JP2020522490A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- QUJYQVMHAZZNKS-QFIPXVFZSA-N CC1=C(C#N)C(=CC(=N1)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1=C(C#N)C(=CC(=N1)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C QUJYQVMHAZZNKS-QFIPXVFZSA-N 0.000 claims 1
- VSERMWKUVIXRPF-QHCPKHFHSA-N CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CC=C(C=C2)C#N)CCO1 Chemical compound CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CC=C(C=C2)C#N)CCO1 VSERMWKUVIXRPF-QHCPKHFHSA-N 0.000 claims 1
- XHOJIHUAVXRRBK-QHCPKHFHSA-N CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CC=CC(=C2)C#N)CCO1 Chemical compound CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CC=CC(=C2)C#N)CCO1 XHOJIHUAVXRRBK-QHCPKHFHSA-N 0.000 claims 1
- KFFMGCSKYCYUHL-NRFANRHFSA-N CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CC=NC=C2)CCO1 Chemical compound CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CC=NC=C2)CCO1 KFFMGCSKYCYUHL-NRFANRHFSA-N 0.000 claims 1
- UTKIXACLZBQGBS-QFIPXVFZSA-N CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CN=CC(=C2)C#N)CCO1 Chemical compound CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CN=CC(=C2)C#N)CCO1 UTKIXACLZBQGBS-QFIPXVFZSA-N 0.000 claims 1
- IQLDPNRCMGDCKW-FQEVSTJZSA-N CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CSC=C2)CCO1 Chemical compound CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=CSC=C2)CCO1 IQLDPNRCMGDCKW-FQEVSTJZSA-N 0.000 claims 1
- AVWGBDGKSODNFM-IBGZPJMESA-N CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=NC=CN=C2)CCO1 Chemical compound CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN(N=C2)C2=NC=CN=C2)CCO1 AVWGBDGKSODNFM-IBGZPJMESA-N 0.000 claims 1
- XBDIXGKLIFCJIH-NRFANRHFSA-N CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN=C(C=C2)N2C=NC(=C2)C#N)CCO1 Chemical compound CC1=C(C=CC2=C1COC2=O)[C@@H]1CN(CC2=CN=C(C=C2)N2C=NC(=C2)C#N)CCO1 XBDIXGKLIFCJIH-NRFANRHFSA-N 0.000 claims 1
- UAIWBPQFBNHNTP-NRFANRHFSA-N CC1=C2COC(=O)C2=CC=C1[C@@H]1CN(CC2=CN(C=N2)C2=CC=C(C=N2)C#N)CCO1 Chemical compound CC1=C2COC(=O)C2=CC=C1[C@@H]1CN(CC2=CN(C=N2)C2=CC=C(C=N2)C#N)CCO1 UAIWBPQFBNHNTP-NRFANRHFSA-N 0.000 claims 1
- RNMKYLGHTXFSPY-NRFANRHFSA-N CC1=C2COC(=O)C2=CC=C1[C@@H]1CN(CC2=CN=C(C=C2)N2C=C(C=N2)C#N)CCN1 Chemical compound CC1=C2COC(=O)C2=CC=C1[C@@H]1CN(CC2=CN=C(C=C2)N2C=C(C=N2)C#N)CCN1 RNMKYLGHTXFSPY-NRFANRHFSA-N 0.000 claims 1
- HYAWWCCBOCDGCD-NRFANRHFSA-N CC1=C2COC(=O)C2=CC=C1[C@@H]1CN(CC2=CN=C(C=C2)N2C=NC(=C2)C#N)CCN1 Chemical compound CC1=C2COC(=O)C2=CC=C1[C@@H]1CN(CC2=CN=C(C=C2)N2C=NC(=C2)C#N)CCN1 HYAWWCCBOCDGCD-NRFANRHFSA-N 0.000 claims 1
- JMSAQIQPDGJTNE-IBGZPJMESA-N CC1=C2COC(=O)C2=CC=C1[C@@H]1CN(CC2=NN=C(O2)C2=NC=C(C=C2)C#N)CCN1 Chemical compound CC1=C2COC(=O)C2=CC=C1[C@@H]1CN(CC2=NN=C(O2)C2=NC=C(C=C2)C#N)CCN1 JMSAQIQPDGJTNE-IBGZPJMESA-N 0.000 claims 1
- LENWXANFTHMPKX-IBGZPJMESA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC1=CN=C(S1)N1C=NC(=C1)C#N)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC1=CN=C(S1)N1C=NC(=C1)C#N)=O LENWXANFTHMPKX-IBGZPJMESA-N 0.000 claims 1
- AFHBFTIWEBJCAW-NRFANRHFSA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=CC(=NC=1)N1N=C(C=C1)C#N)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=CC(=NC=1)N1N=C(C=C1)C#N)=O AFHBFTIWEBJCAW-NRFANRHFSA-N 0.000 claims 1
- QTSUKUQQNWCRFT-FQEVSTJZSA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=CC(=NC=1)N1N=CC(=C1)C(=O)N)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=CC(=NC=1)N1N=CC(=C1)C(=O)N)=O QTSUKUQQNWCRFT-FQEVSTJZSA-N 0.000 claims 1
- AFJMSLZPZGYUTI-FQEVSTJZSA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=CC(=NC=1)N1N=NC(=C1)C#N)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=CC(=NC=1)N1N=NC(=C1)C#N)=O AFJMSLZPZGYUTI-FQEVSTJZSA-N 0.000 claims 1
- HSYPUMGZFBUANS-FQEVSTJZSA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=NC(=NC=1)N1C=NC(=C1)C#N)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=NC(=NC=1)N1C=NC(=C1)C#N)=O HSYPUMGZFBUANS-FQEVSTJZSA-N 0.000 claims 1
- IEIQZVILPLLCKZ-SFHVURJKSA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=NC(=NC=1)N1N=C(N=C1)C#N)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=NC(=NC=1)N1N=C(N=C1)C#N)=O IEIQZVILPLLCKZ-SFHVURJKSA-N 0.000 claims 1
- FXDDXQMCJHTUHM-QFIPXVFZSA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=NN(C=1)C1=NC=CC(=C1)N1C(OCC1)=O)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCN1)CC=1C=NN(C=1)C1=NC=CC(=C1)N1C(OCC1)=O)=O FXDDXQMCJHTUHM-QFIPXVFZSA-N 0.000 claims 1
- TZFXUPRXXNWDPJ-QHCPKHFHSA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCO1)CC=1C=NN(C=1)C1=C2C(=NC=C1)N(C=C2)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCO1)CC=1C=NN(C=1)C1=C2C(=NC=C1)N(C=C2)C)=O TZFXUPRXXNWDPJ-QHCPKHFHSA-N 0.000 claims 1
- PLAOHRCQMTVRJB-QHCPKHFHSA-N CC1=C2COC(C2=CC=C1[C@@H]1CN(CCO1)CC=1C=NN(C=1)C1=CC=C(C=C1)S(=O)(=O)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@@H]1CN(CCO1)CC=1C=NN(C=1)C1=CC=C(C=C1)S(=O)(=O)C)=O PLAOHRCQMTVRJB-QHCPKHFHSA-N 0.000 claims 1
- BRHNWKUHPIHSJR-FQEVSTJZSA-N CC1=C2COC(C2=CC=C1[C@H]1NCCN(C1)CC=1C=NC(=CC=1)C1=NC(=NO1)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1NCCN(C1)CC=1C=NC(=CC=1)C1=NC(=NO1)C)=O BRHNWKUHPIHSJR-FQEVSTJZSA-N 0.000 claims 1
- XCIRHMPJUAZFCW-FQEVSTJZSA-N CC1=C2COC(C2=CC=C1[C@H]1NCCN(C1)CC=1C=NC(=CC=1)N1N=C(N=C1)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1NCCN(C1)CC=1C=NC(=CC=1)N1N=C(N=C1)C)=O XCIRHMPJUAZFCW-FQEVSTJZSA-N 0.000 claims 1
- RTRCGJHUKSITDQ-FQEVSTJZSA-N CC1=C2COC(C2=CC=C1[C@H]1NCCN(C1)CC=1C=NC(=CC=1)N1N=NC(=C1)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1NCCN(C1)CC=1C=NC(=CC=1)N1N=NC(=C1)C)=O RTRCGJHUKSITDQ-FQEVSTJZSA-N 0.000 claims 1
- ONBVDBPAUCYFAR-QFIPXVFZSA-N CC1=C2COC(C2=CC=C1[C@H]1NCCN(C1)CC=1C=NC(=CC=1C)N1C=NC(=C1)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1NCCN(C1)CC=1C=NC(=CC=1C)N1C=NC(=C1)C)=O ONBVDBPAUCYFAR-QFIPXVFZSA-N 0.000 claims 1
