JP2007507511A5 - - Google Patents
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- Publication number
- JP2007507511A5 JP2007507511A5 JP2006534029A JP2006534029A JP2007507511A5 JP 2007507511 A5 JP2007507511 A5 JP 2007507511A5 JP 2006534029 A JP2006534029 A JP 2006534029A JP 2006534029 A JP2006534029 A JP 2006534029A JP 2007507511 A5 JP2007507511 A5 JP 2007507511A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- benzimidazole
- propoxy
- chloro
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000004122 cyclic group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- -1 -OCH 2 Ph Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- PMSKRMBSAZKNAO-UHFFFAOYSA-N 6-tert-butyl-2-[2-methyl-4-[3-(2-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound CC1CNCCN1CCCOC(C=C1C)=CC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 PMSKRMBSAZKNAO-UHFFFAOYSA-N 0.000 claims 2
- HOGIQAJOASEATP-UHFFFAOYSA-N 6-tert-butyl-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl HOGIQAJOASEATP-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- WFYUITPFJSNEQQ-UHFFFAOYSA-N 1-[2-(5-fluoro-4-methyl-1h-benzimidazol-2-yl)-5-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(C=2NC3=CC=C(F)C(C)=C3N=2)C(CN(C)C)=CC=1OCCCC1CCN(C)CC1 WFYUITPFJSNEQQ-UHFFFAOYSA-N 0.000 claims 1
- JMGPTTNPUMSBTQ-UHFFFAOYSA-N 1-[2-(6-chloro-4-methyl-1h-benzimidazol-2-yl)-5-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-n,n-dimethylmethanamine Chemical compound C=1C=C(C=2NC3=CC(Cl)=CC(C)=C3N=2)C(CN(C)C)=CC=1OCCCC1CCN(C)CC1 JMGPTTNPUMSBTQ-UHFFFAOYSA-N 0.000 claims 1
- AADBANJKFIORNE-UHFFFAOYSA-N 1-[3-[4-(6-tert-butyl-1h-benzimidazol-2-yl)-2-chlorophenoxy]propyl]-n,n-dimethylpyrrolidin-3-amine Chemical compound C1C(N(C)C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)C=C1Cl AADBANJKFIORNE-UHFFFAOYSA-N 0.000 claims 1
- QSSIZKWOJDCWML-UHFFFAOYSA-N 2-[2-chloro-4-[2-methyl-3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=CC(C)=C3N=2)C(Cl)=CC=1OCC(C)CN1CCN(C)CC1 QSSIZKWOJDCWML-UHFFFAOYSA-N 0.000 claims 1
- CCHJDYXWLQLTHD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-3h-benzo[e]benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1C=CC1=CC=CC=C21 CCHJDYXWLQLTHD-UHFFFAOYSA-N 0.000 claims 1
- ZBKOPZVHMTXXQH-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 ZBKOPZVHMTXXQH-UHFFFAOYSA-N 0.000 claims 1
- BYEFGIKEWXKOAC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 BYEFGIKEWXKOAC-UHFFFAOYSA-N 0.000 claims 1
- YPWPMKJVTQONQH-UHFFFAOYSA-N 2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 YPWPMKJVTQONQH-UHFFFAOYSA-N 0.000 claims 1
- RPIXQBZODSVPPC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 RPIXQBZODSVPPC-UHFFFAOYSA-N 0.000 claims 1
- JMQRDCNEFGNPAL-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 JMQRDCNEFGNPAL-UHFFFAOYSA-N 0.000 claims 1
- WMGUYQXCPREFOF-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 WMGUYQXCPREFOF-UHFFFAOYSA-N 0.000 claims 1
- PBYAQWILYFZYHC-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC=CC=C2N1 PBYAQWILYFZYHC-UHFFFAOYSA-N 0.000 claims 1
- SKQKGGHCXLOMFJ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-3h-benzo[e]benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C(N1)=NC2=C1C=CC1=CC=CC=C21 SKQKGGHCXLOMFJ-UHFFFAOYSA-N 0.000 claims 1
