JP2012517479A - 糖尿病および肥満の処置においてtgr5アゴニストとして使用するためのトリアゾールおよびイミダゾール誘導体 - Google Patents
糖尿病および肥満の処置においてtgr5アゴニストとして使用するためのトリアゾールおよびイミダゾール誘導体 Download PDFInfo
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- JP2012517479A JP2012517479A JP2011550244A JP2011550244A JP2012517479A JP 2012517479 A JP2012517479 A JP 2012517479A JP 2011550244 A JP2011550244 A JP 2011550244A JP 2011550244 A JP2011550244 A JP 2011550244A JP 2012517479 A JP2012517479 A JP 2012517479A
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- fluorophenyl
- methyl
- alkyl
- methylethyl
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- 238000011282 treatment Methods 0.000 title claims description 39
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- 206010012601 diabetes mellitus Diseases 0.000 title claims 2
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- 101000857733 Homo sapiens G-protein coupled bile acid receptor 1 Proteins 0.000 title abstract description 22
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 title abstract description 21
- 150000003852 triazoles Chemical class 0.000 title description 4
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 257
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- 125000005843 halogen group Chemical group 0.000 claims description 230
- 229910052739 hydrogen Inorganic materials 0.000 claims description 188
- 239000001257 hydrogen Substances 0.000 claims description 188
- 229910052757 nitrogen Inorganic materials 0.000 claims description 160
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 125
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 123
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 114
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 84
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 75
- 125000001424 substituent group Chemical group 0.000 claims description 74
- 238000006467 substitution reaction Methods 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 62
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- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 41
- 125000004122 cyclic group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000003386 piperidinyl group Chemical group 0.000 claims description 34
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- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 29
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000002757 morpholinyl group Chemical group 0.000 claims description 26
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 25
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 25
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
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- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 13
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 13
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 10
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 claims description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
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- 239000003472 antidiabetic agent Substances 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 239000008103 glucose Substances 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 6
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
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- VBHSDTXDKWRVOY-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl VBHSDTXDKWRVOY-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- SDSGLVOBAJECJH-UHFFFAOYSA-N 3,5-difluoro-4-[[1-(4-fluorophenyl)-5-[2-(4-methylsulfonylphenyl)propan-2-yl]imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=C(C(O)=O)C=C1F SDSGLVOBAJECJH-UHFFFAOYSA-N 0.000 claims description 2
- DKEPDCKKWOVNEQ-UHFFFAOYSA-N 3-[[4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoyl]amino]propanoic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(=O)NCCC(O)=O)F)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)=C1 DKEPDCKKWOVNEQ-UHFFFAOYSA-N 0.000 claims description 2
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- CDALMNHTXIVRLE-UHFFFAOYSA-N 3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzenesulfonic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(O)(=O)=O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 CDALMNHTXIVRLE-UHFFFAOYSA-N 0.000 claims description 2
- ZXUWSZCISLIYPN-UHFFFAOYSA-N 3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzoic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(O)=O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 ZXUWSZCISLIYPN-UHFFFAOYSA-N 0.000 claims description 2
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- FUIYQEOHVUHSMC-UHFFFAOYSA-N 4-[[5-[2-(3-cyano-4-fluorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(O)=O)F)C(C)(C)C=2C=C(C(F)=CC=2)C#N)=C1 FUIYQEOHVUHSMC-UHFFFAOYSA-N 0.000 claims description 2
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- QSPKQGHWICQOTO-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-5-[2-[3-chloro-4-(trifluoromethoxy)phenyl]propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(OC(F)(F)F)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl QSPKQGHWICQOTO-UHFFFAOYSA-N 0.000 claims 1
- IYNOGGIKBWXVSB-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methylsulfonyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C1=CN=C(S(=O)(=O)CC=2C(=CC(F)=CC=2)Cl)N1C1=CC=C(F)C=C1 IYNOGGIKBWXVSB-UHFFFAOYSA-N 0.000 claims 1
- OQUJGKIXXMHORR-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methylsulfonyl]-5-[2-(3,4-difluorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(F)C(F)=CC=1C(C)(C)C1=CN=C(S(=O)(=O)CC=2C(=CC(F)=CC=2)Cl)N1C1=CC=C(F)C=C1 OQUJGKIXXMHORR-UHFFFAOYSA-N 0.000 claims 1
- AEENFTZETWFYSH-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)sulfanylmethyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CSC1=CC=C(F)C=C1Cl AEENFTZETWFYSH-UHFFFAOYSA-N 0.000 claims 1
- SIBUOLUAFMJSJU-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)sulfonylmethyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CS(=O)(=O)C1=CC=C(F)C=C1Cl SIBUOLUAFMJSJU-UHFFFAOYSA-N 0.000 claims 1
- KBPHHIMZAXXISL-UHFFFAOYSA-N 2-[(2-chloro-5-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC(F)=CC=C1Cl KBPHHIMZAXXISL-UHFFFAOYSA-N 0.000 claims 1
- XTEUDRUZPHOQBT-UHFFFAOYSA-N 2-[(2-chloro-5-fluorophenyl)methylsulfanyl]-5-[2-(3-chloro-4-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(Cl)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC(F)=CC=C1Cl XTEUDRUZPHOQBT-UHFFFAOYSA-N 0.000 claims 1
