CA2831291A1 - Methods of targeted treatment of frontotemporal lobar degeneration - Google Patents

Info

Publication number

CA2831291A1

CA2831291A1 CA2831291A CA2831291A CA2831291A1 CA 2831291 A1 CA2831291 A1 CA 2831291A1 CA 2831291 A CA2831291 A CA 2831291A CA 2831291 A CA2831291 A CA 2831291A CA 2831291 A1 CA2831291 A1 CA 2831291A1

Authority

CA

Canada

Prior art keywords

c6alkyl

oxazepin

c4alkyl

group

dibenzo

Prior art date

2011-03-26

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 201000011240 Frontotemporal dementia Diseases 0.000 title claims abstract description 235
• 208000002339 Frontotemporal Lobar Degeneration Diseases 0.000 title claims abstract description 194
• 238000000034 method Methods 0.000 title claims description 88
• 238000003556 assay Methods 0.000 claims abstract description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 195
• 125000003118 aryl group Chemical group 0.000 claims description 183
• -1 -OH Chemical group 0.000 claims description 166
• 125000001424 substituent group Chemical group 0.000 claims description 161
• 125000000217 alkyl group Chemical group 0.000 claims description 144
• 125000001072 heteroaryl group Chemical group 0.000 claims description 139
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 132
• 125000005843 halogen group Chemical group 0.000 claims description 130
• 150000001875 compounds Chemical class 0.000 claims description 126
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 122
• 239000003795 chemical substances by application Substances 0.000 claims description 111
• 108010012809 Progranulins Proteins 0.000 claims description 88
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 88
• 102000019204 Progranulins Human genes 0.000 claims description 75
• 229910052739 hydrogen Inorganic materials 0.000 claims description 69
• 239000000203 mixture Substances 0.000 claims description 60
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 55
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 49
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 45
• 108700028369 Alleles Proteins 0.000 claims description 26
• 229910052731 fluorine Inorganic materials 0.000 claims description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 241000282414 Homo sapiens Species 0.000 claims description 18
• 108020004999 messenger RNA Proteins 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 241000124008 Mammalia Species 0.000 claims description 11
• 125000005605 benzo group Chemical group 0.000 claims description 7
• YKTHWCKOZFNHLO-UHFFFAOYSA-N n-hydroxy-4-[11-(2-morpholin-4-ylethyl)benzo[b][1,4]benzodiazepin-6-yl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C(C1=CC=CC=C11)=NC2=CC=CC=C2N1CCN1CCOCC1 YKTHWCKOZFNHLO-UHFFFAOYSA-N 0.000 claims description 6
• IQFRWAOSBZHQMX-UHFFFAOYSA-N 4-[(benzo[b][1,4]benzoxazepin-6-ylamino)methyl]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC1=NC2=CC=CC=C2OC2=CC=CC=C12 IQFRWAOSBZHQMX-UHFFFAOYSA-N 0.000 claims description 4
