JP2012517479A5 - - Google Patents
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- JP2012517479A5 JP2012517479A5 JP2011550244A JP2011550244A JP2012517479A5 JP 2012517479 A5 JP2012517479 A5 JP 2012517479A5 JP 2011550244 A JP2011550244 A JP 2011550244A JP 2011550244 A JP2011550244 A JP 2011550244A JP 2012517479 A5 JP2012517479 A5 JP 2012517479A5
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- JP
- Japan
- Prior art keywords
- fluorophenyl
- methyl
- methylethyl
- chloro
- thio
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 —CF 3 Chemical group 0.000 claims description 394
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 193
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 191
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 177
- 125000000217 alkyl group Chemical group 0.000 claims description 176
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 163
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 153
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 144
- 125000005843 halogen group Chemical group 0.000 claims description 142
- 229910052757 nitrogen Inorganic materials 0.000 claims description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 100
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 98
- 229910052799 carbon Inorganic materials 0.000 claims description 95
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 67
- 238000006467 substitution reaction Methods 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 22
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 20
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 20
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 102220065736 rs543286136 Human genes 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 13
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 13
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 10
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 229940124530 sulfonamide Drugs 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- VQTLPLINWFTECA-UHFFFAOYSA-N CC(C)(C(N1C(C=C2)=CC=C2F)=CN=C1SCC(C=CC=C1)=C1Cl)C(C=C1)=CC(Cl)=C1Cl Chemical compound CC(C)(C(N1C(C=C2)=CC=C2F)=CN=C1SCC(C=CC=C1)=C1Cl)C(C=C1)=CC(Cl)=C1Cl VQTLPLINWFTECA-UHFFFAOYSA-N 0.000 claims description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 6
- 229960003104 ornithine Drugs 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 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 4
- INHDNIUNHCQQAD-UHFFFAOYSA-N CC(C)(C1=CC(=C(C=C1)Cl)Cl)C2=CN=C(N2C3=CC=C(C=C3)F)SCC4=CC=C(C=C4)Cl Chemical compound CC(C)(C1=CC(=C(C=C1)Cl)Cl)C2=CN=C(N2C3=CC=C(C=C3)F)SCC4=CC=C(C=C4)Cl INHDNIUNHCQQAD-UHFFFAOYSA-N 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 229940125708 antidiabetic agent Drugs 0.000 claims description 4
- 239000003472 antidiabetic agent Substances 0.000 claims description 4
- 239000003613 bile acid Substances 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 230000004060 metabolic process Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 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 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 230000003914 insulin secretion Effects 0.000 claims description 3
- HVDYKSSIBZLYDN-UHFFFAOYSA-N 1-(2-chloro-4-fluorophenyl)-2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-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(F)=CC=2)Cl)=CN=C1SCC1=C(F)C=CC=C1Cl HVDYKSSIBZLYDN-UHFFFAOYSA-N 0.000 claims description 2
- GYPYJJOJXIHSES-UHFFFAOYSA-N 1-(2-chloro-4-fluorophenyl)-2-[(2-chloro-6-fluorophenyl)methylsulfonyl]-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(F)C=C1Cl GYPYJJOJXIHSES-UHFFFAOYSA-N 0.000 claims description 2
- RRBFQCDOMYYXTF-UHFFFAOYSA-N 1-(2-chloro-6-fluorophenyl)-n-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methyl]methanamine Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CNCC1=C(F)C=CC=C1Cl RRBFQCDOMYYXTF-UHFFFAOYSA-N 0.000 claims description 2
- GZEYVJFCYQHJIQ-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-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(F)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl GZEYVJFCYQHJIQ-UHFFFAOYSA-N 0.000 claims description 2
