JP2016526535A5

JP2016526535A5 -

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Publication number: JP2016526535A5
Authority: JP; Japan
Prior art keywords: difluoro; substituted; ethynyl; tetrazol; difluorophenyl
Prior art date: 2014-06-11
Legal status : Granted

Application number

JP2016519625A

Other languages

English (en)

Japanese (ja)

Other versions

JP6386035B2 (ja

JP2016526535A (ja

Filing date

2014-06-11

Publication date

2017-06-22

2014-06-11 Application filed filed Critical

2014-06-11 Priority claimed from PCT/US2014/041984 external-priority patent/WO2014201161A1/en

2016-09-05 Publication of JP2016526535A publication Critical patent/JP2016526535A/ja

2017-06-22 Publication of JP2016526535A5 publication Critical patent/JP2016526535A5/ja

2018-09-05 Application granted granted Critical

2018-09-05 Publication of JP6386035B2 publication Critical patent/JP6386035B2/ja

Status Expired - Fee Related legal-status Critical Current

2034-06-11 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 127
125000001188 haloalkyl group Chemical group 0.000 claims description 97
125000000547 substituted alkyl group Chemical group 0.000 claims description 91
-1 2- (2,4-difluorophenyl) -1,1-difluoro-2-hydroxy-3- (1H-tetrazol-1-yl) propyl Chemical group 0.000 claims description 85
125000004438 haloalkoxy group Chemical group 0.000 claims description 83
125000000217 alkyl group Chemical group 0.000 claims description 73
125000001072 heteroaryl group Chemical group 0.000 claims description 58
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 56
125000005843 halogen group Chemical group 0.000 claims description 56
125000003710 aryl alkyl group Chemical group 0.000 claims description 51
125000003545 alkoxy group Chemical group 0.000 claims description 49
238000000034 method Methods 0.000 claims description 40
125000003107 substituted aryl group Chemical group 0.000 claims description 35
125000000623 heterocyclic group Chemical group 0.000 claims description 32
125000004093 cyano group Chemical group *C#N 0.000 claims description 30
201000010099 disease Diseases 0.000 claims description 29
125000003118 aryl group Chemical group 0.000 claims description 26
208000035475 disorder Diseases 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 24
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 21
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
229910052751 metal Inorganic materials 0.000 claims description 20
239000002184 metal Substances 0.000 claims description 20
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 19
102000004190 Enzymes Human genes 0.000 claims description 19
108090000790 Enzymes Proteins 0.000 claims description 19
230000003993 interaction Effects 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
230000000694 effects Effects 0.000 claims description 15
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 14
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 14
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
125000001153 fluoro group Chemical group F* 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 11
KWZYOTGGTDCHLM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[[5-(trifluoromethyl)thiophen-2-yl]methoxy]phenyl]ethynyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2SC(=CC=2)C(F)(F)F)=CC=1)(O)CN1C=NN=N1 KWZYOTGGTDCHLM-UHFFFAOYSA-N 0.000 claims description 10
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 10
230000001404 mediated effect Effects 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 10
102000005741 Metalloproteases Human genes 0.000 claims description 9
108010006035 Metalloproteases Proteins 0.000 claims description 9
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
239000011159 matrix material Substances 0.000 claims description 9
108090000353 Histone deacetylase Proteins 0.000 claims description 8
