JP2015526395A5 - - Google Patents
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- Publication number
- JP2015526395A5 JP2015526395A5 JP2015518523A JP2015518523A JP2015526395A5 JP 2015526395 A5 JP2015526395 A5 JP 2015526395A5 JP 2015518523 A JP2015518523 A JP 2015518523A JP 2015518523 A JP2015518523 A JP 2015518523A JP 2015526395 A5 JP2015526395 A5 JP 2015526395A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- pyrido
- methyl
- methoxybenzyl
- 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 -C 3-6 cycloalkyl Chemical group 0.000 claims 48
- 125000000217 alkyl group Chemical group 0.000 claims 42
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 36
- 150000001875 compounds Chemical class 0.000 claims 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 24
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 125000003342 alkenyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 239000001301 oxygen Substances 0.000 claims 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000006413 ring segment Chemical group 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 239000011593 sulfur Substances 0.000 claims 6
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 3
- 125000004001 thioalkyl group Chemical group 0.000 claims 3
- ZZAKLGGGMWORRT-UHFFFAOYSA-N 1-methylsulfonylpiperazine Chemical compound CS(=O)(=O)N1CCNCC1 ZZAKLGGGMWORRT-UHFFFAOYSA-N 0.000 claims 2
- GQQUTUGEEPKFRZ-UHFFFAOYSA-N 11-(1,3-dihydroisoindol-2-ylmethyl)-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3nc(CN4Cc5ccccc5C4)ccc3c3ncnn3c2=O)cc1 GQQUTUGEEPKFRZ-UHFFFAOYSA-N 0.000 claims 2
- MPVDRAKOTXIBJJ-UHFFFAOYSA-N 11-(anilinomethyl)-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3nc(CNc4ccccc4)ccc3c3ncnn3c2=O)cc1 MPVDRAKOTXIBJJ-UHFFFAOYSA-N 0.000 claims 2
- ZXBACYKCVPRMSH-UHFFFAOYSA-N 11-[(benzylamino)methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3nc(CNCc4ccccc4)ccc3c3ncnn3c2=O)cc1 ZXBACYKCVPRMSH-UHFFFAOYSA-N 0.000 claims 2
- OJDJJJPIMOMVEH-IYBDPMFKSA-N 11-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3nc(CN4C[C@H](C)O[C@H](C)C4)ccc3c3ncnn3c2=O)cc1 OJDJJJPIMOMVEH-IYBDPMFKSA-N 0.000 claims 2
- RYCKTYYTERTYPB-UHFFFAOYSA-N 11-[[cyclopropyl(methyl)amino]methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3nc(CN(C)C4CC4)ccc3c3ncnn3c2=O)cc1 RYCKTYYTERTYPB-UHFFFAOYSA-N 0.000 claims 2
- ISMBZMHCWIWETK-UHFFFAOYSA-N 11-bromo-8-[(4-methoxyphenyl)methyl]-3,5,6,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3cc(Br)cnc3c3ncnn3c2=O)cc1 ISMBZMHCWIWETK-UHFFFAOYSA-N 0.000 claims 2
- DFVHSRFVDBIKMF-UHFFFAOYSA-O 12-(2-aminoethyl)-8-[(4-methoxyphenyl)methyl]-5,6,8,10-tetraza-3-azoniatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CCN)cc3c3[nH+]cnn3c2=O)cc1 DFVHSRFVDBIKMF-UHFFFAOYSA-O 0.000 claims 2
- MESDOLJXWPQUMC-UHFFFAOYSA-N 12-(3,4-dimethoxyphenyl)-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(C=3C=C(OC)C(OC)=CC=3)=CN=C21 MESDOLJXWPQUMC-UHFFFAOYSA-N 0.000 claims 2
- HEOXVOHBJCXVJD-UHFFFAOYSA-N 12-[(2,2-dimethylmorpholin-4-yl)methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(CN3CC(C)(C)OCC3)=CN=C21 HEOXVOHBJCXVJD-UHFFFAOYSA-N 0.000 claims 2
- GGZJEUMXVWUFQM-UHFFFAOYSA-N 12-[(2,5-dimethylmorpholin-4-yl)methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(CN3C(COC(C)C3)C)=CN=C21 GGZJEUMXVWUFQM-UHFFFAOYSA-N 0.000 claims 2
- ROTNPJUKGYGBRP-UHFFFAOYSA-N 12-[(2-ethylmorpholin-4-yl)methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound CCC1CN(Cc2cnc3n(Cc4ccc(OC)cc4)c(=O)n4ncnc4c3c2)CCO1 ROTNPJUKGYGBRP-UHFFFAOYSA-N 0.000 claims 2
