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WO2001014340A1 - Agents de lutte contre les maladies animales causees par des endoparasites - Google Patents

Agents de lutte contre les maladies animales causees par des endoparasites Download PDF

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Publication number
WO2001014340A1
WO2001014340A1 PCT/JP2000/005567 JP0005567W WO0114340A1 WO 2001014340 A1 WO2001014340 A1 WO 2001014340A1 JP 0005567 W JP0005567 W JP 0005567W WO 0114340 A1 WO0114340 A1 WO 0114340A1
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WIPO (PCT)
Prior art keywords
group
optionally substituted
alkyl
substituted
atom
Prior art date
Application number
PCT/JP2000/005567
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English (en)
Japanese (ja)
Inventor
Kyuya Morino
Shuichi Yotsuya
Masayuki Morita
Original Assignee
Ishihara Sangyo Kaisha, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ishihara Sangyo Kaisha, Ltd. filed Critical Ishihara Sangyo Kaisha, Ltd.
Priority to AU65973/00A priority Critical patent/AU6597300A/en
Publication of WO2001014340A1 publication Critical patent/WO2001014340A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to an agent for controlling animal diseases caused by internal parasites, which contains a specific pyridine compound or a salt thereof as an active ingredient.
  • the animal disease controlling agent is useful, for example, as an agent for controlling a parasite such as coccididium which is parasitic on the body of an animal.
  • various pest control agents and insecticides have been used for endoparasites of animals such as livestock, poultry and pets.
  • it is an endoparasitic protozoan belonging to the genus Eimeria and is widely used in various livestock and poultry such as chickens for controlling coccididium.
  • a sulfa agent for example, a sulfa agent; a quinoline agent; an antithiamine agent; And polyether antibiotics such as salinomycin, lasalocid, etc .;
  • animal diseases caused by endoparasites are caused by parasites parasitizing the body of an animal host. Endoparasites that cause animal diseases often infest livestock, poultry, and pets in the stomach, intestinal tract, lungs, heart, liver, blood vessels, subcutaneous, and lymphoid tissues, causing serious conditions. Animal diseases caused by endoparasites cause anemia, malnutrition, weakness, weight loss, damage to the intestinal tract wall and other tissues and organs, and if left untreated, hosts infected with endoparasites will die.
  • coccidiosis one of the animal diseases caused by endoparasites, causes enormous economic loss, especially in the poultry industry. In addition to chickens, it is one of the diseases that causes problems when raising cattle, sheep, rabbits, dogs and cats. Therefore, coccidiosis Control can have tremendous benefits in the poultry industry, the livestock industry, and pet care. Then, based on such a concept, the present invention provides an agent for controlling animal diseases caused by endoparasites.
  • the present inventors have enthusiastically searched for compounds that can control animal diseases caused by endoparasites, particularly coccidiosis. As a result, they have found that a specific pyridine compound or a salt thereof, which has been found to be used for agricultural chemicals, has an effect of controlling animal diseases caused by endoparasites, and completed the present invention.
  • the present invention provides a compound represented by the general formula (I):
  • M is 0 or 1
  • Q is
  • R ′ and R 2 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, Good cycloalkyl group,-(UW 1 )! ⁇ Group, -S (O)
  • R 1 D group C (R 9 ) R 1 D group, or a nitrogen atom with an adjacent nitrogen atom or It may form a 5- or 6-membered heterocyclic group having 4 to 5 carbon atoms which may contain an oxygen atom
  • R 3 may be an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted good ⁇ Rukiniru group, an optionally substituted cycloalkyl group, an optionally substituted Ariru group, an alkoxy group, an alkylthio group or a mono- or dialkylamino group
  • R 4 is an alkyl or dialkylamino group
  • Z is N or - C-R 6 group
  • R 6 is a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkyl
  • R 9 and R ID are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted heterocyclic group, —N— (R M ) R 12 group, R u and R 12 are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkylthio group; Alkynyl group, optionally substituted aryl
  • the present invention relates to an agent for controlling animal diseases caused by internal parasites, which comprises a compound or a salt thereof as an active ingredient.
