JP2012510520A5 - - Google Patents
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- JP2012510520A5 JP2012510520A5 JP2011539643A JP2011539643A JP2012510520A5 JP 2012510520 A5 JP2012510520 A5 JP 2012510520A5 JP 2011539643 A JP2011539643 A JP 2011539643A JP 2011539643 A JP2011539643 A JP 2011539643A JP 2012510520 A5 JP2012510520 A5 JP 2012510520A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- ring
- alkoxy
- independently
- haloalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 cyano, amino Chemical group 0.000 claims description 54
- 150000001721 carbon Chemical group 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 150000002923 oximes Chemical class 0.000 claims description 9
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- JVTSHOJDBRTPHD-UHFFFAOYSA-N 2,2,2-trifluoroacetaldehyde Chemical compound FC(F)(F)C=O JVTSHOJDBRTPHD-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 22
- 125000004434 sulfur atom Chemical group 0.000 claims 18
- 125000004429 atom Chemical group 0.000 claims 15
- 125000005842 heteroatom Chemical group 0.000 claims 14
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 13
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 5
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 5
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 4
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims 4
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 4
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims 4
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 3
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
- 125000006798 (C1-C6) haloalkylamino group Chemical group 0.000 claims 2
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- 125000006767 (C2-C6) haloalkynyloxy group Chemical group 0.000 claims 2
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 claims 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 2
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000004461 halocycloalkylalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- BHNHDPRWFJCSQM-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[3-methyl-5-(trifluoromethyl)-3,4-dihydropyrazol-2-yl]ethanone Chemical compound CC1CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 BHNHDPRWFJCSQM-UHFFFAOYSA-N 0.000 claims 1
- ICAUHPCRZVRZJY-UHFFFAOYSA-N 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]-2-[5,5-dimethyl-3-(trifluoromethyl)-4h-pyrazol-1-yl]ethanone Chemical compound CC1(C)CC(C(F)(F)F)=NN1CC(=O)N1CCC(C=2SC=C(N=2)C=2CC(ON=2)C=2C(=CC=CC=2F)F)CC1 ICAUHPCRZVRZJY-UHFFFAOYSA-N 0.000 claims 1
- LJVMOTZXULCTIO-UHFFFAOYSA-N 2-[3-[2-[1-[2-(2,2,2-trifluoroethylideneamino)oxyacetyl]piperidin-4-yl]-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl]benzonitrile Chemical compound C1CN(C(=O)CON=CC(F)(F)F)CCC1C1=NC(C=2CC(ON=2)C=2C(=CC=CC=2)C#N)=CS1 LJVMOTZXULCTIO-UHFFFAOYSA-N 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 1
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000006485 halo alkoxy phenyl group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- MHXQWAHUWKSSEG-UHFFFAOYSA-N 2-[amino(methyl)amino]-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(N)C)CCC1C1=NC(C=2CC(ON=2)C=2C(=CC=CC=2F)F)=CS1 MHXQWAHUWKSSEG-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
- VGJWVEYTYIBXIA-UHFFFAOYSA-N 2,2,2-trifluoroethane-1,1-diol Chemical compound OC(O)C(F)(F)F VGJWVEYTYIBXIA-UHFFFAOYSA-N 0.000 description 1
- BCPVBEUGUBPXFZ-UHFFFAOYSA-N 2-aminooxy-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CON)CCC1C1=NC(C=2CC(ON=2)C=2C(=CC=CC=2F)F)=CS1 BCPVBEUGUBPXFZ-UHFFFAOYSA-N 0.000 description 1
- DRWDOIPXZZFCLK-UHFFFAOYSA-N 2-chloro-1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidin-1-yl]ethanone Chemical compound FC1=CC=CC(F)=C1C1ON=C(C=2N=C(SC=2)C2CCN(CC2)C(=O)CCl)C1 DRWDOIPXZZFCLK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- YGNXYFLJZILPEK-UHFFFAOYSA-N n-cyclopentylidenehydroxylamine Chemical compound ON=C1CCCC1 YGNXYFLJZILPEK-UHFFFAOYSA-N 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11913708P | 2008-12-02 | 2008-12-02 | |