- UTJXRFRESOHGQF-GASCZTMLSA-N 12-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(cc3c3ncnn3c2=O)N2C[C@H](C)O[C@H](C)C2)cc1 UTJXRFRESOHGQF-GASCZTMLSA-N 0.000 claims 2
- JICMCVOTVHSRFC-UHFFFAOYSA-N 12-[(3,3-dimethylmorpholin-4-yl)methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(CN3C(COCC3)(C)C)=CN=C21 JICMCVOTVHSRFC-UHFFFAOYSA-N 0.000 claims 2
- FFUNSPVGUJTVFD-UHFFFAOYSA-N 12-[(4-acetyl-1,4-diazepan-1-yl)methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCCN(CC4)C(C)=O)cc3c3ncnn3c2=O)cc1 FFUNSPVGUJTVFD-UHFFFAOYSA-N 0.000 claims 2
- FMVZEKVXCWVZJT-UHFFFAOYSA-N 12-[(dimethylamino)methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN(C)C)cc3c3ncnn3c2=O)cc1 FMVZEKVXCWVZJT-UHFFFAOYSA-N 0.000 claims 2
- CRJRMKHOQXXRGM-GWTOYCKXSA-N 12-[2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-1-fluoroethyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(C(F)CN3C[C@@H](C)O[C@@H](C)C3)=CN=C21 CRJRMKHOQXXRGM-GWTOYCKXSA-N 0.000 claims 2
- XRLXBBTWVBYRLL-GWTOYCKXSA-N 12-[2-[(2S,6R)-2,6-dimethylmorpholin-4-yl]-1-hydroxyethyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(C(O)CN3C[C@@H](C)O[C@@H](C)C3)=CN=C21 XRLXBBTWVBYRLL-GWTOYCKXSA-N 0.000 claims 2
- OWTXAFQDORRHDF-UHFFFAOYSA-N 12-[3-(dimethylamino)propyl-methylamino]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(cc3c3ncnn3c2=O)N(C)CCCN(C)C)cc1 OWTXAFQDORRHDF-UHFFFAOYSA-N 0.000 claims 2
- SQCVSKGSFIKMHS-UHFFFAOYSA-N 12-[3-(dimethylamino)pyrrolidin-1-yl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(cc3c3ncnn3c2=O)N2CCC(C2)N(C)C)cc1 SQCVSKGSFIKMHS-UHFFFAOYSA-N 0.000 claims 2
- CEYLCNFAPOMWHU-UHFFFAOYSA-N 12-[4-(2-methoxyethyl)piperazin-1-yl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COCCN1CCN(CC1)c1cnc2n(Cc3ccc(OC)cc3)c(=O)n3ncnc3c2c1 CEYLCNFAPOMWHU-UHFFFAOYSA-N 0.000 claims 2
- NPXNBDQDCHRUQN-UHFFFAOYSA-N 12-[4-(dimethylamino)piperidin-1-yl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(cc3c3ncnn3c2=O)N2CCC(CC2)N(C)C)cc1 NPXNBDQDCHRUQN-UHFFFAOYSA-N 0.000 claims 2
- MOMKKADZWIOJTM-IYBDPMFKSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(1-methylindazol-6-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc5cnn(C)c5c4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 MOMKKADZWIOJTM-IYBDPMFKSA-N 0.000 claims 2
- TXOAOIWNMWCENE-TXEJJXNPSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(2,3,5,6-tetrafluoro-4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1c(F)c(F)c(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(F)c1F TXOAOIWNMWCENE-TXEJJXNPSA-N 0.000 claims 2
- NHQYZSMOAOPZQO-TXEJJXNPSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(2,3,5,6-tetrafluoro-4-methylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4c(F)c(F)c(C)c(F)c4F)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 NHQYZSMOAOPZQO-TXEJJXNPSA-N 0.000 claims 2
- VJQPAZHLWZAFOO-GASCZTMLSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(2-fluoro-4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound FC1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(CN3C[C@@H](C)O[C@@H](C)C3)=CN=C21 VJQPAZHLWZAFOO-GASCZTMLSA-N 0.000 claims 2
- QEMIDHGPYIGXPQ-HDICACEKSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(3,4-dimethylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound CC=1C=C(CN2C(N3C(C4=C2N=CC(=C4)CN4C[C@H](O[C@H](C4)C)C)=NC=N3)=O)C=CC1C QEMIDHGPYIGXPQ-HDICACEKSA-N 0.000 claims 2
- WUSQIEMTTSJENQ-GASCZTMLSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(3-iodophenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@@H]1O[C@@H](CN(C1)CC1=CC=2C=3N(C(N(C2N=C1)CC1=CC(=CC=C1)I)=O)N=CN3)C WUSQIEMTTSJENQ-GASCZTMLSA-N 0.000 claims 2