  • Y represents CF 3 , CHF 2 , CH 2 F, CF 2 C 1, CFC 1 2 ,
  • CC 1 3, CH 2 CF 3 , CF 2 CF 3 includes a haloalkyl group such as CHB r 2, C HB r. Among them, a haloalkyl group having 1 to 2 carbon atoms and 1 to 5 halogen atoms is desirable, and a trifluoromethyl group is more desirable.
  • R 3 R 6 R 7, R 8, R 9, R, R u or alkyl group which may be substituted is defined as R 12;
  • R 8 , R 11 or R 12 and the optionally substituted cycloalkyl group defined as R 1 , R 2 or R 3 halogen may be used.
  • substituent When the above substituent is an imino group, it may form an amidino group or an imidate group together with an amino group or an alkoxy group.
  • substituent of an alkyl group which may be substituted and defined as R ′ or R 2 contained in the group Q 1 in the general formula (I) for example, 4-haloalkyl-3-pyridinyl lipoxamide Groups, N-methyl-4-haloalkyl-l-pyridinecarboxamide groups, 4-haloalkyl-3-pyridinecarboxamide-N-alkyleneoxy groups, and the like.
  • the chemical structural formula of the general formula (I) containing these substituents is shown below.
  • R 2 are as defined above, A is - (CH 2), - group or - (CH 2) q -0 - (CH 2) q - group wherein 1 is an integer from 1 to 4 And Q is 1 or 2. That is, the above compound is a dimer of the compound of the general formula (I) linked by an alkylene chain or the like.
  • the active ingredient of the animal disease controlling agent of the present invention includes a trimer based on such a concept.
  • R 3 Defined as R 3, R 7, R 8 , R u or R 12 included in the Q 1 group in the general formula (I)
  • the secondary substituent of the substituted aryl group include a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, a cycloalkyl group, a cycloalkoxy group, an alkoxycarbonyl group, and an alkyl group.
  • Examples thereof include a sulfonyl group, an alkylcarbonyloxy group, an aryl group, an aryloxy group, an arylthio group, an amino group, an amino group substituted with one or two alkyl groups, a cyano group, a nitro group, and a hydroxy group.
  • the tertiary substituent of the optionally substituted heterocyclic group defined as the secondary substituent in the Q 1 group includes a halogen atom, an alkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, a phenyl group.
  • the phenyl group may be substituted with a halogen atom, an alkyl group, an alkoxy group, a nitro group, a haloalkyl group or a phenoxy group), a phenoxy group, a phenylthio group, a cycloalkyl group, a cycloalkoxy group and the like.
  • the alkyl group or alkyl moiety contained in the Q 1 group in the general formula (I) includes those having 1 to 6 carbon atoms, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
  • Those having 3 or more carbon atoms may be straight-chain or branched-chain structural isomers.
  • the alkenyl group contained in R 1 or R 2 has 2 to 6 carbon atoms, for example, ethenyl group, propenyl group, butenyl group, pentenyl group, hexenyl group, and has 3 or more carbon atoms. May be straight-chain or branched-chain structural isomers.
  • the alkynyl group contained in R 1 or R 2 has 2 to 6 carbon atoms, for example, ethynyl group, propynyl group, butyl group, pentynyl group, hexynyl group, and has 3 or more carbon atoms.
  • cycloalkyl group contained in R 1 or R 2 include those having 3 to 8 carbon atoms, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group.
  • R 1 and R 2 contained in the Q 1 group in the general formula (I) may be taken together and may contain a nitrogen atom or an oxygen atom together with an adjacent nitrogen atom.
