JPWO2020163647A5 - - Google Patents
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- JPWO2020163647A5 JPWO2020163647A5 JP2021546237A JP2021546237A JPWO2020163647A5 JP WO2020163647 A5 JPWO2020163647 A5 JP WO2020163647A5 JP 2021546237 A JP2021546237 A JP 2021546237A JP 2021546237 A JP2021546237 A JP 2021546237A JP WO2020163647 A5 JPWO2020163647 A5 JP WO2020163647A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- pharmaceutically acceptable
- fluoro
- oxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 89
- 239000012453 solvate Substances 0.000 claims description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 77
- 150000002431 hydrogen Chemical group 0.000 claims description 64
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 57
- 229910052805 deuterium Inorganic materials 0.000 claims description 57
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- -1 2-hydroxy-phenyl Chemical group 0.000 claims description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 8
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 8
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 7
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 7
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 12
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- UCDFOTQJWLSOJR-WYGDDPHOSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(2-methyl-1,3-thiazol-4-yl)phenol Chemical compound CC1=NC(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)=CS1 UCDFOTQJWLSOJR-WYGDDPHOSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- HNEXFBUVJLQNKX-GDUHTRTMSA-N 2-[6-[[(1R,2R,3R,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound CN1N=CC(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)=C1 HNEXFBUVJLQNKX-GDUHTRTMSA-N 0.000 description 1
- FURQXUBOEDUTGE-XXTHSBEZSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound C[C@](CC1)(C[C@@H]2OC3=CC=C(C(C=CC(C4=CN(C)N=C4)=C4)=C4O)N=N3)N[C@@]1(C)[C@H]2F FURQXUBOEDUTGE-XXTHSBEZSA-N 0.000 description 1
- URBXUFAMOPFYSR-JKLQHZFJSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C[C@](CC1)(C[C@@H]2OC3=CC=C(C(C=CC(C4=CNN=C4)=C4)=C4O)N=N3)N[C@@]1(C)[C@H]2F URBXUFAMOPFYSR-JKLQHZFJSA-N 0.000 description 1
- GBIWFFQXJBZLAZ-ZNEWLNCYSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-(6-methoxypyridazin-4-yl)phenol Chemical compound C[C@](CC1)(C[C@@H]2OC3=CC=C(C(C=CC(C4=CN=NC(OC)=C4)=C4)=C4O)N=N3)N[C@@]1(C)[C@H]2F GBIWFFQXJBZLAZ-ZNEWLNCYSA-N 0.000 description 1
- AURZSSRIDIEPIC-JKLQHZFJSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-pyrazol-1-ylphenol Chemical compound C[C@](CC1)(C[C@@H]2OC3=CC=C(C(C=CC(N4N=CC=C4)=C4)=C4O)N=N3)N[C@@]1(C)[C@H]2F AURZSSRIDIEPIC-JKLQHZFJSA-N 0.000 description 1
- GGCJWBRBBZITKO-TWDDROGUSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound F[C@@H]1[C@]2(CCC[C@@](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C=1C=NN(C=1)C)O)(N2)C)C GGCJWBRBBZITKO-TWDDROGUSA-N 0.000 description 1
- REVWNFGCHNYIIR-XXTHSBEZSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound C[C@](CCC1)(C[C@@H]2OC3=CC=C(C(C=CC(C4=CNN=C4)=C4)=C4O)N=N3)N[C@@]1(C)[C@H]2F REVWNFGCHNYIIR-XXTHSBEZSA-N 0.000 description 1
- AMUQOTQDFBTQBB-LSJNVOPQSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-(1,3,4-oxadiazol-2-yl)phenol Chemical compound F[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C=1OC=NN=1)O)N2 AMUQOTQDFBTQBB-LSJNVOPQSA-N 0.000 description 1
- UTUBNVQAVMGTFE-LSJNVOPQSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-(1,3,4-thiadiazol-2-yl)phenol Chemical compound F[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C=1SC=NN=1)O)N2 UTUBNVQAVMGTFE-LSJNVOPQSA-N 0.000 description 1