- ZUMNHPVBUPZXII-FYSMJZIKSA-N CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1C=CC(=NC=1)C=1C=NC(=CC=1)S(=O)(=O)C)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1C=CC(=NC=1)C=1C=NC(=CC=1)S(=O)(=O)C)C)=O ZUMNHPVBUPZXII-FYSMJZIKSA-N 0.000 claims 1
- VIVWWCLNXZTZEK-BTYIYWSLSA-N CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1C=NN(C=1)C1=NC=C(N=C1)C)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1C=NN(C=1)C1=NC=C(N=C1)C)C)=O VIVWWCLNXZTZEK-BTYIYWSLSA-N 0.000 claims 1
- DNVXKHGHNCDGTR-FPTDNZKUSA-N CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1C=NN(C=1)C=1C=NC(=NC=1)C)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1C=NN(C=1)C=1C=NC(=NC=1)C)C)=O DNVXKHGHNCDGTR-FPTDNZKUSA-N 0.000 claims 1
- VKFHSAVRWSMXGD-AOMKIAJQSA-N CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1N=CN(C=1)C1=C(C=NC=C1)C)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1N=CN(C=1)C1=C(C=NC=C1)C)C)=O VKFHSAVRWSMXGD-AOMKIAJQSA-N 0.000 claims 1
- QEQFCIMVHIQDPW-HJPURHCSSA-N CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1N=CN(C=1)C=1C=NC(=CC=1)C)C)=O Chemical compound CC1=C2COC(C2=CC=C1[C@H]1N[C@H](CN(C1)CC=1N=CN(C=1)C=1C=NC(=CC=1)C)C)=O QEQFCIMVHIQDPW-HJPURHCSSA-N 0.000 claims 1
- ZWLBUWKXTXTPRD-QFIPXVFZSA-N CC1=CC(=NC(C)=C1C#N)N1N=CC(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)=N1 Chemical compound CC1=CC(=NC(C)=C1C#N)N1N=CC(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)=N1 ZWLBUWKXTXTPRD-QFIPXVFZSA-N 0.000 claims 1
- ZGUYFMBERAXOKX-NZQKXSOJSA-N CC1=CC(=NC=C1C#N)C1=NC(CN2CC[C@@H](O)[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)=CO1 Chemical compound CC1=CC(=NC=C1C#N)C1=NC(CN2CC[C@@H](O)[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)=CO1 ZGUYFMBERAXOKX-NZQKXSOJSA-N 0.000 claims 1
- IIIDYIDJAOEJEX-UHFFFAOYSA-N CC1=CC(=NC=C1C#N)C1=NN=C(CN2CC(NC(C)(C)C2)C2=CC=C3C(=O)OCC3=C2C)O1 Chemical compound CC1=CC(=NC=C1C#N)C1=NN=C(CN2CC(NC(C)(C)C2)C2=CC=C3C(=O)OCC3=C2C)O1 IIIDYIDJAOEJEX-UHFFFAOYSA-N 0.000 claims 1
- WGCCEHKAKJCFLI-FQEVSTJZSA-N CC1=CC(=NC=C1C#N)C=1OC(=NN=1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)C=1OC(=NN=1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C WGCCEHKAKJCFLI-FQEVSTJZSA-N 0.000 claims 1
- VVHJLZACRLOVHU-FQEVSTJZSA-N CC1=CC(=NC=C1C#N)C=1OC(=NN=1)CN1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)C=1OC(=NN=1)CN1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C VVHJLZACRLOVHU-FQEVSTJZSA-N 0.000 claims 1
- AKXKCTKYQFEWNZ-FQEVSTJZSA-N CC1=CC(=NC=C1C#N)C=1SC(=CN=1)C(=O)N1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)C=1SC(=CN=1)C(=O)N1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C AKXKCTKYQFEWNZ-FQEVSTJZSA-N 0.000 claims 1
- NNKKHXUWMUBXOJ-XDHUDOTRSA-N CC1=CC(=NC=C1C#N)N1C(C=C(C=C1)CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C)=O Chemical compound CC1=CC(=NC=C1C#N)N1C(C=C(C=C1)CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C)=O NNKKHXUWMUBXOJ-XDHUDOTRSA-N 0.000 claims 1
- BCFKNKWXUHBGGG-UGNFMNBCSA-N CC1=CC(=NC=C1C#N)N1C(CC(C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CC1=CC(=NC=C1C#N)N1C(CC(C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O BCFKNKWXUHBGGG-UGNFMNBCSA-N 0.000 claims 1
- RWDJHOGMWRGHRL-LFABVHOISA-N CC1=CC(=NC=C1C#N)N1C(OC(C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CC1=CC(=NC=C1C#N)N1C(OC(C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O RWDJHOGMWRGHRL-LFABVHOISA-N 0.000 claims 1
- WJMSUJGPOZISLG-UHFFFAOYSA-N CC1=CC(=NC=C1C#N)N1C=C(CN2CC(CO)NC(C2)C2=CC=C3C(=O)OCC3=C2C)N=N1 Chemical compound CC1=CC(=NC=C1C#N)N1C=C(CN2CC(CO)NC(C2)C2=CC=C3C(=O)OCC3=C2C)N=N1 WJMSUJGPOZISLG-UHFFFAOYSA-N 0.000 claims 1
- YICNMSFPDIOSGD-UHFFFAOYSA-N CC1=CC(=NC=C1C#N)N1C=C(CN2CC(F)CC(C2)C2=CC=C3C(=O)OCC3=C2C)N=N1 Chemical compound CC1=CC(=NC=C1C#N)N1C=C(CN2CC(F)CC(C2)C2=CC=C3C(=O)OCC3=C2C)N=N1 YICNMSFPDIOSGD-UHFFFAOYSA-N 0.000 claims 1
- OBXNXAOEDFSFFT-JTHBVZDNSA-N CC1=CC(=NC=C1C#N)N1C=C(CN2CC[C@@H](O)[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)C=N1 Chemical compound CC1=CC(=NC=C1C#N)N1C=C(CN2CC[C@@H](O)[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)C=N1 OBXNXAOEDFSFFT-JTHBVZDNSA-N 0.000 claims 1
- LCJHMJQPSOGTMK-QHCPKHFHSA-N CC1=CC(=NC=C1C#N)N1N=C(C(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1=CC(=NC=C1C#N)N1N=C(C(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C LCJHMJQPSOGTMK-QHCPKHFHSA-N 0.000 claims 1
- YLVOURJTKPPUDU-QFIPXVFZSA-N CC1=CC(=NC=C1C#N)N1N=C(C(=N1)C)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=C(C(=N1)C)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C YLVOURJTKPPUDU-QFIPXVFZSA-N 0.000 claims 1
- GWUUGKSEIAEARJ-UHFFFAOYSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C(C(NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C(C(NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C GWUUGKSEIAEARJ-UHFFFAOYSA-N 0.000 claims 1
- AAWRZXNVPSFVQM-UHFFFAOYSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C(CNC(C1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C(CNC(C1)C=1C(=C2COC(C2=CC=1)=O)C)C AAWRZXNVPSFVQM-UHFFFAOYSA-N 0.000 claims 1
- IALYESFBDLUMTP-FQEVSTJZSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O IALYESFBDLUMTP-FQEVSTJZSA-N 0.000 claims 1
- HKFMIDVXUGKIQJ-UHFFFAOYSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1CC(C(CC1)=O)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1CC(C(CC1)=O)C=1C(=C2COC(C2=CC=1)=O)C HKFMIDVXUGKIQJ-UHFFFAOYSA-N 0.000 claims 1
- XGFQPRLLQXBDSO-KESSSICBSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1CC(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1CC(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C XGFQPRLLQXBDSO-KESSSICBSA-N 0.000 claims 1
- DROCQKKPPKNLHA-JOCHJYFZSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C DROCQKKPPKNLHA-JOCHJYFZSA-N 0.000 claims 1