- FUXSAEXSYROVEH-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenoxy)methyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1COC1=C(F)C=CC=C1Cl FUXSAEXSYROVEH-UHFFFAOYSA-N 0.000 claims 1
- IEWBZJWHGMUHJD-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenoxy)methyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1COC1=C(F)C=CC=C1Cl IEWBZJWHGMUHJD-UHFFFAOYSA-N 0.000 claims 1
- HIJRSCUCJNJXEH-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-1-(2,4-dichlorophenyl)-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C(=CC(Cl)=CC=2)Cl)=CN=C1SCC1=C(F)C=CC=C1Cl HIJRSCUCJNJXEH-UHFFFAOYSA-N 0.000 claims 1
- SXZCNJLXZMEPGR-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-1-(3,4-dichlorophenyl)-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=C(Cl)C(Cl)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl SXZCNJLXZMEPGR-UHFFFAOYSA-N 0.000 claims 1
- USKKVNSTKLSFDZ-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-1-(4-fluorophenyl)-5-[2-(3-methylsulfonylphenyl)propan-2-yl]imidazole Chemical compound C=1C=CC(S(C)(=O)=O)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl USKKVNSTKLSFDZ-UHFFFAOYSA-N 0.000 claims 1
- BWGBFGHHNMRFRM-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-1-(4-fluorophenyl)-5-[2-(4-fluorophenyl)propan-2-yl]imidazole Chemical compound C=1C=C(F)C=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl BWGBFGHHNMRFRM-UHFFFAOYSA-N 0.000 claims 1
- ZXIRTYKBNFTRPD-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-1-(4-fluorophenyl)-5-[2-(4-methoxyphenyl)propan-2-yl]imidazole Chemical compound C1=CC(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl ZXIRTYKBNFTRPD-UHFFFAOYSA-N 0.000 claims 1
- QGDVTFFTJBTCRP-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-1-(4-fluorophenyl)-5-[2-(4-methylsulfonylphenyl)propan-2-yl]imidazole Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl QGDVTFFTJBTCRP-UHFFFAOYSA-N 0.000 claims 1
- IPMWKDHDUWOHSU-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-1-(4-fluorophenyl)-5-[2-[4-(trifluoromethyl)phenyl]propan-2-yl]imidazole Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl IPMWKDHDUWOHSU-UHFFFAOYSA-N 0.000 claims 1
- AXINPRPHYQNQBD-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-1-cyclopentyl-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C2CCCC2)=CN=C1SCC1=C(F)C=CC=C1Cl AXINPRPHYQNQBD-UHFFFAOYSA-N 0.000 claims 1
- VRLUCPAWCDTWMK-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl VRLUCPAWCDTWMK-UHFFFAOYSA-N 0.000 claims 1
- NAUFMFRMZTWLNH-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[(3,4-dichlorophenyl)-difluoromethyl]-1-(4-fluorophenyl)imidazole Chemical compound C1=CC(F)=CC=C1N1C(C(F)(F)C=2C=C(Cl)C(Cl)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl NAUFMFRMZTWLNH-UHFFFAOYSA-N 0.000 claims 1
- ZLQRYWXARSQWNW-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(2,3-dihydro-1,4-benzodioxin-6-yl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C2OCCOC2=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl ZLQRYWXARSQWNW-UHFFFAOYSA-N 0.000 claims 1
- AYTNRJAARIJUQT-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(2,4-difluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C(=CC(F)=CC=2)F)=CN=C1SCC1=C(F)C=CC=C1Cl AYTNRJAARIJUQT-UHFFFAOYSA-N 0.000 claims 1
- QGGJHTPRWDVAQN-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(3,4-difluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=C(F)C(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl QGGJHTPRWDVAQN-UHFFFAOYSA-N 0.000 claims 1
- VZSVSSOBCAWWDT-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)-4-phenylimidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=C(C=2C=CC=CC=2)N=C1SCC1=C(F)C=CC=C1Cl VZSVSSOBCAWWDT-UHFFFAOYSA-N 0.000 claims 1
- WDHJMIKBZJHGDC-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-[(4-fluorophenyl)methyl]imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1CC=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl WDHJMIKBZJHGDC-UHFFFAOYSA-N 0.000 claims 1
- UVHVDRPZOQQDPD-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-propan-2-ylimidazole Chemical compound N=1C=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N(C(C)C)C=1SCC1=C(F)C=CC=C1Cl UVHVDRPZOQQDPD-UHFFFAOYSA-N 0.000 claims 1
- PRZUHRUGCUSRNY-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-difluorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(F)C(F)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl PRZUHRUGCUSRNY-UHFFFAOYSA-N 0.000 claims 1
- ZSBFGMYBKQOWLK-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-4-(4-fluorophenyl)-1-methylimidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C)=C(C=2C=CC(F)=CC=2)N=C1SCC1=C(F)C=CC=C1Cl ZSBFGMYBKQOWLK-UHFFFAOYSA-N 0.000 claims 1
- BSMNKXBVAVXUFK-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,5-dichloro-4-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl BSMNKXBVAVXUFK-UHFFFAOYSA-N 0.000 claims 1
- SZQIZEAGBSQINP-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3-chloro-4-fluorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(F)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl SZQIZEAGBSQINP-UHFFFAOYSA-N 0.000 claims 1
- QIQDFXQHIFPNOL-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3-chloro-4-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(Cl)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl QIQDFXQHIFPNOL-UHFFFAOYSA-N 0.000 claims 1
- XFCSOLIKYAGPSP-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(4-chloro-2-fluorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C=C(F)C=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl XFCSOLIKYAGPSP-UHFFFAOYSA-N 0.000 claims 1
- OVQFXRULCGTMSO-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)-4-methylimidazole Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC=CC=3F)Cl)=NC=2C)C=2C=CC(F)=CC=2)=C1 OVQFXRULCGTMSO-UHFFFAOYSA-N 0.000 claims 1
- YAKBTKXDFYZLQH-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 YAKBTKXDFYZLQH-UHFFFAOYSA-N 0.000 claims 1
- QKKZWUOPUHORTH-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(4-chlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl QKKZWUOPUHORTH-UHFFFAOYSA-N 0.000 claims 1
- CFHAJESNAQDJFS-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfonyl]-1-(3,4-dichlorophenyl)-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C1=CN=C(S(=O)(=O)CC=2C(=CC=CC=2F)Cl)N1C1=CC=C(Cl)C(Cl)=C1 CFHAJESNAQDJFS-UHFFFAOYSA-N 0.000 claims 1
- IDWASVJCHZPZOT-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfonyl]-1-(4-chlorophenyl)-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C1=CN=C(S(=O)(=O)CC=2C(=CC=CC=2F)Cl)N1C1=CC=C(Cl)C=C1 IDWASVJCHZPZOT-UHFFFAOYSA-N 0.000 claims 1