- RYEPYHZXUPUQOV-PJTPKWCPSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound CN1N=CC(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CC2)[C@@H]3F)=C1 RYEPYHZXUPUQOV-PJTPKWCPSA-N 0.000 description 1
- LCAWDCIOURKPOA-DKQPGVRISA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound F[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C=1C=NNC=1)O)N2 LCAWDCIOURKPOA-DKQPGVRISA-N 0.000 description 1
- UGZMPYKMNGLLEQ-YWNZRQFQSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-indazol-1-ylphenol Chemical compound F[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)N1N=CC3=CC=CC=C13)O)N2 UGZMPYKMNGLLEQ-YWNZRQFQSA-N 0.000 description 1
- LGHFJAFKPCMUJU-GPZWCRHOSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-8-azabicyclo[3.2.1]octan-3-yl]oxy]pyridazin-3-yl]-5-pyrazol-1-ylphenol Chemical compound F[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)N1N=CC=C1)O)N2 LGHFJAFKPCMUJU-GPZWCRHOSA-N 0.000 description 1
- HVJYBCCYVAGVMD-MJFFMMMISA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1,3,4-oxadiazol-2-yl)phenol Chemical compound F[C@@H]1[C@H]2CCC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C=1OC=NN=1)O)N2 HVJYBCCYVAGVMD-MJFFMMMISA-N 0.000 description 1
- RFDKOGGOAFUSGZ-MJFFMMMISA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1,3,4-thiadiazol-2-yl)phenol Chemical compound F[C@@H]1[C@H]2CCC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C=1SC=NN=1)O)N2 RFDKOGGOAFUSGZ-MJFFMMMISA-N 0.000 description 1
- CLFNSLXJXSGEGN-FAFONEJGSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1-methylpyrazol-3-yl)phenol Chemical compound CN(C=C1)N=C1C(C=C1)=CC(O)=C1C(N=N1)=CC=C1O[C@@H](C[C@H]1N[C@@H]2CCC1)[C@@H]2F CLFNSLXJXSGEGN-FAFONEJGSA-N 0.000 description 1
- HNEXFBUVJLQNKX-BQULDOBHSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1-methylpyrazol-4-yl)phenol Chemical compound CN1N=CC(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)=C1 HNEXFBUVJLQNKX-BQULDOBHSA-N 0.000 description 1
- FNJISEJVGHYIJN-PJTPKWCPSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1H-pyrazol-4-yl)phenol Chemical compound F[C@@H]1[C@H]2CCC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C=1C=NNC=1)O)N2 FNJISEJVGHYIJN-PJTPKWCPSA-N 0.000 description 1
- KJPRKHWZBYGORI-TUTGDRGFSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(1H-pyrazol-5-yl)phenol Chemical compound F[C@@H]1[C@H]2CCC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C1=NNC=C1)O)N2 KJPRKHWZBYGORI-TUTGDRGFSA-N 0.000 description 1
- VJFMOQDIKNJRKH-WYGDDPHOSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(2-methyl-1,3-oxazol-4-yl)phenol Chemical compound CC1=NC(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)=CO1 VJFMOQDIKNJRKH-WYGDDPHOSA-N 0.000 description 1
- QMBDMOPIBRPNAQ-PONRLDDASA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(2-methyl-1,3-oxazol-5-yl)phenol Chemical compound CC1=NC=C(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)O1 QMBDMOPIBRPNAQ-PONRLDDASA-N 0.000 description 1
- NXPUWXJNFRDKRQ-PONRLDDASA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(2-methyl-1,3-thiazol-5-yl)phenol Chemical compound CC1=NC=C(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)S1 NXPUWXJNFRDKRQ-PONRLDDASA-N 0.000 description 1
- RPUXDKLMEXECRB-SQWJVJANSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(2-methylpyridin-4-yl)phenol Chemical compound CC1=NC=CC(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)=C1 RPUXDKLMEXECRB-SQWJVJANSA-N 0.000 description 1