- HFJPFNAKIMFQKB-NRFANRHFSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NC(C1)=O)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NC(C1)=O)C=1C(=C2COC(C2=CC=1)=O)C HFJPFNAKIMFQKB-NRFANRHFSA-N 0.000 claims 1
- DROCQKKPPKNLHA-QFIPXVFZSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C DROCQKKPPKNLHA-QFIPXVFZSA-N 0.000 claims 1
- LOFUMCJUAHZTJC-NRFANRHFSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](OCC1=O)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](OCC1=O)C=1C(=C2COC(C2=CC=1)=O)C LOFUMCJUAHZTJC-NRFANRHFSA-N 0.000 claims 1
- NIYZKVCTXLQBBB-QHCPKHFHSA-N CC1=CC(=NC=C1C#N)N1N=CC(=C1C)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=C1C)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C NIYZKVCTXLQBBB-QHCPKHFHSA-N 0.000 claims 1
- NRCYDDLRPFXMNA-NYHFZMIOSA-N CC1=CC(=NC=C1C#N)N1N=CC(=N1)CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=N1)CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C NRCYDDLRPFXMNA-NYHFZMIOSA-N 0.000 claims 1
- JVTSOAPPUSBKRI-NRFANRHFSA-N CC1=CC(=NC=C1C#N)N1N=CC(=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=CC(=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C JVTSOAPPUSBKRI-NRFANRHFSA-N 0.000 claims 1
- YWFOOKUMNWREKG-NRFANRHFSA-N CC1=CC(=NC=C1C#N)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=CC(=NC=C1C#N)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C YWFOOKUMNWREKG-NRFANRHFSA-N 0.000 claims 1
- DJAVJNFMIPOVSP-WNSKOXEYSA-N CC1=CC(=NC=C1C#N)N1N=NC(=C1C)CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1=CC(=NC=C1C#N)N1N=NC(=C1C)CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C DJAVJNFMIPOVSP-WNSKOXEYSA-N 0.000 claims 1
- AVPBAQUSTPFOAD-NRFANRHFSA-N CC1=CN(C=N1)C1=NC=C(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)C=C1F Chemical compound CC1=CN(C=N1)C1=NC=C(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)C=C1F AVPBAQUSTPFOAD-NRFANRHFSA-N 0.000 claims 1
- GMQKWUNJGGGFNG-XDHUDOTRSA-N CC1=NC(=CC(=C1)N1C=NC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CC1=NC(=CC(=C1)N1C=NC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C)C GMQKWUNJGGGFNG-XDHUDOTRSA-N 0.000 claims 1
- CKBVZOQTUBGLTC-NRFANRHFSA-N CC1=NC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC1=NC(=NC=C1C#N)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C CKBVZOQTUBGLTC-NRFANRHFSA-N 0.000 claims 1
- ZUTYKNUINNOAEO-FQEVSTJZSA-N CC1=NN=C(C)N1C1=NC=C(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)C=N1 Chemical compound CC1=NN=C(C)N1C1=NC=C(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)C=N1 ZUTYKNUINNOAEO-FQEVSTJZSA-N 0.000 claims 1
- MSLPFTPAFSHBCU-NRFANRHFSA-N CC=1N(C=C(N=1)C)C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC=1N(C=C(N=1)C)C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C MSLPFTPAFSHBCU-NRFANRHFSA-N 0.000 claims 1
- ZXVFVKDWMOFOFK-NRFANRHFSA-N CC=1N=CN(C=1C)C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound CC=1N=CN(C=1C)C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C ZXVFVKDWMOFOFK-NRFANRHFSA-N 0.000 claims 1
- JAANPPVQUVNNGE-NRFANRHFSA-N CN1C(=O)OC2=C(F)C=C(C=C12)N1C=C(CN2CCN[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)C=N1 Chemical compound CN1C(=O)OC2=C(F)C=C(C=C12)N1C=C(CN2CCN[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)C=N1 JAANPPVQUVNNGE-NRFANRHFSA-N 0.000 claims 1
- DXHGBTIPIQKXBG-HJPURHCSSA-N CN1C(N(C=C1CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C)C1=CC(=NC=C1)C)=O Chemical compound CN1C(N(C=C1CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C)C1=CC(=NC=C1)C)=O DXHGBTIPIQKXBG-HJPURHCSSA-N 0.000 claims 1
- JZYAJLANKMJYJS-NRFANRHFSA-N CN1C(OC2=C1C(=C(C=C2)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C)=O Chemical compound CN1C(OC2=C1C(=C(C=C2)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C)=O JZYAJLANKMJYJS-NRFANRHFSA-N 0.000 claims 1
- CQONUKWZYWUQBY-FQEVSTJZSA-N CN1C(OC2=C1C=C(C=C2)C=1SC(=CN=1)C(=O)N1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CN1C(OC2=C1C=C(C=C2)C=1SC(=CN=1)C(=O)N1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O CQONUKWZYWUQBY-FQEVSTJZSA-N 0.000 claims 1
- WESIBBXZEOQRMY-NRFANRHFSA-N CN1C(OC2=C1C=C(C=C2)N1N=CC(=C1)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O)=O Chemical compound CN1C(OC2=C1C=C(C=C2)N1N=CC(=C1)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O)=O WESIBBXZEOQRMY-NRFANRHFSA-N 0.000 claims 1
- YABZLBRUVCDZOY-FQEVSTJZSA-N CN1C(OC2=C1C=C(C=C2)N1N=CC(=C1)CN1C[C@H](NC(C1)=O)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CN1C(OC2=C1C=C(C=C2)N1N=CC(=C1)CN1C[C@H](NC(C1)=O)C=1C(=C2COC(C2=CC=1)=O)C)=O YABZLBRUVCDZOY-FQEVSTJZSA-N 0.000 claims 1
- USGPIPXLGCBGPJ-NRFANRHFSA-N CN1C(OC2=C1C=C(C=C2)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CN1C(OC2=C1C=C(C=C2)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O USGPIPXLGCBGPJ-NRFANRHFSA-N 0.000 claims 1
- MJTLZZDODXSIEL-IBGZPJMESA-N CN1C(OC2=C1C=C(C=C2)N1N=NC(=C1)CN1C[C@H](NC(C1)=O)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CN1C(OC2=C1C=C(C=C2)N1N=NC(=C1)CN1C[C@H](NC(C1)=O)C=1C(=C2COC(C2=CC=1)=O)C)=O MJTLZZDODXSIEL-IBGZPJMESA-N 0.000 claims 1
- YSHIFFLINFXTDF-FQEVSTJZSA-N CN1C(OC2=C1C=C(C=C2)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CN1C(OC2=C1C=C(C=C2)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O YSHIFFLINFXTDF-FQEVSTJZSA-N 0.000 claims 1
- NKYUDGMEPJJVEY-QFIPXVFZSA-N CN1C(OC2=C1C=C(C=C2C)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound CN1C(OC2=C1C=C(C=C2C)N1N=CC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O NKYUDGMEPJJVEY-QFIPXVFZSA-N 0.000 claims 1
- CWBLNPOSRCEUKB-FYSMJZIKSA-N CN1C=C(C=CC1=O)C1=NC=C(C=C1)CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound CN1C=C(C=CC1=O)C1=NC=C(C=C1)CN1C[C@@H](N[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)C CWBLNPOSRCEUKB-FYSMJZIKSA-N 0.000 claims 1