102000003964 Histone deacetylase Human genes 0.000 claims description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 8
229910052742 iron Inorganic materials 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 claims description 7
CHGIKSSZNBCNDW-UHFFFAOYSA-N (3beta,5alpha)-4,4-Dimethylcholesta-8,24-dien-3-ol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21 CHGIKSSZNBCNDW-UHFFFAOYSA-N 0.000 claims description 7
XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 claims description 7
MWJTXCAJFGPQPZ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[(5-fluorothiophen-2-yl)methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2SC(F)=CC=2)=CC=1)(O)CN1C=NN=N1 MWJTXCAJFGPQPZ-UHFFFAOYSA-N 0.000 claims description 7
FPTJELQXIUUCEY-UHFFFAOYSA-N 3beta-Hydroxy-lanostan Natural products C1CC2C(C)(C)C(O)CCC2(C)C2C1C1(C)CCC(C(C)CCCC(C)C)C1(C)CC2 FPTJELQXIUUCEY-UHFFFAOYSA-N 0.000 claims description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 7
BKLIAINBCQPSOV-UHFFFAOYSA-N Gluanol Natural products CC(C)CC=CC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(O)C(C)(C)C4CC3 BKLIAINBCQPSOV-UHFFFAOYSA-N 0.000 claims description 7
101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 claims description 7
LOPKHWOTGJIQLC-UHFFFAOYSA-N Lanosterol Natural products CC(CCC=C(C)C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 LOPKHWOTGJIQLC-UHFFFAOYSA-N 0.000 claims description 7
102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 claims description 7
CAHGCLMLTWQZNJ-UHFFFAOYSA-N Nerifoliol Natural products CC12CCC(O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C CAHGCLMLTWQZNJ-UHFFFAOYSA-N 0.000 claims description 7
QBSJHOGDIUQWTH-UHFFFAOYSA-N dihydrolanosterol Natural products CC(C)CCCC(C)C1CCC2(C)C3=C(CCC12C)C4(C)CCC(C)(O)C(C)(C)C4CC3 QBSJHOGDIUQWTH-UHFFFAOYSA-N 0.000 claims description 7
229940058690 lanosterol Drugs 0.000 claims description 7
CAHGCLMLTWQZNJ-RGEKOYMOSA-N lanosterol Chemical compound C([C@]12C)C[C@@H](O)C(C)(C)[C@H]1CCC1=C2CC[C@]2(C)[C@H]([C@H](CCC=C(C)C)C)CC[C@@]21C CAHGCLMLTWQZNJ-RGEKOYMOSA-N 0.000 claims description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
230000003405 preventing effect Effects 0.000 claims description 6
239000011701 zinc Substances 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
150000002739 metals Chemical class 0.000 claims description 5
229940124597 therapeutic agent Drugs 0.000 claims description 5
SMMCQBIZVOEZER-UHFFFAOYSA-N 1-[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenyl]-2-[4-[(dimethylamino)methyl]phenyl]ethanone Chemical compound C1=CC(CN(C)C)=CC=C1CC(=O)C1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 SMMCQBIZVOEZER-UHFFFAOYSA-N 0.000 claims description 4
KZYVQWCFDFYFPI-UHFFFAOYSA-N 1-[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenyl]-3,3,4,4,4-pentafluorobutan-1-ol Chemical compound C1=CC(C(CC(F)(F)C(F)(F)F)O)=CC=C1C#CC1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 KZYVQWCFDFYFPI-UHFFFAOYSA-N 0.000 claims description 4
YVEPNCOUVHVTRI-UHFFFAOYSA-N 1-[5-[2-[4-(1-amino-2,2,3,3,3-pentafluoropropyl)phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(C(N)C(F)(F)C(F)(F)F)=CC=C1C#CC1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 YVEPNCOUVHVTRI-UHFFFAOYSA-N 0.000 claims description 4
GSKAYKHMBWJMNV-UHFFFAOYSA-N 1-[5-[2-[4-[(4-chloroanilino)methyl]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(CNC=2C=CC(Cl)=CC=2)=CC=1)(O)CN1C=NN=N1 GSKAYKHMBWJMNV-UHFFFAOYSA-N 0.000 claims description 4
LBSOYTIILZKBBF-UHFFFAOYSA-N 1-[5-[2-[4-[(4-chlorophenyl)-hydroxymethyl]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=CC=1C(O)C1=CC=C(Cl)C=C1 LBSOYTIILZKBBF-UHFFFAOYSA-N 0.000 claims description 4
CVGUUIPPPGQTET-UHFFFAOYSA-N 1-[5-[2-[4-[(5-chlorothiophen-2-yl)methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2SC(Cl)=CC=2)=CC=1)(O)CN1C=NN=N1 CVGUUIPPPGQTET-UHFFFAOYSA-N 0.000 claims description 4
