JP2008513464A5 - - Google Patents
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- JP2008513464A5 JP2008513464A5 JP2007532443A JP2007532443A JP2008513464A5 JP 2008513464 A5 JP2008513464 A5 JP 2008513464A5 JP 2007532443 A JP2007532443 A JP 2007532443A JP 2007532443 A JP2007532443 A JP 2007532443A JP 2008513464 A5 JP2008513464 A5 JP 2008513464A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- pyrazol
- optionally substituted
- urea
- methylpiperazin
- 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.)
- Granted
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- UNVGACXOVYOCOL-UHFFFAOYSA-N 1-phenyl-3-[4-(3-phenyl-1h-pyrazol-5-yl)phenyl]urea Chemical compound C=1C=C(C=2NN=C(C=2)C=2C=CC=CC=2)C=CC=1NC(=O)NC1=CC=CC=C1 UNVGACXOVYOCOL-UHFFFAOYSA-N 0.000 claims description 4
- ZNKYISLIJARLPJ-UHFFFAOYSA-N 2-(3-phenyl-1H-pyrazol-5-yl)-1H-benzimidazole Chemical compound C=1C(C=2NC3=CC=CC=C3N=2)=NNC=1C1=CC=CC=C1 ZNKYISLIJARLPJ-UHFFFAOYSA-N 0.000 claims description 3
- BWMOTGRGZOGGPC-DAFODLJHSA-N 4-[(E)-2-(3-pyridin-4-yl-1H-pyrazol-5-yl)ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2C=CN=CC=2)=NN1 BWMOTGRGZOGGPC-DAFODLJHSA-N 0.000 claims description 3
- FOPKAHVFWRJAQO-QPJJXVBHSA-N 4-[(E)-2-[3-(3-chlorophenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2C=C(Cl)C=CC=2)=NN1 FOPKAHVFWRJAQO-QPJJXVBHSA-N 0.000 claims description 3
- MLIZWELCMQRQMI-UNXLUWIOSA-N 4-[(E)-2-[3-(4-chlorophenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2C=CC(Cl)=CC=2)=NN1 MLIZWELCMQRQMI-UNXLUWIOSA-N 0.000 claims description 3
- NBLSOXLPSOZWOF-ORCRQEGFSA-N 4-[(E)-2-[3-(5-chloro-1-benzofuran-2-yl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2OC3=CC=C(Cl)C=C3C=2)=NN1 NBLSOXLPSOZWOF-ORCRQEGFSA-N 0.000 claims description 3
- HMFDAWKQTIGMHE-GORDUTHDSA-N 4-[(E)-2-[3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C3=NNC(\C=C\C=4C=CC(O)=CC=4)=C3)C2=C1 HMFDAWKQTIGMHE-GORDUTHDSA-N 0.000 claims description 3
- AUBLOAIVSCNBKR-UHFFFAOYSA-N 1-(2,4-dimethoxyphenyl)-3-[4-[3-[4-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazol-5-yl]phenyl]urea Chemical compound COC1=CC(OC)=CC=C1NC(=O)NC1=CC=C(C2=NNC(=C2)C=2C=CC(=CC=2)N2CCN(C)CC2)C=C1 AUBLOAIVSCNBKR-UHFFFAOYSA-N 0.000 claims description 2
- YHAOCCRRHJMMBF-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)NC1=CC=C(C=2NN=C(C=2)C=2NC3=CC=C(C=C3N=2)N2CCN(C)CC2)C=C1 YHAOCCRRHJMMBF-UHFFFAOYSA-N 0.000 claims description 2
- TXZXAPSGPZZZDZ-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-3-[4-[3-[4-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazol-5-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(C=2NN=C(C=2)C=2C=CC(NC(=O)NC=3C=C(C)C(C)=CC=3)=CC=2)C=C1 TXZXAPSGPZZZDZ-UHFFFAOYSA-N 0.000 claims description 2
- PWIOZOJGSPTINN-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound COC1=CC(OC)=CC(NC(=O)NC=2C=CC(=CC=2)C=2NN=C(C=2)C=2NC3=CC(=CC=C3N=2)N2CCN(C)CC2)=C1 PWIOZOJGSPTINN-UHFFFAOYSA-N 0.000 claims description 2