- LEYIGLQNENOYSM-UHFFFAOYSA-N 1-(4-chloro-2-fluorophenyl)-2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-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)F)=CN=C1SCC1=C(F)C=CC=C1Cl LEYIGLQNENOYSM-UHFFFAOYSA-N 0.000 claims description 2
- ODKLEAWFBFWPQQ-UHFFFAOYSA-N 1-(4-chloro-3-fluorophenyl)-2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-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(F)C(Cl)=CC=2)=CN=C1SCC1=C(F)C=CC=C1Cl ODKLEAWFBFWPQQ-UHFFFAOYSA-N 0.000 claims description 2
- NPNYOMRNTSQIAS-UHFFFAOYSA-N 1-(4-chloro-3-fluorophenyl)-n-[[5-[2-(3,4-dimethoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methyl]methanamine Chemical compound C1=C(OC)C(OC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1CNCC1=CC=C(Cl)C(F)=C1 NPNYOMRNTSQIAS-UHFFFAOYSA-N 0.000 claims description 2
- XCEMNMOXKNCJKP-UHFFFAOYSA-N 1-[2-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-5-fluorophenoxy]-2-methylpropan-2-ol Chemical compound CC(C)(O)COC1=CC(F)=CC=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 XCEMNMOXKNCJKP-UHFFFAOYSA-N 0.000 claims description 2
- BOXGSLKKHKIREO-UHFFFAOYSA-N 1-[2-chloro-4-[2-[2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]-2-methylpropan-2-ol Chemical compound C1=C(Cl)C(OCC(C)(O)C)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl BOXGSLKKHKIREO-UHFFFAOYSA-N 0.000 claims description 2
- XYYNQJPIODNIBN-UHFFFAOYSA-N 1-[2-chloro-4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1C(C(=C1)Cl)=CC=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 XYYNQJPIODNIBN-UHFFFAOYSA-N 0.000 claims description 2
- ZACNRBPGQRGGLV-UHFFFAOYSA-N 1-[2-chloro-5-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]-3-(4-fluorophenyl)imidazol-4-yl]propan-2-yl]phenoxy]-2-methylpropan-2-ol Chemical compound C1=C(Cl)C(OCC(C)(O)C)=CC(C(C)(C)C=2N(C(SCC=3C(=CC=CC=3F)Cl)=NC=2)C=2C=CC(F)=CC=2)=C1 ZACNRBPGQRGGLV-UHFFFAOYSA-N 0.000 claims description 2
- HOMYQEYBHVSUDR-UHFFFAOYSA-N 1-[3-chloro-4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]methoxy]phenyl]ethanone Chemical compound ClC1=CC(C(=O)C)=CC=C1OCC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 HOMYQEYBHVSUDR-UHFFFAOYSA-N 0.000 claims description 2
- BZSTYYMHJSMBAE-UHFFFAOYSA-N 1-[3-chloro-4-[[5-[2-[3-chloro-4-(methylsulfamoyl)phenyl]propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]phenyl]sulfonyl-3-pyrrolidin-1-ylurea Chemical compound C1=C(Cl)C(S(=O)(=O)NC)=CC=C1C(C)(C)C(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(S(=O)(=O)NC(=O)NN2CCCC2)C=C1Cl BZSTYYMHJSMBAE-UHFFFAOYSA-N 0.000 claims description 2
- DUFFJFASBHNCEO-UHFFFAOYSA-N 1-[4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC=C1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 DUFFJFASBHNCEO-UHFFFAOYSA-N 0.000 claims description 2
- VBWMQLGPUZINCJ-UHFFFAOYSA-N 1-[4-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1CSC1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 VBWMQLGPUZINCJ-UHFFFAOYSA-N 0.000 claims description 2
- VSHOWLFOHHRDOG-UHFFFAOYSA-N 1-[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfonyl-6-fluoro-2-methyl-3,4-dihydro-2h-quinoline Chemical compound CC1CCC2=CC(F)=CC=C2N1S(=O)(=O)C1=NC=C(C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)N1C1=CC=C(F)C=C1 VSHOWLFOHHRDOG-UHFFFAOYSA-N 0.000 claims description 2
- KPPQCSOLRHMOFN-UHFFFAOYSA-N 1-[5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenoxy]-2-methylpropan-2-ol Chemical compound C1=C(F)C(OCC(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 KPPQCSOLRHMOFN-UHFFFAOYSA-N 0.000 claims description 2
- WAGXGDNOEZCWLI-UHFFFAOYSA-N 1-[5-[[5-[2-(3,4-dichlorophenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-2-fluorophenyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1C1=CC(CSC=2N(C(=CN=2)C(C)(C)C=2C=C(Cl)C(Cl)=CC=2)C=2C=CC(F)=CC=2)=CC=C1F WAGXGDNOEZCWLI-UHFFFAOYSA-N 0.000 claims description 2
- DLIDYEMXMOHYCN-UHFFFAOYSA-N 2-[(2,4-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=C1Cl DLIDYEMXMOHYCN-UHFFFAOYSA-N 0.000 claims description 2
- DCWOAPVNFZVLDV-UHFFFAOYSA-N 2-[(2,4-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(=CC(Cl)=CC=2)Cl)N1C1=CC=C(F)C=C1 DCWOAPVNFZVLDV-UHFFFAOYSA-N 0.000 claims description 2