- CDVYDLNDSZKCQY-QHCPKHFHSA-N CN1CCN(CC2=CN(N=C2)C2=NC=C(C#N)C(C)=C2)C[C@H]1C1=CC=C2C(=O)OCC2=C1C Chemical compound CN1CCN(CC2=CN(N=C2)C2=NC=C(C#N)C(C)=C2)C[C@H]1C1=CC=C2C(=O)OCC2=C1C CDVYDLNDSZKCQY-QHCPKHFHSA-N 0.000 claims 1
- LETRQLROPFHGBM-NRFANRHFSA-N COC1=C(C#N)C(=CC(=N1)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound COC1=C(C#N)C(=CC(=N1)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C LETRQLROPFHGBM-NRFANRHFSA-N 0.000 claims 1
- VVTZVYQPSGGOSA-QFIPXVFZSA-N COC1=C(C=NC(=C1)C1=NC=C(CN2CCO[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)S1)C#N Chemical compound COC1=C(C=NC(=C1)C1=NC=C(CN2CCO[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)S1)C#N VVTZVYQPSGGOSA-QFIPXVFZSA-N 0.000 claims 1
- DTCZYBINBLXTIB-NRFANRHFSA-N COC1=C(C=NC(=C1)N1C=NC(=C1)C)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=C(C=NC(=C1)N1C=NC(=C1)C)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C DTCZYBINBLXTIB-NRFANRHFSA-N 0.000 claims 1
- YUBNCVWNBLDJDH-FQEVSTJZSA-N COC1=C(C=NN1C1=NC=C(C#N)C(=C1)C)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound COC1=C(C=NN1C1=NC=C(C#N)C(=C1)C)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O YUBNCVWNBLDJDH-FQEVSTJZSA-N 0.000 claims 1
- UCXCDUJJXTYVOW-QFIPXVFZSA-N COC1=C(C=NN1C1=NC=C(C#N)C(=C1)C)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=C(C=NN1C1=NC=C(C#N)C(=C1)C)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C UCXCDUJJXTYVOW-QFIPXVFZSA-N 0.000 claims 1
- JKHBFCSFJVDQFR-NRFANRHFSA-N COC1=C(C=NN1C=1C=CC2=C(N(C(O2)=O)C)C=1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=C(C=NN1C=1C=CC2=C(N(C(O2)=O)C)C=1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C JKHBFCSFJVDQFR-NRFANRHFSA-N 0.000 claims 1
- ASCTUJAWHXHQFS-NRFANRHFSA-N COC1=C2OC(=O)N(C)C2=CC(=C1)N1C=C(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)C=N1 Chemical compound COC1=C2OC(=O)N(C)C2=CC(=C1)N1C=C(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)C=N1 ASCTUJAWHXHQFS-NRFANRHFSA-N 0.000 claims 1
- AWWSCQBVHSZUTA-PZJWPPBQSA-N COC1=CC(=CC=C1C#N)N1N=NC(CN2CC[C@@H](O)[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)=N1 Chemical compound COC1=CC(=CC=C1C#N)N1N=NC(CN2CC[C@@H](O)[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)=N1 AWWSCQBVHSZUTA-PZJWPPBQSA-N 0.000 claims 1
- KCSCDIKSKJXEKY-NRFANRHFSA-N COC1=CC(=NC(C)=C1C#N)N1C=C(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)N=N1 Chemical compound COC1=CC(=NC(C)=C1C#N)N1C=C(CN2CCN[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)N=N1 KCSCDIKSKJXEKY-NRFANRHFSA-N 0.000 claims 1
- FMOIJQFQXOGUAT-DEOSSOPVSA-N COC1=CC(=NC=C1C#N)C1=NC(=C(C=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)OC Chemical compound COC1=CC(=NC=C1C#N)C1=NC(=C(C=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)OC FMOIJQFQXOGUAT-DEOSSOPVSA-N 0.000 claims 1
- XJLMGCHZLVULCS-QHCPKHFHSA-N COC1=CC(=NC=C1C#N)C1=NC=C(C=C1)CN1C[C@H](NC(C1)=O)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=CC(=NC=C1C#N)C1=NC=C(C=C1)CN1C[C@H](NC(C1)=O)C=1C(=C2COC(C2=CC=1)=O)C XJLMGCHZLVULCS-QHCPKHFHSA-N 0.000 claims 1
- OWTPTSFMXWLEEV-DEOSSOPVSA-N COC1=CC(=NC=C1C#N)C1=NC=C(C=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=CC(=NC=C1C#N)C1=NC=C(C=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C OWTPTSFMXWLEEV-DEOSSOPVSA-N 0.000 claims 1
- OBXIYDWZQSTMOT-VWLOTQADSA-N COC1=CC(=NC=C1C#N)C1=NC=C(C=C1)CN1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=CC(=NC=C1C#N)C1=NC=C(C=C1)CN1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C OBXIYDWZQSTMOT-VWLOTQADSA-N 0.000 claims 1
- LOFNXOUSTINSIZ-FQEVSTJZSA-N COC1=CC(=NC=C1C#N)C=1SC(=CN=1)C(=O)N1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=CC(=NC=C1C#N)C=1SC(=CN=1)C(=O)N1C[C@H](OCC1)C=1C(=C2COC(C2=CC=1)=O)C LOFNXOUSTINSIZ-FQEVSTJZSA-N 0.000 claims 1
- WXUXLPXDFGZMGK-MRNPHLECSA-N COC1=CC(=NC=C1C#N)N1C(CC(C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound COC1=CC(=NC=C1C#N)N1C(CC(C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)=O WXUXLPXDFGZMGK-MRNPHLECSA-N 0.000 claims 1
- KUTWYJWXIHZZIN-UHFFFAOYSA-N COC1=CC(=NC=C1C#N)N1C=C(CN2CC(CO)NC(C2)C2=CC=C3C(=O)OCC3=C2C)C=N1 Chemical compound COC1=CC(=NC=C1C#N)N1C=C(CN2CC(CO)NC(C2)C2=CC=C3C(=O)OCC3=C2C)C=N1 KUTWYJWXIHZZIN-UHFFFAOYSA-N 0.000 claims 1
- SINLUNCRGKLCEJ-RBBKRZOGSA-N COC1=CC(=NC=C1C#N)N1C=C(CN2CC[C@@H](O)[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)C=N1 Chemical compound COC1=CC(=NC=C1C#N)N1C=C(CN2CC[C@@H](O)[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)C=N1 SINLUNCRGKLCEJ-RBBKRZOGSA-N 0.000 claims 1
- USYHZXYKYSCAOA-FQEVSTJZSA-N COC1=CC(=NC=C1C#N)N1C=NC(=C1)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O Chemical compound COC1=CC(=NC=C1C#N)N1C=NC(=C1)CN1C(O[C@@H](C1)C=1C(=C2COC(C2=CC=1)=O)C)=O USYHZXYKYSCAOA-FQEVSTJZSA-N 0.000 claims 1
- WIIXLFNFFWXRRG-NYHFZMIOSA-N COC1=CC(=NC=C1C#N)N1C=NC(CN2C[C@H](C)N[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)=C1 Chemical compound COC1=CC(=NC=C1C#N)N1C=NC(CN2C[C@H](C)N[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)=C1 WIIXLFNFFWXRRG-NYHFZMIOSA-N 0.000 claims 1
- SMWMYDPFUJPDHF-UWEREPPTSA-N COC1=CC(=NC=C1C#N)N1CC(CN2C[C@H](C)N[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)CC1=O Chemical compound COC1=CC(=NC=C1C#N)N1CC(CN2C[C@H](C)N[C@@H](C2)C2=CC=C3C(=O)OCC3=C2C)CC1=O SMWMYDPFUJPDHF-UWEREPPTSA-N 0.000 claims 1
- PAJYZFWOBMBHHU-FQEVSTJZSA-N COC1=CC(=NC=C1C#N)N1N=CC(=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=CC(=NC=C1C#N)N1N=CC(=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C PAJYZFWOBMBHHU-FQEVSTJZSA-N 0.000 claims 1
- YXUJMVXHPUMPQM-PZJWPPBQSA-N COC1=CC(=NC=C1C#N)N1N=CC(CN2CC[C@@H](O)[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)=N1 Chemical compound COC1=CC(=NC=C1C#N)N1N=CC(CN2CC[C@@H](O)[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)=N1 YXUJMVXHPUMPQM-PZJWPPBQSA-N 0.000 claims 1
