ME02113B - Parazitocidni spojevi dihidroizoksazola - Google Patents
Parazitocidni spojevi dihidroizoksazolaInfo
- 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
- Authority
- ME
- Montenegro
- Prior art keywords
- trifluoromethyl
- dihydroisoxazol
- thiophene
- carboxamide
- tetrahydrobenzo
- Prior art date
Links
- 125000005048 dihydroisoxazolyl group Chemical class O1N(CC=C1)* 0.000 title 1
- 230000000590 parasiticidal effect Effects 0.000 title 1
- -1 and when Y 1 Chemical compound 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 150000004702 methyl esters Chemical class 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 2
- SLZMSQVOFUEICR-QFIPXVFZSA-N 1-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(prop-2-ynylamino)ethyl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1[C@@]1(C(F)(F)F)ON=C(C2=C3CCCC3=C(C(=O)NCC(=O)NCC#C)S2)C1 SLZMSQVOFUEICR-QFIPXVFZSA-N 0.000 claims 2
- HZJBQXYHZGHGGF-UHFFFAOYSA-N 1-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxylic acid Chemical compound C=12CCCC2=C(C(=O)O)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=C(Cl)C(Cl)=C1 HZJBQXYHZGHGGF-UHFFFAOYSA-N 0.000 claims 2
- SLZMSQVOFUEICR-UHFFFAOYSA-N 1-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(prop-2-ynylamino)ethyl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCC3=C(C(=O)NCC(=O)NCC#C)S2)C1 SLZMSQVOFUEICR-UHFFFAOYSA-N 0.000 claims 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical class CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 2
- GGLMRTBEBZPTGR-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxylic acid Chemical group C=12CCCCC2=C(C(=O)O)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 GGLMRTBEBZPTGR-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 244000045947 parasite Species 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- HJPGBPJVQPGICE-KRWDZBQOSA-N 1-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxylic acid Chemical compound C1([C@]2(ON=C(C2)C=2SC(=C3CCCC3=2)C(=O)O)C(F)(F)F)=CC(Cl)=C(F)C(Cl)=C1 HJPGBPJVQPGICE-KRWDZBQOSA-N 0.000 claims 1
- PJHIHQODKKPBPS-FQEVSTJZSA-N 1-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1[C@@]1(C(F)(F)F)ON=C(C2=C3CCCC3=C(C(=O)NCC(=O)NCC(F)(F)F)S2)C1 PJHIHQODKKPBPS-FQEVSTJZSA-N 0.000 claims 1
- MWYREYADDKOMLM-CKAQCJTGSA-N 1-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[(3r)-2-oxopyrrolidin-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCC3=C(C(=O)N[C@H]3C(NCC3)=O)S2)C1 MWYREYADDKOMLM-CKAQCJTGSA-N 0.000 claims 1
- PPDOMIXKNZWIIT-UHFFFAOYSA-N 1-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCC3=C(C(=O)NC3C(N(CC(F)(F)F)CC3)=O)S2)C1 PPDOMIXKNZWIIT-UHFFFAOYSA-N 0.000 claims 1
- PJHIHQODKKPBPS-UHFFFAOYSA-N 1-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCC3=C(C(=O)NCC(=O)NCC(F)(F)F)S2)C1 PJHIHQODKKPBPS-UHFFFAOYSA-N 0.000 claims 1
- WHQXFVXOWIPFFB-UHFFFAOYSA-N 1-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxylic acid Chemical compound C=12CCCC2=C(C(=O)O)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 WHQXFVXOWIPFFB-UHFFFAOYSA-N 0.000 claims 1
- VESPVCODAVJBQB-UHFFFAOYSA-N 1-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(4-oxocyclohexyl)-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(=C1CCCC1=1)SC=1C(=O)NC1CCC(=O)CC1 VESPVCODAVJBQB-UHFFFAOYSA-N 0.000 claims 1
