DK2710000T3 - Parasiticide dihydroisoxazolforbindelser - Google Patents

Parasiticide dihydroisoxazolforbindelser Download PDF

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DK2710000T3
DK2710000T3 DK12721146.4T DK12721146T DK2710000T3 DK 2710000 T3 DK2710000 T3 DK 2710000T3 DK 12721146 T DK12721146 T DK 12721146T DK 2710000 T3 DK2710000 T3 DK 2710000T3
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trifluoromethyl
thiophene
dihydroisoxazol
carboxamide
dichlorophenyl
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DK12721146.4T
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Zengyun An
Liang Chen
Shuhui Chen
Jean Marie Defauw
Scott Dale Holmstrom
Ping Hu
Chongzhi Tang
William Hunter White
Wentao Wu
Yang Zhang
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Lilly Co Eli
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    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • 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
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  • Agronomy & Crop Science (AREA)
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  • Engineering & Computer Science (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Claims (15)

1. Forbindelse, eller salt deraf, med formel I
hvor A er
n er 0 eller 1; R1 er thienyl eller phenyl, hvor thienyl eller phenyl er substitueret med 2 eller 3 ens eller forskellige halogenatomer; R2 i hver forekomst uafhængigt er hydrogen, CrC5alkyl, C3-C6cycloalkyl eller Ci-C5haloalkyl; R3er
p i hver forekomst uafhængigt er 0 eller 1; R4 er CrC5alkyl, CrC5haloalkyl, CrC5cyanoalkyl, CrC5alkylthio, C3-Cecycloalkyl eventuelt substitueret med hydroxy, halogen eller CrC5alkyl: C3-C5cycloheteroalkyl, eventuelt substitueret med CrC5alkyl, C3-C6cycloalkyl eller Ci-C5haloalkyl: phenyl, thienyl, pyridinyl eller
hvor et af kulstofatomerne i cycloalkylerne, uafhængigt, eller cycloheteroalkyl kan danne en carbonylgruppe, og hvor phenyl, thienyl eller pyridinyl eventuelt er substitueret med halogen eller en carbamoylgruppe; R5er hydroxy,-0-(Ci-C5alkyl) eller
R6 er hydrogen, CrC5alkyl, CrC5haloalkyl, CrC5cyanoalkyl, CrC5alkylthio eller C2-C5alkynyl; eller R2 og R3 er kombineret til dannelse, sammen med det nitrogen, hvortil de er bundet, af
Yi, Y2 og Y3 er kulstof eller nitrogen med højst kun én af Yi, Y2, og Y3 er nitrogen, og, når Y1; Y2 eller Y3 er et kulstof, kan hver være substitueret med CrC5alkyl; R7er hydrogen, halogen, CrC5alkyl eller
R8er hydroxy, -0-(CrC5alkyl) eller R9er CrC5alkyl,
°9 R10 er hydrogen, CrC5alkyl, CrC5haloalkyl. CrC5cyanoalkyl, CrC5alkylthio eller C2-C5 alkynyl.
2. Forbindelse ifølge krav 1, eller et salt deraf, hvor A er
og hvor R2 er hydrogen, og n er 1.
3. Forbindelse ifølge krav 1 eller krav 2, eller et salt deraf, hvor R3er
4. Forbindelse ifølge krav 1, eller et salt deraf, hvor A er
og hvor Y-ι er nitrogen.
5. Forbindelse ifølge krav 4, eller et salt deraf, hvor R7er eller
6. Forbindelse ifølge krav 1, eller et salt deraf, som er 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-((R)-2- oxopyrrolidin-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; N,N-dimethyl-2-(4-{3-[5-(3,4,5-trichlorthiophen-2-yl)-5-trifluormethyl-4,5- dihydroisoxazol-3-yl]-4,5,6,7-tetrahydrobenzo[c]thiophen-1- carbonyl}piperazin-1-yl)-acetamid; ({3-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-4,5,6,7- tetrahydrobenzo[c]thiophen-1-carbonyl}-amino)-eddikesyremethylester; ({3-[5-(3,4,5-trichlorthiophen-2-yl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4,5,6,7-tetrahydrobenzo[c]thiophen-1-carbonyl}-amino)- edd i kesy re m et h yl este r; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo- 2- (2,2,2-trifluorethylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxamid; 3- (5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(3-oxocyclohexyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxylsyre-[2-oxo-1-(2,2,2-trifluorethyl)-pyrrolidin-3-yl]-amid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-((R)-2-oxopyrrolidin-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxamid; N-(2-(cyanomethylamino)-2-oxoethyl)-3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo- 2-(prop-2-ynylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1- carboxamid; N-(2-oxo-2-(2,2,2-trifluorethylamino)ethyl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; N-((R)-2-oxopyrrolidin-3-yl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; N-(2-(cyanomethylamino)-2-oxoethyl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; N-(2-oxo-2-(prop-2-ynylamino)ethyl)-3-(5-(3,4,5-trichlorphenyl)-5- (trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-oxo-2-(2,2,2-trifluorethylamino)ethyl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N- ((R)-2-oxopyrrolidin-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; N-(2-(cyanomethylamino)-2-oxoethyl)-3-(5-(3,5-dichlor-4-fluorphenyl)-5- (trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-oxo-2-(prop-2-ynylamino)ethyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1- carboxamid; N-(2-oxo-2-(2,2,2-trifluorethylamino)ethyl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; N-((R)-2-oxopyrrolidin-3-yl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxamid; N-(2-(cyanomethylamino)-2-oxoethyl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxamid; N-(2-oxo-2-(prop-2-ynylamino)ethyl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; N-(2-oxo-1-(2,2,2-trifluorethyl)pyrrolidin-3-yl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-(2,2,2-trifluorethylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N- ((R)-2-oxopyrrolidin-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1- carboxamid; N-(2-(cyanomethylamino)-2-oxoethyl)-3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-1-(2,2,2-trifluorethyl)pyrrolidin-3-yl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-oxo-2-(prop-2-ynylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1- carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo- 