- KUHLUPFMZODMCI-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(C=CC=4)C(C)=O)=CC=3)C2=C1 KUHLUPFMZODMCI-UHFFFAOYSA-N 0.000 claims description 2
- LLWVODYKLPKHMN-UHFFFAOYSA-N 1-(3-bromophenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(Br)C=CC=4)=CC=3)C2=C1 LLWVODYKLPKHMN-UHFFFAOYSA-N 0.000 claims description 2
- WJNDOEISGQZYEY-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(Cl)C=CC=4)=CC=3)C2=C1 WJNDOEISGQZYEY-UHFFFAOYSA-N 0.000 claims description 2
- NIROGIQQTUAATM-UHFFFAOYSA-N 1-(3-cyanophenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(C=CC=4)C#N)=CC=3)C2=C1 NIROGIQQTUAATM-UHFFFAOYSA-N 0.000 claims description 2
- SEXTZSJGAYFEEI-UHFFFAOYSA-N 1-(3-ethylphenyl)-3-[4-[5-[6-(4-ethylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(CC)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(CC)C=CC=4)=CC=3)C2=C1 SEXTZSJGAYFEEI-UHFFFAOYSA-N 0.000 claims description 2
- GXQVYPBKQQFZJF-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(F)C=CC=4)=CC=3)C2=C1 GXQVYPBKQQFZJF-UHFFFAOYSA-N 0.000 claims description 2
- YYZZMSASVOGZPR-UHFFFAOYSA-N 1-(3-methoxyphenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2NN=C(C=2)C=2NC3=CC=C(C=C3N=2)N2CCN(C)CC2)=C1 YYZZMSASVOGZPR-UHFFFAOYSA-N 0.000 claims description 2
- YEINNCXXMOKBBJ-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[4-[3-[4-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazol-5-yl]phenyl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(C2=NNC(=C2)C=2C=CC(=CC=2)N2CCN(C)CC2)C=C1 YEINNCXXMOKBBJ-UHFFFAOYSA-N 0.000 claims description 2
- QMXYXDDXLLYOEK-UHFFFAOYSA-N 1-(5-fluoro-2-methylphenyl)-3-[4-[3-[4-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazol-5-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(C=2NN=C(C=2)C=2C=CC(NC(=O)NC=3C(=CC=C(F)C=3)C)=CC=2)C=C1 QMXYXDDXLLYOEK-UHFFFAOYSA-N 0.000 claims description 2
- RFAFVIBQOPKAMS-UHFFFAOYSA-N 1-(5-fluoro-2-methylphenyl)-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C(=CC=C(F)C=4)C)=CC=3)C2=C1 RFAFVIBQOPKAMS-UHFFFAOYSA-N 0.000 claims description 2
- KSRNSBDVOGXRSA-UHFFFAOYSA-N 1-[4-[3-[4-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazol-5-yl]phenyl]-3-(4-phenoxyphenyl)urea Chemical compound C1CN(C)CCN1C1=CC=C(C=2NN=C(C=2)C=2C=CC(NC(=O)NC=3C=CC(OC=4C=CC=CC=4)=CC=3)=CC=2)C=C1 KSRNSBDVOGXRSA-UHFFFAOYSA-N 0.000 claims description 2
- BFAZLLILGUBKLN-UHFFFAOYSA-N 1-[4-[3-[5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-5-yl]phenyl]-3-(4-phenoxyphenyl)urea Chemical compound C1CN(C)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=CC(OC=5C=CC=CC=5)=CC=4)=CC=3)C2=C1 BFAZLLILGUBKLN-UHFFFAOYSA-N 0.000 claims description 2