HOBLEQIKYHAQKE-UHFFFAOYSA-N 1-[5-[2-[4-[2-(4-chlorophenyl)-1-hydroxyethyl]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=CC=1C(O)CC1=CC=C(Cl)C=C1 HOBLEQIKYHAQKE-UHFFFAOYSA-N 0.000 claims description 4
MLTKPMFOLFLCNL-UHFFFAOYSA-N 1-[5-[2-[4-[[3-[(3-chloro-1,2,4-triazol-1-yl)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=C(CN3N=C(Cl)N=C3)C=CC=2)=CC=1)(O)CN1C=NN=N1 MLTKPMFOLFLCNL-UHFFFAOYSA-N 0.000 claims description 4
ZPQOYWREYJYVGJ-UHFFFAOYSA-N 1-[5-[2-[4-[[4-(2,2-difluoroethoxymethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(COCC(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 ZPQOYWREYJYVGJ-UHFFFAOYSA-N 0.000 claims description 4
ISQXPGQICPDDEH-UHFFFAOYSA-N 1-[5-[2-[4-[[4-(difluoromethyl)-3-fluorophenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=C(F)C(C(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 ISQXPGQICPDDEH-UHFFFAOYSA-N 0.000 claims description 4
VETPSPBJHXUMIP-UHFFFAOYSA-N 1-[5-[2-[4-[[4-(difluoromethyl)anilino]methyl]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(CNC=2C=CC(=CC=2)C(F)F)=CC=1)(O)CN1C=NN=N1 VETPSPBJHXUMIP-UHFFFAOYSA-N 0.000 claims description 4
XKTZBKZVRLWEDW-UHFFFAOYSA-N 1-[5-[2-[4-[[4-[(3-chloropyrazol-1-yl)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3N=C(Cl)C=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 XKTZBKZVRLWEDW-UHFFFAOYSA-N 0.000 claims description 4
XNEHVDNDGLBSFG-UHFFFAOYSA-N 1-[5-[2-[4-[[4-[(4-chloropyrazol-1-yl)methyl]-3-fluorophenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=C(F)C(CN3N=CC(Cl)=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 XNEHVDNDGLBSFG-UHFFFAOYSA-N 0.000 claims description 4
XTVWQCSKCZRFRG-UHFFFAOYSA-N 1-[5-[2-[4-[[4-[(4-chloropyrazol-1-yl)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3N=CC(Cl)=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 XTVWQCSKCZRFRG-UHFFFAOYSA-N 0.000 claims description 4
BOUTUNMDQCCCRD-UHFFFAOYSA-N 1-[5-[2-[4-[[4-[[(2,2-difluoro-2-hydroxyethyl)-methylamino]methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(CN(C)CC(O)(F)F)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 BOUTUNMDQCCCRD-UHFFFAOYSA-N 0.000 claims description 4
CGTWGCHWKFYOBY-UHFFFAOYSA-N 1-[5-[2-[4-[[5-(difluoromethyl)thiophen-2-yl]methoxy]phenyl]ethynyl]pyridin-2-yl]-2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2SC(=CC=2)C(F)F)=CC=1)(O)CN1C=NN=N1 CGTWGCHWKFYOBY-UHFFFAOYSA-N 0.000 claims description 4
MXCWFCYYEIDHPU-UHFFFAOYSA-N 1-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl-methylamino]-2-methylpropan-2-ol Chemical compound C1=CC(CN(C)CC(C)(C)O)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 MXCWFCYYEIDHPU-UHFFFAOYSA-N 0.000 claims description 4
YYFWRLMSEPEZEN-UHFFFAOYSA-N 1-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]-n-methylimidazole-2-carboxamide Chemical compound CNC(=O)C1=NC=CN1CC(C=C1)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 YYFWRLMSEPEZEN-UHFFFAOYSA-N 0.000 claims description 4
FZRQVQHHWAVKSV-UHFFFAOYSA-N 1-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]imidazole-4-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3C=C(N=C3)C#N)=CC=2)=CC=1)(O)CN1C=NN=N1 FZRQVQHHWAVKSV-UHFFFAOYSA-N 0.000 claims description 4
OCZZKEGNBSNPHG-UHFFFAOYSA-N 1-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]imidazolidin-2-one Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3C(NCC3)=O)=CC=2)=CC=1)(O)CN1C=NN=N1 OCZZKEGNBSNPHG-UHFFFAOYSA-N 0.000 claims description 4
GLYQAYBJYAWJRP-UHFFFAOYSA-N 1-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]imidazolidine-2,4-dione Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3C(NC(=O)C3)=O)=CC=2)=CC=1)(O)CN1C=NN=N1 GLYQAYBJYAWJRP-UHFFFAOYSA-N 0.000 claims description 4
HZTPLXQVUPNTOW-UHFFFAOYSA-N 1-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]pyrazole-4-carbonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3N=CC(=C3)C#N)=CC=2)=CC=1)(O)CN1C=NN=N1 HZTPLXQVUPNTOW-UHFFFAOYSA-N 0.000 claims description 4
