JP2015509956A5 - - Google Patents
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- Publication number
- JP2015509956A5 JP2015509956A5 JP2014560007A JP2014560007A JP2015509956A5 JP 2015509956 A5 JP2015509956 A5 JP 2015509956A5 JP 2014560007 A JP2014560007 A JP 2014560007A JP 2014560007 A JP2014560007 A JP 2014560007A JP 2015509956 A5 JP2015509956 A5 JP 2015509956A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrano
- methylimidazo
- alkyl
- diazepan
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 37
- -1 dihydrochloride Chemical compound 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 208000002320 spinal muscular atrophy Diseases 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 210000005260 human cell Anatomy 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- NRGKFNDKBDBBGY-UHFFFAOYSA-N 1h-pyridin-2-one;hydrochloride Chemical compound Cl.O=C1C=CC=CN1 NRGKFNDKBDBBGY-UHFFFAOYSA-N 0.000 claims 1
- NZENVGLXUGPMPT-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-[4-(2,3-dihydroxypropyl)piperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC(O)CO)CCN1C1=CC=C(C=C(C=2SC3=CC=CC=C3N=2)C(=O)O2)C2=N1 NZENVGLXUGPMPT-UHFFFAOYSA-N 0.000 claims 1
- LKXICZSEPWWLQQ-UHFFFAOYSA-N 3-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-7-(4-methylpiperazin-1-yl)pyrano[3,2-c]pyridin-2-one Chemical compound C1CN(C)CCN1C(N=C1)=CC2=C1C=C(C=1N=C3SC(C)=CN3C=1)C(=O)O2 LKXICZSEPWWLQQ-UHFFFAOYSA-N 0.000 claims 1
- SSNAMLPQNIRTMQ-UHFFFAOYSA-N 3-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-7-piperazin-1-ylpyrano[3,2-c]pyridin-2-one;hydrochloride Chemical compound Cl.N1=C2SC(C)=CN2C=C1C(C(OC1=C2)=O)=CC1=CN=C2N1CCNCC1 SSNAMLPQNIRTMQ-UHFFFAOYSA-N 0.000 claims 1
- UPLNJBCPADXPTR-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-(4-methylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 UPLNJBCPADXPTR-UHFFFAOYSA-N 0.000 claims 1
- BJTWRFQYGSHACL-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-(4-propan-2-ylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C(C)C)CCN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 BJTWRFQYGSHACL-UHFFFAOYSA-N 0.000 claims 1
- INBDEJSJRQLYPF-QWHCGFSZSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 INBDEJSJRQLYPF-QWHCGFSZSA-N 0.000 claims 1
- KHTBWQBXLUSKSC-NWDGAFQWSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-[(2r,5s)-2,5-dimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN[C@@H](C)CN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 KHTBWQBXLUSKSC-NWDGAFQWSA-N 0.000 claims 1
- RFUOLDFXNKIEGC-BETUJISGSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-[(3r,5s)-3,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1[C@@H](C)N(C)[C@@H](C)CN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 RFUOLDFXNKIEGC-BETUJISGSA-N 0.000 claims 1
- ROAYKBBVDRJLKH-TXEJJXNPSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 ROAYKBBVDRJLKH-TXEJJXNPSA-N 0.000 claims 1
- SNCQHCWZEIVPHD-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-[4-(2,3-dihydroxypropyl)piperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC(O)CO)CCN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 SNCQHCWZEIVPHD-UHFFFAOYSA-N 0.000 claims 1
- YEEMOJGNZBIFLY-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-[4-(2-hydroxyethyl)piperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound ClC1=CC=CC2=C1N=C(S2)C1=CC=2C(=NC(=CC=2)N2CCN(CC2)CCO)OC1=O YEEMOJGNZBIFLY-UHFFFAOYSA-N 0.000 claims 1
- GFMPXGSGBRHPCR-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-[4-[(2-hydroxyphenyl)methyl]piperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound OC1=CC=CC=C1CN1CCN(C=2N=C3OC(=O)C(C=4SC5=CC=CC(Cl)=C5N=4)=CC3=CC=2)CC1 GFMPXGSGBRHPCR-UHFFFAOYSA-N 0.000 claims 1
