JP2003515560A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- -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
- QETVTIRTIXUXOQ-UHFFFAOYSA-N 9-hydroxy-2-(2-methoxy-3-phenylphenyl)-3h-benzo[e]benzimidazole-5-sulfonic acid;hydrochloride Chemical compound Cl.COC1=C(C=2NC3=C(C4=C(O)C=CC=C4C(=C3)S(O)(=O)=O)N=2)C=CC=C1C1=CC=CC=C1 QETVTIRTIXUXOQ-UHFFFAOYSA-N 0.000 description 1
- 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
- FQBOPVPAANYUNP-UHFFFAOYSA-N 9-hydroxy-2-(2-methoxy-3-phenylphenyl)-3h-benzo[e]benzimidazole-7-sulfonic acid;hydrochloride Chemical compound Cl.COC1=C(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)S(O)(=O)=O)N=2)C=CC=C1C1=CC=CC=C1 FQBOPVPAANYUNP-UHFFFAOYSA-N 0.000 description 1
- 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
- UDKWCHCYYXBFLF-UHFFFAOYSA-N 9-hydroxy-2-[3-(4-propylphenyl)phenyl]-3h-benzo[e]benzimidazole-7-carboxylic acid Chemical compound C1=CC(CCC)=CC=C1C1=CC=CC(C=2NC3=C(C4=C(O)C=C(C=C4C=C3)C(O)=O)N=2)=C1 UDKWCHCYYXBFLF-UHFFFAOYSA-N 0.000 description 1
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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
- 150000004677 hydrates Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 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 |
|---|---|
| JP2003515560A JP2003515560A (ja) | 2003-05-07 |
| JP2003515560A5 true JP2003515560A5 (enExample) | 2008-01-31 |
Family
ID=22614367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001541505A Pending JP2003515560A (ja) | 1999-12-06 | 2000-12-06 | トロンボポイエチン模倣物 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP1244446B1 (enExample) |
| 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 |
|---|---|---|---|---|
| US7851503B2 (en) | 2002-08-14 | 2010-12-14 | Nissan Chemical Industries, Ltd. | Thrombopoetin receptor activator and process for producing the same |
| TWI324593B (en) | 2002-10-09 | 2010-05-11 | Nissan Chemical Ind Ltd | Pyrazolone compounds and thrombopoietin receptor activator |
| CN100513398C (zh) | 2002-12-03 | 2009-07-15 | Axys药物公司 | 作为因子viia抑制剂的2-(2-羟基联苯-3-基)-1h-苯并咪唑-5-甲脒衍生物 |
| JP4896518B2 (ja) * | 2002-12-13 | 2012-03-14 | ワイエム・バイオサイエンシズ・オーストラリア・ピーティーワイ・リミテッド | ニコチンアミド系キナーゼ阻害薬 |
| US20060084682A1 (en) * | 2002-12-13 | 2006-04-20 | Heerding Dirk A | Thrombopoietin mimetics |
| TW200418791A (en) * | 2003-01-23 | 2004-10-01 | Bristol Myers Squibb Co | Pharmaceutical compositions for inhibiting proteasome |
| KR20060079190A (ko) * | 2003-08-14 | 2006-07-05 | 아사히 가세이 파마 가부시키가이샤 | 치환 아릴알칸산 유도체 및 그의 용도 |
| 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 |
| EP1910338B1 (en) * | 2005-07-14 | 2010-08-25 | Irm, Llc | Heterotetracyclic compounds as tpo mimetics |
| JP5071375B2 (ja) | 2005-07-15 | 2012-11-14 | 日産化学工業株式会社 | チオフェン化合物及びトロンボポエチンレセプター活性化剤 |
| 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 |
| RU2385865C2 (ru) * | 2005-08-15 | 2010-04-10 | Айрм Ллк | Соединения и композиции в качестве миметиков тро |
| US8026368B2 (en) | 2005-11-07 | 2011-09-27 | Nissan Chemical Industries, Ltd. | Hydrazide compounds and thrombopoietin receptor activators |
| US8093251B2 (en) | 2006-06-07 | 2012-01-10 | Nissan Chemical Industries, Ltd. | Nitrogen-containing heterocyclic compounds and thrombopoietin receptor activators |
| EP2054405B1 (en) | 2006-07-11 | 2013-09-18 | Daewoong Pharmaceutical Co., Ltd. | Novel biaryl benzoimidazole derivatives and pharmaceutical composition comprising the same |
