JP2020529433A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020529433A5 JP2020529433A5 JP2020505835A JP2020505835A JP2020529433A5 JP 2020529433 A5 JP2020529433 A5 JP 2020529433A5 JP 2020505835 A JP2020505835 A JP 2020505835A JP 2020505835 A JP2020505835 A JP 2020505835A JP 2020529433 A5 JP2020529433 A5 JP 2020529433A5
- Authority
- JP
- Japan
- Prior art keywords
- isopropyl
- indole
- piperidine
- methyl
- indol
- 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 -C (O) NR x R x Chemical group 0.000 claims 180
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 34
- 125000000217 alkyl group Chemical group 0.000 claims 24
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 13
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 12
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims 6
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- RJSNRCXIBJVKJX-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCC(CC1)C(F)(F)F)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCC(CC1)C(F)(F)F)C1=CN(C)C(=O)C(C)=C1 RJSNRCXIBJVKJX-UHFFFAOYSA-N 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- SBBGZULIWVSWTC-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 SBBGZULIWVSWTC-UHFFFAOYSA-N 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 208000037976 chronic inflammation Diseases 0.000 claims 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 3
- 125000003566 oxetanyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 3
- 125000002873 tetrahydrofuranonyl group Chemical group 0.000 claims 3
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 2
- AQSMJIUDASXMAR-UHFFFAOYSA-N 2-[1-methyl-2-oxo-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridin-3-yl]-N-propylacetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C1)C)=O)CC(=O)NCCC AQSMJIUDASXMAR-UHFFFAOYSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 2
- QBRQIZGNVWNBAA-UHFFFAOYSA-N C(C(C)C)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)C1=CC=CC=C1)C(C)C Chemical compound C(C(C)C)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)C1=CC=CC=C1)C(C)C QBRQIZGNVWNBAA-UHFFFAOYSA-N 0.000 claims 2
- SDSIMFLSAJRWTR-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C=1C=C(C(N(C=1)C)=O)COC Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)C)C=1C=C(C(N(C=1)C)=O)COC SDSIMFLSAJRWTR-UHFFFAOYSA-N 0.000 claims 2
- WSNRYBOPZWSTNW-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=CC=1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=CC=1 WSNRYBOPZWSTNW-UHFFFAOYSA-N 0.000 claims 2
- RSWWYUHUUJDLCR-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 RSWWYUHUUJDLCR-UHFFFAOYSA-N 0.000 claims 2
- LGDZEYQNBLSRGJ-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCOCC1)C=1C=C(C(N(C=1)C)=O)OC Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCOCC1)C=1C=C(C(N(C=1)C)=O)OC LGDZEYQNBLSRGJ-UHFFFAOYSA-N 0.000 claims 2
- OHODETJGDSQAOZ-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C=C(C(N(C=1)C)=O)COC Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C=C(C(N(C=1)C)=O)COC OHODETJGDSQAOZ-UHFFFAOYSA-N 0.000 claims 2
- JTLDUKMCPGRZAX-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C=CC(N(C=1)C)=O Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C=1C=CC(N(C=1)C)=O JTLDUKMCPGRZAX-UHFFFAOYSA-N 0.000 claims 2
- ANGFFYTYKIHXLA-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1CCOCC1)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CC1CCOCC1)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 ANGFFYTYKIHXLA-UHFFFAOYSA-N 0.000 claims 2
- REOSUJNOZBGDRT-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C1=CC=NC=C1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C1=CC=NC=C1 REOSUJNOZBGDRT-UHFFFAOYSA-N 0.000 claims 2
- OUIJYCZIDWGTRY-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C=1C=NC(=CC=1)N1CCOCC1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C=1C=NC(=CC=1)N1CCOCC1 OUIJYCZIDWGTRY-UHFFFAOYSA-N 0.000 claims 2
- CBHLEIOBGMCFSL-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C=1C=NC(=NC=1)OC Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C=1C=NC(=NC=1)OC CBHLEIOBGMCFSL-UHFFFAOYSA-N 0.000 claims 2
- AXVONYGIBFYVGI-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C=1C=NC=CC=1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C=1C=NC=CC=1 AXVONYGIBFYVGI-UHFFFAOYSA-N 0.000 claims 2
- RGQGSOPGTLUBRE-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCOC)C=1C=C(C(N(C=1)C)=O)C=1C=NN(C=1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCOC)C=1C=C(C(N(C=1)C)=O)C=1C=NN(C=1)C RGQGSOPGTLUBRE-UHFFFAOYSA-N 0.000 claims 2
- XSYAPLCABWDSNE-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCS(=O)(=O)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCS(=O)(=O)C)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 XSYAPLCABWDSNE-UHFFFAOYSA-N 0.000 claims 2
- HPNFWPRTPSALED-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C(=C(C(N(N=1)C)=O)C)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C(=C(C(N(N=1)C)=O)C)C HPNFWPRTPSALED-UHFFFAOYSA-N 0.000 claims 2
- SGADBWIWKXIMKT-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C(=CC(N(N=1)C)=O)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C(=CC(N(N=1)C)=O)C SGADBWIWKXIMKT-UHFFFAOYSA-N 0.000 claims 2
