JP2010520883A5 - - Google Patents
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- Publication number
- JP2010520883A5 JP2010520883A5 JP2009552910A JP2009552910A JP2010520883A5 JP 2010520883 A5 JP2010520883 A5 JP 2010520883A5 JP 2009552910 A JP2009552910 A JP 2009552910A JP 2009552910 A JP2009552910 A JP 2009552910A JP 2010520883 A5 JP2010520883 A5 JP 2010520883A5
- Authority
- JP
- Japan
- Prior art keywords
- benzo
- chloro
- diazepin
- compound
- hydroxyphenyl
- 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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- 150000001875 compounds Chemical class 0.000 claims description 96
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 208000037976 chronic inflammation Diseases 0.000 claims description 5
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 5
- 230000003463 hyperproliferative effect Effects 0.000 claims description 5
- 208000026278 immune system disease Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- IIPUDAGCAJCTJT-UHFFFAOYSA-N 1-[4-[3-[(2-bromophenyl)methyl]-7-chloro-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-(2,2,2-trifluoroethyl)urea Chemical compound C1=CC(NC(=O)NCC(F)(F)F)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Br IIPUDAGCAJCTJT-UHFFFAOYSA-N 0.000 claims description 2
- NMVPSAGRKCQZAO-UHFFFAOYSA-N 1-[4-[3-[(2-bromophenyl)methyl]-7-chloro-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-(2-ethoxyethyl)urea Chemical compound C1=CC(NC(=O)NCCOCC)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Br NMVPSAGRKCQZAO-UHFFFAOYSA-N 0.000 claims description 2
- USKLYLPLUIQWAE-UHFFFAOYSA-N 1-[4-[3-[(2-bromophenyl)methyl]-7-chloro-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-(2-methoxyethyl)urea Chemical compound C1=CC(NC(=O)NCCOC)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Br USKLYLPLUIQWAE-UHFFFAOYSA-N 0.000 claims description 2
- HCKMKLZNSAJPHB-UHFFFAOYSA-N 1-[4-[3-[(2-bromophenyl)methyl]-7-chloro-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Br HCKMKLZNSAJPHB-UHFFFAOYSA-N 0.000 claims description 2
- RVCIYVSHZIOGRJ-UHFFFAOYSA-N 1-[4-[3-[(2-bromophenyl)methyl]-7-chloro-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-cyclopropylurea Chemical compound N1=C(C=2C=CC(NC(=O)NC3CC3)=CC=2)C2=CC(Cl)=CC=C2NC(=O)C1CC1=CC=CC=C1Br RVCIYVSHZIOGRJ-UHFFFAOYSA-N 0.000 claims description 2
- UPOUEZGGMHDDLU-UHFFFAOYSA-N 1-[4-[3-[(2-bromophenyl)methyl]-7-chloro-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Br UPOUEZGGMHDDLU-UHFFFAOYSA-N 0.000 claims description 2
- RKEJHLBRBBLNGU-UHFFFAOYSA-N 1-[4-[3-[(2-bromophenyl)methyl]-7-chloro-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Br RKEJHLBRBBLNGU-UHFFFAOYSA-N 0.000 claims description 2
- IYEWOSIFWULNJW-UHFFFAOYSA-N 1-[4-[7-chloro-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1C(F)(F)F IYEWOSIFWULNJW-UHFFFAOYSA-N 0.000 claims description 2
