ME03754B - Derivaтi karbazola - Google Patents
Derivaтi karbazolaInfo
- Publication number
- ME03754B ME03754B MEP-2019-363A MEP2019363A ME03754B ME 03754 B ME03754 B ME 03754B ME P2019363 A MEP2019363 A ME P2019363A ME 03754 B ME03754 B ME 03754B
- Authority
- ME
- Montenegro
- Prior art keywords
- carboxamide
- carbazole
- fluoro
- tetrahydro
- hydroxypropan
- Prior art date
Links
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 150000003839 salts Chemical class 0.000 claims 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- MDORVNBMVCGCQQ-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-5-yl)-9H-carbazole-1-carboxamide Chemical compound NC(=O)c1cc(F)c(N2CC3CCN(C3C2)C(=O)C=C)c2c3ccccc3[nH]c12 MDORVNBMVCGCQQ-UHFFFAOYSA-N 0.000 claims 3
- YXMSYMAJKTYPBA-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoylpiperidin-3-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC(CCC1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F YXMSYMAJKTYPBA-UHFFFAOYSA-N 0.000 claims 3
- JFVLRFMUHUCUFA-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoylpyrrolidin-3-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F JFVLRFMUHUCUFA-UHFFFAOYSA-N 0.000 claims 3
- VYDSXMVUDZRLRP-UHFFFAOYSA-N 4-[(2-ethenylpyridin-4-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=CC(=NC=C1)C=C)C(=O)N VYDSXMVUDZRLRP-UHFFFAOYSA-N 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- GPHIJUSJBPOPDP-OAHLLOKOSA-N (7R)-3-chloro-7-(2-hydroxypropan-2-yl)-4-[3-[methyl(prop-2-enoyl)amino]phenyl]-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound ClC=1C(=C2C=3CC[C@H](CC=3NC2=C(C=1)C(=O)N)C(C)(C)O)C1=CC(=CC=C1)N(C(C=C)=O)C GPHIJUSJBPOPDP-OAHLLOKOSA-N 0.000 claims 2
- UHIYBBMYZGVWRI-OAHLLOKOSA-N (7R)-3-fluoro-7-(2-hydroxypropan-2-yl)-4-[3-[methyl(prop-2-enoyl)amino]phenyl]-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound FC=1C(=C2C=3CC[C@H](CC=3NC2=C(C=1)C(=O)N)C(C)(C)O)C1=CC(=CC=C1)N(C(C=C)=O)C UHIYBBMYZGVWRI-OAHLLOKOSA-N 0.000 claims 2
- CILIRGHBQPMWEX-CQSZACIVSA-N (7R)-4-[(6-ethenylpyridin-3-yl)methyl]-3-fluoro-7-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound FC=1C(=C2C=3CC[C@H](CC=3NC2=C(C=1)C(=O)N)C(C)(C)O)CC=1C=NC(=CC=1)C=C CILIRGHBQPMWEX-CQSZACIVSA-N 0.000 claims 2
- ODJJHOVKEIUOKP-OAHLLOKOSA-N (7R)-4-[3-(ethenylsulfonylamino)phenyl]-7-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound OC(C)(C)[C@H]1CC=2NC3=C(C=CC(=C3C=2CC1)C1=CC(=CC=C1)NS(=O)(=O)C=C)C(=O)N ODJJHOVKEIUOKP-OAHLLOKOSA-N 0.000 claims 2
- ODJJHOVKEIUOKP-HNNXBMFYSA-N (7S)-4-[3-(ethenylsulfonylamino)phenyl]-7-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound CC(C)(O)[C@H]1CCC2=C(C1)NC1=C(C=CC(=C21)C1=CC(NS(=O)(=O)C=C)=CC=C1)C(N)=O ODJJHOVKEIUOKP-HNNXBMFYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- VKKKYHFZSZZSJM-NSHDSACASA-N 3,6,6-trifluoro-4-[(3S)-3-(prop-2-enoylamino)piperidin-1-yl]-5,7,8,9-tetrahydrocarbazole-1-carboxamide Chemical compound NC(=O)C1=C2NC3=C(CC(F)(F)CC3)C2=C(N2CCC[C@@H](C2)NC(=O)C=C)C(F)=C1 VKKKYHFZSZZSJM-NSHDSACASA-N 0.000 claims 2
