HRP20090487T1 - Hidroksamati kao terapeutski agensi - Google Patents
Hidroksamati kao terapeutski agensi Download PDFInfo
- Publication number
- HRP20090487T1 HRP20090487T1 HR20090487T HRP20090487T HRP20090487T1 HR P20090487 T1 HRP20090487 T1 HR P20090487T1 HR 20090487 T HR20090487 T HR 20090487T HR P20090487 T HRP20090487 T HR P20090487T HR P20090487 T1 HRP20090487 T1 HR P20090487T1
- Authority
- HR
- Croatia
- Prior art keywords
- hydroxy
- benzamide
- ethoxy
- ylcarbonylamino
- benzofuran
- Prior art date
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- 239000003814 drug Substances 0.000 title claims 4
- 229940124597 therapeutic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 34
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 6
- 102000003964 Histone deacetylase Human genes 0.000 claims abstract 4
- 108090000353 Histone deacetylase Proteins 0.000 claims abstract 4
- 201000010099 disease Diseases 0.000 claims abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 3
- 208000005176 Hepatitis C Diseases 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 126
- -1 ethylene, propylene, 1-methylpropylene, 2-methylpropylene Chemical group 0.000 claims 42
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 25
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims 2
- LRZXSHJICUSCIN-UHFFFAOYSA-N 5-(1-cyclopropylpiperidin-4-yl)oxy-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC2=CC(OC3CCN(CC3)C3CC3)=CC=C2O1 LRZXSHJICUSCIN-UHFFFAOYSA-N 0.000 claims 2
- 229940126190 DNA methyltransferase inhibitor Drugs 0.000 claims 2
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- 229940123468 Transferase inhibitor Drugs 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 2
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims 2
- 230000001028 anti-proliverative effect Effects 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000002254 cytotoxic agent Substances 0.000 claims 2
- 229940127089 cytotoxic agent Drugs 0.000 claims 2
- 231100000599 cytotoxic agent Toxicity 0.000 claims 2
- 239000003968 dna methyltransferase inhibitor Substances 0.000 claims 2
- 239000002834 estrogen receptor modulator Substances 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000004030 hiv protease inhibitor Substances 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- WJLXGQNDTIJVIN-UPMCQBDUSA-N n-hydroxy-4-[(2r)-3-phenyl-2-[[(e)-3-phenylprop-2-enoyl]amino]propoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OC[C@H](NC(=O)\C=C\C=1C=CC=CC=1)CC1=CC=CC=C1 WJLXGQNDTIJVIN-UPMCQBDUSA-N 0.000 claims 2
- FYJRCIFDFCJFSG-VWGXWWAPSA-N n-hydroxy-4-[(2r)-4-methylsulfanyl-2-[[(e)-3-phenylprop-2-enoyl]amino]butoxy]benzamide Chemical compound C([C@@H](CCSC)NC(=O)\C=C\C=1C=CC=CC=1)OC1=CC=C(C(=O)NO)C=C1 FYJRCIFDFCJFSG-VWGXWWAPSA-N 0.000 claims 2
- RPZXKDRIDTWUKH-DHZHZOJOSA-N n-hydroxy-4-[2-[[(e)-3-(2-methylphenyl)prop-2-enoyl]amino]ethoxy]benzamide Chemical compound CC1=CC=CC=C1\C=C\C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 RPZXKDRIDTWUKH-DHZHZOJOSA-N 0.000 claims 2
- 102000027483 retinoid hormone receptors Human genes 0.000 claims 2
- 108091008679 retinoid hormone receptors Proteins 0.000 claims 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 2
- 239000003558 transferase inhibitor Substances 0.000 claims 2
