HRP20090402T1 - N-sulfonilpiroli i njihova upotreba kao inhibitori histon-deacetilaze - Google Patents
N-sulfonilpiroli i njihova upotreba kao inhibitori histon-deacetilaze Download PDFInfo
- Publication number
- HRP20090402T1 HRP20090402T1 HR20090402T HRP20090402T HRP20090402T1 HR P20090402 T1 HRP20090402 T1 HR P20090402T1 HR 20090402 T HR20090402 T HR 20090402T HR P20090402 T HRP20090402 T HR P20090402T HR P20090402 T1 HRP20090402 T1 HR P20090402T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyrrol
- phenyl
- group
- sulfonyl
- acrylamide
- Prior art date
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- 239000003276 histone deacetylase inhibitor Substances 0.000 title claims abstract 3
- 229940121372 histone deacetylase inhibitor Drugs 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract 47
- -1 1-4C-alkyl Inorganic materials 0.000 claims 178
- 229910052739 hydrogen Inorganic materials 0.000 claims 77
- 239000001257 hydrogen Substances 0.000 claims 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 66
- 150000002431 hydrogen Chemical group 0.000 claims 57
- 125000001072 heteroaryl group Chemical group 0.000 claims 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 44
- 125000003118 aryl group Chemical group 0.000 claims 39
- 229910052757 nitrogen Inorganic materials 0.000 claims 35
- 229910052760 oxygen Inorganic materials 0.000 claims 29
- 239000001301 oxygen Substances 0.000 claims 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 28
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 150000002367 halogens Chemical class 0.000 claims 22
- 125000005842 heteroatom Chemical group 0.000 claims 22
- 229910052717 sulfur Inorganic materials 0.000 claims 22
- 239000011593 sulfur Substances 0.000 claims 22
- 150000003254 radicals Chemical class 0.000 claims 21
- 206010028980 Neoplasm Diseases 0.000 claims 20
- 125000001624 naphthyl group Chemical group 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 201000011510 cancer Diseases 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 8
- 239000002246 antineoplastic agent Substances 0.000 claims 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 125000001544 thienyl group Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 6
- 206010060999 Benign neoplasm Diseases 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 102000002689 Toll-like receptor Human genes 0.000 claims 3
- 108020000411 Toll-like receptor Proteins 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 230000003463 hyperproliferative effect Effects 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 230000000116 mitigating effect Effects 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- RATPPLMRKJEMEQ-MDZDMXLPSA-N (e)-3-[1-[3-[3-[(dimethylamino)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound CN(C)CC1=CC=CC(C=2C=C(C=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=C1 RATPPLMRKJEMEQ-MDZDMXLPSA-N 0.000 claims 2
- JIEPDGVAQKLGAH-SOFGYWHQSA-N (e)-3-[1-[5-[3-[(dimethylamino)methyl]phenyl]thiophen-2-yl]sulfonylpyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound CN(C)CC1=CC=CC(C=2SC(=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=C1 JIEPDGVAQKLGAH-SOFGYWHQSA-N 0.000 claims 2