- NDMGQWUWHHBIOQ-TUTGDRGFSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(3-fluoro-1-methylpyrazol-4-yl)phenol Chemical compound FC1=NN(C=C1C=1C=CC(=C(C=1)O)C=1N=NC(=CC=1)O[C@@H]1[C@@H]([C@H]2CCC[C@@H](C1)N2)F)C NDMGQWUWHHBIOQ-TUTGDRGFSA-N 0.000 description 1
- GZDOJUMXLDPMBL-TUTGDRGFSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(3-methyl-1,2,4-triazol-1-yl)phenol Chemical compound CC(N=C1)=NN1C(C=C1)=CC(O)=C1C(N=N1)=CC=C1O[C@@H](C[C@H]1N[C@@H]2CCC1)[C@@H]2F GZDOJUMXLDPMBL-TUTGDRGFSA-N 0.000 description 1
- HBENPMYIDPFOOZ-FAFONEJGSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(3-methyl-1,2-oxazol-4-yl)phenol Chemical compound CC1=NOC=C1C(C=C1)=CC(O)=C1C(N=N1)=CC=C1O[C@@H](C[C@H]1N[C@@H]2CCC1)[C@@H]2F HBENPMYIDPFOOZ-FAFONEJGSA-N 0.000 description 1
- FEACPKBHQYCXDK-DKQPGVRISA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(5-methyl-1,3,4-oxadiazol-2-yl)phenol Chemical compound CC1=NN=C(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)O1 FEACPKBHQYCXDK-DKQPGVRISA-N 0.000 description 1
- BBLAAZNJNZURSU-DKQPGVRISA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(5-methyl-1,3,4-thiadiazol-2-yl)phenol Chemical compound CC1=NN=C(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)S1 BBLAAZNJNZURSU-DKQPGVRISA-N 0.000 description 1
- MMHHUNWPJTVPNQ-DDFQMXDRSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(5-methylfuran-2-yl)phenol Chemical compound CC1=CC=C(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)O1 MMHHUNWPJTVPNQ-DDFQMXDRSA-N 0.000 description 1
- JKVNMYCGUKHXPS-DTPUHQDNSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(5-methylfuran-3-yl)phenol Chemical compound F[C@@H]1[C@H]2CCC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C1=COC(=C1)C)O)N2 JKVNMYCGUKHXPS-DTPUHQDNSA-N 0.000 description 1
- QFXYIOINCZCPNG-DDFQMXDRSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(5-methylpyrazin-2-yl)phenol Chemical compound CC(N=C1)=CN=C1C(C=C1)=CC(O)=C1C(N=N1)=CC=C1O[C@@H](C[C@H]1N[C@@H]2CCC1)[C@@H]2F QFXYIOINCZCPNG-DDFQMXDRSA-N 0.000 description 1
- KHBGRDJPPYMWMF-SQWJVJANSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(5-methylpyridin-3-yl)phenol Chemical compound CC1=CN=CC(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)=C1 KHBGRDJPPYMWMF-SQWJVJANSA-N 0.000 description 1
- JOWWJBDCFSQASS-SHLYYBDNSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(5-methylthiophen-2-yl)phenol Chemical compound F[C@@H]1[C@H]2CCC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C=1SC(=CC=1)C)O)N2 JOWWJBDCFSQASS-SHLYYBDNSA-N 0.000 description 1
- MNHRSZOEJXMQEJ-DTPUHQDNSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(5-methylthiophen-3-yl)phenol Chemical compound F[C@@H]1[C@H]2CCC[C@@H](C[C@@H]1OC1=CC=C(N=N1)C1=C(C=C(C=C1)C1=CSC(=C1)C)O)N2 MNHRSZOEJXMQEJ-DTPUHQDNSA-N 0.000 description 1
- NICIBENMMWERFO-SHLYYBDNSA-N 2-[6-[[(1R,2R,3S,5S)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-yl]oxy]pyridazin-3-yl]-5-(6-methoxypyridazin-4-yl)phenol Chemical compound COC1=CC(C(C=C2)=CC(O)=C2C(N=N2)=CC=C2O[C@@H](C[C@H]2N[C@@H]3CCC2)[C@@H]3F)=CN=N1 NICIBENMMWERFO-SHLYYBDNSA-N 0.000 description 1
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2020
- 2020-02-06 JP JP2021546237A patent/JP7603594B2/ja active Active
- 2020-02-06 WO PCT/US2020/017086 patent/WO2020163647A1/en not_active Ceased
- 2020-02-06 EP EP20752875.3A patent/EP3921311A4/en active Pending
- 2020-02-06 CN CN202080027013.1A patent/CN113661162A/zh active Pending
- 2020-02-06 CN CN202411801030.2A patent/CN119638696A/zh active Pending
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2021
- 2021-07-29 US US17/388,093 patent/US12522597B2/en active Active
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