JP2017535536A5 - - Google Patents
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- JP2017535536A5 JP2017535536A5 JP2017522120A JP2017522120A JP2017535536A5 JP 2017535536 A5 JP2017535536 A5 JP 2017535536A5 JP 2017522120 A JP2017522120 A JP 2017522120A JP 2017522120 A JP2017522120 A JP 2017522120A JP 2017535536 A5 JP2017535536 A5 JP 2017535536A5
- Authority
- JP
- Japan
- Prior art keywords
- carbazole
- carboxamide
- fluoro
- tetrahydro
- hydroxypropan
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 methylpiperazinyl Chemical group 0.000 claims 40
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 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
- ZCFPOJLRORWBHW-UHFFFAOYSA-N 7,7-dimethyl-4-[2-methyl-3-(prop-2-enoylamino)phenyl]-5,6,8,9-tetrahydrocarbazole-1-carboxamide Chemical compound C(C=C)(=O)NC=1C(=C(C=CC=1)C1=C2C=3CCC(CC=3NC2=C(C=C1)C(=O)N)(C)C)C ZCFPOJLRORWBHW-UHFFFAOYSA-N 0.000 claims 3
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 3
- 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
- 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
- YRQWDRNPFKFSNL-UHFFFAOYSA-N 3-chloro-4-(1-prop-2-enoyl-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b]pyridin-6-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1C2C(CCC1)CN(C2)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)Cl YRQWDRNPFKFSNL-UHFFFAOYSA-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
- 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 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
- LPOGJGSJGIZKPZ-UHFFFAOYSA-N 3-fluoro-4-(1-prop-2-enoyl-3,3a,4,6,7,7a-hexahydro-2H-pyrrolo[3,2-c]pyridin-5-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CCC2CN(CCC21)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F LPOGJGSJGIZKPZ-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
- 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
- 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
- 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
- ULNOOGMRPJSHHE-UHFFFAOYSA-N 3-fluoro-4-(7-prop-2-enoyl-1,3,4,4a,5,6,8,8a-octahydro-2,7-naphthyridin-2-yl)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)N1CCC2CCN(CC2C1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F ULNOOGMRPJSHHE-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
- 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
- KRXGLJQLKSACOF-UHFFFAOYSA-N 3-fluoro-7-(2-hydroxypropan-2-yl)-4-[(6-prop-1-ynylpyridin-3-yl)methyl]-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound FC=1C(=C2C=3CCC(CC=3NC2=C(C=1)C(=O)N)C(C)(C)O)CC=1C=NC(=CC=1)C#CC KRXGLJQLKSACOF-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
- DWKNSSFDRIIXGH-UHFFFAOYSA-N 4-(2-cyano-3,4-dihydro-1H-isoquinolin-5-yl)-7-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide Chemical compound NC(=O)C1=CC=C(C2=C1NC1=CC(=CC=C21)C(=O)N1CCOCC1)C1=CC=CC2=C1CCN(C2)C#N DWKNSSFDRIIXGH-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
- 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 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
- SXTZWPJXCFMDMJ-CYBMUJFWSA-N 4-[(3R)-3-(but-2-ynoylamino)piperidin-1-yl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound C(C#CC)(=O)N[C@H]1CN(CCC1)C1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F SXTZWPJXCFMDMJ-CYBMUJFWSA-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
- FCAKFRRQPHFZNS-SFHVURJKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-3-fluoro-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C(C=C(C=2NC3=CC(=CC=C3C1=2)C(=O)N1CCN(CC1)C)C(=O)N)F FCAKFRRQPHFZNS-SFHVURJKSA-N 0.000 claims 2