- JEOBQVKBQGYJBK-CALCHBBNSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-ethoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound CCOc1ccc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)cc1 JEOBQVKBQGYJBK-CALCHBBNSA-N 0.000 claims 2
- HLFVJZZTVRKXCW-CALCHBBNSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-ethynylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(cc4)C#C)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 HLFVJZZTVRKXCW-CALCHBBNSA-N 0.000 claims 2
- MXMQBDLBIHEJBR-CALCHBBNSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-fluoro-3,5-dimethylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4cc(C)c(F)c(C)c4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 MXMQBDLBIHEJBR-CALCHBBNSA-N 0.000 claims 2
- HIXOBBPAKXJFRS-GASCZTMLSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-fluoro-3-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1cc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)ccc1F HIXOBBPAKXJFRS-GASCZTMLSA-N 0.000 claims 2
- JIOGEEMSIGIKTN-GASCZTMLSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-fluorophenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(F)cc4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 JIOGEEMSIGIKTN-GASCZTMLSA-N 0.000 claims 2
- YLLBTWWTWUARNT-CALCHBBNSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-methoxy-3-methylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)cc1C YLLBTWWTWUARNT-CALCHBBNSA-N 0.000 claims 2
- GEOSPJPGBQGSBN-IYBDPMFKSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-methylsulfanylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@@H]1O[C@@H](CN(C1)CC1=CC=2C=3N(C(N(C2N=C1)CC1=CC=C(C=C1)SC)=O)N=CN3)C GEOSPJPGBQGSBN-IYBDPMFKSA-N 0.000 claims 2
- GKVJFHCCQRERJU-GASCZTMLSA-N 12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[[4-(trifluoromethyl)phenyl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1O[C@H](CN(C1)CC1=CC=2C=3N(C(N(C2N=C1)CC1=CC=C(C=C1)C(F)(F)F)=O)N=CN3)C GKVJFHCCQRERJU-GASCZTMLSA-N 0.000 claims 2
- QSTHNCPIFKNYTR-BETUJISGSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(2,3,4-trifluorophenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(F)c(F)c4F)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 QSTHNCPIFKNYTR-BETUJISGSA-N 0.000 claims 2
- KYTBYIFEUAGUIE-BETUJISGSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(2,4,5-trifluorophenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4cc(F)c(F)cc4F)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 KYTBYIFEUAGUIE-BETUJISGSA-N 0.000 claims 2
- VNLJKXMOUUHLQN-IYBDPMFKSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(2-fluoro-4-methylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(C)cc4F)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 VNLJKXMOUUHLQN-IYBDPMFKSA-N 0.000 claims 2
- OBAUDFMPXAXZLK-BETUJISGSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(3,4,5-trifluorophenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4cc(F)c(F)c(F)c4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 OBAUDFMPXAXZLK-BETUJISGSA-N 0.000 claims 2
- YBLGMSFAJBTICA-IYBDPMFKSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(3,4,5-trimethoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1cc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)cc(OC)c1OC YBLGMSFAJBTICA-IYBDPMFKSA-N 0.000 claims 2