- WFRNBQFXLOOCOB-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C=1)C)=O)C1=CC=C(C=C1)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C=1)C)=O)C1=CC=C(C=C1)C WFRNBQFXLOOCOB-UHFFFAOYSA-N 0.000 claims 2
- QWHWYVUWZBJWOP-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C=1)C)=O)C1=CC=CC=C1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C=1)C)=O)C1=CC=CC=C1 QWHWYVUWZBJWOP-UHFFFAOYSA-N 0.000 claims 2
- CHDRJGZAYXAYRA-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C=1)C)=O)C=1C(=NC=CC=1)OC Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C=1)C)=O)C=1C(=NC=CC=1)OC CHDRJGZAYXAYRA-UHFFFAOYSA-N 0.000 claims 2
- FNJCPHWBYIZBMR-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C=1)C)=O)OC Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C=1)C)=O)OC FNJCPHWBYIZBMR-UHFFFAOYSA-N 0.000 claims 2
- PNRHAPUIMZHBDK-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(N=1)C)=O)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(N=1)C)=O)C PNRHAPUIMZHBDK-UHFFFAOYSA-N 0.000 claims 2
- IQZAUIZBDKXPBH-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC(N(C=1)C)=O Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=CC(N(C=1)C)=O IQZAUIZBDKXPBH-UHFFFAOYSA-N 0.000 claims 2
- VDUBWVCWDWCSCZ-UHFFFAOYSA-N C(C)(C)C=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound C(C)(C)C=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O VDUBWVCWDWCSCZ-UHFFFAOYSA-N 0.000 claims 2
- GTYKPPYNNGJJHI-UHFFFAOYSA-N C(C)(C)N1C(C=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)=O Chemical compound C(C)(C)N1C(C=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)=O GTYKPPYNNGJJHI-UHFFFAOYSA-N 0.000 claims 2
- KREPENQKWLPKTL-UHFFFAOYSA-N C(C)C=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound C(C)C=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O KREPENQKWLPKTL-UHFFFAOYSA-N 0.000 claims 2
- ICDCUEPZOOXJDT-UHFFFAOYSA-N C(C)N1N=C(C(=C(C1=O)C)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 Chemical compound C(C)N1N=C(C(=C(C1=O)C)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 ICDCUEPZOOXJDT-UHFFFAOYSA-N 0.000 claims 2
- BEWVLZDZQMRPDD-UHFFFAOYSA-N C(C)N1N=C(C=C(C1=O)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 Chemical compound C(C)N1N=C(C=C(C1=O)C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1 BEWVLZDZQMRPDD-UHFFFAOYSA-N 0.000 claims 2
- ORKYVDRYSILTKJ-UHFFFAOYSA-N C(CC(C)C)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)C1=CC=CC=C1)C(C)C Chemical compound C(CC(C)C)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)C1=CC=CC=C1)C(C)C ORKYVDRYSILTKJ-UHFFFAOYSA-N 0.000 claims 2
- FBYGPAUZQIZKGK-VOTSOKGWSA-N C1(CC1)/C=C/C=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound C1(CC1)/C=C/C=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O FBYGPAUZQIZKGK-VOTSOKGWSA-N 0.000 claims 2
- SHRUUASWFAEHMT-UHFFFAOYSA-N C1(CC1)CCC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound C1(CC1)CCC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O SHRUUASWFAEHMT-UHFFFAOYSA-N 0.000 claims 2
- VFHVSZYXBMRKJO-UHFFFAOYSA-N CC(C)C(O)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C(O)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1 VFHVSZYXBMRKJO-UHFFFAOYSA-N 0.000 claims 2
- WYSNCXMVMSGKEL-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(=O)N(C)C)CC1)C1=CN(C)C(=O)C(=C1)C1=CC=CC=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(=O)N(C)C)CC1)C1=CN(C)C(=O)C(=C1)C1=CC=CC=C1 WYSNCXMVMSGKEL-UHFFFAOYSA-N 0.000 claims 2
- GJZIVZZJRYCCSG-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(=O)N(C)C)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(=O)N(C)C)CC1)C1=CN(C)C(=O)C(C)=C1 GJZIVZZJRYCCSG-UHFFFAOYSA-N 0.000 claims 2
- DPWODRJTDQRDDR-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(=O)N(C)C)CC1)C1=NN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(=O)N(C)C)CC1)C1=NN(C)C(=O)C(C)=C1 DPWODRJTDQRDDR-UHFFFAOYSA-N 0.000 claims 2
- FZMJWJNRKWMMDJ-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(=O)N2CCC(=O)N2)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(=O)N2CCC(=O)N2)CC1)C1=CN(C)C(=O)C(C)=C1 FZMJWJNRKWMMDJ-UHFFFAOYSA-N 0.000 claims 2
- MJTIMBYJKKKJIK-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(C)(C)O)CC1)C1=CN(C)C(=O)C(C)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(C)(C)O)CC1)C1=CN(C)C(=O)C(C)=C1C MJTIMBYJKKKJIK-UHFFFAOYSA-N 0.000 claims 2
- HTAOYTUKGACAMN-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(C)(C)O)CC1)C1=CN(CC2=CC=CC=C2)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(C)(C)O)CC1)C1=CN(CC2=CC=CC=C2)C(=O)C(C)=C1 HTAOYTUKGACAMN-UHFFFAOYSA-N 0.000 claims 2
- FHEJEGCINZHZJJ-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(O)C(C)(C)C)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(O)C(C)(C)C)CC1)C1=CN(C)C(=O)C(C)=C1 FHEJEGCINZHZJJ-UHFFFAOYSA-N 0.000 claims 2
- DZMDPBDZMOFMMM-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C(C)(C)N)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C(C)(C)N)C1=CN(C)C(=O)C(C)=C1 DZMDPBDZMOFMMM-UHFFFAOYSA-N 0.000 claims 2
- YIXODNBDLGLBOY-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C1(N)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C1(N)CC1)C1=CN(C)C(=O)C(C)=C1 YIXODNBDLGLBOY-UHFFFAOYSA-N 0.000 claims 2
- KFEKRZQATNIHHN-HSZRJFAPSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C[C@H]1CCCN1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)C[C@H]1CCCN1)C1=CN(C)C(=O)C(C)=C1 KFEKRZQATNIHHN-HSZRJFAPSA-N 0.000 claims 2