- FKLHKZSFHAZKBD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4,5-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(C)=CC=C2N1 FKLHKZSFHAZKBD-UHFFFAOYSA-N 0.000 claims 1
- SIDSFFAOACXBRD-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4,6-dimethyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=C(C)C=C2N1 SIDSFFAOACXBRD-UHFFFAOYSA-N 0.000 claims 1
- DIFIANIFCWCWIA-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C=CC=C2N1 DIFIANIFCWCWIA-UHFFFAOYSA-N 0.000 claims 1
- NPYCKTMZMUAVJW-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-5-fluoro-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=C(C)C(F)=CC=C2N1 NPYCKTMZMUAVJW-UHFFFAOYSA-N 0.000 claims 1
- NYNGHPOORNFKGZ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethoxy)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(OC(F)(F)F)=CC=C2N1 NYNGHPOORNFKGZ-UHFFFAOYSA-N 0.000 claims 1
- KGTCKJNHHCXYEZ-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(C(F)(F)F)=CC=C2N1 KGTCKJNHHCXYEZ-UHFFFAOYSA-N 0.000 claims 1
- FEMHOUCJHZSJJV-UHFFFAOYSA-N 2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(C)=CC=C2N1 FEMHOUCJHZSJJV-UHFFFAOYSA-N 0.000 claims 1
- KHADFEDGWBHJSK-UHFFFAOYSA-N 2-[2-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C=1C=C(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)C(OC)=CC=1OCCCN1CCN(C)CC1 KHADFEDGWBHJSK-UHFFFAOYSA-N 0.000 claims 1
- KBYGQHKVXVNPHA-UHFFFAOYSA-N 2-[3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=CC(C=2NC3=CC=CC=C3N=2)=C1 KBYGQHKVXVNPHA-UHFFFAOYSA-N 0.000 claims 1
- BHXFOAZKCRAEEO-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC3=CC=CC(C)=C3N=2)C=C1Cl BHXFOAZKCRAEEO-UHFFFAOYSA-N 0.000 claims 1
- UMNDIUWKZLKSRC-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1Cl UMNDIUWKZLKSRC-UHFFFAOYSA-N 0.000 claims 1
- ZJSRVCKWBKNRCM-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)C=C1Cl ZJSRVCKWBKNRCM-UHFFFAOYSA-N 0.000 claims 1
- PVHPABJTUPOEHL-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methoxy-1h-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1C(C=C1Cl)=CC=C1OCCCN1CCN(C)CC1 PVHPABJTUPOEHL-UHFFFAOYSA-N 0.000 claims 1
- QMGSOQRJRHUXGG-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1Cl QMGSOQRJRHUXGG-UHFFFAOYSA-N 0.000 claims 1
- GYWXPRKRKOTZFC-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1F GYWXPRKRKOTZFC-UHFFFAOYSA-N 0.000 claims 1
- PAHZWMXYPGJECS-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-4-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC(C)=C3N=2)C=C1F PAHZWMXYPGJECS-UHFFFAOYSA-N 0.000 claims 1
- FOWBFPKYEHZJDX-UHFFFAOYSA-N 2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C=C3N=2)C=C1F FOWBFPKYEHZJDX-UHFFFAOYSA-N 0.000 claims 1
- WXWJVMLNEFLGCC-UHFFFAOYSA-N 2-[3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound COC1=CC(C=2NC3=CC=C(C=C3N=2)C(F)(F)F)=CC=C1OCCCN1CCN(C)CC1 WXWJVMLNEFLGCC-UHFFFAOYSA-N 0.000 claims 1
- DOLJNIUPEWVSMY-UHFFFAOYSA-N 2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1C DOLJNIUPEWVSMY-UHFFFAOYSA-N 0.000 claims 1
- KUBYFJXKFPBGHW-UHFFFAOYSA-N 2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC=CC=C3N=2)C=C1 KUBYFJXKFPBGHW-UHFFFAOYSA-N 0.000 claims 1