- XTHIZDDAZRUJFU-GASCZTMLSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(3-fluoro-4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)cc1F XTHIZDDAZRUJFU-GASCZTMLSA-N 0.000 claims 2
- CHVOHLHKAAOOIB-GASCZTMLSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-ethoxy-2,3-difluorophenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound CCOc1ccc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(F)c1F CHVOHLHKAAOOIB-GASCZTMLSA-N 0.000 claims 2
- HXTAMDSRCICWKT-GASCZTMLSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-ethoxy-3,5-difluorophenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound CCOc1c(F)cc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)cc1F HXTAMDSRCICWKT-GASCZTMLSA-N 0.000 claims 2
- FNUMHYHTUKOSFV-IYBDPMFKSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-fluoro-3-methylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(F)c(C)c4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 FNUMHYHTUKOSFV-IYBDPMFKSA-N 0.000 claims 2
- LCKJIXTZQWYXSS-GASCZTMLSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-iodophenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(I)cc4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 LCKJIXTZQWYXSS-GASCZTMLSA-N 0.000 claims 2
- PEBZZMCYBQJHDB-IYBDPMFKSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-methylsulfonylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@@H]1O[C@@H](CN(C1)CC1=CC=2C=3N(C(N(C2N=C1)CC1=CC=C(C=C1)S(=O)(=O)C)=O)N=CN3)C PEBZZMCYBQJHDB-IYBDPMFKSA-N 0.000 claims 2
- TZKCCZSECNJFRH-HDICACEKSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-pyrazol-1-ylphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(cc4)-n4cccn4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 TZKCCZSECNJFRH-HDICACEKSA-N 0.000 claims 2
- YUNHYIFVGFFLNH-GASCZTMLSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[[2-(trifluoromethylsulfanyl)phenyl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@@H]1O[C@@H](CN(C1)CC1=CC=2C=3N(C(N(C2N=C1)CC1=C(C=CC=C1)SC(F)(F)F)=O)N=CN3)C YUNHYIFVGFFLNH-GASCZTMLSA-N 0.000 claims 2
- KKIGPQAYYKYIOW-HDICACEKSA-N 12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[[4-(2-oxopyrrolidin-1-yl)phenyl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(cc4)N4CCCC4=O)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 KKIGPQAYYKYIOW-HDICACEKSA-N 0.000 claims 2
- BROSYLQGBXNCAX-IYBDPMFKSA-N 12-[[(3R,5S)-3,5-dimethylpiperazin-1-yl]methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(C[C@H](N1)C)CC1=CC=2C=3N(C(N(C2N=C1)CC1=CC=C(C=C1)OC)=O)N=CN3 BROSYLQGBXNCAX-IYBDPMFKSA-N 0.000 claims 2
- QEVBPFDWXOADFA-UHFFFAOYSA-N 12-[[2-methoxyethyl(methyl)amino]methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COCCN(C)Cc1cnc2n(Cc3ccc(OC)cc3)c(=O)n3ncnc3c2c1 QEVBPFDWXOADFA-UHFFFAOYSA-N 0.000 claims 2
- OEHMCZKSPFEAIZ-UHFFFAOYSA-N 12-[[2-methoxyethyl(propan-2-yl)amino]methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COCCN(Cc1cnc2n(Cc3ccc(OC)cc3)c(=O)n3ncnc3c2c1)C(C)C OEHMCZKSPFEAIZ-UHFFFAOYSA-N 0.000 claims 2
- XYRMLJFVWXNVCJ-UHFFFAOYSA-N 12-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COCCN1CCN(Cc2cnc3n(Cc4ccc(OC)cc4)c(=O)n4ncnc4c3c2)CC1 XYRMLJFVWXNVCJ-UHFFFAOYSA-N 0.000 claims 2
- RSIWAONLJPNADZ-UHFFFAOYSA-N 12-[[cyclohexyl(methyl)amino]methyl]-8-[(4-methoxyphenyl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN(C)C4CCCCC4)cc3c3ncnn3c2=O)cc1 RSIWAONLJPNADZ-UHFFFAOYSA-N 0.000 claims 2
- KVALAQLQHWSFSE-UHFFFAOYSA-N 3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound N=1C=NN2C(=NC3=C(C2=1)C=CC=N3)O KVALAQLQHWSFSE-UHFFFAOYSA-N 0.000 claims 2
