JP2014517068A5 - - Google Patents
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- JP2014517068A5 JP2014517068A5 JP2014517090A JP2014517090A JP2014517068A5 JP 2014517068 A5 JP2014517068 A5 JP 2014517068A5 JP 2014517090 A JP2014517090 A JP 2014517090A JP 2014517090 A JP2014517090 A JP 2014517090A JP 2014517068 A5 JP2014517068 A5 JP 2014517068A5
- Authority
- JP
- Japan
- Prior art keywords
- difluoro
- pyridin
- difluorophenyl
- tetrazol
- oxy
- 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 5- (4-Chlorobenzyloxy) pyridin-2-yl Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000001153 fluoro group Chemical group F* 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims 7
- 210000003169 central nervous system Anatomy 0.000 claims 6
- 239000003795 chemical substances by application Substances 0.000 claims 5
- WGOPWWDZOCZQCF-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-methoxypyridin-2-yl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound N1=CC(OC)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1N=NN=C1 WGOPWWDZOCZQCF-UHFFFAOYSA-N 0.000 claims 3
- 102000003964 Histone deacetylase Human genes 0.000 claims 3
- 108090000353 Histone deacetylase Proteins 0.000 claims 3
- 102000008109 Mixed Function Oxygenases Human genes 0.000 claims 3
- 108010074633 Mixed Function Oxygenases Proteins 0.000 claims 3
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims 3
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 3
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 3
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims 3
- 108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 claims 3
- 102000001854 Steroid 17-alpha-Hydroxylase Human genes 0.000 claims 3
- 208000012931 Urologic disease Diseases 0.000 claims 3
- 208000010643 digestive system disease Diseases 0.000 claims 3
- 208000016097 disease of metabolism Diseases 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 208000030159 metabolic disease Diseases 0.000 claims 3
- 208000014001 urinary system disease Diseases 0.000 claims 3
- HVKQLLYGZXYAFP-UHFFFAOYSA-N 1-(5-but-2-ynoxypyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound N1=CC(OCC#CC)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1N=NN=C1 HVKQLLYGZXYAFP-UHFFFAOYSA-N 0.000 claims 2
- YLSNKMKINNBMNS-UHFFFAOYSA-N 1-(5-but-2-ynoxypyridin-2-yl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)propan-2-ol Chemical compound N1=CC(OCC#CC)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1N=NC=N1 YLSNKMKINNBMNS-UHFFFAOYSA-N 0.000 claims 2
- IPXIRBCEJGHIKH-UHFFFAOYSA-N 1-(5-but-2-ynoxypyridin-2-yl)-2-(4-chloro-2-fluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound N1=CC(OCC#CC)=CC=C1C(F)(F)C(O)(C=1C(=CC(Cl)=CC=1)F)CN1N=NN=C1 IPXIRBCEJGHIKH-UHFFFAOYSA-N 0.000 claims 2
- CGMVNUZEPNKFRO-UHFFFAOYSA-N 1-(5-but-2-ynoxypyridin-2-yl)-2-(4-chloro-2-fluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)propan-2-ol Chemical compound N1=CC(OCC#CC)=CC=C1C(F)(F)C(O)(C=1C(=CC(Cl)=CC=1)F)CN1N=NC=N1 CGMVNUZEPNKFRO-UHFFFAOYSA-N 0.000 claims 2
- SYFXBIITKXDKRV-UHFFFAOYSA-N 1-[5-(3,4-difluorophenoxy)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(OC=2C=C(F)C(F)=CC=2)=CC=1)(O)CN1C=NN=N1 SYFXBIITKXDKRV-UHFFFAOYSA-N 0.000 claims 2
- JNLWLLFEHXOJGU-UHFFFAOYSA-N 1-[5-(5-bromopyridin-2-yl)oxypyridin-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(OC=2N=CC(Br)=CC=2)=CC=1)(O)CN1C=NN=N1 JNLWLLFEHXOJGU-UHFFFAOYSA-N 0.000 claims 2
- YEKSYZQYUGXLMI-UHFFFAOYSA-N 1-[5-(5-bromopyrimidin-2-yl)oxypyridin-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(OC=2N=CC(Br)=CN=2)=CC=1)(O)CN1C=NN=N1 YEKSYZQYUGXLMI-UHFFFAOYSA-N 0.000 claims 2
- SYAXVNSNJHBVSD-UHFFFAOYSA-N 1-[5-(5-chloropyridin-2-yl)oxypyridin-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(OC=2N=CC(Cl)=CC=2)=CC=1)(O)CN1C=NN=N1 SYAXVNSNJHBVSD-UHFFFAOYSA-N 0.000 claims 2
- SBCWXJIXBSJCBQ-UHFFFAOYSA-N 1-[5-(5-chloropyrimidin-2-yl)oxypyridin-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(OC=2N=CC(Cl)=CN=2)=CC=1)(O)CN1C=NN=N1 SBCWXJIXBSJCBQ-UHFFFAOYSA-N 0.000 claims 2
- JCGZSXIZHBLWTE-UHFFFAOYSA-N 1-[5-(cyclopropylmethoxy)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(OCC2CC2)=CC=1)(O)CN1C=NN=N1 JCGZSXIZHBLWTE-UHFFFAOYSA-N 0.000 claims 2
- PKCDOOARHLDSAE-UHFFFAOYSA-N 1-[5-(cyclopropylmethoxy)pyridin-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=CC(OCC2CC2)=CC=1)(O)CN1N=CN=N1 PKCDOOARHLDSAE-UHFFFAOYSA-N 0.000 claims 2