- UAEHFWHVTOUMDS-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-3-fluoro-7-(trifluoromethyl)-9H-carbazole-1-carboxamide Chemical compound C(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 UAEHFWHVTOUMDS-ZDUSSCGKSA-N 0.000 claims 2
- KPVJEUAQOIATCX-HNNXBMFYSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-3-fluoro-7-N,7-N-dimethyl-9H-carbazole-1,7-dicarboxamide Chemical compound CC#CC(=O)N[C@H]1CCCN(C1)C1=C(F)C=C(C(N)=O)C2=C1C1=CC=C(C=C1N2)C(=O)N(C)C KPVJEUAQOIATCX-HNNXBMFYSA-N 0.000 claims 2
- SXTZWPJXCFMDMJ-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound CC#CC(=O)N[C@H]1CCCN(C1)C1=C(F)C=C(C(N)=O)C2=C1C1=CC=CC=C1N2 SXTZWPJXCFMDMJ-ZDUSSCGKSA-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
- DOJHCEZYWNURGQ-UHFFFAOYSA-N 4-[(6-ethenylpyridin-3-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC=CC=C3C=2C=1CC=1C=NC(=CC=1)C=C)C(=O)N DOJHCEZYWNURGQ-UHFFFAOYSA-N 0.000 claims 2
- XYOVGMYEEPQYCQ-UHFFFAOYSA-N 4-[(6-ethynylpyridin-3-yl)methyl]-3-fluoro-9H-carbazole-1-carboxamide Chemical compound C(#C)C1=CC=C(C=N1)CC1=C(C=C(C=2NC3=CC=CC=C3C1=2)C(=O)N)F XYOVGMYEEPQYCQ-UHFFFAOYSA-N 0.000 claims 2
- OLFNPGUGEWXDAH-UHFFFAOYSA-N 4-[2-methyl-3-(prop-2-enoylamino)phenyl]-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)NC=1C(=C(C=CC=1)C1=C2C=3CCCCC=3NC2=C(C=C1)C(=O)N)C OLFNPGUGEWXDAH-UHFFFAOYSA-N 0.000 claims 2
- OABHEPRSPZEEEG-UHFFFAOYSA-N 4-[2-methyl-3-(prop-2-enoylamino)phenyl]-7-(propan-2-ylamino)-9H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)NC=1C(=C(C=CC=1)C1=CC=C(C=2NC3=CC(=CC=C3C1=2)NC(C)C)C(=O)N)C OABHEPRSPZEEEG-UHFFFAOYSA-N 0.000 claims 2
- BUEGAVMKFYRZND-UHFFFAOYSA-N 4-[3-(ethenylsulfonylamino)-2-methylphenyl]-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound CC1=C(C=CC=C1NS(=O)(=O)C=C)C1=C2C=3CCCCC=3NC2=C(C=C1)C(=O)N BUEGAVMKFYRZND-UHFFFAOYSA-N 0.000 claims 2
- XXRMJLHHDXTRGK-UHFFFAOYSA-N 4-[3-(ethenylsulfonylamino)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide Chemical compound OC(C)(C)C1=CC=C2C=3C(=CC=C(C=3NC2=C1)C(=O)N)C1=C(C(=CC=C1)NS(=O)(=O)C=C)C XXRMJLHHDXTRGK-UHFFFAOYSA-N 0.000 claims 2
- ZNCJSFGGEIGMLJ-UHFFFAOYSA-N 4-[3-(ethenylsulfonylamino)-2-methylphenyl]-8-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound OC(C)(C)C1CCCC=2C3=C(C=CC(=C3NC1=2)C(=O)N)C1=C(C(=CC=C1)NS(=O)(=O)C=C)C ZNCJSFGGEIGMLJ-UHFFFAOYSA-N 0.000 claims 2
- UEOGWZFJFQCZJQ-UHFFFAOYSA-N 4-[3-(ethenylsulfonylamino)phenyl]-3-fluoro-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide Chemical compound FC=1C=C(C=2NC3=CC(=CC=C3C=2C=1C1=CC(=CC=C1)NS(=O)(=O)C=C)C(C)(C)O)C(=O)N UEOGWZFJFQCZJQ-UHFFFAOYSA-N 0.000 claims 2
- VVWYYBBLJSKPQO-UHFFFAOYSA-N 4-[3-(ethenylsulfonylamino)phenyl]-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound C(=C)S(=O)(=O)NC=1C=C(C=CC=1)C1=C2C=3CCCCC=3NC2=C(C=C1)C(=O)N VVWYYBBLJSKPQO-UHFFFAOYSA-N 0.000 claims 2
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Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200750A (en) | 1977-01-07 | 1980-04-29 | Westwood Pharmaceuticals Inc. | 4-Substituted imidazo [1,2-a]quinoxalines |
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| US7405295B2 (en) | 2003-06-04 | 2008-07-29 | Cgi Pharmaceuticals, Inc. | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
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| US7713973B2 (en) | 2004-10-15 | 2010-05-11 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| CA2587192A1 (en) | 2004-11-10 | 2006-05-18 | Cgi Pharmaceuticals, Inc. | Imidazo[1 , 2-a] pyrazin-8-ylamines useful as modulators of kinase activity |
