JP2019515911A5 - - Google Patents
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- Publication number
- JP2019515911A5 JP2019515911A5 JP2018555138A JP2018555138A JP2019515911A5 JP 2019515911 A5 JP2019515911 A5 JP 2019515911A5 JP 2018555138 A JP2018555138 A JP 2018555138A JP 2018555138 A JP2018555138 A JP 2018555138A JP 2019515911 A5 JP2019515911 A5 JP 2019515911A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridinyl
- oxo
- dihydroisobenzofuran
- pyrimidin
- 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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- -1 1,2,3,4-tetrahydro-1,5-naphthyridinyl Chemical group 0.000 claims 120
- 125000000217 alkyl group Chemical group 0.000 claims 31
- 229910052799 carbon Inorganic materials 0.000 claims 29
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 27
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 20
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 18
- 125000003118 aryl group Chemical group 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000004076 pyridyl group Chemical group 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 8
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 7
- 125000001041 indolyl group Chemical group 0.000 claims 7
- 125000005466 alkylenyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 125000005605 benzo group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 2
- QRRLRJLHVTVIEF-UHFFFAOYSA-N 2,3-dihydro-1h-indole-4-carbonitrile Chemical compound N#CC1=CC=CC2=C1CCN2 QRRLRJLHVTVIEF-UHFFFAOYSA-N 0.000 claims 2
- FVLKLTUAMHIPMA-UHFFFAOYSA-N 2-fluoro-4-[[6-[2-hydroxy-1-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1C(CO)N1CCC2=NC(NC3=CC(F)=C(C=C3)C#N)=NC=C2C1 FVLKLTUAMHIPMA-UHFFFAOYSA-N 0.000 claims 2
- GVJUMYIQSNFBQS-UHFFFAOYSA-N 2-fluoro-4-[[7-(hydroxymethyl)-6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1CN1CC2=CN=C(NC3=CC(F)=C(C=C3)C#N)N=C2CC1CO GVJUMYIQSNFBQS-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- GWMGSCQFRVADLH-UHFFFAOYSA-N 1-[2-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]indole-4-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1CN1CCc2cc(ccc2C1)-n1ccc2c(cccc12)C#N GWMGSCQFRVADLH-UHFFFAOYSA-N 0.000 claims 1
- PDKKASJXYCTVJV-UHFFFAOYSA-N 1-[6-[(1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indazole-5-carbonitrile Chemical compound O=C1OCC2=CC(CN3CCC4=NC(=NC=C4C3)N3N=CC4=C3C=CC(=C4)C#N)=CC=C12 PDKKASJXYCTVJV-UHFFFAOYSA-N 0.000 claims 1
- AMRKKIOKNDHAAI-UHFFFAOYSA-N 1-[6-[(1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]pyrrolo[2,3-b]pyridine-5-carbonitrile Chemical compound O=C1OCC2=CC(CN3CCC4=NC(=NC=C4C3)N3C=CC4=C3N=CC(=C4)C#N)=CC=C12 AMRKKIOKNDHAAI-UHFFFAOYSA-N 0.000 claims 1
- IPOZVXUKHKCERA-UHFFFAOYSA-N 1-[6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]benzimidazole-4-carbonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1CN1CCC2=NC(=NC=C2C1)N1C=NC2=C(C=CC=C12)C#N IPOZVXUKHKCERA-UHFFFAOYSA-N 0.000 claims 1
