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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Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20050113460A1 (en) * | 1999-04-30 | 2005-05-26 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| JP5127096B2 (ja) * | 1999-04-30 | 2013-01-23 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | アポトーシスにより誘導される自己免疫疾患を処置するためのベンゾジアゼピンの使用 |
| US7144880B2 (en) * | 1999-04-30 | 2006-12-05 | Regents Of The University Of Michigan | Compositions relating to novel compounds and targets thereof |
| 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 |
| JP2008545757A (ja) * | 2005-06-01 | 2008-12-18 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 溶媒和されていないベンゾジアゼピン組成物および方法 |
| US20070105844A1 (en) * | 2005-10-26 | 2007-05-10 | Regents Of The University Of Michigan | Therapeutic compositions and methods |
| EP1948191B1 (en) * | 2005-11-01 | 2013-01-16 | The Regents of the University of Michigan | Novel 1,4-benzodiazepine-2,5-diones with therapeutic properties |
| US7759338B2 (en) * | 2006-04-27 | 2010-07-20 | The Regents Of The University Of Michigan | Soluble 1,4 benzodiazepine compounds and stable salts thereof |
| EP2418206A3 (en) * | 2006-06-09 | 2012-06-27 | The Regents of the University of Michigan | Benzodiazepine derivatives useful in the treatment of autoimmune disorders |
| KR101164718B1 (ko) * | 2007-03-09 | 2012-07-11 | 더 리젠츠 오브 더 유니버시티 오브 미시간 | 신규 화합물 및 이의 표적에 관한 조성물 및 방법 |
| MX2010002732A (es) * | 2007-09-14 | 2010-06-02 | Univ Michigan | Inhibidores de f1f0-atpasa y metodos relacionados. |
| CN101918375A (zh) | 2007-11-06 | 2010-12-15 | 密歇根大学董事会 | 在皮肤病症的治疗中有用的苯并二氮杂*酮化合物 |
| US8497307B2 (en) | 2008-09-11 | 2013-07-30 | The Regents Of The University Of Michigan | Aryl guanidine F1F0-ATPase inhibitors and related methods |
| WO2010121164A2 (en) | 2009-04-17 | 2010-10-21 | The Regents Of The University Of Michigan | 1,4-benzodiazepinone compounds and their use in treating cancer |
| WO2011022652A1 (en) | 2009-08-21 | 2011-02-24 | Novan, Inc. | Topical gels |
| EP2470020A4 (en) * | 2009-09-18 | 2013-03-13 | Univ Michigan | BENZODIAZEPINONE COMPOUNDS AND TREATMENT METHODS THEREWITH |
| WO2011062765A2 (en) | 2009-11-17 | 2011-05-26 | The Regents Of The University Of Michigan | 1,4-benzodiazepine-2,5-diones and related compounds with therapeutic properties |
| JP5856064B2 (ja) | 2009-11-17 | 2016-02-09 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 治療特性を有する１，４−ベンゾジアゼピン−２，５−ジオンおよび関連化合物 |
| US8591876B2 (en) | 2010-12-15 | 2013-11-26 | Novan, Inc. | Methods of decreasing sebum production in the skin |
| US20150111973A1 (en) * | 2012-03-13 | 2015-04-23 | Novan, Inc. | Methods of modulating steroid hormone activity |
| JP6280546B2 (ja) | 2012-06-26 | 2018-02-14 | デル マー ファーマシューティカルズ | ジアンヒドロガラクチトール、ジアセチルジアンヒドロガラクチトール、ジブロモズルシトール、又はこれらの類似体若しくは誘導体を用いた、遺伝子多型又はａｈｉ１の調節不全若しくは変異を有する患者におけるチロシンキナーゼインヒビター抵抗性悪性腫瘍を処置するための方法 |
| KR20160061911A (ko) | 2013-04-08 | 2016-06-01 | 데니스 엠. 브라운 | 최적하 투여된 화학 화합물의 치료 효과 |