| AP2334A (en) | 2004-12-17 | 2011-12-06 | Glenmark Pharmaceuticals Sa | Novel heterocyclic compounds useful for the treatment of inflamatory and allergic disorders. |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
| US8518964B2 (en) * | 2005-11-22 | 2013-08-27 | Merck Sharp & Dohme Corp. | Tricyclic compounds useful as inhibitors of kinases |
| CA2663178C (en) | 2006-09-11 | 2016-01-12 | Matrix Laboratories Ltd. | Dibenzofuran derivatives as inhibitors of pde-4 and pde-10 |
| WO2008033858A2 (en) | 2006-09-11 | 2008-03-20 | Cgi Pharmaceuticals, Inc. | Kinase inhibitors, and methods of using and identifying kinase inhibitors |
| US20090062251A1 (en) | 2007-08-17 | 2009-03-05 | Astrazeneca Ab | Novel Compounds 002 |
| US7989465B2 (en) | 2007-10-19 | 2011-08-02 | Avila Therapeutics, Inc. | 4,6-disubstituted pyrimidines useful as kinase inhibitors |
| EP2231143B1 (en) | 2007-12-13 | 2013-07-03 | Merck Sharp & Dohme Corp. | 5H-pyrido[4,3-b]indoles as INHIBITORS OF JANUS KINASES |
| FI2247558T4 (fi) | 2008-02-14 | 2024-09-19 | Lilly Co Eli | Uusia kuvantamisaineita neurologisen toimintahäiriön toteamiseen |
| GB0809360D0 (en) | 2008-05-22 | 2008-07-02 | Isis Innovation | Calcium modulation |
| TW201010997A (en) | 2008-06-18 | 2010-03-16 | Pfizer Ltd | Nicotinamide derivatives |
| MX382352B (es) | 2008-06-27 | 2025-03-13 | Celgene Car Llc | Compuestos de heteroarilo y usos de los mismos. |
| EP2151441A1 (en) | 2008-08-06 | 2010-02-10 | Julius-Maximilians-Universität Würzburg | Beta-carbolin-derivates as substrates for an enzyme |
| EP2391602B1 (en) * | 2008-12-19 | 2013-12-04 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| CN101475571B (zh) | 2009-01-21 | 2011-06-22 | 中国药科大学 | β-咔啉类细胞周期蛋白依赖性激酶2抑制剂及其用途 |
| EP2415184B1 (en) | 2009-02-13 | 2019-04-10 | Nextivity, Inc. | Remote control for booster |
| WO2011159857A1 (en) * | 2010-06-16 | 2011-12-22 | Bristol-Myers Squibb Company | Carboline carboxamide compounds useful as kinase inhibitors |
| EP2455378A1 (en) | 2010-11-03 | 2012-05-23 | Philip Morris Products S.A. | Carbazole and carboline derivatives, and preparation and therapeutic applications thereof |
| CA2817896A1 (en) | 2010-11-15 | 2012-05-24 | Viiv Healthcare Uk Limited | Inhibitors of hiv replication |
| ES2590491T3 (es) | 2011-05-17 | 2016-11-22 | F. Hoffmann-La Roche Ag | Inhibidores de la tirosina quinasa de Bruton |
| TW201728592A (zh) | 2012-01-10 | 2017-08-16 | 林伯士艾瑞斯公司 | Ｉｒａｋ抑制劑及其用途 |
| CA2881070A1 (en) | 2012-10-26 | 2014-05-01 | F. Hoffmann-La Roche Ag | Inhibitors of bruton's tyrosine kinase |
| WO2014210087A1 (en) * | 2013-06-25 | 2014-12-31 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| UY35625A (es) * | 2013-06-25 | 2014-12-31 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos de tetrahidrocarbazol y carbazol carboxamida sustituidos como inhibidores de quinasa |
| JP6592512B2 (ja) * | 2014-10-24 | 2019-10-16 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 三環式アトロプ異性体の化合物 |
| LT3461821T (lt) | 2014-10-24 | 2020-08-10 | Bristol-Myers Squibb Company | Indolo karboksamido junginiai, naudotini kaip kinazės inhibitoriai |
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2015
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- 2015-10-23 WO PCT/US2015/057077 patent/WO2016065236A1/en not_active Ceased
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2017
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