- ZUUODQVLNKYEML-RBFZIWAESA-N 1-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[(3r)-2-oxopyrrolidin-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(=C1CCCC1=1)SC=1C(=O)N[C@@H]1CCNC1=O ZUUODQVLNKYEML-RBFZIWAESA-N 0.000 claims 1
- KJGPRENHKZBBHW-UHFFFAOYSA-N 1-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound O=C1N(CC(F)(F)F)CCC1NC(=O)C1=C2CCCC2=C(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)S1 KJGPRENHKZBBHW-UHFFFAOYSA-N 0.000 claims 1
- CVUNGLQSTURYRZ-UHFFFAOYSA-N 1-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C=12CCCC2=C(C(=O)NCC(=O)NCC(F)(F)F)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 CVUNGLQSTURYRZ-UHFFFAOYSA-N 0.000 claims 1
- OKOJOYAIAURYQL-RBFZIWAESA-N 2-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[(3r)-2-oxopyrrolidin-3-yl]thieno[2,3-b]pyridine-5-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(SC1=NC=2)=CC1=CC=2C(=O)N[C@@H]1CCNC1=O OKOJOYAIAURYQL-RBFZIWAESA-N 0.000 claims 1
- RRNWQOUONHHENL-UHFFFAOYSA-N 2-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]thieno[2,3-b]pyridine-5-carboxamide Chemical compound C=1C2=CC(C(=O)NCC(=O)NCC(F)(F)F)=CN=C2SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 RRNWQOUONHHENL-UHFFFAOYSA-N 0.000 claims 1
- HJAFQUZZCJKRMK-UHFFFAOYSA-N 2-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]thieno[2,3-b]pyridine-5-carboxylic acid Chemical compound C=1C2=CC(C(=O)O)=CN=C2SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 HJAFQUZZCJKRMK-UHFFFAOYSA-N 0.000 claims 1
- KCEIKSLIMOHDGN-UHFFFAOYSA-N 2-amino-n-(2,2-difluoroethyl)acetamide Chemical compound NCC(=O)NCC(F)F KCEIKSLIMOHDGN-UHFFFAOYSA-N 0.000 claims 1
- GPLVBCFWVKURSF-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1C(C=2SC3=CC=CC=C3N=2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 GPLVBCFWVKURSF-UHFFFAOYSA-N 0.000 claims 1
- FTQFMTCCEGMLEQ-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1C(C=2SC3=CC=CC=C3C=2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 FTQFMTCCEGMLEQ-UHFFFAOYSA-N 0.000 claims 1
- OLYJYPPMGNIUCU-UHFFFAOYSA-N 3-(4-chloro-1-benzothiophen-2-yl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1C(C=2SC3=CC=CC(Cl)=C3C=2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 OLYJYPPMGNIUCU-UHFFFAOYSA-N 0.000 claims 1
- XFPACRHTPZLNHU-UHFFFAOYSA-N 3-(5-bromothieno[2,3-b]pyridin-2-yl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1C(C=2SC3=NC=C(Br)C=C3C=2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 XFPACRHTPZLNHU-UHFFFAOYSA-N 0.000 claims 1
- RNUSHLOUYBDWAQ-UHFFFAOYSA-N 3-(5-chloro-1-benzothiophen-2-yl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1C(C=2SC3=CC=C(Cl)C=C3C=2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 RNUSHLOUYBDWAQ-UHFFFAOYSA-N 0.000 claims 1
- QULQJDKVKHOHJD-OPAMFIHVSA-N 3-[(5r)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[(3r)-2-oxopyrrolidin-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C([C@](ON=1)(C(F)(F)F)C=2C=C(Cl)C=C(Cl)C=2)C=1C(=C1CCCCC1=1)SC=1C(=O)N[C@@H]1CCNC1=O QULQJDKVKHOHJD-OPAMFIHVSA-N 0.000 claims 1
