the like).
Fleas cause an animal a great deal of stress and are harmful to its health. Moreover, fleas are also vectors of pathogenic agents, such as dog tapeworm (Dipylidium caninum), and can also attack man.
Similarly, ticks can also cause an animal stress and be harmful to its health. They can also be harmful to man. However, the most serious problem of ticks is that they are the vector of pathogenic agents which may affect the animal as much as man. Among the major diseases which need to be avoided, mention may be made of borrelioses (Lyme disease caused by Borrelia burgdorferi), babesioses (or piroplasmoses caused by Babesia sp.) and rickettsioses (also known as Rocky Mountain spotted fever). Ticks can also release toxins with paralysing and inflammatory properties, these toxins occasionally being fatal.
Lastly, galls are particularly difficult to combat since there are very few active substances which act on these parasites, and they require frequent treatment.
Many more or less active and more or less expensive insecticides exist. However, phenomena of resistance are often associated with their use, as is the case, for example, with carbamates, organophosphorus compounds and pyrethroids.
Moreover, international patent application WO-A-87/03781 and European patent application EP-A-0,295,117 describe a large family of N-phenyl-pyrazoles with a very broad spectrum of activity, including antiparasitic activities.
The object of the invention is to provide novel antiparasitic compositions for the treatment and protection of animals, these compositions being of great efficacy while at the same time being easy to use.
Another object of the invention is to provide such compositions which are easy to use on any type of domestic animal, irrespective of its size and the nature of its coat.
Yet another object of the invention is to provide such compositions which are effective and do not need to be sprinkled over the animal's entire body.
Yet another object of the invention is to provide such compositions which, when applied locally, will subsequently diffuse over the animal's entire body and then dry, while at the same time avoiding any phenomenon of crystallization as far as possible.
Yet another object of the invention is to provide such compositions which, after drying, do not affect the appearance of the coat and in particular do not leave crystals and do not make the coat sticky.
These objects are achieved by the invention, the subject of which is antiparasitic compositions which are useful in particular in the treatment and protection of domestic animals which are infested with parasites or are likely to be infested with them, these compositions comprising, in the form of a ready-to-use solution:
a) an insecticidal active substance of formula (I),
in which:
R
1
is a halogen atom, CN or methyl;
R
2
is S(O)
n
R
3
or 4,5-dicyanoimidazol-2-yl or haloalkyl;
R
3
is alkyl or haloalkyl, for example lower haloalkyl;
R
4
represents a hydrogen or halogen atom; or a radical NR
5
R
6
, S(O)
m
R
7
, C(O)R
7
or C(O)OR
7
, alkyl, haloalkyl or OR
8
or a radical —N═C (R
9
) (R
10
);
R
5
and R
6
independently represents a hydrogen atom or an alkyl, haloakyl, C(O)alkyl, S(O)
r
CF
3
, acyl or alkoxycabonyl radical; or R
5
and R
6
may together form a divalent alkylene radical which may be interrupted by one or two divalent hereto atoms such as oxygen or sulphur;
R
7
represents an alkyl or haloalkyl radical;
R
8
represents an alkyl or haloalkyl radical or a hydrogen atom;
R
9
represents an alkyl radical or a hydrogen atom;
R
10
represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms or groups such as OH, —O-alkyl, —S-alkyl, cyano or alkyl;
Y represents a halogen atom or a haloalkyl or haloalkoxy radical, for example a lower haloalkoxy radical, or an SF
5
radical, with the possibility that:
Y is CN or NO
2
in positions 2 and 6 (with reference to the carbon of the phenyl ring which is attached to the pyrazole ring and designated 1);
the carbon in position 2 of the phenyl ring is replaced by a trivalent nitrogen atom;
Y is S(O)
q
CF
3
in position 4 on the phenyl ring, but preferably haloalkyl, haloalkoxy or SF
5
;
m, n, q and r represent, independently of each other, an integer equal to 0, 1 or 2;
p is an integer equal to 1, 2, 3, 4 or 5, preferably equal to 1, 2 or 3, in particular 3;
with the proviso that when R
1
is methyl, then either R
3
is haloalkyl, R
4
is NH
2
, p is 2, Y in position 6 is Cl, Y in position 4 is CF
3
and the carbon in position 2 of the phenyl is replaced by N; or R
2
is 4,5-dicyanoimidazol-2-yl, R
4
is Cl, p is 3, Y in position 6 is Cl, Y in position 4 is CF
3
and the carbon in position 2 of the phenyl is replaced by ═C—Cl,
it being possible for this compound of formula (I) advantageously to be present in the formulation in a proportion of from 1 to 20%, preferably from 5 to 15% (percentages expressed as weight per unit volume=W/V),
b) a crystallization inhibitor which is present, in particular, in a proportion of from 1 to 20% (W/V), preferably from 5 to 15%, this inhibitor satisfying the test according to which: 0.3 ml of a solution A comprising 10% (W/V) of the compound of formula (I) in the solvent defined in c) below, and 10% of this inhibitor, are placed on a glass slide at 20° C. for 24 hours, after which few or no crystals, in particularly fewer than 10 crystals, preferably 0 crystals, are seen with the naked eye on the glass slide,
c) an organic solvent having a dielectric constant of between 10 and 35, preferably of between 20 and 30, the content of this solvent c) in the overall composition preferably representing the complement to 100% of the composition,
d) an organic co-solvent having a boiling point below 100° C., preferably below 80° C., and having a dielectric constant of between 10 and 40, preferably of between 20 and 30; this co-solvent may advantageously be present in the composition in a d) /c) weight/weight (W/W) ratio of between 1/15 and 1/2. The solvent is volatile so as to act in particular as a drying promoter, and is miscible with water and/or with the solvent c).
Preferably, the insecticidal active substance corresponds to formula (II),
in which:
R
1
is a halogen atom, CN or methyl;
R
2
is S(O),R
3
or 4,5-dicyanoimidazol-2-yl or haloalkyl;
R
3
is alkyl or haloalkyl;
R
4
represents a hydrogen or halogen atom; or a radical NR
5
R
6
, S(O)
m
R
7
, C(O)R
7
or C(O)OR
7
, alkyl, haloalkyl or OR
8
or a radical —N═C(R
9
) (R
10
);
R
5
and R
6
independently represent a hydrogen atom or an alkyl, haloalkyl, C(O)alkyl, S(O)
r
CF
3
or alkoxy carbonyl radical; or R
5
and R
6
may together form a divalent alkylene radical which may be interrupted by one or two divalent hetero atoms such as oxygen or sulphur;
R
7
represents an alkyl or haloalkyl radical;
R
8
represents an alkyl or haloalkyl radical or a hydrogen atom;
R
9
represents an alkyl radical or a hydrogen atom;
R
10
represents a phenyl or heteroaryl group optionally substituted with one or more halogen atoms or groups such as OH, —O-alkyl, —S-alkyl, cyano or alkyl;
R
11
and R
12
represent, independently of each other, a hydrogen or halogen atom and possibly CN or NO
2
, but with H or halogen being preferred;
R
13
represents a halogen atom or a haloalkyl, haloalkoxy, S(O)
q
CF
3
or SF
5
group;
m, n, q and r represent, independently of each other, an integer equal to 0, 1 or 2;
X represents a trivalent nitrogen atom or a
Frommer William S.
Frommer & Lawrence & Haug LLP
Kowalski Thomas J.
Merial
Pak John
LandOfFree
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