- IWHBKFHZBGUWGY-UHFFFAOYSA-N 1-[6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indazole-5-carbonitrile Chemical compound CC1=C2COC(C2=CC=C1CN1CC2=C(N=C(N=C2)N2N=CC3=CC(=CC=C23)C#N)CC1)=O IWHBKFHZBGUWGY-UHFFFAOYSA-N 0.000 claims 1
- WLKXNCOLWKVLRL-UHFFFAOYSA-N 1-[6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indole-3-carbonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1CN1CCC2=NC(=NC=C2C1)N1C=C(C#N)C2=CC=CC=C12 WLKXNCOLWKVLRL-UHFFFAOYSA-N 0.000 claims 1
- BLIQFEPEZYBZBO-UHFFFAOYSA-N 1-[6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indole-4-carbonitrile Chemical compound CC1=C2COC(C2=CC=C1CN1CC2=C(N=C(N=C2)N2C=CC=3C(=CC=CC2=3)C#N)CC1)=O BLIQFEPEZYBZBO-UHFFFAOYSA-N 0.000 claims 1
- GZPQWTVXBRCISM-UHFFFAOYSA-N 1-[6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indole-5-carbonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1CN1CCC2=NC(=NC=C2C1)N1C=CC2=CC(=CC=C12)C#N GZPQWTVXBRCISM-UHFFFAOYSA-N 0.000 claims 1
- LBZWGZQUKNMBGH-UHFFFAOYSA-N 1-[6-[2-hydroxy-2-(1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indole-4-carbonitrile Chemical compound OC(CN1CCC2=NC(=NC=C2C1)N1C=CC2=C(C=CC=C12)C#N)C1=CC=C2C(=O)OCC2=C1 LBZWGZQUKNMBGH-UHFFFAOYSA-N 0.000 claims 1
- ORZWREBHCQKACJ-UHFFFAOYSA-N 1-[6-[2-hydroxy-2-(1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indole-5-carbonitrile Chemical compound OC(CN1CCC2=NC(=NC=C2C1)N1C=CC2=CC(=CC=C12)C#N)C1=CC=C2C(=O)OCC2=C1 ORZWREBHCQKACJ-UHFFFAOYSA-N 0.000 claims 1
- KRPZYOCENVANSW-UHFFFAOYSA-N 1-[6-[2-hydroxy-2-(3-methyl-2-oxo-1,3-benzoxazol-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indazole-4-carbonitrile Chemical compound Cn1c2cc(ccc2oc1=O)C(O)CN1CCc2nc(ncc2C1)-n1ncc2c(cccc12)C#N KRPZYOCENVANSW-UHFFFAOYSA-N 0.000 claims 1
- JIDBHWJYBZWRCF-UHFFFAOYSA-N 1-[6-[2-hydroxy-2-(3-methyl-2-oxo-1,3-benzoxazol-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]indole-4-carbonitrile Chemical compound Cn1c2cc(ccc2oc1=O)C(O)CN1CCc2nc(ncc2C1)-n1ccc2c(cccc12)C#N JIDBHWJYBZWRCF-UHFFFAOYSA-N 0.000 claims 1
- JVQZNHUFSUXMIY-UHFFFAOYSA-N 2-[[2-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]pyrimidine-5-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1CN1CCc2cc(Nc3ncc(cn3)C#N)ccc2C1 JVQZNHUFSUXMIY-UHFFFAOYSA-N 0.000 claims 1
- AGLNCQJYRXKZQZ-UHFFFAOYSA-N 2-fluoro-4-[[2-[(1-oxo-3H-2-benzofuran-5-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]benzonitrile Chemical compound Fc1cc(Nc2ccc3CN(Cc4ccc5C(=O)OCc5c4)CCc3c2)ccc1C#N AGLNCQJYRXKZQZ-UHFFFAOYSA-N 0.000 claims 1
- KCTGOULTUMTUQH-UHFFFAOYSA-N 2-fluoro-4-[[2-[(3-methyl-2-oxo-1,3-benzoxazol-5-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]benzonitrile Chemical compound Cn1c2cc(CN3CCc4cc(Nc5ccc(C#N)c(F)c5)ccc4C3)ccc2oc1=O KCTGOULTUMTUQH-UHFFFAOYSA-N 0.000 claims 1
- NVTHCTSQOSPGOP-UHFFFAOYSA-N 2-fluoro-4-[[2-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)NC=1C=C2CCN(CC2=CC=1)CC=1C(=C2COC(C2=CC=1)=O)C NVTHCTSQOSPGOP-UHFFFAOYSA-N 0.000 claims 1