  • the ring group include a morpholino group, a pyrrolidino group, a piperidino group, Examples thereof include a midazolidinyl group, 2-cyanoimino-3-methyl-1-imidazolidinyl group, 1-piperazinyl group and 4-methyl-1-piperazinyl group.
  • Examples of the aryl group included in the Q 1 group in the general formula (I) include a phenyl group, a phenyl group, a furanyl group, a pyridyl group, a naphthyl group, a benzophenyl group, a benzofuranyl group, and a quinolinyl group.
  • the heterocyclic moiety of the optionally substituted heterocyclic group contained in the Q 1 group in the general formula (I) includes a pyridyl group, a phenyl group, a furyl group, a virazinyl group, a thiazolyl group, an isooxazolyl group, and a quinolyl group
  • the heterocyclic moiety of the optionally substituted heterocyclic group represented by Q in the general formula (I) includes 2 to 3 hetero atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom.
  • a monocyclic group is preferably a membered member, and specific examples include a pyrazolyl group, an oxazolyl group, a thiazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a triazolyl group.
  • the secondary substituent of the optionally substituted heterocyclic group represented by Q in the general formula (I) includes a halogen atom, a nitro group, an optionally substituted alkyl group, an optionally substituted alkenyl group, Alkynyl group which may be substituted, aryl group which may be substituted, heterocyclic group which may be substituted, cycloalkyl group which may be substituted, hydroxyl group, alkoxy group which may be substituted, alkenyl which may be substituted Oxy group, optionally substituted alkynyloxy group, optionally substituted aryloxy group, optionally substituted heterocyclic oxy group, optionally substituted cycloalkoxy group, mercapto group, optionally substituted Alkylthio group, optionally substituted arylthio group, optionally substituted alkoxylthio group, optionally substituted alkynylthio group, optionally substituted An optionally substituted heterocyclic thio group, an optionally substituted
  • those which may be substituted are halogen atoms; cyano groups; alkyl groups which may be substituted with halogen atoms, haloalkyl groups, cyano groups, alkoxy groups, aryl groups; halogen atoms, aryl groups.
  • An alkoxy group optionally substituted with: a hydroxyl group; an alkylsulfonyl group, an arylalkyl group, a heterocyclic alkyl group, an alkyl group, an aryl group, an alkylaryl group, an alkylhydroxy group, a cyanoalkyl group, an alkynyl group, and an alkenyl group
  • An amino group optionally substituted with a cycloalkyl group; an alkoxy group, an alkylamino group, a carbonyl group optionally substituted with an alkyl group; an alkylthio group; an aryloxy group; an arylthio group; a halogen atom, a haloalkoxy group, or an alkyl Or aryl which may be substituted with aryl group A nitro group; an arylcarboxy group optionally substituted by a halogen atom or a nitro group; a cycloalkyl group; an
  • An aryl isocyanato group which may be substituted; an alkyl group, an alkoxy group, A heterocyclic group which may be substituted by an aryl group or an ester group; which may be substituted by a tertiary substituent such as an alkoxyisocyano group.
  • the secondary substituent of the optionally substituted heterocyclic group represented by Q in the general formula (I), the alkyl group or the alkyl moiety in the tertiary substituent are those having 1 to 6 carbon atoms, for example, Examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group, and those having 3 or more carbon atoms may be straight-chain or branched-chain structural isomers.
  • alkenyl group examples include those having 2 to 6 carbon atoms, such as ethenyl group, propyl group, butenyl group, pentenyl group, and hexenyl group, and those having 3 or more carbon atoms are straight or branched. It may have a structural isomer of the chain.
  • Alkynyl groups include those having 2 to 6 carbon atoms, for example, ethynyl group, propynyl group, butynyl group, pentynyl group and hexynyl group, and those having 3 or more carbon atoms are linear or branched.
  • Examples of the cycloalkyl group include those having 3 to 8 carbon atoms, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group.