- QULQJDKVKHOHJD-ZHRRBRCNSA-N 3-[(5s)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[(3r)-2-oxopyrrolidin-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C([C@@](ON=1)(C(F)(F)F)C=2C=C(Cl)C=C(Cl)C=2)C=1C(=C1CCCCC1=1)SC=1C(=O)N[C@@H]1CCNC1=O QULQJDKVKHOHJD-ZHRRBRCNSA-N 0.000 claims 1
- MUNSNCRYSLXQPK-UHFFFAOYSA-N 3-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxylic acid Chemical compound C=12CCCCC2=C(C(=O)O)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=C(Cl)C(Cl)=C1 MUNSNCRYSLXQPK-UHFFFAOYSA-N 0.000 claims 1
- BVBQWCDBGRKPJF-UHFFFAOYSA-N 3-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(4-oxocyclohexyl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCCC3=C(C(=O)NC3CCC(=O)CC3)S2)C1 BVBQWCDBGRKPJF-UHFFFAOYSA-N 0.000 claims 1
- JVCACHRWWDYLNO-UHFFFAOYSA-N 3-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(oxan-4-yl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCCC3=C(C(=O)NC3CCOCC3)S2)C1 JVCACHRWWDYLNO-UHFFFAOYSA-N 0.000 claims 1
- LIRNCGIFSXTLNS-JGHKVMFLSA-N 3-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[(3r)-2-oxopyrrolidin-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCCC3=C(C(=O)N[C@H]3C(NCC3)=O)S2)C1 LIRNCGIFSXTLNS-JGHKVMFLSA-N 0.000 claims 1
- CGDXLDIXJUJKPD-UHFFFAOYSA-N 3-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCCC3=C(C(=O)NC3C(N(CC(F)(F)F)CC3)=O)S2)C1 CGDXLDIXJUJKPD-UHFFFAOYSA-N 0.000 claims 1
- RMSHEXPNFWOMQL-UHFFFAOYSA-N 3-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCCC3=C(C(=O)NCC(=O)NCC(F)(F)F)S2)C1 RMSHEXPNFWOMQL-UHFFFAOYSA-N 0.000 claims 1
- BGXYHUIBLZIGNW-UHFFFAOYSA-N 3-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(prop-2-ynylamino)ethyl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCCC3=C(C(=O)NCC(=O)NCC#C)S2)C1 BGXYHUIBLZIGNW-UHFFFAOYSA-N 0.000 claims 1
- QRBOCJBFPBGMTG-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carbonyl chloride Chemical compound C1C(C2=C3CCCCC3=C(C(Cl)=O)S2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 QRBOCJBFPBGMTG-UHFFFAOYSA-N 0.000 claims 1
- HGQQIQQALFHKLB-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(2-methylsulfanylethyl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C=12CCCCC2=C(C(=O)NCCSC)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 HGQQIQQALFHKLB-UHFFFAOYSA-N 0.000 claims 1
- OOOGFLOCGITQLD-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(3,3,3-trifluoropropyl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C=12CCCCC2=C(C(=O)NCCC(F)(F)F)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 OOOGFLOCGITQLD-UHFFFAOYSA-N 0.000 claims 1
- PODYTNIYLSMCHA-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(3-hydroxycyclohexyl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1C(O)CCCC1NC(=O)C1=C2CCCCC2=C(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)S1 PODYTNIYLSMCHA-UHFFFAOYSA-N 0.000 claims 1
- IZDXHCLBWUMHGI-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(3-oxocyclohexyl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(=C1CCCCC1=1)SC=1C(=O)NC1CCCC(=O)C1 IZDXHCLBWUMHGI-UHFFFAOYSA-N 0.000 claims 1