- KCIQCRPLNSJZTK-IYBDPMFKSA-N 3-[[12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-7-oxo-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-8-yl]methyl]benzonitrile Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4cccc(c4)C#N)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 KCIQCRPLNSJZTK-IYBDPMFKSA-N 0.000 claims 2
- YTQVQRLJTMHHHS-IYBDPMFKSA-N 4-[[12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-7-oxo-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-8-yl]methyl]benzonitrile Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(cc4)C#N)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 YTQVQRLJTMHHHS-IYBDPMFKSA-N 0.000 claims 2
- LATSDBVMSPZMSP-UHFFFAOYSA-N 4-[[8-[(4-methoxyphenyl)methyl]-7-oxo-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-12-yl]methyl]-N,N-dimethylpiperazine-1-sulfonamide Chemical compound COc1ccc(Cn2c3ncc(CN4CCN(CC4)S(=O)(=O)N(C)C)cc3c3ncnn3c2=O)cc1 LATSDBVMSPZMSP-UHFFFAOYSA-N 0.000 claims 2
- GTUJCYWYRJAYEU-UHFFFAOYSA-N 6-(4-methoxybenzyl)-9-((methoxymethoxy)methyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5 (6h)-one Chemical compound O=C1N2N=CN=C2C2=CC(COCOC)=CN=C2N1CC1=CC=C(OC)C=C1 GTUJCYWYRJAYEU-UHFFFAOYSA-N 0.000 claims 2
- RACYNVRAYIFZLQ-UHFFFAOYSA-N 6-(4-methoxybenzyl)-9-(1-ethoxyvinyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6h)-one Chemical compound O=C1N2N=CN=C2C2=CC(C(=C)OCC)=CN=C2N1CC1=CC=C(OC)C=C1 RACYNVRAYIFZLQ-UHFFFAOYSA-N 0.000 claims 2
- MODSISUJBUONHU-UHFFFAOYSA-N 6-(4-methoxybenzyl)-9-(2,2,2-trifluoro-1-hydroxyethyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6h)-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(C(O)C(F)(F)F)=CN=C21 MODSISUJBUONHU-UHFFFAOYSA-N 0.000 claims 2
- NXFSHDPRZJMZIU-UHFFFAOYSA-N 6-(4-methoxybenzyl)-9-(3-methyl-6-oxopyridazin-1(6h)-yl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6h)-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(N3C(C=CC(C)=N3)=O)=CN=C21 NXFSHDPRZJMZIU-UHFFFAOYSA-N 0.000 claims 2
- ADFZINMFQBKMEL-UHFFFAOYSA-N 7-[[8-[(4-methoxyphenyl)methyl]-7-oxo-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-12-yl]methyl]-5,6,8,8a-tetrahydro-1H-[1,3]oxazolo[3,4-a]pyrazin-3-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCN5C(COC5=O)C4)cc3c3ncnn3c2=O)cc1 ADFZINMFQBKMEL-UHFFFAOYSA-N 0.000 claims 2
- LTQSPCAZRXRLNY-GASCZTMLSA-N 8-(1,3-benzodioxol-5-ylmethyl)-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc5OCOc5c4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 LTQSPCAZRXRLNY-GASCZTMLSA-N 0.000 claims 2
- LRXPDMTXCSZSJB-UHFFFAOYSA-N 8-(dimethoxymethyl)-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6h)-one Chemical compound C12=NC(C(OC)OC)=CC=C2C2=NC=NN2C(=O)N1CC1=CC=C(OC)C=C1 LRXPDMTXCSZSJB-UHFFFAOYSA-N 0.000 claims 2
- SSHQJRQUDVRGNB-OKILXGFUSA-N 8-[(2,3-dichlorophenyl)methyl]-12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound ClC1=C(CN2C(N3C(C4=C2N=CC(=C4)CN4C[C@H](O[C@H](C4)C)C)=NC=N3)=O)C=CC=C1Cl SSHQJRQUDVRGNB-OKILXGFUSA-N 0.000 claims 2
- VQHMIIBPKSRCSF-UHFFFAOYSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-12-(1,4-oxazepan-4-ylmethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCCOCC4)cc3c3ncnn3c2=O)c(F)c1F VQHMIIBPKSRCSF-UHFFFAOYSA-N 0.000 claims 2
- PISBCCLFCWJQDQ-UHFFFAOYSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-12-(piperidin-1-ylmethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCCCC4)cc3c3ncnn3c2=O)c(F)c1F PISBCCLFCWJQDQ-UHFFFAOYSA-N 0.000 claims 2