• HDAIRFRHDIODJQ-UHFFFAOYSA-N 6-[(4-benzo[b][1,4]benzoxazepin-6-ylphenyl)methylamino]-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound C1=CC=CC2=C1C(=N/C1=C(O2)C=CC=C1)C1=CC=C(CNC2C(C(C(C(O2)C(=O)O)O)O)O)C=C1 HDAIRFRHDIODJQ-UHFFFAOYSA-N 0.000 claims description 4
• FCCKQFSCBCAXDN-UHFFFAOYSA-N n-hydroxy-4-(10-propylbenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound CCCC1=CC=CC2=C1OC1=CC=CC=C1N=C2C1=CC=C(C(=O)NO)C=C1 FCCKQFSCBCAXDN-UHFFFAOYSA-N 0.000 claims description 4
• WFQIYDSBYXEJKZ-UHFFFAOYSA-N 4-[2-(benzo[b][1,4]benzoxazepin-6-ylamino)ethyl]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1CCNC1=NC2=CC=CC=C2OC2=CC=CC=C12 WFQIYDSBYXEJKZ-UHFFFAOYSA-N 0.000 claims description 3
• DOHBBYALVPXETD-UHFFFAOYSA-N C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=C[N+]([O-])=CC=C12 Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=C[N+]([O-])=CC=C12 DOHBBYALVPXETD-UHFFFAOYSA-N 0.000 claims description 3
• 230000007850 degeneration Effects 0.000 claims description 3
• DZTZYVCWUBRWLH-UHFFFAOYSA-N n-hydroxy-4-(10-methylsulfinylbenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound CS(=O)C1=CC=CC2=C1OC1=CC=CC=C1N=C2C1=CC=C(C(=O)NO)C=C1 DZTZYVCWUBRWLH-UHFFFAOYSA-N 0.000 claims description 3
• CWQXFCIGZUJTMH-UHFFFAOYSA-N n-hydroxy-4-[10-(2-methoxyethoxy)benzo[b][1,4]benzoxazepin-6-yl]benzamide Chemical compound COCCOC1=CC=CC2=C1OC1=CC=CC=C1N=C2C1=CC=C(C(=O)NO)C=C1 CWQXFCIGZUJTMH-UHFFFAOYSA-N 0.000 claims description 3
• RMNQZPRKBLZWFQ-UHFFFAOYSA-N n-hydroxy-4-[10-(trifluoromethoxy)benzo[b][1,4]benzoxazepin-6-yl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=C(OC(F)(F)F)C=CC=C12 RMNQZPRKBLZWFQ-UHFFFAOYSA-N 0.000 claims description 3
• ZGKYIKURSJMNJC-UHFFFAOYSA-N n-hydroxy-4-[10-methoxy-3-(trifluoromethyl)benzo[b][1,4]benzoxazepin-6-yl]benzamide Chemical compound COC1=CC=CC2=C1OC1=CC=C(C(F)(F)F)C=C1N=C2C1=CC=C(C(=O)NO)C=C1 ZGKYIKURSJMNJC-UHFFFAOYSA-N 0.000 claims description 3
• KTSOHMXHVGZAPO-UHFFFAOYSA-N pyrido[4,3-f][1,4]oxazepine Chemical compound O1C=CN=CC2=CC=NC=C12 KTSOHMXHVGZAPO-UHFFFAOYSA-N 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 22
• ZBYQBWHQMGPCBT-UHFFFAOYSA-N 4-benzo[b][1,4]benzoxazepin-6-yl-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC=CC=C12 ZBYQBWHQMGPCBT-UHFFFAOYSA-N 0.000 claims 3
• HGWLTRRNKHOLIR-UHFFFAOYSA-N 3-benzo[b][1,4]benzoxazepin-6-yl-n-hydroxybenzamide Chemical compound ONC(=O)C1=CC=CC(C=2C3=CC=CC=C3OC3=CC=CC=C3N=2)=C1 HGWLTRRNKHOLIR-UHFFFAOYSA-N 0.000 claims 2
• SWYHUULPITWRBP-UHFFFAOYSA-N 4-(11-cyclopropyl-8-fluorobenzo[b][1,4]benzodiazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C(C1=CC(F)=CC=C11)=NC2=CC=CC=C2N1C1CC1 SWYHUULPITWRBP-UHFFFAOYSA-N 0.000 claims 2
• PFSXJBFAWJVMPP-UHFFFAOYSA-N 4-(11-cyclopropylbenzo[b][1,4]benzodiazepin-6-yl)-n-hydroxy-n-methylbenzamide Chemical compound C1=CC(C(=O)N(O)C)=CC=C1C(C1=CC=CC=C11)=NC2=CC=CC=C2N1C1CC1 PFSXJBFAWJVMPP-UHFFFAOYSA-N 0.000 claims 2