- WRHFANJYODUVDY-UHFFFAOYSA-N 3-chloro-4-[(6-ethenylpyrazin-2-yl)methyl]-9H-carbazole-1-carboxamide Chemical compound ClC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=NC(=CN=C1)C=C)C(=O)N WRHFANJYODUVDY-UHFFFAOYSA-N 0.000 claims 2
- OREQUKWNMPHORC-UHFFFAOYSA-N 3-chloro-4-[(6-ethenylpyridin-3-yl)methyl]-9H-carbazole-1-carboxamide Chemical compound ClC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC=1C=NC(=CC=1)C=C)C(=O)N OREQUKWNMPHORC-UHFFFAOYSA-N 0.000 claims 2
- UUQHGVLKHQRAHF-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-1-azaspiro[4.4]nonan-8-yl)-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CCCC11CC(CC1)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(F)(F)F)C(=O)N)F UUQHGVLKHQRAHF-UHFFFAOYSA-N 0.000 claims 2
- XDONPROSFUNVFM-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-2,3-dihydroindol-4-yl)-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CCC2=C(C=CC=C12)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(F)(F)F)C(=O)N)F XDONPROSFUNVFM-UHFFFAOYSA-N 0.000 claims 2
- RZFBPBSKLLCKHN-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-2,3-dihydroindol-4-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CCC2=C(C=CC=C12)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F RZFBPBSKLLCKHN-UHFFFAOYSA-N 0.000 claims 2
- LNLXLPQVMANOIH-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-2,3-dihydroindol-6-yl)-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CCC2=CC=C(C=C12)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(F)(F)F)C(=O)N)F LNLXLPQVMANOIH-UHFFFAOYSA-N 0.000 claims 2
- RCBLDZISIVWFRD-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-2,3-dihydroindol-6-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CCC2=CC=C(C=C12)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F RCBLDZISIVWFRD-UHFFFAOYSA-N 0.000 claims 2
- XTVOUTODIACRGY-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-2,5-dihydropyrrol-3-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC(=CC1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F XTVOUTODIACRGY-UHFFFAOYSA-N 0.000 claims 2
- QBRXHPCBQRDDDE-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-3,4-dihydro-2H-pyridin-5-yl)-9H-carbazole-1-carboxamide Chemical compound NC(=O)C1=CC(F)=C(C2=C1NC1=CC=CC=C21)C1=CN(CCC1)C(=O)C=C QBRXHPCBQRDDDE-UHFFFAOYSA-N 0.000 claims 2
- JHSFOENRHZSYCZ-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-3,6-dihydro-2H-pyridin-4-yl)-9H-carbazole-1-carboxamide Chemical compound NC(=O)C1=CC(F)=C(C2=C1NC1=CC=CC=C21)C1=CCN(CC1)C(=O)C=C JHSFOENRHZSYCZ-UHFFFAOYSA-N 0.000 claims 2
- OVFOQORCGNXKKI-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-3,6-dihydro-2H-pyridin-5-yl)-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC(=CCC1)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(F)(F)F)C(=O)N)F OVFOQORCGNXKKI-UHFFFAOYSA-N 0.000 claims 2
- UWLYMWAMIDSVJA-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-3,6-dihydro-2H-pyridin-5-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC(=CCC1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F UWLYMWAMIDSVJA-UHFFFAOYSA-N 0.000 claims 2