- HIOACXJIFNRHFT-UHFFFAOYSA-N 4,5-dimethyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C(C)=CC=C3N=2)=C1 HIOACXJIFNRHFT-UHFFFAOYSA-N 0.000 claims 1
- XYCZNRPVEIXUGZ-UHFFFAOYSA-N 4,5-dimethyl-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC=C(C)C(C)=C3N=2)C=C1C XYCZNRPVEIXUGZ-UHFFFAOYSA-N 0.000 claims 1
- CSEXYSDCKNILSQ-UHFFFAOYSA-N 4,6-dimethyl-2-[2-methyl-3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C=C(C)C=C3N=2)=C1C CSEXYSDCKNILSQ-UHFFFAOYSA-N 0.000 claims 1
- ZMUYSFLEOVTVQU-UHFFFAOYSA-N 4,6-dimethyl-2-[3-[4-(4-methyl-1,4-diazepan-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCCOC1=CC=CC(C=2NC3=CC(C)=CC(C)=C3N=2)=C1 ZMUYSFLEOVTVQU-UHFFFAOYSA-N 0.000 claims 1
- DBKCSJUURDYQKR-UHFFFAOYSA-N 4-[3-(6-tert-butyl-1h-benzimidazol-2-yl)phenoxy]-1-(4-methylpiperazin-1-yl)butan-1-one Chemical compound C1CN(C)CCN1C(=O)CCCOC1=CC=CC(C=2NC3=CC=C(C=C3N=2)C(C)(C)C)=C1 DBKCSJUURDYQKR-UHFFFAOYSA-N 0.000 claims 1
- HEOOSKRYIMADSF-UHFFFAOYSA-N 4-[3-[4-(6-chloro-4-methyl-1h-benzimidazol-2-yl)-3-methylphenoxy]propyl]-1,4-diazepan-5-one Chemical compound C=1C=C(C=2NC3=CC(Cl)=CC(C)=C3N=2)C(C)=CC=1OCCCN1CCNCCC1=O HEOOSKRYIMADSF-UHFFFAOYSA-N 0.000 claims 1
- PXCXUOSJIMFZQQ-UHFFFAOYSA-N 4-[3-[4-(6-tert-butyl-1h-benzimidazol-2-yl)-3-methylphenoxy]propyl]-1-methyl-1,4-diazepan-5-one Chemical compound O=C1CCN(C)CCN1CCCOC(C=C1C)=CC=C1C1=NC2=CC(C(C)(C)C)=CC=C2N1 PXCXUOSJIMFZQQ-UHFFFAOYSA-N 0.000 claims 1
- LKAOLMAQJVBSHY-UHFFFAOYSA-N 4-chloro-2-[2-methyl-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1C)=CC=C1C1=NC2=C(Cl)C=CC=C2N1 LKAOLMAQJVBSHY-UHFFFAOYSA-N 0.000 claims 1
- RNBYJCBTCUPEML-UHFFFAOYSA-N 4-methyl-2-[3-[4-(1-methylpiperidin-4-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCCOC1=CC=CC(C=2NC3=C(C)C=CC=C3N=2)=C1 RNBYJCBTCUPEML-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- NBYUHYMOOAWKJK-UHFFFAOYSA-N 5,6-dichloro-2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(Cl)C=C2N1 NBYUHYMOOAWKJK-UHFFFAOYSA-N 0.000 claims 1
- HUVLLIJCEAKWNB-UHFFFAOYSA-N 5,6-dichloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(Cl)=C(Cl)C=C3N=2)C=C1Cl HUVLLIJCEAKWNB-UHFFFAOYSA-N 0.000 claims 1
- YVBUIDRPKJTUJO-UHFFFAOYSA-N 5,6-difluoro-2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(F)C=C3N=2)C=C1F YVBUIDRPKJTUJO-UHFFFAOYSA-N 0.000 claims 1
- JYUNHIWFSACXRN-UHFFFAOYSA-N 5,6-dimethyl-2-[3-[4-(4-methylpiperazin-1-yl)butoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCCOC1=CC=CC(C=2NC3=CC(C)=C(C)C=C3N=2)=C1 JYUNHIWFSACXRN-UHFFFAOYSA-N 0.000 claims 1
- DPLDJYIQOXPYEU-UHFFFAOYSA-N 5-chloro-2-[2-chloro-4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(F)C=C2N1 DPLDJYIQOXPYEU-UHFFFAOYSA-N 0.000 claims 1
- DIUDUBNJSDXXFL-UHFFFAOYSA-N 5-chloro-2-[2-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC(C=C1Cl)=CC=C1C1=NC2=CC(Cl)=C(F)C=C2N1 DIUDUBNJSDXXFL-UHFFFAOYSA-N 0.000 claims 1
- RCFCAROGHBIRJE-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-(3-piperazin-1-ylpropoxy)phenyl]-6-fluoro-1h-benzimidazole Chemical compound N=1C=2C=C(Cl)C(F)=CC=2NC=1C(C=C1Cl)=CC=C1OCCCN1CCNCC1 RCFCAROGHBIRJE-UHFFFAOYSA-N 0.000 claims 1