- JAIWXOBNFOYQQK-RMKNXTFCSA-N (e)-n-hydroxy-3-[1-[3-[4-(2-morpholin-4-ylethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=CC(C=2C=CC(CCN3CCOCC3)=CC=2)=C1 JAIWXOBNFOYQQK-RMKNXTFCSA-N 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 claims 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims 2
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- 208000017604 Hodgkin disease Diseases 0.000 claims 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 2
- 229940124613 TLR 7/8 agonist Drugs 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000000556 agonist Substances 0.000 claims 2
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 229960000397 bevacizumab Drugs 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 229960001467 bortezomib Drugs 0.000 claims 2
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 claims 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 230000000973 chemotherapeutic effect Effects 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims 2
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- 229960002584 gefitinib Drugs 0.000 claims 2
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- 230000006882 induction of apoptosis Effects 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 229960000435 oblimersen Drugs 0.000 claims 2
- MIMNFCVQODTQDP-NDLVEFNKSA-N oblimersen Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(S)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C3=NC=NC(N)=C3N=C2)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(N=C(N)C=C2)=O)COP(O)(=S)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 MIMNFCVQODTQDP-NDLVEFNKSA-N 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
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- AYUNIORJHRXIBJ-TXHRRWQRSA-N tanespimycin Chemical compound N1C(=O)\C(C)=C\C=C/[C@H](OC)[C@@H](OC(N)=O)\C(C)=C\[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC2=C(NCC=C)C(=O)C=C1C2=O AYUNIORJHRXIBJ-TXHRRWQRSA-N 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
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- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 claims 2
- 229960000604 valproic acid Drugs 0.000 claims 2
- ZGNLFUXWZJGETL-YUSKDDKASA-N (Z)-[(2S)-2-amino-2-carboxyethyl]-hydroxyimino-oxidoazanium Chemical compound N[C@@H](C\[N+]([O-])=N\O)C(O)=O ZGNLFUXWZJGETL-YUSKDDKASA-N 0.000 claims 1
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- XDWNFBJBYNBVDF-OVCLIPMQSA-N (e)-3-[1-[4-[4-(acetamidomethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]-n-(2-aminophenyl)prop-2-enamide Chemical compound C1=CC(CNC(=O)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)C=C1 XDWNFBJBYNBVDF-OVCLIPMQSA-N 0.000 claims 1
- WEVBEJTZDBSNPK-VGOFMYFVSA-N (e)-3-[1-[4-[4-[(cyclopentylamino)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=C(C=2C=CC(CNC3CCCC3)=CC=2)C=C1 WEVBEJTZDBSNPK-VGOFMYFVSA-N 0.000 claims 1
- DXMQHUUVNLUZKF-LFYBBSHMSA-N (e)-3-[1-[4-[4-[(dimethylamino)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)C=C1 DXMQHUUVNLUZKF-LFYBBSHMSA-N 0.000 claims 1
- DFENEPCNDNLTNI-GQCTYLIASA-N (e)-3-[1-[5-[3-(aminomethyl)phenyl]thiophen-2-yl]sulfonylpyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound NCC1=CC=CC(C=2SC(=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=C1 DFENEPCNDNLTNI-GQCTYLIASA-N 0.000 claims 1