- UWIVBVVTOQJPJS-UHFFFAOYSA-N 2-fluoro-4-[[2-[2-(1-oxo-3H-2-benzofuran-5-yl)ethyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)NC=1C=C2CCN(CC2=CC=1)CCC=1C=C2COC(C2=CC=1)=O UWIVBVVTOQJPJS-UHFFFAOYSA-N 0.000 claims 1
- JQZYMXJBCDAKNM-UHFFFAOYSA-N 2-fluoro-4-[[2-[2-hydroxy-1-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]benzonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1C(CO)N1CCC2=C(C1)C=CC(NC1=CC(F)=C(C=C1)C#N)=C2 JQZYMXJBCDAKNM-UHFFFAOYSA-N 0.000 claims 1
- NVQZFYZVDYXYJR-UHFFFAOYSA-N 2-fluoro-4-[[2-[2-hydroxy-2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]benzonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1C(O)CN1CCC2=C(C1)C=CC(NC1=CC(F)=C(C=C1)C#N)=C2 NVQZFYZVDYXYJR-UHFFFAOYSA-N 0.000 claims 1
- GKBAFSROZUWOIP-UHFFFAOYSA-N 2-fluoro-4-[[6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)NC=1N=CC2=C(N=1)CCN(C2)CC=1C(=C2COC(C2=CC=1)=O)C GKBAFSROZUWOIP-UHFFFAOYSA-N 0.000 claims 1
- IDENZEKIPQZNHF-UHFFFAOYSA-N 2-fluoro-4-[[6-[2-(1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-1,6-naphthyridin-2-yl]amino]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)NC1=NC=2CCN(CC=2C=C1)CCC=1C=C2COC(C2=CC=1)=O IDENZEKIPQZNHF-UHFFFAOYSA-N 0.000 claims 1
- BNTBWSVJRWLHIB-UHFFFAOYSA-N 2-fluoro-4-[[6-[2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)NC=1N=CC2=C(N=1)CCN(C2)CCC=1C(=C2COC(C2=CC=1)=O)C BNTBWSVJRWLHIB-UHFFFAOYSA-N 0.000 claims 1
- DGYWALNFLHLHFD-UHFFFAOYSA-N 2-fluoro-4-[[6-[2-hydroxy-2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1C(O)CN1CCC2=NC(NC3=CC(F)=C(C=C3)C#N)=NC=C2C1 DGYWALNFLHLHFD-UHFFFAOYSA-N 0.000 claims 1
- JYXCBDUVPKJTOB-UHFFFAOYSA-N 2-fluoro-4-[[[2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)-3,4-dihydro-1H-isoquinolin-6-yl]amino]methyl]benzonitrile Chemical compound FC1=C(C#N)C=CC(=C1)CNC=1C=C2CCN(CC2=CC=1)C=1C(=C2COC(C2=CC=1)=O)C JYXCBDUVPKJTOB-UHFFFAOYSA-N 0.000 claims 1
- LYUXFKKRHRUXQP-UHFFFAOYSA-N 2-fluoro-5-[[6-[(1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]benzonitrile Chemical compound FC1=C(C=C(NC2=NC=C3CN(CC4=CC=C5C(=O)OCC5=C4)CCC3=N2)C=C1)C#N LYUXFKKRHRUXQP-UHFFFAOYSA-N 0.000 claims 1
- SUQJLBWAYFXPDM-UHFFFAOYSA-N 2-fluoro-6-[[2-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]benzonitrile Chemical compound FC1=C(C#N)C(=CC=C1)NC=1C=C2CCN(CC2=CC=1)CC=1C(=C2COC(C2=CC=1)=O)C SUQJLBWAYFXPDM-UHFFFAOYSA-N 0.000 claims 1
- RXYGZBKQLWIWTM-UHFFFAOYSA-N 3-methyl-5-[[2-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]-1,3-benzoxazol-2-one Chemical compound Cc1c2COC(=O)c2ccc1CN1CCc2cc(Nc3ccc4oc(=O)n(C)c4c3)ccc2C1 RXYGZBKQLWIWTM-UHFFFAOYSA-N 0.000 claims 1
- CRRGLEQDTJJSEY-UHFFFAOYSA-N 3-methyl-5-[[6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]-1,3-benzoxazol-2-one Chemical compound Cc1c2COC(=O)c2ccc1CN1CCc2nc(Nc3ccc4oc(=O)n(C)c4c3)ncc2C1 CRRGLEQDTJJSEY-UHFFFAOYSA-N 0.000 claims 1
- WIZXASUWJRPUHL-UHFFFAOYSA-N 4-methyl-5-[[2-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]methyl]-3H-2-benzofuran-1-one Chemical compound CC1=C2COC(=O)C2=CC=C1CN1CCC2=NC(NC3=CC=C4C(=O)OCC4=C3C)=NC=C2C1 WIZXASUWJRPUHL-UHFFFAOYSA-N 0.000 claims 1
