KR20140116515A - 금속효소 억제제 화합물 - Google Patents
금속효소 억제제 화합물 Download PDFInfo
- Publication number
- KR20140116515A KR20140116515A KR1020147023021A KR20147023021A KR20140116515A KR 20140116515 A KR20140116515 A KR 20140116515A KR 1020147023021 A KR1020147023021 A KR 1020147023021A KR 20147023021 A KR20147023021 A KR 20147023021A KR 20140116515 A KR20140116515 A KR 20140116515A
- Authority
- KR
- South Korea
- Prior art keywords
- tetrazol
- pyridin
- difluoro
- difluorophenyl
- propan
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 221
- 229940125956 metalloenzyme inhibitor Drugs 0.000 title 1
- -1 morpholino, pyrrolidino, piperidino Chemical group 0.000 claims description 200
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 84
- 239000000203 mixture Substances 0.000 claims description 78
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 241000196324 Embryophyta Species 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000001188 haloalkyl group Chemical group 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 18
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000002917 insecticide Substances 0.000 claims description 13
- 125000004001 thioalkyl group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 9
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 8
- 244000052769 pathogen Species 0.000 claims description 8
- 241000223218 Fusarium Species 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 230000001717 pathogenic effect Effects 0.000 claims description 7
- UBKCIXXGQRZHRO-UHFFFAOYSA-N propan-2-yl 2-aminoacetate;hydrochloride Chemical compound Cl.CC(C)OC(=O)CN UBKCIXXGQRZHRO-UHFFFAOYSA-N 0.000 claims description 7
- 241001360088 Zymoseptoria tritici Species 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 claims description 6
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 5
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- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 4
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- 241001533598 Septoria Species 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- BPPVUXSMLBXYGG-UHFFFAOYSA-N 4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1h-pyrazol-3-one Chemical compound CC1=C(C(=O)C=2C(N(C)NC=2)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 BPPVUXSMLBXYGG-UHFFFAOYSA-N 0.000 claims description 3
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
- OESCJKJXPHQMCI-UHFFFAOYSA-N 1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethylsulfanyl)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(C=2C=CC(SCC(F)(F)F)=CC=2)C=NC=1C(F)(F)C(O)CN1C=NN=N1 OESCJKJXPHQMCI-UHFFFAOYSA-N 0.000 claims description 2
- XJXWVRYXVARTIL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-fluorophenyl)pyridin-2-yl]-3-(1,2,4-triazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(F)=CC=1)(O)CN1C=NC=N1 XJXWVRYXVARTIL-UHFFFAOYSA-N 0.000 claims description 2
- JTJVHENHZMBBIO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-morpholin-4-ylphenyl)pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(=CC=1)N1CCOCC1)(O)CN1C=NN=N1 JTJVHENHZMBBIO-UHFFFAOYSA-N 0.000 claims description 2
- BSDDGMPYEBMINY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-nitrophenyl)pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(=CC=1)[N+]([O-])=O)(O)CN1C=NN=N1 BSDDGMPYEBMINY-UHFFFAOYSA-N 0.000 claims description 2
- XOPDVDHHFGXZFH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-propan-2-yloxyphenyl)pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC(C)C)=CC=C1C1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 XOPDVDHHFGXZFH-UHFFFAOYSA-N 0.000 claims description 2
