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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| US7572788B2 (en) * | 1999-04-30 | 2009-08-11 | The Regents Of The University Of Michigan | 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 |
| 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 |
| JP2005535710A (ja) * | 2002-08-09 | 2005-11-24 | トランス テック ファーマ，インコーポレイテッド | アリールおよびヘテロアリール化合物ならびに凝固を調節する方法 |
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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 |
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| US20070105844A1 (en) * | 2005-10-26 | 2007-05-10 | Regents Of The University Of Michigan | Therapeutic compositions and methods |
| AU2006308655B2 (en) | 2005-11-01 | 2010-09-23 | 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 |
| JP5264716B2 (ja) | 2006-06-09 | 2013-08-14 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | 化合物およびその標的に関連する組成物および方法 |
| AU2008226532B2 (en) | 2007-03-09 | 2011-09-22 | The Regents Of The University Of Michigan | Compositions and methods relating to novel compounds and targets thereof |
| EP2146722A4 (en) * | 2007-05-10 | 2011-08-03 | Amr Technology Inc | ARYL AND HETEROARYL SUBSTITUTED TETRAHYDROBENZO-1,4-DIAZEPINES AND THEIR USE FOR BLOCKING THE RECOVERY OF NOREPINEPHRIN, DOPAMINE AND SEROTONINE |
| ES2614498T3 (es) * | 2007-09-14 | 2017-05-31 | The Regents Of The University Of Michigan | Inhibidores de ATPasa F1F0 y métodos relacionados |
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| WO2010030891A2 (en) | 2008-09-11 | 2010-03-18 | The Regents Of The University Of Michigan | Aryl guanidine f1f0-atpase inhibitors and related methods |
| US8604023B2 (en) | 2009-04-17 | 2013-12-10 | The Regents Of The University Of Michigan | 1,4-benzodiazepinone compounds and their use in treating cancer |
| JP2013505258A (ja) | 2009-09-18 | 2013-02-14 | ザ リージェンツ オブ ザ ユニバーシティ オブ ミシガン | ベンゾジアゼピノン化合物およびそれを使用する治療方法 |
| 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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| IL93401A (en) * | 1989-03-08 | 1994-08-26 | Kali Chemie Pharma Gmbh | H1 - Indole - 2 - Carboxylic acid 1, 7 - Consolidated N -) 1, 4 - Benzodiazepine - 3 - Il (amides, their preparation and drugs containing them |
| TW221687B (enExample) * | 1992-01-24 | 1994-03-11 | Hoffmann La Roche | |
| DE19604920A1 (de) | 1996-02-01 | 1997-08-07 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
| US5891871A (en) * | 1996-03-21 | 1999-04-06 | Cocensys, Inc. | Substituted 2,3-benzodiazepin-4-ones and the use thereof |
| WO2000079263A2 (en) * | 1999-06-18 | 2000-12-28 | Synt:Em S.A. | Identifying active molecules using physico-chemical parameters |
| WO2002051232A2 (en) | 2000-12-27 | 2002-07-04 | Actelion Pharmaceuticals Ltd. | Novel benzazepines and related heterocyclic derivatives |
-
2002
- 2002-06-07 AU AU2002317910A patent/AU2002317910B2/en not_active Ceased
- 2002-06-07 WO PCT/FR2002/001952 patent/WO2002098865A2/fr not_active Ceased
- 2002-06-07 US US10/479,000 patent/US7250410B2/en not_active Expired - Fee Related
- 2002-06-07 EP EP02747514A patent/EP1392663A2/fr not_active Withdrawn
- 2002-06-07 IL IL15910502A patent/IL159105A0/xx unknown
- 2002-06-07 CA CA002446696A patent/CA2446696A1/fr not_active Abandoned
- 2002-06-07 NZ NZ529582A patent/NZ529582A/en unknown
- 2002-06-07 JP JP2003501989A patent/JP2005503356A/ja active Pending
-
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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