RU2014131950A - Способ получения производных хирального изоксазолин азетидина в качестве противопаразитарных агентов - Google Patents
Способ получения производных хирального изоксазолин азетидина в качестве противопаразитарных агентов Download PDFInfo
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- RU2014131950A RU2014131950A RU2014131950A RU2014131950A RU2014131950A RU 2014131950 A RU2014131950 A RU 2014131950A RU 2014131950 A RU2014131950 A RU 2014131950A RU 2014131950 A RU2014131950 A RU 2014131950A RU 2014131950 A RU2014131950 A RU 2014131950A
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- trifluoromethyl
- carboxylate
- dichloro
- dihydroisoxazol
- Prior art date
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- 241001111258 Chirostoma jordani Species 0.000 title 1
- 239000003096 antiparasitic agent Substances 0.000 title 1
- 229940125687 antiparasitic agent Drugs 0.000 title 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical class C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 = S Chemical group 0.000 claims abstract 31
- 125000001424 substituent group Chemical group 0.000 claims abstract 16
- 125000005843 halogen group Chemical group 0.000 claims abstract 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 14
- 238000000034 method Methods 0.000 claims abstract 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- 150000001875 compounds Chemical class 0.000 claims abstract 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 28
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 10
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 235000001258 Cinchona calisaya Nutrition 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 229960000948 quinine Drugs 0.000 claims 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
- WHOVKIMCOPXUQR-UHFFFAOYSA-N 3-[4-(azetidin-3-yl)phenyl]-5-phenyl-5-(trifluoromethyl)-4h-1,2-oxazole Chemical class N=1OC(C(F)(F)F)(C=2C=CC=CC=2)CC=1C(C=C1)=CC=C1C1CNC1 WHOVKIMCOPXUQR-UHFFFAOYSA-N 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- TVGSMPZXTCQNAB-UHFFFAOYSA-N 1-[4-(azetidin-3-yl)phenyl]-4,4,4-trifluoro-3-phenylbut-2-en-1-one Chemical compound FC(F)(F)C(=CC(=O)c1ccc(cc1)C1CNC1)c1ccccc1 TVGSMPZXTCQNAB-UHFFFAOYSA-N 0.000 claims 2
- VOXJHBJSBBOWHS-UHFFFAOYSA-N 1-[4-(azetidin-3-yl)phenyl]ethanone Chemical class C1=CC(C(=O)C)=CC=C1C1CNC1 VOXJHBJSBBOWHS-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- HYRBYWSCPHNZQT-UHFFFAOYSA-N tert-butyl 3-(4-acetylphenyl)-3-fluoroazetidine-1-carboxylate Chemical compound C1=CC(C(=O)C)=CC=C1C1(F)CN(C(=O)OC(C)(C)C)C1 HYRBYWSCPHNZQT-UHFFFAOYSA-N 0.000 claims 2
- UTXXCBAQFJJBKN-HSZRJFAPSA-N tert-butyl 3-[4-[(5r)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(C=2C[C@@](ON=2)(C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)C=C1 UTXXCBAQFJJBKN-HSZRJFAPSA-N 0.000 claims 2