| CN103724207B (zh) * | 2013-12-20 | 2016-07-06 | 北京智博高科生物技术有限公司 | 苯基苄基醚类衍生物及其制备方法和应用 |
| US11537690B2 (en) | 2019-05-07 | 2022-12-27 | The Nielsen Company (Us), Llc | End-point media watermarking |
Family Cites Families (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU11248A1 (ru) | 1927-03-29 | 1929-09-30 | В.С. Григорьев | Способ очистки антрацена |
| FR900482A (fr) | 1942-12-17 | 1945-06-29 | Fides Gmbh | Condensateur électrostatique avec diélectrique consistant au moins partiellement en produits de transformation non conducteurs d'une armature |
| US2457405A (en) | 1945-09-25 | 1948-12-28 | Monsanto Chemicals | Halo nitroparaffin modified aminoplasts |
| FR66979E (fr) | 1953-06-22 | 1957-11-04 | Glaenzer Spicer Sa | Support pour arbre rotatif |
| US3374264A (en) * | 1962-10-04 | 1968-03-19 | Hoffmann La Roche | N-haloacetyl-anthranilic acids and esters |
| US3261828A (en) | 1962-10-04 | 1966-07-19 | Hoffmann La Roche | 3h-1,4-benzodiazepine-2,5(1h,4h)-dione compounds |
| US3384635A (en) | 1966-09-28 | 1968-05-21 | Sterling Drug Inc | 1, 4-benzodiazepine derivatives |
| US3415814A (en) | 1966-09-28 | 1968-12-10 | Sterling Drug Inc | 4-(cyclopropylmethyl)-3h-1,4-benzodiazepine-2,5(1h,4h)-dione |
| AT280290B (de) | 1967-11-24 | 1970-04-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen 1-Phenyl-4-alkyl-3H-1,4-benzodiazepin-2,5-[1H,4H]-dionen |
| USRE30293E (en) | 1969-03-18 | 1980-06-03 | Knoll A.G. | Process for preparing 1,5-benzodiazepine-2-ones |
| US4108852A (en) | 1969-03-18 | 1978-08-22 | Knoll Ag. | Process for preparing 1,5-benzodiazepine-2-ones |
| GB1363735A (en) | 1970-10-23 | 1974-08-14 | Hoechst Ag | Process for the manufacture of benzimidazolones |
| GB1324469A (en) | 1970-10-28 | 1973-07-25 | Knoll Ag | Derivatives of benzodiazepines |
| ZA7468B (en) | 1973-01-16 | 1974-11-27 | J Voorhees | Compositions and treatment of proliferatave skin diseases with phosphodiesterase inhibitors |
| IE38931B1 (en) | 1973-03-09 | 1978-07-05 | Lipha | Triazolobenzodiazepines |
| US4076823A (en) | 1977-08-18 | 1978-02-28 | E. R. Squibb & Sons, Inc. | Triazolo-2,4-benzodiazepines |
| US4495101A (en) | 1983-04-28 | 1985-01-22 | American Home Products Corporation | Antiinflammatory 5H-tetrazolo (5,1-c)(1,4)benzodiazepine derivatives |
| US4551480A (en) | 1983-06-21 | 1985-11-05 | Stiefel Laboratories, Inc. | Compositions for the treatment of psoriasis |
| US4894366A (en) | 1984-12-03 | 1990-01-16 | Fujisawa Pharmaceutical Company, Ltd. | Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same |
| US4820834A (en) | 1984-06-26 | 1989-04-11 | Merck & Co., Inc. | Benzodiazepine analogs |
| US5004741A (en) | 1984-06-26 | 1991-04-02 | Merck & Co., Inc. | Methods of antagonizing CCK or gastrin with benzodiazepine analogs |
| DE3435974A1 (de) | 1984-10-01 | 1986-04-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Diazepine enthaltende pharmazeutische zusammensetzungen mit paf-antagonistischer wirkung |
| FR2591596B1 (fr) | 1985-12-13 | 1988-09-09 | Roussel Uclaf | Nouvelles 4h-triazolo(4,3-a)(1,4)benzodiazepines, leur procede de preparation, leur application comme medicaments et les compositions les renfermant |