2- (2,2,2-trifluorethylamino)ethyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3- (5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-(ethylamino)-2-oxoethyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-((tetrahydrofuran-2-yl)methyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-(methylthio)ethyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1 -carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(3,3,3-trifluorpropyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(3-hydroxycyclohexyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(5-fluorpyridin-2-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(tetrahydro-2H-pyran-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(thietan-3-yl)-4,5,6,7-tetrahydro-[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(tetrahydro-2H-pyran-4-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; N-(1-cyclopropyl-2-oxopyrrolidin-3-yl)-3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; N-(2-oxo-2-(prop-2-ynylamino)ethyl)-3-(5-(3,4,5-trichlorthiophen-2-yl)-5- (trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; N-(2-oxo-1-(2,2,2-trifluorethyl)pyrrolidin-3-yl)-3-(5-(3,4,5-trichlorphenyl)-5- (trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; N-(tetrahydro-2H-pyran-4-yl)-3-(5-(3,4,5-trichlorphenyl)-5-(trifluormethyl)-4,5- dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; N-(1-cyclopropyl-2-oxopyrrolidin-3-yl)-3-(5-(3,4,5-trichlorphenyl)-5- (trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1-carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(4-oxocyclohexyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-1-(2,2,2-trifluorethyl)pyrrolidin-3-yl)-4,5,6,7-tetrahydrobenzo[c]-thiophen-1 -carboxamid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(tetrahydro-2H-pyran-4-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; N-(1-cyclopropyl-2-oxopyrrolidin-3-yl)-3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(4-oxocyclohexyl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxamid; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-1-(2,2,2-trifluorethyl)pyrrolidin-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxamid; 3-((R)-5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-((R)-2-oxopyrrolidin-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-((S)-5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-((R)-2-oxopyrrolidin-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; N-(4-carbamoylphenyl)-3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; 3-[5-(3,4,5-trichlorthiophen-2-yl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxylsyre-(3-carbamoyl-thiophen-2-yl)-amid; 2- (3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamido)-eddikesyre; ({3-[5-(3,4,5-trichlorthiophen-2-yl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4,5,6,7-tetrahydrobenzo[c]thiophen-1-carbonyl}-amino)-eddikesyre; N-(2-(cyanomethylamino)-2-oxoethyl)-3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1- carboxamid; 3- (5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo- 2- (prop-2-ynylamino)ethyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxamid; N-(2-(cyanomethylamino)-2-oxoethyl)-3-(5-(3,4,5-trichlorthiophen-2-yl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen- 1- carboxamid; (S)-3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-(2,2,2-trifluorethylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; 3- [5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-5,6-dihydro-4/-/cyclopenta[c]thiophen-1-carboxylsyre[(2,2-difluorethylcarbamoyl)-methyl]-amid; 3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-5,6- dihydro-4H-cyclopenta[c]thiophen-1-carboxylsyre[(2-fluorethylcarbamoyl)- methyl]-amid; (S)-3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxylsyre[(2-fluorethyl- carbamoyl)-methyl]-amid; 3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N- (2-oxo-2-(prop-2-ynylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]thiophen-1- carboxamid; (S)-3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-(prop-2-ynylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid; 3-(4-chlorbenzo[b]thiophen-2-yl)-5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5- dihydroisoxazol; 2- [5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]thieno[2,3-c]pyridin; 5-brom-2-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3- yl]thieno[2,3-b]pyridin; 2- [5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-thieno[2,3-b]pyridin; 3- (benzo[b]thiophen-2-yl)-5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol; 3-(benzo[d]thiazol-2-yl)-5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5- dihydroisoxazol; 5-(3,5-dichlorphenyl)-3-(3-methylbenzo[b]thiophen-2-yl)-5-(trifluormethyl)-4,5- dihydroisoxazol; 5-(3,5-dichlorphenyl)-3-(5-methylbenzo[b]thiophen-2-yl)-5-(trifluormethyl)-4,5- dihydroisoxazol; 3-(5-chlorbenzo[b]thiophen-2-yl)-5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5- dihydroisoxazol; methyl-2-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3- yl)thieno[2,3-b]pyridin-5-carboxylat; 2-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]thieno[2,3- b]pyridin-5-carboxylsyre; 2-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo- 2-(2,2,2-trifluorethylamino)ethyl)thieno[2,3-b]pyridin-5-carboxamid; eller 2-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-((R)-2-oxopyrrolidin-3-yl)thieno[2,3-b]pyridin-5-carboxamid.
