Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-04-11
2004-09-28
Levy, Neil S. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S404000, C514S406000, C424S405000, C424S406000, C424S407000
Reexamination Certificate
active
06797724
ABSTRACT:
Each of the herein cited patent applications, and all documents cited in the text or during the prosecution of the herein cited patent applications (“application cited documents”)—either cited by the Examiner (e.g., Patent Office, such as the U.S. or French Patent Office or WIPO or Searching Authority) or by the applicant(s)—as well as all documents cited or referenced in application cited documents, are hereby incorporated herein by reference. Further, all documents cited herein (“herein cited documents”) and all documents cited or referenced in herein cited documents are hereby incorporated herein by reference.
Further, the following documents are hereby incorporated herein by reference:
U.S. Pat. No. 5,885,607, issued to Jeannin on Mar. 23, 1999;
U.S. Pat. No. 5,801,189, issued to Twinn on Sep. 1, 1998;
U.S. Pat. No. 5,232,940, issued to Hatton on Aug. 3, 1993;
U.S. Pat. No. 5,122,530, issued to Tomioka on Jun. 16, 1992;
U.S. Pat. No. 5,567,429, issued to Senbo on Oct. 22, 1996;
U.S. Pat. No. 4,963,575, issued to Buntain on Oct. 16, 1990;
U.S. Pat. No. 5.516,787, issued to Takada on May 14, 1996;
U.S. Pat. No. 5,629,334, issued to Takada on May 13, 1997;
EP 0 295 117 with an international filing date of Jun. 10, 1988;
PCT/EP98/01224 with an international filing date of Mar. 1, 1998;
PCT/EP97/06503 with an international filing date of Nov. 21, 1997;
Bloomquist, J. R.,
Ion Channels as Targets for Insecticides, Annu. Rev. Entomol
.; Vol. 41,163-90 (1996);
Hainzl, D. et al,
Mechanisms for Selective Toxicity of Fipronil Insecticide and Its Sulfone Metabolite and Desulfinyl Photoproduct, Chem. Res. Toxicol
; Vol. 11(12), 1529-35 (1998);
Hainzi, D. et al,
Fipronil Insecticide: Novel Photochemical Desulfinylation with Retention of Neurotoxicity, Proc. Natl. Acad. Sci. USA
; Nov. 12;93(23), 12764-7 (1996); and Cochet, P. et al,
Skin Distribution of Fipronil by Microautoradiography following Topical Administration to the Beagle Dog, Eur. J. Drug Metab. Pharmacokinet
. Jul-Sep; 22(3): 211-6 (1997).
This invention envisions compounds, compositions, formulations and methods of use involving a phenylpyrazole as depicted herein or in herein cited documents; and phenylpyrazoles depicted herein or in herein cited documents can be used in the compositions, formulations and methods of herein cited patent applications. Further, the invention envisions compounds that degrade, e.g., biodegrade or photodegrade or chemically degrade, to phenylpyrazoles as depicted herein or in herein cited documents or to same or similar derivatives of phenylpyrazoles herein depicted from degradation (e.g., biodegradation, photodegradation, chemical, degradation); for instance, if a herein depicted phenylpyrazole degrades to compound “X”, the invention envisions compounds “X” and other phenylpyrazoles that degrade to compound “X”. The invention also envisions compositions, formulations, and methods of use involving compounds that degrade to phenylpyrazoles as depicted herein or in herein cited documents or to same or similar derivatives of phenylpyrazoles herein depicted from degradation; for example, pour-on formulations, spot-on formulations, formulations and/or methods for distribution in sebacious glands, formulations and/or methods of preventing, treating, controlling, and/or combating myasis, and the like, as well as in compositions, formulations, and uses of herein cited patent applications. (A compound that degrades to a phenylpyrazole herein depicted or that degrades to a same or similar derivative of a phenylpyrazole herein depicted from degradation, e.g., a phenylpyrazole that degrades to compound “X” that is a degradation derivative of a herein depicted phenylpyrazole is herein termed a “pro-pp-compound”.) More in particular, herein depicted phenylpyrazoles as well as those of documents cited herein, e.g. PCT/EP97/06503 or WO 98/24769, which is equivalent to U.S. Pat. No. 6,265,430, degrade to the active compound fipronil sulfide (sulfide on the 4 position) and thus, the invention comprehends the use of phenylpyrazoles depicted herein and in documents cited herein that degrade to fipronil sulfide, in for example, pour-on formulations, spot-on formulations, formulations and/or methods for distribution in sebacious glands, formulations and/or methods of preventing, treating, controlling, and/or combating myasis, and the like, as well as in compositions, formulations, and uses of herein cited patent applications. Ethaprol (or a 4-elhylsulfoxide derivative of herein depicted phenylpyrazole) as well as compounds of the herein formula wherein there is a sulfideat the 4 position and/or R