| GB8608080D0 (en) | 1986-04-02 | 1986-05-08 | Fujisawa Pharmaceutical Co | Solid dispersion composition |
| US4946778A (en) | 1987-09-21 | 1990-08-07 | Genex Corporation | Single polypeptide chain binding molecules |
| US4751223A (en) | 1986-10-14 | 1988-06-14 | Hoechst-Roussel Pharmaceuticals, Inc. | Antiinflammatory and analgesic aminoalkyl tetracyclic benzodiazepines |
| US4898861A (en) | 1987-03-26 | 1990-02-06 | Hoffmann-La Roche Inc. | Method for inhibiting the proliferation of tumor cells |
| US5147872A (en) * | 1987-06-09 | 1992-09-15 | Golwyn Daniel H | Treatment of immunologically based disorders, specifically psoriasis |
| US4886062A (en) | 1987-10-19 | 1989-12-12 | Medtronic, Inc. | Intravascular radially expandable stent and method of implant |
| US4970207A (en) | 1988-07-07 | 1990-11-13 | Fujisawa Pharmaceutical Company, Ltd. | Benzodiazepine derivatives |
| SE8804074D0 (sv) | 1988-11-10 | 1988-11-10 | Pharmacia Ab | Sensorenhet och dess anvaendning i biosensorsystem |
| US5501959A (en) | 1989-01-17 | 1996-03-26 | Alamar Biosciences Laboratory, Inc. | Antibiotic and cytotoxic drug susceptibility assays using resazurin and poising agents |
| WO1990013332A1 (en) | 1989-05-11 | 1990-11-15 | Cedars-Sinai Medical Center | Stent with sustained drug delivery |
| US5258510A (en) | 1989-10-20 | 1993-11-02 | Otsuka Pharma Co Ltd | Benzoheterocyclic compounds |
| US5041438A (en) | 1989-10-30 | 1991-08-20 | Hoffmann-La Roche Inc. | Method for treating retroviral infections with benzodiazepine compounds |
| US5324726A (en) | 1989-12-18 | 1994-06-28 | Merck & Co., Inc. | Benzodiazepine analogs |
| DE69110787T2 (de) | 1990-02-28 | 1996-04-04 | Medtronic, Inc., Minneapolis, Minn. | Intraluminale prothese mit wirkstoffeluierung. |
| ATE145208T1 (de) | 1990-07-06 | 1996-11-15 | Yoshitomi Pharmaceutical | Kondensierte thiophenverbindungen und deren verwendung |
| BR9200951A (pt) | 1991-03-21 | 1992-11-17 | Hoffmann La Roche | Compostos, processo para sua producao,preparacoes farmaceuticas e uso |
| EP0637308A1 (en) | 1992-03-16 | 1995-02-08 | MERCK SHARP & DOHME LTD. | Benzodiazepine derivatives, compositions containing them and their use in therapy |
| US5599352A (en) | 1992-03-19 | 1997-02-04 | Medtronic, Inc. | Method of making a drug eluting stent |
| US5288514A (en) | 1992-09-14 | 1994-02-22 | The Regents Of The University Of California | Solid phase and combinatorial synthesis of benzodiazepine compounds on a solid support |
| GB9307527D0 (en) | 1993-04-13 | 1993-06-02 | Fujisawa Pharmaceutical Co | New venzamide derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
| US5391566A (en) * | 1993-07-20 | 1995-02-21 | Merck & Co., Inc. | Benzimidazolinones substituted with phenoxyphenylacetic acid derivatives |
| WO1996005827A1 (en) | 1994-08-18 | 1996-02-29 | Merck & Co., Inc. | N-2,3-dihydro-1-(2-propyl)-2-oxo-5-phenyl-1h-1,4-benzodiazepines |
