JP2014523880A5 - - Google Patents
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- JP2014523880A5 JP2014523880A5 JP2014517113A JP2014517113A JP2014523880A5 JP 2014523880 A5 JP2014523880 A5 JP 2014523880A5 JP 2014517113 A JP2014517113 A JP 2014517113A JP 2014517113 A JP2014517113 A JP 2014517113A JP 2014523880 A5 JP2014523880 A5 JP 2014523880A5
- Authority
- JP
- Japan
- Prior art keywords
- difluoro
- difluorophenyl
- tetrazol
- optionally substituted
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 44
- 125000001072 heteroaryl group Chemical group 0.000 claims 27
- 125000005843 halogen group Chemical group 0.000 claims 23
- 125000001188 haloalkyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 10
- 125000004438 haloalkoxy group Chemical group 0.000 claims 10
- 125000004001 thioalkyl group Chemical group 0.000 claims 10
- 235000019000 fluorine Nutrition 0.000 claims 8
- -1 flutriaphor Chemical compound 0.000 claims 8
- 241000196324 Embryophyta Species 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 5
- 235000010290 biphenyl Nutrition 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims 5
- 125000000232 haloalkynyl group Chemical group 0.000 claims 5
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000001425 triazolyl group Chemical group 0.000 claims 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 4
- 241000894007 species Species 0.000 claims 4
- 241000209140 Triticum Species 0.000 claims 3
- 235000021307 Triticum Nutrition 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 244000005700 microbiome Species 0.000 claims 3
- OGJSRSSAVVZZNA-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[4-(4-fluorophenyl)phenyl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1C=CC(=CC=1)C=1C=CC(F)=CC=1)(O)CN1C=NN=N1 OGJSRSSAVVZZNA-UHFFFAOYSA-N 0.000 claims 2
- 241000510928 Erysiphe necator Species 0.000 claims 2
- 241000223218 Fusarium Species 0.000 claims 2
- 241000131448 Mycosphaerella Species 0.000 claims 2
- 241000221300 Puccinia Species 0.000 claims 2
- 241000231139 Pyricularia Species 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000002538 fungal effect Effects 0.000 claims 2
- 230000000855 fungicidal effect Effects 0.000 claims 2
- 239000000417 fungicide Substances 0.000 claims 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 2
- ZMYFCFLJBGAQRS-IRXDYDNUSA-N (2R,3S)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IRXDYDNUSA-N 0.000 claims 1
- ZAHUSXVPZMFMSF-UHFFFAOYSA-N 1,1-difluoro-2-(4-fluorophenyl)-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]pyrazin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(C(F)(F)C=1N=CC(=NC=1)C=1C=CC(OC(F)(F)F)=CC=1)(O)CN1C=NN=N1 ZAHUSXVPZMFMSF-UHFFFAOYSA-N 0.000 claims 1
- BSWSAXNDRRRWHT-UHFFFAOYSA-N 1-(1,3-benzothiazol-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=1SC2=CC=CC=C2N=1)(O)CN1C=NN=N1 BSWSAXNDRRRWHT-UHFFFAOYSA-N 0.000 claims 1
- PRPKWVAYXRKYPZ-UHFFFAOYSA-N 1-(4-bromo-1,3-thiazol-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=1SC=C(Br)N=1)(O)CN1C=NN=N1 PRPKWVAYXRKYPZ-UHFFFAOYSA-N 0.000 claims 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims 1
- IJWUZGPWBQCMCV-UHFFFAOYSA-N 1-(5,6-dichloroquinolin-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=C2C=CC(Cl)=C(Cl)C2=CC=1)(O)CN1C=NN=N1 IJWUZGPWBQCMCV-UHFFFAOYSA-N 0.000 claims 1
- PQZSGYYELIGLCJ-UHFFFAOYSA-N 1-(5-bromothiophen-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=1SC(Br)=CC=1)(O)CN1C=NN=N1 PQZSGYYELIGLCJ-UHFFFAOYSA-N 0.000 claims 1
