JP2005503356A5 - - Google Patents
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- Publication number
- JP2005503356A5 JP2005503356A5 JP2003501989A JP2003501989A JP2005503356A5 JP 2005503356 A5 JP2005503356 A5 JP 2005503356A5 JP 2003501989 A JP2003501989 A JP 2003501989A JP 2003501989 A JP2003501989 A JP 2003501989A JP 2005503356 A5 JP2005503356 A5 JP 2005503356A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- benzodiazepin
- dimethoxy
- phenyl
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 43
- 125000003118 aryl group Chemical group 0.000 claims 27
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims 8
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000001350 alkyl halides Chemical class 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000001424 substituent 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 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 230000003213 activating effect Effects 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- ASCRLTIXZKFQJI-UHFFFAOYSA-N 1-(1-benzothiophen-2-yl)-7,8-diethoxy-3-ethyl-5h-2,3-benzodiazepin-4-one Chemical compound C1=2C=C(OCC)C(OCC)=CC=2CC(=O)N(CC)N=C1C1=CC2=CC=CC=C2S1 ASCRLTIXZKFQJI-UHFFFAOYSA-N 0.000 claims 1
- SJABLWFWDKABFZ-UHFFFAOYSA-N 1-(1-benzothiophen-2-yl)-7,8-diethoxy-5-propyl-3,5-dihydro-2,3-benzodiazepin-4-one Chemical compound N1C(=O)C(CCC)C2=CC(OCC)=C(OCC)C=C2C(C=2SC3=CC=CC=C3C=2)=N1 SJABLWFWDKABFZ-UHFFFAOYSA-N 0.000 claims 1
- OWTKSBICDHTGEY-UHFFFAOYSA-N 1-[4-[3,5-bis(trifluoromethyl)phenyl]phenyl]-7,8-dimethoxy-3-methyl-5h-2,3-benzodiazepin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(=O)N(C)N=C1C(C=C1)=CC=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 OWTKSBICDHTGEY-UHFFFAOYSA-N 0.000 claims 1
- IQWQEVCQXDEINJ-UHFFFAOYSA-N 1-ethyl-3-[hydroxy(diphenyl)methyl]-7,8-dimethoxy-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(CC)C2=CC(OC)=C(OC)C=C2C(C=2C=CC=CC=2)=NC1C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 IQWQEVCQXDEINJ-UHFFFAOYSA-N 0.000 claims 1
- HCIKDGRDIWWCHS-UHFFFAOYSA-N 1-ethyl-7,8-dimethoxy-3-[(2-methoxyphenyl)methyl]-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(CC)C2=CC(OC)=C(OC)C=C2C(C=2C=CC=CC=2)=NC1CC1=CC=CC=C1OC HCIKDGRDIWWCHS-UHFFFAOYSA-N 0.000 claims 1
- WNWRPVFIEUZBNY-UHFFFAOYSA-N 1-ethyl-7,8-dimethoxy-5-[4-(3-phenylmethoxyprop-1-ynyl)phenyl]-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CC)C2=CC(OC)=C(OC)C=C2C=1C(C=C1)=CC=C1C#CCOCC1=CC=CC=C1 WNWRPVFIEUZBNY-UHFFFAOYSA-N 0.000 claims 1
- PKLOQQDQBJEJQS-UHFFFAOYSA-N 1-ethyl-7,8-dimethoxy-5-phenyl-3-[(3-phenylphenyl)methyl]-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(CC)C2=CC(OC)=C(OC)C=C2C(C=2C=CC=CC=2)=NC1CC(C=1)=CC=CC=1C1=CC=CC=C1 PKLOQQDQBJEJQS-UHFFFAOYSA-N 0.000 claims 1
- DNVLRCDPCFXSAQ-UHFFFAOYSA-N 1-ethyl-7,8-dimethoxy-5-phenyl-3-[(4-phenylphenyl)methyl]-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(CC)C2=CC(OC)=C(OC)C=C2C(C=2C=CC=CC=2)=NC1CC(C=C1)=CC=C1C1=CC=CC=C1 DNVLRCDPCFXSAQ-UHFFFAOYSA-N 0.000 claims 1