- RTPBVXKBZPGHIX-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoylpyrrolidin-3-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC(CC1)C1=C2C=3CCCCC=3NC2=C(C=C1F)C(=O)N RTPBVXKBZPGHIX-UHFFFAOYSA-N 0.000 claims 2
- IFKMMLVTRWJHNA-UHFFFAOYSA-N 3-fluoro-4-(2-prop-2-enoyl-1,3-dihydroisoindol-4-yl)-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC2=CC=CC(=C2C1)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(F)(F)F)C(=O)N)F IFKMMLVTRWJHNA-UHFFFAOYSA-N 0.000 claims 2
- ZTFHCDYSBQJPDD-UHFFFAOYSA-N 3-fluoro-4-(2-prop-2-enoyl-1,3-dihydroisoindol-5-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC2=CC=C(C=C2C1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F ZTFHCDYSBQJPDD-UHFFFAOYSA-N 0.000 claims 2
- IIIHIATUBMXFNA-UHFFFAOYSA-N 3-fluoro-4-(2-prop-2-enoyl-2,7-diazaspiro[4.4]nonan-7-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC2(CCN(C2)C2=C(C=C(C=3NC4=CC=CC=C4C2=3)C(=O)N)F)CC1 IIIHIATUBMXFNA-UHFFFAOYSA-N 0.000 claims 2
- IBKZDUZTLNVKNO-UHFFFAOYSA-N 3-fluoro-4-(2-prop-2-enoyl-3,4-dihydro-1H-isoquinolin-6-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CC2=CC=C(C=C2CC1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F IBKZDUZTLNVKNO-UHFFFAOYSA-N 0.000 claims 2
- CMUMVTSEZOPLCZ-UHFFFAOYSA-N 3-fluoro-4-(2-prop-2-enoyl-3,4-dihydro-1H-isoquinolin-7-yl)-9H-carbazole-1-carboxamide Chemical compound NC(=O)C1=CC(F)=C(C2=C1NC1=CC=CC=C21)C1=CC2=C(CCN(C2)C(=O)C=C)C=C1 CMUMVTSEZOPLCZ-UHFFFAOYSA-N 0.000 claims 2
- GAXRIAKBJVUTJQ-UHFFFAOYSA-N 3-fluoro-4-(6-prop-2-enoyl-3,6-diazabicyclo[3.2.0]heptan-3-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1C2CN(CC2C1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F GAXRIAKBJVUTJQ-UHFFFAOYSA-N 0.000 claims 2
- CLLPDROJJKAXBI-UHFFFAOYSA-N 3-fluoro-4-[(2-prop-1-ynylpyridin-4-yl)methyl]-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=CC(=NC=C1)C#CC)C(=O)N CLLPDROJJKAXBI-UHFFFAOYSA-N 0.000 claims 2
- MIBGMXYREXAYAR-LBPRGKRZSA-N 3-fluoro-4-[(3S)-3-(prop-2-enoylamino)piperidin-1-yl]-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N[C@@H]1CN(CCC1)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(F)(F)F)C(=O)N)F MIBGMXYREXAYAR-LBPRGKRZSA-N 0.000 claims 2
- LZDZLKJWIKQOLD-LBPRGKRZSA-N 3-fluoro-4-[(3S)-3-(prop-2-enoylamino)piperidin-1-yl]-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N[C@@H]1CN(CCC1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F LZDZLKJWIKQOLD-LBPRGKRZSA-N 0.000 claims 2
- VXGSYHHXMJSKOB-UHFFFAOYSA-N 3-fluoro-4-[(6-prop-1-ynylpyridin-3-yl)methyl]-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC=1C=NC(=CC=1)C#CC)C(=O)N VXGSYHHXMJSKOB-UHFFFAOYSA-N 0.000 claims 2
- NFERXOMDFWKSMH-UHFFFAOYSA-N 3-fluoro-4-[3-(1-prop-2-enoylpyrrolidin-2-yl)phenyl]-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1C(CCC1)C=1C=C(C=CC=1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F NFERXOMDFWKSMH-UHFFFAOYSA-N 0.000 claims 2
- QIYTYQRGXFFGAX-CMDGGOBGSA-N 3-fluoro-4-[3-[(E)-3-morpholin-4-yl-3-oxoprop-1-enyl]phenyl]-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1C1=CC(=CC=C1)\C=C\C(=O)N1CCOCC1)C(=O)N QIYTYQRGXFFGAX-CMDGGOBGSA-N 0.000 claims 2