- JCJIBATXKQRVQC-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(5-fluoropyridin-2-yl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N1=CC(F)=CC=C1NC(=O)C1=C2CCCCC2=C(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)S1 JCJIBATXKQRVQC-UHFFFAOYSA-N 0.000 claims 1
- GTGMFQWEOXQSOQ-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(oxan-3-yl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(=C1CCCCC1=1)SC=1C(=O)NC1CCCOC1 GTGMFQWEOXQSOQ-UHFFFAOYSA-N 0.000 claims 1
- GDAHTZSDEVHFNP-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(oxan-4-yl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(=C1CCCCC1=1)SC=1C(=O)NC1CCOCC1 GDAHTZSDEVHFNP-UHFFFAOYSA-N 0.000 claims 1
- HKESCRXWYYIPLH-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-(oxolan-2-ylmethyl)-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(=C1CCCCC1=1)SC=1C(=O)NCC1CCCO1 HKESCRXWYYIPLH-UHFFFAOYSA-N 0.000 claims 1
- MQSPPPDPPYLNEK-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-(ethylamino)-2-oxoethyl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C=12CCCCC2=C(C(=O)NCC(=O)NCC)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 MQSPPPDPPYLNEK-UHFFFAOYSA-N 0.000 claims 1
- YWBUCTXHGPHAGI-UHFFFAOYSA-N 3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-n-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C=12CCCCC2=C(C(=O)NCC(=O)NCC(F)(F)F)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 YWBUCTXHGPHAGI-UHFFFAOYSA-N 0.000 claims 1
- PABCADDJSLBEHV-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-3-(3-methyl-1-benzothiophen-2-yl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound S1C2=CC=CC=C2C(C)=C1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 PABCADDJSLBEHV-UHFFFAOYSA-N 0.000 claims 1
- PQELBAMFDYPKGV-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-3-(5-methyl-1-benzothiophen-2-yl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C=1C2=CC(C)=CC=C2SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 PQELBAMFDYPKGV-UHFFFAOYSA-N 0.000 claims 1
- GXRFDLCFDPNGCV-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-3-thieno[2,3-b]pyridin-2-yl-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1C(C=2SC3=NC=CC=C3C=2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 GXRFDLCFDPNGCV-UHFFFAOYSA-N 0.000 claims 1
- TZHJQCQMJDWWHU-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-3-thieno[2,3-c]pyridin-2-yl-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1C(C=2SC3=CN=CC=C3C=2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 TZHJQCQMJDWWHU-UHFFFAOYSA-N 0.000 claims 1
- 241000282326 Felis catus Species 0.000 claims 1
- 206010061217 Infestation Diseases 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- JKWIZJFMGHWYOY-UHFFFAOYSA-N methyl 1-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxylate Chemical compound C=12CCCC2=C(C(=O)OC)SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 JKWIZJFMGHWYOY-UHFFFAOYSA-N 0.000 claims 1
- IATOYJYKQCVDJJ-UHFFFAOYSA-N methyl 2-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]thieno[2,3-b]pyridine-5-carboxylate Chemical compound C=1C2=CC(C(=O)OC)=CN=C2SC=1C(C1)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 IATOYJYKQCVDJJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- MRFPGIPRGXSRCQ-UHFFFAOYSA-N n,n-dimethyl-2-[4-[3-[5-(3,4,5-trichlorothiophen-2-yl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carbonyl]piperazin-1-yl]acetamide Chemical compound C1CN(CC(=O)N(C)C)CCN1C(=O)C1=C2CCCCC2=C(C=2CC(ON=2)(C2=C(C(Cl)=C(Cl)S2)Cl)C(F)(F)F)S1 MRFPGIPRGXSRCQ-UHFFFAOYSA-N 0.000 claims 1
