JP2017535536A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- -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
- XVJGYKUJNICXOO-UHFFFAOYSA-N 4-[3-(ethenylsulfonylamino)phenyl]-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=CC(=CC=C1)NS(=O)(=O)C=C XVJGYKUJNICXOO-UHFFFAOYSA-N 0.000 claims 2
- DLRBCAYTJYTPCM-UHFFFAOYSA-N 4-[3-[ethenylsulfonyl(methyl)amino]-2-fluorophenyl]-7-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound FC1=C(C=CC=C1N(S(=O)(=O)C=C)C)C1=C2C=3CCC(CC=3NC2=C(C=C1)C(=O)N)C(C)(C)O DLRBCAYTJYTPCM-UHFFFAOYSA-N 0.000 claims 2
- JLIJEMCPYYMHGK-UHFFFAOYSA-N 4-[3-[ethenylsulfonyl(methyl)amino]phenyl]-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=CC(=CC=C1)N(S(=O)(=O)C=C)C)C(=O)N JLIJEMCPYYMHGK-UHFFFAOYSA-N 0.000 claims 2
- XXDZUHXEAGWIRW-UHFFFAOYSA-N 4-[3-[ethenylsulfonyl(methyl)amino]phenyl]-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=CC(=CC=C1)N(S(=O)(=O)C=C)C XXDZUHXEAGWIRW-UHFFFAOYSA-N 0.000 claims 2
- OBTYAWVXQLQWLM-UHFFFAOYSA-N 4-[4-fluoro-3-(prop-2-enoylamino)phenyl]-7-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound C(C=C)(=O)NC=1C=C(C=CC=1F)C1=C2C=3CCC(CC=3NC2=C(C=C1)C(=O)N)C(C)(C)O OBTYAWVXQLQWLM-UHFFFAOYSA-N 0.000 claims 2
- PCDKUVLETCXEQZ-LBPRGKRZSA-N 4-[[(3S)-1-cyanopyrrolidin-3-yl]amino]-3-fluoro-7-N,7-N-dimethyl-9H-carbazole-1,7-dicarboxamide Chemical compound CN(C)C(=O)C1=CC=C2C(NC3=C2C(N[C@H]2CCN(C2)C#N)=C(F)C=C3C(N)=O)=C1 PCDKUVLETCXEQZ-LBPRGKRZSA-N 0.000 claims 2
- GZLSZGDINLJTBL-UHFFFAOYSA-N 7-(1,2-dihydroxyethyl)-4-[2-methyl-3-(prop-2-enoylamino)phenyl]-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)C(CO)O)C(=O)N)C GZLSZGDINLJTBL-UHFFFAOYSA-N 0.000 claims 2
- CBPZTKGQKULJMT-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[2-methyl-3-(prop-2-enoylamino)phenyl]-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)C(C)(C)O)C(=O)N)C CBPZTKGQKULJMT-UHFFFAOYSA-N 0.000 claims 2
- GPYZDEKHMXWLRD-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[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=3CCC(CC=3NC2=C(C=C1)C(=O)N)C(C)(C)O GPYZDEKHMXWLRD-UHFFFAOYSA-N 0.000 claims 2
- TUDUMUASQSTNEX-UHFFFAOYSA-N 7-(hydroxymethyl)-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=3CCC(CC=3NC2=C(C=C1)C(=O)N)CO)C TUDUMUASQSTNEX-UHFFFAOYSA-N 0.000 claims 2
- HBTSOHRPIFKTIF-UHFFFAOYSA-N 7-N,7-N-dimethyl-4-[2-methyl-3-(prop-2-enoylamino)phenyl]-6,7,8,9-tetrahydro-5H-carbazole-1,7-dicarboxamide Chemical compound C(C=C)(=O)NC=1C(=C(C=CC=1)C1=C2C=3CCC(CC=3NC2=C(C=C1)C(=O)N)C(=O)N(C)C)C HBTSOHRPIFKTIF-UHFFFAOYSA-N 0.000 claims 2
- NRZHWMLNYROPGA-UHFFFAOYSA-N 7-cyano-4-[2-methyl-3-(prop-2-enoylamino)phenyl]-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)C#N)C(=O)N)C NRZHWMLNYROPGA-UHFFFAOYSA-N 0.000 claims 2