- RECJKSCXHMXWQY-YBEGLDIGSA-N tert-butyl 3-[4-[(z)-3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-2-enoyl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(C(=O)\C=C(\C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)C=C1 RECJKSCXHMXWQY-YBEGLDIGSA-N 0.000 claims 2
- FDCBGRUURAPIJZ-ODLFYWEKSA-N tert-butyl 3-[4-[(z)-3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-2-enoyl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(C(=O)\C=C(\C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=C1 FDCBGRUURAPIJZ-ODLFYWEKSA-N 0.000 claims 2
- UHFMZDBMCPKXQH-YBEGLDIGSA-N tert-butyl 3-fluoro-3-[4-[(z)-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-2-enoyl]phenyl]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(C(=O)\C=C(\C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)C=C1 UHFMZDBMCPKXQH-YBEGLDIGSA-N 0.000 claims 2
- 125000002053 thietanyl group Chemical group 0.000 claims 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 1
- LFHOUJHUGJHRIO-GOSISDBHSA-N (5r)-3-[4-(3-fluoroazetidin-3-yl)phenyl]-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C([C@](ON=1)(C(F)(F)F)C=2C=C(Cl)C(Cl)=C(Cl)C=2)C=1C(C=C1)=CC=C1C1(F)CNC1 LFHOUJHUGJHRIO-GOSISDBHSA-N 0.000 claims 1
- KGWBVTDKNZMVSD-GOSISDBHSA-N (5r)-5-(3,5-dichloro-4-fluorophenyl)-3-[4-(3-fluoroazetidin-3-yl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1[C@]1(C(F)(F)F)ON=C(C=2C=CC(=CC=2)C2(F)CNC2)C1 KGWBVTDKNZMVSD-GOSISDBHSA-N 0.000 claims 1
- BZFSJRDPMCGFCY-GOSISDBHSA-N (5r)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-3-[4-(3-fluoroazetidin-3-yl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound ClC1=C(Cl)C(C(F)(F)F)=CC([C@@]2(ON=C(C2)C=2C=CC(=CC=2)C2(F)CNC2)C(F)(F)F)=C1 BZFSJRDPMCGFCY-GOSISDBHSA-N 0.000 claims 1
- LFHOUJHUGJHRIO-SFHVURJKSA-N (5s)-3-[4-(3-fluoroazetidin-3-yl)phenyl]-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C([C@@](ON=1)(C(F)(F)F)C=2C=C(Cl)C(Cl)=C(Cl)C=2)C=1C(C=C1)=CC=C1C1(F)CNC1 LFHOUJHUGJHRIO-SFHVURJKSA-N 0.000 claims 1
- KGWBVTDKNZMVSD-SFHVURJKSA-N (5s)-5-(3,5-dichloro-4-fluorophenyl)-3-[4-(3-fluoroazetidin-3-yl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1[C@@]1(C(F)(F)F)ON=C(C=2C=CC(=CC=2)C2(F)CNC2)C1 KGWBVTDKNZMVSD-SFHVURJKSA-N 0.000 claims 1
- DVSSNWKOASTWTL-SFHVURJKSA-N (5s)-5-(3,5-dichlorophenyl)-3-[4-(3-fluoroazetidin-3-yl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound C([C@@](ON=1)(C(F)(F)F)C=2C=C(Cl)C=C(Cl)C=2)C=1C(C=C1)=CC=C1C1(F)CNC1 DVSSNWKOASTWTL-SFHVURJKSA-N 0.000 claims 1
- BZFSJRDPMCGFCY-SFHVURJKSA-N (5s)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-3-[4-(3-fluoroazetidin-3-yl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazole Chemical compound ClC1=C(Cl)C(C(F)(F)F)=CC([C@]2(ON=C(C2)C=2C=CC(=CC=2)C2(F)CNC2)C(F)(F)F)=C1 BZFSJRDPMCGFCY-SFHVURJKSA-N 0.000 claims 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 claims 1
- ZQQSYPZAPHRXRY-UHFFFAOYSA-N 1-hydroxyazetidine Chemical compound ON1CCC1 ZQQSYPZAPHRXRY-UHFFFAOYSA-N 0.000 claims 1
