MX2014009388A - Procedimiento para la preparacion de derivados de isoxazolina azetidina quirales como agentes antiparasitarios. - Google Patents
Procedimiento para la preparacion de derivados de isoxazolina azetidina quirales como agentes antiparasitarios.Info
- Publication number
- MX2014009388A MX2014009388A MX2014009388A MX2014009388A MX2014009388A MX 2014009388 A MX2014009388 A MX 2014009388A MX 2014009388 A MX2014009388 A MX 2014009388A MX 2014009388 A MX2014009388 A MX 2014009388A MX 2014009388 A MX2014009388 A MX 2014009388A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- trifluoromethyl
- carboxylate
- dichloro
- butyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 46
- 230000008569 process Effects 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims description 21
- 239000003096 antiparasitic agent Substances 0.000 title description 5
- 229940125687 antiparasitic agent Drugs 0.000 title description 4
- LZNQKPCMSCHBFF-UHFFFAOYSA-N azetidine;4,5-dihydro-1,2-oxazole Chemical class C1CNC1.C1CC=NO1 LZNQKPCMSCHBFF-UHFFFAOYSA-N 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- -1 = S Chemical group 0.000 claims description 178
- 150000001875 compounds Chemical class 0.000 claims description 71
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 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 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 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 description 9
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 239000011737 fluorine Chemical group 0.000 claims description 9
- 229910052731 fluorine Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
- 229960000948 quinine Drugs 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- RERNBDGJFGBXFK-UHFFFAOYSA-N 3-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]-3-hydroxyazetidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CC1(O)C1=CC=C(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=C1 RERNBDGJFGBXFK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 229910003827 NRaRb Inorganic materials 0.000 claims description 8
- 125000006242 amine protecting group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- HQOVNNDBJPCDOU-UHFFFAOYSA-N 3-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]phenyl]-3-fluoroazetidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CC1(F)C1=CC=C(C=2CC(ON=2)(C=2C=C(Cl)C=C(Cl)C=2)C(F)(F)F)C=C1 HQOVNNDBJPCDOU-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 5
- KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- TVGSMPZXTCQNAB-UHFFFAOYSA-N 1-[4-(azetidin-3-yl)phenyl]-4,4,4-trifluoro-3-phenylbut-2-en-1-one Chemical class FC(F)(F)C(=CC(=O)c1ccc(cc1)C1CNC1)c1ccccc1 TVGSMPZXTCQNAB-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 4
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 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 description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- ZQQSYPZAPHRXRY-UHFFFAOYSA-N 1-hydroxyazetidine Chemical compound ON1CCC1 ZQQSYPZAPHRXRY-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- KHNGFFOEQHPXRG-UHFFFAOYSA-N 2-bromo-1-phenylazetidine Chemical compound BrC1CCN1C1=CC=CC=C1 KHNGFFOEQHPXRG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012025 fluorinating agent Substances 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 125000002053 thietanyl group Chemical group 0.000 claims description 3
- 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 description 2
- KHKPNKLHLOHKBG-WJOKGBTCSA-N (5r)-3-[4-(1-benzhydryl-3-fluoroazetidin-3-yl)phenyl]-5-(3,5-dichloro-4-fluorophenyl)-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)CN(C2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 KHKPNKLHLOHKBG-WJOKGBTCSA-N 0.000 claims description 2
- 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 description 2
- QINCLOKAVIHKJZ-HKBQPEDESA-N (5s)-3-[4-(1-benzhydryl-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=C1C(C1)(F)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 QINCLOKAVIHKJZ-HKBQPEDESA-N 0.000 claims description 2
