Parasiticidal combination

Details Parasiticidal combination Parasiticidal combination

1999-03-17

2002-11-19

Levy, Neil S. (Department: 1616)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C424S405000, C424S407000, C424S078020, C514S030000, C514S407000

Reexamination Certificate

active

06482425

ABSTRACT:

The present invention relates to an improvement to methods for combating animal parasites, namely parasites of small mammals and of birds and in particular ectoparasitical insects and endoparasites, in particular filariae and worms.
It also relates to a new composition for this use, on the basis of a combination in which already known parasiticides are synergically combined. Finally, it relates to the use of such already known parasiticides in the preparation of a composition for combating parasites and in particular the abovementioned combinations of parasites.
A new family of insecticides based on 1-N-phenylpyrazoles has been described in Patents EP-A-295,217 and EP-A-352,944. The compounds of the families defined in these patents are extremely active and one of these compounds, 1-[2,6-Cl
2
-4-CF
3
phenyl]-3-CN-4-[SO-CF
3
]-5-NH
2
pyrazole, the common name of which is fipronil, has proved to be particularly effective, not only against crop parasites but also against ectoparasites of mammals and in particular, but not exclusively, fleas and ticks.
Endectocidal compounds exhibiting a degree of activity against endoparasites and comprising avermectins and their derivatives and related products, such as ivermectin, are also known. Such substances are, for example, described in U.S. Pat. Nos. 3,950,360 and 4,199,569.
Provision has often been made to combine parasiticides with the aim of broadening the antiparasitical spectrum and the combination of the abovementioned 1-N-phenylpyrazole derivatives with avermectins, ivermectins and milbemycin had already been mentioned, among many others, without, all the same, determining the specific advantage which such a combination might have, taking into account the numerous and complex host-parasite interactions.
Patent Application AU-A-16 427/95 mentions the combination of a substituted 1-N-pyrazole derivative of this type with avermectins, ivermectin or moxidectin, among a very large number of insecticides or parasiticides of various types, including fipronil moreover, without, however, giving information on a composition comprising such a combination and without establishing a distinction regarding the targets susceptible to being targeted by specific combinations, among the innumerable parasites which can potentially be attacked.
Apart from a very general teaching, the prior art thus does not make it possible to distinguish, in each specific case, the animals and the parasites for which a specific combination might be useful or the form of a composition containing such a combination.
Moreover, the prior art is silent with respect to the presentations, dosages, posologies and administration routes of combinations of these parasiticides, the sites, methods of effect, duration of effect and targets of which are very different.
The invention intends in particular to improve methods for combating parasites of small mammals, and in particular cats and dogs, with the aim of ridding these animals of all the parasites commonly encountered.
The invention intends in particular to provide for effective and lasting destruction of ectoparasites, such as fleas and ticks and possibly itch mites and lice, and of endoparasites, such as filariae, in particular dirofilariae, and roundworms of the digestive tract, in cats and dogs.
The following are in particular targeted among roundworms or nematodes: ascarids (in particular Toxocara canis), ancylostoma species (in particular Ancylostoma caninum) and Echinococcus and Trichuris species, in particular Trichuris vulpis.
A particular object of the invention is to use already known parasiticides to prepare a composition which is extremely active against fleas and, if appropriate, against ticks.
Another object of the invention is to produce such compositions which make it possible, inter alia, effectively to combat certain endoparasites and in particular filariae and/or roundworms.
The very high effectiveness of the method and of the composition according to the invention implies not only high instantaneous effectiveness but also an effectiveness of very long duration after the treatment of the animal.
Flea within the meaning of the present invention is understood to mean in particular the Ctenocephalides species, in particular felis and canis.
Filaria is understood to mean in particular Dirofilaria immitis.
Toxocara canis, Ancylostoma caninum and Trichuris vulpis are understood in particular among the other nematodes.
The subject of the invention is a method for combating parasites and in particular ectoparasites and, preferably, also endoparasites of small mammals and in particular dogs and cats, characterized in that the animal is treated, preventively or curatively, by administration in effectively parasiticidal doses and proportions, on the one hand, of at least one compound (A) belonging to the 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;
R
4
represents a hydrogen or halogen atom or an NR
5
R
6
, S(O)
m
R
7
, C(O)R
7
or C(O)OR
7
, alkyl, haloalkyl or OR
8
radical or an —N═C (R
9
) (R
10
) radical;
R
5
and R
6
independently represent a hydrogen atom or an alkyl, haloalkyl, C(O)alkyl, S(O)
r
CF
3
or alkoxycarbonyl radical or R
5
and R
6
can together form a divalent alkylene radical which can be interrupted by one or two divalent heteroatoms, 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 by 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 one another, a hydrogen or halogen atom and optionally CN or NO
2
, but 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 one another, an integer equal to 0, 1 or 2;
X represents a trivalent nitrogen atom or a C-R
12
radical, the three other valencies of the carbon atom forming part of the aromatic ring;
with the proviso that, when R
1
is methyl, then either R
3
is haloalkyl, R
4
is NH
2
, R
11
is Cl, R
13
is CF
3
and X is N or else R
2
is 4,5-dicyanoimidazol-2-yl, R
4
is Cl, R
11
is Cl, R
13
is CF
3
and X is C—Cl
and, on the other hand, of at least one compound (B) formed of an endectocidal parasiticide of macrocyclic lactone type.
The parasiticide (B) is preferably selected from the group formed by avermectins, ivermectin, abamectin, doramectin, moxidectin, milbemycins and the derivatives of these compounds.
The structure, the characteristics and the processes for the manufacture of the compounds of type (B) are well known to a person skilled in the art and reference can be made to the widely available technical and commercial literature. For avermectins, ivermectin and abamectin, reference may be made, for example, to the work “Ivermectin and Abamectin”, 1989, by M. H. Fischer and H. Mrozik, William C. Campbell, published by Springer Verlag., or Albers-Schonberg et al. (1981), “Avermectins Structure Determination”, J. Am. Chem. Soc., 103, 4216-4221. For doramectin, “Veterinary Parasitology”, vol. 49, No. 1, July 1993, 5-15 may in particular be consulted. For milbemycins, reference may be made, inter alia, to Davies H. G. et al., 1986, “Avermectins and Milbemycins”, Nat. Prod. Rep., 3, 87-121, Mrozik H. et al., 1983, Synthesis of Milbemycins from Avermectins, Tetrahedron Lett., 24, 5333-5336, and U.S. Pat. No. 4,134,973.
Compounds (B) can be either natural products or are semi-synthetic derivatives thereof. The structure of at least certain compounds (B) are closely related, e.g., by sharing a complex 16-membered macrocyclic lactone ring. The natural product avermectins are disclosed in U.S. Pat. No. 4,310,519 to Albers-Schonberg, et al., and the 22, 23-dihydro avermectin compounds are disclosed in Chabala, et al., U.S. Pat.

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