JP2003515560A5 - - Google Patents
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- JP2003515560A5 JP2003515560A5 JP2001541505A JP2001541505A JP2003515560A5 JP 2003515560 A5 JP2003515560 A5 JP 2003515560A5 JP 2001541505 A JP2001541505 A JP 2001541505A JP 2001541505 A JP2001541505 A JP 2001541505A JP 2003515560 A5 JP2003515560 A5 JP 2003515560A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- naphtho
- imidazole
- sulfonic acid
- acid hydrochloride
- 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 N-sulfonylamino Chemical group 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 13
- ZNWDDQLLGMFOEE-UHFFFAOYSA-N 1h-imidazole-5-sulfonic acid;hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CN=CN1 ZNWDDQLLGMFOEE-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 6
- 125000000547 substituted alkyl group Chemical group 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- RIXQDZPQQARWPF-UHFFFAOYSA-N 2-[3-(3,4-dimethylphenyl)-4-fluorophenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=CC=C1F RIXQDZPQQARWPF-UHFFFAOYSA-N 0.000 description 2
- DHDPRFWMBZYBHQ-UHFFFAOYSA-N 2-[3-(4-tert-butylphenyl)-4-fluorophenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=CC=C1F DHDPRFWMBZYBHQ-UHFFFAOYSA-N 0.000 description 2
- UUCZHGTVNCOOGT-UHFFFAOYSA-N 2-[3-(4-tert-butylphenyl)-4-methoxyphenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound COC1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)C=C1C1=CC=C(C(C)(C)C)C=C1 UUCZHGTVNCOOGT-UHFFFAOYSA-N 0.000 description 2
- JUTHBNVXQXOKAW-UHFFFAOYSA-N 2-[4-(3,4-dimethylphenyl)thiophen-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CSC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 JUTHBNVXQXOKAW-UHFFFAOYSA-N 0.000 description 2
- YUYKKHRGDBTSCO-UHFFFAOYSA-N 2-[4-(4-tert-butylphenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=COC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 YUYKKHRGDBTSCO-UHFFFAOYSA-N 0.000 description 2
- JRQVQXMCEHOMTD-UHFFFAOYSA-N 2-[4-(4-tert-butylphenyl)thiophen-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CSC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 JRQVQXMCEHOMTD-UHFFFAOYSA-N 0.000 description 2
- JGVUAKWZVVQDIZ-UHFFFAOYSA-N 2-[5-(1-benzothiophen-2-yl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC=C2SC(C3=CC=C(O3)C3=NC=4C5=C(O)C=C(C=C5C=CC=4N3)C(=O)O)=CC2=C1 JGVUAKWZVVQDIZ-UHFFFAOYSA-N 0.000 description 2
- BVFJXHBESHGUAG-UHFFFAOYSA-N 2-[5-(3,4-dichlorophenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(O1)=CC=C1C1=CC=C(Cl)C(Cl)=C1 BVFJXHBESHGUAG-UHFFFAOYSA-N 0.000 description 2
- MRINVXQHKAFPJM-UHFFFAOYSA-N 2-[5-(3,4-dimethylphenyl)-2-fluorophenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=C(F)C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 MRINVXQHKAFPJM-UHFFFAOYSA-N 0.000 description 2
- NBZHPHMNNFTTGT-UHFFFAOYSA-N 2-[5-(3,4-dimethylphenyl)thiophen-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)S1 NBZHPHMNNFTTGT-UHFFFAOYSA-N 0.000 description 2
- BZFLTSNUYALYDP-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)-2-fluorophenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(F)C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 BZFLTSNUYALYDP-UHFFFAOYSA-N 0.000 description 2
