HRP20150588T1 - Parazitocidni spojevi dihidroizoksazola - Google Patents

Parazitocidni spojevi dihidroizoksazola Download PDF

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HRP20150588T1
HRP20150588T1 HRP20150588TT HRP20150588T HRP20150588T1 HR P20150588 T1 HRP20150588 T1 HR P20150588T1 HR P20150588T T HRP20150588T T HR P20150588TT HR P20150588 T HRP20150588 T HR P20150588T HR P20150588 T1 HRP20150588 T1 HR P20150588T1
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Croatia
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trifluoromethyl
dihydroisoxazol
thiophene
carboxamide
tetrahydrobenzo
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HRP20150588TT
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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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Eli Lilly And Company
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Publication of HRP20150588T1 publication Critical patent/HRP20150588T1/hr

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    • C07D495/02Heterocyclic 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
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    • A61K31/4353Heterocyclic 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
    • A61K31/4365Heterocyclic 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
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    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439Non 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
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    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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    • C07D417/02Heterocyclic 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
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  • 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)
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Claims (15)

1. Spoj, ili njegova sol, formule I [image] , naznačen time što A je [image] ; 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 [image] ; 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 [image] , 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 [image] ; 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 [image] ; 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 [image] ; R8 je hidroksi, -O-(C1-C5 alkil) ili [image] ; R9 je C1-C5 alkil, [image] ; 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 [image] , 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 [image] [image] [image] [image] [image] [image] [image] .
4. Spoj u skladu s patentnim zahtjevom 1, ili njegova sol, naznačen time što je A [image] , te što je Y1 dušik.
5. Spoj u skladu s patentnim zahtjevom 4, ili njegova sol, naznačen time što je R7 [image] [image] [image] ili [image] .
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, [image] , 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 [image] .
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