- VAXUKEJGLOOIHW-UHFFFAOYSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-12-[(3-hydroxyazetidin-1-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CC(O)C4)cc3c3ncnn3c2=O)c(F)c1F VAXUKEJGLOOIHW-UHFFFAOYSA-N 0.000 claims 2
- ZETTVIVNFFMGQU-UHFFFAOYSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-12-[(3-methylmorpholin-4-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCOCC4C)cc3c3ncnn3c2=O)c(F)c1F ZETTVIVNFFMGQU-UHFFFAOYSA-N 0.000 claims 2
- OZHOWCFITKRGQE-UHFFFAOYSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-12-[(4-propan-2-ylpiperazin-1-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCN(CC4)C(C)C)cc3c3ncnn3c2=O)c(F)c1F OZHOWCFITKRGQE-UHFFFAOYSA-N 0.000 claims 2
- XAFXFCHYOPWWLL-OKILXGFUSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(F)c1F XAFXFCHYOPWWLL-OKILXGFUSA-N 0.000 claims 2
- RCVRJEFCNJORPL-GASCZTMLSA-N 8-[(2,3-difluoro-4-methylphenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound FC1=C(CN2C(N3C(C4=C2N=CC(=C4)CN4C[C@H](O[C@H](C4)C)C)=NC=N3)=O)C=CC(=C1F)C RCVRJEFCNJORPL-GASCZTMLSA-N 0.000 claims 2
- RAAICHKDDOVPRP-BETUJISGSA-N 8-[(2,4-dichloro-5-fluorophenyl)methyl]-12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound ClC1=C(CN2C(N3C(C4=C2N=CC(=C4)CN4C[C@H](O[C@H](C4)C)C)=NC=N3)=O)C=C(C(=C1)Cl)F RAAICHKDDOVPRP-BETUJISGSA-N 0.000 claims 2
- FGMVGZPNBOCHPN-OKILXGFUSA-N 8-[(2,4-dichlorophenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(Cl)cc4Cl)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 FGMVGZPNBOCHPN-OKILXGFUSA-N 0.000 claims 2
- PFQFWNAYJVERRX-OKILXGFUSA-N 8-[(2,5-difluorophenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4cc(F)ccc4F)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 PFQFWNAYJVERRX-OKILXGFUSA-N 0.000 claims 2
- GAQHJHTYRQGLFF-OKILXGFUSA-N 8-[(2,6-difluoro-4-methoxyphenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1cc(F)c(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(F)c1 GAQHJHTYRQGLFF-OKILXGFUSA-N 0.000 claims 2
- ZTHWXAYFVLBMJZ-GASCZTMLSA-N 8-[(2-bromo-4-methoxyphenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(Br)c1 ZTHWXAYFVLBMJZ-GASCZTMLSA-N 0.000 claims 2
- UDIODENKEXPQHC-BETUJISGSA-N 8-[(2-chloro-4,5-difluorophenyl)methyl]-12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4cc(F)c(F)cc4Cl)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 UDIODENKEXPQHC-BETUJISGSA-N 0.000 claims 2
- QLKLJDICPFAPQV-OKILXGFUSA-N 8-[(2-chloro-4-fluorophenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(F)cc4Cl)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 QLKLJDICPFAPQV-OKILXGFUSA-N 0.000 claims 2
- UNHOIQPBHXBAFN-GASCZTMLSA-N 8-[(2-chloro-4-methoxyphenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(Cl)c1 UNHOIQPBHXBAFN-GASCZTMLSA-N 0.000 claims 2
- MFWHBWVVAPARCL-GASCZTMLSA-N 8-[(2-chloro-4-methylsulfonylphenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound ClC1=C(CN2C(N3C(C4=C2N=CC(=C4)CN4C[C@@H](O[C@@H](C4)C)C)=NC=N3)=O)C=CC(=C1)S(=O)(=O)C MFWHBWVVAPARCL-GASCZTMLSA-N 0.000 claims 2
- DZYJMOZEZDREJB-OKILXGFUSA-N 8-[(3,4-dichlorophenyl)methyl]-12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1[C@@H](C)O[C@@H](C)CN1CC1=CN=C(N(CC=2C=C(Cl)C(Cl)=CC=2)C(=O)N2C3=NC=N2)C3=C1 DZYJMOZEZDREJB-OKILXGFUSA-N 0.000 claims 2
- WPTOWKRTBCTNSG-OKILXGFUSA-N 8-[(3,4-difluorophenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(F)c(F)c4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 WPTOWKRTBCTNSG-OKILXGFUSA-N 0.000 claims 2
- STUAGBZGADGNQC-IYBDPMFKSA-N 8-[(3,4-dimethoxyphenyl)methyl]-12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)cc1OC STUAGBZGADGNQC-IYBDPMFKSA-N 0.000 claims 2
