CA2861341A1 - Metalloenzyme inhibitor compounds against fungal infection induced plant diseases and method of use thereof - Google Patents

Info

Publication number

CA2861341A1

CA2861341A1 CA2861341A CA2861341A CA2861341A1 CA 2861341 A1 CA2861341 A1 CA 2861341A1 CA 2861341 A CA2861341 A CA 2861341A CA 2861341 A CA2861341 A CA 2861341A CA 2861341 A1 CA2861341 A1 CA 2861341A1

Authority

CA

Canada

Prior art keywords

pyridin

tetrazol

difluorophenyl

difluoro

propan

Prior art date

2012-01-20

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 238000000034 method Methods 0.000 title claims description 39
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 26
• 201000010099 disease Diseases 0.000 title claims description 19
• 150000001875 compounds Chemical class 0.000 title abstract description 210
• 208000031888 Mycoses Diseases 0.000 title description 2
• 229940125956 metalloenzyme inhibitor Drugs 0.000 title description 2
• 206010017533 Fungal infection Diseases 0.000 title 1
• 239000000203 mixture Substances 0.000 claims description 91
• -1 morpholino, pyrrolidino, piperidino Chemical group 0.000 claims description 87
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 78
• 125000000217 alkyl group Chemical group 0.000 claims description 52
• 241000196324 Embryophyta Species 0.000 claims description 43
• 125000001188 haloalkyl group Chemical group 0.000 claims description 33
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 26
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 14
• 125000001153 fluoro group Chemical group F* 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 11
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 11
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 11
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 11
• 244000052769 pathogen Species 0.000 claims description 11
• 125000004001 thioalkyl group Chemical group 0.000 claims description 11
• 230000001717 pathogenic effect Effects 0.000 claims description 10
• 241000209140 Triticum Species 0.000 claims description 7
• 235000021307 Triticum Nutrition 0.000 claims description 7
• 241001360088 Zymoseptoria tritici Species 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000001425 triazolyl group Chemical group 0.000 claims description 5
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
• 241000510928 Erysiphe necator Species 0.000 claims description 4
• 241000223218 Fusarium Species 0.000 claims description 4
• 241000228453 Pyrenophora Species 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 239000002917 insecticide Substances 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 235000017060 Arachis glabrata Nutrition 0.000 claims description 3
• 244000105624 Arachis hypogaea Species 0.000 claims description 3
• 235000010777 Arachis hypogaea Nutrition 0.000 claims description 3
• 235000018262 Arachis monticola Nutrition 0.000 claims description 3
• 241001533598 Septoria Species 0.000 claims description 3
• 244000053095 fungal pathogen Species 0.000 claims description 3
• 235000020232 peanut Nutrition 0.000 claims description 3
• 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 2
• 241000223600 Alternaria Species 0.000 claims description 2
• 241000228212 Aspergillus Species 0.000 claims description 2
• 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 2
• 241001480060 Blumeria Species 0.000 claims description 2
• 241001480061 Blumeria graminis Species 0.000 claims description 2
• 241001465180 Botrytis Species 0.000 claims description 2
• 241001157813 Cercospora Species 0.000 claims description 2
• 241000530549 Cercospora beticola Species 0.000 claims description 2
• 241000222290 Cladosporium Species 0.000 claims description 2
• 241000228437 Cochliobolus Species 0.000 claims description 2
• 241000222199 Colletotrichum Species 0.000 claims description 2
• 241000222235 Colletotrichum orbiculare Species 0.000 claims description 2
• 240000008067 Cucumis sativus Species 0.000 claims description 2
• 235000010799 Cucumis sativus var sativus Nutrition 0.000 claims description 2
• 241000371644 Curvularia ravenelii Species 0.000 claims description 2
• 241000221785 Erysiphales Species 0.000 claims description 2