- KHKPNKLHLOHKBG-HKBQPEDESA-N (5s)-3-[4-(1-benzhydryl-3-fluoroazetidin-3-yl)phenyl]-5-(3,5-dichloro-4-fluorophenyl)-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)CN(C2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 KHKPNKLHLOHKBG-HKBQPEDESA-N 0.000 claims description 2
- ZPMASNYEZBXLBM-HKBQPEDESA-N (5s)-3-[4-(1-benzhydryl-3-fluoroazetidin-3-yl)phenyl]-5-(3,5-dichlorophenyl)-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=C1C(C1)(F)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZPMASNYEZBXLBM-HKBQPEDESA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- DPLMQICDPYILGQ-UHFFFAOYSA-N 1-[4-(1-benzhydryl-3-fluoroazetidin-3-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1(F)CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 DPLMQICDPYILGQ-UHFFFAOYSA-N 0.000 claims description 2
- SUZWMLMQOKJORS-UHFFFAOYSA-N 1-[4-(1-benzhydryl-3-hydroxyazetidin-3-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1(O)CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1 SUZWMLMQOKJORS-UHFFFAOYSA-N 0.000 claims description 2
- AOZHVTFNXDMYRE-WJOKGBTCSA-N 1-benzhydryl-3-[4-[(5r)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C1C(O)(C=2C=CC(=CC=2)C=2C[C@@](ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 AOZHVTFNXDMYRE-WJOKGBTCSA-N 0.000 claims description 2
- WQBCZPJEJFCQOW-WJOKGBTCSA-N 1-benzhydryl-3-[4-[(5r)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol 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(C=1C=CC=CC=1)C1=CC=CC=C1 WQBCZPJEJFCQOW-WJOKGBTCSA-N 0.000 claims description 2
- AOZHVTFNXDMYRE-HKBQPEDESA-N 1-benzhydryl-3-[4-[(5s)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol Chemical compound C1C(O)(C=2C=CC(=CC=2)C=2C[C@](ON=2)(C=2C=C(Cl)C(Cl)=C(Cl)C=2)C(F)(F)F)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 AOZHVTFNXDMYRE-HKBQPEDESA-N 0.000 claims description 2
- JIBSIASZRONXMB-HKBQPEDESA-N 1-benzhydryl-3-[4-[(5s)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol 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(C=1C=CC=CC=1)C1=CC=CC=C1 JIBSIASZRONXMB-HKBQPEDESA-N 0.000 claims description 2
- WQBCZPJEJFCQOW-HKBQPEDESA-N 1-benzhydryl-3-[4-[(5s)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol 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(C=1C=CC=CC=1)C1=CC=CC=C1 WQBCZPJEJFCQOW-HKBQPEDESA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- YLZSTVIVKTXQIQ-UHFFFAOYSA-N 3-[4-[3-[3,4-dichloro-5-(trifluoromethyl)phenyl]-4,4,4-trifluorobut-2-enoyl]phenyl]-3-fluoroazetidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CC1(F)C1=CC=C(C(=O)C=C(C=2C=C(C(Cl)=C(Cl)C=2)C(F)(F)F)C(F)(F)F)C=C1 YLZSTVIVKTXQIQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000010640 amide synthesis reaction Methods 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 238000010915 one-step procedure Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims 3
- 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
- DVSSNWKOASTWTL-GOSISDBHSA-N (5r)-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-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
- JIBSIASZRONXMB-WJOKGBTCSA-N 1-benzhydryl-3-[4-[(5r)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4h-1,2-oxazol-3-yl]phenyl]azetidin-3-ol 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(C=1C=CC=CC=1)C1=CC=CC=C1 JIBSIASZRONXMB-WJOKGBTCSA-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
- ZSALDUJSGMFZPY-UHFFFAOYSA-N 2-hydroxyazetidine-1-carboxylic acid Chemical compound OC1CCN1C(O)=O ZSALDUJSGMFZPY-UHFFFAOYSA-N 0.000 claims 1
- VFRMFIIBGUUUCE-UHFFFAOYSA-N 3,4-dichloro-4,5-dihydro-1,2-oxazole Chemical compound ClC1C(=NOC1)Cl VFRMFIIBGUUUCE-UHFFFAOYSA-N 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- XAXXTYXMWOFKLW-UHFFFAOYSA-N [C-]1=CC=[NH+]1 Chemical compound [C-]1=CC=[NH+]1 XAXXTYXMWOFKLW-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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261594614P | 2012-02-03 | 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 |