| US6524832B1 (en) | 1994-02-04 | 2003-02-25 | Arch Development Corporation | DNA damaging agents in combination with tyrosine kinase inhibitors |
| US5444092A (en) | 1994-07-20 | 1995-08-22 | Collins; Jerry | Method and composition for treating psoriasis |
| JPH10504545A (ja) * | 1994-07-29 | 1998-05-06 | 藤沢薬品工業株式会社 | ベンゾジアゼピン誘導体 |
| US5618792A (en) | 1994-11-21 | 1997-04-08 | Cortech, Inc. | Substituted heterocyclic compounds useful as inhibitors of (serine proteases) human neutrophil elastase |
| US5677282A (en) | 1995-06-07 | 1997-10-14 | Proscript, Inc. | Amino acid amides of 1,3,4-thiadiazoles as matrix metalloproteinase |
| US5962337A (en) | 1995-06-29 | 1999-10-05 | Pharmacopeia, Inc. | Combinatorial 1,4-benzodiazepin-2,5-dione library |
| RU2096044C1 (ru) | 1995-07-19 | 1997-11-20 | Малое предприятие "Ветта" | Ветеринарный имплантируемый препарат для регулирования биологического ритма животных |
| US5776946A (en) | 1995-08-28 | 1998-07-07 | Mcgeer; Patrick L. | Peripheral benzodiazepine receptor ligands as antiinflammatory agents |
| JP2001520636A (ja) | 1995-08-30 | 2001-10-30 | ザ リージェンツ オブ ザ ユニバーシティー オブ カリフォルニア | 慢性炎症性疾患における細胞蓄積の治療 |
| CA2233012A1 (en) | 1995-09-21 | 1997-03-27 | Koichi Shudo | Compounds enhancing the activity of retinoids |
| US6579854B1 (en) | 1996-08-14 | 2003-06-17 | Vanderbilt University | Diagnosis and management of infection caused by chlamydia |
| US7351421B2 (en) | 1996-11-05 | 2008-04-01 | Hsing-Wen Sung | Drug-eluting stent having collagen drug carrier chemically treated with genipin |
| PT945445E (pt) | 1996-12-10 | 2004-01-30 | Zeria Pharm Co Ltd | Derivados de 1,5-benzodiazepina |
| US6074859A (en) | 1997-07-08 | 2000-06-13 | Kikkoman Corporation | Mutant-type bioluminescent protein, and process for producing the mutant-type bioluminescent protein |
| US6080568A (en) | 1997-08-19 | 2000-06-27 | Genencor International, Inc. | Mutant α-amylase comprising modification at residues corresponding to A210, H405 and/or T412 in Bacillus licheniformis |
| AU750245B2 (en) | 1997-10-08 | 2002-07-11 | Aurinia Phamaceuticals Inc. | Deuterated cyclosporine analogs and their use as immunomodulating agents |
| US6100254A (en) | 1997-10-10 | 2000-08-08 | Board Of Regents, The University Of Texas System | Inhibitors of protein tyrosine kinases |
| US6206914B1 (en) | 1998-04-30 | 2001-03-27 | Medtronic, Inc. | Implantable system with drug-eluting cells for on-demand local drug delivery |
| FR2779963A1 (fr) | 1998-06-22 | 1999-12-24 | Centre Nat Rech Scient | Utilisation d'un compose possedant une affinite pour le recepteur mitochondrial des benzodiazepines en therapie du cancer |
| US6277844B1 (en) | 1998-09-14 | 2001-08-21 | Sydney Spector | Compound for selective treatment of malignant cells by inhibiting cell cycle progression, decreasing Bcl2, and increasing apoptosis |
| US20030044776A1 (en) | 1998-09-25 | 2003-03-06 | James A. Dykens | Compositions and methods for identifying agents that alter mitochondrial permeability transition pores |
| FR2785803B1 (fr) | 1998-11-17 | 2005-03-25 | Sanofi Sa | Utilisation d'une substance se liant au recepteur peripherique des benzodiazepines dans le traitement des stress cutanes |
