JP2008513508A5 - - Google Patents
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- JP2008513508A5 JP2008513508A5 JP2007532665A JP2007532665A JP2008513508A5 JP 2008513508 A5 JP2008513508 A5 JP 2008513508A5 JP 2007532665 A JP2007532665 A JP 2007532665A JP 2007532665 A JP2007532665 A JP 2007532665A JP 2008513508 A5 JP2008513508 A5 JP 2008513508A5
- Authority
- JP
- Japan
- Prior art keywords
- substituent
- phenyl
- benzimidazol
- trifluoromethyl
- benzamide
- 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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- 125000001424 substituent group Chemical group 0.000 claims 493
- 125000000217 alkyl group Chemical group 0.000 claims 108
- 125000003710 aryl alkyl group Chemical group 0.000 claims 78
- 125000001072 heteroaryl group Chemical group 0.000 claims 65
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 57
- 125000000623 heterocyclic group Chemical group 0.000 claims 57
- 125000003342 alkenyl group Chemical group 0.000 claims 56
- -1 imidazo [4,5-b] pyridyl Chemical group 0.000 claims 50
- 125000003118 aryl group Chemical group 0.000 claims 45
- 125000000304 alkynyl group Chemical group 0.000 claims 42
- 150000001875 compounds Chemical class 0.000 claims 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims 33
- 125000001188 haloalkyl group Chemical group 0.000 claims 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims 23
- 125000005843 halogen group Chemical group 0.000 claims 23
- 238000000034 method Methods 0.000 claims 22
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 21
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 15
- 229940002612 prodrug Drugs 0.000 claims 14
- 239000000651 prodrug Substances 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 239000012453 solvate Substances 0.000 claims 14
- 150000001204 N-oxides Chemical class 0.000 claims 12
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 12
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 12
- 125000003107 substituted aryl group Chemical group 0.000 claims 12
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 12
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 8
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 210000004027 cell Anatomy 0.000 claims 5
- JXQTVHIQYHIKJV-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-(trifluoromethyl)-5,6,7,8-tetrahydroindolizin-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2N3CCCCC3=CC=2C(F)(F)F)=C1F JXQTVHIQYHIKJV-UHFFFAOYSA-N 0.000 claims 4
- RDLXPCACGCVSPE-UHFFFAOYSA-N 3,5-dichloro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC(Cl)=CC(Cl)=C1 RDLXPCACGCVSPE-UHFFFAOYSA-N 0.000 claims 4
- 102000004310 Ion Channels Human genes 0.000 claims 4
- 108090000862 Ion Channels Proteins 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- NYZSHNWJMOVYHJ-UHFFFAOYSA-N n-[(2,6-difluorophenyl)methyl]-4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]aniline Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NCC1=C(F)C=CC=C1F NYZSHNWJMOVYHJ-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 4