- YCQHLGAECQMNLJ-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfonyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(2,4-difluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C1=CN=C(S(=O)(=O)CC=2C(=CC=CC=2F)Cl)N1C1=CC=C(F)C=C1F YCQHLGAECQMNLJ-UHFFFAOYSA-N 0.000 claims 1
- ACEFDTQLERMZIZ-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)methylsulfonyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C1=CN=C(S(=O)(=O)CC=2C(=CC=CC=2F)Cl)N1C1=CC=C(F)C=C1 ACEFDTQLERMZIZ-UHFFFAOYSA-N 0.000 claims 1
- ZMMKHBXCGGAXRN-UHFFFAOYSA-N 2-[(2-chloro-6-fluorophenyl)sulfanylmethyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CSC1=C(F)C=CC=C1Cl ZMMKHBXCGGAXRN-UHFFFAOYSA-N 0.000 claims 1
- METKUGUILMSFDI-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methylsulfanyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(Cl)C(Cl)=C1 METKUGUILMSFDI-UHFFFAOYSA-N 0.000 claims 1
- KNMVGSNOMQAETF-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methylsulfonyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C1=CN=C(S(=O)(=O)CC=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 KNMVGSNOMQAETF-UHFFFAOYSA-N 0.000 claims 1
- OHFVNKRDTPDPIB-UHFFFAOYSA-N 2-[(3-chloro-4-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(Cl)=C1 OHFVNKRDTPDPIB-UHFFFAOYSA-N 0.000 claims 1
- AMWBNFLEKSCGHQ-UHFFFAOYSA-N 2-[(3-chloro-4-fluorophenyl)methylsulfonyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C1=CN=C(S(=O)(=O)CC=2C=C(Cl)C(F)=CC=2)N1C1=CC=C(F)C=C1 AMWBNFLEKSCGHQ-UHFFFAOYSA-N 0.000 claims 1
- RDOMVYMYZLRKCK-UHFFFAOYSA-N 2-[(3-chloro-5-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC(F)=CC(Cl)=C1 RDOMVYMYZLRKCK-UHFFFAOYSA-N 0.000 claims 1
- MXVWHQBVEDPIHZ-ACCUITESSA-N 2-[(e)-2-(2-chloro-6-fluorophenyl)ethenyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1\C=C\C1=C(F)C=CC=C1Cl MXVWHQBVEDPIHZ-ACCUITESSA-N 0.000 claims 1
- WVRZZQAOHJIQPL-UHFFFAOYSA-N 2-[1-(2-chloro-4-fluorophenyl)sulfanylethyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound N=1C=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N(C=2C=CC(F)=CC=2)C=1C(C)SC1=CC=C(F)C=C1Cl WVRZZQAOHJIQPL-UHFFFAOYSA-N 0.000 claims 1
- RHWWFCXMONYQNS-UHFFFAOYSA-N 2-[1-(2-chloro-4-fluorophenyl)sulfonylethyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(F)C=C(Cl)C=1S(=O)(=O)C(C)C1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 RHWWFCXMONYQNS-UHFFFAOYSA-N 0.000 claims 1
- WRWCKVXIFCPIQB-UHFFFAOYSA-N 2-[1-(3,4-dichlorophenoxy)ethyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound N=1C=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N(C=2C=CC(F)=CC=2)C=1C(C)OC1=CC=C(Cl)C(Cl)=C1 WRWCKVXIFCPIQB-UHFFFAOYSA-N 0.000 claims 1
- GDELKNUEMJEFSO-UHFFFAOYSA-N 2-[2-(2-chloro-4-fluorophenyl)ethylsulfonyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C1=CN=C(S(=O)(=O)CCC=2C(=CC(F)=CC=2)Cl)N1C1=CC=C(F)C=C1 GDELKNUEMJEFSO-UHFFFAOYSA-N 0.000 claims 1
- PWTKSBKOHBGWBM-UHFFFAOYSA-N 2-[2-(2-chloro-6-fluorophenyl)ethyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CCC1=C(F)C=CC=C1Cl PWTKSBKOHBGWBM-UHFFFAOYSA-N 0.000 claims 1
- WQIUFXMBUQIINC-UHFFFAOYSA-N 2-[2-(2-chloro-6-fluorophenyl)ethyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CCC1=C(F)C=CC=C1Cl WQIUFXMBUQIINC-UHFFFAOYSA-N 0.000 claims 1
- QXNXZNQOYCDOIE-UHFFFAOYSA-N 2-[2-(2-chloro-6-fluorophenyl)propan-2-ylsulfonyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C1=CN=C(S(=O)(=O)C(C)(C)C=2C(=CC=CC=2F)Cl)N1C1=CC=C(F)C=C1 QXNXZNQOYCDOIE-UHFFFAOYSA-N 0.000 claims 1
- YEGVFBAQKSKDJF-UHFFFAOYSA-N 2-[2-(3,4-dichlorophenyl)ethylsulfonyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C1=CN=C(S(=O)(=O)CCC=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 YEGVFBAQKSKDJF-UHFFFAOYSA-N 0.000 claims 1
- NEXDDGWTIUQBMJ-UHFFFAOYSA-N 2-[2-(3-chloro-4-fluorophenyl)ethylsulfonyl]-5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C1=CN=C(S(=O)(=O)CCC=2C=C(Cl)C(F)=CC=2)N1C1=CC=C(F)C=C1 NEXDDGWTIUQBMJ-UHFFFAOYSA-N 0.000 claims 1
- XFMYKIQIAVCGOR-UHFFFAOYSA-N 2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazol-1-yl]-n,n-dimethylethanamine Chemical compound N=1C=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N(CCN(C)C)C=1SCC1=C(F)C=CC=C1Cl XFMYKIQIAVCGOR-UHFFFAOYSA-N 0.000 claims 1
- BPNVNWPLZBXVOL-UHFFFAOYSA-N 2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazol-1-yl]ethanol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1CCO)=CN=C1SCC1=C(F)C=CC=C1Cl BPNVNWPLZBXVOL-UHFFFAOYSA-N 0.000 claims 1
- GHPIRRQMDDPVIN-UHFFFAOYSA-N 2-[2-[2-chloro-5-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-4-fluorophenoxy]ethyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(Cl)=C(OCCNC(N)=N)C=3)F)=NC=2)C=2C=CC(F)=CC=2)=C1 GHPIRRQMDDPVIN-UHFFFAOYSA-N 0.000 claims 1
- TYJXLBAZIHOMPZ-UHFFFAOYSA-N 2-[2-[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenoxy]ethyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(OCCNC(N)=N)=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 TYJXLBAZIHOMPZ-UHFFFAOYSA-N 0.000 claims 1
- SBTUGLUNVHUTRC-UHFFFAOYSA-N 2-[2-[3-chloro-5-fluoro-4-[[5-[2-(4-fluoro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenoxy]ethyl]guanidine Chemical compound C1=C(F)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(OCCNC(N)=N)=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 SBTUGLUNVHUTRC-UHFFFAOYSA-N 0.000 claims 1
- YGLMALZVEIWMPR-UHFFFAOYSA-N 2-[2-[4-[[5-[2-(3-chloro-4-fluorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenoxy]ethyl]guanidine Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(OCCNC(N)=N)=CC=2F)F)C(C)(C)C=2C=C(Cl)C(F)=CC=2)=C1 YGLMALZVEIWMPR-UHFFFAOYSA-N 0.000 claims 1
- ITNKBVGJKSRPGI-UHFFFAOYSA-N 2-[2-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenoxy]ethyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(OCCNC(N)=N)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 ITNKBVGJKSRPGI-UHFFFAOYSA-N 0.000 claims 1
- VLQDTECSAKUSCB-UHFFFAOYSA-N 2-[2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorophenyl]propan-2-ol Chemical compound CC(C)(O)C1=CC=CC(F)=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 VLQDTECSAKUSCB-UHFFFAOYSA-N 0.000 claims 1
- SNYSCOJXPRYYDX-UHFFFAOYSA-N 2-[2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenoxy]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC(F)=CC=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 SNYSCOJXPRYYDX-UHFFFAOYSA-N 0.000 claims 1
- BAIZMWHVBJDJNY-UHFFFAOYSA-N 2-[2-chloro-4-[2-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]-2-methylpropanoic acid Chemical compound C1=C(Cl)C(OC(C)(C)C(O)=O)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl BAIZMWHVBJDJNY-UHFFFAOYSA-N 0.000 claims 1