- WQQPGMSAJNSWML-UHFFFAOYSA-N 1-ethyl-7,8-dimethoxy-5-phenyl-3-prop-2-ynyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1C(CC#C)C(=O)N(CC)C2=CC(OC)=C(OC)C=C2C=1C1=CC=CC=C1 WQQPGMSAJNSWML-UHFFFAOYSA-N 0.000 claims 1
- MAGIXZPMCBHOFV-UHFFFAOYSA-N 2-(1-ethyl-7,8-dimethoxy-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl)acetamide Chemical compound N=1C(CC(N)=O)C(=O)N(CC)C2=CC(OC)=C(OC)C=C2C=1C1=CC=CC=C1 MAGIXZPMCBHOFV-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- ZEKZWMAZSZKUMS-UHFFFAOYSA-N 3-(1-benzyl-4-hydroxypiperidin-4-yl)-1-ethyl-7,8-dimethoxy-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(CC)C2=CC(OC)=C(OC)C=C2C(C=2C=CC=CC=2)=NC1C(CC1)(O)CCN1CC1=CC=CC=C1 ZEKZWMAZSZKUMS-UHFFFAOYSA-N 0.000 claims 1
- XMVVYXKYZQBPRB-UHFFFAOYSA-N 3-[(1-ethyl-7,8-dimethoxy-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl)methyl]benzamide Chemical compound O=C1N(CC)C2=CC(OC)=C(OC)C=C2C(C=2C=CC=CC=2)=NC1CC1=CC=CC(C(N)=O)=C1 XMVVYXKYZQBPRB-UHFFFAOYSA-N 0.000 claims 1
- MBUSWDJSEGOHES-UHFFFAOYSA-N 3-[(8-ethoxy-7-methoxy-1-methyl-2-oxo-5-phenyl-3h-1,4-benzodiazepin-3-yl)methyl]benzamide Chemical compound N1=C(C=2C=CC=CC=2)C=2C=C(OC)C(OCC)=CC=2N(C)C(=O)C1CC1=CC=CC(C(N)=O)=C1 MBUSWDJSEGOHES-UHFFFAOYSA-N 0.000 claims 1
- FGMBQTNFQLFNRR-UHFFFAOYSA-N 3-[1,2-bis(4-bromophenyl)ethyl]-1-ethyl-7,8-dimethoxy-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound O=C1N(CC)C2=CC(OC)=C(OC)C=C2C(C=2C=CC=CC=2)=NC1C(C=1C=CC(Br)=CC=1)CC1=CC=C(Br)C=C1 FGMBQTNFQLFNRR-UHFFFAOYSA-N 0.000 claims 1
- LWODOYULCBDJNI-UHFFFAOYSA-N 3-[[2-(aminomethyl)phenyl]methyl]-1-ethyl-7,8-dimethoxy-5-phenyl-3H-1,4-benzodiazepin-2-one N-[[2-(7,8-dimethoxy-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl)phenyl]methyl]acetamide Chemical compound O=C1N(CC)C2=CC(OC)=C(OC)C=C2C(C=2C=CC=CC=2)=NC1CC1=CC=CC=C1CN.C1=2C=C(OC)C(OC)=CC=2NC(=O)C(C=2C(=CC=CC=2)CNC(C)=O)N=C1C1=CC=CC=C1 LWODOYULCBDJNI-UHFFFAOYSA-N 0.000 claims 1
- RGEJQYAPVPRMKI-UHFFFAOYSA-N 3-benzyl-8-ethoxy-1-ethyl-7-methoxy-5-phenyl-3h-1,4-benzodiazepin-2-one;8-ethoxy-1-ethyl-7-methoxy-3,5-diphenyl-3h-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(OC)C(OCC)=CC=2N(CC)C(=O)C(C=2C=CC=CC=2)N=C1C1=CC=CC=C1.N1=C(C=2C=CC=CC=2)C=2C=C(OC)C(OCC)=CC=2N(CC)C(=O)C1CC1=CC=CC=C1 RGEJQYAPVPRMKI-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- IXVZTSJPZJXQPY-UHFFFAOYSA-N 5-(1h-indol-5-yl)-7,8-dimethoxy-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2N(C)C(=O)CN=C1C1=CC=C(NC=C2)C2=C1 IXVZTSJPZJXQPY-UHFFFAOYSA-N 0.000 claims 1
- ZOKLVYBIKSORDC-UHFFFAOYSA-N 5-(2-bromophenyl)-7,8-dimethoxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)CN=C1C1=CC=CC=C1Br ZOKLVYBIKSORDC-UHFFFAOYSA-N 0.000 claims 1
- OUPKYSJIOYLADC-UHFFFAOYSA-N 5-(3-bromophenyl)-7,8-dimethoxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)CN=C1C1=CC=CC(Br)=C1 OUPKYSJIOYLADC-UHFFFAOYSA-N 0.000 claims 1