- ZZBWGCGMPQCJAF-UHFFFAOYSA-N 7-methyl-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=3CCC(CC=3NC2=C(C=C1)C(=O)N)C)C ZZBWGCGMPQCJAF-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000037976 chronic inflammation Diseases 0.000 claims 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- ZPDFNWHVDXMOOQ-CQSZACIVSA-N (7R)-3-chloro-4-[3-(ethenylsulfonylamino)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-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=C(C(=CC=C1)NS(=O)(=O)C=C)C ZPDFNWHVDXMOOQ-CQSZACIVSA-N 0.000 claims 1
- FCZVETJKKSPQDP-CQSZACIVSA-N (7R)-4-[3-(ethenylsulfonylamino)-2-methylphenyl]-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)C1=C(C(=CC=C1)NS(=O)(=O)C=C)C FCZVETJKKSPQDP-CQSZACIVSA-N 0.000 claims 1
- ZIKLWUTTZVPWFQ-OAHLLOKOSA-N (7R)-4-[3-[ethenylsulfonyl(methyl)amino]-2-methylphenyl]-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)C1=C(C(=CC=C1)N(S(=O)(=O)C=C)C)C ZIKLWUTTZVPWFQ-OAHLLOKOSA-N 0.000 claims 1
- NQQRXZOPZBKCNF-NSCUHMNNSA-N (e)-but-2-enamide Chemical compound C\C=C\C(N)=O NQQRXZOPZBKCNF-NSCUHMNNSA-N 0.000 claims 1
- MBODXUXQQPORNR-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)prop-2-en-1-one Chemical compound C1=CC=C2N(C(=O)C=C)CCC2=C1 MBODXUXQQPORNR-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims 1
- SCDBTSUQWMGGMJ-UHFFFAOYSA-N 3-chloro-7-(2-hydroxypropan-2-yl)-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=3CCC(CC=3NC2=C(C=C1Cl)C(=O)N)C(C)(C)O)C SCDBTSUQWMGGMJ-UHFFFAOYSA-N 0.000 claims 1
- QEDKFLJXTGGXPT-UHFFFAOYSA-N 3-chloro-7-(2-hydroxypropan-2-yl)-7-methyl-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=C1Cl)C(=O)N)(C)C(C)(C)O)C QEDKFLJXTGGXPT-UHFFFAOYSA-N 0.000 claims 1
- SCCDFTQTVOUBKV-UHFFFAOYSA-N 3-chloro-7-(hydroxymethyl)-7-methyl-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=C1Cl)C(=O)N)(C)CO)C SCCDFTQTVOUBKV-UHFFFAOYSA-N 0.000 claims 1
- YXMBJPKIKLQZBP-UHFFFAOYSA-N 3-chloro-7-N,7-N-dimethyl-4-[2-methyl-3-(prop-2-enoylamino)phenyl]-6,7,8,9-tetrahydro-5H-carbazole-1,7-dicarboxamide Chemical compound C(C=C)(=O)NC=1C(=C(C=CC=1)C1=C2C=3CCC(CC=3NC2=C(C=C1Cl)C(=O)N)C(=O)N(C)C)C YXMBJPKIKLQZBP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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
- XAQINCXLCHQQRU-LOACHALJSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-3-fluoro-7-(2-hydroxypropan-2-yl)-6,7,8,9-tetrahydro-5H-carbazole-1-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C=3CCC(CC=3NC2=C(C=C1F)C(=O)N)C(C)(C)O XAQINCXLCHQQRU-LOACHALJSA-N 0.000 claims 1
- DMSJNBWBQPWNKD-KIYNQFGBSA-N 4-[[(3S)-1-prop-2-enoylpyrrolidin-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 DMSJNBWBQPWNKD-KIYNQFGBSA-N 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- GFHHIWFKWFBNRU-UHFFFAOYSA-N 9h-carbazole-1-carboxamide Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(=O)N GFHHIWFKWFBNRU-UHFFFAOYSA-N 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- UUWQCRSNRXGWKL-UHFFFAOYSA-N FC(F)(F)C1=C(C=2NC3=CC=CC=C3C=2C=C1)C(=O)N Chemical compound FC(F)(F)C1=C(C=2NC3=CC=CC=C3C=2C=C1)C(=O)N UUWQCRSNRXGWKL-UHFFFAOYSA-N 0.000 claims 1
- STSBIYSZXHSXHH-UHFFFAOYSA-N but-2-ynamide Chemical compound CC#CC(N)=O STSBIYSZXHSXHH-UHFFFAOYSA-N 0.000 claims 1