- QDTUBQRGESUYJO-UHFFFAOYSA-N 1-[5-[(2-chloropyridin-4-yl)methoxy]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(OCC=2C=C(Cl)N=CC=2)=CC=1)(O)CN1C=NN=N1 QDTUBQRGESUYJO-UHFFFAOYSA-N 0.000 claims 2
- XEZVPAIENTVAEO-UHFFFAOYSA-N 1-[5-[(4-chloro-3-fluorophenyl)methoxy]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(OCC=2C=C(F)C(Cl)=CC=2)=CC=1)(O)CN1C=NN=N1 XEZVPAIENTVAEO-UHFFFAOYSA-N 0.000 claims 2
- HLUHTLIKEKHNPM-UHFFFAOYSA-N 1-[5-[(5-chloropyridin-2-yl)methoxy]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(OCC=2N=CC(Cl)=CC=2)=CC=1)(O)CN1C=NN=N1 HLUHTLIKEKHNPM-UHFFFAOYSA-N 0.000 claims 2
- PTURHPXIHPVGSH-UHFFFAOYSA-N 1-[5-[(6-chloro-1,3-benzothiazol-2-yl)oxy]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(OC=2SC3=CC(Cl)=CC=C3N=2)=CC=1)(O)CN1C=NN=N1 PTURHPXIHPVGSH-UHFFFAOYSA-N 0.000 claims 2
- YFHGZEGAWPBYHO-UHFFFAOYSA-N 1-[5-[(6-chloropyridin-3-yl)methoxy]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(OCC=2C=NC(Cl)=CC=2)=CC=1)(O)CN1C=NN=N1 YFHGZEGAWPBYHO-UHFFFAOYSA-N 0.000 claims 2
- PQAAXINOJICDPB-UHFFFAOYSA-N 1-[5-[2-(4-chlorophenyl)-2,2-difluoroethoxy]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(OCC(F)(F)C=2C=CC(Cl)=CC=2)=CC=1)(O)CN1C=NN=N1 PQAAXINOJICDPB-UHFFFAOYSA-N 0.000 claims 2
- RCWOURKKFYTYDE-UHFFFAOYSA-N 1-[5-[2-[4-(difluoromethoxy)phenyl]-2,2-difluoroethoxy]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(OCC(F)(F)C=2C=CC(OC(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 RCWOURKKFYTYDE-UHFFFAOYSA-N 0.000 claims 2
- IFRLZRMEXDTZIH-UHFFFAOYSA-N 1-[5-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxypyridin-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(OC=2C(=CC(=CN=2)C(F)(F)F)Cl)=CC=1)(O)CN1C=NN=N1 IFRLZRMEXDTZIH-UHFFFAOYSA-N 0.000 claims 2
- DAALOWCHAWFYGE-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-phenoxypyridin-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(OC=2C=CC=CC=2)=CC=1)(O)CN1C=NN=N1 DAALOWCHAWFYGE-UHFFFAOYSA-N 0.000 claims 2
- AIJHNWXKGOESHI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-propan-2-yloxypyridin-2-yl)-3-(tetrazol-1-yl)propan-2-ol Chemical compound N1=CC(OC(C)C)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1N=NN=C1 AIJHNWXKGOESHI-UHFFFAOYSA-N 0.000 claims 2
- NYPFLMYZCVCAKR-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-(2-methylpropoxy)pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound N1=CC(OCC(C)C)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1N=NN=C1 NYPFLMYZCVCAKR-UHFFFAOYSA-N 0.000 claims 2
- XPANKAHUQGPSAY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[(2-fluorophenyl)methoxy]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(OCC=2C(=CC=CC=2)F)=CC=1)(O)CN1C=NN=N1 XPANKAHUQGPSAY-UHFFFAOYSA-N 0.000 claims 2
- PDWIBOREHQRJKY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[(3-methoxyphenyl)methoxy]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound COC1=CC=CC(COC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 PDWIBOREHQRJKY-UHFFFAOYSA-N 0.000 claims 2
- OBJSQXGYJBAOCW-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[(4-fluorophenyl)methoxy]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(OCC=2C=CC(F)=CC=2)=CC=1)(O)CN1C=NN=N1 OBJSQXGYJBAOCW-UHFFFAOYSA-N 0.000 claims 2
- YDGQWNDMYPHJPJ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[(4-methoxyphenyl)methoxy]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 YDGQWNDMYPHJPJ-UHFFFAOYSA-N 0.000 claims 2
- UXZYXIXZCFWFIZ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]oxypyridin-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(OC=2C(=CC(=CN=2)C(F)(F)F)F)=CC=1)(O)CN1C=NN=N1 UXZYXIXZCFWFIZ-UHFFFAOYSA-N 0.000 claims 2
- IOMQXEOYTOCEON-WXMAUWIXSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[5-[(e)-methoxyiminomethyl]pyridin-2-yl]oxypyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound N1=CC(/C=N/OC)=CC=C1OC1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 IOMQXEOYTOCEON-WXMAUWIXSA-N 0.000 claims 2
- VGUGPMASHJEVIT-QQMJPZKZSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[5-[(e)-phenylmethoxyiminomethyl]pyridin-2-yl]oxypyridin-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(OC=2N=CC(\C=N\OCC=3C=CC=CC=3)=CC=2)=CC=1)(O)CN1C=NN=N1 VGUGPMASHJEVIT-QQMJPZKZSA-N 0.000 claims 2