- PZLGCPXPNMJBGE-XYOKQWHBSA-N (e)-3-[1-[5-[4-(acetamidomethyl)phenyl]thiophen-2-yl]sulfonylpyrrol-3-yl]-n-(2-aminophenyl)prop-2-enamide Chemical compound C1=CC(CNC(=O)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)S1 PZLGCPXPNMJBGE-XYOKQWHBSA-N 0.000 claims 1
- RIZOFWIVXSKUHY-YCRREMRBSA-N (e)-3-[1-[5-[4-(dimethylsulfamoyl)phenyl]thiophen-2-yl]sulfonylpyrrol-3-yl]-n-hydroxyprop-2-enamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)S1 RIZOFWIVXSKUHY-YCRREMRBSA-N 0.000 claims 1
- JNNQXNXMJCILKJ-MDZDMXLPSA-N (e)-n-(2-aminophenyl)-3-[1-[3-(1-methylpyrazol-4-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NN(C)C=C1C1=CC=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 JNNQXNXMJCILKJ-MDZDMXLPSA-N 0.000 claims 1
- LZLQYTCZLUNMIZ-DHZHZOJOSA-N (e)-n-(2-aminophenyl)-3-[1-[3-(6-aminopyridin-3-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NC(N)=CC=C1C1=CC=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 LZLQYTCZLUNMIZ-DHZHZOJOSA-N 0.000 claims 1
- OTKWBPIAPHFNCM-PKNBQFBNSA-N (e)-n-(2-aminophenyl)-3-[1-[3-(6-methoxypyridin-3-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NC(OC)=CC=C1C1=CC=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 OTKWBPIAPHFNCM-PKNBQFBNSA-N 0.000 claims 1
- PPUBZNGPHHFWLE-VAWYXSNFSA-N (e)-n-(2-aminophenyl)-3-[1-[3-[3-(2-morpholin-4-ylethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound NC1=CC=CC=C1NC(=O)\C=C\C1=CN(S(=O)(=O)C=2C=C(C=CC=2)C=2C=C(CCN3CCOCC3)C=CC=2)C=C1 PPUBZNGPHHFWLE-VAWYXSNFSA-N 0.000 claims 1
- CTZMWPALOWSXBL-OUKQBFOZSA-N (e)-n-(2-aminophenyl)-3-[1-[3-[3-(methanesulfonamidomethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound CS(=O)(=O)NCC1=CC=CC(C=2C=C(C=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 CTZMWPALOWSXBL-OUKQBFOZSA-N 0.000 claims 1
- TXZQCWFHGIEXLG-BUHFOSPRSA-N (e)-n-(2-aminophenyl)-3-[1-[3-[3-[(dimethylamino)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound CN(C)CC1=CC=CC(C=2C=C(C=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 TXZQCWFHGIEXLG-BUHFOSPRSA-N 0.000 claims 1
- GUOCUMFXUFKPFH-JLHYYAGUSA-N (e)-n-(2-aminophenyl)-3-[1-[3-[4-(2-morpholin-4-ylethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound NC1=CC=CC=C1NC(=O)\C=C\C1=CN(S(=O)(=O)C=2C=C(C=CC=2)C=2C=CC(CCN3CCOCC3)=CC=2)C=C1 GUOCUMFXUFKPFH-JLHYYAGUSA-N 0.000 claims 1
- LGNRGQGJVARUBZ-NTEUORMPSA-N (e)-n-(2-aminophenyl)-3-[1-[3-[4-(methanesulfonamido)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CC=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 LGNRGQGJVARUBZ-NTEUORMPSA-N 0.000 claims 1
- HJJGRMDJHFTALI-NTCAYCPXSA-N (e)-n-(2-aminophenyl)-3-[1-[3-[4-[(dimethylamino)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 HJJGRMDJHFTALI-NTCAYCPXSA-N 0.000 claims 1
- GGKOTAFVSNHPRD-XNTDXEJSSA-N (e)-n-(2-aminophenyl)-3-[1-[4-(1-benzylpyrazol-4-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound NC1=CC=CC=C1NC(=O)\C=C\C1=CN(S(=O)(=O)C=2C=CC(=CC=2)C2=CN(CC=3C=CC=CC=3)N=C2)C=C1 GGKOTAFVSNHPRD-XNTDXEJSSA-N 0.000 claims 1
- WLCSVOAEZBVLOH-KPKJPENVSA-N (e)-n-(2-aminophenyl)-3-[1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound CC1=NOC(C)=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)C=C1 WLCSVOAEZBVLOH-KPKJPENVSA-N 0.000 claims 1