- BNHCLOGNOMHNKF-UHFFFAOYSA-N 2-[2-chloro-4-[2-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl BNHCLOGNOMHNKF-UHFFFAOYSA-N 0.000 claims 1
- QLZLKIFCRLOKDU-UHFFFAOYSA-N 2-[2-chloro-4-[2-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenyl]propan-2-ol Chemical compound C1=C(Cl)C(C(C)(O)C)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl QLZLKIFCRLOKDU-UHFFFAOYSA-N 0.000 claims 1
- ODVVEYTZHACZFQ-UHFFFAOYSA-N 2-[2-chloro-5-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]-n,n-diethylethanamine Chemical compound C1=C(Cl)C(OCCN(CC)CC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 ODVVEYTZHACZFQ-UHFFFAOYSA-N 0.000 claims 1
- UDIAULSPTRXFSQ-UHFFFAOYSA-N 2-[2-chloro-5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenyl]propan-2-ol Chemical compound C1=C(Cl)C(C(C)(O)C)=CC(CSC=2N(C(=CN=2)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)C=2C=CC(F)=CC=2)=C1 UDIAULSPTRXFSQ-UHFFFAOYSA-N 0.000 claims 1
- MZAZIEZDVZPXKD-UHFFFAOYSA-N 2-[3-(diaminomethylideneamino)propyl]-5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C=C(C(CCCNC(N)=N)=CC=2)C(O)=O)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)=C1 MZAZIEZDVZPXKD-UHFFFAOYSA-N 0.000 claims 1
- DSGSBVXQVCWFIS-UHFFFAOYSA-N 2-[3-[2-chloro-4-fluoro-3-[[5-[2-(4-fluoro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenoxy]propyl]guanidine Chemical compound C1=C(F)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=C(OCCCNC(N)=N)C=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 DSGSBVXQVCWFIS-UHFFFAOYSA-N 0.000 claims 1
- INHOHAYCKPCICV-UHFFFAOYSA-N 2-[3-[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenoxy]propyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(OCCCNC(N)=N)=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 INHOHAYCKPCICV-UHFFFAOYSA-N 0.000 claims 1
- OPVDRCRUPSPCAT-UHFFFAOYSA-N 2-[3-[3-chloro-5-fluoro-4-[[5-[2-(4-fluoro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenoxy]propyl]guanidine Chemical compound C1=C(F)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(OCCCNC(N)=N)=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 OPVDRCRUPSPCAT-UHFFFAOYSA-N 0.000 claims 1
- RHKHIDJISHJIFX-UHFFFAOYSA-N 2-[3-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenoxy]propyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(OCCCNC(N)=N)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 RHKHIDJISHJIFX-UHFFFAOYSA-N 0.000 claims 1
- GLQRJQJRTLYSMK-UHFFFAOYSA-N 2-[3-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]prop-2-ynyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C#CCNC(N)=N)F)=NC=2)C=2C=CC(F)=CC=2)=C1 GLQRJQJRTLYSMK-UHFFFAOYSA-N 0.000 claims 1
- PRHBBCJLEVKFHN-UHFFFAOYSA-N 2-[3-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]propyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(CCCNC(N)=N)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 PRHBBCJLEVKFHN-UHFFFAOYSA-N 0.000 claims 1
- OEOHGZPMPQYXTN-UHFFFAOYSA-N 2-[3-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-4-fluorophenyl]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C(F)C(CSC=2N(C(=CN=2)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)C=2C=CC(F)=CC=2)=C1 OEOHGZPMPQYXTN-UHFFFAOYSA-N 0.000 claims 1
- UEVILKXYQZSLGI-UHFFFAOYSA-N 2-[3-chloro-4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenyl]propan-2-ol Chemical compound ClC1=CC(C(C)(O)C)=CC=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 UEVILKXYQZSLGI-UHFFFAOYSA-N 0.000 claims 1
- IEKUXJUUMJLONS-UHFFFAOYSA-N 2-[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenyl]propan-2-ol Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(C)(C)O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 IEKUXJUUMJLONS-UHFFFAOYSA-N 0.000 claims 1
- MJUOLCCEUNDXOD-UHFFFAOYSA-N 2-[4-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]-n,n-dimethylethanamine Chemical compound C1=CC(OCCN(C)C)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl MJUOLCCEUNDXOD-UHFFFAOYSA-N 0.000 claims 1
- JSHFBMDOSSFEOY-UHFFFAOYSA-N 2-[4-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]acetic acid Chemical compound C=1C=C(OCC(O)=O)C=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl JSHFBMDOSSFEOY-UHFFFAOYSA-N 0.000 claims 1
- AURTZUFYDGLWLL-UHFFFAOYSA-N 2-[4-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C=C(OCCO)C=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl AURTZUFYDGLWLL-UHFFFAOYSA-N 0.000 claims 1
- SGJOMKIAOSTNFG-UHFFFAOYSA-N 2-[4-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]butyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(CCCCNC(N)=N)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 SGJOMKIAOSTNFG-UHFFFAOYSA-N 0.000 claims 1
- XOWCJNQWXSHPPI-UHFFFAOYSA-N 2-[4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-(2h-tetrazol-5-yl)phenoxy]-n,n-diethylethanamine Chemical compound C1=C(C=2NN=NN=2)C(OCCN(CC)CC)=CC=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 XOWCJNQWXSHPPI-UHFFFAOYSA-N 0.000 claims 1
- KELXJFJSQDUTKT-UHFFFAOYSA-N 2-[4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorophenyl]-2-methylpropanoic acid Chemical compound FC1=CC(C(C)(C(O)=O)C)=CC=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 KELXJFJSQDUTKT-UHFFFAOYSA-N 0.000 claims 1
- ADGVBTUYOGFCOL-UHFFFAOYSA-N 2-[4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorophenyl]propan-2-ol Chemical compound FC1=CC(C(C)(O)C)=CC=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 ADGVBTUYOGFCOL-UHFFFAOYSA-N 0.000 claims 1
- XXKZIUUVFGQSKT-UHFFFAOYSA-N 2-[4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]piperidin-1-yl]sulfonyl-n,n-diethylethanamine Chemical compound C1CN(S(=O)(=O)CCN(CC)CC)CCC1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 XXKZIUUVFGQSKT-UHFFFAOYSA-N 0.000 claims 1
- MFNSFYJVLURBNI-UHFFFAOYSA-N 2-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]piperidin-1-yl]acetic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC3CCN(CC(O)=O)CC3)=NC=2)C=2C=CC(F)=CC=2)=C1 MFNSFYJVLURBNI-UHFFFAOYSA-N 0.000 claims 1
- CJHPUCFSWWEAHB-UHFFFAOYSA-N 2-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]piperidin-1-yl]ethanol Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC3CCN(CCO)CC3)=NC=2)C=2C=CC(F)=CC=2)=C1 CJHPUCFSWWEAHB-UHFFFAOYSA-N 0.000 claims 1
- GCYLPPHBRPMNIM-UHFFFAOYSA-N 2-[5-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazol-1-yl]-2-fluorophenoxy]-2-methylpropanoic acid Chemical compound C1=C(F)C(OC(C)(C)C(O)=O)=CC(N2C(=CN=C2SCC=2C(=CC(F)=CC=2)Cl)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)=C1 GCYLPPHBRPMNIM-UHFFFAOYSA-N 0.000 claims 1