- DSMJFQAQKGVAGO-UHFFFAOYSA-N n-(1-cyclopropyl-2-oxopyrrolidin-3-yl)-3-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)CC=1C(=C1CCCCC1=1)SC=1C(=O)NC(C1=O)CCN1C1CC1 DSMJFQAQKGVAGO-UHFFFAOYSA-N 0.000 claims 1
- JWGRKLOPDOWYQV-UHFFFAOYSA-N n-(1-cyclopropyl-2-oxopyrrolidin-3-yl)-3-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCCC3=C(C(=O)NC3C(N(C4CC4)CC3)=O)S2)C1 JWGRKLOPDOWYQV-UHFFFAOYSA-N 0.000 claims 1
- VRVDVHPNTMYBAY-UHFFFAOYSA-N n-(1-cyclopropyl-2-oxopyrrolidin-3-yl)-3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C=C(Cl)C=2)CC=1C(=C1CCCCC1=1)SC=1C(=O)NC(C1=O)CCN1C1CC1 VRVDVHPNTMYBAY-UHFFFAOYSA-N 0.000 claims 1
- UXWGHEGEIQJAAB-UHFFFAOYSA-N n-(4-carbamoylphenyl)-3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1NC(=O)C1=C2CCCCC2=C(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)S1 UXWGHEGEIQJAAB-UHFFFAOYSA-N 0.000 claims 1
- HJDYULYHZFGFLI-UHFFFAOYSA-N n-(oxan-4-yl)-3-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)CC=1C(=C1CCCCC1=1)SC=1C(=O)NC1CCOCC1 HJDYULYHZFGFLI-UHFFFAOYSA-N 0.000 claims 1
- WZGLUGOCAASPMS-CKAQCJTGSA-N n-[(3r)-2-oxopyrrolidin-3-yl]-1-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)CC=1C(=C1CCCC1=1)SC=1C(=O)N[C@@H]1CCNC1=O WZGLUGOCAASPMS-CKAQCJTGSA-N 0.000 claims 1
- LJDOEOMGYYTKNO-JGHKVMFLSA-N n-[(3r)-2-oxopyrrolidin-3-yl]-3-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound N=1OC(C(F)(F)F)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)CC=1C(=C1CCCCC1=1)SC=1C(=O)N[C@@H]1CCNC1=O LJDOEOMGYYTKNO-JGHKVMFLSA-N 0.000 claims 1
- SXSHRCUTDJAYDC-UHFFFAOYSA-N n-[2-(cyanomethylamino)-2-oxoethyl]-1-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCC3=C(C(=O)NCC(=O)NCC#N)S2)C1 SXSHRCUTDJAYDC-UHFFFAOYSA-N 0.000 claims 1
- ADAGBWQSRGHHTC-UHFFFAOYSA-N n-[2-(cyanomethylamino)-2-oxoethyl]-1-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1C(C2=C3CCCC3=C(C(=O)NCC(=O)NCC#N)S2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 ADAGBWQSRGHHTC-UHFFFAOYSA-N 0.000 claims 1
- BSLWRULHVPAJNC-UHFFFAOYSA-N n-[2-(cyanomethylamino)-2-oxoethyl]-3-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1C(C2=C3CCCCC3=C(C(=O)NCC(=O)NCC#N)S2)=NOC1(C(F)(F)F)C1=CC(Cl)=C(Cl)C(Cl)=C1 BSLWRULHVPAJNC-UHFFFAOYSA-N 0.000 claims 1
- AZXFVENIJCTPHR-UHFFFAOYSA-N n-[2-(cyanomethylamino)-2-oxoethyl]-3-[5-(3,4,5-trichlorothiophen-2-yl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1C(C2=C3CCCCC3=C(C(=O)NCC(=O)NCC#N)S2)=NOC1(C(F)(F)F)C=1SC(Cl)=C(Cl)C=1Cl AZXFVENIJCTPHR-UHFFFAOYSA-N 0.000 claims 1
- BUSDAXXFLOZSSM-UHFFFAOYSA-N n-[2-(cyanomethylamino)-2-oxoethyl]-3-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1C1(C(F)(F)F)ON=C(C2=C3CCCCC3=C(C(=O)NCC(=O)NCC#N)S2)C1 BUSDAXXFLOZSSM-UHFFFAOYSA-N 0.000 claims 1
- PTZPVYJNRZRNDY-UHFFFAOYSA-N n-[2-(cyanomethylamino)-2-oxoethyl]-3-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1C(C2=C3CCCCC3=C(C(=O)NCC(=O)NCC#N)S2)=NOC1(C(F)(F)F)C1=CC(Cl)=CC(Cl)=C1 PTZPVYJNRZRNDY-UHFFFAOYSA-N 0.000 claims 1