- LWNQQYVQFOKGFZ-UHFFFAOYSA-N 1-[4-[5-(1H-benzimidazol-2-yl)-1H-pyrazol-3-yl]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound FC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(C=2NN=C(C=2)C=2NC3=CC=CC=C3N=2)C=C1 LWNQQYVQFOKGFZ-UHFFFAOYSA-N 0.000 claims description 2
- UPBOAWKNGYHJFL-UHFFFAOYSA-N 1-[4-[5-(1H-benzimidazol-2-yl)-1H-pyrazol-3-yl]phenyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2C=CC(=CC=2)C=2NN=C(C=2)C=2NC3=CC=CC=C3N=2)=C1 UPBOAWKNGYHJFL-UHFFFAOYSA-N 0.000 claims description 2
- IQBZCJJYPBSHPM-UHFFFAOYSA-N 1-[4-[5-(1H-benzimidazol-2-yl)-1H-pyrazol-3-yl]phenyl]-3-phenylurea Chemical compound C=1C=C(C=2NN=C(C=2)C=2NC3=CC=CC=C3N=2)C=CC=1NC(=O)NC1=CC=CC=C1 IQBZCJJYPBSHPM-UHFFFAOYSA-N 0.000 claims description 2
- RWFMPPFJSSCFSZ-UHFFFAOYSA-N 1-[4-[5-[6-(4-ethylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1CN(CC)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(C=CC=4)C(F)(F)F)=CC=3)C2=C1 RWFMPPFJSSCFSZ-UHFFFAOYSA-N 0.000 claims description 2
- BJEFIVOIKYMRCJ-UHFFFAOYSA-N 1-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=CC(=CC=4)C(F)(F)F)=CC=3)C2=C1 BJEFIVOIKYMRCJ-UHFFFAOYSA-N 0.000 claims description 2
- XGXVRIZHNNPJAG-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-(3-phenyl-1h-pyrazol-5-yl)phenyl]urea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC=2C=CC(=CC=2)C=2NN=C(C=2)C=2C=CC=CC=2)=C1 XGXVRIZHNNPJAG-UHFFFAOYSA-N 0.000 claims description 2
- WXOCBNPLVCJMTC-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-[3-[3-(4-methylpiperazin-1-yl)phenyl]-1h-pyrazol-5-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=CC(C2=NNC(=C2)C=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 WXOCBNPLVCJMTC-UHFFFAOYSA-N 0.000 claims description 2
- FGTJWNITGBGXMZ-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-[3-[4-(4-ethylpiperazin-1-yl)phenyl]-1h-pyrazol-5-yl]phenyl]urea Chemical compound C1CN(CC)CCN1C1=CC=C(C2=NNC(=C2)C=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)C=C1 FGTJWNITGBGXMZ-UHFFFAOYSA-N 0.000 claims description 2
- DKKVMPVQHSMJDF-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-[5-[6-(4-ethylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(CC)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(C(Cl)=CC=4)C(F)(F)F)=CC=3)C2=C1 DKKVMPVQHSMJDF-UHFFFAOYSA-N 0.000 claims description 2
- BAHVZNVPKFIXEX-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(C(Cl)=CC=4)C(F)(F)F)=CC=3)C2=C1 BAHVZNVPKFIXEX-UHFFFAOYSA-N 0.000 claims description 2
- NCTVANRJURGURM-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-3-[4-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(C)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC=4C=C(C(F)=CC=4)C(F)(F)F)=CC=3)C2=C1 NCTVANRJURGURM-UHFFFAOYSA-N 0.000 claims description 2
- XULCFTJVFFDUEQ-UHFFFAOYSA-N 1-tert-butyl-3-[4-[5-[6-(4-ethylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-3-yl]phenyl]urea Chemical compound C1CN(CC)CCN1C1=CC=C(NC(=N2)C3=NNC(=C3)C=3C=CC(NC(=O)NC(C)(C)C)=CC=3)C2=C1 XULCFTJVFFDUEQ-UHFFFAOYSA-N 0.000 claims description 2