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical class FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- KHNGFFOEQHPXRG-UHFFFAOYSA-N 2-bromo-1-phenylazetidine Chemical compound BrC1CCN1C1=CC=CC=C1 KHNGFFOEQHPXRG-UHFFFAOYSA-N 0.000 claims 1
- RAXRSTOKCITCSP-UHFFFAOYSA-N 3-(4-bromophenyl)azetidin-3-ol Chemical compound C=1C=C(Br)C=CC=1C1(O)CNC1 RAXRSTOKCITCSP-UHFFFAOYSA-N 0.000 claims 1
- FXZHWYUBOHEJLD-UHFFFAOYSA-N 3-(trifluoromethyl)-4,5-dihydro-1,2-oxazole Chemical compound FC(F)(F)C1=NOCC1 FXZHWYUBOHEJLD-UHFFFAOYSA-N 0.000 claims 1
- FKLZLVYZEWVANK-GOSISDBHSA-N 3-[4-[(5r)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C=1C=C(C=2C[C@@](ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)C=CC=1C1(O)CNC1 FKLZLVYZEWVANK-GOSISDBHSA-N 0.000 claims 1
- SIBLGQFWPWHDTF-GOSISDBHSA-N 3-[4-[(5r)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C=1C=C(C=2C[C@@](ON=2)(C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)C=CC=1C1(O)CNC1 SIBLGQFWPWHDTF-GOSISDBHSA-N 0.000 claims 1
- AAIWBZNLKMUQJE-GOSISDBHSA-N 3-[4-[(5r)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C=1C=C(C=2C[C@@](ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=CC=1C1(O)CNC1 AAIWBZNLKMUQJE-GOSISDBHSA-N 0.000 claims 1
- ZMMFLQAETXYDLX-GOSISDBHSA-N 3-[4-[(5r)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C=1C=C(C=2C[C@@](ON=2)(C=2C=C(C(Cl)=C(Cl)C=2)C(F)(F)F)C(F)(F)F)C=CC=1C1(O)CNC1 ZMMFLQAETXYDLX-GOSISDBHSA-N 0.000 claims 1
- FKLZLVYZEWVANK-SFHVURJKSA-N 3-[4-[(5s)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C=1C=C(C=2C[C@](ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)C=CC=1C1(O)CNC1 FKLZLVYZEWVANK-SFHVURJKSA-N 0.000 claims 1
- SIBLGQFWPWHDTF-SFHVURJKSA-N 3-[4-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C=1C=C(C=2C[C@](ON=2)(C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)C=CC=1C1(O)CNC1 SIBLGQFWPWHDTF-SFHVURJKSA-N 0.000 claims 1
- AAIWBZNLKMUQJE-SFHVURJKSA-N 3-[4-[(5s)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C=1C=C(C=2C[C@](ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=CC=1C1(O)CNC1 AAIWBZNLKMUQJE-SFHVURJKSA-N 0.000 claims 1
- ZMMFLQAETXYDLX-SFHVURJKSA-N 3-[4-[(5s)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C=1C=C(C=2C[C@](ON=2)(C=2C=C(C(Cl)=C(Cl)C=2)C(F)(F)F)C(F)(F)F)C=CC=1C1(O)CNC1 ZMMFLQAETXYDLX-SFHVURJKSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000010640 amide synthesis reaction Methods 0.000 claims 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 1
- AKMDOVCDJPRJNC-UHFFFAOYSA-N benzyl 3-(4-acetylphenyl)-3-fluoroazetidine-1-carboxylate Chemical compound C1=CC(C(=O)C)=CC=C1C1(F)CN(C(=O)OCC=2C=CC=CC=2)C1 AKMDOVCDJPRJNC-UHFFFAOYSA-N 0.000 claims 1
- NIDOLSMKQFJIRR-UHFFFAOYSA-N benzyl 3-(4-acetylphenyl)-3-hydroxyazetidine-1-carboxylate Chemical compound C1=CC(C(=O)C)=CC=C1C1(O)CN(C(=O)OCC=2C=CC=CC=2)C1 NIDOLSMKQFJIRR-UHFFFAOYSA-N 0.000 claims 1