- FSUQVEFSMOUIAJ-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methyl-1,4-diazepan-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCCN1CCCOC1=CC=C(C=2NC3=CC(C)=C(Cl)C=C3N=2)C=C1Cl FSUQVEFSMOUIAJ-UHFFFAOYSA-N 0.000 claims 1
- NNZBUWXJQQPPMT-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-fluoro-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1Cl NNZBUWXJQQPPMT-UHFFFAOYSA-N 0.000 claims 1
- NJEDSTVFVCYPMY-UHFFFAOYSA-N 5-chloro-2-[3-chloro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-6-methyl-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(C)=C(Cl)C=C3N=2)C=C1Cl NJEDSTVFVCYPMY-UHFFFAOYSA-N 0.000 claims 1
- DMLVEFMJJRWHCV-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1F DMLVEFMJJRWHCV-UHFFFAOYSA-N 0.000 claims 1
- FWEZEGUGSRPQIY-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-methoxy-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound COC1=CC(C=2NC3=CC(F)=C(Cl)C=C3N=2)=CC=C1OCCCN1CCN(C)CC1 FWEZEGUGSRPQIY-UHFFFAOYSA-N 0.000 claims 1
- ZGXXUVQKCZHGKT-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[3-methyl-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCN1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1C ZGXXUVQKCZHGKT-UHFFFAOYSA-N 0.000 claims 1
- NNVQDEHLJNCUEI-UHFFFAOYSA-N 5-chloro-6-fluoro-2-[4-[3-(1-methylpiperidin-4-yl)propoxy]phenyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1CCCOC1=CC=C(C=2NC3=CC(F)=C(Cl)C=C3N=2)C=C1 NNVQDEHLJNCUEI-UHFFFAOYSA-N 0.000 claims 1
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100034819A1 (en) * | 2006-03-31 | 2010-02-11 | Centocor Inc. | Human epo mimetic hinge core mimetibodies, compositions, methods and uses for preventing or treating glucose intolerance related conditions on renal disease associated anemia |
| JP2010507394A (ja) * | 2006-10-24 | 2010-03-11 | トルービオン ファーマスーティカルズ インコーポレイテッド | 改良免疫糖タンパク質のための物質および方法 |
| US7846434B2 (en) | 2006-10-24 | 2010-12-07 | Trubion Pharmaceuticals, Inc. | Materials and methods for improved immunoglycoproteins |
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| US8834920B2 (en) | 2006-12-21 | 2014-09-16 | Alza Corporation | Liposome composition for targeting egfr receptor |
| WO2008079973A2 (en) | 2006-12-21 | 2008-07-03 | Centocor, Inc. | Egfr binding peptides and uses thereof |
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| EP2205280B1 (en) | 2007-09-27 | 2019-09-04 | Amgen Inc. | Pharmaceutical formulations |
| US8796206B2 (en) | 2007-11-15 | 2014-08-05 | Amgen Inc. | Aqueous formulation of erythropoiesis stimulating protein stabilised by antioxidants for parenteral administration |
| WO2009094551A1 (en) | 2008-01-25 | 2009-07-30 | Amgen Inc. | Ferroportin antibodies and methods of use |
| US9315577B2 (en) | 2008-05-01 | 2016-04-19 | Amgen Inc. | Anti-hepcidin antibodies and methods of use |
| US20100029942A1 (en) * | 2008-06-30 | 2010-02-04 | Sergio Cesco-Cancian | Process for the preparation of benzoimidazol-2-yl pyrimidine derivatives |
| JP6018753B2 (ja) | 2008-11-13 | 2016-11-02 | ザ・ジェネラル・ホスピタル・コーポレイションＴｈｅ Ｇｅｎｅｒａｌ Ｈｏｓｐｉｔａｌ Ｃｏｒｐｏｒａｔｉｏｎ | Ｂｍｐ−６の調節によって鉄の恒常性を制御するための方法および組成物 |