- SLFXTSQOESVJNS-LFYBBSHMSA-N (e)-n-(2-aminophenyl)-3-[1-[4-(6-aminopyridin-3-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NC(N)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)C=C1 SLFXTSQOESVJNS-LFYBBSHMSA-N 0.000 claims 1
- DQUSPCDWRMHYPD-WUXMJOGZSA-N (e)-n-(2-aminophenyl)-3-[1-[4-(6-methoxypyridin-3-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NC(OC)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)C=C1 DQUSPCDWRMHYPD-WUXMJOGZSA-N 0.000 claims 1
- LYXOTMRRZFIOCN-IZZDOVSWSA-N (e)-n-(2-aminophenyl)-3-[1-[4-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1CN(C)CCN1C1=CC(C=2C=CC(=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=CC=N1 LYXOTMRRZFIOCN-IZZDOVSWSA-N 0.000 claims 1
- YGNYTPBJGLHVBK-NTEUORMPSA-N (e)-n-(2-aminophenyl)-3-[1-[4-[3-(methanesulfonamido)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 YGNYTPBJGLHVBK-NTEUORMPSA-N 0.000 claims 1
- RPKFDDRHNSJCJK-XNTDXEJSSA-N (e)-n-(2-aminophenyl)-3-[1-[4-[3-[(dimethylamino)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound CN(C)CC1=CC=CC(C=2C=CC(=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 RPKFDDRHNSJCJK-XNTDXEJSSA-N 0.000 claims 1
- DLIUBMRCVGSEII-FRKPEAEDSA-N (e)-n-(2-aminophenyl)-3-[1-[4-[4-(2-pyrrolidin-1-ylethoxy)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound NC1=CC=CC=C1NC(=O)\C=C\C1=CN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC(OCCN3CCCC3)=CC=2)C=C1 DLIUBMRCVGSEII-FRKPEAEDSA-N 0.000 claims 1
- APZNYPMXWCHTND-FRKPEAEDSA-N (e)-n-(2-aminophenyl)-3-[1-[4-[4-(dimethylsulfamoyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)C=C1 APZNYPMXWCHTND-FRKPEAEDSA-N 0.000 claims 1
- CGTSKUXRMRKTON-GIDUJCDVSA-N (e)-n-(2-aminophenyl)-3-[1-[4-[4-(methanesulfonamido)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)C=C1 CGTSKUXRMRKTON-GIDUJCDVSA-N 0.000 claims 1
- QXZFAEVCBWOKBC-VGOFMYFVSA-N (e)-n-(2-aminophenyl)-3-[1-[4-[4-(morpholin-4-ylmethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound NC1=CC=CC=C1NC(=O)\C=C\C1=CN(S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC(CN3CCOCC3)=CC=2)C=C1 QXZFAEVCBWOKBC-VGOFMYFVSA-N 0.000 claims 1
- PIGPKWAVSNZDRE-CXUHLZMHSA-N (e)-n-(2-aminophenyl)-3-[1-[4-[4-[(dimethylamino)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)C=C1 PIGPKWAVSNZDRE-CXUHLZMHSA-N 0.000 claims 1
- XSEWTFMQPVKSSS-ZRDIBKRKSA-N (e)-n-(2-aminophenyl)-3-[1-[5-[3-[(dimethylamino)methyl]phenyl]thiophen-2-yl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound CN(C)CC1=CC=CC(C=2SC(=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)=C1 XSEWTFMQPVKSSS-ZRDIBKRKSA-N 0.000 claims 1
- UWDCOTLPYPGTKV-UKTHLTGXSA-N (e)-n-(2-aminophenyl)-3-[1-[5-[4-[(dimethylamino)methyl]phenyl]thiophen-2-yl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)S1 UWDCOTLPYPGTKV-UKTHLTGXSA-N 0.000 claims 1
- YTXQPYSHWJJCIM-NTEUORMPSA-N (e)-n-(2-aminophenyl)-3-[1-[6-[4-[(dimethylamino)methyl]phenyl]pyridin-3-yl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NC=3C(=CC=CC=3)N)C=C2)C=N1 YTXQPYSHWJJCIM-NTEUORMPSA-N 0.000 claims 1
- QGFIFCJDQZEZEE-AATRIKPKSA-N (e)-n-hydroxy-3-[1-[3-(1-methylpyrazol-4-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NN(C)C=C1C1=CC=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=C1 QGFIFCJDQZEZEE-AATRIKPKSA-N 0.000 claims 1
