JP2020522490A5 - - Google Patents
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- Publication number
- JP2020522490A5 JP2020522490A5 JP2019566121A JP2019566121A JP2020522490A5 JP 2020522490 A5 JP2020522490 A5 JP 2020522490A5 JP 2019566121 A JP2019566121 A JP 2019566121A JP 2019566121 A JP2019566121 A JP 2019566121A JP 2020522490 A5 JP2020522490 A5 JP 2020522490A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxo
- dihydroisobenzofuran
- pyrazole
- piperazine
- 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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- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 7
- -1 isooxazolyl Chemical group 0.000 claims 102
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 57
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 20
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- XVIAPHVAGFEFFN-UHFFFAOYSA-N pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1 XVIAPHVAGFEFFN-UHFFFAOYSA-N 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims 7
- 125000005348 fluorocycloalkyl group Chemical group 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000002883 imidazolyl group Chemical group 0.000 claims 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 6
- 125000001425 triazolyl group Chemical group 0.000 claims 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 125000005605 benzo group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 claims 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000000335 thiazolyl group Chemical group 0.000 claims 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 3
- IZQBCUVEGMGGDF-SDBXPKJASA-N C[C@H]1CNC[C@H](N1)C1=C(C)C2=C(C=C1)C(=O)OC2 Chemical compound C[C@H]1CNC[C@H](N1)C1=C(C)C2=C(C=C1)C(=O)OC2 IZQBCUVEGMGGDF-SDBXPKJASA-N 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- BAOUQBRSCIHBDU-XLDIYJRPSA-N CC1=CC(=NC=C1C#N)N1N=CC(=N1)C(C)N1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=N1)C(C)N1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C BAOUQBRSCIHBDU-XLDIYJRPSA-N 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 2
- PLIYIVRXVHFYLR-UHFFFAOYSA-N OCC1N(CC(NC1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C Chemical compound OCC1N(CC(NC1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C PLIYIVRXVHFYLR-UHFFFAOYSA-N 0.000 claims 2
- 208000004880 Polyuria Diseases 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 230000035619 diuresis Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 2
- 208000002815 pulmonary hypertension Diseases 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 1
- BNSMCPQFZIYLEG-NRFANRHFSA-N 4-methoxy-6-[4-[[(3R)-3-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)piperazin-1-yl]methyl]pyrazol-1-yl]pyridine-3-carbonitrile Chemical compound COC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C BNSMCPQFZIYLEG-NRFANRHFSA-N 0.000 claims 1
- QLSSHLCAABNEFA-QHCPKHFHSA-N 4-methoxy-6-[5-[[(5R)-5-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)-2-oxo-1,3-oxazolidin-3-yl]methyl]pyridin-2-yl]pyridine-3-carbonitrile Chemical compound COC1=CC(=NC=C1C#N)C1=NC=C(C=C1)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O QLSSHLCAABNEFA-QHCPKHFHSA-N 0.000 claims 1
- DGSGLUKYJOQJLL-UHFFFAOYSA-N 4-methyl-3h-2-benzofuran-1-one Chemical compound CC1=CC=CC2=C1COC2=O DGSGLUKYJOQJLL-UHFFFAOYSA-N 0.000 claims 1
- UHCDBTFXHUXRCE-HJPURHCSSA-N 4-methyl-5-[(2R,6S)-6-methyl-4-[[1-(2-methylpyridin-4-yl)pyrazol-4-yl]methyl]piperazin-2-yl]-3H-2-benzofuran-1-one Chemical compound CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1C=NN(C=1)C1=CC(=NC=C1)C)C)=O UHCDBTFXHUXRCE-HJPURHCSSA-N 0.000 claims 1