- USCYKMMXSIJROR-UHFFFAOYSA-N benzyl 3-(4-bromophenyl)-3-fluoroazetidine-1-carboxylate Chemical compound C1C(F)(C=2C=CC(Br)=CC=2)CN1C(=O)OCC1=CC=CC=C1 USCYKMMXSIJROR-UHFFFAOYSA-N 0.000 claims 1
- WEMCHFXJWLYOEM-UHFFFAOYSA-N benzyl 3-(4-bromophenyl)-3-hydroxyazetidine-1-carboxylate Chemical compound C1C(O)(C=2C=CC(Br)=CC=2)CN1C(=O)OCC1=CC=CC=C1 WEMCHFXJWLYOEM-UHFFFAOYSA-N 0.000 claims 1
- JWZFWWVELPRKLB-AREMUKBSSA-N benzyl 3-[4-[(5r)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1[C@]1(C(F)(F)F)ON=C(C=2C=CC(=CC=2)C2(F)CN(C2)C(=O)OCC=2C=CC=CC=2)C1 JWZFWWVELPRKLB-AREMUKBSSA-N 0.000 claims 1
- PANOLPUYBWLEPA-AREMUKBSSA-N benzyl 3-[4-[(5r)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1C(O)(C=2C=CC(=CC=2)C=2C[C@@](ON=2)(C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)CN1C(=O)OCC1=CC=CC=C1 PANOLPUYBWLEPA-AREMUKBSSA-N 0.000 claims 1
- HDEIDUNOOMZYRO-AREMUKBSSA-N benzyl 3-[4-[(5r)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C([C@](ON=1)(C(F)(F)F)C=2C=C(Cl)C=C(Cl)C=2)C=1C(C=C1)=CC=C1C(C1)(F)CN1C(=O)OCC1=CC=CC=C1 HDEIDUNOOMZYRO-AREMUKBSSA-N 0.000 claims 1
- CUVNLNIRUAREAS-AREMUKBSSA-N benzyl 3-[4-[(5r)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1C(O)(C=2C=CC(=CC=2)C=2C[C@@](ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)CN1C(=O)OCC1=CC=CC=C1 CUVNLNIRUAREAS-AREMUKBSSA-N 0.000 claims 1
- GDJPADPPKXQSEX-AREMUKBSSA-N benzyl 3-[4-[(5r)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound ClC1=C(Cl)C(C(F)(F)F)=CC([C@@]2(ON=C(C2)C=2C=CC(=CC=2)C2(F)CN(C2)C(=O)OCC=2C=CC=CC=2)C(F)(F)F)=C1 GDJPADPPKXQSEX-AREMUKBSSA-N 0.000 claims 1
- NMVOKLOLVDCLIS-AREMUKBSSA-N benzyl 3-[4-[(5r)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1C(O)(C=2C=CC(=CC=2)C=2C[C@@](ON=2)(C=2C=C(C(Cl)=C(Cl)C=2)C(F)(F)F)C(F)(F)F)CN1C(=O)OCC1=CC=CC=C1 NMVOKLOLVDCLIS-AREMUKBSSA-N 0.000 claims 1
- JWZFWWVELPRKLB-SANMLTNESA-N benzyl 3-[4-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1=C(Cl)C(F)=C(Cl)C=C1[C@@]1(C(F)(F)F)ON=C(C=2C=CC(=CC=2)C2(F)CN(C2)C(=O)OCC=2C=CC=CC=2)C1 JWZFWWVELPRKLB-SANMLTNESA-N 0.000 claims 1
- PANOLPUYBWLEPA-SANMLTNESA-N benzyl 3-[4-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1C(O)(C=2C=CC(=CC=2)C=2C[C@](ON=2)(C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)CN1C(=O)OCC1=CC=CC=C1 PANOLPUYBWLEPA-SANMLTNESA-N 0.000 claims 1
- HDEIDUNOOMZYRO-SANMLTNESA-N benzyl 3-[4-[(5s)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C([C@@](ON=1)(C(F)(F)F)C=2C=C(Cl)C=C(Cl)C=2)C=1C(C=C1)=CC=C1C(C1)(F)CN1C(=O)OCC1=CC=CC=C1 HDEIDUNOOMZYRO-SANMLTNESA-N 0.000 claims 1
- CUVNLNIRUAREAS-SANMLTNESA-N benzyl 3-[4-[(5s)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1C(O)(C=2C=CC(=CC=2)C=2C[C@](ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)CN1C(=O)OCC1=CC=CC=C1 CUVNLNIRUAREAS-SANMLTNESA-N 0.000 claims 1