- NMKPJXNOLSEPLP-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[[2-fluoro-4-(trifluoromethyl)phenyl]methoxy]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(OCC=2C(=CC(=CC=2)C(F)(F)F)F)=CC=1)(O)CN1C=NN=N1 NMKPJXNOLSEPLP-UHFFFAOYSA-N 0.000 claims 2
- NONREPZTKMOQNT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-(1,1,1-trifluoropropan-2-yloxy)pyridin-2-yl]propan-2-ol Chemical compound N1=CC(OC(C)C(F)(F)F)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1N=NN=C1 NONREPZTKMOQNT-UHFFFAOYSA-N 0.000 claims 2
- PNUGCHCVDNISAD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 PNUGCHCVDNISAD-UHFFFAOYSA-N 0.000 claims 2
- SJUQXQOYIXPPHM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=CC(OC(F)(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 SJUQXQOYIXPPHM-UHFFFAOYSA-N 0.000 claims 2
- LXDLGDAFDSOHDC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethyl)phenoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=CC(=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 LXDLGDAFDSOHDC-UHFFFAOYSA-N 0.000 claims 2
- UPAKKJPOEMHFHM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[5-(trifluoromethyl)pyridin-2-yl]oxypyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2N=CC(=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 UPAKKJPOEMHFHM-UHFFFAOYSA-N 0.000 claims 2
- IQTKREWDKXVIIS-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[5-(trifluoromethyl)pyrimidin-2-yl]oxypyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2N=CC(=CN=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 IQTKREWDKXVIIS-UHFFFAOYSA-N 0.000 claims 2
- YNNIGIOZDBNBSO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[6-(trifluoromethyl)pyridin-3-yl]oxypyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=NC(=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 YNNIGIOZDBNBSO-UHFFFAOYSA-N 0.000 claims 2
- QVIFXEMDBVPUIW-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[[3-(2,2,2-trifluoroethoxy)phenyl]methoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=C(OCC(F)(F)F)C=CC=2)=CC=1)(O)CN1C=NN=N1 QVIFXEMDBVPUIW-UHFFFAOYSA-N 0.000 claims 2
- KFUPCLVIUKWJQC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[[3-(trifluoromethyl)phenyl]methoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=C(C=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 KFUPCLVIUKWJQC-UHFFFAOYSA-N 0.000 claims 2
- KZKOHLAKKPMDEE-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[[4-(2,2,2-trifluoroethoxy)phenyl]methoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=CC(OCC(F)(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 KZKOHLAKKPMDEE-UHFFFAOYSA-N 0.000 claims 2
- ZRLMHPDKWKNAHT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[[4-(trifluoromethoxy)phenyl]methoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=CC(OC(F)(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 ZRLMHPDKWKNAHT-UHFFFAOYSA-N 0.000 claims 2
- JMIAGKZEYWZUOX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[[4-(trifluoromethyl)phenyl]methoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=CC(=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 JMIAGKZEYWZUOX-UHFFFAOYSA-N 0.000 claims 2
- UFKVJDPTOJMFBI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[[5-(trifluoromethyl)pyridin-2-yl]methoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2N=CC(=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 UFKVJDPTOJMFBI-UHFFFAOYSA-N 0.000 claims 2
- OPLZQRRMHRRZTI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=NC(=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 OPLZQRRMHRRZTI-UHFFFAOYSA-N 0.000 claims 2
- FSEBXYXBDZYVLT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)-1-[5-(1,1,1-trifluoropropan-2-yloxy)pyridin-2-yl]propan-2-ol Chemical compound N1=CC(OC(C)C(F)(F)F)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1N=NC=N1 FSEBXYXBDZYVLT-UHFFFAOYSA-N 0.000 claims 2
- GJDCVKSVFZERGF-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-(2,2-difluoro-2-phenylethoxy)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(OCC(F)(F)C=2C=CC=CC=2)=CC=1)(O)CN1C=NN=N1 GJDCVKSVFZERGF-UHFFFAOYSA-N 0.000 claims 2
- URMNQRYQGRABFQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[(2,3-difluorophenyl)methoxy]pyridin-2-yl]-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=CC(OCC=2C(=C(F)C=CC=2)F)=CC=1)(O)CN1C=NC=N1 URMNQRYQGRABFQ-UHFFFAOYSA-N 0.000 claims 2