• 241000221787 Erysiphe Species 0.000 claims description 2
• 241000306559 Exserohilum Species 0.000 claims description 2
• 241000221557 Gymnosporangium Species 0.000 claims description 2
• 241001181537 Hemileia Species 0.000 claims description 2
• 241001344133 Magnaporthe Species 0.000 claims description 2
• 241000131448 Mycosphaerella Species 0.000 claims description 2
• 241000315044 Passalora arachidicola Species 0.000 claims description 2
• 241000228143 Penicillium Species 0.000 claims description 2
• 241000555275 Phaeosphaeria Species 0.000 claims description 2
• 241000440444 Phakopsora Species 0.000 claims description 2
• 241000896242 Podosphaera Species 0.000 claims description 2
• 241000087479 Pseudocercospora fijiensis Species 0.000 claims description 2
• 241000682843 Pseudocercosporella Species 0.000 claims description 2
• 241000221300 Puccinia Species 0.000 claims description 2
• 241000231139 Pyricularia Species 0.000 claims description 2
• 241000173767 Ramularia Species 0.000 claims description 2
• 241001361634 Rhizoctonia Species 0.000 claims description 2
• 206010039509 Scab Diseases 0.000 claims description 2
• 241000221662 Sclerotinia Species 0.000 claims description 2
• 241000579741 Sphaerotheca <fungi> Species 0.000 claims description 2
• 241000533281 Stagonospora Species 0.000 claims description 2
• 235000021536 Sugar beet Nutrition 0.000 claims description 2
• 241000510929 Uncinula Species 0.000 claims description 2
• 241000221576 Uromyces Species 0.000 claims description 2
• 241000221566 Ustilago Species 0.000 claims description 2
• 241000317942 Venturia <ichneumonid wasp> Species 0.000 claims description 2
• 241000228452 Venturia inaequalis Species 0.000 claims description 2
• JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
• IDUYJRXRDSPPRC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)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(OCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 IDUYJRXRDSPPRC-UHFFFAOYSA-N 0.000 claims 4
• IEYCWUALSWPHDI-UHFFFAOYSA-N 1-[4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenyl]-2,2,2-trifluoroethanone Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(=CC=1)C(=O)C(F)(F)F)(O)CN1C=NN=N1 IEYCWUALSWPHDI-UHFFFAOYSA-N 0.000 claims 2
• GNIKWJWEACQTNW-UHFFFAOYSA-N 1-[5-(3-chlorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-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=C(Cl)C=CC=1)(O)CN1C=NN=N1 GNIKWJWEACQTNW-UHFFFAOYSA-N 0.000 claims 2
• QFSIEMVDJIQESH-UHFFFAOYSA-N 1-[5-(4-chloro-3-fluorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-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=C(F)C(Cl)=CC=1)(O)CN1C=NN=N1 QFSIEMVDJIQESH-UHFFFAOYSA-N 0.000 claims 2
• BNRLEARACNMGQQ-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-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(Cl)=CC=1)(O)CN1C=NN=N1 BNRLEARACNMGQQ-UHFFFAOYSA-N 0.000 claims 2
• SGIOKLOTIKJJFS-UHFFFAOYSA-N 1-[5-[3-(difluoromethoxy)phenyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-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=C(OC(F)F)C=CC=1)(O)CN1C=NN=N1 SGIOKLOTIKJJFS-UHFFFAOYSA-N 0.000 claims 2
• LTGBNLMVVAFZGT-UHFFFAOYSA-N 1-[5-[4-(difluoromethoxy)phenyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-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(OC(F)F)=CC=1)(O)CN1C=NN=N1 LTGBNLMVVAFZGT-UHFFFAOYSA-N 0.000 claims 2
• BLPPSIFFRCQAID-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-phenylpyridin-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)(O)CN1C=NN=N1 BLPPSIFFRCQAID-UHFFFAOYSA-N 0.000 claims 2
• WQUYGTAEQHYDSV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(3-propan-2-ylphenyl)pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound CC(C)C1=CC=CC(C=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 WQUYGTAEQHYDSV-UHFFFAOYSA-N 0.000 claims 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 2
• LIFCTIRUKQXXCV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-fluorophenyl)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(F)=CC=1)(O)CN1C=NN=N1 LIFCTIRUKQXXCV-UHFFFAOYSA-N 0.000 claims 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 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 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 2