  • Examples of the aryl group include a phenyl group, a phenyl group, a furanyl group, a pyridyl group, a naphthyl group, a benzophenyl group, a benzofuranyl group, and a quinolinyl group.
  • heterocyclic group examples include 1 to 3 heteroatoms selected from nitrogen, oxygen and sulfur, such as pyridyl, phenyl, phenyl, virazinyl, thiazolyl, isoxazolyl, and quinolyl. And a 5- or 6-membered monocyclic group or a phenyl-fused cyclic group.
  • the compound of the general formula (I) may form a salt with an acidic substance or a basic substance, and the salt with the acidic substance may be a salt such as hydrochloride, hydrobromide, phosphate, sulfate, or nitrate.
  • the salt with a basic substance may be an inorganic or organic base salt such as a sodium salt, a potassium salt, a calcium salt, an ammonium salt or a dimethylamine salt.
  • R 1 and R z are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, Cycloalkyl group, -C (W 3 R group, -S ( ⁇ ) group,
  • R 1 and R 2 together form a C (R 9 ) R ie group, or a nitrogen or oxygen atom with an adjacent nitrogen atom May form a 5- or 6-membered heterocyclic group having 4 to 5 carbon atoms, wherein R 3 is an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted A alkynyl group, a cycloalkyl group which may be substituted, an aryl group which may be substituted, an alkoxy group, an alkylthio group or a mono- or dialkylamino group, R 4 is an alkyl group or a dialkylamino group, and R 5 is an alkyl group Z is an N or —C—R 6 group, R 6 is a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkylthio group or a nitro group,
  • R 9 and R 1 Q each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted heterocyclic group, — N _ (R M )
  • R 12 group R 11 and R 12 are each independently a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, or an alkyl group which may be substituted.
  • R 3 is location Alkyl group which may be substituted, alkenyl group which may be substituted, alkynyl group which may be substituted, cycloalkyl group which may be substituted, aryl group which may be substituted, alkoxy group, alkylthio group or mono- or dialkyl amino groups der Ri
  • R 4 is an alkyl group Other is a dialkylamino group
  • R 5 is an alkyl or Ariru group
  • R 9 and R 1 fl are each independently an alkoxy group or an alkyl Chio group
  • W 1 is an oxygen atom or a sulfur atom, n Is 1 or 2.) or a salt thereof according to the above (1).
  • R 1 and R 2 are each independently a hydrogen atom, an alkyl group which may be substituted, or —C (W is a R 3 group, or R 1 and R 2 are- ⁇ (R 6 ) forms a R 7 group, W 1 is an oxygen atom or a sulfur atom, R 3 is an optionally substituted alkyl group, an optionally substituted aryl group or an alkoxy group, R 6 and The compound of the above (1), (2) or (3), wherein R 7 is independently an alkoxy group or an alkylthio group, or a salt thereof.
  • R 1 is a hydrogen atom
  • R 2 is
  • Z is an N or —C—R 6 group
  • R 6 is a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, an alkylthio group or a nitro group. Or the compound of (3) or a salt thereof.