- AFIXYXZIEDFJSQ-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)O1 AFIXYXZIEDFJSQ-UHFFFAOYSA-N 0.000 description 2
- FZUAAPXAGQKWTR-UHFFFAOYSA-N 9-hydroxy-2-[3-[4-(trifluoromethyl)phenyl]phenyl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)C=C1 FZUAAPXAGQKWTR-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- GFVJZXBMFOFSQG-VWLOTQADSA-N (2s)-1-[2-[3-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(=O)N3[C@@H](CCC3)C(O)=O)N=2)=C1 GFVJZXBMFOFSQG-VWLOTQADSA-N 0.000 description 1
- IDFUAIXQXIJJAT-VWLOTQADSA-N (2s)-1-[[2-[3-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazol-7-yl]sulfonyl]pyrrolidine-2-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(=O)(=O)N3[C@@H](CCC3)C(O)=O)N=2)=C1 IDFUAIXQXIJJAT-VWLOTQADSA-N 0.000 description 1
- AGOPBTNYHFETNJ-VWLOTQADSA-N (2s)-2-[[2-[3-(4-tert-butylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carbonyl]amino]pentanedioic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N=2)=C1 AGOPBTNYHFETNJ-VWLOTQADSA-N 0.000 description 1
- WJRLZGRPVWMNFM-UHFFFAOYSA-N 1,4-difluoro-2-phenyl-5-(trifluoromethyl)benzene Chemical group FC1=CC(=C(F)C=C1C(F)(F)F)C1=CC=CC=C1 WJRLZGRPVWMNFM-UHFFFAOYSA-N 0.000 description 1
- FVEFQOZRXHWTHO-UHFFFAOYSA-N 1-[[2-[3-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazol-7-yl]sulfonyl]piperidine-3-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(=O)(=O)N3CC(CCC3)C(O)=O)N=2)=C1 FVEFQOZRXHWTHO-UHFFFAOYSA-N 0.000 description 1
- VBYPCJIAVPFBDO-UHFFFAOYSA-N 1-fluoro-4-[4-(trifluoromethyl)phenyl]benzene Chemical group C1=CC(F)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VBYPCJIAVPFBDO-UHFFFAOYSA-N 0.000 description 1
- HMYQKSCWAIVMPA-UHFFFAOYSA-N 2-[1-(4-tert-butylphenyl)pyrazol-4-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1N1N=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 HMYQKSCWAIVMPA-UHFFFAOYSA-N 0.000 description 1
- CCDYVLRMODKYBN-UHFFFAOYSA-N 2-[3-(3,4-difluorophenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(C=1)=CC=CC=1C1=CC=C(F)C(F)=C1 CCDYVLRMODKYBN-UHFFFAOYSA-N 0.000 description 1
- LWERZCYTAOCHIQ-UHFFFAOYSA-N 2-[3-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C)C(C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 LWERZCYTAOCHIQ-UHFFFAOYSA-N 0.000 description 1
- UHQHZVOLONUFDA-UHFFFAOYSA-N 2-[3-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-sulfonic acid;hydrochloride Chemical compound Cl.C1=C(C)C(C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(O)(=O)=O)N=2)=C1 UHQHZVOLONUFDA-UHFFFAOYSA-N 0.000 description 1
- YIGCYXIJBYEWHG-UHFFFAOYSA-N 2-[3-(4-carboxy-3-methylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=CC(C=2C=C(C=CC=2)C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 YIGCYXIJBYEWHG-UHFFFAOYSA-N 0.000 description 1
- MJOUJSVVDLUTNU-UHFFFAOYSA-N 2-[3-(4-cyano-3-methylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C#N)C(C)=CC(C=2C=C(C=CC=2)C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 MJOUJSVVDLUTNU-UHFFFAOYSA-N 0.000 description 1
- FMMBNUOLITXBJH-UHFFFAOYSA-N 2-[3-(4-ethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 FMMBNUOLITXBJH-UHFFFAOYSA-N 0.000 description 1