- VHAIRKOIHNIRBG-FNORWQNLSA-N (e)-n-hydroxy-3-[1-[3-(6-methoxypyridin-3-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NC(OC)=CC=C1C1=CC=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=C1 VHAIRKOIHNIRBG-FNORWQNLSA-N 0.000 claims 1
- AZCZTIDEMQUJCE-JXMROGBWSA-N (e)-n-hydroxy-3-[1-[3-(methanesulfonamido)-4-phenylphenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound CS(=O)(=O)NC1=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=CC=C1C1=CC=CC=C1 AZCZTIDEMQUJCE-JXMROGBWSA-N 0.000 claims 1
- IJBOAEMNIIYUSW-AATRIKPKSA-N (e)-n-hydroxy-3-[1-[3-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1CN(C)CCN1C1=CC(C=2C=C(C=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=CC=N1 IJBOAEMNIIYUSW-AATRIKPKSA-N 0.000 claims 1
- HYPPJNMFODFEJA-BQYQJAHWSA-N (e)-n-hydroxy-3-[1-[3-[3-(2-morpholin-4-ylethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=CC(C=2C=C(CCN3CCOCC3)C=CC=2)=C1 HYPPJNMFODFEJA-BQYQJAHWSA-N 0.000 claims 1
- FOCJLVOYFAWOPR-BQYQJAHWSA-N (e)-n-hydroxy-3-[1-[3-[3-(morpholin-4-ylmethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=CC(C=2C=C(CN3CCOCC3)C=CC=2)=C1 FOCJLVOYFAWOPR-BQYQJAHWSA-N 0.000 claims 1
- VAKHPMFHTXAOTM-DHZHZOJOSA-N (e)-n-hydroxy-3-[1-[3-[4-(3-morpholin-4-ylpropyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=CC(C=2C=CC(CCCN3CCOCC3)=CC=2)=C1 VAKHPMFHTXAOTM-DHZHZOJOSA-N 0.000 claims 1
- YMHQYSFEHOVCTN-RMKNXTFCSA-N (e)-n-hydroxy-3-[1-[3-[4-(morpholin-4-ylmethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=CC(C=2C=CC(CN3CCOCC3)=CC=2)=C1 YMHQYSFEHOVCTN-RMKNXTFCSA-N 0.000 claims 1
- UGUXAUIEUSYERZ-JXMROGBWSA-N (e)-n-hydroxy-3-[1-[3-[4-[(2-methoxyethylamino)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(CNCCOC)=CC=C1C1=CC=CC(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=C1 UGUXAUIEUSYERZ-JXMROGBWSA-N 0.000 claims 1
- SFPRZBNVUYVDLD-JXMROGBWSA-N (e)-n-hydroxy-3-[1-[3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1CN(C)CCN1CC1=CC=C(C=2C=C(C=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)C=C1 SFPRZBNVUYVDLD-JXMROGBWSA-N 0.000 claims 1
- LOVHYYGRUIXWLM-BJMVGYQFSA-N (e)-n-hydroxy-3-[1-[3-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1CN(C)CCN1CCOC1=CC=C(C=2C=C(C=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)C=C1 LOVHYYGRUIXWLM-BJMVGYQFSA-N 0.000 claims 1
- YDLMRPJMXFTOOE-XNWCZRBMSA-N (e)-n-hydroxy-3-[1-[4-(1-methylindol-5-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C=1C=C2N(C)C=CC2=CC=1C(C=C1)=CC=C1S(=O)(=O)N1C=CC(\C=C\C(=O)NO)=C1 YDLMRPJMXFTOOE-XNWCZRBMSA-N 0.000 claims 1
- OVMPMAOVIOPGQC-FARCUNLSSA-N (e)-n-hydroxy-3-[1-[4-(1-methylpyrazol-4-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NN(C)C=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)C=C1 OVMPMAOVIOPGQC-FARCUNLSSA-N 0.000 claims 1
- XVTYTCMZXJUYQO-BCTAIJSYSA-N (e)-n-hydroxy-3-[1-[4-(4-hydroxyphenyl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=C(C=2C=CC(O)=CC=2)C=C1 XVTYTCMZXJUYQO-BCTAIJSYSA-N 0.000 claims 1
- FGLNYTKMCQIPDT-BIIKFXOESA-N (e)-n-hydroxy-3-[1-[4-(4-methoxyphenyl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)C=C1 FGLNYTKMCQIPDT-BIIKFXOESA-N 0.000 claims 1