| US7175953B2 (en) | 1999-04-09 | 2007-02-13 | Institute Fuer Diagnostik Forschung | Short-warp peptide-dye conjugate as contrast agent for optical diagnostic |
| US20040176358A1 (en) | 1999-04-30 | 2004-09-09 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| US20050113460A1 (en) | 1999-04-30 | 2005-05-26 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| US7144880B2 (en) | 1999-04-30 | 2006-12-05 | Regents Of The University Of Michigan | Compositions relating to novel compounds and targets thereof |
| JP5127096B2 (ja) | 1999-04-30 | 2013-01-23 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | アポトーシスにより誘導される自己免疫疾患を処置するためのベンゾジアゼピンの使用 |
| US20060025388A1 (en) * | 1999-04-30 | 2006-02-02 | Glick Gary D | Compositions and methods relating to novel compounds and targets thereof |
| US20030119029A1 (en) | 1999-04-30 | 2003-06-26 | Regents Of The University Of Michigan | Compositions and methods relating to novel benzodiazepine compounds and targets thereof |
| US7276348B2 (en) * | 1999-04-30 | 2007-10-02 | Regents Of The University Of Michigan | Compositions and methods relating to F1F0-ATPase inhibitors and targets thereof |
| AU5826100A (en) | 1999-07-13 | 2001-01-30 | F. Hoffmann-La Roche Ag | Benzazepinones and quinazolines |
| US6524623B1 (en) | 1999-11-12 | 2003-02-25 | Milton Hodosh | Therapeutic compositions and methods of use thereof |
| DE60117777T2 (de) | 2000-05-11 | 2006-08-17 | Eastman Chemical Co., Kingsport | Acylierte zyclodextrin guest-inklusion komplexe |
| US20020048566A1 (en) | 2000-09-14 | 2002-04-25 | El-Deiry Wafik S. | Modulation of cellular apoptosis and methods for treating cancer |
| CA2432825A1 (en) | 2000-12-15 | 2002-06-20 | Emory University | Nonpeptide agonists and antagonists of vasopressin receptors |
| CA2446696A1 (fr) | 2001-06-07 | 2002-12-12 | Neuro3D | Inhibiteurs des phosphodiesterases des nucleotides cycliques, preparation et utilisations de ces inhibiteurs |
| EP1423122A4 (en) | 2001-08-15 | 2008-12-10 | Univ Michigan | COMPOSITIONS AND METHODS RELATED TO NEW BENZODIAZEPINE COMPOUNDS AND THEIR OBJECTIVES |
| US6916813B2 (en) | 2001-12-10 | 2005-07-12 | Bristol-Myers Squibb Co. | (1-phenyl-2-heteoaryl)ethyl-guanidine compounds as inhibitors of mitochondrial F1F0 ATP hydrolase |
| US20040009972A1 (en) | 2002-06-17 | 2004-01-15 | Ding Charles Z. | Benzodiazepine inhibitors of mitochondial F1F0 ATP hydrolase and methods of inhibiting F1F0 ATP hydrolase |
| US7150433B2 (en) * | 2002-08-16 | 2006-12-19 | Toyota Motor Sales, U.S.A., Inc. | Aircraft bolster trays |
| US20040087489A1 (en) | 2002-11-06 | 2004-05-06 | Antonio Ruiz | Compositions and methods for the treatment of mycobacterial infections |
| US7745431B2 (en) * | 2002-12-03 | 2010-06-29 | Vela Acquisition Corporation | Pharmaceutical composition of 1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7-methoxy-8-hydroxy-5H-2,3-benzodiazepine and uses thereof |
| US7365070B2 (en) | 2002-12-04 | 2008-04-29 | Ore Pharmaceuticals Inc. | Modulators of melanocortin receptor |