- CPKHTHXZMOTBNW-AMMQDNIMSA-N 2-methoxy-4-[(E)-2-[5-[(E)-2-phenylethenyl]-1H-pyrazol-3-yl]ethenyl]phenol Chemical compound C1=C(O)C(OC)=CC(\C=C\C2=NNC(\C=C\C=3C=CC=CC=3)=C2)=C1 CPKHTHXZMOTBNW-AMMQDNIMSA-N 0.000 claims description 2
- FSLWYZJHWQSUPI-BJMVGYQFSA-N 4-[(E)-2-(3-naphthalen-2-yl-1H-pyrazol-5-yl)ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=NNC(C=2C=C3C=CC=CC3=CC=2)=C1 FSLWYZJHWQSUPI-BJMVGYQFSA-N 0.000 claims description 2
- PRYAFQCMNWMECR-QPJJXVBHSA-N 4-[(E)-2-(3-pyridin-2-yl-1H-pyrazol-5-yl)ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=NNC(C=2N=CC=CC=2)=C1 PRYAFQCMNWMECR-QPJJXVBHSA-N 0.000 claims description 2
- HSMJLCSUUOQBOZ-ZZXKWVIFSA-N 4-[(E)-2-(3-pyridin-3-yl-1H-pyrazol-5-yl)ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2C=NC=CC=2)=NN1 HSMJLCSUUOQBOZ-ZZXKWVIFSA-N 0.000 claims description 2
- OEYVNKQNSGYQEF-VMPITWQZSA-N 4-[(E)-2-[3-(1-benzofuran-2-yl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2OC3=CC=CC=C3C=2)=NN1 OEYVNKQNSGYQEF-VMPITWQZSA-N 0.000 claims description 2
- QWCNHNIOQZJPNT-VMPITWQZSA-N 4-[(E)-2-[3-(1-benzothiophen-2-yl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2SC3=CC=CC=C3C=2)=NN1 QWCNHNIOQZJPNT-VMPITWQZSA-N 0.000 claims description 2
- BZOBUERGOWVPRK-VMPITWQZSA-N 4-[(E)-2-[3-(1H-benzimidazol-2-yl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2NC3=CC=CC=C3N=2)=NN1 BZOBUERGOWVPRK-VMPITWQZSA-N 0.000 claims description 2
- UCCWOFLIPJFAHT-VMPITWQZSA-N 4-[(E)-2-[3-(2-chlorophenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2C(=CC=CC=2)Cl)=NN1 UCCWOFLIPJFAHT-VMPITWQZSA-N 0.000 claims description 2
- FCNKFHXLVQHAOD-RMKNXTFCSA-N 4-[(E)-2-[3-(2-methoxyphenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound COC1=CC=CC=C1C1=CC(\C=C\C=2C=CC(O)=CC=2)=NN1 FCNKFHXLVQHAOD-RMKNXTFCSA-N 0.000 claims description 2
- OXPXWVRPVIUAQC-ORCRQEGFSA-N 4-[(E)-2-[3-(3,4-dichlorophenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(C=2C=C(Cl)C(Cl)=CC=2)=NN1 OXPXWVRPVIUAQC-ORCRQEGFSA-N 0.000 claims description 2
- RMYBJJQTEUBMQN-QPJJXVBHSA-N 4-[(E)-2-[3-(3-fluorophenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=NNC(C=2C=C(F)C=CC=2)=C1 RMYBJJQTEUBMQN-QPJJXVBHSA-N 0.000 claims description 2
- OPDAZKGVKDXANM-VMPITWQZSA-N 4-[(E)-2-[3-(3-methoxyphenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound COC1=CC=CC(C=2NN=C(\C=C\C=3C=CC(O)=CC=3)C=2)=C1 OPDAZKGVKDXANM-VMPITWQZSA-N 0.000 claims description 2
- YNNGDNUKMXQTQV-FMIVXFBMSA-N 4-[(E)-2-[3-(3-phenylphenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=NNC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 YNNGDNUKMXQTQV-FMIVXFBMSA-N 0.000 claims description 2
- DSLMHMBHXDLJQB-UNXLUWIOSA-N 4-[(E)-2-[3-(4-fluorophenyl)-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=NNC(C=2C=CC(F)=CC=2)=C1 DSLMHMBHXDLJQB-UNXLUWIOSA-N 0.000 claims description 2