- YFGFRHZXXKDTFA-UHFFFAOYSA-N 5-(3-chlorophenyl)-7,8-dimethoxy-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2N(C)C(=O)CN=C1C1=CC=CC(Cl)=C1 YFGFRHZXXKDTFA-UHFFFAOYSA-N 0.000 claims 1
- AALFNMGUYPJUST-UHFFFAOYSA-N 5-[3,5-bis(trifluoromethyl)phenyl]-7,8-dimethoxy-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2N(C)C(=O)CN=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AALFNMGUYPJUST-UHFFFAOYSA-N 0.000 claims 1
- JEFSPAVNHMTXPS-UHFFFAOYSA-N 7,8-dimethoxy-1-[4-(4-methoxyphenyl)phenyl]-3-methyl-5h-2,3-benzodiazepin-4-one Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2C3=CC(OC)=C(OC)C=C3CC(=O)N(C)N=2)C=C1 JEFSPAVNHMTXPS-UHFFFAOYSA-N 0.000 claims 1
- CIBFDTUUNLMFMC-UHFFFAOYSA-N 7,8-dimethoxy-1-phenyl-3,5-dihydro-2,3-benzodiazepin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(=O)NN=C1C1=CC=CC=C1 CIBFDTUUNLMFMC-UHFFFAOYSA-N 0.000 claims 1
- XLAQCBYTYMNGDR-UHFFFAOYSA-N 7,8-dimethoxy-1-phenyl-3-propyl-5h-2,3-benzodiazepin-4-one Chemical compound C12=CC(OC)=C(OC)C=C2CC(=O)N(CCC)N=C1C1=CC=CC=C1 XLAQCBYTYMNGDR-UHFFFAOYSA-N 0.000 claims 1
- NSFKQWZKLQUICF-UHFFFAOYSA-N 7,8-dimethoxy-3-(2-methylsulfanylethyl)-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one;3-(1h-indol-3-ylmethyl)-7,8-dimethoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)C(CCSC)N=C1C1=CC=CC=C1.C1=2C=C(OC)C(OC)=CC=2NC(=O)C(CC=2C3=CC=CC=C3NC=2)N=C1C1=CC=CC=C1 NSFKQWZKLQUICF-UHFFFAOYSA-N 0.000 claims 1
- CBZDWXSMWJWFGA-UHFFFAOYSA-N 7,8-dimethoxy-3-methyl-1-(4-thiophen-2-ylphenyl)-5h-2,3-benzodiazepin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(=O)N(C)N=C1C(C=C1)=CC=C1C1=CC=CS1 CBZDWXSMWJWFGA-UHFFFAOYSA-N 0.000 claims 1
- UJSOHZFFVQFFQG-UHFFFAOYSA-N 7,8-dimethoxy-3-methyl-1-[4-(3-nitrophenyl)phenyl]-5h-2,3-benzodiazepin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(=O)N(C)N=C1C(C=C1)=CC=C1C1=CC=CC([N+]([O-])=O)=C1 UJSOHZFFVQFFQG-UHFFFAOYSA-N 0.000 claims 1
- ACXGWEHMIUPNGX-UHFFFAOYSA-N 7,8-dimethoxy-3-methyl-1-[4-[3-(trifluoromethyl)phenyl]phenyl]-5h-2,3-benzodiazepin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CC(=O)N(C)N=C1C(C=C1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 ACXGWEHMIUPNGX-UHFFFAOYSA-N 0.000 claims 1
- FVCLLYSNQRDQGL-UHFFFAOYSA-N 7,8-dimethoxy-3-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(=O)C(C)N=C1C1=CC=CC=C1 FVCLLYSNQRDQGL-UHFFFAOYSA-N 0.000 claims 1
- ICYHWTLVAMZICW-UHFFFAOYSA-N 8-bromo-5-(4-bromophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one 7-iodo-5-[3-(trifluoromethyl)phenyl]-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound IC=1C=CC2=C(C(=NCC(N2)=O)C2=CC(=CC=C2)C(F)(F)F)C1.BrC1=CC2=C(C(=NCC(N2)=O)C2=CC=C(C=C2)Br)C=C1 ICYHWTLVAMZICW-UHFFFAOYSA-N 0.000 claims 1
- GVWCSZJBGUTVJA-UHFFFAOYSA-N 8-methoxy-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound C=1C(OC)=CC=C2C=1N(C)C(=O)CN=C2C1=CC=CC=C1 GVWCSZJBGUTVJA-UHFFFAOYSA-N 0.000 claims 1