- QXDLOJRAQLRLBT-UHFFFAOYSA-N 1-(5-chloropyrazin-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(Cl)=NC=1)(O)CN1C=NN=N1 QXDLOJRAQLRLBT-UHFFFAOYSA-N 0.000 claims 1
- CRSUVPIGFCLECU-UHFFFAOYSA-N 1-(5-chloroquinolin-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=C2C=CC=C(Cl)C2=CC=1)(O)CN1C=NN=N1 CRSUVPIGFCLECU-UHFFFAOYSA-N 0.000 claims 1
- MSWUQKNAWRQPCE-UHFFFAOYSA-N 1-(5-chlorothiophen-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=1SC(Cl)=CC=1)(O)CN1C=NN=N1 MSWUQKNAWRQPCE-UHFFFAOYSA-N 0.000 claims 1
- SNJWBEVAANRMGD-UHFFFAOYSA-N 1-(6-bromo-1,3-benzothiazol-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=1SC2=CC(Br)=CC=C2N=1)(O)CN1C=NN=N1 SNJWBEVAANRMGD-UHFFFAOYSA-N 0.000 claims 1
- GWVCFCRFDMCWAG-UHFFFAOYSA-N 1-(6-bromoquinolin-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=C2C=CC(Br)=CC2=CC=1)(O)CN1C=NN=N1 GWVCFCRFDMCWAG-UHFFFAOYSA-N 0.000 claims 1
- CGQRRXIQHKQABV-UHFFFAOYSA-N 1-(6-bromoquinoxalin-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=C2C=CC(Br)=CC2=NC=1)(O)CN1C=NN=N1 CGQRRXIQHKQABV-UHFFFAOYSA-N 0.000 claims 1
- VWIDQLCQMLJPJT-UHFFFAOYSA-N 1-(6-chloro-1,3-benzothiazol-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=1SC2=CC(Cl)=CC=C2N=1)(O)CN1C=NN=N1 VWIDQLCQMLJPJT-UHFFFAOYSA-N 0.000 claims 1
- DISWUHUIHBBZPN-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-1,1-difluoro-2-(4-fluorophenyl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=CC=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=N1 DISWUHUIHBBZPN-UHFFFAOYSA-N 0.000 claims 1
- NOFDPNWFRGLYTK-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-1,1-difluoro-2-(4-methoxyphenyl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC)=CC=C1C(O)(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)CN1N=NN=C1 NOFDPNWFRGLYTK-UHFFFAOYSA-N 0.000 claims 1
- QRKOVNZOQNNGJY-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-1,1-difluoro-2-[2-fluoro-4-(trifluoromethyl)phenyl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(C(F)(F)F)C=C(F)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=N1 QRKOVNZOQNNGJY-UHFFFAOYSA-N 0.000 claims 1
- DWWBHYCWKISDQJ-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-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=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NC=N1 DWWBHYCWKISDQJ-UHFFFAOYSA-N 0.000 claims 1
- FBMNHICXWINQQQ-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-4-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=C1 FBMNHICXWINQQQ-UHFFFAOYSA-N 0.000 claims 1
- SRBBDMDDBINJKI-UHFFFAOYSA-N 1-(6-chloroquinolin-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=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=N1 SRBBDMDDBINJKI-UHFFFAOYSA-N 0.000 claims 1
- AQTFAULFKXBOEC-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1N=CN=N1 AQTFAULFKXBOEC-UHFFFAOYSA-N 0.000 claims 1
- VTBQSKCJQUNDHA-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-(2,5-difluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C(F)=CC=C(F)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1N=CN=N1 VTBQSKCJQUNDHA-UHFFFAOYSA-N 0.000 claims 1
- UKPFJMNQOUIOFT-UHFFFAOYSA-N 1-(6-chloroquinolin-2-yl)-2-[2-chloro-4-(trifluoromethyl)phenyl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(C(F)(F)F)C=C(Cl)C=1C(C(F)(F)C=1N=C2C=CC(Cl)=CC2=CC=1)(O)CN1C=NN=N1 UKPFJMNQOUIOFT-UHFFFAOYSA-N 0.000 claims 1