- WDPVPCHFYXVZBH-UHFFFAOYSA-N 2-[3-(4-fluoro-3-methylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(F)C(C)=CC(C=2C=C(C=CC=2)C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 WDPVPCHFYXVZBH-UHFFFAOYSA-N 0.000 description 1
- CEWMMRRJLMXMNM-UHFFFAOYSA-N 2-[3-(4-tert-butylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 CEWMMRRJLMXMNM-UHFFFAOYSA-N 0.000 description 1
- YFYUMMQGLANYIX-UHFFFAOYSA-N 2-[3-(4-tert-butylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-sulfonic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(O)(=O)=O)N=2)=C1 YFYUMMQGLANYIX-UHFFFAOYSA-N 0.000 description 1
- NLMFQHLOROEZBE-UHFFFAOYSA-N 2-[3-(9h-fluoren-2-yl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC(C2=NC=3C4=C(O)C=C(C=C4C=CC=3N2)C(=O)O)=CC=C1 NLMFQHLOROEZBE-UHFFFAOYSA-N 0.000 description 1
- YHPILCSUFYSKFW-UHFFFAOYSA-N 2-[3-[(3,4-dimethylphenyl)methoxy]phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-sulfonic acid;hydrochloride Chemical compound Cl.C1=C(C)C(C)=CC=C1COC1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(O)(=O)=O)N=2)=C1 YHPILCSUFYSKFW-UHFFFAOYSA-N 0.000 description 1
- KSEDNJCWTKBAAS-UHFFFAOYSA-N 2-[3-[(4-tert-butylphenyl)methoxy]phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-sulfonic acid;hydrochloride Chemical compound Cl.C1=CC(C(C)(C)C)=CC=C1COC1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(O)(=O)=O)N=2)=C1 KSEDNJCWTKBAAS-UHFFFAOYSA-N 0.000 description 1
- OTZGPXBQZJFLQX-UHFFFAOYSA-N 2-[4-(3,4-dimethylphenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=COC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 OTZGPXBQZJFLQX-UHFFFAOYSA-N 0.000 description 1
- KUOCSFZNWSSKNQ-UHFFFAOYSA-N 2-[4-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)C=C1 KUOCSFZNWSSKNQ-UHFFFAOYSA-N 0.000 description 1
- CANPVTDMCNTPJI-UHFFFAOYSA-N 2-[4-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazole-7-sulfonic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C)C(C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(O)(=O)=O)N=2)C=C1 CANPVTDMCNTPJI-UHFFFAOYSA-N 0.000 description 1
- URPRRKYQUKYLLB-UHFFFAOYSA-N 2-[5-(3,4-dimethylphenyl)furan-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)O1 URPRRKYQUKYLLB-UHFFFAOYSA-N 0.000 description 1
- AGWRYRHIQJXNLW-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)pyridin-3-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CN=CC(C=2NC3=C4C(O)=CC(=CC4=CC=C3N=2)C(O)=O)=C1 AGWRYRHIQJXNLW-UHFFFAOYSA-N 0.000 description 1
- IYUUWMOKXYWEKS-UHFFFAOYSA-N 2-[5-(4-tert-butylphenyl)thiophen-2-yl]-9-hydroxy-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)S1 IYUUWMOKXYWEKS-UHFFFAOYSA-N 0.000 description 1
- UFTVNMRVQIUXPU-UHFFFAOYSA-N 2-[6-(4-tert-butylphenyl)pyridin-2-yl]-9-hydroxy-3H-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=N1 UFTVNMRVQIUXPU-UHFFFAOYSA-N 0.000 description 1
- ITRBTOXCUXWGGG-UHFFFAOYSA-N 2-fluoro-1-phenyl-4-(trifluoromethyl)benzene Chemical group FC1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1 ITRBTOXCUXWGGG-UHFFFAOYSA-N 0.000 description 1