- CVYSHGQXOVPJDD-LLVKDONJSA-N (3r)-3-hydroxy-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]pyrrolidine-1-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)N1C[C@H](O)CC1 CVYSHGQXOVPJDD-LLVKDONJSA-N 0.000 claims 1
- 125000006345 2,2,2-trifluoroethoxymethyl group Chemical group [H]C([H])(*)OC([H])([H])C(F)(F)F 0.000 claims 1
- LWCYLAVASFVIEH-UHFFFAOYSA-N 2,3-dichloro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC=CC(Cl)=C1Cl LWCYLAVASFVIEH-UHFFFAOYSA-N 0.000 claims 1
- XESIWSIINJHDIV-UHFFFAOYSA-N 2,4-difluoro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC=C(F)C=C1F XESIWSIINJHDIV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QDJHIPZZZHXEJS-UHFFFAOYSA-N 3,4-difluoro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC=C(F)C(F)=C1 QDJHIPZZZHXEJS-UHFFFAOYSA-N 0.000 claims 1
- WQNMNXAAZGGIHS-UHFFFAOYSA-N 3-(diethylaminomethyl)-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound O1C2=CC=CC=C2C(CN(CC)CC)=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 WQNMNXAAZGGIHS-UHFFFAOYSA-N 0.000 claims 1
- SPCMUBFTADOPCN-UHFFFAOYSA-N 3-[(2-fluorophenoxy)methyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=C(COC=2C(=CC=CC=2)F)C2=CC=CC=C2O1 SPCMUBFTADOPCN-UHFFFAOYSA-N 0.000 claims 1
- CBBDSQMDJTUDIZ-UHFFFAOYSA-N 3-[(4-fluorophenoxy)methyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=C(COC=2C=CC(F)=CC=2)C2=CC=CC=C2O1 CBBDSQMDJTUDIZ-UHFFFAOYSA-N 0.000 claims 1
- TWPNXPWOFUGHMH-UHFFFAOYSA-N 3-[(4-fluorophenyl)sulfanylmethyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=C(CSC=2C=CC(F)=CC=2)C2=CC=CC=C2O1 TWPNXPWOFUGHMH-UHFFFAOYSA-N 0.000 claims 1
- CPSKDJNEHCHIIK-UHFFFAOYSA-N 3-[(4-fluorophenyl)sulfinylmethyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=C(CS(=O)C=2C=CC(F)=CC=2)C2=CC=CC=C2O1 CPSKDJNEHCHIIK-UHFFFAOYSA-N 0.000 claims 1
- CWUMLIHCNDIGAW-UHFFFAOYSA-N 3-[(4-fluorophenyl)sulfonylmethyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=C(CS(=O)(=O)C=2C=CC(F)=CC=2)C2=CC=CC=C2O1 CWUMLIHCNDIGAW-UHFFFAOYSA-N 0.000 claims 1
- MAUCONCHVWBMHK-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-N-[2-[4-[(hydroxyamino)-oxomethyl]phenoxy]ethyl]-2-benzofurancarboxamide Chemical compound O1C2=CC=CC=C2C(CN(C)C)=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 MAUCONCHVWBMHK-UHFFFAOYSA-N 0.000 claims 1
- KBLOAWJPXJGFNH-UHFFFAOYSA-N 3-[[2-[2-[4-(hydroxycarbamoyl)phenoxy]ethylcarbamoyl]-1-benzofuran-3-yl]methylamino]propanoic acid Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=C(CNCCC(O)=O)C2=CC=CC=C2O1 KBLOAWJPXJGFNH-UHFFFAOYSA-N 0.000 claims 1
- LEEXPLSIPDZRNT-UHFFFAOYSA-N 3-[[[2-(hydroxyamino)-2-oxoethyl]amino]methyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound O1C2=CC=CC=C2C(CNCC(=O)NO)=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 LEEXPLSIPDZRNT-UHFFFAOYSA-N 0.000 claims 1
- VHDTWHGVSJZFJS-UHFFFAOYSA-N 3-[[benzyl(methyl)amino]methyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound C=1C=CC=CC=1CN(C)CC(C1=CC=CC=C1O1)=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 VHDTWHGVSJZFJS-UHFFFAOYSA-N 0.000 claims 1
- LHTGSOKWKKDJTK-UHFFFAOYSA-N 3-chloro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzothiophene-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=C(Cl)C2=CC=CC=C2S1 LHTGSOKWKKDJTK-UHFFFAOYSA-N 0.000 claims 1
- CTEKFMDNNUZLAZ-UHFFFAOYSA-N 3-ethoxy-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]benzamide Chemical compound CCOC1=CC=CC(C(=O)NCCOC=2C=CC(=CC=2)C(=O)NO)=C1 CTEKFMDNNUZLAZ-UHFFFAOYSA-N 0.000 claims 1