- CDCJIWZDZOGMLK-UHFFFAOYSA-N n-[2-oxo-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]-1-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound O=C1N(CC(F)(F)F)CCC1NC(=O)C1=C2CCCC2=C(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)S1 CDCJIWZDZOGMLK-UHFFFAOYSA-N 0.000 claims 1
- HMWABQPKBTZHRF-UHFFFAOYSA-N n-[2-oxo-1-(2,2,2-trifluoroethyl)pyrrolidin-3-yl]-3-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound O=C1N(CC(F)(F)F)CCC1NC(=O)C1=C2CCCCC2=C(C=2CC(ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)S1 HMWABQPKBTZHRF-UHFFFAOYSA-N 0.000 claims 1
- XQHSMNLIVNMEEO-UHFFFAOYSA-N n-[2-oxo-2-(prop-2-ynylamino)ethyl]-1-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-5,6-dihydro-4h-cyclopenta[c]thiophene-3-carboxamide Chemical compound C1C(C2=C3CCCC3=C(C(=O)NCC(=O)NCC#C)S2)=NOC1(C(F)(F)F)C1=CC(Cl)=C(Cl)C(Cl)=C1 XQHSMNLIVNMEEO-UHFFFAOYSA-N 0.000 claims 1
- XIUSHUHHQSBJPQ-UHFFFAOYSA-N n-[2-oxo-2-(prop-2-ynylamino)ethyl]-3-[5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1C(C2=C3CCCCC3=C(C(=O)NCC(=O)NCC#C)S2)=NOC1(C(F)(F)F)C1=CC(Cl)=C(Cl)C(Cl)=C1 XIUSHUHHQSBJPQ-UHFFFAOYSA-N 0.000 claims 1
- CUAGPYFKZPPYQW-UHFFFAOYSA-N n-[2-oxo-2-(prop-2-ynylamino)ethyl]-3-[5-(3,4,5-trichlorothiophen-2-yl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]-4,5,6,7-tetrahydro-2-benzothiophene-1-carboxamide Chemical compound C1C(C2=C3CCCCC3=C(C(=O)NCC(=O)NCC#C)S2)=NOC1(C(F)(F)F)C=1SC(Cl)=C(Cl)C=1Cl CUAGPYFKZPPYQW-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Classifications
-
- 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
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- 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
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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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| PCT/CN2012/072878 WO2012155676A1 (en) | 2011-05-19 | 2012-03-23 | Parasiticidal compounds, methods, and formulations |
| EP20120721146 EP2710000B1 (en) | 2011-05-19 | 2012-05-08 | Parasiticidal dihydroisoxazole compounds |
| PCT/US2012/036883 WO2012158396A1 (en) | 2011-05-19 | 2012-05-08 | Parasiticidal dihydroisoxazole compounds |
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| WO2018166855A1 (en) * | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
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| AU2019369659A1 (en) * | 2018-10-29 | 2021-04-29 | Basf Se | Process for preparation of optically enriched aldol compounds |
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| CN117320554A (zh) * | 2021-03-11 | 2023-12-29 | 碗中动物健康公司 | 用于控制犬科动物中蜱侵袭的口服犬科动物饲料和方法 |
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| CN117412673A (zh) * | 2021-03-11 | 2024-01-16 | 碗中动物健康公司 | 犬科动物口服饲料和在犬科动物中控制蚤侵袭的方法 |
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| CN114085159B (zh) * | 2021-11-25 | 2023-04-07 | 浙江大学 | 一种1,3-环己二酮还原胺化制备3-氨基环己酮的方法 |
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| WO2012155352A1 (en) | 2011-05-19 | 2012-11-22 | Eli Lilly And Company | Dihydroisoxazole compounds, parasiticidal uses and formulations thereof |
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