| CA2524394C (en) | 2003-05-01 | 2011-07-12 | The Regents Of The University Of Michigan | Novel benzodiazepine compounds, compositions and uses 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 |
| US20090275099A1 (en) | 2004-04-27 | 2009-11-05 | Regents Of The University Of Michigan | Methods and compositions for treating diseases and conditions associated with mitochondrial function |
| WO2006007532A2 (en) | 2004-07-01 | 2006-01-19 | Synta Pharmaceuticals Corp. | 2-substituted heteroaryl compounds |
| 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 |
| WO2006053193A2 (en) | 2004-11-10 | 2006-05-18 | Garden Guardian, Inc. | A device and method for controlling animal behavior |
| JP2008528448A (ja) | 2005-01-03 | 2008-07-31 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 新規化合物に関連する組成物および方法、ならびにその標的 |
| JP2008545757A (ja) | 2005-06-01 | 2008-12-18 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 溶媒和されていないベンゾジアゼピン組成物および方法 |
| EP1742460A1 (en) | 2005-06-18 | 2007-01-10 | TTE Germany GmbH | Raster distortion correction circuit |
| US20070105844A1 (en) | 2005-10-26 | 2007-05-10 | Regents Of The University Of Michigan | Therapeutic compositions and methods |
| EP1951050A4 (en) | 2005-10-26 | 2011-04-27 | Univ Michigan | THERAPEUTIC COMPOSITIONS AND METHOD |
| EP1948191B1 (en) | 2005-11-01 | 2013-01-16 | The Regents of the University of Michigan | Novel 1,4-benzodiazepine-2,5-diones with therapeutic properties |
| US7759338B2 (en) | 2006-04-27 | 2010-07-20 | The Regents Of The University Of Michigan | Soluble 1,4 benzodiazepine compounds and stable salts thereof |
| EP2418206A3 (en) | 2006-06-09 | 2012-06-27 | The Regents of the University of Michigan | Benzodiazepine derivatives useful in the treatment of autoimmune disorders |
| GB0615068D0 (en) | 2006-07-28 | 2006-09-06 | Ttp Communications Ltd | Digital radio systems |
| KR101164718B1 (ko) * | 2007-03-09 | 2012-07-11 | 더 리젠츠 오브 더 유니버시티 오브 미시간 | 신규 화합물 및 이의 표적에 관한 조성물 및 방법 |
| MX2010002732A (es) | 2007-09-14 | 2010-06-02 | Univ Michigan | Inhibidores de f1f0-atpasa y metodos relacionados. |
| CN101918375A (zh) | 2007-11-06 | 2010-12-15 | 密歇根大学董事会 | 在皮肤病症的治疗中有用的苯并二氮杂*酮化合物 |
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- 2008-03-07 CA CA2680017A patent/CA2680017C/en not_active Expired - Fee Related
- 2008-03-07 CN CN200880012931A patent/CN101662940A/zh active Pending
- 2008-03-07 JP JP2009552910A patent/JP5383513B2/ja not_active Expired - Fee Related
- 2008-03-07 BR BRPI0808653-2A patent/BRPI0808653A2/pt not_active IP Right Cessation
- 2008-03-07 CA CA2783589A patent/CA2783589A1/en not_active Abandoned
- 2008-03-07 AU AU2008226532A patent/AU2008226532B2/en not_active Ceased
- 2008-03-07 NZ NZ579507A patent/NZ579507A/en not_active IP Right Cessation
-
2010
- 2010-12-07 US US12/962,225 patent/US8242109B2/en not_active Expired - Fee Related
-
2012
- 2012-07-10 US US13/545,546 patent/US20120289498A1/en not_active Abandoned
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