- XJBIYNPVUFIELG-UHFFFAOYSA-N 1-(6-chloroquinoxalin-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=C2C=CC(Cl)=CC2=NC=1)(O)CN1C=NN=N1 XJBIYNPVUFIELG-UHFFFAOYSA-N 0.000 claims 1
- CJJPANKYCQOBAK-UHFFFAOYSA-N 1-(7-chloroisoquinolin-3-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=CC2=CC(Cl)=CC=C2C=1)(O)CN1C=NN=N1 CJJPANKYCQOBAK-UHFFFAOYSA-N 0.000 claims 1
- RYUBZLWHLBOAIJ-UHFFFAOYSA-N 1-[5-(4-bromophenyl)pyrazin-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(=NC=1)C=1C=CC(Br)=CC=1)(O)CN1C=NN=N1 RYUBZLWHLBOAIJ-UHFFFAOYSA-N 0.000 claims 1
- SFANIAZLOAGMGY-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)pyrazin-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(=NC=1)C=1C=CC(Cl)=CC=1)(O)CN1C=NN=N1 SFANIAZLOAGMGY-UHFFFAOYSA-N 0.000 claims 1
- FUXCBKALBDKNQA-UHFFFAOYSA-N 1-[5-[4-(difluoromethoxy)phenyl]pyrazin-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(=NC=1)C=1C=CC(OC(F)F)=CC=1)(O)CN1C=NN=N1 FUXCBKALBDKNQA-UHFFFAOYSA-N 0.000 claims 1
- OWJJEBKOZTVUJO-UHFFFAOYSA-N 1-[6-(difluoromethyl)quinolin-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=C2C=CC(=CC2=CC=1)C(F)F)(O)CN1C=NN=N1 OWJJEBKOZTVUJO-UHFFFAOYSA-N 0.000 claims 1
- WDNZYDPCYQMVFY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(6-fluoroquinolin-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=C2C=CC(F)=CC2=CC=1)(O)CN1C=NN=N1 WDNZYDPCYQMVFY-UHFFFAOYSA-N 0.000 claims 1
- UZRGYSSSYMJPJN-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(6-fluoroquinoxalin-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=C2C=CC(F)=CC2=NC=1)(O)CN1C=NN=N1 UZRGYSSSYMJPJN-UHFFFAOYSA-N 0.000 claims 1
- DJMRCOHIQJQRNB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(6-methylquinolin-2-yl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC2=CC(C)=CC=C2N=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1C=NN=N1 DJMRCOHIQJQRNB-UHFFFAOYSA-N 0.000 claims 1
- SPXYZHSJGNFPNQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-fluorophenyl)pyrazin-2-yl]-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=NC=1)C=1C=CC(F)=CC=1)(O)CN1N=CN=N1 SPXYZHSJGNFPNQ-UHFFFAOYSA-N 0.000 claims 1
- JLHUZXNJGGGINI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(4-methoxyphenyl)pyrazin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC)=CC=C1C1=CN=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=N1 JLHUZXNJGGGINI-UHFFFAOYSA-N 0.000 claims 1
- MNNPKXJRKFWZAA-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-(4-fluorophenyl)ethyl]pyrazin-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(CCC=2C=CC(F)=CC=2)=NC=1)(O)CN1C=NN=N1 MNNPKXJRKFWZAA-UHFFFAOYSA-N 0.000 claims 1
- DUSGQISEKVGKFY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-(4-fluorophenyl)ethyl]pyrazin-2-yl]-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(CCC=2C=CC(F)=CC=2)=NC=1)(O)CN1N=CN=N1 DUSGQISEKVGKFY-UHFFFAOYSA-N 0.000 claims 1
- AKIJOMXPTBDWHL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-(4-fluorophenyl)ethynyl]pyrazin-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(=NC=1)C#CC=1C=CC(F)=CC=1)(O)CN1C=NN=N1 AKIJOMXPTBDWHL-UHFFFAOYSA-N 0.000 claims 1
- LEKFFQGYDLBDCX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-(4-fluorophenyl)ethynyl]pyrazin-2-yl]-3-(tetrazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=NC=1)C#CC=1C=CC(F)=CC=1)(O)CN1N=CN=N1 LEKFFQGYDLBDCX-UHFFFAOYSA-N 0.000 claims 1
- JMBMKGWQEWYALI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[6-(4-fluorophenyl)pyridazin-3-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=NC(=CC=1)C=1C=CC(F)=CC=1)(O)CN1C=NN=N1 JMBMKGWQEWYALI-UHFFFAOYSA-N 0.000 claims 1