• MIJGONCMCAHGNX-UHFFFAOYSA-N 4-(11-cyclopropylbenzo[b][1,4]benzodiazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C(C1=CC=CC=C11)=NC2=CC=CC=C2N1C1CC1 MIJGONCMCAHGNX-UHFFFAOYSA-N 0.000 claims 2
• SKDLHAAUIUFOBJ-UHFFFAOYSA-N 4-(11-cyclopropylpyrido[2,3-b][1,5]benzodiazepin-5-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C(C1=CC=CN=C11)=NC2=CC=CC=C2N1C1CC1 SKDLHAAUIUFOBJ-UHFFFAOYSA-N 0.000 claims 2
• QTGGHMCAFOOZEY-UHFFFAOYSA-N 4-(11-ethylbenzo[b][1,4]benzodiazepin-6-yl)-n-hydroxybenzamide Chemical compound C12=CC=CC=C2N(CC)C2=CC=CC=C2N=C1C1=CC=C(C(=O)NO)C=C1 QTGGHMCAFOOZEY-UHFFFAOYSA-N 0.000 claims 2
• SYXIDWBYJFWNJQ-UHFFFAOYSA-N 4-(11-ethylpyrido[2,3-b][1,5]benzodiazepin-5-yl)-n-hydroxybenzamide Chemical compound C12=CC=CN=C2N(CC)C2=CC=CC=C2N=C1C1=CC=C(C(=O)NO)C=C1 SYXIDWBYJFWNJQ-UHFFFAOYSA-N 0.000 claims 2
• BLMRWAZWBZJUFF-UHFFFAOYSA-N 4-(11h-benzo[b][1,4]benzodiazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2NC2=CC=CC=C12 BLMRWAZWBZJUFF-UHFFFAOYSA-N 0.000 claims 2
• KEQFLEXTPWTOSM-UHFFFAOYSA-N 4-(2-chlorobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=C(Cl)C=C2OC2=CC=CC=C12 KEQFLEXTPWTOSM-UHFFFAOYSA-N 0.000 claims 2
• OYBSXVBWVJKHRO-UHFFFAOYSA-N 4-(2-cyanobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=C(C#N)C=C2OC2=CC=CC=C12 OYBSXVBWVJKHRO-UHFFFAOYSA-N 0.000 claims 2
• QIPJDHBKKRZLEH-UHFFFAOYSA-N 4-(3-chloro-11H-benzo[b][1,4]benzodiazepin-6-yl)-N-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QIPJDHBKKRZLEH-UHFFFAOYSA-N 0.000 claims 2
• UAMADBXBRQBAJP-UHFFFAOYSA-N 4-(3-chlorobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC(Cl)=CC=C2OC2=CC=CC=C12 UAMADBXBRQBAJP-UHFFFAOYSA-N 0.000 claims 2
• IWPAECNIHGOBIJ-UHFFFAOYSA-N 4-(3-cyanobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC(C#N)=CC=C2OC2=CC=CC=C12 IWPAECNIHGOBIJ-UHFFFAOYSA-N 0.000 claims 2
• MKWSFGXGPHIVEI-UHFFFAOYSA-N 4-(5,6-dihydrobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1C2=CC=CC=C2OC2=CC=CC=C2N1 MKWSFGXGPHIVEI-UHFFFAOYSA-N 0.000 claims 2
• QPOGQJIAADBFRX-UHFFFAOYSA-N 4-(8-chlorobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 QPOGQJIAADBFRX-UHFFFAOYSA-N 0.000 claims 2
• IOXRZAIVECUMTQ-UHFFFAOYSA-N 4-(8-fluoro-10-methoxybenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound COC1=CC(F)=CC2=C1OC1=CC=CC=C1N=C2C1=CC=C(C(=O)NO)C=C1 IOXRZAIVECUMTQ-UHFFFAOYSA-N 0.000 claims 2
• QXHOEGCVMCOBBD-UHFFFAOYSA-N 4-[11-(cyclopropylmethyl)pyrido[2,3-b][1,5]benzodiazepin-5-yl]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C(C1=CC=CN=C11)=NC2=CC=CC=C2N1CC1CC1 QXHOEGCVMCOBBD-UHFFFAOYSA-N 0.000 claims 2
• PBPPCJHSWQCENE-UHFFFAOYSA-N 4-[8-[2-(dimethylamino)ethoxy]benzo[b][1,4]benzoxazepin-6-yl]-n-hydroxybenzamide Chemical compound C12=CC(OCCN(C)C)=CC=C2OC2=CC=CC=C2N=C1C1=CC=C(C(=O)NO)C=C1 PBPPCJHSWQCENE-UHFFFAOYSA-N 0.000 claims 2