- CGMBSYPJDABORR-BCTAIJSYSA-N (e)-n-hydroxy-3-[1-[4-(4-morpholin-4-ylphenyl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=C(C=2C=CC(=CC=2)N2CCOCC2)C=C1 CGMBSYPJDABORR-BCTAIJSYSA-N 0.000 claims 1
- QLABSTINQAZHRC-KRXBUXKQSA-N (e)-n-hydroxy-3-[1-[4-(6-methoxypyridin-3-yl)phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=NC(OC)=CC=C1C1=CC=C(S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)C=C1 QLABSTINQAZHRC-KRXBUXKQSA-N 0.000 claims 1
- NFHFNJVVPPCDCP-LZCJLJQNSA-N (e)-n-hydroxy-3-[1-[4-[1-(2-morpholin-4-ylethyl)triazol-4-yl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=C(C=2N=NN(CCN3CCOCC3)C=2)C=C1 NFHFNJVVPPCDCP-LZCJLJQNSA-N 0.000 claims 1
- DHZRVOHXKJPRGN-FARCUNLSSA-N (e)-n-hydroxy-3-[1-[4-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1CN(C)CCN1C1=CC(C=2C=CC(=CC=2)S(=O)(=O)N2C=C(\C=C\C(=O)NO)C=C2)=CC=N1 DHZRVOHXKJPRGN-FARCUNLSSA-N 0.000 claims 1
- ZZILWFMTDDGPFP-RUDMXATFSA-N (e)-n-hydroxy-3-[1-[4-[3-(2-morpholin-4-ylethyl)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=C(C=2C=C(CCN3CCOCC3)C=CC=2)C=C1 ZZILWFMTDDGPFP-RUDMXATFSA-N 0.000 claims 1
- XSRZGJVLPKEFPU-IZZDOVSWSA-N (e)-n-hydroxy-3-[1-[4-[3-(2-pyrrolidin-1-ylethoxy)phenyl]phenyl]sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=C(C=2C=C(OCCN3CCCC3)C=CC=2)C=C1 XSRZGJVLPKEFPU-IZZDOVSWSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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US8062891B2 (en) | 2003-10-24 | 2011-11-22 | Gencia Corporation | Nonviral vectors for delivering polynucleotides to plants |
US20090123468A1 (en) | 2003-10-24 | 2009-05-14 | Gencia Corporation | Transducible polypeptides for modifying metabolism |
US8507277B2 (en) | 2003-10-24 | 2013-08-13 | Gencia Corporation | Nonviral vectors for delivering polynucleotides |
US8039587B2 (en) | 2003-10-24 | 2011-10-18 | Gencia Corporation | Methods and compositions for delivering polynucleotides |
US8133733B2 (en) | 2003-10-24 | 2012-03-13 | Gencia Corporation | Nonviral vectors for delivering polynucleotides to target tissues |
EP2272827A1 (en) * | 2004-03-11 | 2011-01-12 | 4Sc Ag | Sulphonylpyrroles as hdac inhibitors |
US8741332B2 (en) | 2004-06-07 | 2014-06-03 | Nuvo Research Inc. | Compositions and methods for dermally treating neuropathic pain |
US8907153B2 (en) | 2004-06-07 | 2014-12-09 | Nuvo Research Inc. | Adhesive peel-forming formulations for dermal delivery of drugs and methods of using the same |
US8741333B2 (en) | 2004-06-07 | 2014-06-03 | Nuvo Research Inc. | Compositions and methods for treating dermatitis or psoriasis |
MX2007010561A (es) | 2005-03-15 | 2008-02-22 | Nycomed Gmbh | N-sulfonilpirroles y su uso como inhibidores de la histona desacetilasa. |
US20090117074A1 (en) * | 2005-04-07 | 2009-05-07 | Nycomed Gmbh | Sulfonylpyrroles as Histone Deacetylase Inhibitors |
US8188138B2 (en) * | 2005-09-21 | 2012-05-29 | 4Sc Ag | Sulphonylpyrrole hydrochloride salts as histone deacetylases inhibitors |
WO2007039404A1 (en) * | 2005-09-21 | 2007-04-12 | Nycomed Gmbh | Novel sulphonylpyrroles as inhibitors of hdac s novel sulphonylpyrroles |
JP2010518013A (ja) * | 2007-02-01 | 2010-05-27 | ジェネンテック, インコーポレイテッド | 血管形成阻害剤を含む組み合わせ治療の方法 |
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