- QKJUPULAJQGBPV-UHFFFAOYSA-N 3-ethyl-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound O1C2=CC=CC=C2C(CC)=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 QKJUPULAJQGBPV-UHFFFAOYSA-N 0.000 claims 1
- MHBCKTUZMLPZPL-UHFFFAOYSA-N 3-fluoro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-4-methoxybenzamide Chemical compound C1=C(F)C(OC)=CC=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 MHBCKTUZMLPZPL-UHFFFAOYSA-N 0.000 claims 1
- SLSBYHLKDYHTEG-UHFFFAOYSA-N 3-hydroxy-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=NC=CC=C1O SLSBYHLKDYHTEG-UHFFFAOYSA-N 0.000 claims 1
- GXOFMHYSDHBUFQ-UHFFFAOYSA-N 4-(2-benzamidoethoxy)-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC=CC=C1 GXOFMHYSDHBUFQ-UHFFFAOYSA-N 0.000 claims 1
- VEFAEYCHGVFLFO-UUFSLDAJSA-N 4-[(2r)-3-benzylsulfanyl-2-[[(e)-3-phenylprop-2-enoyl]amino]propoxy]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OC[C@@H](NC(=O)\C=C\C=1C=CC=CC=1)CSCC1=CC=CC=C1 VEFAEYCHGVFLFO-UUFSLDAJSA-N 0.000 claims 1
- DUFWHDWPJFQMTA-UUFSLDAJSA-N 4-[(2r)-3-benzylsulfonyl-2-[[(e)-3-phenylprop-2-enoyl]amino]propoxy]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OC[C@@H](NC(=O)\C=C\C=1C=CC=CC=1)CS(=O)(=O)CC1=CC=CC=C1 DUFWHDWPJFQMTA-UUFSLDAJSA-N 0.000 claims 1
- PENLHRVVJGVZRO-UPMCQBDUSA-N 4-[(2r)-3-cyclohexyl-2-[[(e)-3-phenylprop-2-enoyl]amino]propoxy]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OC[C@H](NC(=O)\C=C\C=1C=CC=CC=1)CC1CCCCC1 PENLHRVVJGVZRO-UPMCQBDUSA-N 0.000 claims 1
- XJFDTZOBHUGCRD-UHFFFAOYSA-N 4-[2-[(4-cyclohex-2-en-1-yloxybenzoyl)amino]ethoxy]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C(C=C1)=CC=C1OC1C=CCCC1 XJFDTZOBHUGCRD-UHFFFAOYSA-N 0.000 claims 1
- BBCNMILSPLMUGY-KRXBUXKQSA-N 4-[2-[[(E)-3-(1,3-benzodioxol-5-yl)prop-2-enoyl]amino]ethoxy]-N-hydroxybenzamide Chemical compound ONC(C1=CC=C(C=C1)OCCNC(\C=C\C1=CC2=C(C=C1)OCO2)=O)=O BBCNMILSPLMUGY-KRXBUXKQSA-N 0.000 claims 1
- PTKSTRZNKHJPAB-SOFGYWHQSA-N 4-[2-[[(e)-3-(5-bromothiophen-2-yl)prop-2-enoyl]amino]ethoxy]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)\C=C\C1=CC=C(Br)S1 PTKSTRZNKHJPAB-SOFGYWHQSA-N 0.000 claims 1
- JEILZXMBYAPZON-BQYQJAHWSA-N 4-[2-[[(e)-3-(furan-2-yl)prop-2-enoyl]amino]ethoxy]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)\C=C\C1=CC=CO1 JEILZXMBYAPZON-BQYQJAHWSA-N 0.000 claims 1
- YNQJOABAMZEMPG-LZCJLJQNSA-N 4-[2-[[(e)-3-(furan-3-yl)prop-2-enoyl]amino]ethoxy]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)\C=C\C1=COC=C1 YNQJOABAMZEMPG-LZCJLJQNSA-N 0.000 claims 1
- KRHVWKSRJDXZIF-LFYBBSHMSA-N 4-[2-[[(e)-3-[4-(dimethylamino)phenyl]prop-2-enoyl]amino]ethoxy]-n-hydroxybenzamide Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 KRHVWKSRJDXZIF-LFYBBSHMSA-N 0.000 claims 1
- RHAAIIJTUNUHCW-UHFFFAOYSA-N 4-[2-[[2-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl)acetyl]amino]ethoxy]-n-hydroxybenzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)CN1CC2CCCCC2CC1 RHAAIIJTUNUHCW-UHFFFAOYSA-N 0.000 claims 1
- MKAZJOLBHCXTKM-UHFFFAOYSA-N 4-benzamido-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 MKAZJOLBHCXTKM-UHFFFAOYSA-N 0.000 claims 1
- AXBKVPQCKRCGNX-UHFFFAOYSA-N 4-chloro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-2-methoxybenzamide Chemical compound COC1=CC(Cl)=CC=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 AXBKVPQCKRCGNX-UHFFFAOYSA-N 0.000 claims 1