- YDDZHDBISXIDKD-UHFFFAOYSA-N 3-[[2-[3-(3,4-dimethylphenyl)phenyl]-9-hydroxy-3h-benzo[e]benzimidazol-7-yl]sulfonylamino]benzoic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(=O)(=O)NC=3C=C(C=CC=3)C(O)=O)N=2)=C1 YDDZHDBISXIDKD-UHFFFAOYSA-N 0.000 description 1
- AOWUASXGYDUMKM-UHFFFAOYSA-N 9-hydroxy-2-(1-hydroxynaphthalen-2-yl)-3H-benzo[e]benzimidazole-7-carboxylic acid 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.OC1=C(C=CC2=CC=CC=C12)C=1NC2=C(N1)C1=C(C=C(C=C1C=C2)C(=O)O)O AOWUASXGYDUMKM-UHFFFAOYSA-N 0.000 description 1
- CMYMIQFTYLXWST-UHFFFAOYSA-N 9-hydroxy-2-(2-hydroxy-3-phenylphenyl)-3H-benzo[e]benzimidazole-5-sulfonic acid hydrochloride Chemical compound Cl.N=1C2=C3C(O)=CC=CC3=C(S(O)(=O)=O)C=C2NC=1C(C=1O)=CC=CC=1C1=CC=CC=C1 CMYMIQFTYLXWST-UHFFFAOYSA-N 0.000 description 1
- BFCKDCLYXKVZNH-UHFFFAOYSA-N 9-hydroxy-2-(2-hydroxy-3-phenylphenyl)-3H-benzo[e]benzimidazole-7-sulfonic acid hydrochloride Chemical compound Cl.N=1C2=C3C(O)=CC(S(O)(=O)=O)=CC3=CC=C2NC=1C(C=1O)=CC=CC=1C1=CC=CC=C1 BFCKDCLYXKVZNH-UHFFFAOYSA-N 0.000 description 1
- WFDZKMZOMIEUGB-UHFFFAOYSA-N 9-hydroxy-2-(2-hydroxy-4-phenylphenyl)-3H-benzo[e]benzimidazole-5-sulfonic acid hydrochloride Chemical compound Cl.C=1C=C(C=2NC3=C(C4=C(O)C=CC=C4C(=C3)S(O)(=O)=O)N=2)C(O)=CC=1C1=CC=CC=C1 WFDZKMZOMIEUGB-UHFFFAOYSA-N 0.000 description 1
- HAJCDJMVUFSIEJ-UHFFFAOYSA-N 9-hydroxy-2-(2-hydroxy-4-phenylphenyl)-3H-benzo[e]benzimidazole-7-sulfonic acid hydrochloride Chemical compound Cl.C=1C=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(O)(=O)=O)N=2)C(O)=CC=1C1=CC=CC=C1 HAJCDJMVUFSIEJ-UHFFFAOYSA-N 0.000 description 1
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- VWIYXNRAXFAPGX-UHFFFAOYSA-N 9-hydroxy-2-(2-methoxy-3-phenylphenyl)-3h-benzo[e]benzimidazole-7-carboxylic acid;hydrochloride Chemical compound Cl.COC1=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)C=CC=C1C1=CC=CC=C1 VWIYXNRAXFAPGX-UHFFFAOYSA-N 0.000 description 1
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- RGXVDSGUPSHCBU-UHFFFAOYSA-N 9-hydroxy-2-(2-methoxy-4-phenylphenyl)-3h-benzo[e]benzimidazole-5-sulfonic acid;hydrochloride Chemical compound Cl.C=1C=C(C=2NC3=C(C4=C(O)C=CC=C4C(=C3)S(O)(=O)=O)N=2)C(OC)=CC=1C1=CC=CC=C1 RGXVDSGUPSHCBU-UHFFFAOYSA-N 0.000 description 1
- COUJBTBHGAIPTD-UHFFFAOYSA-N 9-hydroxy-2-(2-methoxy-4-phenylphenyl)-3h-benzo[e]benzimidazole-7-sulfonic acid;hydrochloride Chemical compound Cl.C=1C=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(O)(=O)=O)N=2)C(OC)=CC=1C1=CC=CC=C1 COUJBTBHGAIPTD-UHFFFAOYSA-N 0.000 description 1
- DXSQQJMOMUMDRZ-UHFFFAOYSA-N 9-hydroxy-2-(3-phenoxyphenyl)-3h-benzo[e]benzimidazole-7-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(C=1)=CC=CC=1OC1=CC=CC=C1 DXSQQJMOMUMDRZ-UHFFFAOYSA-N 0.000 description 1
- VYZIIAYKVGFVLA-UHFFFAOYSA-N 9-hydroxy-2-(4-phenylphenyl)-3h-benzo[e]benzimidazole-7-sulfonic acid;hydrochloride Chemical compound Cl.N=1C2=C3C(O)=CC(S(O)(=O)=O)=CC3=CC=C2NC=1C(C=C1)=CC=C1C1=CC=CC=C1 VYZIIAYKVGFVLA-UHFFFAOYSA-N 0.000 description 1
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- OIWAWOJRRRBLPH-UHFFFAOYSA-N 9-hydroxy-2-[3-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]-3h-benzo[e]benzimidazole-7-sulfonic acid;hydrochloride Chemical compound Cl.N=1C2=C3C(O)=CC(S(O)(=O)=O)=CC3=CC=C2NC=1C(C=1)=CC=CC=1OCC1=CC=CC(C(F)(F)F)=C1 OIWAWOJRRRBLPH-UHFFFAOYSA-N 0.000 description 1