- 239000001273 butane Substances 0.000 claims 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 229960003857 proglumide Drugs 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462068234P | 2014-10-24 | 2014-10-24 | |
| US62/068,234 | 2014-10-24 | ||
| PCT/US2015/057077 WO2016065236A1 (en) | 2014-10-24 | 2015-10-23 | Carbazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017535536A JP2017535536A (ja) | 2017-11-30 |
| JP2017535536A5 true JP2017535536A5 (cg-RX-API-DMAC7.html) | 2018-11-08 |
| JP6599983B2 JP6599983B2 (ja) | 2019-10-30 |
Family
ID=54427879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017522120A Active JP6599983B2 (ja) | 2014-10-24 | 2015-10-23 | カルバゾール誘導体 |
Country Status (34)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA53568A (fr) | 2014-10-24 | 2022-02-23 | Takeda Pharmaceuticals Co | Médicaments pour le traitement de maladies ophtalmiques |
| ES2800173T3 (es) * | 2014-10-24 | 2020-12-28 | Bristol Myers Squibb Co | Compuestos de atropisómeros tricíclicos |
| KR102327917B1 (ko) * | 2016-07-07 | 2021-11-17 | 주식회사 대웅제약 | 신규한 4-아미노피라졸로[3,4-d]피리미디닐아자바이사이클로 유도체 및 이를 포함하는 약학 조성물 |
| 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 |
| EP4038059B1 (en) * | 2019-10-04 | 2023-09-20 | Bristol-Myers Squibb Company | Substituted carbazole compounds |
| 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 |
| US20220009920A1 (en) * | 2020-04-10 | 2022-01-13 | Gb005, Inc. | Kinase inhibitors |
| US12448363B2 (en) | 2020-06-02 | 2025-10-21 | 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 |
| KR20250034121A (ko) * | 2022-07-06 | 2025-03-10 | 비비디온 테라퓨틱스, 인코포레이티드 | Wrn 헬리케이스 억제제를 포함하는 약제학적 조성물 |
| CA3268880A1 (en) * | 2022-09-29 | 2024-04-04 | Vividion Therapeutics, Inc. | N-ACRYLOYLMORPHOLINE DERIVATIVES USED AS KEAP1 MODULATORS AND RELATED USES |
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 |
| CA2140722A1 (en) | 1994-01-24 | 1995-07-25 | Joseph A. Jakubowski | Beta-carboline thromboxane synthase inhibitors |
| 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 |
| 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 |
| WO2005047290A2 (en) | 2003-11-11 | 2005-05-26 | Cellular Genomics Inc. | Imidazo[1,2-a] pyrazin-8-ylamines as kinase inhibitors |
| WO2006044687A2 (en) | 2004-10-15 | 2006-04-27 | Takeda San Diego, Inc. | Kinase inhibitors |
| KR20070119606A (ko) | 2004-11-10 | 2007-12-20 | 씨지아이 파마슈티칼스, 인크. | 특정 이미다조[１,２-ａ]피라진-８-일아민, 그의 제조 방법및 용도 |
| AU2005315319B2 (en) | 2004-12-17 | 2011-07-07 | Glenmark Pharmaceuticals S.A. | Novel heterocyclic compounds useful for the treatment of inflammatory 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 |
| US20100160292A1 (en) | 2006-09-11 | 2010-06-24 | 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 |
| CA2707491A1 (en) | 2007-12-13 | 2009-06-18 | Merck Sharp & Dohme Corp. | Inhibitors of janus kinases |