- DKWDUKODESZDRF-QPPBQGQZSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)[C@@H]1C[C@@H](O)CN1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)[C@@H]1C[C@@H](O)CN1)C1=CN(C)C(=O)C(C)=C1 DKWDUKODESZDRF-QPPBQGQZSA-N 0.000 claims 2
- IUUKDKLTUBSIPP-RDGATRHJSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)[C@@H]1C[C@@H](O)CN1C)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)[C@@H]1C[C@@H](O)CN1C)C1=CN(C)C(=O)C(C)=C1 IUUKDKLTUBSIPP-RDGATRHJSA-N 0.000 claims 2
- DKWDUKODESZDRF-XUZZJYLKSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)[C@H]1C[C@H](O)CN1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(=O)[C@H]1C[C@H](O)CN1)C1=CN(C)C(=O)C(C)=C1 DKWDUKODESZDRF-XUZZJYLKSA-N 0.000 claims 2
- XPTIRUUYOOVBKC-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)(C)C(N)=O)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)(C)C(N)=O)C1=CN(C)C(=O)C(C)=C1 XPTIRUUYOOVBKC-UHFFFAOYSA-N 0.000 claims 2
- SMXODWZIORISFH-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCC(CC1)C(C)(C)O)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCC(CC1)C(C)(C)O)C1=CN(C)C(=O)C(C)=C1 SMXODWZIORISFH-UHFFFAOYSA-N 0.000 claims 2
- YLPQCQCOHZVLQT-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCC(F)(F)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCC(F)(F)CC1)C1=CN(C)C(=O)C(C)=C1 YLPQCQCOHZVLQT-UHFFFAOYSA-N 0.000 claims 2
- DEJDDBVJKBVUHN-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(C)C1=O)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCN(C)C1=O)C1=CN(C)C(=O)C(C)=C1 DEJDDBVJKBVUHN-UHFFFAOYSA-N 0.000 claims 2
- TUTKYYXVQSYKII-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCOC1)C1=CN(C)C(=O)C(C)=N1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCOC1)C1=CN(C)C(=O)C(C)=N1 TUTKYYXVQSYKII-UHFFFAOYSA-N 0.000 claims 2
- ZLHBOFFYGQOVSX-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=C(C)N(C)C(=O)C(=C1)C#N Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=C(C)N(C)C(=O)C(=C1)C#N ZLHBOFFYGQOVSX-UHFFFAOYSA-N 0.000 claims 2
- YFJLUXHVORBLRB-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=C(C)N(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=C(C)N(C)C(=O)C(C)=C1 YFJLUXHVORBLRB-UHFFFAOYSA-N 0.000 claims 2
- KIVMKJFHBPRNSL-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CN(C)C(=O)C(C)=C1 KIVMKJFHBPRNSL-UHFFFAOYSA-N 0.000 claims 2
- WKPBDBQZTVGBPO-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CN(C)C(=O)C(C)=N1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CN(C)C(=O)C(C)=N1 WKPBDBQZTVGBPO-UHFFFAOYSA-N 0.000 claims 2
- WEQFIIVECRDCCZ-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1COC1)C1=CN(C)C(=O)C(Cl)=C1C WEQFIIVECRDCCZ-UHFFFAOYSA-N 0.000 claims 2
- JXDCCTHLYDEERE-HSZRJFAPSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)[C@@H]1CCNC1=O)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)[C@@H]1CCNC1=O)C1=CN(C)C(=O)C(C)=C1 JXDCCTHLYDEERE-HSZRJFAPSA-N 0.000 claims 2
- MRSMKJUCZJRDJL-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=C(F)C=CC(OC(F)F)=C2)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=C(F)C=CC(OC(F)F)=C2)CC1)C1=CN(C)C(=O)C(C)=C1 MRSMKJUCZJRDJL-UHFFFAOYSA-N 0.000 claims 2
- XMOXNHQNUABGHE-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=CC=C(OC(F)(F)F)C=C2)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=CC=C(OC(F)(F)F)C=C2)CC1)C1=CN(C)C(=O)C(C)=C1 XMOXNHQNUABGHE-UHFFFAOYSA-N 0.000 claims 2
- RAODKAUDOHGIOY-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=CN(C)N=C2C)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=CN(C)N=C2C)CC1)C1=CN(C)C(=O)C(C)=C1 RAODKAUDOHGIOY-UHFFFAOYSA-N 0.000 claims 2
- NBYCGTLLWPRVTP-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=NC=NN2C)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=NC=NN2C)CC1)C1=CN(C)C(=O)C(C)=C1 NBYCGTLLWPRVTP-UHFFFAOYSA-N 0.000 claims 2
- RKQDVIFQGAUPKA-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=NN(C)C=N2)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2=NN(C)C=N2)CC1)C1=CN(C)C(=O)C(C)=C1 RKQDVIFQGAUPKA-UHFFFAOYSA-N 0.000 claims 2
- JTEGOTPZIRTKTN-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2CC2)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC2CC2)CC1)C1=CN(C)C(=O)C(C)=C1 JTEGOTPZIRTKTN-UHFFFAOYSA-N 0.000 claims 2
- BTWLZKJFNRARRF-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CCC(C(F)(F)F)C(F)(F)F)CC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CCC(C(F)(F)F)C(F)(F)F)CC1)C1=CN(C)C(=O)C(C)=C1 BTWLZKJFNRARRF-UHFFFAOYSA-N 0.000 claims 2
- HIVOYUWZAQKJOI-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CCC(C)(C)O)CC1)C1=CN(C)C(=O)C(C)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CCC(C)(C)O)CC1)C1=CN(C)C(=O)C(C)=C1C HIVOYUWZAQKJOI-UHFFFAOYSA-N 0.000 claims 2
- WTGCZRCSZPHDHB-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C(C)N(C)C(=O)C(=C1)C#N Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=C(C)N(C)C(=O)C(=C1)C#N WTGCZRCSZPHDHB-UHFFFAOYSA-N 0.000 claims 2
- KBLVOIWGLDSCIG-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(=C1)C#N Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(=C1)C#N KBLVOIWGLDSCIG-UHFFFAOYSA-N 0.000 claims 2
- UJYZQNRNPIEBQX-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(=C1)C1=CC=CC(=C1)C#N Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(=C1)C1=CC=CC(=C1)C#N UJYZQNRNPIEBQX-UHFFFAOYSA-N 0.000 claims 2