7. Forbindelse ifølge krav 1, eller et salt deraf, som er (S)-3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 5,6-dihydro-4/-/-cyclopenta[c]thiophen-1-carboxylsyre[(2,2- difluorethylcarbamoyl)-methyl]-amid).
8. Forbindelse ifølge krav 1, eller et salt deraf, som er (S)-3-(5-(3,5-dichlor-4-fluorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-N-(2-oxo-2-(prop-2-ynylamino)ethyl)-5,6-dihydro-4H-cyclopenta[c]-thiophen-1 -carboxamid.
9. Forbindelse, som er 3-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-4,5,6,7-tetrahydrobenzo[c]thiophen-1 -carboxylsyre (1,1 -dioxothietan-3-yl)-amid; 3-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-4,5,6,7-tetrahydrobenzo[c]thiophen-1 -carboxylsyre(1,1 -dioxohexahydro-116-thiopyran-4-yl)-amid; 3-[5-(3,4,5-trichlor-phenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-4,5,6,7-tetrahydrobenzo[c]thiophen-1 -carboxylsyre(1,1 -dioxohexahydrothiopyran-4-yl)-amid; 3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4.5.6.7- tetrahydrobenzo[c]thiophen-1 -carboxylsyre(1,1 -dioxothietan-3-yl)-amid; 3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4.5.6.7- tetrahydrobenzo[c]thiophen-1 -carboxylsyre(1,1 -dioxohexahydro-thiopyran-4-yl)-amid; eller et salt deraf.
10. Formulering omfattende en forbindelse, eller salt deraf, ifølge et hvilket som helst af kravene 1 til 9 og én eller flere acceptable bærere.
11. Forbindelse, eller salt deraf, ifølge et hvilket som helst af kravene 1 til 9 til anvendelse ved bekæmpelse af et parasitangreb i eller på et dyr.
12. Forbindelse, eller salt deraf, til anvendelse ifølge krav 11, hvor dyret er en hund eller en kat, og parasitten er en skovflåt.
13. Forbindelse, eller et salt deraf, med formel II
hvor n er 0 eller 1; R1 er thienyl eller phenyl, hvor thienyl eller phenyl er substitueret med 2 eller 3 ens eller forskellige halogenatomer; og R11 er hydroxy, -0-(CrC4alkyl) eller et halogenatom.
14. Forbindelse ifølge krav 13, som er 3-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxylsyremethylester; 3-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-5,6-dihydro- 4H-cyclopenta[c]thiophen-1-carboxylsyremethylester; 3-[5-(3,4,5-trichlorthiophen-2-yl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4.5.6.7- tetrahydrobenzo[c]thiophen-1-carboxylsyremethylester; 3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4.5.6.7- tetrahydrobenzo[c]thiophen-1-carboxylsyremethylester; 3-[5-(3,4,5-trichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxylsyremethylester; 3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxylsyremethylester; 3-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxylsyre; 3-[5-(3,5-dichlorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxylsyre; 3-[5-(3,4,5-trichlorthiophen-2-yl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4.5.6.7- tetrahydrobenzo[c]thiophen-1-carboxylsyre; 3-[5-(3,4,5-trichlor-phenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-4,5,6,7-tetrahydrobenzo[c]thiophen-1-carboxylsyre; 3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4.5.6.7- tetrahydrobenzo[c]thiophen-1-carboxylsyre; 3-[5-(3,5-dichlor-4-fluorphenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxylsyre; 3-[5-(3,4,5-trichlor-phenyl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophen-1-carboxylsyre; 3-(5-(3,5-dichlorphenyl)-5-(trifluormethyl)-4,5-dihydroisoxazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-1 -carbonylchlorid; eller 3-[5-(3,4,5-trichlorthiophen-2-yl)-5-trifluormethyl-4,5-dihydroisoxazol-3-yl]- 4,5,6,7-tetrahydrobenzo[c]thiophen-1-carbonylchlorid.
15. Fremgangsmåde til fremstilling af en forbindelse ifølge krav 1, omfattende omsætning af en forbindelse ifølge krav 13 eller 14 med en forbindelse med formlen
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