- RYHMGIBBLWZTHR-UHFFFAOYSA-N 4-hydroxy-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC2=C(O)C=CC=C2O1 RYHMGIBBLWZTHR-UHFFFAOYSA-N 0.000 claims 1
- KEPFALMJXBYEOQ-UHFFFAOYSA-N 4-tert-butyl-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 KEPFALMJXBYEOQ-UHFFFAOYSA-N 0.000 claims 1
- QAFMAXQEHBFSHQ-QGZVFWFLSA-N 5-(1-cyclopropylpiperidin-4-yl)oxy-n-[(2r)-2-[4-(hydroxycarbamoyl)phenoxy]propyl]-1-benzofuran-2-carboxamide Chemical compound C([C@@H](C)OC=1C=CC(=CC=1)C(=O)NO)NC(=O)C(OC1=CC=2)=CC1=CC=2OC(CC1)CCN1C1CC1 QAFMAXQEHBFSHQ-QGZVFWFLSA-N 0.000 claims 1
- DISACWVFSPDPOV-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]pyridine-3-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1C1=CN=CC(C(=O)NCCOC=2C=CC(=CC=2)C(=O)NO)=C1 DISACWVFSPDPOV-UHFFFAOYSA-N 0.000 claims 1
- SRYRVEZRFXDKML-UHFFFAOYSA-N 5-bromo-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]pyridine-3-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CN=CC(Br)=C1 SRYRVEZRFXDKML-UHFFFAOYSA-N 0.000 claims 1
- SGIBRTOPUZCDIT-UHFFFAOYSA-N 5-fluoro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzothiophene-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC2=CC(F)=CC=C2S1 SGIBRTOPUZCDIT-UHFFFAOYSA-N 0.000 claims 1
- IGDCPMOWUIGWMK-UHFFFAOYSA-N 5-fluoro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1h-indole-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC2=CC(F)=CC=C2N1 IGDCPMOWUIGWMK-UHFFFAOYSA-N 0.000 claims 1
- KJVCSKFLSHMYRN-UHFFFAOYSA-N 6-(4-acetamidophenoxy)-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]pyridine-2-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1OC1=CC=CC(C(=O)NCCOC=2C=CC(=CC=2)C(=O)NO)=N1 KJVCSKFLSHMYRN-UHFFFAOYSA-N 0.000 claims 1
- ZQQZUITYWQXVMS-UHFFFAOYSA-N 6-(4-aminophenoxy)-n-[2-[4-(hydroxycarbamoyl)phenyl]ethyl]pyridine-2-carboxamide Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(C(=O)NCCC=2C=CC(=CC=2)C(=O)NO)=N1 ZQQZUITYWQXVMS-UHFFFAOYSA-N 0.000 claims 1
- BLDODJFXPHMOQZ-UHFFFAOYSA-N 6-bromo-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]pyridine-2-carboxamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)C1=CC=CC(Br)=N1 BLDODJFXPHMOQZ-UHFFFAOYSA-N 0.000 claims 1
- ARGQVIRZWCBQDN-UHFFFAOYSA-N 6-fluoro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-2-methyl-3,4-dihydro-2h-quinoline-1-carboxamide Chemical compound CC1CCC2=CC(F)=CC=C2N1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 ARGQVIRZWCBQDN-UHFFFAOYSA-N 0.000 claims 1
- RFGQHRWJEYIGQL-UHFFFAOYSA-N 7-[(dimethylamino)methyl]-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide Chemical compound O1C=2C(CN(C)C)=CC=CC=2C=C1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 RFGQHRWJEYIGQL-UHFFFAOYSA-N 0.000 claims 1
- YSMXHWKTLPPEQL-UHFFFAOYSA-N 7-chloro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-4-methyl-1-benzofuran-2-carboxamide Chemical compound C=1C=2C(C)=CC=C(Cl)C=2OC=1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 YSMXHWKTLPPEQL-UHFFFAOYSA-N 0.000 claims 1
- YRJSLOFQRXSVCC-UHFFFAOYSA-N 7-fluoro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-4-(2-methoxyethoxymethyl)-1-benzofuran-2-carboxamide Chemical compound C=1C=2C(COCCOC)=CC=C(F)C=2OC=1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 YRJSLOFQRXSVCC-UHFFFAOYSA-N 0.000 claims 1