- GDJPADPPKXQSEX-SANMLTNESA-N benzyl 3-[4-[(5s)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound ClC1=C(Cl)C(C(F)(F)F)=CC([C@]2(ON=C(C2)C=2C=CC(=CC=2)C2(F)CN(C2)C(=O)OCC=2C=CC=CC=2)C(F)(F)F)=C1 GDJPADPPKXQSEX-SANMLTNESA-N 0.000 claims 1
- NMVOKLOLVDCLIS-SANMLTNESA-N benzyl 3-[4-[(5s)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1C(O)(C=2C=CC(=CC=2)C=2C[C@](ON=2)(C=2C=C(C(Cl)=C(Cl)C=2)C(F)(F)F)C(F)(F)F)CN1C(=O)OCC1=CC=CC=C1 NMVOKLOLVDCLIS-SANMLTNESA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000012025 fluorinating agent Substances 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000006263 metalation reaction Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- KWPFFYKQSUQHCZ-UHFFFAOYSA-N tert-butyl 3-(4-acetylphenyl)-3-hydroxyazetidine-1-carboxylate Chemical compound C1=CC(C(=O)C)=CC=C1C1(O)CN(C(=O)OC(C)(C)C)C1 KWPFFYKQSUQHCZ-UHFFFAOYSA-N 0.000 claims 1
- WMHGJPVZKDXWNI-UHFFFAOYSA-N tert-butyl 3-(4-bromophenyl)-3-fluoroazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(Br)C=C1 WMHGJPVZKDXWNI-UHFFFAOYSA-N 0.000 claims 1
- XRLOWKAACZKDBK-UHFFFAOYSA-N tert-butyl 3-(4-bromophenyl)-3-hydroxyazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(O)C1=CC=C(Br)C=C1 XRLOWKAACZKDBK-UHFFFAOYSA-N 0.000 claims 1
- DSEMAAOAAFIAFP-HSZRJFAPSA-N tert-butyl 3-[4-[(5r)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(O)C1=CC=C(C=2C[C@@](ON=2)(C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)C=C1 DSEMAAOAAFIAFP-HSZRJFAPSA-N 0.000 claims 1
- AEXFKTSDPZFXKR-HSZRJFAPSA-N tert-butyl 3-[4-[(5r)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(C=2C[C@@](ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=C1 AEXFKTSDPZFXKR-HSZRJFAPSA-N 0.000 claims 1
- VZYFFZWXWAKARM-HSZRJFAPSA-N tert-butyl 3-[4-[(5r)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(O)C1=CC=C(C=2C[C@@](ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=C1 VZYFFZWXWAKARM-HSZRJFAPSA-N 0.000 claims 1
- BLNQTYRBFKDNGJ-HSZRJFAPSA-N tert-butyl 3-[4-[(5r)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(O)C1=CC=C(C=2C[C@@](ON=2)(C=2C=C(C(Cl)=C(Cl)C=2)C(F)(F)F)C(F)(F)F)C=C1 BLNQTYRBFKDNGJ-HSZRJFAPSA-N 0.000 claims 1
- UTXXCBAQFJJBKN-QHCPKHFHSA-N tert-butyl 3-[4-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(C=2C[C@](ON=2)(C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)C=C1 UTXXCBAQFJJBKN-QHCPKHFHSA-N 0.000 claims 1
- DSEMAAOAAFIAFP-QHCPKHFHSA-N tert-butyl 3-[4-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(O)C1=CC=C(C=2C[C@](ON=2)(C=2C=C(Cl)C(F)=C(Cl)C=2)C(F)(F)F)C=C1 DSEMAAOAAFIAFP-QHCPKHFHSA-N 0.000 claims 1
- AEXFKTSDPZFXKR-QHCPKHFHSA-N tert-butyl 3-[4-[(5s)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(C=2C[C@](ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=C1 AEXFKTSDPZFXKR-QHCPKHFHSA-N 0.000 claims 1
- VZYFFZWXWAKARM-QHCPKHFHSA-N tert-butyl 3-[4-[(5s)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(O)C1=CC=C(C=2C[C@](ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=C1 VZYFFZWXWAKARM-QHCPKHFHSA-N 0.000 claims 1