• YTYDYXBYPZKLBW-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[4-(2,2,3,3,3-pentafluoropropoxy)phenyl]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(OCC(F)(F)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 YTYDYXBYPZKLBW-UHFFFAOYSA-N 0.000 claims 2
• YQTJCWNNHNJRAY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[4-[(2-methylpropan-2-yl)oxy]phenyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC(C)(C)C)=CC=C1C1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 YQTJCWNNHNJRAY-UHFFFAOYSA-N 0.000 claims 2
• MSRICOSVBSYAJO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)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(OCC(F)(F)F)=CC=1)(O)CN1C=NC=N1 MSRICOSVBSYAJO-UHFFFAOYSA-N 0.000 claims 2
• JJHAQEOFFYLRAX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)-1-[5-[4-(trifluoromethoxy)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(OC(F)(F)F)=CC=1)(O)CN1C=NC=N1 JJHAQEOFFYLRAX-UHFFFAOYSA-N 0.000 claims 2
• XJOUOULZTJKLNL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1h-pyrazol-5-yl)-1-[5-[4-(trifluoromethoxy)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(OC(F)(F)F)=CC=1)(O)CC=1C=CNN=1 XJOUOULZTJKLNL-UHFFFAOYSA-N 0.000 claims 2
• HSOHUDGZYOVUTH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[3-(trifluoromethoxy)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=C(OC(F)(F)F)C=CC=1)(O)CN1C=NN=N1 HSOHUDGZYOVUTH-UHFFFAOYSA-N 0.000 claims 2
• CAXYCUMJWGYZCQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[3-(trifluoromethyl)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=C(C=CC=1)C(F)(F)F)(O)CN1C=NN=N1 CAXYCUMJWGYZCQ-UHFFFAOYSA-N 0.000 claims 2
• NGSZMSSFJMJEPD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethyl)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(CC(F)(F)F)=CC=1)(O)CN1C=NN=N1 NGSZMSSFJMJEPD-UHFFFAOYSA-N 0.000 claims 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 2
• NCEHACHJIXJSPD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)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(OC(F)(F)F)=CC=1)(O)CN1C=NN=N1 NCEHACHJIXJSPD-UHFFFAOYSA-N 0.000 claims 2
• WJGQBRYSRQIYNV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethyl)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(=CC=1)C(F)(F)F)(O)CN1C=NN=N1 WJGQBRYSRQIYNV-UHFFFAOYSA-N 0.000 claims 2
• LKQHUNBIFMSONG-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethylsulfanyl)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(SC(F)(F)F)=CC=1)(O)CN1C=NN=N1 LKQHUNBIFMSONG-UHFFFAOYSA-N 0.000 claims 2
• GJRJJAXJYBRRHV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)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(OCC(F)(F)F)=CC=1)(O)CN1N=CN=N1 GJRJJAXJYBRRHV-UHFFFAOYSA-N 0.000 claims 2
• GJSQDETZKLKYHM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(triazol-1-yl)-1-[5-[4-(trifluoromethoxy)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(OC(F)(F)F)=CC=1)(O)CN1C=CN=N1 GJSQDETZKLKYHM-UHFFFAOYSA-N 0.000 claims 2
• UHZQCOJUZBONSC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-(2,5-difluorophenyl)pyridin-2-yl]-1,1-difluoro-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=C(F)C=1)F)(O)CN1C=NN=N1 UHZQCOJUZBONSC-UHFFFAOYSA-N 0.000 claims 2
• BOCNJXGUWFXJLX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-(3,4-difluorophenyl)pyridin-2-yl]-1,1-difluoro-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=C(F)C(F)=CC=1)(O)CN1C=NN=N1 BOCNJXGUWFXJLX-UHFFFAOYSA-N 0.000 claims 2
• QBUDANSQCYSGLX-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CN1C=NN=N1 QBUDANSQCYSGLX-UHFFFAOYSA-N 0.000 claims 2
• WCLFRXGODMAGSI-UHFFFAOYSA-N 3-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C=1C=C(C=CC=1)C#N)(O)CN1C=NN=N1 WCLFRXGODMAGSI-UHFFFAOYSA-N 0.000 claims 2
• PDUNABKLLIZVMV-UHFFFAOYSA-N 3-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]phenol Chemical compound OC1=CC=CC(C=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 PDUNABKLLIZVMV-UHFFFAOYSA-N 0.000 claims 2
• ZEWMNAWCDVMJPW-UHFFFAOYSA-N 4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 ZEWMNAWCDVMJPW-UHFFFAOYSA-N 0.000 claims 2
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