- UTGZFFHEBYYJLK-FPTDNZKUSA-N 5-[(2R,6S)-4-[[2-(4,5-dimethylimidazol-1-yl)pyrimidin-5-yl]methyl]-6-methylpiperazin-2-yl]-4-methyl-3H-2-benzofuran-1-one Chemical compound CC=1N=CN(C=1C)C1=NC=C(C=N1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C UTGZFFHEBYYJLK-FPTDNZKUSA-N 0.000 claims 1
- RUXZXBWKCLAWCM-RBBKRZOGSA-N 6-[4-[[(3R,4R)-4-hydroxy-3-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)piperidin-1-yl]methyl]triazol-1-yl]-4-methylpyridine-3-carbonitrile Chemical compound O[C@H]1[C@@H](CN(CC1)CC=1N=NN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C RUXZXBWKCLAWCM-RBBKRZOGSA-N 0.000 claims 1
- RTNFSRGRLBBJOB-UHFFFAOYSA-N 6-[4-[[4-hydroxy-3,3-dimethyl-5-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)piperidin-1-yl]methyl]pyrazol-1-yl]-4-methylpyridine-3-carbonitrile Chemical compound OC1C(CN(CC1C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)(C)C RTNFSRGRLBBJOB-UHFFFAOYSA-N 0.000 claims 1
- 208000009304 Acute Kidney Injury Diseases 0.000 claims 1
- FOJXKTXYPBLGCE-FQEVSTJZSA-N C(#N)C=1C(=CC(=NC=1)N1N=C(C(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C(=O)N)OC Chemical compound C(#N)C=1C(=CC(=NC=1)N1N=C(C(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C(=O)N)OC FOJXKTXYPBLGCE-FQEVSTJZSA-N 0.000 claims 1
- FNCOTDVQYBVNKZ-DEOSSOPVSA-N C(C)(=O)N1[C@@H](CN(CC1)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound C(C)(=O)N1[C@@H](CN(CC1)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C FNCOTDVQYBVNKZ-DEOSSOPVSA-N 0.000 claims 1
- XASQBZKNVFXTQL-QHCPKHFHSA-N C(C)(C)OC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound C(C)(C)OC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C XASQBZKNVFXTQL-QHCPKHFHSA-N 0.000 claims 1
- RJULKHUGGHNZRY-QFIPXVFZSA-N C(C)OC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound C(C)OC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C RJULKHUGGHNZRY-QFIPXVFZSA-N 0.000 claims 1
- PECIXRIFEXUWQN-IYUJOPAMSA-N C(OC1=CC(=NC=C1C#N)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)([2H])([2H])[2H] Chemical compound C(OC1=CC(=NC=C1C#N)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)([2H])([2H])[2H] PECIXRIFEXUWQN-IYUJOPAMSA-N 0.000 claims 1
- FVNLYJVTLHWBQP-DEOSSOPVSA-N C1(CC1)C1=NN(C=C1CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C1=NC=C(C#N)C(=C1)C Chemical compound C1(CC1)C1=NN(C=C1CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C1=NC=C(C#N)C(=C1)C FVNLYJVTLHWBQP-DEOSSOPVSA-N 0.000 claims 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 1
- YZNBIUBNAWQMMA-UHFFFAOYSA-N CC1(CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC1=NN(N=C1)C1=NC=C(C#N)C(=C1)C)C Chemical compound CC1(CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC1=NN(N=C1)C1=NC=C(C#N)C(=C1)C)C YZNBIUBNAWQMMA-UHFFFAOYSA-N 0.000 claims 1
- NZXBQRXJRZVIER-UHFFFAOYSA-N CC1(CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC1=NN(N=C1)C1=NC=C(C#N)C(=C1)OC)C Chemical compound CC1(CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC1=NN(N=C1)C1=NC=C(C#N)C(=C1)OC)C NZXBQRXJRZVIER-UHFFFAOYSA-N 0.000 claims 1
- UGNJOBSGYFQSAS-UHFFFAOYSA-N CC1(CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC1=NN(N=C1C)C1=NC=C(C#N)C(=C1)C)C Chemical compound CC1(CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC1=NN(N=C1C)C1=NC=C(C#N)C(=C1)C)C UGNJOBSGYFQSAS-UHFFFAOYSA-N 0.000 claims 1
- YWXLFBTWOQAKKR-UHFFFAOYSA-N CC1(OC(CN(C1)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1(OC(CN(C1)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C)C YWXLFBTWOQAKKR-UHFFFAOYSA-N 0.000 claims 1
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