- BUHMMCWGFAIMAV-QHCPKHFHSA-N tert-butyl 3-[4-[(5s)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(F)C1=CC=C(C=2C[C@](ON=2)(C=2C=C(C(Cl)=C(Cl)C=2)C(F)(F)F)C(F)(F)F)C=C1 BUHMMCWGFAIMAV-QHCPKHFHSA-N 0.000 claims 1
- BLNQTYRBFKDNGJ-QHCPKHFHSA-N tert-butyl 3-[4-[(5s)-5-[3,4-dichloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1(O)C1=CC=C(C=2C[C@](ON=2)(C=2C=C(C(Cl)=C(Cl)C=2)C(F)(F)F)C(F)(F)F)C=C1 BLNQTYRBFKDNGJ-QHCPKHFHSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 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
- C07D413/02—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
- C07D413/10—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 linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261594614P | 2012-02-03 | 2012-02-03 | |
| US61/594,614 | 2012-02-03 | ||
| PCT/US2013/023673 WO2013116236A1 (en) | 2012-02-03 | 2013-01-29 | Process for the preparation of chiral isoxazoline azetidine derivatives as antiparasitic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014131950A true RU2014131950A (ru) | 2016-03-27 |
Family
ID=47679107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014131950A RU2014131950A (ru) | 2012-02-03 | 2013-01-29 | Способ получения производных хирального изоксазолин азетидина в качестве противопаразитарных агентов |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20140371464A1 (enExample) |
| EP (1) | EP2809667A1 (enExample) |
| JP (1) | JP2015505560A (enExample) |
| CN (1) | CN104169276A (enExample) |
| AR (1) | AR092793A1 (enExample) |
| AU (1) | AU2013215374A1 (enExample) |
| BR (1) | BR112014019212A8 (enExample) |
| CA (1) | CA2863629A1 (enExample) |
| CL (1) | CL2014002034A1 (enExample) |
| MX (1) | MX2014009388A (enExample) |
| RU (1) | RU2014131950A (enExample) |
| UY (1) | UY34612A (enExample) |
| WO (1) | WO2013116236A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2872989A1 (en) * | 2012-05-09 | 2013-11-14 | Zoetis Llc | Azetidine derivatives as antiparasitic agents |
| UY37137A (es) | 2016-02-24 | 2017-09-29 | Merial Inc | Compuestos antiparasitarios de isoxazolina, formulaciones inyectables de acción prolongada que los comprenden, métodos y usos de los mismos |
| DK3440062T3 (da) | 2016-04-06 | 2022-01-03 | Boehringer Ingelheim Animal Health Usa Inc | Fremgangsmåde til fremstillingen af enantiomerisk berigede isoxazolinforbindelser - krystallinsk toluensolvat af (s)-afoxolaner |
| MX380497B (es) | 2016-10-14 | 2025-03-11 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de vinil isoxazolina pesticidas y parasiticidas. |
| MX2020001724A (es) | 2017-08-14 | 2020-07-29 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos de pirazol-isoxazolina plaguicidas y parasiticidas. |
| EP3986878B1 (en) * | 2019-06-19 | 2024-09-25 | NMD Pharma A/S | Process for the preparation of clc-1 chloride channel inhibitors |