- XOZAQPATCSISQZ-QKKBWIMNSA-N COC1=CC(=NC=C1C#N)N1N=CC(CN2C[C@H](C)N[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)=N1 Chemical compound COC1=CC(=NC=C1C#N)N1N=CC(CN2C[C@H](C)N[C@@H](C2)C2=C(C)C3=C(C=C2)C(=O)OC3)=N1 XOZAQPATCSISQZ-QKKBWIMNSA-N 0.000 claims 1
- PECIXRIFEXUWQN-FQEVSTJZSA-N COC1=CC(=NC=C1C#N)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=CC(=NC=C1C#N)N1N=NC(=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C PECIXRIFEXUWQN-FQEVSTJZSA-N 0.000 claims 1
- UEHQYCZNUZBZRZ-XOBRGWDASA-N COC1=CC(=NC=N1)N1N=CC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=CC(=NC=N1)N1N=CC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C UEHQYCZNUZBZRZ-XOBRGWDASA-N 0.000 claims 1
- JRLVOGDNOSCFNZ-QKKBWIMNSA-N COC1=NC=C(C=N1)N1N=CC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=NC=C(C=N1)N1N=CC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C JRLVOGDNOSCFNZ-QKKBWIMNSA-N 0.000 claims 1
- RRHOGWUBHJHCAS-NYHFZMIOSA-N COC1=NC=CC(=C1)N1C=NC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound COC1=NC=CC(=C1)N1C=NC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C RRHOGWUBHJHCAS-NYHFZMIOSA-N 0.000 claims 1
- NYRDYSLMHINUTR-QKKBWIMNSA-N C[C@H]1CN(CC2=CN(C(=O)N2C)C2=CC=NC(C)=N2)C[C@H](N1)C1=C(C)C2=C(C=C1)C(=O)OC2 Chemical compound C[C@H]1CN(CC2=CN(C(=O)N2C)C2=CC=NC(C)=N2)C[C@H](N1)C1=C(C)C2=C(C=C1)C(=O)OC2 NYRDYSLMHINUTR-QKKBWIMNSA-N 0.000 claims 1
- VPJAVTWPUNCWFW-DJJJIMSYSA-N C[C@H]1CN(CC2=CN(C=N2)C2=CC=NC(=N2)C(F)F)C[C@H](N1)C1=CC=C2C(=O)OCC2=C1C Chemical compound C[C@H]1CN(CC2=CN(C=N2)C2=CC=NC(=N2)C(F)F)C[C@H](N1)C1=CC=C2C(=O)OCC2=C1C VPJAVTWPUNCWFW-DJJJIMSYSA-N 0.000 claims 1
- VOSSLQPSWSECLU-HJPURHCSSA-N C[C@H]1CN(CC2=CN(C=N2)C2=NC=C(C#N)C(C)=C2)C[C@H](N1)C1=CC=C2C(=O)OCC2=C1C Chemical compound C[C@H]1CN(CC2=CN(C=N2)C2=NC=C(C#N)C(C)=C2)C[C@H](N1)C1=CC=C2C(=O)OCC2=C1C VOSSLQPSWSECLU-HJPURHCSSA-N 0.000 claims 1
- QPZJXMQMZUYLIP-FPTDNZKUSA-N C[C@H]1CN(CC2=CN(N=C2)C2=NC=C(C#N)C(=C2)C(F)(F)F)C[C@H](N1)C1=CC=C2C(=O)OCC2=C1C Chemical compound C[C@H]1CN(CC2=CN(N=C2)C2=NC=C(C#N)C(=C2)C(F)(F)F)C[C@H](N1)C1=CC=C2C(=O)OCC2=C1C QPZJXMQMZUYLIP-FPTDNZKUSA-N 0.000 claims 1
- FGYIBPUBWMYGAK-HJPURHCSSA-N C[C@H]1CN(CC2=CN(N=C2)C2=NC=C(C#N)C(C)=C2)C[C@H](N1)C1=C(C)C2=C(C=C1)C(=O)OC2 Chemical compound C[C@H]1CN(CC2=CN(N=C2)C2=NC=C(C#N)C(C)=C2)C[C@H](N1)C1=C(C)C2=C(C=C1)C(=O)OC2 FGYIBPUBWMYGAK-HJPURHCSSA-N 0.000 claims 1
- ORMLUKIMTLUHOK-NYHFZMIOSA-N C[C@H]1CN(CC2=CN(N=N2)C2=NC=C(C#N)C(C)=C2)C[C@H](N1)C1=C(C)C2=C(C=C1)C(=O)OC2 Chemical compound C[C@H]1CN(CC2=CN(N=N2)C2=NC=C(C#N)C(C)=C2)C[C@H](N1)C1=C(C)C2=C(C=C1)C(=O)OC2 ORMLUKIMTLUHOK-NYHFZMIOSA-N 0.000 claims 1
- MUHMXPXEQNABGA-GKVSMKOHSA-N C[C@H]1CN(C[C@H](N1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=CC(=NC=1)C1=CC(=NC=C1)N1C(OCC1)=O Chemical compound C[C@H]1CN(C[C@H](N1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=CC(=NC=1)C1=CC(=NC=C1)N1C(OCC1)=O MUHMXPXEQNABGA-GKVSMKOHSA-N 0.000 claims 1
- HGJPMQLHVXHPCS-AOMKIAJQSA-N C[C@H]1CN(C[C@H](N1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=CC=CC(=N1)N1C(OCC1)=O Chemical compound C[C@H]1CN(C[C@H](N1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=CC=CC(=N1)N1C(OCC1)=O HGJPMQLHVXHPCS-AOMKIAJQSA-N 0.000 claims 1
- 206010007556 Cardiac failure acute Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- NGDYSQUSYYDZDM-LADGPHEKSA-N Cc1cc(nc(C)c1C#N)-n1cc(CN2CC[C@@H](O)[C@@H](C2)c2ccc3C(=O)OCc3c2C)cn1 Chemical compound Cc1cc(nc(C)c1C#N)-n1cc(CN2CC[C@@H](O)[C@@H](C2)c2ccc3C(=O)OCc3c2C)cn1 NGDYSQUSYYDZDM-LADGPHEKSA-N 0.000 claims 1
- RSBLZQHQMSKBPM-UHFFFAOYSA-N Cc1cc(ncc1C#N)-n1cc(CN2CC(CO)NC(C2)c2ccc3C(=O)OCc3c2C)cn1 Chemical compound Cc1cc(ncc1C#N)-n1cc(CN2CC(CO)NC(C2)c2ccc3C(=O)OCc3c2C)cn1 RSBLZQHQMSKBPM-UHFFFAOYSA-N 0.000 claims 1
- 208000003037 Diastolic Heart Failure Diseases 0.000 claims 1
- MMPHZSMWKTZISM-IBGZPJMESA-N FC(C1=C(N=CN1C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C)F Chemical compound FC(C1=C(N=CN1C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C)F MMPHZSMWKTZISM-IBGZPJMESA-N 0.000 claims 1
- BIVHEAOINYINAP-FPTDNZKUSA-N FC(C1=CC=C(C=N1)N1C=NC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C)F Chemical compound FC(C1=CC=C(C=N1)N1C=NC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C)F BIVHEAOINYINAP-FPTDNZKUSA-N 0.000 claims 1
- MPFYGDZPNNWKPK-FPTDNZKUSA-N FC(C1=NC=CC(=C1)N1N=CC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C)F Chemical compound FC(C1=NC=CC(=C1)N1N=CC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C)F MPFYGDZPNNWKPK-FPTDNZKUSA-N 0.000 claims 1
- SUTWGXUUIICEDR-IBGZPJMESA-N FC(C1=NN(C=C1C#N)C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)F Chemical compound FC(C1=NN(C=C1C#N)C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)F SUTWGXUUIICEDR-IBGZPJMESA-N 0.000 claims 1
- XQSMXAKFSIJUNB-NRFANRHFSA-N FC(C1=NN(C=C1CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C1=NC=C(C#N)C(=C1)C)F Chemical compound FC(C1=NN(C=C1CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)C1=NC=C(C#N)C(=C1)C)F XQSMXAKFSIJUNB-NRFANRHFSA-N 0.000 claims 1
- OKSIUDGHUIVVOO-UHFFFAOYSA-N FC(C1CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)F Chemical compound FC(C1CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)F OKSIUDGHUIVVOO-UHFFFAOYSA-N 0.000 claims 1
- XRWLEUCHCKTJHZ-IBGZPJMESA-N FC(C=1N=CN(C=1)C1=CC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)F Chemical compound FC(C=1N=CN(C=1)C1=CC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)F XRWLEUCHCKTJHZ-IBGZPJMESA-N 0.000 claims 1
- IVDOCPODRUOHKW-FQEVSTJZSA-N FC(OC1=NN(C=C1C#N)C1=NC=C(C=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)F Chemical compound FC(OC1=NN(C=C1C#N)C1=NC=C(C=C1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C)F IVDOCPODRUOHKW-FQEVSTJZSA-N 0.000 claims 1