- MDJOLQJIRPJAEJ-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(C)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(C)=C1C MDJOLQJIRPJAEJ-UHFFFAOYSA-N 0.000 claims 2
- WBWUDRDCOAHSRK-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(C2=CC=CN=C2)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(C2=CC=CN=C2)=C1C WBWUDRDCOAHSRK-UHFFFAOYSA-N 0.000 claims 2
- XWDYTRZBWFUHFC-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(N)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C(N)=C1C XWDYTRZBWFUHFC-UHFFFAOYSA-N 0.000 claims 2
- NIFHQFDMNPVZIY-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(C)C(=O)C=C1C NIFHQFDMNPVZIY-UHFFFAOYSA-N 0.000 claims 2
- BSEJLWNXBAFLCD-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(CC(C)(C)O)C(=O)C=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(CC(C)(C)O)C(=O)C=C1 BSEJLWNXBAFLCD-UHFFFAOYSA-N 0.000 claims 2
- MMSHTFUELICICG-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(CC(F)F)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(CC(F)F)C(=O)C(C)=C1 MMSHTFUELICICG-UHFFFAOYSA-N 0.000 claims 2
- YZIVKSIWNCZCBL-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(CC2=CC=CC=C2)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C1=CN(CC2=CC=CC=C2)C(=O)C(C)=C1 YZIVKSIWNCZCBL-UHFFFAOYSA-N 0.000 claims 2
- SDRXVHVOMGFMNW-UHFFFAOYSA-N CC(C)CCN1CCC(CC1)c1ccc2[nH]c(c(C(C)C)c2c1)-c1cn(C)c(=O)c(Cl)c1C Chemical compound CC(C)CCN1CCC(CC1)c1ccc2[nH]c(c(C(C)C)c2c1)-c1cn(C)c(=O)c(Cl)c1C SDRXVHVOMGFMNW-UHFFFAOYSA-N 0.000 claims 2
- HZDZRDLZMFOIIK-UHFFFAOYSA-N CC(C)CN1C=C(C=C(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCN(CC(=O)N(C)C)CC1 Chemical compound CC(C)CN1C=C(C=C(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCN(CC(=O)N(C)C)CC1 HZDZRDLZMFOIIK-UHFFFAOYSA-N 0.000 claims 2
- CMNUEMGOSNIADQ-UHFFFAOYSA-N CC(C)CN1C=C(C=C(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCNCC1 Chemical compound CC(C)CN1C=C(C=C(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCNCC1 CMNUEMGOSNIADQ-UHFFFAOYSA-N 0.000 claims 2
- JSWHHTXLLDBKSM-UHFFFAOYSA-N CC(C)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1 JSWHHTXLLDBKSM-UHFFFAOYSA-N 0.000 claims 2
- ANJRZJXIENGDDR-UHFFFAOYSA-N CC(C)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound CC(C)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C ANJRZJXIENGDDR-UHFFFAOYSA-N 0.000 claims 2
- KOKSFWQGKUUSHY-UHFFFAOYSA-N CC(C)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(CC(C)C)C(=O)C(C)=C1 Chemical compound CC(C)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(CC(C)C)C(=O)C(C)=C1 KOKSFWQGKUUSHY-UHFFFAOYSA-N 0.000 claims 2
- HJKIXMZZXQOMQS-UHFFFAOYSA-N CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=C(C)N(C)C(=O)C(C)=C1 Chemical compound CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=C(C)N(C)C(=O)C(C)=C1 HJKIXMZZXQOMQS-UHFFFAOYSA-N 0.000 claims 2
- IWIHTKGNAYGUSH-UHFFFAOYSA-N CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC(C)=C(F)N=C1 Chemical compound CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC(C)=C(F)N=C1 IWIHTKGNAYGUSH-UHFFFAOYSA-N 0.000 claims 2
- ZKPVXZRCODLNDA-UHFFFAOYSA-N CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC=CN=C1 Chemical compound CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC=CN=C1 ZKPVXZRCODLNDA-UHFFFAOYSA-N 0.000 claims 2
- SGOGTJBUNWKKDE-UHFFFAOYSA-N CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1C Chemical compound CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1C SGOGTJBUNWKKDE-UHFFFAOYSA-N 0.000 claims 2
- IQROJXLFTNFSIB-UHFFFAOYSA-N CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=N1 Chemical compound CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=N1 IQROJXLFTNFSIB-UHFFFAOYSA-N 0.000 claims 2
- LCDJTNTUCJDMQE-UHFFFAOYSA-N CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C LCDJTNTUCJDMQE-UHFFFAOYSA-N 0.000 claims 2
- ACHGMFQHVQCOBK-UHFFFAOYSA-N CC(C)c1c([nH]c2ccc(cc12)C1CCN(CC1)C(=O)CN(C)C)-c1cc(C#N)c(=O)n(C)c1C Chemical compound CC(C)c1c([nH]c2ccc(cc12)C1CCN(CC1)C(=O)CN(C)C)-c1cc(C#N)c(=O)n(C)c1C ACHGMFQHVQCOBK-UHFFFAOYSA-N 0.000 claims 2
- FAICUBOFCILGFU-UHFFFAOYSA-N CC(C)c1c([nH]c2ccc(cc12)C1CCN(CC1)C(=O)CN(C)C)-c1cc(C)c(=O)n(Cc2ccccc2)c1 Chemical compound CC(C)c1c([nH]c2ccc(cc12)C1CCN(CC1)C(=O)CN(C)C)-c1cc(C)c(=O)n(Cc2ccccc2)c1 FAICUBOFCILGFU-UHFFFAOYSA-N 0.000 claims 2
- XLMOXIUSKTVYNQ-UHFFFAOYSA-N CC(C)c1c([nH]c2ccc(cc12)C1CCN(CC1)C(=O)CN(C)C)-c1cn(C)c(=O)c(C#N)c1C Chemical compound CC(C)c1c([nH]c2ccc(cc12)C1CCN(CC1)C(=O)CN(C)C)-c1cn(C)c(=O)c(C#N)c1C XLMOXIUSKTVYNQ-UHFFFAOYSA-N 0.000 claims 2
- YOPHGOOIQXTRSA-UHFFFAOYSA-N CC(C)c1c([nH]c2ccc(cc12)C1CCNCC1)-c1cc(C)c(=O)n(CCCO)c1 Chemical compound CC(C)c1c([nH]c2ccc(cc12)C1CCNCC1)-c1cc(C)c(=O)n(CCCO)c1 YOPHGOOIQXTRSA-UHFFFAOYSA-N 0.000 claims 2
- SILLCSGOEQCVIF-UHFFFAOYSA-N CC(C)c1c([nH]c2ccc(cc12)C1CCNCC1)-c1ccc(=O)n(C)c1C Chemical compound CC(C)c1c([nH]c2ccc(cc12)C1CCNCC1)-c1ccc(=O)n(C)c1C SILLCSGOEQCVIF-UHFFFAOYSA-N 0.000 claims 2
- WRWJDOLDRUMQCE-UHFFFAOYSA-N CC(CCC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O)(C)C Chemical compound CC(CCC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O)(C)C WRWJDOLDRUMQCE-UHFFFAOYSA-N 0.000 claims 2