- QZZWOYRWEPDODB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[(2,3-difluorophenyl)methoxy]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(OCC=2C(=C(F)C=CC=2)F)=CC=1)(O)CN1C=NN=N1 QZZWOYRWEPDODB-UHFFFAOYSA-N 0.000 claims 2
- LQWHNJKOZOROGI-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[(2,3-difluorophenyl)methoxy]pyridin-2-yl]-1,1-difluoro-3-(triazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C(=C(F)C=CC=2)F)=CC=1)(O)CN1C=CN=N1 LQWHNJKOZOROGI-UHFFFAOYSA-N 0.000 claims 2
- QZDFJMZRVIVPFV-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[(2,4-difluorophenyl)methoxy]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(OCC=2C(=CC(F)=CC=2)F)=CC=1)(O)CN1C=NN=N1 QZDFJMZRVIVPFV-UHFFFAOYSA-N 0.000 claims 2
- XUUVUNXADIIZSC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[(3,4-difluorophenyl)methoxy]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(OCC=2C=C(F)C(F)=CC=2)=CC=1)(O)CN1C=NN=N1 XUUVUNXADIIZSC-UHFFFAOYSA-N 0.000 claims 2
- HXBJIWUXNPSBKE-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[(3,5-difluorophenyl)methoxy]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(OCC=2C=C(F)C=C(F)C=2)=CC=1)(O)CN1C=NN=N1 HXBJIWUXNPSBKE-UHFFFAOYSA-N 0.000 claims 2
- YQVYCTZXZWSPKO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[(3,5-difluorophenyl)methoxy]pyridin-2-yl]-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=CC(OCC=2C=C(F)C=C(F)C=2)=CC=1)(O)CN1N=CN=N1 YQVYCTZXZWSPKO-UHFFFAOYSA-N 0.000 claims 2
- CIZNHNZLOPHVRA-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[(3,5-difluoropyridin-2-yl)methoxy]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(OCC=2C(=CC(F)=CN=2)F)=CC=1)(O)CN1C=NN=N1 CIZNHNZLOPHVRA-UHFFFAOYSA-N 0.000 claims 2
- VLVXXNICTPQDNV-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 VLVXXNICTPQDNV-UHFFFAOYSA-N 0.000 claims 2
- VLZZIODMLKZVBN-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1,1-difluoro-3-(tetrazol-2-yl)-1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC(F)(F)F)=CC=1)(O)CN1N=CN=N1 VLZZIODMLKZVBN-UHFFFAOYSA-N 0.000 claims 2
- QVASALRIIVOUKU-UHFFFAOYSA-N 2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxy-1,3-thiazole-5-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2SC(=CN=2)C#N)=CC=1)(O)CN1C=NN=N1 QVASALRIIVOUKU-UHFFFAOYSA-N 0.000 claims 2
- XSUTYOOTQMHGSG-UHFFFAOYSA-N 2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxyacetonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC#N)=CC=1)(O)CN1C=NN=N1 XSUTYOOTQMHGSG-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- SGXZOQMCSGRFTI-UHFFFAOYSA-N 3-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxybenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=C(C=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 SGXZOQMCSGRFTI-UHFFFAOYSA-N 0.000 claims 2
- JTMLXDYGXRSKSK-UHFFFAOYSA-N 3-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]-2-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C(=C(C#N)C=CC=2)F)=CC=1)(O)CN1C=NN=N1 JTMLXDYGXRSKSK-UHFFFAOYSA-N 0.000 claims 2
- JJBOEUZKIRIOPW-UHFFFAOYSA-N 3-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]-4-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C(=CC=C(C=2)C#N)F)=CC=1)(O)CN1C=NN=N1 JJBOEUZKIRIOPW-UHFFFAOYSA-N 0.000 claims 2
- NTQMVHXXBDLZFB-UHFFFAOYSA-N 3-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=C(C=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 NTQMVHXXBDLZFB-UHFFFAOYSA-N 0.000 claims 2
- SSVFQLLQMBIASM-UHFFFAOYSA-N 3-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxymethyl]-2-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C(=C(C#N)C=CC=2)F)=CC=1)(O)CN1N=CN=N1 SSVFQLLQMBIASM-UHFFFAOYSA-N 0.000 claims 2
- CUIBVRMLHZQLOD-UHFFFAOYSA-N 3-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxymethyl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=C(C=CC=2)C#N)=CC=1)(O)CN1N=CN=N1 CUIBVRMLHZQLOD-UHFFFAOYSA-N 0.000 claims 2
- FZHFYFOUCRHBSP-UHFFFAOYSA-N 4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxy-1,1-difluoroethyl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC(F)(F)C=2C=CC(=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 FZHFYFOUCRHBSP-UHFFFAOYSA-N 0.000 claims 2
- UBLQFIUAVRCSRG-UHFFFAOYSA-N 4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxy-2-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=C(F)C(C#N)=CC=2)=CC=1)(O)CN1C=NN=N1 UBLQFIUAVRCSRG-UHFFFAOYSA-N 0.000 claims 2