- IXJRJXQQXNWVDX-OKILXGFUSA-N 8-[(3,5-difluoro-4-methoxyphenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound FC=1C=C(CN2C(N3C(C4=C2N=CC(=C4)CN4C[C@@H](O[C@@H](C4)C)C)=NC=N3)=O)C=C(C1OC)F IXJRJXQQXNWVDX-OKILXGFUSA-N 0.000 claims 2
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- LISPBBLYPRJSSU-OKILXGFUSA-N 8-[(3-bromo-4-fluorophenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound BrC=1C=C(CN2C(N3C(C4=C2N=CC(=C4)CN4C[C@@H](O[C@@H](C4)C)C)=NC=N3)=O)C=CC1F LISPBBLYPRJSSU-OKILXGFUSA-N 0.000 claims 2
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- NGOFGHZBALSNRW-OKILXGFUSA-N 8-[(3-chloro-5-fluorophenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4cc(F)cc(Cl)c4)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 NGOFGHZBALSNRW-OKILXGFUSA-N 0.000 claims 2
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- PAHYKUNLNZIYOM-OKILXGFUSA-N 8-[(4-chloro-2-fluorophenyl)methyl]-12-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C[C@H]1CN(Cc2cnc3n(Cc4ccc(Cl)cc4F)c(=O)n4ncnc4c3c2)C[C@@H](C)O1 PAHYKUNLNZIYOM-OKILXGFUSA-N 0.000 claims 2
- XCHGWJNWOPKYGL-OKILXGFUSA-N 8-[(4-chloro-3-fluorophenyl)methyl]-12-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound ClC1=C(C=C(CN2C(N3C(C4=C2N=CC(=C4)CN4C[C@@H](O[C@@H](C4)C)C)=NC=N3)=O)C=C1)F XCHGWJNWOPKYGL-OKILXGFUSA-N 0.000 claims 2
- AEJKRJSFOUFJOZ-UHFFFAOYSA-N 8-[(4-chlorophenyl)methyl]-12-(morpholin-4-ylmethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound Clc1ccc(Cn2c3ncc(CN4CCOCC4)cc3c3ncnn3c2=O)cc1 AEJKRJSFOUFJOZ-UHFFFAOYSA-N 0.000 claims 2
- OSJOJUDRQZZHFH-UHFFFAOYSA-N 8-[(4-chlorophenyl)methyl]-12-(piperidin-1-ylmethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound ClC1=CC=C(CN2C(N3C(C4=C2N=CC(=C4)CN4CCCCC4)=NC=N3)=O)C=C1 OSJOJUDRQZZHFH-UHFFFAOYSA-N 0.000 claims 2
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- OWKQXHFZWKMQOI-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-(thiomorpholin-4-ylmethyl)-3,5,6,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COC1=CC=C(CN2C(N3C(C4=C2C=C(C=N4)CN4CCSCC4)=NC=N3)=O)C=C1 OWKQXHFZWKMQOI-UHFFFAOYSA-N 0.000 claims 2
- ICQOGBVNQIOWES-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-[(4-methylpiperazin-1-yl)methyl]-3,5,6,8,13-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3cc(CN4CCN(C)CC4)cnc3c3ncnn3c2=O)cc1 ICQOGBVNQIOWES-UHFFFAOYSA-N 0.000 claims 2
- BZYOQXACSWYWBF-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-[(4-methylsulfonylpiperazin-1-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3nc(CN4CCN(CC4)S(C)(=O)=O)ccc3c3ncnn3c2=O)cc1 BZYOQXACSWYWBF-UHFFFAOYSA-N 0.000 claims 2
- IWXQKCBDZHFJRI-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-[[(3-methyloxetan-3-yl)methylamino]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3nc(CNCC4(C)COC4)ccc3c3ncnn3c2=O)cc1 IWXQKCBDZHFJRI-UHFFFAOYSA-N 0.000 claims 2
- LQFDJAYETNZWPQ-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-[[methyl(oxolan-3-ylmethyl)amino]methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3nc(CN(C)CC4CCOC4)ccc3c3ncnn3c2=O)cc1 LQFDJAYETNZWPQ-UHFFFAOYSA-N 0.000 claims 2
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- QGSHILNYLICGPO-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-(2,2,2-trifluoro-1-morpholin-4-ylethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(C(N3CCOCC3)C(F)(F)F)=CN=C21 QGSHILNYLICGPO-UHFFFAOYSA-N 0.000 claims 2
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- QJFJNPBHAZKFAP-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-(6-methoxypyridin-3-yl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(cc3c3ncnn3c2=O)-c2ccc(OC)nc2)cc1 QJFJNPBHAZKFAP-UHFFFAOYSA-N 0.000 claims 2