- SYCUFKHBAMGLLH-UHFFFAOYSA-N CCC1=CC(C2=C(C(C)C)C3=CC(=CC=C3N2)C2CCNCC2)=C(C)N(C)C1=O Chemical compound CCC1=CC(C2=C(C(C)C)C3=CC(=CC=C3N2)C2CCNCC2)=C(C)N(C)C1=O SYCUFKHBAMGLLH-UHFFFAOYSA-N 0.000 claims 2
- UWHKIGOVDGJNAB-UHFFFAOYSA-N CCCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound CCCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C UWHKIGOVDGJNAB-UHFFFAOYSA-N 0.000 claims 2
- JMZFOQPLNCDFBG-UHFFFAOYSA-N CCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC(C)=CN=C1 Chemical compound CCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC(C)=CN=C1 JMZFOQPLNCDFBG-UHFFFAOYSA-N 0.000 claims 2
- UFQASAXUFMELMV-UHFFFAOYSA-N CCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CN=CN=C1 Chemical compound CCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CN=CN=C1 UFQASAXUFMELMV-UHFFFAOYSA-N 0.000 claims 2
- QDVBHKKAASOSHK-UHFFFAOYSA-N CCN1C(C)=C(C=C(CC)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCNCC1 Chemical compound CCN1C(C)=C(C=C(CC)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCNCC1 QDVBHKKAASOSHK-UHFFFAOYSA-N 0.000 claims 2
- QOSMGUMPKXEYHG-UHFFFAOYSA-N CCN1C=C(C2=C(C(C)C)C3=CC(=CC=C3N2)C2CCN(CC2)C(C)C)C(C)=C(C)C1=O Chemical compound CCN1C=C(C2=C(C(C)C)C3=CC(=CC=C3N2)C2CCN(CC2)C(C)C)C(C)=C(C)C1=O QOSMGUMPKXEYHG-UHFFFAOYSA-N 0.000 claims 2
- CKXFXTPHPHUUJP-UHFFFAOYSA-N CCN1C=C(C2=C(C(C)C)C3=CC(=CC=C3N2)C2CCN(CC2)C2COC2)C(C)=C(C)C1=O Chemical compound CCN1C=C(C2=C(C(C)C)C3=CC(=CC=C3N2)C2CCN(CC2)C2COC2)C(C)=C(C)C1=O CKXFXTPHPHUUJP-UHFFFAOYSA-N 0.000 claims 2
- DXXJCNPLMRMBOB-UHFFFAOYSA-N CCN1C=C(C=C(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCNCC1 Chemical compound CCN1C=C(C=C(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCNCC1 DXXJCNPLMRMBOB-UHFFFAOYSA-N 0.000 claims 2
- FKHYXXHDDLSTGS-UHFFFAOYSA-N CCNC(=O)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound CCNC(=O)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C FKHYXXHDDLSTGS-UHFFFAOYSA-N 0.000 claims 2
- YPKLTJNUODTQSB-UHFFFAOYSA-N CCc1cc(cn(CC)c1=O)-c1[nH]c2ccc(cc2c1C(C)C)C1CCNCC1 Chemical compound CCc1cc(cn(CC)c1=O)-c1[nH]c2ccc(cc2c1C(C)C)C1CCNCC1 YPKLTJNUODTQSB-UHFFFAOYSA-N 0.000 claims 2
- NDRWBFPBYSWTHC-UHFFFAOYSA-N CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)COC)C(C)C)C Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)COC)C(C)C)C NDRWBFPBYSWTHC-UHFFFAOYSA-N 0.000 claims 2
- LKXPZIAWZSXNIJ-UHFFFAOYSA-N CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)OC)C(C)C)C Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)OC)C(C)C)C LKXPZIAWZSXNIJ-UHFFFAOYSA-N 0.000 claims 2
- CIUJKGGOIQRVQE-UHFFFAOYSA-N CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)CCOC)=O)C)C(C)C)C Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)CCOC)=O)C)C(C)C)C CIUJKGGOIQRVQE-UHFFFAOYSA-N 0.000 claims 2
- QLUYHMAIZBGBAW-UHFFFAOYSA-N CNC(=O)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=C(C)N(C)C(=O)C(=C1)C#N Chemical compound CNC(=O)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=C(C)N(C)C(=O)C(=C1)C#N QLUYHMAIZBGBAW-UHFFFAOYSA-N 0.000 claims 2
- YFAHLMCTUWAOMN-UHFFFAOYSA-N CNC(=O)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1C Chemical compound CNC(=O)CN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1C YFAHLMCTUWAOMN-UHFFFAOYSA-N 0.000 claims 2
- LUBMNCIZVJZWTI-UHFFFAOYSA-N CNC(C)(C)C(=O)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CNC(C)(C)C(=O)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1 LUBMNCIZVJZWTI-UHFFFAOYSA-N 0.000 claims 2
- LBWVZINQDMMCRV-UHFFFAOYSA-N COC(=O)C1=CC(=CN(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCNCC1 Chemical compound COC(=O)C1=CC(=CN(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCNCC1 LBWVZINQDMMCRV-UHFFFAOYSA-N 0.000 claims 2
- LRYGGBYVMWJIAW-UHFFFAOYSA-N COC1=CC(C2=C(C(C)C)C3=CC(=CC=C3N2)C2CCN(CC2)C2COC2)=C(C)N(C)C1=O Chemical compound COC1=CC(C2=C(C(C)C)C3=CC(=CC=C3N2)C2CCN(CC2)C2COC2)=C(C)N(C)C1=O LRYGGBYVMWJIAW-UHFFFAOYSA-N 0.000 claims 2
- FYGUWGGYJLBXEH-UHFFFAOYSA-N COCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC=C(C)N=C1 Chemical compound COCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC=C(C)N=C1 FYGUWGGYJLBXEH-UHFFFAOYSA-N 0.000 claims 2
- UCLNYKOCVNUPSI-UHFFFAOYSA-N COCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound COCCN1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(Cl)=C1C UCLNYKOCVNUPSI-UHFFFAOYSA-N 0.000 claims 2
- QENPVZKZFVPCLZ-UHFFFAOYSA-N COCCn1cc(cc(C)c1=O)-c1[nH]c2ccc(cc2c1C(C)C)C1CCN(CC(=O)N(C)C)CC1 Chemical compound COCCn1cc(cc(C)c1=O)-c1[nH]c2ccc(cc2c1C(C)C)C1CCN(CC(=O)N(C)C)CC1 QENPVZKZFVPCLZ-UHFFFAOYSA-N 0.000 claims 2
- GFCUPHKSCWWTML-UHFFFAOYSA-N COc1cc(-c2[nH]c3ccc(cc3c2C(C)C)C2CCN(CC2)C(=O)CN(C)C)c(C)n(C)c1=O Chemical compound COc1cc(-c2[nH]c3ccc(cc3c2C(C)C)C2CCN(CC2)C(=O)CN(C)C)c(C)n(C)c1=O GFCUPHKSCWWTML-UHFFFAOYSA-N 0.000 claims 2
- ZKNIVOLTHVFFCU-UHFFFAOYSA-N ClC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound ClC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O ZKNIVOLTHVFFCU-UHFFFAOYSA-N 0.000 claims 2
- YZQLLHSSQSYSFP-UHFFFAOYSA-N FC1=C2C(=C(NC2=CC=C1C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1)C(C)C Chemical compound FC1=C2C(=C(NC2=CC=C1C1CCN(CC1)CCC)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1)C(C)C YZQLLHSSQSYSFP-UHFFFAOYSA-N 0.000 claims 2