- 230000001363 autoimmune Effects 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 210000002865 immune cell Anatomy 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- NDHILZHKJYRCNN-UHFFFAOYSA-N 1-(2,5-difluorophenyl)-3-[4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]urea Chemical compound FC1=CC=C(F)C(NC(=O)NC=2C=CC(=CC=2)N2C3=CC=CC=C3N=C2C(F)(F)F)=C1 NDHILZHKJYRCNN-UHFFFAOYSA-N 0.000 claims 2
- GVBBXQKANCRVLH-UHFFFAOYSA-N 1-(2,5-difluorophenyl)-3-[6-[2-(trifluoromethyl)benzimidazol-1-yl]pyridin-3-yl]thiourea Chemical compound FC1=CC=C(F)C(NC(=S)NC=2C=NC(=CC=2)N2C3=CC=CC=C3N=C2C(F)(F)F)=C1 GVBBXQKANCRVLH-UHFFFAOYSA-N 0.000 claims 2
- LZOPTSHTAYYRSR-UHFFFAOYSA-N 2,3,4,5,6-pentafluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F LZOPTSHTAYYRSR-UHFFFAOYSA-N 0.000 claims 2
- XNVIGFYIEMIGKA-UHFFFAOYSA-N 2,3,4,5-tetrafluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(F)C(F)=C1F XNVIGFYIEMIGKA-UHFFFAOYSA-N 0.000 claims 2
- GICUSOPCJYWPHT-UHFFFAOYSA-N 2,3,4-trifluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=C(F)C(F)=C1F GICUSOPCJYWPHT-UHFFFAOYSA-N 0.000 claims 2
- QVFINXWCWBWOIK-UHFFFAOYSA-N 2,3,5-trifluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC(F)=CC(F)=C1F QVFINXWCWBWOIK-UHFFFAOYSA-N 0.000 claims 2
- YQNHUFQCSKLAQP-UHFFFAOYSA-N 2,3,6-trifluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC(F)=C1F YQNHUFQCSKLAQP-UHFFFAOYSA-N 0.000 claims 2
- YAORPEGMKMDMRA-UHFFFAOYSA-N 2,3-dichloro-n-[4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(Cl)=C1Cl YAORPEGMKMDMRA-UHFFFAOYSA-N 0.000 claims 2
- DZMKYTWSNMTCKO-UHFFFAOYSA-N 2,3-difluoro-n-[2-[2-(trifluoromethyl)benzimidazol-1-yl]pyridin-3-yl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C(=NC=CC=2)N2C3=CC=CC=C3N=C2C(F)(F)F)=C1F DZMKYTWSNMTCKO-UHFFFAOYSA-N 0.000 claims 2
- SJYDPDQXLCEMTM-UHFFFAOYSA-N 2,3-difluoro-n-[2-methyl-4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound CC1=CC(N2C3=CC=CC=C3N=C2C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(F)=C1F SJYDPDQXLCEMTM-UHFFFAOYSA-N 0.000 claims 2
- USHXWCFLWKHXCT-UHFFFAOYSA-N 2,3-difluoro-n-[3-methyl-4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound C=1C=C(N2C3=CC=CC=C3N=C2C(F)(F)F)C(C)=CC=1NC(=O)C1=CC=CC(F)=C1F USHXWCFLWKHXCT-UHFFFAOYSA-N 0.000 claims 2
- WLTVMYFIMILLEK-UHFFFAOYSA-N 2,3-difluoro-n-[4-(2-iodobenzimidazol-1-yl)phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)N2C3=CC=CC=C3N=C2I)=C1F WLTVMYFIMILLEK-UHFFFAOYSA-N 0.000 claims 2
- BNWFPUUMEPWACP-UHFFFAOYSA-N 2,3-difluoro-n-[4-(2-methylbenzimidazol-1-yl)phenyl]benzamide Chemical compound CC1=NC2=CC=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F BNWFPUUMEPWACP-UHFFFAOYSA-N 0.000 claims 2