- NSQAQVPSBYZIOQ-ZHACJKMWSA-N 3-fluoro-4-[3-[(E)-3-oxo-3-pyrrolidin-1-ylprop-1-enyl]phenyl]-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1C1=CC(=CC=C1)\C=C\C(N1CCCC1)=O)C(=O)N NSQAQVPSBYZIOQ-ZHACJKMWSA-N 0.000 claims 2
- OTPHPUVNFGQPLZ-UHFFFAOYSA-N 3-fluoro-7-(2-hydroxyethyl)-4-(1-prop-2-enoyl-2,3-dihydroindol-6-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CCC2=CC=C(C=C12)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)CCO)C(=O)N)F OTPHPUVNFGQPLZ-UHFFFAOYSA-N 0.000 claims 2
- DXPUHARQYRLXIB-UHFFFAOYSA-N 3-fluoro-7-(2-hydroxypropan-2-yl)-4-(1-prop-2-enoyl-3,6-dihydro-2H-pyridin-5-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound CC(C)(O)C1CCC2=C(C1)NC1=C(C=C(F)C(=C21)C1=CCCN(C1)C(=O)C=C)C(N)=O DXPUHARQYRLXIB-UHFFFAOYSA-N 0.000 claims 2
- PJVXOFWKNBGUDH-UHFFFAOYSA-N 3-fluoro-7-(2-hydroxypropan-2-yl)-4-[3-[methyl(prop-2-enoyl)amino]phenyl]-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC(=CC=C3C=2C=1C1=CC(=CC=C1)N(C(C=C)=O)C)C(C)(C)O)C(=O)N PJVXOFWKNBGUDH-UHFFFAOYSA-N 0.000 claims 2
- ZKWVXUFDSAKPPI-UHFFFAOYSA-N 4-(1-cyano-2,3-dihydroindol-6-yl)-3-fluoro-7-(2-hydroxyethyl)-9H-carbazole-1-carboxamide Chemical compound C(#N)N1CCC2=CC=C(C=C12)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)CCO)C(=O)N)F ZKWVXUFDSAKPPI-UHFFFAOYSA-N 0.000 claims 2
- UDCPFIFJKYAQMW-UHFFFAOYSA-N 4-(2-ethenylpyridin-4-yl)-3-fluoro-7-N,7-N-dimethyl-9H-carbazole-1,7-dicarboxamide Chemical compound FC=1C=C(C=2NC3=CC(=CC=C3C=2C=1C1=CC(=NC=C1)C=C)C(=O)N(C)C)C(=O)N UDCPFIFJKYAQMW-UHFFFAOYSA-N 0.000 claims 2
- IKHQUPLMLOKSKB-UHFFFAOYSA-N 4-(2-ethenylpyridin-4-yl)-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1C1=CC(=NC=C1)C=C)C(=O)N IKHQUPLMLOKSKB-UHFFFAOYSA-N 0.000 claims 2
- RZIZHKJPLKYLSD-UHFFFAOYSA-N 4-[(2-ethenyl-1,3-thiazol-5-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=CN=C(S1)C=C)C(=O)N RZIZHKJPLKYLSD-UHFFFAOYSA-N 0.000 claims 2
- CJZVWEDZZDKEPT-UHFFFAOYSA-N 4-[(2-ethenyl-3-fluoropyridin-4-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=C(C(=NC=C1)C=C)F)C(=O)N CJZVWEDZZDKEPT-UHFFFAOYSA-N 0.000 claims 2
- GECIRIDPROMYKG-UHFFFAOYSA-N 4-[(2-ethenyl-6-methylpyridin-4-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=CC(=NC(=C1)C=C)C)C(=O)N GECIRIDPROMYKG-UHFFFAOYSA-N 0.000 claims 2
- WOBTVCHPVAJHIG-UHFFFAOYSA-N 4-[(2-ethenylpyrimidin-5-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC=1C=NC(=NC=1)C=C)C(=O)N WOBTVCHPVAJHIG-UHFFFAOYSA-N 0.000 claims 2
- IWBUYUBTIGRLBZ-UHFFFAOYSA-N 4-[(2-ethynylpyridin-4-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound C(#C)C1=NC=CC(=C1)CC1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F IWBUYUBTIGRLBZ-UHFFFAOYSA-N 0.000 claims 2
- BENQUMBUKRARGT-HNNXBMFYSA-N 4-[(3S)-3-(3-cyclopropylprop-2-ynoylamino)piperidin-1-yl]-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound C1(CC1)C#CC(=O)N[C@@H]1CN(CCC1)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(F)(F)F)C(=O)N)F BENQUMBUKRARGT-HNNXBMFYSA-N 0.000 claims 2