- RILPJCZZSPPAFK-UHFFFAOYSA-N 1-[4-[7-chloro-3-[(2-chlorophenyl)methyl]-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-(2,2,2-trifluoroethyl)urea Chemical compound C1=CC(NC(=O)NCC(F)(F)F)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Cl RILPJCZZSPPAFK-UHFFFAOYSA-N 0.000 claims description 2
- AWCBPHDNEGSDOS-UHFFFAOYSA-N 1-[4-[7-chloro-3-[(2-chlorophenyl)methyl]-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-(2-ethoxyethyl)urea Chemical compound C1=CC(NC(=O)NCCOCC)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Cl AWCBPHDNEGSDOS-UHFFFAOYSA-N 0.000 claims description 2
- QBXAKSGMQRBMBA-UHFFFAOYSA-N 1-[4-[7-chloro-3-[(2-chlorophenyl)methyl]-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-(2-methoxyethyl)urea Chemical compound C1=CC(NC(=O)NCCOC)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Cl QBXAKSGMQRBMBA-UHFFFAOYSA-N 0.000 claims description 2
- AZFRGWONNFCVRF-UHFFFAOYSA-N 1-[4-[7-chloro-3-[(2-chlorophenyl)methyl]-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Cl AZFRGWONNFCVRF-UHFFFAOYSA-N 0.000 claims description 2
- BCBRDNOCFGVWAJ-UHFFFAOYSA-N 1-[4-[7-chloro-3-[(2-chlorophenyl)methyl]-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-cyclopropylurea Chemical compound N1=C(C=2C=CC(NC(=O)NC3CC3)=CC=2)C2=CC(Cl)=CC=C2NC(=O)C1CC1=CC=CC=C1Cl BCBRDNOCFGVWAJ-UHFFFAOYSA-N 0.000 claims description 2
- XQGKJKRNVYTZEM-UHFFFAOYSA-N 1-[4-[7-chloro-3-[(2-chlorophenyl)methyl]-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Cl XQGKJKRNVYTZEM-UHFFFAOYSA-N 0.000 claims description 2
- YRCGSLGQXMMZBM-UHFFFAOYSA-N 1-[4-[7-chloro-3-[(2-chlorophenyl)methyl]-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Cl YRCGSLGQXMMZBM-UHFFFAOYSA-N 0.000 claims description 2
- WTNMIAIEWNPWTJ-UHFFFAOYSA-N 1-[4-[7-chloro-3-[(2-fluorophenyl)methyl]-2-oxo-1,3-dihydro-1,4-benzodiazepin-5-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1F WTNMIAIEWNPWTJ-UHFFFAOYSA-N 0.000 claims description 2
- RMYPRFPKXOHANH-UHFFFAOYSA-N 3-[(2-bromophenyl)methyl]-7-chloro-1-methyl-5-(2-oxo-1,3-dihydrobenzimidazol-5-yl)-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=C3NC(=O)NC3=CC=2)=NC1CC1=CC=CC=C1Br RMYPRFPKXOHANH-UHFFFAOYSA-N 0.000 claims description 2
- APNWNPCBUGCQDM-UHFFFAOYSA-N 3-[(2-bromophenyl)methyl]-7-chloro-5-(4-hydroxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(O)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Br APNWNPCBUGCQDM-UHFFFAOYSA-N 0.000 claims description 2
- BHEIEROWUGRDAE-UHFFFAOYSA-N 3-[(3-bromophenyl)methyl]-7-chloro-5-(4-hydroxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=CC(Br)=C1 BHEIEROWUGRDAE-UHFFFAOYSA-N 0.000 claims description 2
- XTSXGBWEVIYXHY-UHFFFAOYSA-N 3-[(4-bromophenyl)methyl]-7-chloro-5-(4-hydroxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=C(Br)C=C1 XTSXGBWEVIYXHY-UHFFFAOYSA-N 0.000 claims description 2
- -1 4-ethylbenzyl Chemical group 0.000 claims description 2