| JP2012518408A (ja) * | 2009-02-24 | 2012-08-16 | アレクシオン ファーマシューティカルズ， インコーポレイテッド | 治療用ｔｐｏ／ｅｐｏ模倣ペプチドを含む抗体 |
| US20100291160A1 (en) * | 2009-05-13 | 2010-11-18 | Carver David R | Pharmaceutical system for trans-membrane delivery |
| TWI546537B (zh) * | 2009-05-19 | 2016-08-21 | 維維亞生技公司 | 提供針對血液腫瘤之體外個人化藥物測試之方法 |
| IT1395137B1 (it) | 2009-08-05 | 2012-09-05 | Spider Biotech S R L | Nuovi peptidi antipatogeni |
| WO2011050333A1 (en) | 2009-10-23 | 2011-04-28 | Amgen Inc. | Vial adapter and system |
| ES2581571T3 (es) | 2009-11-17 | 2016-09-06 | Janssen Biotech, Inc. | Presentación de proteínas diméricas de disulfuro vinculado en fagos filamentosos |
| WO2011062862A1 (en) | 2009-11-17 | 2011-05-26 | Centocor Ortho Biotech Inc. | Improved bacterial membrane protein secrection |
| EP2536435B1 (en) | 2010-02-18 | 2017-11-15 | Janssen Biotech, Inc. | Monkey homolog of human interferon omega |
| WO2011130533A1 (en) | 2010-04-16 | 2011-10-20 | Centocor Ortho Biotech Inc. | Engineered plant cysteine proteases and their uses |
| SG186094A1 (en) | 2010-06-07 | 2013-01-30 | Amgen Inc | Drug delivery device |
| ES2757857T3 (es) | 2010-09-27 | 2020-04-30 | Janssen Biotech Inc | Anticuerpos de unión a colágeno II humano |
| EP2447263A1 (en) * | 2010-09-27 | 2012-05-02 | Bioprojet | Benzazole derivatives as histamine H4 receptor ligands |
| AU2012236573B2 (en) | 2011-03-31 | 2016-06-02 | Amgen Inc. | Vial adapter and system |
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| PL3045187T3 (pl) | 2011-10-14 | 2019-09-30 | Amgen Inc. | Wstrzykiwacz i sposób montażu |
| ES2860954T3 (es) | 2012-11-21 | 2021-10-05 | Amgen Inc | Dispositivo de administración de fármacos |
| WO2014152006A2 (en) | 2013-03-15 | 2014-09-25 | Intrinsic Lifesciences, Llc | Anti-hepcidin antibodies and uses thereof |
| US10646664B2 (en) | 2013-03-15 | 2020-05-12 | Amgen Inc. | Body contour adaptable autoinjector device |
| TWI614041B (zh) | 2013-03-15 | 2018-02-11 | 安美基公司 | 用於注射器之匣盒 |
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| WO2014149357A1 (en) | 2013-03-22 | 2014-09-25 | Amgen Inc. | Injector and method of assembly |
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| SG11201602876WA (en) | 2013-10-24 | 2016-05-30 | Amgen Inc | Injector and method of assembly |
| US10994112B2 (en) | 2014-02-05 | 2021-05-04 | Amgen Inc. | Drug delivery system with electromagnetic field generator |
| AU2015256082C1 (en) | 2014-05-07 | 2020-09-10 | Amgen Inc. | Autoinjector with shock reducing elements |
| CN111840696B (zh) | 2014-06-03 | 2022-12-20 | 安姆根有限公司 | 可控制药物递送系统和使用方法 |
| US10323088B2 (en) | 2014-09-22 | 2019-06-18 | Intrinsic Lifesciences Llc | Humanized anti-hepcidin antibodies and uses thereof |
| EP3206739B1 (en) | 2014-10-14 | 2021-12-01 | Amgen Inc. | Drug injection device with visual and audio indicators |
| EP3848072A1 (en) | 2014-12-19 | 2021-07-14 | Amgen Inc. | Drug delivery device with proximity sensor |
| US11357916B2 (en) | 2014-12-19 | 2022-06-14 | Amgen Inc. | Drug delivery device with live button or user interface field |
| JP6484345B2 (ja) | 2015-02-17 | 2019-03-20 | アムジエン・インコーポレーテツド | 固定及び／または戻りが真空によって支援された薬物送達装置 |