- DPNTWSKIBWUWHP-JMQWPVDRSA-N 4-[(E)-2-[3-[(E)-2-phenylethenyl]-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1=CC(O)=CC=C1\C=C\C1=NNC(\C=C\C=2C=CC=CC=2)=C1 DPNTWSKIBWUWHP-JMQWPVDRSA-N 0.000 claims description 2
- PAZHOZHJTZICIY-VMPITWQZSA-N 4-[(E)-2-[3-[3-(4-methylpiperazin-1-yl)phenyl]-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1CN(C)CCN1C1=CC=CC(C2=NNC(\C=C\C=3C=CC(O)=CC=3)=C2)=C1 PAZHOZHJTZICIY-VMPITWQZSA-N 0.000 claims description 2
- JAJQTJFZXCGZBY-FARCUNLSSA-N 4-[(E)-2-[3-[4-(4-methylpiperazin-1-yl)phenyl]-1H-pyrazol-5-yl]ethenyl]phenol Chemical compound C1CN(C)CCN1C1=CC=C(C2=NNC(\C=C\C=3C=CC(O)=CC=3)=C2)C=C1 JAJQTJFZXCGZBY-FARCUNLSSA-N 0.000 claims description 2
- PYFOQXYFYZSHHD-BHFHGZQMSA-N 4-[(E)-2-[5-[(E)-2-(2,4-difluorophenyl)ethenyl]-1H-pyrazol-3-yl]ethenyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(\C=C\C=2NN=C(\C=C\C=3C(=CC(F)=CC=3)F)C=2)=C1 PYFOQXYFYZSHHD-BHFHGZQMSA-N 0.000 claims description 2
- IZCKTWCFIHMTFY-LUZURFALSA-N 4-[(E)-2-[5-[(E)-2-(4-chlorophenyl)ethenyl]-1H-pyrazol-3-yl]ethenyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(\C=C\C=2NN=C(\C=C\C=3C=CC(Cl)=CC=3)C=2)=C1 IZCKTWCFIHMTFY-LUZURFALSA-N 0.000 claims description 2
- GAPVQUGDPGVQHN-LUZURFALSA-N 4-[(E)-2-[5-[(E)-2-(4-fluorophenyl)ethenyl]-1H-pyrazol-3-yl]ethenyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(\C=C\C=2NN=C(\C=C\C=3C=CC(F)=CC=3)C=2)=C1 GAPVQUGDPGVQHN-LUZURFALSA-N 0.000 claims description 2
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| JP2012112312A Withdrawn JP2012153720A (ja) | 2004-09-17 | 2012-05-16 | ピラゾールキナーゼモジュレーターおよび使用方法 |
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| CA (1) | CA2579313A1 (enExample) |
| WO (1) | WO2006033943A2 (enExample) |
Families Citing this family (23)
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| AR051093A1 (es) | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de estearoil-coa desaturasa |
| MX2007003332A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de estearoil-coa-desaturasa. |
| EP2029138A1 (en) | 2005-06-03 | 2009-03-04 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| CN101058561B (zh) * | 2006-04-19 | 2011-01-26 | 苏州爱斯鹏药物研发有限责任公司 | 用于抑制蛋白激酶的二苯脲衍生物及其组合物和用途 |
| WO2009143039A2 (en) * | 2008-05-19 | 2009-11-26 | Schering Corporation | Heterocyclic compounds as factor ixa inhibitors |
| ES2620027T3 (es) | 2008-09-03 | 2017-06-27 | Biomarin Pharmaceutical Inc. | Composiciones que incluyen derivados del ácido 6-aminohexanoico como inhibidores de HDAC |
| US8329757B2 (en) * | 2008-10-14 | 2012-12-11 | Charlesson, Llc | Curcumin analog compositions and related methods |
| EP2545046A4 (en) | 2010-03-11 | 2015-03-25 | Sumitomo Dainippon Pharma Co Ltd | CYCLIC N-ACYL-AMINE DERIVATIVE OR PHARMACEUTICALLY ALLOWED SALT THEREOF |
| KR20130089232A (ko) * | 2010-06-15 | 2013-08-09 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 안트라닐산 디아미드 유도체 |
| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| CA2832650C (en) | 2011-04-11 | 2019-05-07 | Pharma Eight Co. Ltd. | Pyrazole derivative |
| US9199975B2 (en) | 2011-09-30 | 2015-12-01 | Asana Biosciences, Llc | Biaryl imidazole derivatives for regulating CYP17 |
| US8809372B2 (en) | 2011-09-30 | 2014-08-19 | Asana Biosciences, Llc | Pyridine derivatives |
| RU2682679C2 (ru) * | 2012-10-10 | 2019-03-20 | Грин Тек Ко., Лтд. | Новые производные пиразола |
| PL403149A1 (pl) * | 2013-03-14 | 2014-09-15 | Celon Pharma Spółka Akcyjna | Nowe związki pochodne pirazolilobenzo[d]imidazolu |
| KR20150132345A (ko) | 2013-03-15 | 2015-11-25 | 바이오마린 파머수티컬 인크. | Hdac 저해제 |
| EP2944635B1 (en) * | 2014-05-15 | 2018-11-28 | Council of Scientific & Industrial Research | Pyrazole linked benzimidazole conjugates and a process for preparation thereof |
| GB201506658D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| GB201506660D0 (en) | 2015-04-20 | 2015-06-03 | Cellcentric Ltd | Pharmaceutical compounds |
| EP3643705A1 (en) * | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
| JP7742175B2 (ja) * | 2021-03-03 | 2025-09-19 | 白鳥製薬株式会社 | ピラゾール化合物の製造方法 |
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| DE923028C (de) | 1952-04-02 | 1955-01-31 | Basf Ag | Verfahren zur Herstellung von Kuepenfarbstoffen |
| US3948937A (en) * | 1972-02-29 | 1976-04-06 | E. I. Du Pont De Nemours And Company | Pyrazole plant growth regulants |
| ZA744908B (en) * | 1973-09-17 | 1975-08-27 | American Cyanamid Co | Catalytic dehydrogenation process for the preparation of 3,5-disubstituted pyrazoles |
| GB1484615A (en) * | 1974-11-23 | 1977-09-01 | Lepetit Spa | Tricyclic n-containing derivatives |
| US4014896A (en) * | 1975-02-12 | 1977-03-29 | American Cyanamid Company | Catalytic dehydrogenation process for the preparation of 3,4,5-trisubstituted pyrazoles |
| IE59813B1 (en) * | 1986-05-09 | 1994-04-06 | Warner Lambert Co | Styryl pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxy-genase inhibitors and pharmaceutical compositions containing them |
| US4877881A (en) * | 1987-04-06 | 1989-10-31 | Warner-Lambert Company | Process of preparing pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxygenase inhibitors |
| DE3903993A1 (de) * | 1989-02-10 | 1990-08-16 | Basf Ag | Diarylsubstituierte heterocyclische verbindungen, ihre herstellung und arzneimittel daraus |
| JPH04124178A (ja) * | 1990-09-12 | 1992-04-24 | Sds Biotech Kk | 複素環式化合物および該化合物を含有する除草剤 |
| DE59407859D1 (de) * | 1993-06-08 | 1999-04-08 | Basf Ag | Verfahren zur Herstellung von N-substituierten Pyrazolen |
| US5783593A (en) * | 1993-11-04 | 1998-07-21 | Abbott Laboratories | Inhibitors of squalene synthetase and protein farnesyltransferase |
| DE19500838A1 (de) * | 1995-01-13 | 1996-07-18 | Basf Ag | Verfahren zur Herstellung von 3,5-Diarylpyrazolen |