LBUIJCLOWMDZHP-UHFFFAOYSA-N 1-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC(C=C1)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 LBUIJCLOWMDZHP-UHFFFAOYSA-N 0.000 claims description 4
KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 4
VWATUZNZBJTPFM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[3-(2-hydroxy-1-pyrazol-1-ylethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC=NN1C(CO)C(C=1)=CC=CC=1COC(C=C1)=CC=C1C#CC(C=N1)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1C=NN=N1 VWATUZNZBJTPFM-UHFFFAOYSA-N 0.000 claims description 4
TZRGXDCDWCSASW-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[3-(pyrazol-1-ylmethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=C(CN3N=CC=C3)C=CC=2)=CC=1)(O)CN1C=NN=N1 TZRGXDCDWCSASW-UHFFFAOYSA-N 0.000 claims description 4
ZYUITBYGDUFXKH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[3-fluoro-4-(pyrazol-1-ylmethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=C(F)C(CN3N=CC=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 ZYUITBYGDUFXKH-UHFFFAOYSA-N 0.000 claims description 4
AITXUEMRKLKEAL-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(1-hydroxyethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(C(O)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 AITXUEMRKLKEAL-UHFFFAOYSA-N 0.000 claims description 4
NQQMNLGFIBGSLS-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(1-pyrazol-1-ylethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC=NN1C(C)C(C=C1)=CC=C1COC(C=C1)=CC=C1C#CC(C=N1)=CC=C1C(F)(F)C(O)(C=1C(=CC(F)=CC=1)F)CN1C=NN=N1 NQQMNLGFIBGSLS-UHFFFAOYSA-N 0.000 claims description 4
NNAUSMHNTWRFRS-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(2-hydroxyethoxy)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(OCCO)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 NNAUSMHNTWRFRS-UHFFFAOYSA-N 0.000 claims description 4
WYOMUWIPXVJIQO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(morpholin-4-ylmethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3CCOCC3)=CC=2)=CC=1)(O)CN1C=NN=N1 WYOMUWIPXVJIQO-UHFFFAOYSA-N 0.000 claims description 4
HOOPTQYPCOZSOB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(pyrazol-1-ylmethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3N=CC=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 HOOPTQYPCOZSOB-UHFFFAOYSA-N 0.000 claims description 4
NLIRDJQZVTYAAB-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-(pyrrolidin-1-ylmethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3CCCC3)=CC=2)=CC=1)(O)CN1C=NN=N1 NLIRDJQZVTYAAB-UHFFFAOYSA-N 0.000 claims description 4
JUJDSXNXSGENHH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[(1,3-oxazol-2-ylamino)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CNC=3OC=CN=3)=CC=2)=CC=1)(O)CN1C=NN=N1 JUJDSXNXSGENHH-UHFFFAOYSA-N 0.000 claims description 4
IAKDRXVYNVLKES-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[(4-fluoropyrazol-1-yl)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3N=CC(F)=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 IAKDRXVYNVLKES-UHFFFAOYSA-N 0.000 claims description 4
LZGNMBWRNHSPDA-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[(4-methylpiperazin-1-yl)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1CN(C)CCN1CC(C=C1)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 LZGNMBWRNHSPDA-UHFFFAOYSA-N 0.000 claims description 4
PVKOHIGKPXDILA-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[[2-hydroxypropyl(methyl)amino]methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(CN(C)CC(O)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 PVKOHIGKPXDILA-UHFFFAOYSA-N 0.000 claims description 4
CKTUOEAWMAINCF-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[[4-(1-hydroxyethyl)pyrazol-1-yl]methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=C(C(O)C)C=NN1CC(C=C1)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 CKTUOEAWMAINCF-UHFFFAOYSA-N 0.000 claims description 4