  • X is an oxygen atom
  • R 1 and R 2 are each independently a hydrogen atom, an alkyl group, an alkoxyalkyl group, an alkylaminoalkyl group, a C 2 _ 6 cyclic aminoalkyl group, a hydroxyalkyl group, a cyanoalkyl group, A thiocarbamoylalkyl group, an alkylcarbonyloxyalkyl group, an alkylcarbonyl group, an arylcarbonyl group, a trifluoromethyl-substituted arylcarbonyl group, an alkoxythiocarbonyl group or an alkoxycarbonyl group, or R 1 and R 2
  • a 5-membered monocyclic group containing 2 to 3 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom is a pyrazolyl group, an oxazolyl group, a thiazolyl group, an oxazidiazolyl group, a thiadiazolyl group or
  • N-cyanomethyl-14-trifluoromethyl-3-pyridinepyridine compound No. 1
  • N-ethyl-4-trifluoromethyl-3 —Pyridine power Lupoxamide Compound No.2
  • 4-Trifluoromethyl—3-Pyridinecarboxamide 1-oxide Compound No.3
  • 4-Trifluoromethyl-13-pyridinecarboxamide N-thiocal Bamoylmethyl-4-trifluoromethyl-3-pyridinecarboxamide, N-ethoxymethyl-4-trifluoromethyl-3-pyridinepyridine, lipoxamide N-isopropylaminomethyl-4-trifluoromethyl-3-pyridinecarbo Oxamide, N-cyanomethyl-N, N-bis (4-trifluoromethylnicotinoyl) amine, N-acetyl-N-cyanomethyl- 4-trifluoromethyl-3-Pyridinecarboxamide, N-cyanomethyl-N- Me
  • the agent for controlling an animal disease caused by an endoparasite of the present invention includes nematodes such as lungworm, benthic, nodular worm, stomach parasite, roundworm, and filamentous worm; tapeworm; fluke; It is effective against parasites in the host animal, such as protozoa such as endospores, toxoplasma, and cryptosporidium.
  • protozoa such as endospores, toxoplasma, and cryptosporidium.
  • coccidium that infests poultry (chicken, ducks, geese, turkeys, etc.).
  • coccidium parasitizing poultry For example, Eimeria tenella, Eimer acervulina, Eimeria brunetti, Eimeria maxima, Eimeria mitis, Eimeria nevice ) And Eimeria praecox.
  • the compound of the general formula (I) may be used as it is, but it should be used in the form of powders, granules, tablets, powders, capsules, premixes, solutions, emulsions, etc. together with a suitable carrier.
  • Suitable carriers are those usually used in feed drugs, such as lactose, sucrose, glucose, starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other commercially available feed ingredients And the like.
  • the compound of the present invention may be used in combination with a carrier together with various vitamins, minerals, amino acids, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, preservatives, and the like.
  • the concentration of the compound of formula (I) varies depending on the method of administration, the purpose of the administration, the disease symptoms, etc., but it is usually advisable to formulate the compound in a feed so that the concentration is at least 0.1 ppm. Appropriate.
  • a specific pyridine compound can be provided as an agent for controlling animal diseases caused by endoparasites.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette invention se rapporte à des agents de lutte contre les maladies causées par des endoparasites, ces agents contenant comme principe actif des composés représentés par la formule générale (I) où Y représente haloalkyle; m est égal à 0 ou à 1; et Q représente la formule (II) (où X représente O ou S; R1 et R2 représentent chacun H, alkyle éventuellement substitué, alcényle éventuellement substitué, alcynyle éventuellement substitué, cycloalkyle éventuellement substitué, -C(W1)R3, -S(O), R4, -NHR5, la formule (III), -C(R7) ou =NO-R8, ou alors R1 et R2 peuvent former ensemble =C(R9)R10 ou, avec l'atome d'azote adjacent, un hétérocycle à 5 ou 6 éléments, où R3 représente alkyle éventuellement substitué, etc; R4 représente alkyle, etc; R5 représente alkyle, etc; Z représente N ou -C-R6 (où R6 représente H, halogéno, alkyle éventuellement substitué, etc.); R7 et R8 représentent séparément chacun H, alkyle éventuellement substitué, etc; R9 et R10 représentent chacun séparément H, alkyle éventuellement substitué, etc; W1 représente O ou S; et n est égal à 1 ou à 2) ou un hétérocycle éventuellement substitué.