- OFGYBOHAQNSGKW-UHFFFAOYSA-N 9-hydroxy-2-[4-[4-(trifluoromethyl)phenyl]thiophen-2-yl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(SC=1)=CC=1C1=CC=C(C(F)(F)F)C=C1 OFGYBOHAQNSGKW-UHFFFAOYSA-N 0.000 description 1
- PRRDCKYEDGCCLO-UHFFFAOYSA-N 9-hydroxy-2-[5-(3-propan-2-ylphenyl)furan-2-yl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound CC(C)C1=CC=CC(C=2OC(=CC=2)C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 PRRDCKYEDGCCLO-UHFFFAOYSA-N 0.000 description 1
- VHVGKHMMCSHNKO-UHFFFAOYSA-N 9-hydroxy-2-[5-[4-(trifluoromethyl)phenyl]furan-2-yl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound N1C=2C=CC3=CC(C(=O)O)=CC(O)=C3C=2N=C1C(O1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VHVGKHMMCSHNKO-UHFFFAOYSA-N 0.000 description 1
- SCEWJWDMGYCDCP-UHFFFAOYSA-N 9-hydroxy-2-pyridin-2-yl-3H-benzo[e]benzimidazole-7-carboxylic acid 2,2,2-trifluoroacetic acid Chemical compound FC(C(=O)O)(F)F.N1=C(C=CC=C1)C=1NC2=C(N1)C1=C(C=C(C=C1C=C2)C(=O)O)O SCEWJWDMGYCDCP-UHFFFAOYSA-N 0.000 description 1
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16913099P | 1999-12-06 | 1999-12-06 | |
| US60/169,130 | 1999-12-06 | ||
| PCT/US2000/033432 WO2001039773A1 (en) | 1999-12-06 | 2000-12-06 | Thrombopoietin mimetics |
Publications (2)
| Publication Number | Publication Date |
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| JP2003515560A JP2003515560A (ja) | 2003-05-07 |
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| JP (1) | JP2003515560A (enExample) |
| AT (1) | ATE344031T1 (enExample) |
| AU (1) | AU2079901A (enExample) |
| DE (1) | DE60031714T2 (enExample) |
| ES (1) | ES2275567T3 (enExample) |
| WO (1) | WO2001039773A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2495184A1 (en) | 2002-08-14 | 2004-02-26 | Nissan Chemical Industries, Ltd. | Thrombopoietin receptor activators and process for their production |
| TWI324593B (en) | 2002-10-09 | 2010-05-11 | Nissan Chemical Ind Ltd | Pyrazolone compounds and thrombopoietin receptor activator |
| CA2507707C (en) | 2002-12-03 | 2011-06-21 | Axys Pharmaceuticals, Inc. | 2-(2-hydroxybiphenyl-3-yl)-1h-benzoimidazole-5-carboxamidine derivatives as factor viia inhibitors |
| SI1569907T1 (sl) * | 2002-12-13 | 2016-06-30 | Ym Biosciences Australia Pty Ltd | Na nikotinamidu osnovani kinazni inhibitorji |
| JP2006514951A (ja) * | 2002-12-13 | 2006-05-18 | スミスクライン・ビーチャム・コーポレイション | トロンボポエチン模倣物 |
| TW200418791A (en) * | 2003-01-23 | 2004-10-01 | Bristol Myers Squibb Co | Pharmaceutical compositions for inhibiting proteasome |
| WO2005016862A1 (en) * | 2003-08-14 | 2005-02-24 | Asahi Kasei Pharma Corporation | Substituted arylalkanoic acid derivative and use thereof |
| US8729117B2 (en) | 2004-06-02 | 2014-05-20 | Pharmacyclics, Inc. | Factor VIIa inhibitor |
| WO2006062240A1 (en) | 2004-12-08 | 2006-06-15 | Nissan Chemical Industries, Ltd. | 3-ethylidenehydrazino substituted heterocyclic compounds as thrombopoietin receptor activators |