- UBYSMWIRDSTDOD-QKKBWIMNSA-N FC1(OC2=C(O1)C=CC(=C2)N1C=NC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C)F Chemical compound FC1(OC2=C(O1)C=CC(=C2)N1C=NC(=C1)CN1C[C@H](N[C@H](C1)C)C=1C(=C2COC(C2=CC=1)=O)C)F UBYSMWIRDSTDOD-QKKBWIMNSA-N 0.000 claims 1
- 206010016803 Fluid overload Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- IVIGLRATQJSZAS-SFHVURJKSA-N N1(N=CN=C1)C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound N1(N=CN=C1)C1=NC=C(C=N1)CN1C[C@H](NCC1)C=1C(=C2COC(C2=CC=1)=O)C IVIGLRATQJSZAS-SFHVURJKSA-N 0.000 claims 1
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 1
- RYSLQZXGAQBSII-UHFFFAOYSA-N OC(C)C1CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)OC Chemical compound OC(C)C1CN(CC(N1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)OC RYSLQZXGAQBSII-UHFFFAOYSA-N 0.000 claims 1
- GPYHTOIUANPAIA-UHFFFAOYSA-N OC1(C(CN(CC1)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C)C Chemical compound OC1(C(CN(CC1)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C)C GPYHTOIUANPAIA-UHFFFAOYSA-N 0.000 claims 1
- YLRNNRJLIUQDSL-UHFFFAOYSA-N OCC1CN(CC(C1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C Chemical compound OCC1CN(CC(C1)C=1C(=C2COC(C2=CC=1)=O)C)CC=1C=NN(C=1)C1=NC=C(C#N)C(=C1)C YLRNNRJLIUQDSL-UHFFFAOYSA-N 0.000 claims 1
- FJTXPLFAYVIITG-NYHFZMIOSA-N ON1[C@H](CN(C[C@H]1C=1C(=C2COC(C2=CC=1)=O)C)CC1=NN(N=C1)C1=NC=C(C#N)C(=C1)C)C Chemical compound ON1[C@H](CN(C[C@H]1C=1C(=C2COC(C2=CC=1)=O)C)CC1=NN(N=C1)C1=NC=C(C#N)C(=C1)C)C FJTXPLFAYVIITG-NYHFZMIOSA-N 0.000 claims 1
- JBHJLLWYOPAMGA-GBXCKJPGSA-N O[C@H]1[C@@H](CN(CC1)CC1=CC(=NO1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound O[C@H]1[C@@H](CN(CC1)CC1=CC(=NO1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C JBHJLLWYOPAMGA-GBXCKJPGSA-N 0.000 claims 1
- IOHMVZJPKKFEHK-NZQKXSOJSA-N O[C@H]1[C@@H](CN(CC1)CC1=CN=C(S1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound O[C@H]1[C@@H](CN(CC1)CC1=CN=C(S1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C IOHMVZJPKKFEHK-NZQKXSOJSA-N 0.000 claims 1
- CNSPVMNZIHIASO-JTHBVZDNSA-N O[C@H]1[C@@H](CN(CC1)CC=1N(C(N(C=1)C1=NC=C(C#N)C(=C1)C)=O)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound O[C@H]1[C@@H](CN(CC1)CC=1N(C(N(C=1)C1=NC=C(C#N)C(=C1)C)=O)C)C=1C(=C2COC(C2=CC=1)=O)C CNSPVMNZIHIASO-JTHBVZDNSA-N 0.000 claims 1
- BJZVIIIUYGTJFH-RBBKRZOGSA-N O[C@H]1[C@@H](CN(CC1)CC=1N(C(N(C=1)C1=NC=C(C#N)C(=C1)OC)=O)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound O[C@H]1[C@@H](CN(CC1)CC=1N(C(N(C=1)C1=NC=C(C#N)C(=C1)OC)=O)C)C=1C(=C2COC(C2=CC=1)=O)C BJZVIIIUYGTJFH-RBBKRZOGSA-N 0.000 claims 1
- TXNTXUZQDFCQJR-LADGPHEKSA-N O[C@H]1[C@@H](CN(CC1)CC=1N=CN(C=1)C1=CC(=C(C#N)C=C1)OC)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound O[C@H]1[C@@H](CN(CC1)CC=1N=CN(C=1)C1=CC(=C(C#N)C=C1)OC)C=1C(=C2COC(C2=CC=1)=O)C TXNTXUZQDFCQJR-LADGPHEKSA-N 0.000 claims 1
- BADFANFNQWCIEE-JTHBVZDNSA-N O[C@H]1[C@@H](CN(CC1)CC=1N=CN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C Chemical compound O[C@H]1[C@@H](CN(CC1)CC=1N=CN(C=1)C1=NC=C(C#N)C(=C1)C)C=1C(=C2COC(C2=CC=1)=O)C BADFANFNQWCIEE-JTHBVZDNSA-N 0.000 claims 1
- 206010030113 Oedema Diseases 0.000 claims 1
- 208000033626 Renal failure acute Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000008253 Systolic Heart Failure Diseases 0.000 claims 1
- RSBLZQHQMSKBPM-KLTYLHELSA-N [2H]C([2H])(O)C1CN(CC2=CN(N=C2)C2=NC=C(C#N)C(C)=C2)CC(N1)C1=CC=C2C(=O)OCC2=C1C Chemical compound [2H]C([2H])(O)C1CN(CC2=CN(N=C2)C2=NC=C(C#N)C(C)=C2)CC(N1)C1=CC=C2C(=O)OCC2=C1C RSBLZQHQMSKBPM-KLTYLHELSA-N 0.000 claims 1
- 201000011040 acute kidney failure Diseases 0.000 claims 1
- 208000012998 acute renal failure Diseases 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- NZRSUHUWIOYOOH-UHFFFAOYSA-N piperidin-4-yl n-methylcarbamate Chemical compound CNC(=O)OC1CCNCC1 NZRSUHUWIOYOOH-UHFFFAOYSA-N 0.000 claims 1
- 230000002980 postoperative effect Effects 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 230000002685 pulmonary effect Effects 0.000 claims 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- SCWJDDWMVZOMOY-LEWJYISDSA-N Cc1cc(-[n]2nc(CN(C3)C[C@H](N)N[C@@H]3c(cc3)c(C)c(CO4)c3C4=O)cn2)ncc1C#N Chemical compound Cc1cc(-[n]2nc(CN(C3)C[C@H](N)N[C@@H]3c(cc3)c(C)c(CO4)c3C4=O)cn2)ncc1C#N SCWJDDWMVZOMOY-LEWJYISDSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022090971A JP7406592B2 (ja) | 2017-06-01 | 2022-06-03 | 置換窒素含有化合物 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201711019293 | 2017-06-01 | ||
| IN201711019293 | 2017-06-01 | ||
| IN201811004486 | 2018-02-06 | ||
| IN201811004486 | 2018-02-06 | ||
| PCT/US2018/035270 WO2018222795A1 (en) | 2017-06-01 | 2018-05-31 | Substituted nitrogen containing compounds |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022090971A Division JP7406592B2 (ja) | 2017-06-01 | 2022-06-03 | 置換窒素含有化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020522490A JP2020522490A (ja) | 2020-07-30 |
| JP2020522490A5 true JP2020522490A5 (enExample) | 2021-06-10 |
| JP7084946B2 JP7084946B2 (ja) | 2022-06-15 |
Family
ID=62685190
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019566121A Active JP7084946B2 (ja) | 2017-06-01 | 2018-05-31 | 置換窒素含有化合物 |
| JP2022090971A Active JP7406592B2 (ja) | 2017-06-01 | 2022-06-03 | 置換窒素含有化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022090971A Active JP7406592B2 (ja) | 2017-06-01 | 2022-06-03 | 置換窒素含有化合物 |
Country Status (27)
| Country | Link |
|---|---|
| US (6) | US10501449B2 (enExample) |
| EP (2) | EP3929194B1 (enExample) |
| JP (2) | JP7084946B2 (enExample) |
| KR (1) | KR102655318B1 (enExample) |
| CN (1) | CN110678463B (enExample) |
| AU (1) | AU2018275552B2 (enExample) |
| CA (1) | CA3065309A1 (enExample) |
| CL (1) | CL2019003486A1 (enExample) |
| CO (1) | CO2019013589A2 (enExample) |
| CY (1) | CY1124479T1 (enExample) |
| DK (1) | DK3630752T3 (enExample) |
| ES (2) | ES2981919T3 (enExample) |
| HR (1) | HRP20211262T1 (enExample) |
| HU (1) | HUE056142T2 (enExample) |