| KR20230043904A (ko) | 2020-07-24 | 2023-03-31 | 엘랑코 유에스 인코포레이티드 | 이속사졸린 화합물 및 이의 중간체의 제조 공정 |
| MX2023014962A (es) | 2021-08-11 | 2024-02-13 | Elanco Us Inc | Proceso para elaborar derivado de diaril isoxazolina. |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| CN101331127B (zh) * | 2005-12-16 | 2012-05-23 | 杜邦公司 | 用于防治无脊椎害虫的5-芳基异噁唑啉 |
| WO2007105814A1 (ja) | 2006-03-10 | 2007-09-20 | Nissan Chemical Industries, Ltd. | 置換イソキサゾリン化合物及び有害生物防除剤 |
| JP2008044880A (ja) * | 2006-08-15 | 2008-02-28 | Bayer Cropscience Ag | 殺虫性イソオキサゾリン類 |
| US8303622B2 (en) | 2007-03-14 | 2012-11-06 | St. Jude Medical, Inc. | Heart valve chordae replacement methods and apparatus |
| JP2008260691A (ja) * | 2007-04-10 | 2008-10-30 | Bayer Cropscience Ag | 殺虫性アリールイソオキサゾリン誘導体 |
| JP5365806B2 (ja) | 2007-09-10 | 2013-12-11 | 日産化学工業株式会社 | 置換イソキサゾリン化合物及び有害生物防除剤 |
| WO2009063910A1 (ja) | 2007-11-12 | 2009-05-22 | Nissan Chemical Industries, Ltd. | 光学活性イソキサゾリン化合物の触媒的不斉合成方法 |
| BRPI0923009B1 (pt) * | 2008-12-19 | 2018-07-17 | Elanco Tiergesundheit Ag | compostos de isoxazolina, composição para o controle de parasitas e uso de compostos de isoxazolina para o preparo de composição para o controle de parasitas |
| CN102822168B (zh) | 2010-02-25 | 2016-10-26 | 先正达参股股份有限公司 | 制备异恶唑啉衍生物的方法 |
| PH12013500164A1 (en) * | 2010-08-05 | 2015-07-08 | Zoetis Services Llc | Isoxazoline derivatives as antiparasitic agents |
-
2013
- 2013-01-29 WO PCT/US2013/023673 patent/WO2013116236A1/en not_active Ceased
- 2013-01-29 CN CN201380014566.3A patent/CN104169276A/zh active Pending
- 2013-01-29 JP JP2014555626A patent/JP2015505560A/ja active Pending
- 2013-01-29 AU AU2013215374A patent/AU2013215374A1/en not_active Abandoned
- 2013-01-29 CA CA2863629A patent/CA2863629A1/en not_active Abandoned
- 2013-01-29 US US14/375,056 patent/US20140371464A1/en not_active Abandoned
- 2013-01-29 BR BR112014019212A patent/BR112014019212A8/pt not_active IP Right Cessation
- 2013-01-29 RU RU2014131950A patent/RU2014131950A/ru unknown
- 2013-01-29 MX MX2014009388A patent/MX2014009388A/es unknown
- 2013-01-29 EP EP13703287.6A patent/EP2809667A1/en not_active Withdrawn
- 2013-02-01 AR ARP130100321A patent/AR092793A1/es unknown
- 2013-02-04 UY UY0001034612A patent/UY34612A/es not_active Application Discontinuation
-
2014
- 2014-07-30 CL CL2014002034A patent/CL2014002034A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20140371464A1 (en) | 2014-12-18 |
| AU2013215374A1 (en) | 2014-08-21 |
| BR112014019212A8 (pt) | 2017-07-11 |
| UY34612A (es) | 2013-09-30 |
| AR092793A1 (es) | 2015-05-06 |
| WO2013116236A1 (en) | 2013-08-08 |
| CL2014002034A1 (es) | 2014-11-14 |
| JP2015505560A (ja) | 2015-02-23 |
| CA2863629A1 (en) | 2013-08-08 |
| CN104169276A (zh) | 2014-11-26 |
| MX2014009388A (es) | 2014-08-27 |
| EP2809667A1 (en) | 2014-12-10 |
| BR112014019212A2 (enExample) | 2017-06-20 |
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