- YYQYFWOSIYYOMC-UHFFFAOYSA-N 7-chloro-1-methyl-5-(2-oxo-1,3-dihydrobenzimidazol-5-yl)-3-[[2-(trifluoromethyl)phenyl]methyl]-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=C3NC(=O)NC3=CC=2)=NC1CC1=CC=CC=C1C(F)(F)F YYQYFWOSIYYOMC-UHFFFAOYSA-N 0.000 claims description 2
- XZJYPOHRBGVXAI-UHFFFAOYSA-N 7-chloro-3-[(2-chlorophenyl)methyl]-1-methyl-5-(2-oxo-1,3-dihydrobenzimidazol-5-yl)-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=C3NC(=O)NC3=CC=2)=NC1CC1=CC=CC=C1Cl XZJYPOHRBGVXAI-UHFFFAOYSA-N 0.000 claims description 2
- ZGZVMAWYHZQCRZ-UHFFFAOYSA-N 7-chloro-3-[(2-chlorophenyl)methyl]-5-(2-oxo-1,3-dihydrobenzimidazol-5-yl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N1=C(C=2C=C3NC(=O)NC3=CC=2)C2=CC(Cl)=CC=C2NC(=O)C1CC1=CC=CC=C1Cl ZGZVMAWYHZQCRZ-UHFFFAOYSA-N 0.000 claims description 2
- JTBVZGDNQXYPCR-UHFFFAOYSA-N 7-chloro-3-[(2-chlorophenyl)methyl]-5-(4-hydroxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(O)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC1CC1=CC=CC=C1Cl JTBVZGDNQXYPCR-UHFFFAOYSA-N 0.000 claims description 2
- UVCHKOCUFMZNNB-UHFFFAOYSA-N 7-chloro-3-[(2-chlorophenyl)methyl]-5-(4-hydroxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=CC=C1Cl UVCHKOCUFMZNNB-UHFFFAOYSA-N 0.000 claims description 2
- PVUVANBISCVCOM-UHFFFAOYSA-N 7-chloro-3-[(2-ethylphenyl)methyl]-5-(4-hydroxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound CCC1=CC=CC=C1CC1C(=O)NC2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=N1 PVUVANBISCVCOM-UHFFFAOYSA-N 0.000 claims description 2
- WPYWLRHNKPPWEU-UHFFFAOYSA-N 7-chloro-3-[(2-ethylphenyl)methyl]-5-(4-hydroxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound CCC1=CC=CC=C1CC1C(=O)N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=N1 WPYWLRHNKPPWEU-UHFFFAOYSA-N 0.000 claims description 2
- OZVCPHZRQFZEPC-UHFFFAOYSA-N 7-chloro-3-[(3-chlorophenyl)methyl]-5-(4-hydroxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=CC(Cl)=C1 OZVCPHZRQFZEPC-UHFFFAOYSA-N 0.000 claims description 2
- YPAAOOCDZWKTEU-UHFFFAOYSA-N 7-chloro-3-[(3-ethylphenyl)methyl]-5-(4-hydroxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound CCC1=CC=CC(CC2C(NC3=CC=C(Cl)C=C3C(C=3C=CC(O)=CC=3)=N2)=O)=C1 YPAAOOCDZWKTEU-UHFFFAOYSA-N 0.000 claims description 2
- YVCRFYMQQAMLID-UHFFFAOYSA-N 7-chloro-3-[(3-ethylphenyl)methyl]-5-(4-hydroxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound CCC1=CC=CC(CC2C(N(C)C3=CC=C(Cl)C=C3C(C=3C=CC(O)=CC=3)=N2)=O)=C1 YVCRFYMQQAMLID-UHFFFAOYSA-N 0.000 claims description 2
- CIBBQTOJJGTKSM-UHFFFAOYSA-N 7-chloro-3-[(4-ethylphenyl)methyl]-5-(4-hydroxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound C1=CC(CC)=CC=C1CC1C(=O)N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=N1 CIBBQTOJJGTKSM-UHFFFAOYSA-N 0.000 claims description 2