- AWAHRKAPZKNRAS-HNNXBMFYSA-N 4-[(3S)-3-(3-cyclopropylprop-2-ynoylamino)piperidin-1-yl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound C1(CC1)C#CC(=O)N[C@@H]1CN(CCC1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F AWAHRKAPZKNRAS-HNNXBMFYSA-N 0.000 claims 2
- HTLGBNQAYYWFER-NSHDSACASA-N 4-[(3S)-3-(cyanoamino)piperidin-1-yl]-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound N(C#N)[C@@H]1CN(CCC1)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(F)(F)F)C(=O)N)F HTLGBNQAYYWFER-NSHDSACASA-N 0.000 claims 2
- BJTGKHNKSIESIG-UHFFFAOYSA-N 4-[(4-ethenyl-6-methylpyrimidin-2-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=NC(=CC(=N1)C)C=C)C(=O)N BJTGKHNKSIESIG-UHFFFAOYSA-N 0.000 claims 2
- SHHFUXFPXHOSAJ-UHFFFAOYSA-N 4-[(5-ethenylpyrazin-2-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=NC=C(N=C1)C=C)C(=O)N SHHFUXFPXHOSAJ-UHFFFAOYSA-N 0.000 claims 2
- UKNOZDXWOXGULI-UHFFFAOYSA-N 4-[(6-ethenyl-2-methylpyrimidin-4-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=NC(=NC(=C1)C=C)C)C(=O)N UKNOZDXWOXGULI-UHFFFAOYSA-N 0.000 claims 2
- LSOHKRBHVYBVSM-UHFFFAOYSA-N 4-[(6-ethenylpyrazin-2-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC1=NC(=CN=C1)C=C)C(=O)N LSOHKRBHVYBVSM-UHFFFAOYSA-N 0.000 claims 2
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- 238000002560 therapeutic procedure Methods 0.000 claims 2
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- ZCIRGAROIKDISM-UHFFFAOYSA-N 3-fluoro-7-(2-hydroxypropan-2-yl)-4-(2-prop-2-enoyl-3,4-dihydro-1H-isoquinolin-5-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound CC(C)(O)C1CCC2=C(C1)NC1=C(C=C(F)C(=C21)C1=CC=CC2=C1CCN(C2)C(=O)C=C)C(N)=O ZCIRGAROIKDISM-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JSKWYLVCQJZJHZ-UHFFFAOYSA-N 4-[3-(ethenylsulfonylamino)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound OC(C)(C)C1CC=2NC3=C(C=CC(=C3C=2CC1)C1=C(C(=CC=C1)NS(=O)(=O)C=C)C)C(=O)N JSKWYLVCQJZJHZ-UHFFFAOYSA-N 0.000 claims 1
- SKVLMYYTBNCHLF-KIYNQFGBSA-N 4-[[(3S)-1-prop-2-ynoylpyrrolidin-3-yl]amino]-7-(trifluoromethyl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound C(C#C)(=O)N1C[C@H](CC1)NC1=C2C=3CCC(CC=3NC2=C(C=C1)C(=O)N)C(F)(F)F SKVLMYYTBNCHLF-KIYNQFGBSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- LBOSVANRNBQPOK-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-(2-prop-2-enoyl-3,4-dihydro-1H-isoquinolin-5-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound CC(C)(O)C1CCC2=C(C1)NC1=C(C=CC(=C21)C1=CC=CC2=C1CCN(C2)C(=O)C=C)C(N)=O LBOSVANRNBQPOK-UHFFFAOYSA-N 0.000 claims 1
- LGNCQLWKYHSWDS-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[3-(prop-2-enoylamino)-4-(trifluoromethoxy)phenyl]-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1OC(F)(F)F)C1=C2C=3CCC(CC=3NC2=C(C=C1)C(=O)N)C(C)(C)O LGNCQLWKYHSWDS-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000037976 chronic inflammation Diseases 0.000 claims 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
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| US201462068234P | 2014-10-24 | 2014-10-24 | |
| PCT/US2015/057077 WO2016065236A1 (en) | 2014-10-24 | 2015-10-23 | Carbazole derivatives |