PCT/JP2000/005567 1999-08-19 2000-08-18 Agents de lutte contre les maladies animales causees par des endoparasites WO2001014340A1 (fr)

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JP11/233256 1999-08-19
JP23325699 1999-08-19

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002053544A1 (fr) * 2000-12-29 2002-07-11 Darwin Discovery Ltd. Utilisations pharmaceutiques et synthese de nicotinanilide-n-oxydes
WO2003097604A1 (fr) * 2002-05-16 2003-11-27 Bayer Cropscience Gmbh Derives de pyridine carboxamide et leur utilisation en tant que pesticides
JP2005536468A (ja) * 2002-05-16 2005-12-02 バイエル クロップサイエンス ゲーエムベーハー 農薬ピリジンカルボキサミド誘導体
WO2014034750A1 (fr) * 2012-08-30 2014-03-06 国立大学法人 東京大学 Agent de lutte contre les endoparasites
WO2014034751A1 (fr) * 2012-08-30 2014-03-06 国立大学法人 東京大学 Agent de lutte contre les endoparasites et son utilisation
US10117969B2 (en) 2008-06-26 2018-11-06 Nobelpharma Co., Ltd. Agent for regenerating tympanic membrane or external auditory canal

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51148032A (en) * 1975-06-12 1976-12-18 Sankyo Co Ltd Agents for coccidiosis
JPH10101648A (ja) * 1996-09-26 1998-04-21 Ishihara Sangyo Kaisha Ltd アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤
EP0878192A2 (fr) * 1997-05-01 1998-11-18 Allegheny University of The Health Sciences Méthodes de traitement d'infections protozoaires
WO1998057969A1 (fr) * 1997-06-16 1998-12-23 Hoechst Schering Agrevo Gmbh 4-haloalkyl-3- heterocyclylpyridines et 4-haloalkyl -5-heterocyclylpyrimidines, leurs procedes de preparation, produits les contenant et leur utilisation comme pesticides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS51148032A (en) * 1975-06-12 1976-12-18 Sankyo Co Ltd Agents for coccidiosis
JPH10101648A (ja) * 1996-09-26 1998-04-21 Ishihara Sangyo Kaisha Ltd アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤
EP0878192A2 (fr) * 1997-05-01 1998-11-18 Allegheny University of The Health Sciences Méthodes de traitement d'infections protozoaires
WO1998057969A1 (fr) * 1997-06-16 1998-12-23 Hoechst Schering Agrevo Gmbh 4-haloalkyl-3- heterocyclylpyridines et 4-haloalkyl -5-heterocyclylpyrimidines, leurs procedes de preparation, produits les contenant et leur utilisation comme pesticides

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002053544A1 (fr) * 2000-12-29 2002-07-11 Darwin Discovery Ltd. Utilisations pharmaceutiques et synthese de nicotinanilide-n-oxydes
US7141590B2 (en) 2000-12-29 2006-11-28 Ucb Sa Pharmaceutical uses and synthesis of nicotinanilide-N-oxides
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JP2005536468A (ja) * 2002-05-16 2005-12-02 バイエル クロップサイエンス ゲーエムベーハー 農薬ピリジンカルボキサミド誘導体
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JPWO2014034750A1 (ja) * 2012-08-30 2016-08-08 国立大学法人 東京大学 内部寄生虫防除剤
US9550749B2 (en) 2012-08-30 2017-01-24 The University Of Tokyo Endoparasite control agent and method for using the same
US9562034B2 (en) 2012-08-30 2017-02-07 The University Of Tokyo Endoparasite control agent
EP3143994A1 (fr) * 2012-08-30 2017-03-22 The University of Tokyo Agent de lutte contre les endoparasites et son utilisation
US10017490B2 (en) 2012-08-30 2018-07-10 The University Of Tokyo Endoparasite control agent and method for using the same
WO2014034751A1 (fr) * 2012-08-30 2014-03-06 国立大学法人 東京大学 Agent de lutte contre les endoparasites et son utilisation
WO2014034750A1 (fr) * 2012-08-30 2014-03-06 国立大学法人 東京大学 Agent de lutte contre les endoparasites
EP2891492B1 (fr) * 2012-08-30 2022-11-09 The University of Tokyo Agent de lutte contre les endoparasites

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