- JBDKQTLQCWIBHU-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(3,3,3-trifluoropropoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OCCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 JBDKQTLQCWIBHU-UHFFFAOYSA-N 0.000 claims description 2
- NKYSEDLJBNZIFT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound OC(Cn1cnnn1)(C(F)F)c1ccc(F)cc1F NKYSEDLJBNZIFT-UHFFFAOYSA-N 0.000 claims description 2
- SCMALWNRERKPMY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-[5-(4-fluorophenyl)tetrazol-1-yl]propan-2-ol Chemical compound FC1=C(C=CC(=C1)F)C(C(F)F)(CN1N=NN=C1C1=CC=C(C=C1)F)O SCMALWNRERKPMY-UHFFFAOYSA-N 0.000 claims description 2
- HSUXUELXFIFBIT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-1-(tetrazol-1-yl)-3-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 HSUXUELXFIFBIT-UHFFFAOYSA-N 0.000 claims description 2
- XAFSRHUAOWTMSL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-3-[5-(4-fluorophenyl)pyridin-2-yl]-1-(tetrazol-1-yl)butan-2-ol Chemical compound C1=NN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(F)C=C1 XAFSRHUAOWTMSL-UHFFFAOYSA-N 0.000 claims description 2
- KYMREFHKHDOGRO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-3-fluoro-3-[5-(4-fluorophenyl)pyridin-2-yl]-1-(tetrazol-2-yl)butan-2-ol Chemical compound N1=CN=NN1CC(O)(C=1C(=CC(F)=CC=1)F)C(F)(C)C(N=C1)=CC=C1C1=CC=C(F)C=C1 KYMREFHKHDOGRO-UHFFFAOYSA-N 0.000 claims description 2
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- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
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- 239000002383 tung oil Substances 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (3)
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| US201261589064P | 2012-01-20 | 2012-01-20 | |
| US61/589,064 | 2012-01-20 | ||
| PCT/US2013/022317 WO2013110002A1 (en) | 2012-01-20 | 2013-01-18 | Metalloenzyme inhibitor compounds |
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| KR20140116515A true KR20140116515A (ko) | 2014-10-02 |
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| KR1020147023021A Withdrawn KR20140116515A (ko) | 2012-01-20 | 2013-01-18 | 금속효소 억제제 화합물 |
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Cited By (1)
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| KR20170129895A (ko) * | 2015-03-19 | 2017-11-27 | 비아멧 파마슈티컬즈, 인코포레이티드 | 항진균성 화합물 및 이의 제조 방법 |
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| TR201900242T4 (tr) | 2009-10-07 | 2019-02-21 | Dow Agrosciences Llc | Hububatta Mantarın Kontrol Altına Alınmasına Yönelik Sinerjistik Fungisidal Karışımlar |
| JP6223329B2 (ja) | 2011-06-23 | 2017-11-01 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 金属酵素化合物 |
| IN2014DN06792A (cg-RX-API-DMAC10.html) | 2012-01-20 | 2015-05-22 | Viamet Pharmaceuticals Inc | |
| PL2938191T3 (pl) | 2012-12-28 | 2018-07-31 | Dow Agrosciences Llc | Synergistyczne mieszaniny grzybobójcze do zwalczania grzybów w zbożach |
| MX2015008562A (es) | 2012-12-31 | 2015-09-07 | Dow Agrosciences Llc | Pocolinamidas macrociclicas como fungicidas. |
| WO2015100181A1 (en) | 2013-12-26 | 2015-07-02 | Dow Agrosciences Llc | Macrocyclic picolinamide compounds with fungicidal activity |
| WO2015100183A1 (en) | 2013-12-26 | 2015-07-02 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
| JP6518683B2 (ja) * | 2014-03-19 | 2019-05-22 | ヴィアメット ファーマスーティカルズ（エヌシー），インコーポレイテッド | 抗真菌化合物の調製方法 |
| AU2015231234B2 (en) * | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| US9802914B2 (en) | 2014-03-19 | 2017-10-31 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| BR112016021282A8 (pt) | 2014-03-19 | 2021-07-20 | The Us Secretary Department Of Health & Human Services | processos para a preparação de compostos antifúngicos e os referidos compostos |