| PT2247558T (pt) | 2008-02-14 | 2022-03-21 | Lilly Co Eli | Novos agentes de imagiologia para deteção de disfunção neurológica |
| GB0809360D0 (en) | 2008-05-22 | 2008-07-02 | Isis Innovation | Calcium modulation |
| EP2307377A1 (en) | 2008-06-18 | 2011-04-13 | Pfizer Limited | Nicotinamide derivatives |
| CA2986640C (en) | 2008-06-27 | 2019-03-26 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| EP2151441A1 (en) | 2008-08-06 | 2010-02-10 | Julius-Maximilians-Universität Würzburg | Beta-carbolin-derivates as substrates for an enzyme |
| CN102325753B (zh) | 2008-12-19 | 2014-09-10 | 百时美施贵宝公司 | 用作激酶抑制剂的咔唑甲酰胺化合物 |
| 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 |
| ES2733093T3 (es) | 2009-02-13 | 2019-11-27 | Nextivity Inc | Control remoto para amplificador |
| EP2582668B1 (en) | 2010-06-16 | 2016-01-13 | 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 |
| AU2011330850B2 (en) | 2010-11-15 | 2016-01-28 | Viiv Healthcare Uk Limited | Inhibitors of HIV replication |
| PH12013502379A1 (en) | 2011-05-17 | 2014-01-13 | Hoffmann La Roche | Inhibitors of bruton's tyrosine kinase |
| HK1209632A1 (en) | 2012-01-10 | 2016-04-08 | 林伯士艾瑞斯公司 | Irak inhibitors and uses thereof |
| KR20150060839A (ko) | 2012-10-26 | 2015-06-03 | 에프. 호프만-라 로슈 아게 | 브루톤 티로신 키나아제의 억제제 |
| 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 |
| EP3013815B1 (en) * | 2013-06-25 | 2017-05-03 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| HUE050706T2 (hu) | 2014-10-24 | 2020-12-28 | Bristol Myers Squibb Co | Indol karboxamid vegyületek, amelyek hasznosak kináz inhibitorokként |
| ES2800173T3 (es) * | 2014-10-24 | 2020-12-28 | Bristol Myers Squibb Co | Compuestos de atropisómeros tricíclicos |
-
2015
- 2015-10-23 PE PE2017000741A patent/PE20171239A1/es unknown
- 2015-10-23 EA EA201790745A patent/EA032361B1/ru not_active IP Right Cessation
- 2015-10-23 SG SG10201903619YA patent/SG10201903619YA/en unknown
- 2015-10-23 WO PCT/US2015/057077 patent/WO2016065236A1/en not_active Ceased
- 2015-10-23 AR ARP150103455A patent/AR102427A1/es unknown
- 2015-10-23 SM SM20200035T patent/SMT202000035T1/it unknown
- 2015-10-23 EP EP15790408.7A patent/EP3209651B9/en active Active
- 2015-10-23 TN TN2017000158A patent/TN2017000158A1/en unknown
- 2015-10-23 LT LTEP15790408.7T patent/LT3209651T/lt unknown
- 2015-10-23 TW TW104134975A patent/TWI676618B/zh not_active IP Right Cessation
- 2015-10-23 ES ES15790408T patent/ES2761903T3/es active Active
- 2015-10-23 CN CN201580057722.3A patent/CN107074804B/zh active Active
- 2015-10-23 SI SI201530981T patent/SI3209651T1/sl unknown
- 2015-10-23 HR HRP20192197TT patent/HRP20192197T2/hr unknown
- 2015-10-23 DK DK15790408.7T patent/DK3209651T3/da active
- 2015-10-23 KR KR1020177013606A patent/KR102514914B1/ko active Active
- 2015-10-23 SG SG11201703187PA patent/SG11201703187PA/en unknown
- 2015-10-23 MX MX2017005255A patent/MX374724B/es active IP Right Grant
- 2015-10-23 RS RS20191645A patent/RS59707B1/sr unknown
