EA032361B1 - Трициклические соединения - Google Patents
Трициклические соединения Download PDFInfo
- Publication number
- EA032361B1 EA032361B1 EA201790745A EA201790745A EA032361B1 EA 032361 B1 EA032361 B1 EA 032361B1 EA 201790745 A EA201790745 A EA 201790745A EA 201790745 A EA201790745 A EA 201790745A EA 032361 B1 EA032361 B1 EA 032361B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- carbazole
- carboxamide
- fluoro
- tetrahydro
- hydroxypropan
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 399
- 150000003839 salts Chemical class 0.000 claims abstract description 143
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims description 351
- -1 methylpiperazinyl Chemical group 0.000 claims description 333
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 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 description 42
- 238000011282 treatment Methods 0.000 claims description 40
- 229910052698 phosphorus Inorganic materials 0.000 claims description 32
- 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 description 28
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 26
- 239000003814 drug Substances 0.000 claims description 19
- 150000003857 carboxamides Chemical class 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000003937 drug carrier Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000013256 coordination polymer Substances 0.000 claims description 13
- 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 description 10
- 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 description 9
- 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 description 9
- 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 description 9
- 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 description 8
- 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 description 8
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- 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 description 7
- IOHJRHCYUHOIGT-UHFFFAOYSA-N 7-(morpholine-4-carbonyl)-4-(2-prop-2-enoyl-3,4-dihydro-1H-isoquinolin-5-yl)-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(=O)C=C IOHJRHCYUHOIGT-UHFFFAOYSA-N 0.000 claims description 7
- 208000037976 chronic inflammation Diseases 0.000 claims description 7
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- 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 description 6
- ZQMURFSYVNUKJH-FNORWQNLSA-N 4-[3-[[(E)-but-2-enoyl]amino]-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide Chemical compound C(\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 ZQMURFSYVNUKJH-FNORWQNLSA-N 0.000 claims description 6
- FCFAWSXCTCBSBZ-UHFFFAOYSA-N 6-chloro-3-fluoro-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=C(C=C3C1=2)Cl)C(=O)N)F FCFAWSXCTCBSBZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 description 6
- 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 description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 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 description 4
- 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 description 4
- 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 description 4
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Classifications
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- 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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- 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
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- 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
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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
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- 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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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
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- 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
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- 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
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- C07D487/10—Spiro-condensed systems
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462068234P | 2014-10-24 | 2014-10-24 | |
| PCT/US2015/057077 WO2016065236A1 (en) | 2014-10-24 | 2015-10-23 | Carbazole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201790745A1 EA201790745A1 (ru) | 2017-08-31 |
| EA032361B1 true EA032361B1 (ru) | 2019-05-31 |
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| EA201790745A EA032361B1 (ru) | 2014-10-24 | 2015-10-23 | Трициклические соединения |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| PT3210973T (pt) | 2014-10-24 | 2021-02-12 | Takeda Pharmaceuticals Co | Compostos de heteroarilo para o tratamento de doenças oftálmicas |
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