- ZLXZGMSSHOAYQU-UHFFFAOYSA-N 2,3-difluoro-n-[4-(2-methylsulfanylbenzimidazol-1-yl)phenyl]benzamide Chemical compound CSC1=NC2=CC=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F ZLXZGMSSHOAYQU-UHFFFAOYSA-N 0.000 claims 2
- CABLTRGIQPFHIH-UHFFFAOYSA-N 2,3-difluoro-n-[4-(2-methylsulfinylbenzimidazol-1-yl)phenyl]benzamide Chemical compound CS(=O)C1=NC2=CC=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F CABLTRGIQPFHIH-UHFFFAOYSA-N 0.000 claims 2
- OHCMLEBTCDKRNK-UHFFFAOYSA-N 2,3-difluoro-n-[4-(2-propan-2-ylbenzimidazol-1-yl)phenyl]benzamide Chemical compound CC(C)C1=NC2=CC=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F OHCMLEBTCDKRNK-UHFFFAOYSA-N 0.000 claims 2
- BIQYZPDBEJUQGM-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzenecarbothioamide Chemical compound FC1=CC=CC(C(=S)NC=2C=CC(=CC=2)N2C3=CC=CC=C3N=C2C(F)(F)F)=C1F BIQYZPDBEJUQGM-UHFFFAOYSA-N 0.000 claims 2
- AQUYHDDKQMGPMS-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=CC(=CC=2)N2C3=CC=CC=C3N=C2C(F)(F)F)=C1F AQUYHDDKQMGPMS-UHFFFAOYSA-N 0.000 claims 2
- UUQRYBZFXIXZPR-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)C=2N3C=CC=CC3=NC=2C(F)(F)F)=C1F UUQRYBZFXIXZPR-UHFFFAOYSA-N 0.000 claims 2
- YDVJLKAAQWIUBE-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-(trifluoromethyl)imidazo[4,5-b]pyridin-3-yl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)N2C3=NC=CC=C3N=C2C(F)(F)F)=C1F YDVJLKAAQWIUBE-UHFFFAOYSA-N 0.000 claims 2
- KXEPQFRTQMIREX-UHFFFAOYSA-N 2,3-difluoro-n-[4-[2-(trifluoromethyl)imidazo[4,5-c]pyridin-1-yl]phenyl]benzamide Chemical compound FC1=CC=CC(C(=O)NC=2C=CC(=CC=2)N2C3=CC=NC=C3N=C2C(F)(F)F)=C1F KXEPQFRTQMIREX-UHFFFAOYSA-N 0.000 claims 2
- ADJJXDPCIXFJKO-UHFFFAOYSA-N 2,3-difluoro-n-[4-[5-hydroxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(O)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F ADJJXDPCIXFJKO-UHFFFAOYSA-N 0.000 claims 2
- IJASKOMAOIVHIT-UHFFFAOYSA-N 2,3-difluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F IJASKOMAOIVHIT-UHFFFAOYSA-N 0.000 claims 2
- AZKCDWJDXNFRFR-UHFFFAOYSA-N 2,3-difluoro-n-[4-[5-methylsulfonyl-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(S(=O)(=O)C)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F AZKCDWJDXNFRFR-UHFFFAOYSA-N 0.000 claims 2
- XUPJMGITIFTAHP-UHFFFAOYSA-N 2,3-difluoro-n-[4-[6-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound C12=CC(OC)=CC=C2N=C(C(F)(F)F)N1C(C=C1)=CC=C1NC(=O)C1=CC=CC(F)=C1F XUPJMGITIFTAHP-UHFFFAOYSA-N 0.000 claims 2
- RSZDQZYUWZZSBT-UHFFFAOYSA-N 2,4,6-trichloro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=C(Cl)C=C1Cl RSZDQZYUWZZSBT-UHFFFAOYSA-N 0.000 claims 2
- JLXUMJXSSXGGLJ-UHFFFAOYSA-N 2,4-dichloro-5-fluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC(F)=C(Cl)C=C1Cl JLXUMJXSSXGGLJ-UHFFFAOYSA-N 0.000 claims 2
- WTZBHFYQOCSDGG-UHFFFAOYSA-N 2,4-difluoro-n-[4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC1=CC(F)=CC=C1C(=O)NC1=CC=C(N2C3=CC=CC=C3N=C2C(F)(F)F)C=C1 WTZBHFYQOCSDGG-UHFFFAOYSA-N 0.000 claims 2