| KR101215207B1 (ko) | 2004-12-14 | 2012-12-26 | 닛산 가가쿠 고교 가부시키 가이샤 | 아미드 화합물 및 트롬보포이에틴 리셉터 활성화제 |
| PL1910338T3 (pl) * | 2005-07-14 | 2011-02-28 | Irm Llc | Związki heterotetracykliczne jako mimetyki TPO |
| NZ563202A (en) | 2005-07-15 | 2011-02-25 | Nissan Chemical Ind Ltd | Thiophene compounds and thrombopoietin receptor activators |
| JP5104752B2 (ja) | 2005-07-20 | 2012-12-19 | 日産化学工業株式会社 | ピラゾール化合物及びトロンボポエチンレセプター活性化剤 |
| EP1915341A2 (en) * | 2005-08-15 | 2008-04-30 | Irm, Llc | Compounds and compositions as tpo mimetics |
| JP5205967B2 (ja) | 2005-11-07 | 2013-06-05 | 日産化学工業株式会社 | ヒドラジド化合物及びトロンボポエチンレセプター活性化剤 |
| JP5157900B2 (ja) | 2006-06-07 | 2013-03-06 | 日産化学工業株式会社 | 含窒素ヘテロ環化合物及びトロンボポエチンレセプター活性化剤 |
| CA2656810C (en) | 2006-07-11 | 2012-03-13 | Daewoong Pharmaceutical Co., Ltd. | Biaryl benzoimidazole derivatives and pharmaceutical composition comprising the same |
| CA2685524A1 (en) | 2007-04-30 | 2008-11-06 | Abbott Laboratories | Inhibitors of diacylglycerol o-acyltransferase type 1 enzyme |
| CN101481352A (zh) | 2008-01-10 | 2009-07-15 | 上海恒瑞医药有限公司 | 双环取代吡唑酮偶氮类衍生物、其制备方法及其在医药上的应用 |
| PE20100362A1 (es) | 2008-10-30 | 2010-05-27 | Irm Llc | Derivados de purina que expanden las celulas madre hematopoyeticas |
| CN101921232A (zh) | 2009-06-11 | 2010-12-22 | 上海恒瑞医药有限公司 | 双环取代吡唑酮偶氮类衍生物的盐,其制备方法及其在医药上的应用 |
| WO2012102937A2 (en) | 2011-01-25 | 2012-08-02 | Irm Llc | Compounds that expand hematopoietic stem cells |
| EP2788476B1 (en) | 2011-12-08 | 2019-05-22 | Fred Hutchinson Cancer Research Center | Compositions and methods for enhanced generation of hematopoietic stem/progenitor cells |
| CN104144931B (zh) | 2012-01-27 | 2018-04-10 | 蒙特利尔大学 | 嘧啶并[4,5‑b]吲哚衍生物及其在造血干细胞的扩增中的应用 |
| CN111620870B (zh) | 2014-04-22 | 2023-01-03 | 蒙特利尔大学 | 化合物及其在扩增造血干细胞和/或造血祖细胞中的应用 |
| JP6658535B2 (ja) | 2014-10-31 | 2020-03-04 | 日産化学株式会社 | リガンド結合繊維及び当該繊維を用いた細胞培養基材 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE193350C (enExample) * | ||||
| US851444A (en) * | 1905-11-13 | 1907-04-23 | Agfa Ag | Amido-oxy-sulfonic acid of phenylnaphthimidazol and process of making same. |
| US4435417A (en) * | 1981-02-20 | 1984-03-06 | Gruppo Lepetit S.P.A. | Antiinflammatory 3H-naphtho[1,2-d]imidazoles |
| DE4126612A1 (de) * | 1990-08-14 | 1992-02-20 | Ciba Geigy Ag | Reaktivfarbstoffe, deren herstellung und verwendung |
| PT98673B (pt) * | 1990-08-15 | 1999-01-29 | British Bio Technology | Processo para a preparacao de compostos que sao antagonistas do factor de activacao de plaquetas por exemplo derivados de benzimidazole e de seus intermediarios |
-
2000
- 2000-12-06 JP JP2001541505A patent/JP2003515560A/ja active Pending
- 2000-12-06 AU AU20799/01A patent/AU2079901A/en not_active Abandoned
- 2000-12-06 AT AT00984123T patent/ATE344031T1/de not_active IP Right Cessation
- 2000-12-06 DE DE60031714T patent/DE60031714T2/de not_active Expired - Fee Related
- 2000-12-06 ES ES00984123T patent/ES2275567T3/es not_active Expired - Lifetime
- 2000-12-06 WO PCT/US2000/033432 patent/WO2001039773A1/en not_active Ceased
- 2000-12-06 EP EP00984123A patent/EP1244446B1/en not_active Expired - Lifetime
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