• LDLGMAPVRIJPPK-UHFFFAOYSA-N 4-benzo[b][1,4]benzoxazepin-6-yl-2-fluoro-n-hydroxybenzamide Chemical compound C1=C(F)C(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC=CC=C12 LDLGMAPVRIJPPK-UHFFFAOYSA-N 0.000 claims 2
• BFMWIFSWFYYOBS-UHFFFAOYSA-N 4-benzo[b][1,4]benzoxazepin-6-yl-3-fluoro-n-hydroxybenzamide Chemical compound FC1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC=CC=C12 BFMWIFSWFYYOBS-UHFFFAOYSA-N 0.000 claims 2
• AGXPTJMNQUOECM-UHFFFAOYSA-N 5-benzo[b][1,4]benzoxazepin-6-yl-n-hydroxyfuran-2-carboxamide Chemical compound O1C(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC=CC=C12 AGXPTJMNQUOECM-UHFFFAOYSA-N 0.000 claims 2
• GUHHQIRHFGBOTL-UHFFFAOYSA-N 5-benzo[b][1,4]benzoxazepin-6-yl-n-hydroxythiophene-2-carboxamide Chemical compound S1C(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC=CC=C12 GUHHQIRHFGBOTL-UHFFFAOYSA-N 0.000 claims 2
• MBMRQBSDQYTHIV-UHFFFAOYSA-N n-hydroxy-4-(11-propan-2-ylbenzo[b][1,4]benzodiazepin-6-yl)benzamide Chemical compound C12=CC=CC=C2N(C(C)C)C2=CC=CC=C2N=C1C1=CC=C(C(=O)NO)C=C1 MBMRQBSDQYTHIV-UHFFFAOYSA-N 0.000 claims 2
• VIEPUKVMHKOTOU-UHFFFAOYSA-N n-hydroxy-4-(11-propan-2-ylpyrido[2,3-b][1,5]benzodiazepin-5-yl)benzamide Chemical compound C12=CC=CN=C2N(C(C)C)C2=CC=CC=C2N=C1C1=CC=C(C(=O)NO)C=C1 VIEPUKVMHKOTOU-UHFFFAOYSA-N 0.000 claims 2
• GSHJNEGTRIPBPA-UHFFFAOYSA-N n-hydroxy-4-(11h-pyrrolo[2,1-c][1,4]benzodiazepin-6-yl)benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2CN2C1=CC=C2 GSHJNEGTRIPBPA-UHFFFAOYSA-N 0.000 claims 2
• TWFMGPZWOWGSGR-UHFFFAOYSA-N n-hydroxy-4-(5-methyl-6h-benzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound C12=CC=CC=C2OC2=CC=CC=C2N(C)C1C1=CC=C(C(=O)NO)C=C1 TWFMGPZWOWGSGR-UHFFFAOYSA-N 0.000 claims 2
• KOULHJQETNKYCF-UHFFFAOYSA-N n-hydroxy-4-[11-(2-methoxyethyl)benzo[b][1,4]benzodiazepin-6-yl]benzamide Chemical compound C12=CC=CC=C2N(CCOC)C2=CC=CC=C2N=C1C1=CC=C(C(=O)NO)C=C1 KOULHJQETNKYCF-UHFFFAOYSA-N 0.000 claims 2
• HYEWDJMTXPGBCL-UHFFFAOYSA-N n-hydroxy-4-[11-(2-morpholin-4-ylethyl)pyrido[2,3-b][1,5]benzodiazepin-5-yl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C(C1=CC=CN=C11)=NC2=CC=CC=C2N1CCN1CCOCC1 HYEWDJMTXPGBCL-UHFFFAOYSA-N 0.000 claims 2
• ZVMYBYOTJTXZQY-UHFFFAOYSA-N n-hydroxy-4-[11-(3-morpholin-4-ylpropyl)pyrido[2,3-b][1,5]benzodiazepin-5-yl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C(C1=CC=CN=C11)=NC2=CC=CC=C2N1CCCN1CCOCC1 ZVMYBYOTJTXZQY-UHFFFAOYSA-N 0.000 claims 2
• SVPTYGPODUGUAW-UHFFFAOYSA-N n-hydroxy-4-[2-(trifluoromethyl)pyrido[2,3-b][1,4]benzoxazepin-6-yl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=C(C(F)(F)F)N=C2OC2=CC=CC=C12 SVPTYGPODUGUAW-UHFFFAOYSA-N 0.000 claims 2
• FGAFKSDSOGGPBU-UHFFFAOYSA-N n-hydroxy-4-pyrido[2,3-b][1,4]benzoxazepin-6-ylbenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CN=C2OC2=CC=CC=C12 FGAFKSDSOGGPBU-UHFFFAOYSA-N 0.000 claims 2