- SFKSXZPSUOGBJG-UHFFFAOYSA-N 4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxy-3-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C(=CC(=CC=2)C#N)F)=CC=1)(O)CN1C=NN=N1 SFKSXZPSUOGBJG-UHFFFAOYSA-N 0.000 claims 2
- VGKVPQNXIHRCGV-UHFFFAOYSA-N 4-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxy-3-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C(=CC(=CC=2)C#N)F)=CC=1)(O)CN1N=CN=N1 VGKVPQNXIHRCGV-UHFFFAOYSA-N 0.000 claims 2
- WVUQNAOQBXFCBU-UHFFFAOYSA-N 4-[6-[2-(4-chloro-2-fluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxy-2-fluorobenzonitrile Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=C(F)C(C#N)=CC=2)=CC=1)(O)CN1C=NN=N1 WVUQNAOQBXFCBU-UHFFFAOYSA-N 0.000 claims 2
- SOSNFFNFYUNQBK-UHFFFAOYSA-N 4-[6-[2-(4-chloro-2-fluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxybenzonitrile Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=CC(=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 SOSNFFNFYUNQBK-UHFFFAOYSA-N 0.000 claims 2
- QCUUBBSDSASBNW-UHFFFAOYSA-N 4-[6-[2-(4-chloro-2-fluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxy-2-fluorobenzonitrile Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=C(F)C(C#N)=CC=2)=CC=1)(O)CN1N=CN=N1 QCUUBBSDSASBNW-UHFFFAOYSA-N 0.000 claims 2
- RZSGJQGEJHFXBA-UHFFFAOYSA-N 4-[6-[2-(4-chloro-2-fluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxybenzonitrile Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=CC(=CC=2)C#N)=CC=1)(O)CN1N=CN=N1 RZSGJQGEJHFXBA-UHFFFAOYSA-N 0.000 claims 2
- BHRWSDDBHYTHBI-UHFFFAOYSA-N 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]-2-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=C(F)C(C#N)=CC=2)=CC=1)(O)CN1C=NN=N1 BHRWSDDBHYTHBI-UHFFFAOYSA-N 0.000 claims 2
- FVHPJHBARYSHPM-UHFFFAOYSA-N 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]-3-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C(=CC(=CC=2)C#N)F)=CC=1)(O)CN1C=NN=N1 FVHPJHBARYSHPM-UHFFFAOYSA-N 0.000 claims 2
- WPIYQBNGDLNDCH-UHFFFAOYSA-N 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=CC(=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 WPIYQBNGDLNDCH-UHFFFAOYSA-N 0.000 claims 2
- XYVJOGXIQLAGKF-UHFFFAOYSA-N 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxymethyl]-3-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C(=CC(=CC=2)C#N)F)=CC=1)(O)CN1N=CN=N1 XYVJOGXIQLAGKF-UHFFFAOYSA-N 0.000 claims 2
- RLKWFAYSFXRFLI-UHFFFAOYSA-N 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxymethyl]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=CC(=CC=2)C#N)=CC=1)(O)CN1N=CN=N1 RLKWFAYSFXRFLI-UHFFFAOYSA-N 0.000 claims 2
- PDWKGSXTQFBGAN-UHFFFAOYSA-N 4-[[6-[2-(4-chloro-2-fluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]benzonitrile Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=CC(=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 PDWKGSXTQFBGAN-UHFFFAOYSA-N 0.000 claims 2
- GDZVRIPZSVANER-UHFFFAOYSA-N 4-[[6-[2-(4-chloro-2-fluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxymethyl]benzonitrile Chemical compound C=1C=C(Cl)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=CC(=CC=2)C#N)=CC=1)(O)CN1N=CN=N1 GDZVRIPZSVANER-UHFFFAOYSA-N 0.000 claims 2
- QKKCVRMGPINFFZ-UHFFFAOYSA-N 5-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxypyrimidine-2-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OC=2C=NC(=NC=2)C#N)=CC=1)(O)CN1C=NN=N1 QKKCVRMGPINFFZ-UHFFFAOYSA-N 0.000 claims 2
- SGJVPHOPWRXUPH-UHFFFAOYSA-N 5-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]-2-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=C(C(F)=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 SGJVPHOPWRXUPH-UHFFFAOYSA-N 0.000 claims 2
- JCBSYUSINWLFLJ-UHFFFAOYSA-N 5-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]oxymethyl]thiophene-2-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2SC(=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 JCBSYUSINWLFLJ-UHFFFAOYSA-N 0.000 claims 2
- ZRUGZSDNLVHZES-UHFFFAOYSA-N 5-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-2-yl)propyl]pyridin-3-yl]oxymethyl]-2-fluorobenzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(OCC=2C=C(C(F)=CC=2)C#N)=CC=1)(O)CN1N=CN=N1 ZRUGZSDNLVHZES-UHFFFAOYSA-N 0.000 claims 2
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Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103764646A (zh) * | 2011-06-19 | 2014-04-30 | 威尔金制药有限公司 | 金属酶抑制剂化合物 |