WRAJGSYVOCAYCT-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[[4-(2-hydroxypropan-2-yl)pyrazol-1-yl]methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=C(C(C)(O)C)C=NN1CC(C=C1)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 WRAJGSYVOCAYCT-UHFFFAOYSA-N 0.000 claims description 4
VBRIDLUYWZVABY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[[4-(2-methoxyethyl)pyrazol-1-yl]methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=C(CCOC)C=NN1CC(C=C1)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 VBRIDLUYWZVABY-UHFFFAOYSA-N 0.000 claims description 4
PCDVKWCFMNSBRD-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[4-[[methyl(2,2,2-trifluoroethyl)amino]methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(CN(C)CC(F)(F)F)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 PCDVKWCFMNSBRD-UHFFFAOYSA-N 0.000 claims description 4
SCUQVDYZPFVKML-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-[5-[2-[4-[[5-(pyrazol-1-ylmethyl)thiophen-2-yl]methoxy]phenyl]ethynyl]pyridin-2-yl]-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2SC(CN3N=CC=C3)=CC=2)=CC=1)(O)CN1C=NN=N1 SCUQVDYZPFVKML-UHFFFAOYSA-N 0.000 claims description 4
QJSIDAFXZGMWSO-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-1-pyridin-2-yl-3-(tetrazol-1-yl)propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC=CC=1)(O)CN1C=NN=N1 QJSIDAFXZGMWSO-UHFFFAOYSA-N 0.000 claims description 4
YBYCSFLMHWCJJG-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[(2,2,2-trifluoroethylamino)methyl]phenyl]ethynyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(CNCC(F)(F)F)=CC=1)(O)CN1C=NN=N1 YBYCSFLMHWCJJG-UHFFFAOYSA-N 0.000 claims description 4
NWHWQSRZKIFCTF-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[[4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]propan-2-ol Chemical compound C1=CC(C(O)C(F)(F)F)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 NWHWQSRZKIFCTF-UHFFFAOYSA-N 0.000 claims description 4
JSLLQSWHQWTAQR-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[[4-(2,2,2-trifluoroethoxymethyl)phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(COCC(F)(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 JSLLQSWHQWTAQR-UHFFFAOYSA-N 0.000 claims description 4
FCKZXSSBYARFPX-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[2-[4-[[4-[(2,2,2-trifluoroethylamino)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]propan-2-ol Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CNCC(F)(F)F)=CC=2)=CC=1)(O)CN1C=NN=N1 FCKZXSSBYARFPX-UHFFFAOYSA-N 0.000 claims description 4
QRVHDITUOJTQBQ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[3-(dimethylamino)-2,2-difluoro-1-hydroxypropyl]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(C(O)C(F)(F)CN(C)C)=CC=C1C#CC1=CC=C(C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)N=C1 QRVHDITUOJTQBQ-UHFFFAOYSA-N 0.000 claims description 4
BSCGTXXPOUYUSY-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[3-[(dimethylamino)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound CN(C)CC1=CC=CC(COC=2C=CC(=CC=2)C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 BSCGTXXPOUYUSY-UHFFFAOYSA-N 0.000 claims description 4
LUOXUHROCRVTTE-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[3-[1-(dimethylamino)-2-hydroxyethyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound CN(C)C(CO)C1=CC=CC(COC=2C=CC(=CC=2)C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 LUOXUHROCRVTTE-UHFFFAOYSA-N 0.000 claims description 4
QXRBUKMCPDVWEJ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[4-[(dimethylamino)methyl]-3-fluorophenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=C(F)C(CN(C)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 QXRBUKMCPDVWEJ-UHFFFAOYSA-N 0.000 claims description 4
QODGKEAQAUTMKZ-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[4-[(dimethylamino)methyl]anilino]methyl]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(CN(C)C)=CC=C1NCC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 QODGKEAQAUTMKZ-UHFFFAOYSA-N 0.000 claims description 4