- UZYJYHPEBHBKRD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-pyrimidin-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=CN=1)(O)CN1C=NN=N1 UZYJYHPEBHBKRD-UHFFFAOYSA-N 0.000 claims 1
- GPLQUAMQMYCLMQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-quinolin-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=C2C=CC=CC2=CC=1)(O)CN1C=NN=N1 GPLQUAMQMYCLMQ-UHFFFAOYSA-N 0.000 claims 1
- FOZAIQXJYUGLJS-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-(1,3-thiazol-2-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1SC=CN=1)(O)CN1C=NN=N1 FOZAIQXJYUGLJS-UHFFFAOYSA-N 0.000 claims 1
- DCYAGIBHSJIZOZ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[4-[4-(2,2,2-trifluoroethoxy)phenyl]phenyl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1C=CC(=CC=1)C=1C=CC(OCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 DCYAGIBHSJIZOZ-UHFFFAOYSA-N 0.000 claims 1
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| CA2709257C (en) | 2007-12-19 | 2016-12-13 | Cancer Research Technology Limited | Pyrido[2,3-b]pyrazine-8-substituted compounds and their use |
| ES2469367T3 (es) | 2010-02-01 | 2014-06-18 | Cancer Research Technology Limited | 1-(5-Terc-butil-2-fenil-2H-pirazol-3-il)-3-[2-fluoro-4-(1-metil-2-oxo-2,3-dihidro-1H-imidazo[4,5-b]piridin-7-iloxi)-fenil]-urea y compuestos relacionados y su uso en terapia |
| EA201490038A1 (ru) | 2011-06-19 | 2014-04-30 | Вайамет Фармасьютикалс, Инк. | Соединения, ингибирующие металлоферменты |
| AU2012273004B2 (en) * | 2011-06-23 | 2017-04-13 | Mycovia Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| KR102070345B1 (ko) | 2011-12-11 | 2020-01-28 | 마이코비아 파마슈티컬즈, 인코포레이티드 | 금속효소 억제제 화합물 |
| EA201491386A1 (ru) | 2012-01-20 | 2014-11-28 | Вайамет Фармасьютикалс, Инк. | Соединения, ингибирующие металлоферменты |
| CN104136427B (zh) * | 2012-01-20 | 2017-03-01 | 威尔金制药有限公司 | 金属酶抑制剂化合物 |
| WO2013135674A1 (en) * | 2012-03-12 | 2013-09-19 | Syngenta Participations Ag | Insecticidal 2-aryl-acetamide compounds |
| JP6404235B2 (ja) * | 2013-02-04 | 2018-10-10 | シンジェンタ パーティシペーションズ アーゲー | 新規な殺微生物剤 |
| EP2984082B1 (en) | 2013-04-12 | 2017-08-02 | Bayer CropScience Aktiengesellschaft | Novel triazole derivatives |
| WO2014167009A1 (en) | 2013-04-12 | 2014-10-16 | Bayer Cropscience Ag | Novel triazole derivatives |
| JP2016522800A (ja) | 2013-04-12 | 2016-08-04 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 新規トリアゾリンチオン誘導体 |
| JP6387401B2 (ja) * | 2013-05-28 | 2018-09-05 | 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 | 殺真菌組成物 |
| CA2915054A1 (en) * | 2013-06-12 | 2014-12-18 | Viamet Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| GB201320732D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Methods of chemical synthesis |
| GB201320729D0 (en) | 2013-11-25 | 2014-01-08 | Cancer Rec Tech Ltd | Therapeutic compounds and their use |
| AR099120A1 (es) | 2014-01-20 | 2016-06-29 | Bayer Cropscience Ag | Derivados de quinolina como insecticidas y acaricidas |
| CA2942972A1 (en) | 2014-03-19 | 2015-09-24 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Antifungal compound process |
| AU2015231270B2 (en) * | 2014-03-19 | 2019-03-07 | Viamet Pharmaceuticals (NC), Inc. | Antifungal compound process |
| KR102151082B1 (ko) * | 2014-03-19 | 2020-09-03 | 더 유나이티드 스테이츠 오브 어메리카, 애즈 리프리젠티드 바이 더 시크리터리, 디파트먼트 오브 헬쓰 앤드 휴먼 서비시스 | 항진균 화합물 제조방법 |