- WHPSIXNYRRDLLR-UHFFFAOYSA-N BrC1=CC=C(C=C1)C1=NCC(NC2=C1C=C(C(=C2)OC)OC)=O.BrC2=CC=C(C=C2)C2=NCC(N(C1=C2C=C(C(=C1)OC)OC)C)=O Chemical compound BrC1=CC=C(C=C1)C1=NCC(NC2=C1C=C(C(=C2)OC)OC)=O.BrC2=CC=C(C=C2)C2=NCC(N(C1=C2C=C(C(=C1)OC)OC)C)=O WHPSIXNYRRDLLR-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- XWIOUMQHEOMYLF-UHFFFAOYSA-N C(C)N1C(C(N=C(C2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2)CC2=CC(=CC=C2)C(F)(F)F)=O.C(C)OC2=CC1=C(C(=NCC(N1C)=O)C1=CC=CC=C1)C=C2OC Chemical compound C(C)N1C(C(N=C(C2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2)CC2=CC(=CC=C2)C(F)(F)F)=O.C(C)OC2=CC1=C(C(=NCC(N1C)=O)C1=CC=CC=C1)C=C2OC XWIOUMQHEOMYLF-UHFFFAOYSA-N 0.000 claims 1
- XMOWNHARCXKXBD-UHFFFAOYSA-N C(C)N1N=C(C2=C(CC1=O)C=C(C(=C2)OC)OC)C2=CC=CC=C2.COC=2C(=CC1=C(CC(N(N=C1C1=CC=CC=C1)CCCCCCCCCCCC(=O)OC)=O)C2)OC Chemical compound C(C)N1N=C(C2=C(CC1=O)C=C(C(=C2)OC)OC)C2=CC=CC=C2.COC=2C(=CC1=C(CC(N(N=C1C1=CC=CC=C1)CCCCCCCCCCCC(=O)OC)=O)C2)OC XMOWNHARCXKXBD-UHFFFAOYSA-N 0.000 claims 1
- CACJYBKRXKLING-UHFFFAOYSA-N C(C)OC1=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C=C1OC.C(C)N1C(C(N=C(C2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2)CC2=C(C=CC=C2)C)=O Chemical compound C(C)OC1=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C=C1OC.C(C)N1C(C(N=C(C2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2)CC2=C(C=CC=C2)C)=O CACJYBKRXKLING-UHFFFAOYSA-N 0.000 claims 1
- MSXQQBHAMHZOSF-UHFFFAOYSA-N C(C)OC=1C(=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1)OCC.C(C1=CC=CC=C1)N1C(CN=C(C2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2)=O Chemical compound C(C)OC=1C(=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1)OCC.C(C1=CC=CC=C1)N1C(CN=C(C2=C1C=C(C(=C2)OC)OC)C2=CC=CC=C2)=O MSXQQBHAMHZOSF-UHFFFAOYSA-N 0.000 claims 1
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- RGZATWPGZGJBNA-UHFFFAOYSA-N C(C1=CC=CC=C1)C1C(NC2=C(C(=N1)C1=CC=CC=C1)C=C(C(=C2)OC)OC)=O.COC=2C(=CC1=C(C(=NC(C(N1)=O)CC(C)C)C1=CC=CC=C1)C2)OC Chemical compound C(C1=CC=CC=C1)C1C(NC2=C(C(=N1)C1=CC=CC=C1)C=C(C(=C2)OC)OC)=O.COC=2C(=CC1=C(C(=NC(C(N1)=O)CC(C)C)C1=CC=CC=C1)C2)OC RGZATWPGZGJBNA-UHFFFAOYSA-N 0.000 claims 1
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| US7144880B2 (en) * | 1999-04-30 | 2006-12-05 | Regents Of The University Of Michigan | Compositions 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 |
| PL374971A1 (en) | 2002-08-09 | 2005-11-14 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
| CA2503716A1 (fr) * | 2002-10-30 | 2004-05-21 | Jean-Jacques Bourguignon | Utilisation d'inhibiteurs des phosphodiesterases des nucleotides cycliques, ayant une structure benzodiazepinique en therapie |
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| 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 |
| 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 |
| FR2870539B1 (fr) * | 2004-05-19 | 2006-08-04 | Greenpharma Sa Sa | Nouvelles methodes et medicaments |
| US7572783B2 (en) | 2004-08-13 | 2009-08-11 | Amgen Inc. | Substituted benzofused heterocycles |