| EP2721023B1 (en) * | 2011-06-19 | 2018-08-08 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
| EA025266B1 (ru) | 2011-06-23 | 2016-12-30 | Ваймет Фармасьютикалс, Инк. | Соединения, ингибирующие металлоферменты |
| US10221160B2 (en) | 2012-01-20 | 2019-03-05 | Mycovia Pharmaceuticals, Inc. | Metalloenzyme inhibitor compounds |
| AU2014209107B2 (en) | 2013-01-28 | 2018-04-12 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
| EP2984081B1 (en) * | 2013-04-12 | 2017-08-09 | Bayer CropScience Aktiengesellschaft | Novel triazole derivatives |
| EP2984080B1 (en) | 2013-04-12 | 2017-08-30 | Bayer CropScience Aktiengesellschaft | Novel triazolinthione derivatives |
| US9668481B2 (en) * | 2013-04-12 | 2017-06-06 | Bayer Cropscience Aktiengesellschaft | Triazole derivatives |
| CA2913914C (en) * | 2013-05-28 | 2018-03-20 | Viamet Pharmaceuticals, Inc. | Fungicidal compositions |
| EA201690007A1 (ru) * | 2013-06-12 | 2016-04-29 | Ваймет Фармасьютикалс, Инк. | Соединения, ингибирующие металлоферменты |
| WO2015027863A1 (zh) * | 2013-08-27 | 2015-03-05 | 中国中化股份有限公司 | 含取代苄氧基的醚类化合物作为制备抗肿瘤药物的应用 |
| CA2942932A1 (en) * | 2014-03-19 | 2015-09-24 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| US10399943B2 (en) | 2014-03-19 | 2019-09-03 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| US10196375B2 (en) | 2014-03-19 | 2019-02-05 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| EP3119755B1 (en) | 2014-03-19 | 2019-03-06 | Viamet Pharmaceuticals (NC), Inc. | Antifungal compound process |
| CN106103424A (zh) * | 2014-03-19 | 2016-11-09 | 维亚梅特制药公司 | 2‑(2,4‑二氟苯基)‑1,1‑二氟‑1‑(5‑经取代的吡啶‑2‑基)‑3‑(1h‑四唑‑1‑基)丙烷‑2‑醇和其制备方法 |
| US9802914B2 (en) | 2014-03-19 | 2017-10-31 | Viamet Pharmaceuticals, Inc. | Antifungal compound process |
| MX2016012060A (es) * | 2014-03-19 | 2017-01-19 | Viamet Pharmaceuticals Inc | 2-(2,4-difluorofenil)-1,1-difluoro-1-(5-sustituido-piridin-2-il)- 3-(1h-tetrazol-1-il)propan-2-oles y procesos para su preparacion. |
| ES2800905T3 (es) | 2014-03-19 | 2021-01-05 | Mycovia Pharmaceuticals Inc | Procedimiento para compuesto antifúngico |
| US10017494B2 (en) | 2014-03-19 | 2018-07-10 | Mycovia Pharmaceuticals, Inc. | Antifungal compound process |
| ES2815373T3 (es) * | 2014-03-19 | 2021-03-29 | Mycovia Pharmaceuticals Inc | Procedimiento de compuesto antifúngico |
| 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 |
| JP2017531636A (ja) | 2014-10-02 | 2017-10-26 | 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 | 殺菌剤として有用な新規トリアゾール誘導体 |
| WO2016156294A1 (en) | 2015-04-02 | 2016-10-06 | Bayer Cropscience Aktiengesellschaft | Triazol derivatives as fungicides |
| UA120784C2 (uk) * | 2015-05-18 | 2020-02-10 | Ваймет Фармасьютікалс (Нк), Інк. | Протигрибкові сполуки |
| EA037521B1 (ru) | 2015-09-18 | 2021-04-07 | ВиПиЭс-3, ИНК. | Противогрибковые соединения и способы их получения |
| US10414735B2 (en) | 2015-11-09 | 2019-09-17 | Forge Therapeutics, Inc. | Substituted hydroxypyrimidinones for treating bacterial infections |
| US10611747B2 (en) | 2015-11-09 | 2020-04-07 | Forge Therapeutics, Inc. | Pyrone based compounds for treating bacterial infections |
| CN108473443A (zh) * | 2015-11-17 | 2018-08-31 | 美国陶氏益农公司 | 4-((6-(2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1h-1,2,4-三唑-1-基)丙基)吡啶-3-基)氧基)苄腈以及制备方法 |
| CN108882709A (zh) * | 2015-11-17 | 2018-11-23 | 美国陶氏益农公司 | 4-((6-(2-(2,4-二氟苯基)-1,1-二氟-2-氧代乙基)吡啶-3-基)氧基)苄腈以及制备方法 |
| US20180354928A1 (en) * | 2015-11-17 | 2018-12-13 | Dow Agrosciences Llc | 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation |
| KR20180100114A (ko) * | 2015-11-17 | 2018-09-07 | 다우 아그로사이언시즈 엘엘씨 | 4-((6-(2-(2,4-디플루오로페닐)-1,1-디플루오로-2-히드록시-3-(1h-1,2,4-트리아졸-1-일)프로필)피리딘-3-일)옥시)벤조니트릴 및 제조방법 |
| AU2017317988B2 (en) | 2016-08-31 | 2020-12-24 | Jiangsu Hengrui Medicine Co., Ltd. | Oxopicolinamide derivative, preparation method therefor and pharmaceutical use thereof |
| JP2018048090A (ja) * | 2016-09-21 | 2018-03-29 | 大阪ガスケミカル株式会社 | 工業用保存剤 |
| WO2018094147A1 (en) * | 2016-11-18 | 2018-05-24 | Vps-3, Inc. | 4-((6-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation |
| US10787431B2 (en) | 2016-11-18 | 2020-09-29 | Dow Agrosciences Llc | 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation |
| US20190284158A1 (en) * | 2016-11-18 | 2019-09-19 | Dow Agrosciences Llc | 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-mercapto-1h-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile and processes of preparation |