| IL (1) | IL271036B2 (enExample) |
| LT (1) | LT3630752T (enExample) |
| MX (1) | MX389581B (enExample) |
| MY (1) | MY201325A (enExample) |
| PE (1) | PE20200386A1 (enExample) |
| PL (1) | PL3630752T3 (enExample) |
| PT (1) | PT3630752T (enExample) |
| RS (1) | RS62277B1 (enExample) |
| SI (1) | SI3630752T1 (enExample) |
| SM (1) | SMT202100512T1 (enExample) |
| TW (1) | TWI791527B (enExample) |
| WO (1) | WO2018222795A1 (enExample) |
| ZA (1) | ZA201908488B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2902527T3 (es) * | 2016-11-03 | 2022-03-28 | Bristol Myers Squibb Co | Derivados biciclo heterocíclicos sustituidos, útiles como inhibidores del canal ROMK |
| MY201325A (en) * | 2017-06-01 | 2024-02-16 | Bristol Myers Squibb Co | Substituted nitrogen containing compounds |
| BR112022011917A2 (pt) | 2019-12-20 | 2022-09-06 | Tenaya Therapeutics Inc | Fluoroalquil-oxadiazois e seus usos |
| KR20230007453A (ko) * | 2020-05-06 | 2023-01-12 | 바이오하벤 테라퓨틱스 리미티드 | 베르디퍼스타트의 제조 과정 |
| MX2023012875A (es) | 2021-05-04 | 2024-01-12 | Tenaya Therapeutics Inc | Inhibidores 2-fluoro alquil-l,3,4-oxadiazol-5-il-tiazol de hdac6 para su uso en el tratamiento de enfermedades metabólicas y hfpef. |
| CN114957222B (zh) * | 2022-05-31 | 2023-08-15 | 内蒙古民族大学 | 化合物及其制备方法和用途 |
| CN114907323B (zh) * | 2022-05-31 | 2023-08-15 | 内蒙古民族大学 | 喹喔啉酮类化合物及其制备方法和应用 |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000078716A1 (en) | 1999-06-24 | 2000-12-28 | Toray Industries, Inc. | α1B-ADRENERGIC RECEPTOR ANTAGONISTS |
| US6921763B2 (en) | 1999-09-17 | 2005-07-26 | Abbott Laboratories | Pyrazolopyrimidines as therapeutic agents |
| KR100882179B1 (ko) | 2001-06-20 | 2009-02-06 | 깃세이 야쿠힌 고교 가부시키가이샤 | 함질소 복소환 유도체, 그것을 함유하는 의약 조성물, 그의약 용도 및 그 제조 중간체 |
| AU2003223467B2 (en) | 2002-04-08 | 2007-10-04 | Merck Sharp & Dohme Corp. | Inhibitors of Akt activity |
| CA2481229C (en) | 2002-04-08 | 2010-09-21 | Merck & Co., Inc. | Substituted pyrazine inhibitors of akt |
| KR20070036149A (ko) | 2004-07-16 | 2007-04-02 | 얀센 파마슈티카 엔.브이. | 이량체 피페리딘 유도체 |
| MX2007006109A (es) | 2004-12-01 | 2007-10-04 | Devgen Nv | Derivados de tiazol sustituidos en 5-carboxamido que interactuan con canales de iones, en particular con canales ionicos de la familia de kv. |
| SE0403171D0 (sv) | 2004-12-23 | 2004-12-23 | Astrazeneca Ab | New compounds |
| CN102014927A (zh) | 2008-03-06 | 2011-04-13 | 安纳考尔医药公司 | 作为抗炎药的含硼的小分子 |
| US8673920B2 (en) | 2009-05-06 | 2014-03-18 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| BRPI1012852A2 (pt) | 2009-05-15 | 2018-06-19 | Novartis Ag | derivados de benzoxazolona como inibidores da sintase de aldoesterona |
| DE102009022896A1 (de) | 2009-05-27 | 2010-12-02 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Piperidine |
| GB0913342D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | Compounds - 801 |
| EP2536690B1 (en) | 2010-02-19 | 2018-08-08 | Arizona Board Of Regents | Multifunctional radical quenchers and their use |
| CA2812088A1 (en) | 2010-09-14 | 2012-03-22 | Exelixis, Inc. | Phtalazine derivatives as jak1 inhibitors |
| WO2012058116A1 (en) | 2010-10-27 | 2012-05-03 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US9056859B2 (en) | 2010-10-29 | 2015-06-16 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| KR20140052034A (ko) | 2011-08-19 | 2014-05-02 | 머크 샤프 앤드 돔 코포레이션 | 신장 외수질 칼륨 채널의 억제제 |
| EP2755656B1 (en) | 2011-09-16 | 2016-09-07 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2013062900A1 (en) | 2011-10-25 | 2013-05-02 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2013062892A1 (en) | 2011-10-25 | 2013-05-02 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2773206B1 (en) | 2011-10-31 | 2018-02-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US9493474B2 (en) | 2011-10-31 | 2016-11-15 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2013066714A1 (en) | 2011-10-31 | 2013-05-10 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US9206199B2 (en) * | 2011-12-16 | 2015-12-08 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| AR092031A1 (es) | 2012-07-26 | 2015-03-18 | Merck Sharp & Dohme | Inhibidores del canal de potasio medular externo renal |
| WO2014015495A1 (en) | 2012-07-26 | 2014-01-30 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US9777002B2 (en) | 2012-11-29 | 2017-10-03 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US9573961B2 (en) | 2012-12-19 | 2017-02-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US8889671B2 (en) | 2013-01-23 | 2014-11-18 | Astrazeneca Ab | Compounds and methods for treating bacterial infections |
| US9604998B2 (en) | 2013-02-18 | 2017-03-28 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2014150132A1 (en) | 2013-03-15 | 2014-09-25 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP3027625B1 (en) | 2013-07-31 | 2018-05-30 | Merck Sharp & Dohme Corp. | Spiro-fused derivatives of piperidine useful for the treatment of inter alia hypertension and acute or chronic heart failure |
| LT3055302T (lt) | 2013-10-11 | 2019-03-12 | F. Hoffmann-La Roche Ag | Pakeistieji heterocikliniai sulfonamidiniai junginiai, tinkami naudoti kaip trpa1 moduliatoriai |
| WO2015065866A1 (en) * | 2013-10-31 | 2015-05-07 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP3083573B1 (en) | 2013-12-18 | 2024-08-07 | Merck Sharp & Dohme LLC | Inhibitors of the renal outer medullary potassium channel |
| WO2015090579A1 (en) | 2013-12-18 | 2015-06-25 | Grünenthal GmbH | Pyrazolyl-based carboxamides iv |
| WO2015096035A1 (en) | 2013-12-24 | 2015-07-02 | Merck Sharp & Dohme Corp. | Inhibitors of renal outer medullary potassium channel |
| WO2015103756A1 (en) | 2014-01-09 | 2015-07-16 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2016008064A1 (en) | 2014-07-14 | 2016-01-21 | Merck Sharp & Dohme Corp. | Inhibitors of renal outer medullary potassium channel |