| AU2015231220B2 (en) * | 2014-03-19 | 2019-04-04 | The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Antifungal compound process |
| AU2015231216B2 (en) * | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| JP6633539B2 (ja) | 2014-03-19 | 2020-01-22 | ダウ アグロサイエンシィズ エルエルシー | ２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−１−（５−置換−ピリジン−２−イル）−３−（１ｈ−テトラゾール−１−イル）プロパン−２−オールおよびその調製工程 |
| JP2017514790A (ja) * | 2014-03-19 | 2017-06-08 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 抗真菌化合物の調製方法 |
| US9914726B2 (en) | 2014-03-19 | 2018-03-13 | Vps-3, Inc. | 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1H-tetrazol-1-yl)propan-2-ols and processes for their preparation |
| EP3119745B1 (en) | 2014-03-19 | 2020-08-05 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| CA2945674A1 (en) | 2014-04-15 | 2015-10-22 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds as fungicides |
| US9663491B2 (en) | 2014-04-15 | 2017-05-30 | Dow Agrosciences Llc | Metalloenzyme inhibitor compounds as fungicides |
| BR112016025397A2 (pt) | 2014-05-06 | 2017-08-15 | Dow Agrosciences Llc | picolinamidas macrocíclicas como fungicidas |
| CN106470982A (zh) | 2014-07-08 | 2017-03-01 | 美国陶氏益农公司 | 作为杀真菌剂的大环吡啶酰胺 |
| US9686984B2 (en) | 2014-07-08 | 2017-06-27 | Dow Agrosciences Llc | Macrocyclic picolinamides as fungicides |
| US10188109B2 (en) | 2014-12-30 | 2019-01-29 | Dow Agrosciences Llc | Picolinamide compounds with fungicidal activity |
| BR112017013589A2 (pt) | 2014-12-30 | 2018-03-06 | Dow Agrosciences Llc | picolinamidas com atividade fungicida |
| CN107105654B (zh) | 2014-12-30 | 2021-03-02 | 美国陶氏益农公司 | 杀真菌组合物 |
| KR20170100620A (ko) | 2014-12-30 | 2017-09-04 | 다우 아그로사이언시즈 엘엘씨 | 살진균제로서의 피콜린아미드의 용도 |
| MX2017008422A (es) * | 2014-12-30 | 2017-10-02 | Dow Agrosciences Llc | Compuestos de picolinamida con actividad fungicida. |
| CN107426999B (zh) | 2014-12-30 | 2023-01-20 | 美国陶氏益农公司 | 具有杀真菌活性的吡啶酰胺化合物 |
| AU2016323782B2 (en) | 2015-09-18 | 2020-11-26 | Nqp 1598, Ltd. | Antifungal compound process |
| EA038421B1 (ru) * | 2015-12-30 | 2021-08-26 | ВиПиЭс-3, ИНК. | Соединения, ингибирующие металлоферменты |
| WO2018045003A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Picolinamide n-oxide compounds with fungicidal activity |
| WO2018045012A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity |
| US10172358B2 (en) | 2016-08-30 | 2019-01-08 | Dow Agrosciences Llc | Thiopicolinamide compounds with fungicidal activity |
| WO2018045000A1 (en) | 2016-08-30 | 2018-03-08 | Dow Agrosciences Llc | Picolinamides as fungicides |
| BR102018000183B1 (pt) | 2017-01-05 | 2023-04-25 | Dow Agrosciences Llc | Picolinamidas, composição para controle de um patógeno fúngico, e método para controle e prevenção de um ataque por fungos em uma planta |
| US20200045967A1 (en) * | 2017-02-08 | 2020-02-13 | Bayer Cropscience Aktiengesellschaft | Novel triazole derivatives |
| TW201842851A (zh) | 2017-05-02 | 2018-12-16 | 美商陶氏農業科學公司 | 用於穀類中的真菌防治之協同性混合物 |
| TWI774761B (zh) | 2017-05-02 | 2022-08-21 | 美商科迪華農業科技有限責任公司 | 用於穀物中的真菌防治之協同性混合物 |
| CN110996665B (zh) | 2017-05-02 | 2021-10-26 | 陶氏益农公司 | 无环吡啶酰胺化合物作为针对草坪草上的真菌病害的杀真菌剂的用途 |
| BR102019004480B1 (pt) | 2018-03-08 | 2023-03-28 | Dow Agrosciences Llc | Picolinamidas como fungicidas |
| CA3115684A1 (en) | 2018-10-15 | 2020-04-23 | Dow Agrosciences Llc | Methods for sythesis of oxypicolinamides |
| CN114554848A (zh) | 2019-10-18 | 2022-05-27 | 科迪华农业科技有限责任公司 | 用于合成吡啶酰胺的方法 |
| CN110981810A (zh) * | 2019-12-19 | 2020-04-10 | 东莞市维琪科技有限公司 | 一种脱羧肌肽的合成方法 |
| TW202140445A (zh) * | 2020-01-17 | 2021-11-01 | 大陸商上海森輝醫藥有限公司 | 四氮唑類化合物的可藥用鹽及其結晶形式、製備方法和用途 |