| EP3541798A4 (en) * | 2016-11-18 | 2020-04-29 | Dow AgroSciences LLC | 4 - ((6- (2- (2,4-DIFLUORPHENYL) -1,1-DIFLUOR-2-HYDROXY-3- (5-MERCAPTO-1H-1,2,4-TRIAZOL-1-YL) PROPYL) PYRIDIN-3-YL) OXY) BENZONITRILE AND METHOD FOR PRODUCING THE SAME |
| CN110291078A (zh) * | 2016-11-18 | 2019-09-27 | 美国陶氏益农公司 | 4-((6-(2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-巯基-1h-1,2,4-三唑-1-基)丙基)吡啶-3-基)氧基)苄腈及制备方法 |
| EP3541800A4 (en) * | 2016-11-18 | 2020-04-08 | Dow Agrosciences Llc | PROCESSES FOR THE PREPARATION OF 4 - ((6- (2,4-DIFLUOROPHENYL) -1,1-DIFLUORO-2-HYDROXY-3- (5-MERCAPTO-1H-1,2,4-TRIAZOL-1-YL) PROPYL ) PYRIDIN-3-YL) OXY) BENZONITRILE |
| BR112019009767A2 (pt) * | 2016-11-18 | 2019-08-13 | Dow Agrosciences Llc | 4-((6-(2,4-difluorofenil)-1,1-difluoro-2-hidróxi-3(5-mercapto-1h-1,2,4-triazol-1-il)propil)piridin-3-il)óxi)benzonitrila e processos de preparação |
| EP3541801A4 (en) * | 2016-11-18 | 2020-04-29 | Dow AgroSciences LLC | 4- (6- (2- (2,4-DIFLUORPHENYL) -1,1-DIFLUOR-2-HYDROXY-3- (5-MERCAPTO-1H |
| US20190297890A1 (en) * | 2016-11-22 | 2019-10-03 | Dow Agrosciences Llc | Fungicidal compounds and mixtures for fungal control in cereals |
| BR112019010138A2 (pt) * | 2016-11-22 | 2019-08-20 | Dow Agrosciences Llc | compostos fungicidas e misturas para controle de fungos em cereais |
| EP3544429A4 (en) * | 2016-11-22 | 2020-04-29 | Dow Agrosciences Llc | USE OF A DIFLUORO- (2-HYDROXYPROPYL) PYRIDINE COMPOUND AS A FUNGICIDE FOR THE CONTROL OF WHEAT PHYTOPATHOGENIC FUNGI |
| EP3544430A4 (en) * | 2016-11-22 | 2020-04-29 | Dow Agrosciences Llc | USE OF A DIFLUOR- (2-HYDROXYPROPYL) PYRIDINE COMPOUND AS A FUNGICIDE FOR CONTROLLING PHYTOPATHOGENIC MUSHROOMS OF CORN |
| RU2019118632A (ru) * | 2016-11-22 | 2020-12-24 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Фунгицидные композиции и смеси для борьбы с грибковыми заболеваниями зерновых культур |
| AR110207A1 (es) * | 2016-11-22 | 2019-03-06 | Viamet Pharmaceuticals Inc | Compuestos y mezclas fungicidas para el control de hongos en cereales |
| CA3044389A1 (en) * | 2016-11-22 | 2018-05-31 | Dow Agrosciences Llc | Use of a difluoro-(2-hydroxypropyl)pyridine compound as a fungicide for control of phytopathogenic fungi of barley |
| MA46076B1 (fr) * | 2016-11-22 | 2022-01-31 | Dow Agrosciences Llc | Composés fongicides et mélanges de régulation des champignons dans les céréales |
| AR110210A1 (es) * | 2016-11-22 | 2019-03-06 | Viamet Pharmaceuticals Inc | Uso de un compuesto de difluoro-(2-hidroxipropil)piridina como fungicida para el control de la mancha foliar en remolacha azucarera |
| BR112019010038A2 (pt) * | 2016-11-22 | 2019-09-03 | Dow Agrosciences Llc | uso de um composto de difluoro-(2-hidroxipropildpiridina como fungicida para controle de fungos fitopatogênicos do arroz |
| CN114989205A (zh) | 2016-12-22 | 2022-09-02 | 卡里塞拉生物科学股份公司 | 用于抑制精氨酸酶活性的组合物和方法 |
| US11021471B2 (en) | 2017-05-10 | 2021-06-01 | Forge Therapeutics, Inc. | Antibacterial compounds |
| EP3710432A1 (en) | 2017-11-13 | 2020-09-23 | Bayer Aktiengesellschaft | Tetrazolylpropyl derivatives and their use as fungicides |
| AU2019345150A1 (en) | 2018-09-20 | 2021-05-13 | Blacksmith Medicines, Inc. | Antibacterial compounds |
| WO2021195260A1 (en) | 2020-03-25 | 2021-09-30 | Forge Therapeutics, Inc. | Lpxc inhibitor and methods of making |
| TW202144340A (zh) | 2020-04-03 | 2021-12-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 稠合咪唑類衍生物、其製備方法及其在醫藥上的應用 |
| CN113278409B (zh) * | 2021-06-22 | 2022-04-29 | 西南石油大学 | 一种高温酸化缓蚀剂 |
| JP2024536864A (ja) | 2021-09-28 | 2024-10-08 | ブラックスミス メディシンズ，インク． | Ｌｐｘｃ阻害剤およびその使用 |
| CN117069693A (zh) * | 2022-05-16 | 2023-11-17 | 上海济煜医药科技有限公司 | 一类含胺基结构化合物的制备方法及作为抗菌剂的应用 |
| WO2024068656A1 (en) | 2022-09-28 | 2024-04-04 | Syngenta Crop Protection Ag | Fungicidal compositions |
| AR130567A1 (es) | 2022-09-28 | 2024-12-18 | Syngenta Crop Protection Ag | Composiciones fungicidas |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8304282D0 (en) * | 1983-02-16 | 1983-03-23 | Pfizer Ltd | Antifungal agents |
| US4921475A (en) | 1983-08-18 | 1990-05-01 | Drug Delivery Systems Inc. | Transdermal drug patch with microtubes |
| US5087240A (en) | 1983-08-18 | 1992-02-11 | Drug Delivery Systems Inc. | Transdermal drug patch with conductive fibers |