| EP15790408.7A EP3209651B9 (en) | 2014-10-24 | 2015-10-23 | Carbazole derivatives |
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| ME03754B true ME03754B (me) | 2021-04-20 |
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| RS61504B1 (sr) | 2014-10-24 | 2021-03-31 | Takeda Pharmaceuticals Co | Jedinjenja heteroarila za lečenje oftalmičkih bolesti |
| CA2965516A1 (en) * | 2014-10-24 | 2016-04-28 | Bristol-Myers Squibb Company | Tricyclic atropisomer compounds |
| ES2965081T3 (es) * | 2016-07-07 | 2024-04-11 | Daewoong Pharmaceutical Co Ltd | Derivados 4-aminopirazolo[3,4-d]pirimidinil-azabiciclo y composición farmacéutica que comprende dichos derivados |
| GB201616627D0 (en) | 2016-09-30 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| WO2019075386A1 (en) | 2017-10-13 | 2019-04-18 | The Regents Of The University Of California | MODULATORS OF MTORC1 |
| CN109053542A (zh) * | 2018-07-25 | 2018-12-21 | 南通大学 | 一种6-溴-5-羟基异吲哚啉-1-酮的化学合成方法 |
| JP7545467B2 (ja) * | 2019-10-04 | 2024-09-04 | ブリストル-マイヤーズ スクイブ カンパニー | 置換カルバゾール化合物 |
| CN110862396B (zh) * | 2019-11-29 | 2021-06-04 | 浙江工业大学 | 一种吡咯并[3,4-c]咔唑-1,3(2H,6H)-二酮类化合物的合成方法 |
| AU2021253584A1 (en) * | 2020-04-10 | 2022-11-17 | Gb005, Inc. | Kinase inhibitors |
| AU2021283916A1 (en) * | 2020-06-02 | 2023-01-05 | Vidya Therapeutics, Inc. | Kinase inhibitors |
| CN115232061B (zh) * | 2021-09-18 | 2024-01-30 | 山西紫罗蓝新材料科技有限公司 | 一种3-硝基-9-乙基咔唑粗产物的提取工艺 |
| IL317988A (en) * | 2022-07-06 | 2025-02-01 | Vividion Therapeutics Inc | Pharmaceutical preparations comprising helix inhibitors of |
| TW202430506A (zh) * | 2022-09-29 | 2024-08-01 | 美商維維迪昂醫療公司 | 抑制劑及其用途 |
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| WO2005005429A1 (en) | 2003-06-30 | 2005-01-20 | Cellular Genomics, Inc. | Certain heterocyclic substituted imidazo[1,2-a]pyrazin-8-ylamines and methods of inhibition of bruton’s tyrosine kinase by such compounds |
| US20050288295A1 (en) | 2003-11-11 | 2005-12-29 | Currie Kevin S | Certain imidazo[1,2-a]pyrazin-8-ylamines, method of making, and method of use thereof |
| US7713973B2 (en) | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| EP1812442A2 (en) | 2004-11-10 | 2007-08-01 | CGI Pharmaceuticals, Inc. | Imidazo[1,2-a]pyrazin-8-ylamines useful as modulators of kinase activity |
| EA014956B1 (ru) | 2004-12-17 | 2011-04-29 | ГЛЕНМАРК ФАРМАСЬЮТИКАЛС Эс.Эй. | Гетероциклические соединения, применяемые для лечения воспалительных и аллергических нарушений |
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| BRPI0922565A2 (pt) * | 2008-12-19 | 2015-12-15 | Bristol Myers Squibb Co | compostos de carbazol carboxamida úteis como inibidores de cinase |
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| CA2965516A1 (en) * | 2014-10-24 | 2016-04-28 | Bristol-Myers Squibb Company | Tricyclic atropisomer compounds |
| PT3461821T (pt) | 2014-10-24 | 2020-08-05 | Bristol Myers Squibb Co | Compostos de indol carboxamida úteis como inibidores de quinase |
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