| DE69935335T2 (de) | 1998-08-07 | 2007-11-22 | Novartis Vaccines and Diagnostics, Inc., Emeryville | Pyrazole als modulatoren des östrogenrezeptors |
| AU1199600A (en) * | 1998-10-02 | 2000-04-26 | Board Of Trustees Of The University Of Illinois, The | Estrogen receptor ligands |
| DE19904397A1 (de) | 1999-02-04 | 2000-08-10 | Bayer Ag | Verwendung von Pyrazol-Carbonsäureamiden |
| JP2003523958A (ja) * | 1999-12-23 | 2003-08-12 | ニトロメド インコーポレーテッド | ニトロソ化およびニトロシル化されたシクロオキシゲナーゼ−２の阻害剤、組成物ならびに使用法 |
| US6914069B2 (en) * | 2000-05-19 | 2005-07-05 | Applied Research Systems Ars Holding N.V. | Pharmaceutically active compounds and methods of use |
| SI1373263T1 (en) * | 2001-04-05 | 2005-04-30 | Torrent Pharmaceuticals Ltd | Heterocyclic compounds for aging-related and diabetic vascular complications |
| CN1638776A (zh) | 2001-06-08 | 2005-07-13 | 西托维亚公司 | 取代的3－芳基－5－芳基－[1,2,4]－噁二唑和类似物 |
| IL161576A0 (en) | 2001-10-26 | 2004-09-27 | Aventis Pharma Inc | Benzimidazoles and analogues and their use as protein kinases inhibitors |
| FR2831536A1 (fr) * | 2001-10-26 | 2003-05-02 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de kdr |
| JP2005162612A (ja) * | 2002-01-09 | 2005-06-23 | Ajinomoto Co Inc | アシルスルホンアミド誘導体 |
| US6790979B2 (en) * | 2002-04-17 | 2004-09-14 | University Of North Carolina At Chapel Hill | Curcumin analogues and uses thereof |
| NI200300045A (es) * | 2002-04-26 | 2005-07-08 | Pfizer Prod Inc | Inhibidores de triariloxiariloxipirimidin-2,4,6-triona de metaloproteinasa. |
| AU2002314566A1 (en) * | 2002-06-17 | 2003-12-31 | Ho-Jeong Kwon | Novel curcumin derivatives |
| US20050113423A1 (en) * | 2003-03-12 | 2005-05-26 | Vangoor Frederick F. | Modulators of ATP-binding cassette transporters |
| US7115642B2 (en) * | 2003-05-02 | 2006-10-03 | Rigel Pharmaceuticals, Inc. | Substituted diphenyl isoxazoles, pyrazoles and oxadiazoles useful for treating HCV infection |
| GB0326601D0 (en) | 2003-11-14 | 2003-12-17 | Novartis Ag | Organic compounds |
| WO2005094823A1 (ja) | 2004-03-30 | 2005-10-13 | Kyowa Hakko Kogyo Co., Ltd. | Ｆｌｔ－３阻害剤 |
| US7517910B2 (en) * | 2004-03-30 | 2009-04-14 | Takeda Pharmaceutical Company Limited | Alkoxyphenylpropanoic acid derivatives |
-
2005
- 2005-09-15 US US11/575,411 patent/US8710038B2/en not_active Expired - Fee Related
- 2005-09-15 WO PCT/US2005/032839 patent/WO2006033943A2/en not_active Ceased
- 2005-09-15 CA CA002579313A patent/CA2579313A1/en not_active Abandoned
- 2005-09-15 EP EP05796701A patent/EP1797072A4/en not_active Withdrawn
- 2005-09-15 AU AU2005287170A patent/AU2005287170B2/en not_active Ceased
- 2005-09-15 JP JP2007532443A patent/JP5063351B2/ja not_active Expired - Fee Related
-
2012
- 2012-05-16 JP JP2012112312A patent/JP2012153720A/ja not_active Withdrawn
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