| US61/119,137 | 2008-12-02 | ||
| PCT/US2009/066318 WO2010065579A2 (en) | 2008-12-02 | 2009-12-02 | Fungicidal heterocyclic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012510520A JP2012510520A (ja) | 2012-05-10 |
| JP2012510520A5 true JP2012510520A5 (https=) | 2013-01-17 |
| JP5592894B2 JP5592894B2 (ja) | 2014-09-17 |
Family
ID=42008531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011539643A Active JP5592894B2 (ja) | 2008-12-02 | 2009-12-02 | 殺真菌性複素環化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8618137B2 (https=) |
| EP (1) | EP2358709B1 (https=) |
| JP (1) | JP5592894B2 (https=) |
| KR (1) | KR101716514B1 (https=) |
| CN (1) | CN102227423B (https=) |
| AR (1) | AR074411A1 (https=) |
| AU (1) | AU2009322486A1 (https=) |
| BR (1) | BRPI0914405B8 (https=) |
| CL (1) | CL2011001272A1 (https=) |
| ES (1) | ES2452299T3 (https=) |
| IL (1) | IL212186A0 (https=) |
| MX (1) | MX2011005598A (https=) |
| PL (1) | PL2358709T3 (https=) |
| TW (1) | TW201036966A (https=) |
| UY (1) | UY32285A (https=) |
| WO (1) | WO2010065579A2 (https=) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2012007200A (es) | 2009-12-21 | 2012-07-10 | Bayer Cropscience Ag | Bis(difluorometil)pirazoles como fungicidas. |
| BR112012027762B1 (pt) | 2010-04-28 | 2018-06-05 | Bayer Intellectual Property Gmbh | Derivados de cetoheteroarilpiperidina e - piperazina como fungicidas |
| EP2576539B1 (de) | 2010-05-27 | 2017-12-13 | Bayer CropScience AG | Pyridinylcarbonsäure derivate als fungizide |
| US20120122928A1 (en) | 2010-08-11 | 2012-05-17 | Bayer Cropscience Ag | Heteroarylpiperidine and -Piperazine Derivatives as Fungicides |
| EP2423210A1 (de) | 2010-08-25 | 2012-02-29 | Bayer CropScience AG | Heteroarylpiperidin- und -piperazinderivate als Fungizide |
| US8759527B2 (en) | 2010-08-25 | 2014-06-24 | Bayer Cropscience Ag | Heteroarylpiperidine and -piperazine derivatives as fungicides |
| EP2632922B1 (de) | 2010-10-27 | 2019-02-27 | Bayer CropScience Aktiengesellschaft | Heteroarylpiperidin und -piperazinderivate als fungizide |
| CN103384470A (zh) * | 2010-12-17 | 2013-11-06 | 纳幕尔杜邦公司 | 杀真菌偶氮环酰胺 |
| WO2012104273A1 (de) * | 2011-02-01 | 2012-08-09 | Bayer Cropscience Ag | Heteroarylpiperidin und -piperazinderivate als fungizide |
| US10004232B2 (en) | 2011-09-15 | 2018-06-26 | Bayer Intellectual Property Gmbh | Piperidine pyrazoles as fungicides |
| DK2797899T3 (en) | 2011-12-27 | 2016-04-04 | Bayer Ip Gmbh | Heteroarylpiperidin and -piperazinderivater as fungicides |
| US9266876B2 (en) | 2012-02-02 | 2016-02-23 | Actelion Pharmaceuticals Ltd. | 4-(benzoimidazol-2-yl)-thiazole compounds and related aza derivatives |
| MX360174B (es) * | 2012-02-27 | 2018-10-12 | Bayer Ip Gmbh | Combinaciones de compuestos activos que contienen una tiazolilisoxazolina y un fungicida. |
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2009
- 2009-12-02 AU AU2009322486A patent/AU2009322486A1/en not_active Abandoned
- 2009-12-02 PL PL09764158T patent/PL2358709T3/pl unknown
- 2009-12-02 UY UY0001032285A patent/UY32285A/es not_active Application Discontinuation
- 2009-12-02 EP EP09764158.3A patent/EP2358709B1/en active Active
- 2009-12-02 TW TW098141182A patent/TW201036966A/zh unknown
- 2009-12-02 MX MX2011005598A patent/MX2011005598A/es active IP Right Grant
- 2009-12-02 BR BRPI0914405A patent/BRPI0914405B8/pt not_active IP Right Cessation
- 2009-12-02 WO PCT/US2009/066318 patent/WO2010065579A2/en not_active Ceased
- 2009-12-02 AR ARP090104654A patent/AR074411A1/es active IP Right Grant
- 2009-12-02 KR KR1020117015240A patent/KR101716514B1/ko not_active Expired - Fee Related
- 2009-12-02 US US13/127,809 patent/US8618137B2/en active Active
- 2009-12-02 ES ES09764158.3T patent/ES2452299T3/es active Active
- 2009-12-02 JP JP2011539643A patent/JP5592894B2/ja active Active
- 2009-12-02 CN CN200980148160.8A patent/CN102227423B/zh not_active Expired - Fee Related
-
2011
- 2011-04-06 IL IL212186A patent/IL212186A0/en unknown
- 2011-05-31 CL CL2011001272A patent/CL2011001272A1/es unknown
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