- BPXOCOLXEZKBQV-UHFFFAOYSA-N 2-[5-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazol-1-yl]-2-fluorophenoxy]acetic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=C(OCC(O)=O)C(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl BPXOCOLXEZKBQV-UHFFFAOYSA-N 0.000 claims 1
- HFVGOBMATJCZIJ-UHFFFAOYSA-N 2-[5-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]pentyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(CCCCCNC(N)=N)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 HFVGOBMATJCZIJ-UHFFFAOYSA-N 0.000 claims 1
- TZWMTKKGLCSQRP-UHFFFAOYSA-N 2-[5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenoxy]-2-methylpropanoic acid Chemical compound C1=C(F)C(OC(C)(C)C(O)=O)=CC(CSC=2N(C(=CN=2)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)C=2C=CC(F)=CC=2)=C1 TZWMTKKGLCSQRP-UHFFFAOYSA-N 0.000 claims 1
- FKRYLSHMARZMHH-UHFFFAOYSA-N 2-[5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenyl]-2-methylpropanoic acid Chemical compound C1=C(F)C(C(C)(C(O)=O)C)=CC(CSC=2N(C(=CN=2)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)C=2C=CC(F)=CC=2)=C1 FKRYLSHMARZMHH-UHFFFAOYSA-N 0.000 claims 1
- QXJSGSVIMUAZQP-UHFFFAOYSA-N 2-[5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenyl]guanidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(NC(N)=N)=C1 QXJSGSVIMUAZQP-UHFFFAOYSA-N 0.000 claims 1
- MWQCPFZFVSVRHD-UHFFFAOYSA-N 2-[5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenyl]propan-2-ol Chemical compound C1=C(F)C(C(C)(O)C)=CC(CSC=2N(C(=CN=2)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)C=2C=CC(F)=CC=2)=C1 MWQCPFZFVSVRHD-UHFFFAOYSA-N 0.000 claims 1
- NSOZLBQKFCCIEX-UHFFFAOYSA-N 2-[[3-chloro-4-[2-[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]ethyl]-5-fluorobenzoyl]amino]ethanesulfonic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CCC1=C(F)C=C(C(=O)NCCS(O)(=O)=O)C=C1Cl NSOZLBQKFCCIEX-UHFFFAOYSA-N 0.000 claims 1
- TULCRVBIUALVLZ-UHFFFAOYSA-N 2-[[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzoyl]amino]ethanesulfonic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(=O)NCCS(O)(=O)=O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 TULCRVBIUALVLZ-UHFFFAOYSA-N 0.000 claims 1
- IOCIAQJWXQEQFO-UHFFFAOYSA-N 2-[[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenyl]sulfonylamino]ethanesulfonic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)NCCS(O)(=O)=O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 IOCIAQJWXQEQFO-UHFFFAOYSA-N 0.000 claims 1
- TZXHOKUJDGALAY-UHFFFAOYSA-N 2-[[4-[[1-(3-chloro-4-fluorophenyl)-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoyl]amino]ethanesulfonic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=C(Cl)C(F)=CC=2)=CN=C1SCC1=C(F)C=C(C(=O)NCCS(O)(=O)=O)C=C1F TZXHOKUJDGALAY-UHFFFAOYSA-N 0.000 claims 1
- STODIHJNCFBLJU-UHFFFAOYSA-N 2-[[4-[[5-[2-(3-chloro-4-sulfamoylphenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoyl]amino]ethanesulfonic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(=O)NCCS(O)(=O)=O)F)C(C)(C)C=2C=C(Cl)C(=CC=2)S(N)(=O)=O)=C1 STODIHJNCFBLJU-UHFFFAOYSA-N 0.000 claims 1
- VNFNVPIKUOSHMF-UHFFFAOYSA-N 2-[[4-[[5-[2-(3-chloro-4-sulfamoylphenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorobenzoyl]amino]ethanesulfonic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2)C(=O)NCCS(O)(=O)=O)F)C(C)(C)C=2C=C(Cl)C(=CC=2)S(N)(=O)=O)=C1 VNFNVPIKUOSHMF-UHFFFAOYSA-N 0.000 claims 1
- BJOOQFYRHYRCRK-UHFFFAOYSA-N 2-[[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoyl]amino]ethanesulfonic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(=O)NCCS(O)(=O)=O)F)=NC=2)C=2C=CC(F)=CC=2)=C1 BJOOQFYRHYRCRK-UHFFFAOYSA-N 0.000 claims 1
- HMNWNYSSKKTPIU-UHFFFAOYSA-N 2-[[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]sulfonylamino]ethanesulfonic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)NCCS(O)(=O)=O)F)=NC=2)C=2C=CC(F)=CC=2)=C1 HMNWNYSSKKTPIU-UHFFFAOYSA-N 0.000 claims 1
- YUXZQAHIKUTLHR-UHFFFAOYSA-N 2-[[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorobenzoyl]amino]ethanesulfonic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3)C(=O)NCCS(O)(=O)=O)F)=NC=2)C=2C=CC(F)=CC=2)=C1 YUXZQAHIKUTLHR-UHFFFAOYSA-N 0.000 claims 1
- VPMPFSBXYZSWLR-UHFFFAOYSA-N 2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorobenzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1C(O)=O VPMPFSBXYZSWLR-UHFFFAOYSA-N 0.000 claims 1
- CEOYHLLNIPQMQD-UHFFFAOYSA-N 2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1C(N)=O CEOYHLLNIPQMQD-UHFFFAOYSA-N 0.000 claims 1
- XEHCJPXIPFZETL-UHFFFAOYSA-N 2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzenesulfonamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1S(N)(=O)=O XEHCJPXIPFZETL-UHFFFAOYSA-N 0.000 claims 1
- CKZAOTKVPRPSNE-UHFFFAOYSA-N 2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1C(O)=O CKZAOTKVPRPSNE-UHFFFAOYSA-N 0.000 claims 1
- QTFSFOSWOSJXFX-UHFFFAOYSA-N 2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzonitrile Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1C#N QTFSFOSWOSJXFX-UHFFFAOYSA-N 0.000 claims 1
- OKXGSVVOKAWAHW-UHFFFAOYSA-N 2-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorobenzoic acid Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1C(O)=O OKXGSVVOKAWAHW-UHFFFAOYSA-N 0.000 claims 1
- FLRMKFJFLWAOAE-UHFFFAOYSA-N 2-chloro-4-[2-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]benzonitrile Chemical compound C=1C=C(C#N)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl FLRMKFJFLWAOAE-UHFFFAOYSA-N 0.000 claims 1
- KLRAVMWKAHEJBH-UHFFFAOYSA-N 2-chloro-4-[2-[2-[(2-chloro-4-sulfamoylphenyl)methylsulfanyl]-3-(4-fluoro-3-methoxyphenyl)imidazol-4-yl]propan-2-yl]benzenesulfonamide Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2)S(N)(=O)=O)Cl)C(C)(C)C=2C=C(Cl)C(=CC=2)S(N)(=O)=O)=C1 KLRAVMWKAHEJBH-UHFFFAOYSA-N 0.000 claims 1
- SMYYKELFMXXOML-UHFFFAOYSA-N 2-chloro-4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(C(O)=O)C(Cl)=C1 SMYYKELFMXXOML-UHFFFAOYSA-N 0.000 claims 1
- HHZYVPDWZWNAJK-UHFFFAOYSA-N 2-chloro-4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzonitrile Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(C#N)C(Cl)=C1 HHZYVPDWZWNAJK-UHFFFAOYSA-N 0.000 claims 1
- RDMXHUMXJXGOPR-UHFFFAOYSA-N 2-chloro-5-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenol Chemical compound C=1C=C(Cl)C(O)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl RDMXHUMXJXGOPR-UHFFFAOYSA-N 0.000 claims 1
- AROPFGHNSCZIGK-UHFFFAOYSA-N 2-chloro-5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(Cl)C(C(O)=O)=C1 AROPFGHNSCZIGK-UHFFFAOYSA-N 0.000 claims 1
- QSNBKUFBQXSMSU-UHFFFAOYSA-N 2-chloro-5-[[5-[2-(3-chloro-4-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(Cl)C(C(O)=O)=C1 QSNBKUFBQXSMSU-UHFFFAOYSA-N 0.000 claims 1