| KR20170021358A (ko) | 2014-07-14 | 2017-02-27 | 머크 샤프 앤드 돔 코포레이션 | 신장 외수질성 칼륨 채널의 억제제 |
| WO2016060941A1 (en) | 2014-10-14 | 2016-04-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2016065582A1 (en) | 2014-10-30 | 2016-05-06 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2016065602A1 (en) | 2014-10-31 | 2016-05-06 | Merck Sharp & Dohme Corp. | Inhibitors of renal outer medullary potassium channel |
| EP3212617A1 (en) | 2014-10-31 | 2017-09-06 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2016065603A1 (en) | 2014-10-31 | 2016-05-06 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| JP6736816B2 (ja) | 2014-12-08 | 2020-08-05 | ジエンス ヘンルイ メデイシンカンパニー リミテッドＪｉａｎｇｓｕ Ｈｅｎｇｒｕｉ Ｍｅｄｉｃｉｎｅ Ｃｏ．，Ｌｔｄ． | ピリジンカルボキサミド誘導体、それらの製造方法およびそれらの医薬用途 |
| CN105693706B (zh) | 2014-12-10 | 2019-11-22 | 江苏恒瑞医药股份有限公司 | 异苯并呋喃酮类衍生物、其制备方法及其在医药上的应用 |
| EP3250204B1 (en) | 2015-01-29 | 2019-10-30 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2016127358A1 (en) | 2015-02-12 | 2016-08-18 | Merck Sharp & Dohme Corp. | Inhibitors of renal outer medullary potassium channel |
| WO2017001991A1 (en) | 2015-06-29 | 2017-01-05 | Crystalmorphix Technologies Pvt. Ltd | Cocrystals of trigonelline |
| MX381425B (es) | 2016-04-20 | 2025-03-12 | Bristol Myers Squibb Co | Compuestos heterociclicos biciclicos sustituidos. |
| ES2902527T3 (es) | 2016-11-03 | 2022-03-28 | Bristol Myers Squibb Co | Derivados biciclo heterocíclicos sustituidos, útiles como inhibidores del canal ROMK |
| MY201325A (en) * | 2017-06-01 | 2024-02-16 | Bristol Myers Squibb Co | Substituted nitrogen containing compounds |
-
2018
- 2018-05-31 MY MYPI2019006969A patent/MY201325A/en unknown
- 2018-05-31 WO PCT/US2018/035270 patent/WO2018222795A1/en not_active Ceased
- 2018-05-31 PL PL18733083T patent/PL3630752T3/pl unknown
- 2018-05-31 RS RS20211080A patent/RS62277B1/sr unknown
- 2018-05-31 EP EP21175085.6A patent/EP3929194B1/en active Active
- 2018-05-31 LT LTEPPCT/US2018/035270T patent/LT3630752T/lt unknown
- 2018-05-31 PE PE2019002492A patent/PE20200386A1/es unknown
- 2018-05-31 HR HRP20211262TT patent/HRP20211262T1/hr unknown
- 2018-05-31 JP JP2019566121A patent/JP7084946B2/ja active Active
- 2018-05-31 TW TW107118600A patent/TWI791527B/zh not_active IP Right Cessation
- 2018-05-31 US US15/993,683 patent/US10501449B2/en not_active Ceased
- 2018-05-31 AU AU2018275552A patent/AU2018275552B2/en active Active
- 2018-05-31 ES ES21175085T patent/ES2981919T3/es active Active
- 2018-05-31 HU HUE18733083A patent/HUE056142T2/hu unknown
- 2018-05-31 KR KR1020197038642A patent/KR102655318B1/ko active Active
- 2018-05-31 MX MX2019014411A patent/MX389581B/es unknown
- 2018-05-31 CA CA3065309A patent/CA3065309A1/en active Pending
- 2018-05-31 ES ES18733083T patent/ES2885243T3/es active Active
- 2018-05-31 EP EP18733083.2A patent/EP3630752B1/en active Active
- 2018-05-31 CN CN201880035414.4A patent/CN110678463B/zh active Active
- 2018-05-31 SM SM20210512T patent/SMT202100512T1/it unknown
- 2018-05-31 PT PT187330832T patent/PT3630752T/pt unknown
- 2018-05-31 DK DK18733083.2T patent/DK3630752T3/da active
- 2018-05-31 SI SI201830362T patent/SI3630752T1/sl unknown
-
2019
- 2019-11-11 US US16/679,435 patent/US20200109135A1/en not_active Abandoned
- 2019-11-28 IL IL271036A patent/IL271036B2/en unknown
- 2019-11-28 CL CL2019003486A patent/CL2019003486A1/es unknown
- 2019-11-29 CO CONC2019/0013589A patent/CO2019013589A2/es unknown
- 2019-12-19 ZA ZA2019/08488A patent/ZA201908488B/en unknown
-
2020
- 2020-07-14 US US16/928,079 patent/US20200339550A1/en not_active Abandoned
-
2021
- 2021-02-23 US US17/183,286 patent/USRE49700E1/en active Active
- 2021-09-08 CY CY20211100795T patent/CY1124479T1/el unknown
-
2022
- 2022-06-03 JP JP2022090971A patent/JP7406592B2/ja active Active
- 2022-10-05 US US17/960,199 patent/US20230124468A1/en not_active Abandoned
-
2024
- 2024-05-09 US US18/659,052 patent/US20240327390A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2020522490A5 (enExample) | ||
| HRP20211262T1 (hr) | Supstituirani spojevi koji sadrže dušik | |
| RU2012146246A (ru) | Антибактериальные производные изохинолин-3-илмочевины | |
| RU2396269C2 (ru) | Производные гетероарилзамещенного пиперидина в качестве ингибиторов печеночной карнитин пальмитоилтрансферазы (l-cpt1) | |
| JP2011503166A5 (enExample) | ||
| JP2016519096A5 (enExample) | ||
| JP2021502356A5 (enExample) | ||
| IL263511A (en) | 1h-pyrazolo[4,3-b]pyridines as pde1 inhibitors | |
| RU2019118623A (ru) | Пирролопиримидины в качестве потенциаторов мвтр | |
| ME02437B (me) | Disupstituirani oktahidropirolo[3,4-c]piroli kao modulatori oreksin receptora | |
| IL258577A (en) | 2,4-dihydroxy-nicotinamides as apj agonists | |
| RU2010137300A (ru) | Модуляторы бета-амилоида | |
| RU2016141646A (ru) | Ингибиторы trka киназы, основанные на них композиции и способы | |
| RU2014152625A (ru) | Конденсированные с гетероарилкетонами азадекалины - модуляторы глюкокортикоидных рецепторов | |
| CN115697991A (zh) | 哌嗪环状脲 | |
| IL310330A (en) | Compounds for the treatment of pain, in particular neuropathic pain, and/or other diseases or disorders that are associated with at2r and/or at2r mediated signaling | |
| RU2019123319A (ru) | Пиразолопиримидины и способы их применения | |
| JP2020516672A5 (enExample) | ||
| HRP20211784T1 (hr) | Kombinacijski tretmani koji se sastoje od primjene 1h-pirazolo[4,3-b]piridina | |
| JPWO2021124172A5 (enExample) | ||
| RU2020119080A (ru) | Виды комбинированного лечения, предусматривающего введение 1h-пиразолo[4,3-b]пиридинов | |
| US20240383875A1 (en) | Benzimidazole Pyridine Derivatives | |
| KR20160144493A (ko) | 인돌린-2-온 및 1,3-다이하이드로-피롤로[3,2-c]피리딘-2-온 유도체 | |
| RU2024120925A (ru) | Новые пиридиновые производные бензимидазола | |
| KR20190070985A (ko) | RORc 조절제로서의 피리다진 유도체 |