- HTOVANYLMPNSSH-UHFFFAOYSA-N FC1=CC=C(C=N1)C=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(C)C)C)=O Chemical compound FC1=CC=C(C=N1)C=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCN(CC1)C(C)C)C)=O HTOVANYLMPNSSH-UHFFFAOYSA-N 0.000 claims 2
- NGRMYPOSYPOHKW-UHFFFAOYSA-N FC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound FC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O NGRMYPOSYPOHKW-UHFFFAOYSA-N 0.000 claims 2
- HJFRYUBEDSOGKV-UHFFFAOYSA-N N,N-dimethyl-2-[1-methyl-2-oxo-5-(5-piperidin-4-yl-3-propan-2-yl-1H-indol-2-yl)pyridin-3-yl]acetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCNCC1)C=1C=C(C(N(C1)C)=O)CC(=O)N(C)C HJFRYUBEDSOGKV-UHFFFAOYSA-N 0.000 claims 2
- SMLCMZPZOLSWDC-UHFFFAOYSA-N NC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound NC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O SMLCMZPZOLSWDC-UHFFFAOYSA-N 0.000 claims 2
- SXBPOSARLBEZCR-UHFFFAOYSA-N OC(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)CC(C)C)=O)C)C(C)C)(C)C Chemical compound OC(CN1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)CC(C)C)=O)C)C(C)C)(C)C SXBPOSARLBEZCR-UHFFFAOYSA-N 0.000 claims 2
- PIYTTYGQOKZIDI-UHFFFAOYSA-N OCC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound OCC=1C(N(C=C(C=1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O PIYTTYGQOKZIDI-UHFFFAOYSA-N 0.000 claims 2
- MTFHOZSZQAEDMI-UHFFFAOYSA-N OCCN1C(C(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O Chemical compound OCCN1C(C(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCNCC1)C)=O MTFHOZSZQAEDMI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- NXQOUXZNQJEEIJ-UHFFFAOYSA-N 1,4-dimethyl-2-oxopyridine-3-carbonitrile Chemical compound CC=1C=CN(C)C(=O)C=1C#N NXQOUXZNQJEEIJ-UHFFFAOYSA-N 0.000 claims 1
- GZHMVYGTUDWGOJ-UHFFFAOYSA-N 1-(4,4,4-trifluorobutyl)piperidine Chemical compound FC(F)(F)CCCN1CCCCC1 GZHMVYGTUDWGOJ-UHFFFAOYSA-N 0.000 claims 1
- SAPDHAIDOPKGHW-UHFFFAOYSA-N 1-(oxan-4-yl)piperidine Chemical compound C1CCCCN1C1CCOCC1 SAPDHAIDOPKGHW-UHFFFAOYSA-N 0.000 claims 1
- NFYZJKOJCRMDRO-UHFFFAOYSA-N 1-(oxetan-3-yl)piperidine Chemical compound C1OCC1N1CCCCC1 NFYZJKOJCRMDRO-UHFFFAOYSA-N 0.000 claims 1
- VTDIWMPYBAVEDY-UHFFFAOYSA-N 1-propylpiperidine Chemical compound CCCN1CCCCC1 VTDIWMPYBAVEDY-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- DMORLWUYAVTAPC-UHFFFAOYSA-N 2-(dimethylamino)-1-piperidin-1-ylethanone Chemical compound CN(C)CC(=O)N1CCCCC1 DMORLWUYAVTAPC-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- SSBJNXYJAHFKJQ-UHFFFAOYSA-N 2-methyl-1-piperidin-1-ylpropan-2-ol Chemical compound CC(C)(O)CN1CCCCC1 SSBJNXYJAHFKJQ-UHFFFAOYSA-N 0.000 claims 1
- LNJMHEJAYSYZKK-UHFFFAOYSA-N 2-methylpyrimidine Chemical compound CC1=NC=CC=N1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 claims 1
- HLACCWZATOVISE-UHFFFAOYSA-N 2-propan-2-yl-1H-pyridazine Chemical compound CC(C)N1NC=CC=C1 HLACCWZATOVISE-UHFFFAOYSA-N 0.000 claims 1
- GJELDSCPTNJBFL-UHFFFAOYSA-N 3-chloro-1,4-dimethylpyridin-2-one Chemical compound Cc1ccn(C)c(=O)c1Cl GJELDSCPTNJBFL-UHFFFAOYSA-N 0.000 claims 1
- OFDVABAUFQJWEZ-UHFFFAOYSA-N 3-pyridin-3-ylpyridine Chemical compound C1=CN=CC(C=2C=NC=CC=2)=C1 OFDVABAUFQJWEZ-UHFFFAOYSA-N 0.000 claims 1
- ZTMXVCKXKBNQCY-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCOC)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)CCOC)C=1C=C(C(N(C=1)C)=O)C=1C=NC=NC=1 ZTMXVCKXKBNQCY-UHFFFAOYSA-N 0.000 claims 1
- ZEAPVYLDYDNKKL-UHFFFAOYSA-N CC(C)C1=C(C(C=C2C#N)=C(C)N(C)C2=O)NC2=CC=CC=C12 Chemical compound CC(C)C1=C(C(C=C2C#N)=C(C)N(C)C2=O)NC2=CC=CC=C12 ZEAPVYLDYDNKKL-UHFFFAOYSA-N 0.000 claims 1
- VFILASBCHHSZNH-UHFFFAOYSA-N CC(C)C1=C(C(C=C2C)=CN(CC3=CC=CC=C3)C2=O)NC2=CC=CC=C12 Chemical compound CC(C)C1=C(C(C=C2C)=CN(CC3=CC=CC=C3)C2=O)NC2=CC=CC=C12 VFILASBCHHSZNH-UHFFFAOYSA-N 0.000 claims 1
- MBHRCJNMILRMEJ-UHFFFAOYSA-N CC(C)C1=C(C(C=C2OC)=CN(C)C2=O)NC2=CC=CC=C12 Chemical compound CC(C)C1=C(C(C=C2OC)=CN(C)C2=O)NC2=CC=CC=C12 MBHRCJNMILRMEJ-UHFFFAOYSA-N 0.000 claims 1
- BJTVBNMOQDYPII-UHFFFAOYSA-N CC(C)C1=C(C2=CN(C)NC(C)=C2)NC2=CC=C(C3CCNCC3)C=C12 Chemical compound CC(C)C1=C(C2=CN(C)NC(C)=C2)NC2=CC=C(C3CCNCC3)C=C12 BJTVBNMOQDYPII-UHFFFAOYSA-N 0.000 claims 1
- DFSHOADIORZBHR-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(C)CC1)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(C)CC1)C1=CN(C)C(=O)C(Cl)=C1C DFSHOADIORZBHR-UHFFFAOYSA-N 0.000 claims 1
- QEGADFWJXCOAFR-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(C)(C)O)CC1)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC(C)(C)O)CC1)C1=CN(C)C(=O)C(Cl)=C1C QEGADFWJXCOAFR-UHFFFAOYSA-N 0.000 claims 1
- NPUOUPYXRZWHKH-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)=O)C1=CN(C)C(=O)C(Cl)=C1C Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C(C)=O)C1=CN(C)C(=O)C(Cl)=C1C NPUOUPYXRZWHKH-UHFFFAOYSA-N 0.000 claims 1
- FKDNBPCBKXEFMR-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCCCC1)C1=CN(C)C(=O)C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCN(CC1)C1CCCCC1)C1=CN(C)C(=O)C(C)=C1 FKDNBPCBKXEFMR-UHFFFAOYSA-N 0.000 claims 1
- DGXPAHSQMQWTCS-UHFFFAOYSA-N CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC=CN=C1C Chemical compound CC(C)N1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(=C1)C1=CC=CN=C1C DGXPAHSQMQWTCS-UHFFFAOYSA-N 0.000 claims 1