- SGRUYSAEUGBVJF-UHFFFAOYSA-N 7-fluoro-n-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-4-methyl-1-benzofuran-2-carboxamide Chemical compound C=1C=2C(C)=CC=C(F)C=2OC=1C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 SGRUYSAEUGBVJF-UHFFFAOYSA-N 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
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- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
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- XQFBSKHFPDSTRJ-MSGBMKDASA-N n-hydroxy-4-[(2r)-2-[[(e)-3-phenylprop-2-enoyl]amino]butoxy]benzamide Chemical compound C([C@@H](CC)NC(=O)\C=C\C=1C=CC=CC=1)OC1=CC=C(C(=O)NO)C=C1 XQFBSKHFPDSTRJ-MSGBMKDASA-N 0.000 claims 1
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- XWLPHESOSBBJOP-BJMVGYQFSA-N n-hydroxy-4-[2-[[(e)-3-(3-methoxyphenyl)prop-2-enoyl]amino]ethoxy]benzamide Chemical compound COC1=CC=CC(\C=C\C(=O)NCCOC=2C=CC(=CC=2)C(=O)NO)=C1 XWLPHESOSBBJOP-BJMVGYQFSA-N 0.000 claims 1
- GDVOOIZYEKHSJG-XCVCLJGOSA-N n-hydroxy-4-[2-[[(e)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]ethoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)\C=C\C1=CC=C(O)C=C1 GDVOOIZYEKHSJG-XCVCLJGOSA-N 0.000 claims 1
- CYZUYWWYNBEFQM-IZZDOVSWSA-N n-hydroxy-4-[2-[[(e)-3-(4-methylphenyl)prop-2-enoyl]amino]ethoxy]benzamide Chemical compound C1=CC(C)=CC=C1\C=C\C(=O)NCCOC1=CC=C(C(=O)NO)C=C1 CYZUYWWYNBEFQM-IZZDOVSWSA-N 0.000 claims 1
- JQWQQGMAQSTBFZ-FPYGCLRLSA-N n-hydroxy-4-[2-[[(e)-3-pyridin-3-ylprop-2-enoyl]amino]ethoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)\C=C\C1=CC=CN=C1 JQWQQGMAQSTBFZ-FPYGCLRLSA-N 0.000 claims 1
- CHMZSRNWPDWFOM-BQYQJAHWSA-N n-hydroxy-4-[2-[[(e)-3-thiophen-2-ylprop-2-enoyl]amino]ethoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)\C=C\C1=CC=CS1 CHMZSRNWPDWFOM-BQYQJAHWSA-N 0.000 claims 1
- LNBCAMBREPRYEC-LZCJLJQNSA-N n-hydroxy-4-[2-[[(e)-3-thiophen-3-ylprop-2-enoyl]amino]ethoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)\C=C\C1=CSC=C1 LNBCAMBREPRYEC-LZCJLJQNSA-N 0.000 claims 1
- RMYKQGVOWUQRAO-UHFFFAOYSA-N n-hydroxy-4-[2-[[2-(1h-indol-3-yl)acetyl]amino]ethoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)CC1=CNC2=CC=CC=C12 RMYKQGVOWUQRAO-UHFFFAOYSA-N 0.000 claims 1
- LHQAYKHJCAVZFW-UHFFFAOYSA-N n-hydroxy-4-[2-[[2-(4-pyridin-4-ylpiperazin-1-yl)acetyl]amino]ethoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCNC(=O)CN1CCN(C=2C=CN=CC=2)CC1 LHQAYKHJCAVZFW-UHFFFAOYSA-N 0.000 claims 1
- PYUKROIOVNLUHG-LFYBBSHMSA-N n-hydroxy-4-[3-[[(e)-3-(4-methoxyphenyl)prop-2-enoyl]amino]propoxy]benzamide Chemical compound C1=CC(OC)=CC=C1\C=C\C(=O)NCCCOC1=CC=C(C(=O)NO)C=C1 PYUKROIOVNLUHG-LFYBBSHMSA-N 0.000 claims 1
- PIQMOFALHKRZEB-KPKJPENVSA-N n-hydroxy-4-[3-[[(e)-3-phenylprop-2-enoyl]amino]propoxy]benzamide Chemical compound C1=CC(C(=O)NO)=CC=C1OCCCNC(=O)\C=C\C1=CC=CC=C1 PIQMOFALHKRZEB-KPKJPENVSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000004660 phenylalkylthio group Chemical group 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 229940075993 receptor modulator Drugs 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 239000000849 selective androgen receptor modulator Substances 0.000 claims 1
- 229960002317 succinimide Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract 1
Classifications
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- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
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- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
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