| AU2015231216B2 (en) * | 2014-03-19 | 2019-04-04 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| US10017494B2 (en) | 2014-03-19 | 2018-07-10 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| EA201691648A1 (ru) | 2014-03-19 | 2017-01-30 | Ваймет Фармасьютикалс, Инк. | Способ получения противогрибковых соединений |
| EP3119756B9 (en) | 2014-03-19 | 2021-08-25 | Dow AgroSciences LLC | 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 |
| AU2015231275B2 (en) | 2014-03-19 | 2019-03-07 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| JP2017507991A (ja) | 2014-03-19 | 2017-03-23 | 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 |
| BR112016021257B1 (pt) | 2014-03-19 | 2021-03-02 | Viamet Pharmaceuticals (NC), Inc. | 2-(2,4- difluorofenil-1,1-diflúor-1-(5-substituído-piridin-2-il)-3- (1h-tetrazol-1-il)propan-2-óis e processos para preparação e uso dos mesmos |
| JP6532480B2 (ja) * | 2014-04-15 | 2019-06-19 | ダウ アグロサイエンシィズ エルエルシー | 殺真菌剤としての金属酵素阻害剤化合物 |
| JP6623015B2 (ja) * | 2014-09-29 | 2019-12-18 | 国立研究開発法人理化学研究所 | 植物の耐塩性向上剤 |
| EP3201188A1 (en) | 2014-10-02 | 2017-08-09 | Bayer CropScience Aktiengesellschaft | Novel triazole derivatives useful as fungicides |
| CN104844652A (zh) * | 2015-02-10 | 2015-08-19 | 扬子江药业集团南京海陵药业有限公司 | 艾沙康唑磷酸酯及其制备方法和用途 |
| EP3277674B1 (en) | 2015-04-02 | 2019-09-11 | Bayer CropScience Aktiengesellschaft | Triazol derivatives as fungicides |
| EP3702353B1 (en) | 2015-05-18 | 2023-07-05 | Mycovia Pharmaceuticals, Inc. | Antifungal compositions |
| KR102798709B1 (ko) | 2015-09-18 | 2025-04-23 | 마이코비아 파마슈티컬즈, 인코포레이티드 | 항진균 화합물 제조 방법 |
| TWI636045B (zh) * | 2015-11-17 | 2018-09-21 | 美商維愛美製藥公司 | ４－（（６－（２－（２，４－二氟苯基）－１，１－二氟－２－氧代乙基）吡啶－３－基）氧基）苄腈以及其製造方法 |
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- 2012-06-20 MX MX2013015159A patent/MX2013015159A/es unknown
- 2012-06-20 EA EA201490052A patent/EA201490052A1/ru unknown
- 2012-06-20 EA EA201490088A patent/EA025266B1/ru not_active IP Right Cessation
- 2012-06-20 CN CN201280040552.4A patent/CN103930418A/zh active Pending
- 2012-06-20 CN CN201280040551.XA patent/CN103857675A/zh active Pending
- 2012-06-20 AU AU2012273007A patent/AU2012273007A1/en not_active Abandoned
- 2012-06-20 CN CN201811257707.5A patent/CN109400594A/zh active Pending
- 2012-06-20 US US13/528,283 patent/US8940735B2/en active Active
- 2012-06-20 JP JP2014517113A patent/JP2014523880A/ja active Pending
- 2012-06-20 JP JP2014517112A patent/JP6223329B2/ja not_active Expired - Fee Related
- 2012-06-20 EP EP12801805.8A patent/EP2723730A4/en not_active Withdrawn
- 2012-06-20 KR KR1020147001619A patent/KR20140039059A/ko not_active Withdrawn
- 2012-06-20 KR KR1020147001615A patent/KR101964195B1/ko not_active Expired - Fee Related
- 2012-06-20 US US13/528,319 patent/US8883797B2/en active Active
- 2012-06-20 EP EP12802142.5A patent/EP2723731B1/en not_active Not-in-force
- 2012-06-20 WO PCT/US2012/043295 patent/WO2012177728A1/en not_active Ceased
- 2012-06-20 CA CA2839883A patent/CA2839883A1/en not_active Abandoned
- 2012-06-20 WO PCT/US2012/043292 patent/WO2012177725A1/en not_active Ceased
- 2012-06-20 PH PH1/2013/502622A patent/PH12013502622A1/en unknown
- 2012-06-22 AR ARP120102236A patent/AR094127A1/es not_active Application Discontinuation
- 2012-06-22 UY UY0001034156A patent/UY34156A/es not_active Application Discontinuation
- 2012-06-25 BR BRBR102012015457-9A patent/BR102012015457A2/pt not_active Application Discontinuation
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