- MEWAYOUFYMZAIL-UHFFFAOYSA-N CN1C=C(C=C(C1=O)C)C=1NC2=CC=CC=C2C1C(C)C Chemical compound CN1C=C(C=C(C1=O)C)C=1NC2=CC=CC=C2C1C(C)C MEWAYOUFYMZAIL-UHFFFAOYSA-N 0.000 claims 1
- GPSGVZGEMXSGGQ-UHFFFAOYSA-N COC1=C(C)C(=CN(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCN(CC1)C1COC1 Chemical compound COC1=C(C)C(=CN(C)C1=O)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCN(CC1)C1COC1 GPSGVZGEMXSGGQ-UHFFFAOYSA-N 0.000 claims 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005959 diazepanyl group Chemical group 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- DWYJHMSKXMHOAP-UHFFFAOYSA-N oxetan-2-ol Chemical compound OC1CCO1 DWYJHMSKXMHOAP-UHFFFAOYSA-N 0.000 claims 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762541335P | 2017-08-04 | 2017-08-04 | |
| US62/541,335 | 2017-08-04 | ||
| PCT/US2018/045082 WO2019028302A1 (en) | 2017-08-04 | 2018-08-03 | SUBSTITUTED INDOLE COMPOUNDS USEFUL AS TLR7 / 8/9 INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020529433A JP2020529433A (ja) | 2020-10-08 |
| JP2020529433A5 true JP2020529433A5 (enExample) | 2021-09-09 |
| JP7104775B2 JP7104775B2 (ja) | 2022-07-21 |
Family
ID=63245105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020505835A Active JP7104775B2 (ja) | 2017-08-04 | 2018-08-03 | Ｔｌｒ７／８／９の阻害剤として有用な置換インドール化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US11447466B2 (enExample) |
| EP (1) | EP3661926B1 (enExample) |
| JP (1) | JP7104775B2 (enExample) |
| KR (1) | KR102651947B1 (enExample) |
| CN (1) | CN110997656B (enExample) |
| ES (1) | ES2909401T3 (enExample) |
| WO (1) | WO2019028302A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| US11878975B2 (en) | 2017-12-19 | 2024-01-23 | Bristol-Myers Squibb Company | Substituted indole compounds useful as TLR inhibitors |
| EP3752505B1 (en) | 2018-02-12 | 2023-01-11 | F. Hoffmann-La Roche AG | Novel sulfone compounds and derivatives for the treatment and prophylaxis of virus infection |
| WO2019233941A1 (en) | 2018-06-05 | 2019-12-12 | F. Hoffmann-La Roche Ag | Tetrahydro-1 h-pyrazino[2,1 -ajisoindolylquinoline compounds for the treatment of autoimmune disease |
| US11713327B2 (en) | 2018-06-12 | 2023-08-01 | Hoffmann-La Roche Inc. | Heteroaryl heterocyclyl compounds for the treatment of autoimmune disease |
| JP7366994B2 (ja) | 2018-07-23 | 2023-10-23 | エフ． ホフマン－ラ ロシュ アーゲー | 自己免疫疾患治療用の新規ピペラジン化合物 |
| JP7233809B2 (ja) | 2018-09-04 | 2023-03-07 | エフ． ホフマン－ラ ロシュ アーゲー | 自己免疫疾患の処置のためのベンゾチアゾール化合物 |
| US12252484B2 (en) | 2018-09-06 | 2025-03-18 | Hoffmann-La Roche Inc. | Pyrazolopyridine compounds for the treatment of autoimmune disease |
| WO2020048595A1 (en) | 2018-09-06 | 2020-03-12 | F. Hoffmann-La Roche Ag | Novel cyclic amidine compounds for the treatment of autoimmune disease |
| EP4051387B1 (en) | 2019-10-31 | 2025-02-19 | F. Hoffmann-La Roche AG | Hydropyrazino[1,2-d][1,4]diazepine compounds for the treatment of autoimmune disease |
| US12486273B2 (en) | 2019-11-19 | 2025-12-02 | Hoffmann-La Roche Inc. | Hydro-1H-pyrrolo[1,2-a]pyrazine compounds for the treatment of autoimmune disease |
| CN114728988B (zh) | 2019-11-20 | 2024-12-10 | 豪夫迈·罗氏有限公司 | 用于治疗自身免疫性疾病的螺(异苯并呋喃氮杂环丁烷)化合物 |
| CN111747926B (zh) * | 2020-06-23 | 2024-01-30 | 浙江华海药业股份有限公司 | 一种羟哌吡酮游离碱的合成工艺改进方法 |
| US12486267B2 (en) | 2020-08-19 | 2025-12-02 | Bristol-Myers Squibb Company | Imidazo[1,2-A]pyridine and [1,2,4]triazolo[1,5-A]pyridine derivatives as TLR9 inhibitors for the treatment of fibrosis |
| KR20230053645A (ko) | 2020-08-19 | 2023-04-21 | 브리스톨-마이어스 스큅 컴퍼니 | 섬유증의 치료를 위한 tlr9 억제제로서의 1h-벤조[d]이미다졸 유도체 |
| AU2021328577A1 (en) | 2020-08-19 | 2023-03-23 | Bristol-Myers Squibb Company | 1H-pyrrolo[3,2-c]pyridine and 1H-pyrrolo[2,3-c]pyridine derivatives as TLR9 inhibitors for the treatment of fibrosis |
| CN112430632B (zh) * | 2020-11-18 | 2022-09-13 | 上海合全药物研发有限公司 | 2-((反式)-4-氨基环己烷基)异丙醇的制备方法 |
| TWI861488B (zh) | 2021-04-16 | 2024-11-11 | 美商基利科學股份有限公司 | 噻吩并吡咯化合物 |
| CN113604553B (zh) * | 2021-07-27 | 2023-08-15 | 中南大学湘雅二医院 | 成人still’s病生物标志物、诊断试剂及其应用 |
| US12070455B2 (en) | 2021-09-10 | 2024-08-27 | Gilead Sciences, Inc. | Thienopyrrole compounds |
| CN114591339B (zh) * | 2022-05-10 | 2022-08-02 | 上海维申医药有限公司 | 一类Toll样受体抑制剂及其制备和应用 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EE200100323A (et) | 1998-12-18 | 2002-08-15 | Axys Pharmaceuticals, Inc. | (Hetero)arüüli - bitsüklilise heteroarüüli derivaadid, nende valmistamine ja nende kasutamine proteaasiinhibiitoritena |
| JP2007524615A (ja) | 2003-06-20 | 2007-08-30 | コーリー ファーマシューティカル ゲーエムベーハー | 低分子トール様レセプター（ｔｌｒ）アンタゴニスト |
| US20060235037A1 (en) * | 2005-04-15 | 2006-10-19 | Purandare Ashok V | Heterocyclic inhibitors of protein arginine methyl transferases |
| JP2009532501A (ja) | 2006-04-04 | 2009-09-10 | ミリアド ジェネティクス， インコーポレイテッド | 疾患および障害のための化合物 |
| DE102006033109A1 (de) | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| US8027888B2 (en) | 2006-08-31 | 2011-09-27 | Experian Interactive Innovation Center, Llc | Online credit card prescreen systems and methods |
| ATE495743T1 (de) | 2006-12-01 | 2011-02-15 | Galapagos Nv | Triazolopyridinverbindungen zur behandlung von degenerations- und entzündungskrankheiten |
| WO2008152471A1 (en) | 2007-06-12 | 2008-12-18 | Coley Pharmaceutical Group, Inc. | Quinazoline derivative useful as toll-like receptor antagonist |