YSGXWCRPCAIFGS-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[4-[(dimethylamino)methyl]phenyl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound C1=CC(CN(C)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 YSGXWCRPCAIFGS-UHFFFAOYSA-N 0.000 claims description 4
OVXLGWLWBGSWHC-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[5-[(dimethylamino)methyl]thiophen-2-yl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound S1C(CN(C)C)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 OVXLGWLWBGSWHC-UHFFFAOYSA-N 0.000 claims description 4
IJMIBOZLCSDLNR-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1-[5-[2-[4-[[5-[(dimethylamino)methyl]thiophen-3-yl]methoxy]phenyl]ethynyl]pyridin-2-yl]-1,1-difluoro-3-(tetrazol-1-yl)propan-2-ol Chemical compound S1C(CN(C)C)=CC(COC=2C=CC(=CC=2)C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)=C1 IJMIBOZLCSDLNR-UHFFFAOYSA-N 0.000 claims description 4
SJSHIOIEIZPUGH-UHFFFAOYSA-N 2-[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 SJSHIOIEIZPUGH-UHFFFAOYSA-N 0.000 claims description 4
RVUBTWDXFKGEDI-UHFFFAOYSA-N 2-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methoxy]acetonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(COCC#N)=CC=2)=CC=1)(O)CN1C=NN=N1 RVUBTWDXFKGEDI-UHFFFAOYSA-N 0.000 claims description 4
CCHVWLHUMXFPQA-UHFFFAOYSA-N 2-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methylamino]acetic acid Chemical compound C1=CC(CNCC(=O)O)=CC=C1COC1=CC=C(C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=C1 CCHVWLHUMXFPQA-UHFFFAOYSA-N 0.000 claims description 4
MVZCVVSHSKSALL-UHFFFAOYSA-N 2-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methylamino]acetonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CNCC#N)=CC=2)=CC=1)(O)CN1C=NN=N1 MVZCVVSHSKSALL-UHFFFAOYSA-N 0.000 claims description 4
ICKOFPONQMXURI-UHFFFAOYSA-N 2-[[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl-methylamino]methyl]imidazole-1-carbaldehyde Chemical compound C=1C=C(COC=2C=CC(=CC=2)C#CC=2C=NC(=CC=2)C(F)(F)C(O)(CN2N=NN=C2)C=2C(=CC(F)=CC=2)F)C=CC=1CN(C)CC1=NC=CN1C=O ICKOFPONQMXURI-UHFFFAOYSA-N 0.000 claims description 4
VLGODEJAXGCYGP-UHFFFAOYSA-N 4-[[4-[2-[6-[1,1-difluoro-2-hydroxy-3,3-dimethyl-2-(tetrazol-1-ylmethyl)butyl]pyridin-3-yl]ethynyl]phenoxy]methyl]benzonitrile Chemical compound C=1C=C(C#CC=2C=CC(OCC=3C=CC(=CC=3)C#N)=CC=2)C=NC=1C(F)(F)C(O)(C(C)(C)C)CN1C=NN=N1 VLGODEJAXGCYGP-UHFFFAOYSA-N 0.000 claims description 4
OHULCLOFTOISKD-UHFFFAOYSA-N 4-[[4-[2-[6-[1,1-difluoro-2-hydroxy-3-methyl-2-(tetrazol-1-ylmethyl)butyl]pyridin-3-yl]ethynyl]phenoxy]methyl]benzonitrile Chemical compound C=1C=C(C#CC=2C=CC(OCC=3C=CC(=CC=3)C#N)=CC=2)C=NC=1C(F)(F)C(O)(C(C)C)CN1C=NN=N1 OHULCLOFTOISKD-UHFFFAOYSA-N 0.000 claims description 4
SQNBTVHAPBTFQH-UHFFFAOYSA-N 4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenyl]methylamino]benzonitrile Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(CNC=2C=CC(=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 SQNBTVHAPBTFQH-UHFFFAOYSA-N 0.000 claims description 4
CPHQGUKBCBSGHB-UHFFFAOYSA-N 4-[[4-[2-[6-[2-cyclopropyl-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]benzonitrile Chemical compound C1CC1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(=CC=2)C#N)=CC=1)(O)CN1C=NN=N1 CPHQGUKBCBSGHB-UHFFFAOYSA-N 0.000 claims description 4
OGUQOXDWJWGPNU-UHFFFAOYSA-N 4-[[4-[[4-[2-[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(tetrazol-1-yl)propyl]pyridin-3-yl]ethynyl]phenoxy]methyl]phenyl]methyl]piperazine-1-carbaldehyde Chemical compound C=1C=C(F)C=C(F)C=1C(C(F)(F)C=1N=CC(=CC=1)C#CC=1C=CC(OCC=2C=CC(CN3CCN(CC3)C=O)=CC=2)=CC=1)(O)CN1C=NN=N1 OGUQOXDWJWGPNU-UHFFFAOYSA-N 0.000 claims description 4
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JP2016519625A 2013-06-12 2014-06-11 金属酵素阻害剤化合物 Expired - Fee Related JP6386035B2 (ja)