- QIBPXBISDGYZAH-UHFFFAOYSA-N 2-chloro-5-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-4-fluorobenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(Cl)=C(C=3)S(N)(=O)=O)F)=NC=2)C=2C=CC(F)=CC=2)=C1 QIBPXBISDGYZAH-UHFFFAOYSA-N 0.000 claims 1
- KQGHPLPJGFJUQK-UHFFFAOYSA-N 2-chloro-n-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methyl]-6-fluoro-n-methylaniline Chemical compound FC=1C=CC=C(Cl)C=1N(C)CC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 KQGHPLPJGFJUQK-UHFFFAOYSA-N 0.000 claims 1
- WJCUYNCHFCCACX-UHFFFAOYSA-N 2-chloro-n-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methyl]-4-fluoroaniline Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CNC1=CC=C(F)C=C1Cl WJCUYNCHFCCACX-UHFFFAOYSA-N 0.000 claims 1
- BDZJZIYALJVTBQ-UHFFFAOYSA-N 2-chloro-n-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methyl]-6-fluoro-n-methylaniline Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CN(C)C1=C(F)C=CC=C1Cl BDZJZIYALJVTBQ-UHFFFAOYSA-N 0.000 claims 1
- RCUSPWLYMDXEDW-UHFFFAOYSA-N 2-chloro-n-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methyl]-6-fluoroaniline Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CNC1=C(F)C=CC=C1Cl RCUSPWLYMDXEDW-UHFFFAOYSA-N 0.000 claims 1
- GUPYZDOXEOZCRM-UHFFFAOYSA-N 3,4-dichloro-n-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methyl]aniline Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CNC1=CC=C(Cl)C(Cl)=C1 GUPYZDOXEOZCRM-UHFFFAOYSA-N 0.000 claims 1
- QZMOGTSQYPIPJN-UHFFFAOYSA-N 3,5-difluoro-4-[[1-(4-fluoro-3-methoxyphenyl)-5-[2-(3-methylsulfonylphenyl)propan-2-yl]imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(O)=O)F)C(C)(C)C=2C=C(C=CC=2)S(C)(=O)=O)=C1 QZMOGTSQYPIPJN-UHFFFAOYSA-N 0.000 claims 1
- PABWZFKEBRQOHP-UHFFFAOYSA-N 3,5-difluoro-4-[[1-(4-fluoro-3-methoxyphenyl)-5-[2-(4-methylsulfonylphenyl)propan-2-yl]imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(O)=O)F)C(C)(C)C=2C=CC(=CC=2)S(C)(=O)=O)=C1 PABWZFKEBRQOHP-UHFFFAOYSA-N 0.000 claims 1
- QQNABAHFONGRLO-UHFFFAOYSA-N 3,5-difluoro-4-[[1-(4-fluoro-3-methoxyphenyl)-5-[2-(4-sulfamoylphenyl)propan-2-yl]imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(O)=O)F)C(C)(C)C=2C=CC(=CC=2)S(N)(=O)=O)=C1 QQNABAHFONGRLO-UHFFFAOYSA-N 0.000 claims 1
- IVIIDGANIIUFJU-UHFFFAOYSA-N 3,5-difluoro-4-[[1-(4-fluorophenyl)-5-(2-naphthalen-2-ylpropan-2-yl)imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=C(C(O)=O)C=C1F IVIIDGANIIUFJU-UHFFFAOYSA-N 0.000 claims 1
- CBKJFQJZPYOGSH-UHFFFAOYSA-N 3,5-difluoro-4-[[1-(5-fluoropyridin-2-yl)-5-[2-(4-methylsulfonylphenyl)propan-2-yl]imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(C)(C)C(N1C=2N=CC(F)=CC=2)=CN=C1SCC1=C(F)C=C(C(O)=O)C=C1F CBKJFQJZPYOGSH-UHFFFAOYSA-N 0.000 claims 1
- KCMJJQVHGSHGDQ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]propan-1-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1C(O)CCC1=CC=C(Cl)C=C1Cl KCMJJQVHGSHGDQ-UHFFFAOYSA-N 0.000 claims 1
- VIJQXHNBSGGOMN-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)-1-[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]propan-1-one Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1C(=O)CCC1=CC=C(Cl)C=C1Cl VIJQXHNBSGGOMN-UHFFFAOYSA-N 0.000 claims 1
- GCIAEBRQIBMDKS-UHFFFAOYSA-N 3-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazol-1-yl]pyridine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=NC=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl GCIAEBRQIBMDKS-UHFFFAOYSA-N 0.000 claims 1
- QVQULIYFJDAYSP-UHFFFAOYSA-N 3-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]imidazol-1-yl]pyridine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC=CC=3F)Cl)=NC=2)C=2C=NC=CC=2)=C1 QVQULIYFJDAYSP-UHFFFAOYSA-N 0.000 claims 1
- WSRPYOQTKVKJLB-UHFFFAOYSA-N 3-[2-chloro-5-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]propan-1-ol Chemical compound C=1C=C(Cl)C(OCCCO)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl WSRPYOQTKVKJLB-UHFFFAOYSA-N 0.000 claims 1
- PBGRVNXMOSSRLN-UHFFFAOYSA-N 3-[4-[[5-[2-(3,4-difluorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]piperidin-1-yl]propane-1,2-diol Chemical compound C=1C=C(F)C(F)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1CCN(CC(O)CO)CC1 PBGRVNXMOSSRLN-UHFFFAOYSA-N 0.000 claims 1
- JMPPZDJVROJWPY-UHFFFAOYSA-N 3-[4-[[5-[2-(3-chloro-4-fluorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]-n,n-dimethylpropan-1-amine Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(CCCN(C)C)=CC=2F)F)C(C)(C)C=2C=C(Cl)C(F)=CC=2)=C1 JMPPZDJVROJWPY-UHFFFAOYSA-N 0.000 claims 1
- JPQPRUDOWHQXCO-UHFFFAOYSA-N 3-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]-2h-1,2,4-oxadiazol-5-one Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C=3NC(=O)ON=3)F)=NC=2)C=2C=CC(F)=CC=2)=C1 JPQPRUDOWHQXCO-UHFFFAOYSA-N 0.000 claims 1
- YFKAEDKXRCTHPJ-UHFFFAOYSA-N 3-[[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenyl]sulfonylcarbamoylamino]propanoic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3)S(=O)(=O)NC(=O)NCCC(O)=O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 YFKAEDKXRCTHPJ-UHFFFAOYSA-N 0.000 claims 1
- LTZUKWLHXPZLCM-UHFFFAOYSA-N 3-[[4-[[5-[2-(3-chloro-4-sulfamoylphenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoyl]amino]propanoic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(=O)NCCC(O)=O)F)C(C)(C)C=2C=C(Cl)C(=CC=2)S(N)(=O)=O)=C1 LTZUKWLHXPZLCM-UHFFFAOYSA-N 0.000 claims 1
- LYFYWBYXIWUSIC-UHFFFAOYSA-N 3-[[4-[[5-[2-(3-chloro-4-sulfamoylphenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorobenzoyl]amino]propanoic acid Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2)C(=O)NCCC(O)=O)F)C(C)(C)C=2C=C(Cl)C(=CC=2)S(N)(=O)=O)=C1 LYFYWBYXIWUSIC-UHFFFAOYSA-N 0.000 claims 1
- YINKOADDSOJONO-UHFFFAOYSA-N 3-[[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3-fluorobenzoyl]amino]propanoic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3)C(=O)NCCC(O)=O)F)=NC=2)C=2C=CC(F)=CC=2)=C1 YINKOADDSOJONO-UHFFFAOYSA-N 0.000 claims 1
- UNZDSWVYQUPIEW-UHFFFAOYSA-N 3-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-1-(2h-tetrazol-5-yl)piperidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC(C1)CCCN1C1=NN=NN1 UNZDSWVYQUPIEW-UHFFFAOYSA-N 0.000 claims 1
- NJYNSWOYMJGFSS-UHFFFAOYSA-N 3-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-1-methylsulfonylpiperidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1CCCN(S(C)(=O)=O)C1 NJYNSWOYMJGFSS-UHFFFAOYSA-N 0.000 claims 1
- VKXONMARJPWWGQ-UHFFFAOYSA-N 3-chloro-2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methoxy]-5-(trifluoromethyl)pyridine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1COC1=NC=C(C(F)(F)F)C=C1Cl VKXONMARJPWWGQ-UHFFFAOYSA-N 0.000 claims 1
