ME02113B - Parazitocidni spojevi dihidroizoksazola - Google Patents

Parazitocidni spojevi dihidroizoksazola

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Publication number
ME02113B
ME02113B MEP-2015-73A MEP201573A ME02113B ME 02113 B ME02113 B ME 02113B ME P201573 A MEP201573 A ME P201573A ME 02113 B ME02113 B ME 02113B
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ME
Montenegro
Prior art keywords
trifluoromethyl
dihydroisoxazol
thiophene
carboxamide
tetrahydrobenzo
Prior art date
Application number
MEP-2015-73A
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English (en)
Inventor
Zengyun An
Yang Zhang
Liang Chen
Shuhui Chen
Jean Marie Defauw
Scott Dale Holmstrom
Ping Hu
Chongzhi Tang
William Hunter White
Wentao Wu
Original Assignee
Lilly Co Eli
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Publication date
Application filed by Lilly Co Eli filed Critical Lilly Co Eli
Publication of ME02113B publication Critical patent/ME02113B/me

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—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
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/428—Thiazoles condensed with carbocyclic rings
    • 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
    • A61K31/4353—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
    • 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
    • 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
    • A61K31/495—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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—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
    • C07D417/02—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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • General Chemical & Material Sciences (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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Claims (15)

1.Spoj, ili njegova sol, formule I , naznačen time što A je ; n je 0 ili 1; R1 je tienil ili fenil, gdje je navedeni tienil ili fenil supstituiran s 2 ili 3 ista ili različita atoma halogena; R2 je svaki put neovisno vodik, C1-C5 alkil, C3-C6 cikloalkil ili C1-C5 haloagenlkil; R3 je ; p je svaki put neovisno 0 ili 1; R4 je C1-C5 alkil, C1-C5 haloagenlkil, C1-C5 cijanoalkil, C1-C5 alkiltio, C3-C6 cikloalkil, izborno supstituiran s hidroksi, halogenom ili C1-C5 alkilom; C3-C5 cikloheteroalkil, izborno supstituiran s C1-C5 alkilom, C3-C6 cikloalkilom ili C1-C5 haloagenlkilom; fenil, tienil, piridinil ili , gdje jedan od ugljika u navedenim cikloalkilima, neovisno, ili u cikloheteroalkilu, može tvoriti karbonilnu skupinu, te gdje je navedeni fenil, tienil ili piridinil izborno supstituiran s halogenom ili karbamoilnom skupinom; R5 je hidroksi, -O-(C1-C5 alkil) ili ; R6 je vodik, C1-C5 alkil, C1-C5 haloagenlkil, C1-C5 cijanoalkil, C1-C5 alkiltio ili C2-C5 alkinil; ili se R2 i R3 kombinira kako bi, s dušikom na kojeg su vezani, tvorili ; Y1, Y2 i Y3 su ugljik ili dušik, gdje je najviše samo jedan od Y1, Y2 i Y3 dušik, a kada je Y1, Y2 ili Y3 je ugljik, svaki od njih može biti supstituiran s C1-C5 alkilom; R7 je vodik, halogen, C1-C5 alkil ili ; R8 je hidroksi, -O-(C1-C5 alkil) ili ; R9 je C1-C5 alkil, ; i R10 je vodik, C1-C5 alkil, C1-C5 haloagenlkil, C1-C5 cijanoalkil, C1-C5 alkiltio ili C2-C5 alkinil.
2.Spoj u skladu s patentnim zahtjevom 1, ili njegova sol, naznačen time što je A , te što je R2 vodik, a n je 1.
3.Spoj u skladu s patentnim zahtjevom 1 ili patentni zahtjev 2, ili njegova sol, naznačen time što je R3 .
4.Spoj u skladu s patentnim zahtjevom 1, ili njegova sol, naznačen time što je A , te što je Y1 dušik.
5.Spoj u skladu s patentnim zahtjevom 4, ili njegova sol, naznačen time što je R7 ili .