| WO2016138434A1 (en) | 2015-02-27 | 2016-09-01 | Amgen Inc. | Drug delivery device having a needle guard mechanism with a tunable threshold of resistance to needle guard movement |
| WO2017039786A1 (en) | 2015-09-02 | 2017-03-09 | Amgen Inc. | Syringe assembly adapter for a syringe |
| JP7082568B2 (ja) | 2015-12-09 | 2022-06-08 | アムジエン・インコーポレーテツド | 信号伝達キャップ付き自動注射器 |
| US11154661B2 (en) | 2016-01-06 | 2021-10-26 | Amgen Inc. | Auto-injector with signaling electronics |
| DK3429663T3 (da) | 2016-03-15 | 2020-09-28 | Amgen Inc | Reduktion af sandsynligheden for glasbrud i anordninger til indgivelse af lægemidler |
| CN105713880A (zh) * | 2016-04-20 | 2016-06-29 | 广东艾时代生物科技有限责任公司 | 一种造血干细胞体外扩增培养的无血清培养基及其应用 |
| WO2017189089A1 (en) | 2016-04-29 | 2017-11-02 | Amgen Inc. | Drug delivery device with messaging label |
| US11389588B2 (en) | 2016-05-02 | 2022-07-19 | Amgen Inc. | Syringe adapter and guide for filling an on-body injector |
| AU2017263558B2 (en) | 2016-05-13 | 2022-12-22 | Amgen Inc. | Vial sleeve assembly |
| WO2017200989A1 (en) | 2016-05-16 | 2017-11-23 | Amgen Inc. | Data encryption in medical devices with limited computational capability |
| US11541176B2 (en) | 2016-06-03 | 2023-01-03 | Amgen Inc. | Impact testing apparatuses and methods for drug delivery devices |
| EP3478342B1 (en) | 2016-07-01 | 2025-03-12 | Amgen Inc. | Drug delivery device having minimized risk of component fracture upon impact events |
| WO2018034784A1 (en) | 2016-08-17 | 2018-02-22 | Amgen Inc. | Drug delivery device with placement detection |
| US20200261643A1 (en) | 2016-10-25 | 2020-08-20 | Amgen Inc. | On-body injector |
| AU2018210301A1 (en) | 2017-01-17 | 2019-08-01 | Amgen Inc. | Injection devices and related methods of use and assembly |
| WO2018151890A1 (en) | 2017-02-17 | 2018-08-23 | Amgen Inc. | Drug delivery device with sterile fluid flowpath and related method of assembly |
| CA3052204A1 (en) | 2017-02-17 | 2018-08-23 | Amgen Inc. | Insertion mechanism for drug delivery device |
| EP3592403B1 (en) | 2017-03-06 | 2025-08-20 | Amgen Inc. | Drug delivery device with activation prevention feature |
| US11571511B2 (en) | 2017-03-07 | 2023-02-07 | Amgen Inc. | Insertion mechanism and method of inserting a needle of a drug delivery device |
| AU2018230486B2 (en) | 2017-03-09 | 2023-05-11 | Amgen Inc. | Insertion mechanism for drug delivery device |
| EP3570871B1 (en) | 2017-03-20 | 2020-11-18 | H. Hoffnabb-La Roche Ag | Method for in vitro glycoengineering of an erythropoiesis stimulating protein |
| ES3023742T3 (en) | 2017-03-28 | 2025-06-03 | Amgen Inc | Plunger rod and syringe assembly system |
| US11590294B2 (en) | 2017-06-08 | 2023-02-28 | Amgen Inc. | Syringe assembly for a drug delivery device and method of assembly |
| JP7200134B2 (ja) | 2017-06-08 | 2023-01-06 | アムジエン・インコーポレーテツド | トルク駆動式薬物送達デバイス |
| JP7195276B2 (ja) | 2017-06-22 | 2022-12-23 | アムジエン・インコーポレーテツド | デバイス起動による衝突／衝撃の低減 |
| WO2018237225A1 (en) | 2017-06-23 | 2018-12-27 | Amgen Inc. | Electronic drug delivery device comprising a cap activated by a switch assembly |
| IL270784B2 (en) | 2017-07-14 | 2023-11-01 | Amgen Inc | Needle insertion-extraction system with a double torsion spring system |