- YABSDWKXWYBGQE-UHFFFAOYSA-N 2-[(2,5-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(=CC=C(Cl)C=2)Cl)N1C1=CC=C(F)C=C1 YABSDWKXWYBGQE-UHFFFAOYSA-N 0.000 claims description 2
- FUAQVPOCGSYKLE-UHFFFAOYSA-N 2-[(2,6-dichlorophenyl)methylsulfanyl]-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=C1SCC1=C(Cl)C=CC=C1Cl FUAQVPOCGSYKLE-UHFFFAOYSA-N 0.000 claims description 2
- YBNPMYXRBZGVIR-UHFFFAOYSA-N 2-[(2,6-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=C(Cl)C=CC=C1Cl YBNPMYXRBZGVIR-UHFFFAOYSA-N 0.000 claims description 2
- DROPBSXDWDFZHL-UHFFFAOYSA-N 2-[(2-chloro-4-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=CC=C(F)C=C1Cl DROPBSXDWDFZHL-UHFFFAOYSA-N 0.000 claims description 2
- QBOFYCZNCOQNGC-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methoxymethyl]-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=C1COCC1=CC=C(F)C=C1Cl QBOFYCZNCOQNGC-UHFFFAOYSA-N 0.000 claims description 2
- TUNYHUCXSAVZIF-UHFFFAOYSA-N 2-[(2-chloro-4-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=CC=C(F)C=C1Cl TUNYHUCXSAVZIF-UHFFFAOYSA-N 0.000 claims description 2
- JHWSDZBSTMGCNL-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-5-[(3,4-difluorophenyl)methyl]-1-(4-fluorophenyl)imidazole Chemical compound C1=CC(F)=CC=C1N1C(SCC=2C(=CC(F)=CC=2)Cl)=NC=C1CC1=CC=C(F)C(F)=C1 JHWSDZBSTMGCNL-UHFFFAOYSA-N 0.000 claims description 2
- LGJAZZSZIFREGM-UHFFFAOYSA-N 2-[(2-chloro-4-fluorophenyl)methylsulfanyl]-5-[(3,4-dimethoxyphenyl)methyl]-1-(4-fluorophenyl)imidazole Chemical compound C1=C(OC)C(OC)=CC=C1CC(N1C=2C=CC(F)=CC=2)=CN=C1SCC1=CC=C(F)C=C1Cl LGJAZZSZIFREGM-UHFFFAOYSA-N 0.000 claims description 2
- ZGHYRINNSLFIJE-UHFFFAOYSA-N 2-[(2-chloro-4-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=CC=C(F)C=C1Cl ZGHYRINNSLFIJE-UHFFFAOYSA-N 0.000 claims description 2
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- 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 description 2
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- 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 description 2
- 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 description 2
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- 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 description 2
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- 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 description 2
- 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 description 2
- 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 description 2
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- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- GOJFHAKNGPPNHS-UHFFFAOYSA-N 2-[3-[[4-[[5-[2-(4-chloro-3-methoxyphenyl)propan-2-yl]-1-(4-fluorophenyl)imidazol-2-yl]sulfanylmethyl]-3,5-difluorophenyl]sulfonylamino]propyl]guanidine Chemical compound C1=C(Cl)C(OC)=CC(C(C)(C)C=2N(C(SCC=3C(=CC(=CC=3F)S(=O)(=O)NCCCNC(N)=N)F)=NC=2)C=2C=CC(F)=CC=2)=C1 GOJFHAKNGPPNHS-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- 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 description 2
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| WO2011133595A1 (en) | 2010-04-19 | 2011-10-27 | Massachusetts Institute Of Technology | A polymer-nanostructure composition for selective molecular recognition |
| EA201270778A1 (ru) | 2010-05-06 | 2013-04-30 | Бристол-Майерс Сквибб Компани | Бициклические гетероарильные аналоги в качестве модуляторов рецептора gpr119 |
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-
2010
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- 2010-02-12 AR ARP100100417A patent/AR075255A1/es not_active Application Discontinuation
- 2010-02-12 KR KR1020117021128A patent/KR20110119790A/ko not_active Withdrawn
- 2010-02-12 EP EP10704701A patent/EP2396304A1/en not_active Withdrawn
- 2010-02-12 CN CN2010800163259A patent/CN102395567A/zh active Pending
- 2010-02-12 TW TW099104908A patent/TW201040168A/zh unknown
- 2010-02-12 WO PCT/US2010/023981 patent/WO2010093845A1/en not_active Ceased
- 2010-02-12 US US13/148,811 patent/US8785488B2/en active Active
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2014
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