1
═CN, SO and/or R
3
═CF
3
or alkyl (e.g., 4-haloalkyl sulfoxide sulfones, 3-cyanos, 3-cyano-pro-pp-compounds) are useful, e.g., in pour-on formulations and methods. Formulations, compositions and methods of use can include an additional active ingredient, such as a macrolide antibiotic and/or an insect growth regulator (IGR), or the like, which can be admixed with or administered separately from, e.g., sequentially, with the phenylpyrazole and/or pro-pp-compound (or the macrolide antibiotic and/or IGR can itself, without the phenylpyrazole and/or pro-pp-compound, be the active ingredient in the formulation, such as pour-on or spot-on formulation or a formulation for distribution in the sebacious glands, as disclosed herein arm herein cited patent applications). These and other embodiments are provided in this text.
The present invention relates to a direct pour-on skin solution which contains an antiparasitic product and is intended to be applied topically to cattle and sheep.
The invention also relates to the use of antiparasitic compounds for the preparation of this skin solution, as well as to a treatment process relating thereto.
Cattle and sheep are affected by a large number of parasites.
The main ones are ticks of the genus Boophilus, among which mention may be made of the species
microplus
(cattle tick),
decoloratus
and
anulatus.
The other main parasites of cattle and sheep are indicated in order of decreasing importance:
myiases such as
Dermatobia hominis
(known as Berne in Brazil) and
Cochlyomia hominivorax
(greenbottle); sheep myiases such as
Lucilia sericata, Lucilia cuprina
(known as blowfly strike in Australia, New Zealand and South Africa). These are flies whose larva constitutes the animal parasite.
flies proper, namely those whose adult constitutes the parasite, such as
Haematobia irritans
(horn fly).
lice such as
Linognathus vitulorum
, etc.
galls such as
Sarcoptes scabiei
and
Psoroptes ovis.
Ticks, in particular
Boophilus microplus
, are very closely attached to the pasture in which they live and are particularly difficult to control.
There is at the present time no truly effective method for controlling ticks, and less still an effective way of controlling the set of parasites indicated above.
WO-A-87/3781, EP-A-295,117 and EP-A-500,209 describe a class of insecticides which are N-phenyl-pyrazole derivatives. These compounds are given as having activity against a very large number of parasites, including
Boophilus microplus
, in fields as varied as agriculture, public health and veterinary medicine. The general teaching of these documents indicates that these insecticidal compounds may be administered via different routes; oral, parenteral, percutaneous and topical routes. Topical administration comprises, in particular, oral formulations, baits, dietary supplements, skin solutions (pour-on), solutions for spraying (sprays), baths, showers, jets, powders, greases, shampoos, creams, etc. The pour-on type skin solutions are designed for percutaneous administration. Example 9 of EP-A-295,117 and Example 29I of EP-A-500,209 describe a pour-on type skin solution containing 15% insecticide and 85% dimethyl sulphoxide, for percutaneous administration of the insecticide.
EP-A-296,381 also describes pyrazole compounds having insecticidal activity in the field of agriculture, public health and veterinary medicine.
Boophilus microplus
is one of the very many targets mentioned.
Etchegaray Jean-Pierre
Jeannin Philippe
Frommer & Lawrence & Haug LLP
Kowalski Thomas J.
Levy Neil S.
Merial
Russell Mark W.
LandOfFree
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