| JP7649105B2 (ja) | 2017-07-21 | 2025-03-19 | アムジエン・インコーポレーテツド | 薬物容器のためのガス透過性シーリング部材及び組立方法 |
| US11617837B2 (en) | 2017-07-25 | 2023-04-04 | Amgen Inc. | Drug delivery device with gear module and related method of assembly |
| MA49676A (fr) | 2017-07-25 | 2020-06-03 | Amgen Inc | Dispositif d'administration de médicament doté d'un système d'accès à un récipient et procédé d'assemblage associé |
| MA49838A (fr) | 2017-08-09 | 2020-06-17 | Amgen Inc | Systèm de administration de médicaments avec pression hydraulique-pneumatique de chambre |
| EP3668567B1 (en) | 2017-08-18 | 2026-02-18 | Amgen Inc. | Wearable injector with sterile adhesive patch |
| US11103636B2 (en) | 2017-08-22 | 2021-08-31 | Amgen Inc. | Needle insertion mechanism for drug delivery device |
| WO2019070472A1 (en) | 2017-10-04 | 2019-04-11 | Amgen Inc. | FLOW ADAPTER FOR MEDICATION DELIVERY DEVICE |
| ES2971450T3 (es) | 2017-10-06 | 2024-06-05 | Amgen Inc | Dispositivo de administración de fármacos con conjunto de enclavamiento y procedimiento de montaje correspondiente |
| US11464903B2 (en) | 2017-10-09 | 2022-10-11 | Amgen Inc. | Drug delivery device with drive assembly and related method of assembly |
| IL273582B2 (en) | 2017-11-03 | 2024-12-01 | Amgen Inc | Systems and approaches for sterilizing a drug delivery device |
| EP3706830B1 (en) | 2017-11-06 | 2024-08-07 | Amgen Inc. | Drug delivery device with placement and flow sensing |
| EP3707075A1 (en) | 2017-11-06 | 2020-09-16 | Amgen Inc. | Fill-finish assemblies and related methods |
| MA50557A (fr) | 2017-11-10 | 2020-09-16 | Amgen Inc | Pistons pour dispositifs d'administration de médicament |
| MX2020005066A (es) | 2017-11-16 | 2020-08-20 | Amgen Inc | Autoinyector con deteccion de detencion y punto final. |
| JP7370969B2 (ja) | 2017-11-16 | 2023-10-30 | アムジエン・インコーポレーテツド | 薬物送達デバイスの扉ラッチ機構 |
| CN108129561B (zh) * | 2017-12-06 | 2021-05-25 | 渤海大学 | 一种ace抑制肽 |
| US10835685B2 (en) | 2018-05-30 | 2020-11-17 | Amgen Inc. | Thermal spring release mechanism for a drug delivery device |
| US11083840B2 (en) | 2018-06-01 | 2021-08-10 | Amgen Inc. | Modular fluid path assemblies for drug delivery devices |
| WO2020023336A1 (en) | 2018-07-24 | 2020-01-30 | Amgen Inc. | Hybrid drug delivery devices with grip portion |
| US12303677B2 (en) | 2018-07-24 | 2025-05-20 | Amgen Inc. | Hybrid drug delivery devices with optional grip portion and related method of preparation |
| MA53375A (fr) | 2018-07-24 | 2021-06-02 | Amgen Inc | Dispositifs d'administration pour l'administration de médicaments |
| CA3103681A1 (en) | 2018-07-24 | 2020-01-30 | Amgen Inc. | Delivery devices for administering drugs |
| CA3103105A1 (en) | 2018-07-31 | 2020-02-06 | Amgen Inc. | Fluid path assembly for a drug delivery device |
| US20210346601A1 (en) | 2018-09-24 | 2021-11-11 | Amgen Inc. | Interventional dosing systems and methods |
| CA3110371A1 (en) | 2018-09-28 | 2020-04-02 | Amgen Inc. | Muscle wire escapement activation assembly for a drug delivery device |
| EP3860685A1 (en) | 2018-10-02 | 2021-08-11 | Amgen Inc. | Injection systems for drug delivery with internal force transmission |