- JNTFCOOPAXTOCX-UHFFFAOYSA-N 3-chloro-2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(Cl)C=CC=C1C(O)=O JNTFCOOPAXTOCX-UHFFFAOYSA-N 0.000 claims 1
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- RDXRVGJVCUAUMF-UHFFFAOYSA-N 3-chloro-4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=C(C(O)=O)C=C1Cl RDXRVGJVCUAUMF-UHFFFAOYSA-N 0.000 claims 1
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- ACQMKUAMPPWQJQ-UHFFFAOYSA-N 3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methoxy]-5-fluorobenzoic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(COC=3C(=CC(=CC=3F)C(O)=O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 ACQMKUAMPPWQJQ-UHFFFAOYSA-N 0.000 claims 1
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- VMGLZDSUADCJQV-UHFFFAOYSA-N 3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-n-[3-(diaminomethylideneamino)propyl]-5-fluorobenzamide Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(=O)NCCCNC(N)=N)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 VMGLZDSUADCJQV-UHFFFAOYSA-N 0.000 claims 1
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- CXJYZXVKUZQRTA-UHFFFAOYSA-N 3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-pyridin-3-ylimidazol-2-yl]sulfanylmethyl]-5-fluorobenzoic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(O)=O)Cl)=NC=2)C=2C=NC=CC=2)=C1 CXJYZXVKUZQRTA-UHFFFAOYSA-N 0.000 claims 1
- UVLBFNYWCLYWCA-UHFFFAOYSA-N 3-chloro-4-[[5-[2-(4-chloro-3-sulfamoylphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzoic acid Chemical compound C=1C=C(Cl)C(S(N)(=O)=O)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=C(C(O)=O)C=C1Cl UVLBFNYWCLYWCA-UHFFFAOYSA-N 0.000 claims 1
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- VYTHODSXYQZWIQ-UHFFFAOYSA-N 4-[2-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl VYTHODSXYQZWIQ-UHFFFAOYSA-N 0.000 claims 1
- COKQCJXBFYIOGO-UHFFFAOYSA-N 4-[2-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]benzene-1,2-diol Chemical compound C=1C=C(O)C(O)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl COKQCJXBFYIOGO-UHFFFAOYSA-N 0.000 claims 1
- UFLQDAOOWLQVNP-UHFFFAOYSA-N 4-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]benzene-1,2-diol Chemical compound C=1C=C(O)C(O)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl UFLQDAOOWLQVNP-UHFFFAOYSA-N 0.000 claims 1
- HNUYTSOUGOHKDZ-UHFFFAOYSA-N 4-[2-[2-chloro-5-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]ethyl]morpholine Chemical compound C=1C=C(Cl)C(OCCN2CCOCC2)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl HNUYTSOUGOHKDZ-UHFFFAOYSA-N 0.000 claims 1
- PXZMYCPOJLNONQ-UHFFFAOYSA-N 4-[2-[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]-2-fluoroethyl]-1-methylsulfonylpiperidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1C(F)CC1CCN(S(C)(=O)=O)CC1 PXZMYCPOJLNONQ-UHFFFAOYSA-N 0.000 claims 1
- NDYOYWJNQWLNFO-UHFFFAOYSA-N 4-[3-[2-chloro-5-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]propyl]morpholine Chemical compound C=1C=C(Cl)C(OCCCN2CCOCC2)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl NDYOYWJNQWLNFO-UHFFFAOYSA-N 0.000 claims 1
- TYDLPVRAPOELHZ-UHFFFAOYSA-N 4-[4-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazol-1-yl]phenyl]morpholine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(=CC=2)N2CCOCC2)=CN=C1SCC1=CC=C(F)C=C1Cl TYDLPVRAPOELHZ-UHFFFAOYSA-N 0.000 claims 1
- UCUZFLHGNGGHBE-UHFFFAOYSA-N 4-[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]-1-methylsulfonyl-3,6-dihydro-2h-pyridine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1C1=CCN(S(C)(=O)=O)CC1 UCUZFLHGNGGHBE-UHFFFAOYSA-N 0.000 claims 1
- PLNXQJZITSTREH-UHFFFAOYSA-N 4-[[1-(3,4-difluorophenyl)-5-[2-(4-methylsulfonylphenyl)propan-2-yl]imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoic acid Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(C)(C)C(N1C=2C=C(F)C(F)=CC=2)=CN=C1SCC1=C(F)C=C(C(O)=O)C=C1F PLNXQJZITSTREH-UHFFFAOYSA-N 0.000 claims 1
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- ZFGPWWPMYYVZHF-UHFFFAOYSA-N 4-[[1-(3-chloro-4-fluorophenyl)-5-[2-(3,4-dichlorophenyl)propan-2-yl]imidazol-2-yl]sulfanylmethyl]-1-methylsulfonylpiperidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=C(Cl)C(F)=CC=2)=CN=C1SCC1CCN(S(C)(=O)=O)CC1 ZFGPWWPMYYVZHF-UHFFFAOYSA-N 0.000 claims 1
- AFLSSVOUNOUOCE-UHFFFAOYSA-N 4-[[3-chloro-4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorobenzoyl]amino]butanoic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C(=O)NCCCC(O)=O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 AFLSSVOUNOUOCE-UHFFFAOYSA-N 0.000 claims 1
- YYHZNGNSTISRDT-UHFFFAOYSA-N 4-[[4-chloro-5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=C(Cl)N=C1SCC1=C(F)C=C(C(O)=O)C=C1F YYHZNGNSTISRDT-UHFFFAOYSA-N 0.000 claims 1
- MULSKRSMWGDWGO-UHFFFAOYSA-N 4-[[4-chloro-5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-1-(2h-tetrazol-5-yl)piperidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC3CCN(CC3)C=3NN=NN=3)=NC=2Cl)C=2C=CC(F)=CC=2)=C1 MULSKRSMWGDWGO-UHFFFAOYSA-N 0.000 claims 1
- NJEIIORODWFKLP-UHFFFAOYSA-N 4-[[4-chloro-5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-1-methylsulfonylpiperidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC3CCN(CC3)S(C)(=O)=O)=NC=2Cl)C=2C=CC(F)=CC=2)=C1 NJEIIORODWFKLP-UHFFFAOYSA-N 0.000 claims 1
- SHYVHQLHNIHEAA-UHFFFAOYSA-N 4-[[5-[1-(3,4-dichlorophenyl)cyclopropyl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoic acid Chemical compound FC1=CC(C(=O)O)=CC(F)=C1CSC1=NC=C(C2(CC2)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 SHYVHQLHNIHEAA-UHFFFAOYSA-N 0.000 claims 1
- ZPJLIYAHQAPVLP-UHFFFAOYSA-N 4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(3,4-difluorophenyl)imidazol-2-yl]sulfanylmethyl]-1-(2h-tetrazol-5-yl)piperidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=C(F)C(F)=CC=2)=CN=C1SCC(CC1)CCN1C1=NN=NN1 ZPJLIYAHQAPVLP-UHFFFAOYSA-N 0.000 claims 1
- KUFRRRJBXWWZNG-UHFFFAOYSA-N 4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(3,4-difluorophenyl)imidazol-2-yl]sulfanylmethyl]-1-methylsulfonylpiperidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=C(F)C(F)=CC=2)=CN=C1SCC1CCN(S(C)(=O)=O)CC1 KUFRRRJBXWWZNG-UHFFFAOYSA-N 0.000 claims 1
- LEMGEDNDBQKPJA-UHFFFAOYSA-N 4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-1-(2h-tetrazol-5-yl)piperidine Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC2CCN(CC2)C=2NN=NN=2)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)=C1 LEMGEDNDBQKPJA-UHFFFAOYSA-N 0.000 claims 1