- AGKQFJGZZBWCLE-UHFFFAOYSA-N 7-chloro-5-(2-oxo-1,3-dihydrobenzimidazol-5-yl)-3-[[2-(trifluoromethyl)phenyl]methyl]-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound FC(F)(F)C1=CC=CC=C1CC1C(=O)NC2=CC=C(Cl)C=C2C(C=2C=C3NC(=O)NC3=CC=2)=N1 AGKQFJGZZBWCLE-UHFFFAOYSA-N 0.000 claims description 2
- HRERBCNMDASXRB-UHFFFAOYSA-N 7-chloro-5-(4-hydroxyphenyl)-1-methyl-3-[(2-methylphenyl)methyl]-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=CC=C1C HRERBCNMDASXRB-UHFFFAOYSA-N 0.000 claims description 2
- KQQDGGVZYWABFP-UHFFFAOYSA-N 7-chloro-5-(4-hydroxyphenyl)-1-methyl-3-[(3-methylphenyl)methyl]-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=CC(C)=C1 KQQDGGVZYWABFP-UHFFFAOYSA-N 0.000 claims description 2
- HTZZWVDRLYDVIG-UHFFFAOYSA-N 7-chloro-5-(4-hydroxyphenyl)-1-methyl-3-[(3-propan-2-ylphenyl)methyl]-3H-1,4-benzodiazepin-2-one Chemical compound CC(C)C1=CC=CC(CC2C(N(C)C3=CC=C(Cl)C=C3C(C=3C=CC(O)=CC=3)=N2)=O)=C1 HTZZWVDRLYDVIG-UHFFFAOYSA-N 0.000 claims description 2
- QNRAEQBQEZHFAT-UHFFFAOYSA-N 7-chloro-5-(4-hydroxyphenyl)-1-methyl-3-[(4-methylphenyl)methyl]-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=C(C)C=C1 QNRAEQBQEZHFAT-UHFFFAOYSA-N 0.000 claims description 2
- DNHFEIXHDNENEF-UHFFFAOYSA-N 7-chloro-5-(4-hydroxyphenyl)-1-methyl-3-[(4-propan-2-ylphenyl)methyl]-3H-1,4-benzodiazepin-2-one Chemical compound C1=CC(C(C)C)=CC=C1CC1C(=O)N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=N1 DNHFEIXHDNENEF-UHFFFAOYSA-N 0.000 claims description 2
- XXZXKAGVVMTDKS-UHFFFAOYSA-N 7-chloro-5-(4-hydroxyphenyl)-1-methyl-3-[[2-(trifluoromethyl)phenyl]methyl]-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=CC=C1C(F)(F)F XXZXKAGVVMTDKS-UHFFFAOYSA-N 0.000 claims description 2
- SDIKDRVKXGQSCM-UHFFFAOYSA-N 7-chloro-5-(4-hydroxyphenyl)-1-methyl-3-[[4-(trifluoromethyl)phenyl]methyl]-3H-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=NC1CC1=CC=C(C(F)(F)F)C=C1 SDIKDRVKXGQSCM-UHFFFAOYSA-N 0.000 claims description 2
- GSBGGYFOSSNZKL-UHFFFAOYSA-N 7-chloro-5-(4-hydroxyphenyl)-3-[(2-methylphenyl)methyl]-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound CC1=CC=CC=C1CC1C(=O)NC2=CC=C(Cl)C=C2C(C=2C=CC(O)=CC=2)=N1 GSBGGYFOSSNZKL-UHFFFAOYSA-N 0.000 claims description 2
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| US20060025388A1 (en) * | 1999-04-30 | 2006-02-02 | Glick Gary D | Compositions and methods relating to novel compounds and targets thereof |
| US20050272723A1 (en) * | 2004-04-27 | 2005-12-08 | The Regents Of The University Of Michigan | Methods and compositions for treating diseases and conditions associated with mitochondrial function |
| US20060052369A1 (en) * | 2004-09-07 | 2006-03-09 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
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| US7759338B2 (en) * | 2006-04-27 | 2010-07-20 | The Regents Of The University Of Michigan | Soluble 1,4 benzodiazepine compounds and stable salts thereof |
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