| NZ580662A (en) | 2007-04-30 | 2012-01-12 | Abbott Lab | Inhibitors of diacylglycerol o-acyltransferase type 1 enzyme used in manufacture of medicament for treatment of diabetes or lipid associated disorders |
| 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 |
| WO2013086436A1 (en) | 2011-12-08 | 2013-06-13 | Fred Hutchinson Cancer Research Center | Compositions and methods for enhanced generation of hematopoietic stem/progenitor cells |
| SI2807165T1 (sl) | 2012-01-27 | 2019-08-30 | Universite De Montreal | Pirimido(4,5-B)indol derivati in njihova uporaba pri ekspanziji hematopoetskih matičnih celic |
| CA2946446C (en) | 2014-04-22 | 2020-11-03 | Universite De Montreal | Pyrido-pyrrolo-pyrimidine and pyrido-indole compounds, pharmaceutical compositions containing same and their use thereof in the expansion of hematopoietic stem cells and/or hematopoietic progenitor cells |
| SG11201703407UA (en) | 2014-10-31 | 2017-05-30 | Nissan Chemical Ind Ltd | Ligand-binding fiber and cell culture substrate using said fiber |
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 |
| IE70217B1 (en) * | 1990-08-15 | 1996-10-30 | British Bio Technology | Benzimidazole derivatives process for their preparation and application |
-
2000
- 2000-12-06 DE DE60031714T patent/DE60031714T2/de not_active Expired - Fee Related
- 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 EP EP00984123A patent/EP1244446B1/en not_active Expired - Lifetime
- 2000-12-06 WO PCT/US2000/033432 patent/WO2001039773A1/en not_active Ceased
- 2000-12-06 AT AT00984123T patent/ATE344031T1/de not_active IP Right Cessation
- 2000-12-06 ES ES00984123T patent/ES2275567T3/es not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4766384B2 (ja) | リゾホスファチジン酸受容体拮抗作用を有する化合物およびその用途 | |
| CA2441239A1 (en) | Mch antagonists and their use in the treatment of obesity | |
| ES2268327T3 (es) | Uso de un selectivo de un receptor de ep4 para el tratamiento de enfermedades. | |
| KR970042507A (ko) | 세포간질 메탈로프로티에이즈 억제제 | |
| ES2321509T3 (es) | Compuestos de piperidina sustituidos con fenilo para usar como activadores de ppar. | |
| RU2007106969A (ru) | Новые пиперидиновые производные в качестве лигандов гистаминового рецептора для лечения депрессии | |
| PT94374A (pt) | Processo de preparacao de acidos imidazolilalcenoicos e de composicooes farmaceuticas que os contem | |
| EP1452525A1 (en) | Amide derivatives and drugs | |
| JP2005536519A5 (enExample) | ||
| JP2003503387A5 (enExample) | ||
| RU96112148A (ru) | Антагонисты рецепторов эндотелина | |
| PT94377B (pt) | Processo de preparacao de acidos imidazolilalcenoicos e de composicoes farmaceuticas que os contem | |
| JP2004534824A5 (enExample) | ||
| JP2002501945A5 (enExample) | ||
| RU2008144962A (ru) | Замещенные имидазол-4-карбоксамиды в качестве модуляторов рецепторов холецистокина-1 | |
| RU2002133215A (ru) | Производные фенилглицина | |
| JP2003515560A (ja) | トロンボポイエチン模倣物 | |
| RU96120211A (ru) | Применение производных имидазола для приготовления фармкомпозиций, активных к рецепторам ат1 и ат2 ангиотензина, некоторые из этих соединений, способ получения производных имидазола и фармацевтические композиции на их основе | |
| JPH10279578A5 (enExample) | ||
| JP2009537595A5 (enExample) | ||
| JP2002520382A5 (enExample) | ||
| JP2003502367A5 (enExample) | ||
| RU2001119461A (ru) | Гидроксаматы сульфонамидов | |
| JP5014978B2 (ja) | ヘテロ６員環化合物及びその用途 | |
| JP7416757B2 (ja) | 置換テトラヒドロシクロペンタ［ｃ］ピロール、置換ジヒドロピロリジン、その類似体、およびそれらを使用する方法 |