- XVFRXYVMYCYHKD-UHFFFAOYSA-N 4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluoro-3-methoxyphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluoro-n-hydroxybenzamide Chemical compound C1=C(F)C(OC)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(=O)NO)F)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)=C1 XVFRXYVMYCYHKD-UHFFFAOYSA-N 0.000 claims 1
- PKOYVOPGDFSMBO-UHFFFAOYSA-N 4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluoro-3-methylphenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorobenzoic acid Chemical compound C1=C(F)C(C)=CC(N2C(=CN=C2SCC=2C(=CC(=CC=2F)C(O)=O)F)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)=C1 PKOYVOPGDFSMBO-UHFFFAOYSA-N 0.000 claims 1
- XHXVLEQLYSXBDV-UHFFFAOYSA-N 4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methoxy]-1-methylsulfonylpiperidine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1COC1CCN(S(C)(=O)=O)CC1 XHXVLEQLYSXBDV-UHFFFAOYSA-N 0.000 claims 1
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- CZYAABYYIJWCLN-UHFFFAOYSA-N 4-chloro-3-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC(C(O)=O)=CC=C1Cl CZYAABYYIJWCLN-UHFFFAOYSA-N 0.000 claims 1
- ISHTYFBATCFZIJ-UHFFFAOYSA-N 4-chloro-3-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzonitrile Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC(C#N)=CC=C1Cl ISHTYFBATCFZIJ-UHFFFAOYSA-N 0.000 claims 1
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- VHFUVDKCDJANBQ-UHFFFAOYSA-N 4-chloro-3-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]benzoic acid Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC=C(C=3)C(O)=O)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 VHFUVDKCDJANBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
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- LJCBURWSWVAMLL-UHFFFAOYSA-N 5-[4-[[5-[2-(3-chloro-4-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]-2h-tetrazole Chemical compound C1=C(Cl)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=C(F)C=C(C=2NN=NN=2)C=C1F LJCBURWSWVAMLL-UHFFFAOYSA-N 0.000 claims 1
- XWJWPZVBTQMWCU-UHFFFAOYSA-N 5-[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]-2h-tetrazole Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)C=3NN=NN=3)F)=NC=2)C=2C=CC(F)=CC=2)=C1 XWJWPZVBTQMWCU-UHFFFAOYSA-N 0.000 claims 1
- XOZGVZUGGMZYAT-UHFFFAOYSA-N 5-[4-chloro-3-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenyl]-2h-tetrazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC(C(=CC=1)Cl)=CC=1C1=NN=NN1 XOZGVZUGGMZYAT-UHFFFAOYSA-N 0.000 claims 1
- VOWCJQWUQHMFCI-UHFFFAOYSA-N 5-[5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenyl]-2h-tetrazole Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC(C=1)=CC=C(F)C=1C1=NN=NN1 VOWCJQWUQHMFCI-UHFFFAOYSA-N 0.000 claims 1
- NTRZALOZURZGSH-UHFFFAOYSA-N 5-[5-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenyl]-2h-tetrazole Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C=C(C(F)=CC=3)C=3NN=NN=3)=NC=2)C=2C=CC(F)=CC=2)=C1 NTRZALOZURZGSH-UHFFFAOYSA-N 0.000 claims 1
- HGLJOHAYSXTWFO-UHFFFAOYSA-N 5-[[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenoxy]methyl]-2h-tetrazole Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(OCC=4NN=NN=4)=CC=3F)F)=NC=2)C=2C=CC(F)=CC=2)=C1 HGLJOHAYSXTWFO-UHFFFAOYSA-N 0.000 claims 1
- OMYKWBUNJJMZSW-UHFFFAOYSA-N 5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorobenzenesulfonamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(S(N)(=O)=O)=C1 OMYKWBUNJJMZSW-UHFFFAOYSA-N 0.000 claims 1
- REUCSUAYSNORNK-UHFFFAOYSA-N 5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorobenzoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(C(O)=O)=C1 REUCSUAYSNORNK-UHFFFAOYSA-N 0.000 claims 1
- YUKDXIBTSAGQIO-UHFFFAOYSA-N 5-[[5-[2-(3,4-difluorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorobenzoic acid Chemical compound C=1C=C(F)C(F)=CC=1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(C(O)=O)=C1 YUKDXIBTSAGQIO-UHFFFAOYSA-N 0.000 claims 1
- MPVLSLFAYZXLKI-UHFFFAOYSA-N 5-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorobenzamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(C(N)=O)=C1 MPVLSLFAYZXLKI-UHFFFAOYSA-N 0.000 claims 1
- ZIQQBAHUANHHSB-UHFFFAOYSA-N 5-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorobenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(S(N)(=O)=O)=C1 ZIQQBAHUANHHSB-UHFFFAOYSA-N 0.000 claims 1
- PAHHUQUICKCURM-UHFFFAOYSA-N 5-[[5-[2-(3,5-dichloro-4-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorobenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=C(Cl)C=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(S(N)(=O)=O)=C1 PAHHUQUICKCURM-UHFFFAOYSA-N 0.000 claims 1
- TWSIGBRBVGTXMY-UHFFFAOYSA-N 5-[[5-[2-(3-chloro-4-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorobenzenesulfonamide Chemical compound C1=C(Cl)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C(S(N)(=O)=O)=C1 TWSIGBRBVGTXMY-UHFFFAOYSA-N 0.000 claims 1
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Images
Classifications
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15216309P | 2009-02-12 | 2009-02-12 | |
| US61/152,163 | 2009-02-12 | ||
| US28413909P | 2009-12-11 | 2009-12-11 | |
| US61/284,139 | 2009-12-11 | ||
| PCT/US2010/023981 WO2010093845A1 (en) | 2009-02-12 | 2010-02-12 | Triazole and imidazole derivatives for use as tgr5 agonists in the treatment of diabetes and obesity |
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| JP2014174935A Division JP2014240421A (ja) | 2009-02-12 | 2014-08-29 | 糖尿病および肥満の処置においてtgr5アゴニストとして使用するためのトリアゾールおよびイミダゾール誘導体 |
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| JP2012517479A true JP2012517479A (ja) | 2012-08-02 |
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| JP2014174935A Pending JP2014240421A (ja) | 2009-02-12 | 2014-08-29 | 糖尿病および肥満の処置においてtgr5アゴニストとして使用するためのトリアゾールおよびイミダゾール誘導体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2013513605A (ja) * | 2009-12-11 | 2013-04-22 | エグゼリクシス, インコーポレイテッド | Tgr5アゴニスト |
| JP2017517546A (ja) * | 2014-06-12 | 2017-06-29 | ユニヴェルシテ・ドゥ・リール・2・ドロワ・エ・サンテ | イミダゾール−または1,2,4−トリアゾール−誘導体及びその使用 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013513605A (ja) * | 2009-12-11 | 2013-04-22 | エグゼリクシス, インコーポレイテッド | Tgr5アゴニスト |
| JP2017517546A (ja) * | 2014-06-12 | 2017-06-29 | ユニヴェルシテ・ドゥ・リール・2・ドロワ・エ・サンテ | イミダゾール−または1,2,4−トリアゾール−誘導体及びその使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| AR075255A1 (es) | 2011-03-16 |
| KR20110119790A (ko) | 2011-11-02 |
| CN102395567A (zh) | 2012-03-28 |
| US20120040985A1 (en) | 2012-02-16 |
| WO2010093845A1 (en) | 2010-08-19 |
| TW201040168A (en) | 2010-11-16 |
| EP2396304A1 (en) | 2011-12-21 |
| JP2014240421A (ja) | 2014-12-25 |
| US8785488B2 (en) | 2014-07-22 |
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