- 2015-10-23 HU HUE15790408A patent/HUE048321T2/hu unknown
- 2015-10-23 PL PL15790408T patent/PL3209651T3/pl unknown
- 2015-10-23 ME MEP-2019-363A patent/ME03754B/me unknown
- 2015-10-23 PT PT157904087T patent/PT3209651T/pt unknown
- 2015-10-23 CA CA2965523A patent/CA2965523A1/en active Pending
- 2015-10-23 PH PH1/2017/500724A patent/PH12017500724B1/en unknown
- 2015-10-23 BR BR112017007545A patent/BR112017007545A2/pt not_active Application Discontinuation
- 2015-10-23 MA MA40302A patent/MA40302B1/fr unknown
- 2015-10-23 MY MYPI2017701432A patent/MY190568A/en unknown
- 2015-10-23 US US15/521,194 patent/US10266491B2/en active Active
- 2015-10-23 JP JP2017522120A patent/JP6599983B2/ja active Active
- 2015-10-23 AU AU2015335703A patent/AU2015335703B2/en not_active Ceased
-
2017
- 2017-04-19 IL IL251798A patent/IL251798B/en active IP Right Grant
- 2017-04-21 CL CL2017001001A patent/CL2017001001A1/es unknown
- 2017-05-04 CO CONC2017/0004517A patent/CO2017004517A2/es unknown
-
2019
- 2019-04-10 US US16/289,878 patent/US10676434B2/en active Active
-
2020
- 2020-01-17 CY CY20201100040T patent/CY1122549T1/el unknown
- 2020-04-27 US US16/859,103 patent/US11053197B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017535536A5 (cg-RX-API-DMAC7.html) | ||
| ME03754B (me) | Derivaтi karbazola | |
| AU2004223827B2 (en) | Heterocyclic compounds and methods of use | |
| ES2310758T3 (es) | Derivados de isoquinolina sustituidos y metodos de uso. | |
| KR101140474B1 (ko) | 간세포 성장 인자 수용체의 억제제로서 유용한 융합된 헤테로시클릭 유도체 및 사용 방법 | |
| CN114948963B (zh) | 蛋白激酶抑制剂苯并内酰胺化合物 | |
| KR101404290B1 (ko) | 과다-증식성 장애 및 맥관형성과 관련된 질환을 치료하는데유용한 치환된 4-아미노-피롤로트리아진 유도체 | |
| EP1802586B1 (en) | Heteroaryl-substituted alkyne compounds and method of use | |
| ES2644873T3 (es) | Derivados de 6-([1,2,4]triazolo[4,3-a]piridin-3-ilmetil)-1,6-naftiridin-5(6H)-ona como inhibidores de c-Met | |
| ES2260277T3 (es) | Compuestos de urea y sus procedimientos de utilizacion. | |
| EP1971604B1 (en) | Pyrrolo-pyridine derivatives for the treatment of cancer diseases | |
| JP2017510576A5 (cg-RX-API-DMAC7.html) | ||
| RU2018123779A (ru) | Новые соединения | |
| JP2013520407A5 (cg-RX-API-DMAC7.html) | ||
| JP2020510092A5 (cg-RX-API-DMAC7.html) | ||
| JP2018507861A5 (cg-RX-API-DMAC7.html) | ||
| JP2016538316A5 (cg-RX-API-DMAC7.html) | ||
| WO2014078813A1 (en) | Compounds and compositions for the treatment of parasitic diseases | |
| JP2005526029A (ja) | 細胞増殖が関与する疾患を治療するためのキノリノン誘導体 | |
| AU2003256481A1 (en) | Substituted anthranilic amide derivatives and methods of use | |
| AU2003252011A1 (en) | Substituted 2-alkylamine nicotinic amide derivatives and use there of | |
| EA025520B1 (ru) | N-(ГЕТЕРО)АРИЛПИРРОЛИДИНОВЫЕ ПРОИЗВОДНЫЕ ПИРАЗОЛ-4-ИЛ-ПИРРОЛО[2,3-d]ПИРИМИДИНОВ И ПИРРОЛ-3-ИЛ-ПИРРОЛО[2,3-d]ПИРИМИДИНОВ В КАЧЕСТВЕ ИНГИБИТОРОВ ЯНУС-КИНАЗЫ | |
| CN104602692A (zh) | 作为激酶抑制剂的氨基喹啉 | |
| JP2018518522A5 (cg-RX-API-DMAC7.html) | ||
| JP2017513887A5 (cg-RX-API-DMAC7.html) |