| US12151089B2 (en) | 2018-10-05 | 2024-11-26 | Amgen Inc. | Drug delivery device having dose indicator |
| WO2020081480A1 (en) | 2018-10-15 | 2020-04-23 | Amgen Inc. | Platform assembly process for drug delivery device |
| TW202541859A (zh) | 2018-10-15 | 2025-11-01 | 美商安進公司 | 具有阻尼機構之藥物遞送裝置及自動注射器 |
| MA54048A (fr) | 2018-11-01 | 2022-02-09 | Amgen Inc | Dispositifs d'administration de médicament avec rétraction partielle de l'organe d'administration de médicament |
| TWI831847B (zh) | 2018-11-01 | 2024-02-11 | 美商安進公司 | 部分針頭縮回之藥物遞送裝置及其操作方法 |
| EP3873563A1 (en) | 2018-11-01 | 2021-09-08 | Amgen Inc. | Drug delivery devices with partial drug delivery member retraction |
| AU2020263289B2 (en) | 2019-04-24 | 2025-05-22 | Amgen Inc. | Syringe sterilization verification assemblies and methods |
| WO2021041067A2 (en) | 2019-08-23 | 2021-03-04 | Amgen Inc. | Drug delivery device with configurable needle shield engagement components and related methods |
| JP2024523779A (ja) | 2021-05-21 | 2024-07-02 | アムジェン インコーポレイテッド | 薬物容器用の充填レシピを最適化する方法 |
| WO2024094457A1 (en) | 2022-11-02 | 2024-05-10 | F. Hoffmann-La Roche Ag | Method for producing glycoprotein compositions |
| WO2026030152A1 (en) | 2024-07-29 | 2026-02-05 | Amgen Inc. | System and method for assessing transferability of a fill recipe |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1621554T4 (da) * | 1992-08-21 | 2012-12-17 | Univ Bruxelles | Immunoglobuliner blottet for lette kæder |
| PE27997A1 (es) * | 1994-04-29 | 1997-09-20 | Lilly Co Eli | Antagonistas de receptores de taquicininas |
| US6660843B1 (en) * | 1998-10-23 | 2003-12-09 | Amgen Inc. | Modified peptides as therapeutic agents |
| IL142917A0 (en) * | 1998-11-03 | 2002-04-21 | Basf Ag | Substituted 2-phenylbenzimidazoles, the production thereof and their use |
| DE19920936A1 (de) * | 1999-05-07 | 2000-11-09 | Basf Ag | Heterozyklisch substituierte Benzimidazole, deren Herstellung und Anwendung |
| JP2003531588A (ja) * | 2000-04-11 | 2003-10-28 | ジェネンテック・インコーポレーテッド | 多価抗体とその用途 |
| ATE320450T1 (de) * | 2000-12-05 | 2006-04-15 | Alexion Pharma Inc | Rationell entworfene antikörper |
| EP1373204B1 (en) * | 2001-03-09 | 2016-10-26 | Janssen Pharmaceuticals, Inc. | Heterocyclic compounds |
| CA2490409A1 (en) * | 2002-06-28 | 2004-01-08 | Centocor, Inc. | Mammalian ch1 deleted mimetibodies, compositions, methods and uses |
| US7241733B2 (en) * | 2002-06-28 | 2007-07-10 | Centocor, Inc. | Mammalian EPO mimetic CH1 deleted mimetibodies, compositions, methods and uses |
| WO2005005604A2 (en) * | 2003-06-30 | 2005-01-20 | Centocor, Inc. | Engineered anti-target immunoglobulin derived proteins, compositions, methods and uses |
-
2004
- 2004-09-29 EP EP04821516A patent/EP1687452A4/en not_active Withdrawn
- 2004-09-29 US US10/953,613 patent/US20060127404A1/en not_active Abandoned
- 2004-09-29 AU AU2004316266A patent/AU2004316266A1/en not_active Abandoned
- 2004-09-29 CN CNA2004800353031A patent/CN1890383A/zh active Pending
- 2004-09-29 WO PCT/US2004/031858 patent/WO2005081687A2/en not_active Ceased
- 2004-09-29 JP JP2006534029A patent/JP4767857B2/ja not_active Expired - Fee Related
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