- IDSYGRUNOOYCMV-UHFFFAOYSA-N 2,4-difluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=C(F)C=C1F IDSYGRUNOOYCMV-UHFFFAOYSA-N 0.000 claims 2
- IKKTUYBOEPABSN-UHFFFAOYSA-N 2,5-difluoro-n-[4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC1=CC=C(F)C(C(=O)NC=2C=CC(=CC=2)N2C3=CC=CC=C3N=C2C(F)(F)F)=C1 IKKTUYBOEPABSN-UHFFFAOYSA-N 0.000 claims 2
- STWIJCLVZQFIDV-UHFFFAOYSA-N 2,5-difluoro-n-[4-[2-(trifluoromethyl)imidazo[4,5-b]pyridin-3-yl]phenyl]benzamide Chemical compound FC1=CC=C(F)C(C(=O)NC=2C=CC(=CC=2)N2C3=NC=CC=C3N=C2C(F)(F)F)=C1 STWIJCLVZQFIDV-UHFFFAOYSA-N 0.000 claims 2
- IWWVMQDFYQWEQQ-UHFFFAOYSA-N 2,5-difluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC(F)=CC=C1F IWWVMQDFYQWEQQ-UHFFFAOYSA-N 0.000 claims 2
- IOLCOEXDLYSMMH-UHFFFAOYSA-N 2,5-difluoro-n-[6-[2-(trifluoromethyl)benzimidazol-1-yl]pyridin-3-yl]benzamide Chemical compound FC1=CC=C(F)C(C(=O)NC=2C=NC(=CC=2)N2C3=CC=CC=C3N=C2C(F)(F)F)=C1 IOLCOEXDLYSMMH-UHFFFAOYSA-N 0.000 claims 2
- WJONHQVDSQWGHO-UHFFFAOYSA-N 2,5-dimethoxy-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound COC1=CC=C(OC)C(C(=O)NC=2C=CC(=CC=2)N2C3=CC=C(OC)C=C3N=C2C(F)(F)F)=C1 WJONHQVDSQWGHO-UHFFFAOYSA-N 0.000 claims 2
- WNJOWINYIFIHOJ-UHFFFAOYSA-N 2,6-dichloro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=C(Cl)C=CC=C1Cl WNJOWINYIFIHOJ-UHFFFAOYSA-N 0.000 claims 2
- USRRTEKABQQVHS-UHFFFAOYSA-N 2,6-difluoro-3-iodo-n-[4-(5-methoxybenzimidazol-1-yl)phenyl]benzamide Chemical compound C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC(I)=C1F USRRTEKABQQVHS-UHFFFAOYSA-N 0.000 claims 2
- BCLYFBJNROCIER-UHFFFAOYSA-N 2,6-difluoro-3-iodo-n-[4-(7-methoxy-5,6,7,8-tetrahydroindolizin-3-yl)phenyl]benzamide Chemical compound C1C(OC)CCN2C1=CC=C2C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC(I)=C1F BCLYFBJNROCIER-UHFFFAOYSA-N 0.000 claims 2
- ASWDNJQDLYNLJP-UHFFFAOYSA-N 2,6-difluoro-3-iodo-n-[4-(7-methoxyimidazo[1,2-a]pyridin-3-yl)phenyl]benzamide Chemical compound C=1N=C2C=C(OC)C=CN2C=1C(C=C1)=CC=C1NC(=O)C1=C(F)C=CC(I)=C1F ASWDNJQDLYNLJP-UHFFFAOYSA-N 0.000 claims 2
- LHHBWOICJSOJHZ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC=C(N2C3=CC=C(OC)C=C3N=C2C(F)(F)F)C=C1 LHHBWOICJSOJHZ-UHFFFAOYSA-N 0.000 claims 2
- CBIFSJNERXQRQW-UHFFFAOYSA-N 2-bromo-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1Br CBIFSJNERXQRQW-UHFFFAOYSA-N 0.000 claims 2
- HRUVLMPXLGXCGM-UHFFFAOYSA-N 2-chloro-n-[4-(5-methoxybenzimidazol-1-yl)phenyl]benzamide Chemical compound C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1Cl HRUVLMPXLGXCGM-UHFFFAOYSA-N 0.000 claims 2
- IHMMICRQERCDJR-UHFFFAOYSA-N 2-chloro-n-[4-(7-methoxy-5,6,7,8-tetrahydroindolizin-3-yl)phenyl]benzamide Chemical compound C1C(OC)CCN2C1=CC=C2C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1Cl IHMMICRQERCDJR-UHFFFAOYSA-N 0.000 claims 2
- FZBMTGURFDLPDN-UHFFFAOYSA-N 2-chloro-n-[4-(7-methoxyimidazo[1,2-a]pyridin-3-yl)phenyl]benzamide Chemical compound C=1N=C2C=C(OC)C=CN2C=1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1Cl FZBMTGURFDLPDN-UHFFFAOYSA-N 0.000 claims 2