- WKGOYBKPASWBQA-UHFFFAOYSA-N 4-methyl-5-[[6-(pyrazolo[1,5-a]pyrimidin-5-ylamino)-3,4-dihydro-1H-isoquinolin-2-yl]methyl]-3H-2-benzofuran-1-one Chemical compound CC1=C2COC(=O)C2=CC=C1CN1CCC2=C(C1)C=CC(NC1=NC3=CC=NN3C=C1)=C2 WKGOYBKPASWBQA-UHFFFAOYSA-N 0.000 claims 1
- RMQYEUXSUAUCRB-UHFFFAOYSA-N 4-methyl-6-[[2-[(1-oxo-3H-2-benzofuran-5-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]amino]pyridine-3-carbonitrile Chemical compound Cc1cc(Nc2ccc3CN(Cc4ccc5C(=O)OCc5c4)CCc3c2)ncc1C#N RMQYEUXSUAUCRB-UHFFFAOYSA-N 0.000 claims 1
- KTYXUDCNLGSFSP-UHFFFAOYSA-N 4-methyl-6-[[6-[(4-methyl-1-oxo-3H-2-benzofuran-5-yl)methyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]pyridine-3-carbonitrile Chemical compound CC1=CC(=NC=C1C#N)NC=1N=CC2=C(N=1)CCN(C2)CC=1C(=C2COC(C2=CC=1)=O)C KTYXUDCNLGSFSP-UHFFFAOYSA-N 0.000 claims 1
- FTPBTOYQLJQZNK-UHFFFAOYSA-N 5-[1-hydroxy-2-(2-imidazo[4,5-b]pyridin-1-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1cnc2ncccc12 FTPBTOYQLJQZNK-UHFFFAOYSA-N 0.000 claims 1
- SBEUHKXMICFRQH-UHFFFAOYSA-N 5-[1-hydroxy-2-(2-imidazo[4,5-b]pyridin-3-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound N1=CN(C2=NC=CC=C21)C=1N=CC2=C(N=1)CCN(C2)CC(O)C=1C(=C2COC(C2=CC=1)=O)C SBEUHKXMICFRQH-UHFFFAOYSA-N 0.000 claims 1
- BJYLGMVVMFELAU-UHFFFAOYSA-N 5-[1-hydroxy-2-(2-imidazol-1-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1ccnc1 BJYLGMVVMFELAU-UHFFFAOYSA-N 0.000 claims 1
- BCRHBHIDTOBOGG-UHFFFAOYSA-N 5-[1-hydroxy-2-(2-pyrazolo[4,3-b]pyridin-1-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound CC1=C2COC(=O)C2=CC=C1C(O)CN1CCC2=NC(=NC=C2C1)N1N=CC2=C1C=CC=N2 BCRHBHIDTOBOGG-UHFFFAOYSA-N 0.000 claims 1
- ICZHCGFXYXPNLM-UHFFFAOYSA-N 5-[1-hydroxy-2-(2-pyrrolo[3,2-b]pyridin-1-yl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl)ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound N1(C=CC2=NC=CC=C21)C=1N=CC2=C(N=1)CCN(C2)CC(O)C=1C(=C2COC(C2=CC=1)=O)C ICZHCGFXYXPNLM-UHFFFAOYSA-N 0.000 claims 1
- XNYUWUJJVKPIEY-UHFFFAOYSA-N 5-[1-hydroxy-2-[2-(2-methylimidazol-1-yl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound Cc1nccn1-c1ncc2CN(CC(O)c3ccc4C(=O)OCc4c3C)CCc2n1 XNYUWUJJVKPIEY-UHFFFAOYSA-N 0.000 claims 1
- INVMSLQVRSOFGL-UHFFFAOYSA-N 5-[1-hydroxy-2-[2-(4-methylimidazol-1-yl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound Cc1cn(cn1)-c1ncc2CN(CC(O)c3ccc4C(=O)OCc4c3C)CCc2n1 INVMSLQVRSOFGL-UHFFFAOYSA-N 0.000 claims 1
- WNODRZMKCNUTFN-UHFFFAOYSA-N 5-[1-hydroxy-2-[2-(pyridin-3-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound CC1=C2COC(=O)C2=CC=C1C(O)CN1CCC2=NC(NC3=CC=CN=C3)=NC=C2C1 WNODRZMKCNUTFN-UHFFFAOYSA-N 0.000 claims 1
- FLLNKGVHZZKHRH-UHFFFAOYSA-N 5-[1-hydroxy-2-[2-[[5-(tetrazol-1-yl)pyridin-2-yl]amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]ethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(Nc3ccc(cn3)-n3cnnn3)ncc2C1 FLLNKGVHZZKHRH-UHFFFAOYSA-N 0.000 claims 1
