EA037300B1 - Замещенные бициклические гетероциклические соединения - Google Patents

Info

Publication number

EA037300B1

EA037300B1 EA201892382A EA201892382A EA037300B1 EA 037300 B1 EA037300 B1 EA 037300B1 EA 201892382 A EA201892382 A EA 201892382A EA 201892382 A EA201892382 A EA 201892382A EA 037300 B1 EA037300 B1 EA 037300B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methyl

oxo

dihydroisobenzofuran

pyrimidin

tetrahydropyrido

Prior art date

2016-04-20

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• 125000002618 bicyclic heterocycle group Chemical group 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 157
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 20
• -1 pyrazolo [3,4-b] pyridinyl Chemical group 0.000 claims description 163
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 57
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
• 238000011282 treatment Methods 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• 201000010099 disease Diseases 0.000 claims description 21
• 206010019280 Heart failures Diseases 0.000 claims description 20
• 208000004880 Polyuria Diseases 0.000 claims description 17
• 230000035619 diuresis Effects 0.000 claims description 17
• 230000012495 positive regulation of renal sodium excretion Effects 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 206010020772 Hypertension Diseases 0.000 claims description 12
• 239000003937 drug carrier Substances 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 8
• 230000004936 stimulating effect Effects 0.000 claims description 8
• WAZHBUDGOMPWHE-UHFFFAOYSA-N 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]indole-4-carbonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1C(O)CN1CCC2=NC(=NC=C2C1)N1C=CC2=C(C=CC=C12)C#N WAZHBUDGOMPWHE-UHFFFAOYSA-N 0.000 claims description 7
• 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 description 7
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 7
• 206010030113 Oedema Diseases 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 206010007556 Cardiac failure acute Diseases 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 6
• 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 description 5
• 208000009304 Acute Kidney Injury Diseases 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
• 208000003037 Diastolic Heart Failure Diseases 0.000 claims description 5
• 206010016803 Fluid overload Diseases 0.000 claims description 5
• 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims description 5
• 208000033626 Renal failure acute Diseases 0.000 claims description 5
• 208000008253 Systolic Heart Failure Diseases 0.000 claims description 5
• 201000011040 acute kidney failure Diseases 0.000 claims description 5
• 208000012998 acute renal failure Diseases 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 230000002980 postoperative effect Effects 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 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 description 4
• 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 description 4
• 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 description 4
• 208000006011 Stroke Diseases 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 208000029078 coronary artery disease Diseases 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 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 description 3
• 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 description 3
• JNMIAWKJJYWNSK-UHFFFAOYSA-N 1-[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]indole-3-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(CO)N1CCc2nc(ncc2C1)-n1cc(C#N)c2ccccc12 JNMIAWKJJYWNSK-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• LUIZMLDOODRRMC-UHFFFAOYSA-N 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]indole-3-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1cc(C#N)c2ccccc12 LUIZMLDOODRRMC-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 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 description 2
• GLRWGBAWAHKJKK-UHFFFAOYSA-N 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]indazole-5-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1ncc2cc(ccc12)C#N GLRWGBAWAHKJKK-UHFFFAOYSA-N 0.000 claims description 2
• CEUFGDDOMXCXFW-UHFFFAOYSA-N 1h-indole-4-carbonitrile Chemical compound N#CC1=CC=CC2=C1C=CN2 CEUFGDDOMXCXFW-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• HHXYDAHWEBSDSW-UHFFFAOYSA-N 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]-2,3-dihydroindole-4-carbonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1C(O)CN1CCC2=NC(=NC=C2C1)N1CCC2=C(C=CC=C12)C#N HHXYDAHWEBSDSW-UHFFFAOYSA-N 0.000 claims 2
• 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
• ZTSRRRHZBWHIBL-UHFFFAOYSA-N 1-[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]pyrrolo[2,3-b]pyridine-5-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(CO)N1CCc2nc(ncc2C1)-n1ccc2cc(cnc12)C#N ZTSRRRHZBWHIBL-UHFFFAOYSA-N 0.000 claims 1
• KGJJTPJVUUWODD-UHFFFAOYSA-N 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]indazole-3-carbonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1C(O)CN1CCC2=NC(=NC=C2C1)N1N=C(C#N)C2=C1C=CC=C2 KGJJTPJVUUWODD-UHFFFAOYSA-N 0.000 claims 1
• VMPKTXAZPLMKEZ-UHFFFAOYSA-N 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]indazole-4-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1ncc2c(cccc12)C#N VMPKTXAZPLMKEZ-UHFFFAOYSA-N 0.000 claims 1
• MXRFXISVFLCNTP-UHFFFAOYSA-N 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]indole-5-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1ccc2cc(ccc12)C#N MXRFXISVFLCNTP-UHFFFAOYSA-N 0.000 claims 1
• RJZDYOIOZJQMDN-UHFFFAOYSA-N 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]indole-6-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1ccc2ccc(cc12)C#N RJZDYOIOZJQMDN-UHFFFAOYSA-N 0.000 claims 1
• LUDUGDBSNJKSHW-UHFFFAOYSA-N 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]pyrazole-4-carbonitrile Chemical compound CC1=C2COC(=O)C2=CC=C1C(O)CN1CCC2=NC(=NC=C2C1)N1C=C(C=N1)C#N LUDUGDBSNJKSHW-UHFFFAOYSA-N 0.000 claims 1
• SILQPLHCOLKRLT-UHFFFAOYSA-N 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[3,4-b]pyridine-4-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1ncc2c(ccnc12)C#N SILQPLHCOLKRLT-UHFFFAOYSA-N 0.000 claims 1
• LJKATNFEHXBFAD-UHFFFAOYSA-N 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[3,4-c]pyridine-4-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1ncc2c(cncc12)C#N LJKATNFEHXBFAD-UHFFFAOYSA-N 0.000 claims 1
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• CECGVKIKMOJDBM-UHFFFAOYSA-N 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[2,3-b]pyridine-5-carbonitrile Chemical compound Cc1c2COC(=O)c2ccc1C(O)CN1CCc2nc(ncc2C1)-n1ccc2cc(cnc12)C#N CECGVKIKMOJDBM-UHFFFAOYSA-N 0.000 claims 1
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