| 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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| US20070105844A1 (en) * | 2005-10-26 | 2007-05-10 | Regents Of The University Of Michigan | Therapeutic compositions and methods |
| NZ568254A (en) * | 2005-11-01 | 2011-06-30 | Univ Michigan | 1,4-Benzodiazepine-2,5-diones for regulating cell death and treating autoimmune diseases |
| 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 |
| MX2009009645A (es) | 2007-03-09 | 2009-11-19 | Univ Michigan | Composiciones y metodos relacionados con nuevos compuestos y objetivos de los mismos. |
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| EP2200977B1 (en) * | 2007-09-14 | 2016-11-09 | The Regents of the University of Michigan | F1f0-atpase inhibitors and related methods |
| WO2009037302A1 (en) * | 2007-09-18 | 2009-03-26 | Via Pharmaceuticals, Inc. | 5-substituted-1, 4-benz0diazepines as phosphodiesterase inhibitors |
| WO2009061916A2 (en) | 2007-11-06 | 2009-05-14 | The Regents Of The University Of Michigan | Benzodiazepinone compounds useful in the treatment of skin conditions |
| AU2009291632B2 (en) | 2008-09-11 | 2013-04-04 | 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 |
| EP2470020A4 (en) | 2009-09-18 | 2013-03-13 | Univ Michigan | BENZODIAZEPINONE COMPOUNDS AND TREATMENT METHODS THEREWITH |
| AU2010322287B2 (en) | 2009-11-17 | 2014-04-03 | The Regents Of The University Of Michigan | 1,4-benzodiazepine-2,5-diones and related compounds with therapeutic properties |
| US9126978B2 (en) | 2009-11-17 | 2015-09-08 | The Regents Of The University Of Michigan | 1,4-benzodiazepine-2,5-diones and related compounds with therapeutic properties |
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| US9624244B2 (en) | 2012-06-06 | 2017-04-18 | Constellation Pharmaceuticals, Inc. | Benzo [B] isoxazoloazepine bromodomain inhibitors and uses thereof |
| TWI602820B (zh) | 2012-06-06 | 2017-10-21 | 星宿藥物公司 | 溴域抑制劑及其用途 |
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| WO2023220395A1 (en) * | 2022-05-13 | 2023-11-16 | University Of Cincinnati | Benzodiazepine analogs and methods of use in treating cancer |
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-
2002
- 2002-06-07 IL IL15910502A patent/IL159105A0/xx unknown
- 2002-06-07 JP JP2003501989A patent/JP2005503356A/ja active Pending
- 2002-06-07 US US10/479,000 patent/US7250410B2/en not_active Expired - Fee Related
- 2002-06-07 WO PCT/FR2002/001952 patent/WO2002098865A2/fr not_active Ceased
- 2002-06-07 AU AU2002317910A patent/AU2002317910B2/en not_active Ceased
- 2002-06-07 EP EP02747514A patent/EP1392663A2/fr not_active Withdrawn
- 2002-06-07 NZ NZ529582A patent/NZ529582A/en unknown
- 2002-06-07 CA CA002446696A patent/CA2446696A1/fr not_active Abandoned
-
2003
- 2003-11-27 IL IL159105A patent/IL159105A/en not_active IP Right Cessation
-
2004
- 2004-01-06 ZA ZA200400057A patent/ZA200400057B/en unknown
-
2008
- 2008-09-18 AU AU2008221554A patent/AU2008221554A1/en not_active Abandoned
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