- XUZNDUSSUUPYKR-UHFFFAOYSA-N 5-[2-[2-(benzimidazol-1-yl)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-1-hydroxyethyl]-4-methyl-3H-2-benzofuran-1-one Chemical compound N1(C=NC2=C1C=CC=C2)C=1N=CC2=C(N=1)CCN(C2)CC(O)C=1C(=C2COC(C2=CC=1)=O)C XUZNDUSSUUPYKR-UHFFFAOYSA-N 0.000 claims 1
- CIRJKSFPRPNSJQ-UHFFFAOYSA-N 5-[[6-[(1-oxo-3H-2-benzofuran-5-yl)amino]-3,4-dihydro-1H-isoquinolin-2-yl]methyl]-3H-2-benzofuran-1-one Chemical compound O=C1OCc2cc(CN3CCc4cc(Nc5ccc6C(=O)OCc6c5)ccc4C3)ccc12 CIRJKSFPRPNSJQ-UHFFFAOYSA-N 0.000 claims 1
- NJFASBUDFZPUDR-UHFFFAOYSA-N 5-[[6-[2-hydroxy-2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]-3-methyl-1,3-benzoxazol-2-one Chemical compound OC(CN1CC2=C(N=C(N=C2)NC=2C=CC3=C(N(C(O3)=O)C)C=2)CC1)C=1C(=C2COC(C2=CC=1)=O)C NJFASBUDFZPUDR-UHFFFAOYSA-N 0.000 claims 1
- GEKYCABZIWNYNW-UHFFFAOYSA-N 5-[[6-[2-hydroxy-2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]pyridine-3-carbonitrile Chemical compound OC(CN1CC2=C(N=C(N=C2)NC=2C=NC=C(C#N)C=2)CC1)C=1C(=C2COC(C2=CC=1)=O)C GEKYCABZIWNYNW-UHFFFAOYSA-N 0.000 claims 1
- LIHFQTHGIKPEAM-UHFFFAOYSA-N 6-[[6-[2-hydroxy-2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]amino]-4-methoxypyridine-3-carbonitrile Chemical compound OC(CN1CC2=C(N=C(N=C2)NC2=NC=C(C#N)C(=C2)OC)CC1)C=1C(=C2COC(C2=CC=1)=O)C LIHFQTHGIKPEAM-UHFFFAOYSA-N 0.000 claims 1
- 206010007556 Cardiac failure acute Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000003037 Diastolic Heart Failure Diseases 0.000 claims 1
- 206010016803 Fluid overload Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010029164 Nephrotic syndrome Diseases 0.000 claims 1
- 206010030113 Oedema Diseases 0.000 claims 1
- 208000004880 Polyuria Diseases 0.000 claims 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000008253 Systolic Heart Failure Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000029078 coronary artery disease Diseases 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
- 208000035475 disorder Diseases 0.000 claims 1
- 230000035619 diuresis Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- JGDIYNUWCNYOSF-UHFFFAOYSA-N ethyl 1-[6-[2-hydroxy-2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]pyrazolo[4,3-b]pyridine-6-carboxylate Chemical compound OC(CN1CC2=C(N=C(N=C2)N2N=CC3=NC=C(C=C32)C(=O)OCC)CC1)C=1C(=C2COC(C2=CC=1)=O)C JGDIYNUWCNYOSF-UHFFFAOYSA-N 0.000 claims 1
- 230000004217 heart function Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UZUQQSAODKZHRH-UHFFFAOYSA-N methyl 1-[6-[2-hydroxy-2-(4-methyl-1-oxo-3H-2-benzofuran-5-yl)ethyl]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-2-yl]pyrrolo[3,2-b]pyridine-6-carboxylate Chemical compound OC(CN1CC2=C(N=C(N=C2)N2C=CC3=NC=C(C=C32)C(=O)OC)CC1)C=1C(=C2COC(C2=CC=1)=O)C UZUQQSAODKZHRH-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000012495 positive regulation of renal sodium excretion Effects 0.000 claims 1
- 230000002980 postoperative effect Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 230000008085 renal dysfunction Effects 0.000 claims 1