|---|---|
| MX2014009388A true MX2014009388A (es) | 2014-08-27 |
Family
ID=47679107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2014009388A MX2014009388A (es) | 2012-02-03 | 2013-01-29 | Procedimiento para la preparacion de derivados de isoxazolina azetidina quirales como agentes antiparasitarios. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20140371464A1 (https=) |
| EP (1) | EP2809667A1 (https=) |
| JP (1) | JP2015505560A (https=) |
| CN (1) | CN104169276A (https=) |
| AR (1) | AR092793A1 (https=) |
| AU (1) | AU2013215374A1 (https=) |
| BR (1) | BR112014019212A8 (https=) |
| CA (1) | CA2863629A1 (https=) |
| CL (1) | CL2014002034A1 (https=) |
| MX (1) | MX2014009388A (https=) |
| RU (1) | RU2014131950A (https=) |
| UY (1) | UY34612A (https=) |
| WO (1) | WO2013116236A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013169622A1 (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 |
| ES2903286T3 (es) | 2016-04-06 | 2022-03-31 | Boehringer Ingelheim Animal Health Usa Inc | Proceso de preparación de compuestos de isoxazolina enriquecidos enantioméricamente y de solvato de tolueno cristalino de (S)-afoxolaner |
| WO2018071535A1 (en) | 2016-10-14 | 2018-04-19 | Merial, Inc. | Pesticidal and parasiticidal vinyl isoxazoline compounds |
| BR112020003217A2 (pt) | 2017-08-14 | 2020-10-06 | Boehringer Ingelheim Animal Health USA Inc. | compostos pesticidas e parasiticidas de pirazolisoxazolina |
| MX2021013507A (es) * | 2019-06-19 | 2021-12-10 | Nmd Pharma As | Proceso para la preparacion de inhibidores del canal de cloruro ciec-1. |
| KR20230043904A (ko) | 2020-07-24 | 2023-03-31 | 엘랑코 유에스 인코포레이티드 | 이속사졸린 화합물 및 이의 중간체의 제조 공정 |
| EP4384514A1 (en) | 2021-08-11 | 2024-06-19 | Elanco Us Inc. | Process for making diaryl isoxazoline derivative |
| WO2026043852A1 (en) | 2024-08-20 | 2026-02-26 | Zoetis Services Llc | Process for preparing optically enriched isoxazolines |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200804080B (en) * | 2005-12-16 | 2009-10-28 | Du Pont | 5-Aryl isoxazolines for controlling invertebrate pests |
| TW200803740A (en) | 2005-12-16 | 2008-01-16 | Du Pont | 5-aryl isoxazolines for controlling invertebrate pests |
| 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 |
| JP5365807B2 (ja) | 2007-11-12 | 2013-12-11 | 日産化学工業株式会社 | 光学活性イソキサゾリン化合物の触媒的不斉合成方法 |
| HUE015568T4 (en) * | 2008-12-19 | 2017-10-30 | Elanco Tiergesundheit Ag | Isoxazoline derivatives and their use as pesticides |
| CA2790963A1 (en) | 2010-02-25 | 2011-09-01 | Syngenta Participations Ag | Process for the preparation of isoxazoline derivatives |
| CN103270036B (zh) * | 2010-08-05 | 2015-11-25 | 佐蒂斯有限责任公司 | 作为抗寄生物剂的异噁唑啉衍生物 |
-
2013
- 2013-01-29 RU RU2014131950A patent/RU2014131950A/ru unknown
- 2013-01-29 EP EP13703287.6A patent/EP2809667A1/en not_active Withdrawn
- 2013-01-29 US US14/375,056 patent/US20140371464A1/en not_active Abandoned
- 2013-01-29 CN CN201380014566.3A patent/CN104169276A/zh active Pending
- 2013-01-29 BR BR112014019212A patent/BR112014019212A8/pt not_active IP Right Cessation
- 2013-01-29 CA CA2863629A patent/CA2863629A1/en not_active Abandoned
- 2013-01-29 AU AU2013215374A patent/AU2013215374A1/en not_active Abandoned
- 2013-01-29 WO PCT/US2013/023673 patent/WO2013116236A1/en not_active Ceased
- 2013-01-29 MX MX2014009388A patent/MX2014009388A/es unknown
- 2013-01-29 JP JP2014555626A patent/JP2015505560A/ja active Pending
- 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 |
|---|---|
| AR092793A1 (es) | 2015-05-06 |
| US20140371464A1 (en) | 2014-12-18 |
| RU2014131950A (ru) | 2016-03-27 |
| BR112014019212A2 (https=) | 2017-06-20 |
| JP2015505560A (ja) | 2015-02-23 |
| EP2809667A1 (en) | 2014-12-10 |
| AU2013215374A1 (en) | 2014-08-21 |
| BR112014019212A8 (pt) | 2017-07-11 |
| CN104169276A (zh) | 2014-11-26 |
| CL2014002034A1 (es) | 2014-11-14 |
| UY34612A (es) | 2013-09-30 |
| CA2863629A1 (en) | 2013-08-08 |
| WO2013116236A1 (en) | 2013-08-08 |
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