6.Spoj u skladu s patentnim zahtjevom 1, ili njegova sol, naznačen time što je 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-((R)-2-oksopirolidin-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N,N-dimetil-2-(4-{3-[5-(3,4,5-triklortiofen-2-il)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karbonil}piperazin-1-il)acetamid; metilni ester ({3-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karbonil}amino)octene kiseline; metilni ester ({3-[5-(3,4,5-triklortiofen-2-il)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karbonil}amino)octene kiseline; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(2,2,2-trifluoretilamino)etil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(3-oksocikloheksil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; [2-okso-1-(2,2,2-trifluoretil)pirolidin-3-il]amid 3-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-((R)-2-oksopirolidin-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; N-(2-(cijanometilamino)-2-oksoetil)-3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(prop-2-inilamino)etil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; N-(2-okso-2-(2,2,2-trifluoretilamino)etil)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-((R)-2-oksopirolidin-3-il)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(2-(cijanometilamino)-2-oksoetil)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(2-okso-2-(prop-2-inilamino)etil)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(2,2,2-trifluoretilamino)etil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-((R)-2-oksopirolidin-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(2-(cijanometilamino)-2-oksoetil)-3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(prop-2-inilamino)etil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(2-okso-2-(2,2,2-trifluoretilamino)etil)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; N-((R)-2-oksopirolidin-3-il)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; N-(2-(cijanometilamino)-2-oksoetil)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; N-(2-okso-2-(prop-2-inilamino)etil)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; N-(2-okso-1-(2,2,2-trifluoretil)pirolidin-3-il)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(2,2,2-trifluoretilamino)etil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-((R)-2-oksopirolidin-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; N-(2-(cijanometilamino)-2-oksoetil)-3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-1-(2,2,2-trifluoretil)pirolidin-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(prop-2-inilamino)etil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(2,2,2-trifluoretilamino)etil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-(etilamino)-2-oksoetil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-((tetrahidrofuran-2-il)metil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-(metiltio)etil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(3,3,3-trifluorpropil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(3-hidroksicikloheksil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(5-fluorpiridin-2-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(tetrahidro-2H-piran-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(tietan-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(tetrahidro-2H-piran-4-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(1-ciklopropil-2-oksopirolidin-3-il)-3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(2-okso-2-(prop-2-inilamino)etil)-3-(5-(3,4,5-triklortiofen-2-il)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(2-okso-1-(2,2,2-trifluoretil)pirolidin-3-il)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(tetrahidro-2H-piran-4-il)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(1-ciklopropil-2-oksopirolidin-3-il)-3-(5-(3,4,5-triklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(4-oksocikloheksil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-1-(2,2,2-trifluoretil)pirolidin-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(tetrahidro-2H-piran-4-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(1-ciklopropil-2-oksopirolidin-3-il)-3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(4-oksocikloheksil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-1-(2,2,2-trifluoretil)pirolidin-3-il)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-((R)-5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-((R)-2-oksopirolidin-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-((S)-5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-((R)-2-oksopirolidin-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(4-karbamoilfenil)-3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; (3-karbamoiltiofen-2-il)amid 3-[5-(3,4,5-triklortiofen-2-il)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; 2-(3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamido)octena kiselina; ({3-[5-(3,4,5-triklortiofen-2-il)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karbonil}amino)octena kiselina; N-(2-(cijanometilamino)-2-oksoetil)-3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(prop-2-inilamino)etil)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; N-(2-(cijanometilamino)-2-oksoetil)-3-(5-(3,4,5-triklortiofen-2-il)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksamid; (S)-3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(2,2,2-trifluoretilamino)etil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; [(2,2-difluoretilkarbamoil)metil]amid 3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilne kiseline; [(2-fluoretilkarbamoil)metil]amid 3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilne kiseline; [(2-fluoretilkarbamoil)metil]amid (S)-3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilne kiseline; 3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(prop-2-inilamino)etil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; (S)-3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(prop-2-inilamino)etil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid; 3-(4-klorbenzo[b]tiofen-2-il)-5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol; 2-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]tieno[2,3-c]piridin; 5-brom-2-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]tieno[2,3-b]piridin; 2-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]tieno[2,3-b]piridin; 3-(benzo[b]tiofen-2-il)-5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol; 3-(benzo[d]thiazol-2-il)-5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol; 5-(3,5-diklorfenil)-3-(3-metilbenzo[b]tiofen-2-il)-5-(trifluormetil)-4,5-dihidroizoksazol; 5-(3,5-diklorfenil)-3-(5-metilbenzo[b]tiofen-2-il)-5-(trifluormetil)-4,5-dihidroizoksazol; 3-(5-klorbenzo[b]tiofen-2-il)-5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol; metil-2-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)tieno[2,3-b]piridin-5-karboksilat; 2-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]tieno[2,3-b]piridin-5-karboksilna kiselina; 2-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(2,2,2-trifluoretilamino)etil)tieno[2,3-b]piridin-5-karboksamid; ili 2-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-((R)-2-oksopirolidin-3-il)tieno[2,3-b]piridin-5-karboksamid.