- VVKZFXAYICSEDA-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-(8-oxa-3-azabicyclo[3.2.1]octan-3-ylmethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CC5CCC(C4)O5)cc3c3ncnn3c2=O)cc1 VVKZFXAYICSEDA-UHFFFAOYSA-N 0.000 claims 2
- FMOQMSRLUIDKRK-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-(morpholin-4-ylmethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCOCC4)cc3c3ncnn3c2=O)cc1 FMOQMSRLUIDKRK-UHFFFAOYSA-N 0.000 claims 2
- ZRFAKRASZDZMDB-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-(piperazin-1-ylmethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(CN3CCNCC3)=CN=C21 ZRFAKRASZDZMDB-UHFFFAOYSA-N 0.000 claims 2
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- FYMUURGHCBUQTA-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-(thiomorpholin-4-ylmethyl)-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COC1=CC=C(CN2C(N3C(C4=C2N=CC(=C4)CN4CCSCC4)=NC=N3)=O)C=C1 FYMUURGHCBUQTA-UHFFFAOYSA-N 0.000 claims 2
- DRPGXSKMJNNINK-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-[(1-methyl-8-oxa-1,2-diazaspiro[4.5]decan-2-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCC5(CCOCC5)N4C)cc3c3ncnn3c2=O)cc1 DRPGXSKMJNNINK-UHFFFAOYSA-N 0.000 claims 2
- UJZIAYUIWVKELD-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-[(2,2,6,6-tetrafluoromorpholin-4-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COC1=CC=C(CN2C(N3C(C4=C2N=CC(=C4)CN4CC(OC(C4)(F)F)(F)F)=NC=N3)=O)C=C1 UJZIAYUIWVKELD-UHFFFAOYSA-N 0.000 claims 2
- AITPEKNDNRONAJ-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-[(2-methylmorpholin-4-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=CC(CN3CC(C)OCC3)=CN=C21 AITPEKNDNRONAJ-UHFFFAOYSA-N 0.000 claims 2
- YRKXMRFGXRVPAK-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-[(3-methylmorpholin-4-yl)methyl]-3,5,6,8,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,10,12-pentaen-7-one Chemical compound COc1ccc(Cn2c3ncc(CN4CCOCC4C)cc3c3ncnn3c2=O)cc1 YRKXMRFGXRVPAK-UHFFFAOYSA-N 0.000 claims 2
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| JP6396230B2 (ja) * | 2014-01-27 | 2018-09-26 | 株式会社ポーラファルマ | 使用時泡状を呈する外用医薬組成物 |
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| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| WO2017046603A1 (en) * | 2015-09-18 | 2017-03-23 | Redx Pharma Plc | Antibacterial compounds and new uses thereof |
| TWI609870B (zh) * | 2016-02-12 | 2018-01-01 | 美國禮來大藥廠 | Pde1抑制劑 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
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| CN109843884B (zh) | 2016-10-18 | 2022-03-04 | H.隆德贝克有限公司 | 作为pde1抑制剂的咪唑并吡嗪酮、吡唑并嘧啶酮和吡唑并吡啶酮 |
| KR20190077349A (ko) | 2016-10-28 | 2019-07-03 | 하. 룬드벡 아크티에셀스카브 | 이미다조피라지논의 투여를 포함하는 병용 치료 |
| EP3532064B1 (en) | 2016-10-28 | 2020-07-29 | H. Lundbeck A/S | Combination treatments comprising imidazopyrazinones for the treatment of psychiatric and/or cognitive disorders |
| KR102590848B1 (ko) | 2016-12-28 | 2023-10-19 | 다트 뉴로사이언스, 엘엘씨 | Pde2 억제제로서 치환된 피라졸로피리미디논 화합물 |
| CN110392686A (zh) * | 2016-12-30 | 2019-10-29 | 频率治疗公司 | 1h-吡咯-2,5-二酮化合物以及使用它们来诱导干/祖支持细胞自我更新的方法 |
| EP3585392A1 (en) * | 2017-02-23 | 2020-01-01 | Boehringer Ingelheim International GmbH | New medical use of compound iii |
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| JP7254078B2 (ja) | 2017-11-27 | 2023-04-07 | ダート・ニューロサイエンス・エルエルシー | Ｐｄｅ１阻害剤としての置換フラノピリミジン化合物 |
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