| WO2009030996A1 (en) | 2007-09-05 | 2009-03-12 | Coley Pharmaceutical Group, Inc. | Triazole compounds as toll-like receptor (tlr) agonists |
| FR2926556B1 (fr) | 2008-01-22 | 2010-02-19 | Sanofi Aventis | Derives de carboxamides n-azabicycliques, leur preparation et leur application en therapeutique |
| EP2350032B1 (en) | 2008-09-26 | 2016-05-25 | Eisai R&D Management Co., Ltd. | Benzoxazole compounds and methods of use |
| US8785489B2 (en) | 2008-10-17 | 2014-07-22 | Boehringer Ingelheim International Gmbh | Heteroaryl substituted indole compounds useful as MMP-13 inhibitors |
| TWI462920B (zh) | 2009-06-26 | 2014-12-01 | 葛萊伯格有限公司 | 用於治療退化性及發炎疾病之新穎化合物 |
| TR201809739T4 (tr) | 2009-07-16 | 2018-07-23 | Mallinckrodt Llc | Toll benzeri reseptör 9 antagonistleri olarak (+)-morfinanlar ve bunların terapötik amaçlı kullanımları. |
| US9241991B2 (en) | 2010-10-21 | 2016-01-26 | The Brigham And Women's Hospital, Inc. | Agents, compositions, and methods for treating pruritus and related skin conditions |
| CA2824779C (en) | 2011-01-12 | 2020-01-14 | Array Biopharma, Inc. | Substituted benzoazepines as toll-like receptor modulators |
| ES2620605T3 (es) | 2011-01-12 | 2017-06-29 | Ventirx Pharmaceuticals, Inc. | Benzoazepinas sustituidas como moduladores de receptores tipo Toll |
| WO2012167053A1 (en) | 2011-06-01 | 2012-12-06 | Janus Biotherapeutics, Inc. | Novel immune system modulators |
| RU2606114C2 (ru) | 2011-06-01 | 2017-01-10 | Джейнус Байотерапьютикс, Инк. | Новые модуляторы иммунной системы |
| AU2012267556B9 (en) | 2011-06-09 | 2017-05-11 | Rhizen Pharmaceuticals Sa | Novel compounds as modulators of GPR-119 |
| ES2555167T3 (es) | 2011-07-15 | 2015-12-29 | Janssen Pharmaceuticals, Inc. | Nuevos derivados de indol sustituidos como moduladores de gamma secretasa |
| CA2850932A1 (en) | 2011-10-04 | 2013-04-11 | Janus Biotherapeutics, Inc. | Novel imidazole quinoline-based immune system modulators |
| EP2850067B1 (en) | 2012-05-18 | 2017-08-16 | Sumitomo Dainippon Pharma Co., Ltd. | Carboxylic acid compounds |
| JO3407B1 (ar) | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| US20150051208A1 (en) | 2013-08-14 | 2015-02-19 | Boehringer Ingelheim International Gmbh | Pyridinones |
| TWI624467B (zh) | 2013-10-14 | 2018-05-21 | 衛材Ｒ＆Ｄ企管股份有限公司 | 選擇性經取代之喹啉化合物 |
| CA2933466A1 (en) | 2013-12-13 | 2015-06-18 | Takeda Pharmaceutical Company Limited | Pyrrolo[3,2-c]pyridine derivatives as tlr inhibitors |
| WO2016029077A1 (en) | 2014-08-22 | 2016-02-25 | Janus Biotherapeutics, Inc. | Novel n2, n4, n7, 6-tetrasubstituted pteridine-2,4,7-triamine and 2, 4, 6, 7-tetrasubstituted pteridine compounds and methods of synthesis and use thereof |
| US9550778B2 (en) | 2014-10-03 | 2017-01-24 | Vanderbilt University | Substituted 6-aryl-imidazopyridine and 6-aryl-triazolopyridine carboxamide analogs as negative allosteric modulators of mGluR5 |
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| MX391344B (es) | 2016-07-30 | 2025-03-21 | Bristol Myers Squibb Co | Compuestos indol sustituidos con dimetoxifenilo como inhibidores de receptores tipo toll 7, 8 o 9 (tlr7, tlr8 o tlr9). |
| JP7028861B2 (ja) * | 2016-09-09 | 2022-03-02 | ブリストル－マイヤーズ スクイブ カンパニー | ピリジル置換のインドール化合物 |
| KR102730859B1 (ko) * | 2017-12-20 | 2024-11-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 및 헤테로아릴 치환된 인돌 화합물 |
-
2018
- 2018-08-03 CN CN201880050864.0A patent/CN110997656B/zh active Active
- 2018-08-03 EP EP18756116.2A patent/EP3661926B1/en active Active
- 2018-08-03 KR KR1020207005967A patent/KR102651947B1/ko active Active
- 2018-08-03 US US16/635,593 patent/US11447466B2/en active Active
- 2018-08-03 JP JP2020505835A patent/JP7104775B2/ja active Active
- 2018-08-03 ES ES18756116T patent/ES2909401T3/es active Active
- 2018-08-03 WO PCT/US2018/045082 patent/WO2019028302A1/en not_active Ceased
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019525941A5 (enExample) | ||
| JP2019530667A5 (enExample) | ||
| TWI538907B (zh) | 非核苷反轉錄酶抑制劑 | |
| KR102651947B1 (ko) | Tlr7/8/9의 억제제로서 유용한 치환된 인돌 화합물 | |
| JP2022531801A5 (enExample) | ||
| KR101841003B1 (ko) | 신규한 소염제 | |
| ES2360741T3 (es) | Triazolil fenil bencenosulfonamidas. | |
| JP6298115B2 (ja) | Ｌｒｒｋ２調節薬としてのピラゾールアミノピリミジン誘導体 | |
| JP2024521618A5 (enExample) | ||
| RU2581504C2 (ru) | Производные триазола и их применение при неврологических заболеваниях | |
| JP2019530667A (ja) | ピリジル置換のインドール化合物 | |
| JP2023503052A5 (enExample) | ||
| HRP20160359T1 (hr) | Derivati kinazolindiona, njihovo dobivanje i njihove terapijske primjene | |
| JP2021506816A5 (enExample) | ||
| CA2476012A1 (en) | Substituted pyridinones as modulators of p38 map kinase | |
| CA2642922A1 (en) | Melanocortin type 4 receptor agonist piperidinoylpyrrolidines | |
| JP2019519484A5 (enExample) | ||
| RU2016141088A (ru) | 5-замещённые индазол-3-карбоксамиды и их получение и применение | |
| RU2006117326A (ru) | Амидные производные | |
| JP2009524589A5 (ja) | 置換されたイソキノリン−１，３（２ｈ，４ｈ）−ジオン、１−チオキソ−１，４−ジヒドロ−２ｈ−イソキノリン−３−オン、および１，４−ジヒドロ−３（２ｈ）−イソキノロン、ならびにキナーゼインヒビターとしてのそれらの使用 | |
| HRP20120457T1 (hr) | 4-(4-cijano-2-tioaril)dihidropirimidinoni i njihova uporaba | |
| JP2016523911A5 (enExample) | ||
| JP2006512412A5 (ja) | 神経系の疾患の治療用のベンズアゼピン誘導体 | |
| JP2012515761A5 (enExample) | ||
| KR20130038420A (ko) | 브루톤 티로신 키나아제의 억제제 |