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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2013
- 2013-12-17 IL IL229965A patent/IL229965A/en active IP Right Grant
- 2013-12-18 CL CL2013003638A patent/CL2013003638A1/es unknown
-
2014
- 2014-01-10 ZA ZA2014/00232A patent/ZA201400232B/en unknown
- 2014-01-15 CO CO14007084A patent/CO6930356A2/es unknown
- 2014-01-16 CR CR20140020A patent/CR20140020A/es unknown
- 2014-01-16 EC ECSP14013152 patent/ECSP14013152A/es unknown
- 2014-06-05 US US14/297,065 patent/US9220265B2/en active Active
-
2017
- 2017-02-03 JP JP2017019006A patent/JP2017132766A/ja active Pending
-
2022
- 2022-06-29 EC ECSENADI202251489A patent/ECSP22051489A/es unknown
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