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| EP0117100B1 (en) * | 1983-02-16 | 1986-12-10 | Pfizer Limited | Triazole antifungal agents |
| GB8304282D0 (en) * | 1983-02-16 | 1983-03-23 | Pfizer Ltd | Antifungal agents |
| US5358939A (en) * | 1992-06-25 | 1994-10-25 | Rohm And Haas Company | Fungicidal 2-aryl-2,2-disubstituted ethyl-1,2,4-triazoles |
| MY115814A (en) | 1995-06-16 | 2003-09-30 | Bayer Ip Gmbh | Crop protection compositions |
| CN1187756A (zh) * | 1995-06-16 | 1998-07-15 | 诺瓦提斯公司 | 保护作物的组合物 |
| JP2006143593A (ja) * | 2004-11-16 | 2006-06-08 | Hokko Chem Ind Co Ltd | Ｎ−ベンジルテトラゾール誘導体および農園芸用殺菌剤 |
| WO2010005572A2 (en) * | 2008-07-09 | 2010-01-14 | The Scripps Research Institute | Alpha-keto heterocycles as faah inhibitors |
| BRPI0918058A8 (pt) * | 2008-09-03 | 2016-03-01 | Bayer Cropscience Ag | Uso de composições de composto fungicida para o controle de certos fungos da ferrugem |
| CA2785898C (en) * | 2009-12-31 | 2018-07-03 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| KR101379370B1 (ko) * | 2010-04-24 | 2014-03-28 | 비아멧 파마슈티컬즈, 인코포레이티드 | 금속효소 억제제 화합물 |
| JP6223329B2 (ja) * | 2011-06-23 | 2017-11-01 | ヴィアメット ファーマスーティカルズ，インコーポレイテッド | 金属酵素化合物 |
-
2013
- 2013-01-18 BR BR112014017799A patent/BR112014017799A8/pt not_active IP Right Cessation
- 2013-01-18 CA CA2861341A patent/CA2861341A1/en not_active Abandoned
- 2013-01-18 EA EA201491386A patent/EA201491386A1/ru unknown
- 2013-01-18 CN CN201380010205.1A patent/CN104135861A/zh active Pending
- 2013-01-18 KR KR1020147023021A patent/KR20140116515A/ko not_active Withdrawn
- 2013-01-18 WO PCT/US2013/022317 patent/WO2013110002A1/en not_active Ceased
- 2013-01-18 AU AU2013209520A patent/AU2013209520A1/en not_active Abandoned
- 2013-01-18 US US14/373,304 patent/US9414596B2/en not_active Expired - Fee Related
- 2013-01-18 EP EP13739106.6A patent/EP2804479A4/en not_active Withdrawn
- 2013-01-18 IN IN6812DEN2014 patent/IN2014DN06812A/en unknown
- 2013-01-18 MX MX2014008729A patent/MX2014008729A/es unknown
- 2013-01-18 JP JP2014553493A patent/JP2015505538A/ja not_active Ceased
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2014
- 2014-07-17 CL CL2014001892A patent/CL2014001892A1/es unknown
- 2014-07-18 PH PH12014501653A patent/PH12014501653A1/en unknown
- 2014-08-14 CO CO14178605A patent/CO7111289A2/es not_active Application Discontinuation
- 2014-08-18 EC ECIEPI201414530A patent/ECSP14014530A/es unknown
- 2014-08-18 CR CR20140387A patent/CR20140387A/es unknown
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2016
- 2016-12-15 JP JP2016243478A patent/JP2017110004A/ja active Pending
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2019
- 2019-02-05 JP JP2019018600A patent/JP2019116476A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170129895A (ko) * | 2015-03-19 | 2017-11-27 | 비아멧 파마슈티컬즈, 인코포레이티드 | 항진균성 화합물 및 이의 제조 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2013209520A1 (en) | 2014-08-28 |
| BR112014017799A8 (pt) | 2017-07-11 |
| WO2013110002A1 (en) | 2013-07-25 |
| JP2017110004A (ja) | 2017-06-22 |
| IN2014DN06812A (cg-RX-API-DMAC10.html) | 2015-05-22 |
| PH12014501653A1 (en) | 2014-10-13 |
| ECSP14014530A (es) | 2015-06-30 |
| EA201491386A1 (ru) | 2014-11-28 |
| EP2804479A1 (en) | 2014-11-26 |
| CO7111289A2 (es) | 2014-11-10 |
| BR112014017799A2 (cg-RX-API-DMAC10.html) | 2017-06-20 |
| MX2014008729A (es) | 2015-02-04 |
| JP2019116476A (ja) | 2019-07-18 |
| JP2015505538A (ja) | 2015-02-23 |
| CA2861341A1 (en) | 2013-07-25 |
| CL2014001892A1 (es) | 2014-11-14 |
| CR20140387A (es) | 2014-11-27 |
| CN104135861A (zh) | 2014-11-05 |
| US20150024938A1 (en) | 2015-01-22 |
| US9414596B2 (en) | 2016-08-16 |
| EP2804479A4 (en) | 2015-07-22 |
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