- SXQPAHAFCYNFLY-UHFFFAOYSA-N 2-chloro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1Cl SXQPAHAFCYNFLY-UHFFFAOYSA-N 0.000 claims 2
- NOCCHZQVBIVCQW-UHFFFAOYSA-N 2-ethyl-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]hexanamide Chemical compound C1=CC(NC(=O)C(CC)CCCC)=CC=C1N1C2=CC=C(OC)C=C2N=C1C(F)(F)F NOCCHZQVBIVCQW-UHFFFAOYSA-N 0.000 claims 2
- NFDPCECSLSDDDY-UHFFFAOYSA-N 2-fluoro-n-[4-(5-methoxybenzimidazol-1-yl)phenyl]pyridine-4-carboxamide Chemical compound C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=NC(F)=C1 NFDPCECSLSDDDY-UHFFFAOYSA-N 0.000 claims 2
- GJEVIIPAENUIBN-UHFFFAOYSA-N 2-iodo-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1I GJEVIIPAENUIBN-UHFFFAOYSA-N 0.000 claims 2
- STYFOCUGOOYSHW-UHFFFAOYSA-N 2-methoxy-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1OC STYFOCUGOOYSHW-UHFFFAOYSA-N 0.000 claims 2
- NVVCPKOGHZWTJA-UHFFFAOYSA-N 2-methyl-n-[4-[2-(trifluoromethyl)-5,6,7,8-tetrahydroindolizin-3-yl]phenyl]benzamide Chemical compound CC1=CC=CC=C1C(=O)NC1=CC=C(C=2N3CCCCC3=CC=2C(F)(F)F)C=C1 NVVCPKOGHZWTJA-UHFFFAOYSA-N 0.000 claims 2
- WTKDONGBLLBOCY-UHFFFAOYSA-N 3,4-difluoro-n-[4-[5-methoxy-2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound FC(F)(F)C1=NC2=CC(OC)=CC=C2N1C(C=C1)=CC=C1NC(=O)C1=CC=C(F)C(F)=C1 WTKDONGBLLBOCY-UHFFFAOYSA-N 0.000 claims 2
- OWCSBRYQRKXOIM-UHFFFAOYSA-N 3-amino-2,5,6-trifluoro-n-[4-[2-(trifluoromethyl)benzimidazol-1-yl]phenyl]benzamide Chemical compound NC1=CC(F)=C(F)C(C(=O)NC=2C=CC(=CC=2)N2C3=CC=CC=C3N=C2C(F)(F)F)=C1F OWCSBRYQRKXOIM-UHFFFAOYSA-N 0.000 claims 2
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2005
- 2005-09-21 KR KR1020077008930A patent/KR20070057965A/ko not_active Withdrawn
- 2005-09-21 MX MX2007003342A patent/MX2007003342A/es not_active Application Discontinuation
- 2005-09-21 EP EP05814906A patent/EP1809294A4/en not_active Withdrawn
- 2005-09-21 BR BRPI0515546-0A patent/BRPI0515546A/pt not_active IP Right Cessation
- 2005-09-21 CA CA002580852A patent/CA2580852A1/en not_active Abandoned
- 2005-09-21 WO PCT/US2005/033980 patent/WO2006034402A2/en not_active Ceased
- 2005-09-21 US US11/233,224 patent/US7709518B2/en not_active Expired - Fee Related
- 2005-09-21 TW TW094132617A patent/TW200621232A/zh unknown
- 2005-09-21 JP JP2007532665A patent/JP2008513508A/ja active Pending
- 2005-09-21 CN CNA200580038882XA patent/CN101083985A/zh active Pending
- 2005-09-21 AU AU2005286701A patent/AU2005286701A1/en not_active Abandoned
-
2007
- 2007-03-19 IL IL182025A patent/IL182025A0/en unknown
- 2007-03-20 ZA ZA200702350A patent/ZA200702350B/xx unknown
-
2010
- 2010-03-05 US US12/718,366 patent/US8314134B2/en not_active Expired - Fee Related
-
2012
- 2012-10-16 US US13/652,878 patent/US8524756B2/en not_active Expired - Fee Related
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