| EP0149426B1 (de) * | 1983-12-20 | 1988-05-04 | Ciba-Geigy Ag | Mikrobizide |
| US4738851A (en) | 1985-09-27 | 1988-04-19 | University Of Iowa Research Foundation, Inc. | Controlled release ophthalmic gel formulation |
| US5163899A (en) | 1987-03-20 | 1992-11-17 | Drug Delivery Systems Inc. | Transdermal drug delivery system |
| US5312325A (en) | 1987-05-28 | 1994-05-17 | Drug Delivery Systems Inc | Pulsating transdermal drug delivery system |
| GB8804164D0 (en) | 1988-02-23 | 1988-03-23 | Tucker J M | Bandage for administering physiologically active compound |
| US4882150A (en) | 1988-06-03 | 1989-11-21 | Kaufman Herbert E | Drug delivery system |
| GB8819308D0 (en) * | 1988-08-13 | 1988-09-14 | Pfizer Ltd | Triazole antifungal agents |
| US5008110A (en) | 1988-11-10 | 1991-04-16 | The Procter & Gamble Company | Storage-stable transdermal patch |
| US5088977A (en) | 1988-12-21 | 1992-02-18 | Drug Delivery Systems Inc. | Electrical transdermal drug applicator with counteractor and method of drug delivery |
| US5521222A (en) | 1989-09-28 | 1996-05-28 | Alcon Laboratories, Inc. | Topical ophthalmic pharmaceutical vehicles |
| PT96059B (pt) | 1989-12-04 | 1998-07-31 | Searle & Co | Sistema de camada unica para a administracao de um medicamento por via transdermica |
| US5077033A (en) | 1990-08-07 | 1991-12-31 | Mediventures Inc. | Ophthalmic drug delivery with thermo-irreversible gels of polxoxyalkylene polymer and ionic polysaccharide |
| DK0495421T3 (da) | 1991-01-15 | 1996-12-09 | Alcon Lab Inc | Anvendelse af carragenaner i topiske ophthalmiske sammensætninger |
| GB9121456D0 (en) | 1991-10-10 | 1991-11-27 | Pfizer Ltd | Triazole antifungal agents |
| US5352456A (en) | 1991-10-10 | 1994-10-04 | Cygnus Therapeutic Systems | Device for administering drug transdermally which provides an initial pulse of drug |
| CA2123809A1 (en) | 1991-12-18 | 1993-06-24 | Debra L. Wilfong | Multilayered barrier structures |
| EP0553769B1 (de) | 1992-01-29 | 1996-01-03 | FRANZ VÖLKL GmbH & CO. SKI UND TENNIS SPORTARTIKELFABRIK KG | Ballspielschläger, insbesondere Tennisschläger |
| IL114193A (en) | 1994-06-20 | 2000-02-29 | Teva Pharma | Ophthalmic pharmaceutical compositions based on sodium alginate |
| ES2094688B1 (es) | 1994-08-08 | 1997-08-01 | Cusi Lab | Manoemulsion del tipo de aceite en agua, util como vehiculo oftalmico y procedimiento para su preparacion. |
| IT1283911B1 (it) | 1996-02-05 | 1998-05-07 | Farmigea Spa | Soluzioni oftalmiche viscosizzate con polisaccaridi della gomma di tamarindo |
| US5800807A (en) | 1997-01-29 | 1998-09-01 | Bausch & Lomb Incorporated | Ophthalmic compositions including glycerin and propylene glycol |
| US6261547B1 (en) | 1998-04-07 | 2001-07-17 | Alcon Manufacturing, Ltd. | Gelling ophthalmic compositions containing xanthan gum |
| US6197934B1 (en) | 1998-05-22 | 2001-03-06 | Collagenesis, Inc. | Compound delivery using rapidly dissolving collagen film |
| CA2669887A1 (en) * | 2006-11-21 | 2008-05-29 | Viamet Pharmaceuticals, Inc. | Metallo-oxidoreductase inhibitors using metal binding moieties in combination with targeting moieties |
| WO2008124131A1 (en) * | 2007-04-05 | 2008-10-16 | The John Hopkins University | Antifungal agents as neuroprotectants |
| CA2837400C (en) * | 2010-04-24 | 2017-12-12 | Viamet Pharmaceuticals, Inc. | 5-(optionally substituted phenyl) pyridin-2-yl compounds as metalloenzyme inhibitors |
| EP2721023B1 (en) * | 2011-06-19 | 2018-08-08 | Viamet Pharmaceuticals (NC), Inc. | Metalloenzyme inhibitor compounds |
| CN103764646A (zh) * | 2011-06-19 | 2014-04-30 | 威尔金制药有限公司 | 金属酶抑制剂化合物 |
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- 2013-12-18 CL CL2013003638A patent/CL2013003638A1/es unknown
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2014
- 2014-01-10 ZA ZA2014/00232A patent/ZA201400232B/en unknown
- 2014-01-15 CO CO14007084A patent/CO6930356A2/es unknown
- 2014-01-16 EC ECSP14013152 patent/ECSP14013152A/es unknown
- 2014-01-16 CR CR20140020A patent/CR20140020A/es unknown
- 2014-06-05 US US14/297,065 patent/US9220265B2/en active Active
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2017
- 2017-02-03 JP JP2017019006A patent/JP2017132766A/ja active Pending
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2022
- 2022-06-29 EC ECSENADI202251489A patent/ECSP22051489A/es unknown