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| EP3630752B1 (en) | 2017-06-01 | 2021-06-30 | Bristol-Myers Squibb Company | Substituted nitrogen containing compounds |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | Incyte Corporation | Bicyclic amines as cdk12 inhibitors |
| TW202527931A (zh) * | 2023-11-08 | 2025-07-16 | 美商奧科坦特公司 | 視紫質的藥理校正劑及其用途 |
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| DE102004020908A1 (de) | 2004-04-28 | 2005-11-17 | Grünenthal GmbH | Substituierte 5,6,7,8,-Tetrahydro-pyrido[4,3-d]pyrimidin-2-yl- und 5,6,7,8,-Tetrahydro-chinazolin-2-yl-Verbindungen |
| US8247556B2 (en) | 2005-10-21 | 2012-08-21 | Amgen Inc. | Method for preparing 6-substituted-7-aza-indoles |
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| ES2396160T3 (es) | 2006-12-14 | 2013-02-19 | Bayer Intellectual Property Gmbh | Derivados de DIHIDROPIRIDINA que utiliza como inhibidores de la proteina quinasa |
| US8673920B2 (en) * | 2009-05-06 | 2014-03-18 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2010130773A2 (en) | 2009-05-15 | 2010-11-18 | Novartis Ag | Benzoxazolone derivatives as aldosterone symthase inhibitors |
| DE102009022896A1 (de) | 2009-05-27 | 2010-12-02 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Piperidine |
| WO2012058116A1 (en) | 2010-10-27 | 2012-05-03 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2632464B1 (en) | 2010-10-29 | 2015-04-29 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| AU2012299227A1 (en) | 2011-08-19 | 2014-02-20 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| MX2014002208A (es) | 2011-08-25 | 2014-05-28 | Hoffmann La Roche | Inhibidores de serina/treonina quinasa. |
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| EP2790511B1 (en) | 2011-12-16 | 2016-09-14 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| BR112014015549A8 (pt) | 2011-12-22 | 2017-07-04 | Hoffmann La Roche | composto, método de inibição da atividade pak1, método para o tratamento, processo, composição, utilização de um composto e invenção |
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- 2017-04-19 WO PCT/US2017/028231 patent/WO2017184662A1/en not_active Ceased
- 2017-04-19 AU AU2017252546A patent/AU2017252546B2/en not_active Expired - Fee Related
- 2017-04-19 EA EA201892382A patent/EA037300B1/ru not_active IP Right Cessation
- 2017-04-19 KR KR1020187033099A patent/KR102417686B1/ko active Active
- 2017-04-19 US US16/094,288 patent/US10851108B2/en active Active
- 2017-04-19 CA CA3021335A patent/CA3021335A1/en not_active Abandoned
- 2017-04-19 JP JP2018555138A patent/JP6905993B2/ja active Active
- 2017-04-19 SG SG11201809173TA patent/SG11201809173TA/en unknown
- 2017-04-19 CN CN201780036983.6A patent/CN109311874B/zh active Active
- 2017-04-19 EP EP17733156.8A patent/EP3445762B1/en active Active
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2018
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