• JYOKZHJKOSRRKG-UHFFFAOYSA-N n-hydroxy-4-thieno[2,3-b][1,4]benzoxazepin-5-ylbenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C(C1=CC=CC=C1O1)=NC2=C1SC=C2 JYOKZHJKOSRRKG-UHFFFAOYSA-N 0.000 claims 2
• XXSCZLYVZGYRED-UHFFFAOYSA-N 4-(1-fluorobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC(F)=C2OC2=CC=CC=C12 XXSCZLYVZGYRED-UHFFFAOYSA-N 0.000 claims 1
• MRGXGGLDIYJMRZ-UHFFFAOYSA-N 4-(4-fluorobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=C(F)C=CC=C2OC2=CC=CC=C12 MRGXGGLDIYJMRZ-UHFFFAOYSA-N 0.000 claims 1
• CDTPXVCLRSOULN-UHFFFAOYSA-N 4-(8-fluorobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC=C(F)C=C12 CDTPXVCLRSOULN-UHFFFAOYSA-N 0.000 claims 1
• QQPFLTPCDJUVPH-UHFFFAOYSA-N 4-(9-fluorobenzo[b][1,4]benzoxazepin-6-yl)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC(F)=CC=C12 QQPFLTPCDJUVPH-UHFFFAOYSA-N 0.000 claims 1
• JVDCTJQKJALJKL-UHFFFAOYSA-N 4-[[(11-cyclopropylbenzo[b][1,4]benzodiazepin-6-yl)amino]methyl]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1CNC(C1=CC=CC=C11)=NC2=CC=CC=C2N1C1CC1 JVDCTJQKJALJKL-UHFFFAOYSA-N 0.000 claims 1
• UYBZZOOAOUTZLY-UHFFFAOYSA-N 6-benzo[b][1,4]benzoxazepin-6-yl-N-hydroxypyridine-3-carboxamide Chemical compound N1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CC=CC=C12 UYBZZOOAOUTZLY-UHFFFAOYSA-N 0.000 claims 1
• CZPQCNFJXPEFHJ-UHFFFAOYSA-N C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CN=CC=C12 Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=CN=CC=C12 CZPQCNFJXPEFHJ-UHFFFAOYSA-N 0.000 claims 1
• YYSROEIXBWVVLS-UHFFFAOYSA-N n-hydroxy-4-(10-hydroxybenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1C1=NC2=CC=CC=C2OC2=C(O)C=CC=C12 YYSROEIXBWVVLS-UHFFFAOYSA-N 0.000 claims 1
• AWLZZGOVXAZLEP-UHFFFAOYSA-N n-hydroxy-4-(10-methoxybenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound COC1=CC=CC2=C1OC1=CC=CC=C1N=C2C1=CC=C(C(=O)NO)C=C1 AWLZZGOVXAZLEP-UHFFFAOYSA-N 0.000 claims 1
• QTRWGUUPAGAJQM-UHFFFAOYSA-N n-hydroxy-4-(10-methylbenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound CC1=CC=CC2=C1OC1=CC=CC=C1N=C2C1=CC=C(C(=O)NO)C=C1 QTRWGUUPAGAJQM-UHFFFAOYSA-N 0.000 claims 1
• AXEMYCOCQPCWCL-UHFFFAOYSA-N n-hydroxy-4-(10-methylsulfanylbenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound CSC1=CC=CC2=C1OC1=CC=CC=C1N=C2C1=CC=C(C(=O)NO)C=C1 AXEMYCOCQPCWCL-UHFFFAOYSA-N 0.000 claims 1
• JAVWERMJFSKKLJ-UHFFFAOYSA-N n-hydroxy-4-(10-methylsulfonylbenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound CS(=O)(=O)C1=CC=CC2=C1OC1=CC=CC=C1N=C2C1=CC=C(C(=O)NO)C=C1 JAVWERMJFSKKLJ-UHFFFAOYSA-N 0.000 claims 1
• UQMKWABHGRBZLV-UHFFFAOYSA-N n-hydroxy-4-(3-methylbenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound N=1C2=CC(C)=CC=C2OC2=CC=CC=C2C=1C1=CC=C(C(=O)NO)C=C1 UQMKWABHGRBZLV-UHFFFAOYSA-N 0.000 claims 1
• WYLRWJWDVNAFGA-UHFFFAOYSA-N n-hydroxy-4-(7-methoxybenzo[b][1,4]benzoxazepin-6-yl)benzamide Chemical compound C1=2C(OC)=CC=CC=2OC2=CC=CC=C2N=C1C1=CC=C(C(=O)NO)C=C1 WYLRWJWDVNAFGA-UHFFFAOYSA-N 0.000 claims 1
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