7.Spoj u skladu s patentnim zahtjevom 1, ili njegova sol, naznačen time što je [(2,2-difluoretilkarbamoil)metil]amid) (S)-3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilne kiseline.
8.Spoj u skladu s patentnim zahtjevom 1, ili njegova sol, naznačen time što je (S)-3-(5-(3,5-diklor-4-fluorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-N-(2-okso-2-(prop-2-inilamino)etil)-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksamid.
9.Spoj, naznačen time što je (1,1-dioksotietan-3-il)amid 3-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; (1,1-dioksoheksahidro-116-tiopiran-4-il)amid 3-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; (1,1-dioksoheksahidrotiopiran-4-il)amid 3-[5-(3,4,5-triklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; (1,1-dioksotietan-3-il)amid 3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; (1,1-dioksoheksahidrotiopiran-4-il)amid 3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; ili njihove soli.
10.Formulacija, naznačena time što sadrži spoj, ili njegovu sol, u skladu s bilo kojim od patentnih zahtjeva 1 do 9, kao i jednu ili više prihvatljivih podloga.
11.Spoj, ili njegova sol, u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što je namijenjen upotrebi u kontroli infestacije parazitima u ili na životinji.
12.Spoj, ili njegova sol, namijenjen upotrebi u skladu s patentnim zahtjevom 11, naznačen time što je navedena životinja pas ili mačka, a navedeni parazit je krpelj.
13.Spoj Formule II, ili njegova sol, , naznačen time što n je 0 ili 1; R1 je tienil ili fenil, gdje je navedeni tienil ili fenil supstituiran s 2 ili 3 ista ili različita atoma halogena; i R11 je hidroksi, -O-(C1-C4 alkil) ili atom halogena.
14.Spoj u skladu s patentnim zahtjevom 13, naznačen time što je metilni ester 3-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; metilni ester 3-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilne kiseline; metilni ester 3-[5-(3,4,5-triklortiofen-2-il)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; metilni ester 3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilne kiseline; metilni ester 3-[5-(3,4,5-triklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilne kiseline; metilni ester 3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilne kiseline; 3-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilna kiselina; 3-[5-(3,5-diklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilna kiselina; 3-[5-(3,4,5-triklortiofen-2-il)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilna kiselina; 3-[5-(3,4,5-triklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilna kiselina; 3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karboksilna kiselina; 3-[5-(3,5-diklor-4-fluorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilna kiselina; 3-[5-(3,4,5-triklorfenil)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-5,6-dihidro-4H-ciklopenta[c]tiofen-1-karboksilna kiselina; 3-(5-(3,5-diklorfenil)-5-(trifluormetil)-4,5-dihidroizoksazol-3-il)-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karbonil-klorid; ili 3-[5-(3,4,5-triklortiofen-2-il)-5-trifluormetil-4,5-dihidroizoksazol-3-il]-4,5,6,7-tetrahidrobenzo[c]tiofen-1-karbonil-klorid.
15.Postupak dobivanja spoja u skladu s patentnim zahtjevom 1, naznačen time što se sastoji u reakciji spoja u skladu s patentnim zahtjevom 13 ili 14 sa spojem formule .
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