- HRSKYOMHKBUZOR-UHFFFAOYSA-N 3-(4-methyl-1,3-thiazol-2-yl)-7-(4-propylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CCC)CCN1C1=CC=C(C=C(C=2SC=C(C)N=2)C(=O)O2)C2=N1 HRSKYOMHKBUZOR-UHFFFAOYSA-N 0.000 claims 1
- PMOVLNOABYLSBD-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(4-ethyl-1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC)CCCN1C1=CC=C(C=C(C=2N=C3C(C)=NC(C)=CN3C=2)C(=O)O2)C2=N1 PMOVLNOABYLSBD-UHFFFAOYSA-N 0.000 claims 1
- NNOVYROVMQTVAI-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(4-ethylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC)CCN1C1=CC=C(C=C(C=2N=C3C(C)=NC(C)=CN3C=2)C(=O)O2)C2=N1 NNOVYROVMQTVAI-UHFFFAOYSA-N 0.000 claims 1
- DJSZNVQUJXGOOW-UHFFFAOYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-(4-methyl-1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCCN1C1=CC=C(C=C(C=2N=C3C(C)=NC(C)=CN3C=2)C(=O)O2)C2=N1 DJSZNVQUJXGOOW-UHFFFAOYSA-N 0.000 claims 1
- HEINBMZDPIDHTD-LSDHHAIUSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-[(2R,5S)-2,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@H]1CN([C@H](C)CN1C)c1ccc2cc(-c3cn4cc(C)nc(C)c4n3)c(=O)oc2n1 HEINBMZDPIDHTD-LSDHHAIUSA-N 0.000 claims 1
- JEWJHHACJBFGJE-GXTWGEPZSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-[(2r,5s)-2,5-dimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(C)=NC(C)=CN3C=2)C(=O)O2)C2=N1 JEWJHHACJBFGJE-GXTWGEPZSA-N 0.000 claims 1
- OZUYPLDKSGKMQU-BETUJISGSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(C)=NC(C)=CN3C=2)C(=O)O2)C2=N1 OZUYPLDKSGKMQU-BETUJISGSA-N 0.000 claims 1
- ANJFEQMZMBVYNA-HNNXBMFYSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-[(3s)-4-ethyl-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1[C@H](C)N(CC)CCN1C1=CC=C(C=C(C=2N=C3C(C)=NC(C)=CN3C=2)C(=O)O2)C2=N1 ANJFEQMZMBVYNA-HNNXBMFYSA-N 0.000 claims 1
- KYMOWWWPEHHYIX-LSDHHAIUSA-N 3-(6-methylimidazo[1,2-a]pyrazin-2-yl)-7-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=NC(C)=CN3C=2)C(=O)O2)C2=N1 KYMOWWWPEHHYIX-LSDHHAIUSA-N 0.000 claims 1
- GGMRXOWQPZZHHO-UHFFFAOYSA-N 3-(6-methylimidazo[1,2-a]pyridin-2-yl)-7-(4-methylpiperazin-1-yl)pyrano[3,2-c]pyridin-2-one Chemical compound C1CN(C)CCN1C(N=C1)=CC2=C1C=C(C=1N=C3C=CC(C)=CN3C=1)C(=O)O2 GGMRXOWQPZZHHO-UHFFFAOYSA-N 0.000 claims 1
- JNFNOQFFVAXVKY-JKSUJKDBSA-N 3-(6-methylimidazo[1,2-a]pyridin-2-yl)-7-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC(C)=CN3C=2)C(=O)O2)C2=N1 JNFNOQFFVAXVKY-JKSUJKDBSA-N 0.000 claims 1
- IESPAQZDKIVXCY-CQSZACIVSA-N 3-(6-methylimidazo[1,2-a]pyridin-2-yl)-7-[(3r)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN[C@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC(C)=CN3C=2)C(=O)O2)C2=N1 IESPAQZDKIVXCY-CQSZACIVSA-N 0.000 claims 1
- IESPAQZDKIVXCY-AWEZNQCLSA-N 3-(6-methylimidazo[1,2-a]pyridin-2-yl)-7-[(3s)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC(C)=CN3C=2)C(=O)O2)C2=N1 IESPAQZDKIVXCY-AWEZNQCLSA-N 0.000 claims 1
- PXJMYTGWBSPLGE-UHFFFAOYSA-N 3-(6-methylimidazo[1,2-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[3,2-c]pyridin-2-one Chemical compound C=1N2C=C(C)C=CC2=NC=1C(C(OC1=C2)=O)=CC1=CN=C2N1CCNCC1 PXJMYTGWBSPLGE-UHFFFAOYSA-N 0.000 claims 1
- JPFANBVVRYMOOP-UHFFFAOYSA-N 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-(4-methylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(C=C(C=2N=C3C=C(C)C=CN3C=2)C(=O)O2)C2=N1 JPFANBVVRYMOOP-UHFFFAOYSA-N 0.000 claims 1
- MYGRPGGGVVBNHO-JKSUJKDBSA-N 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=C(C)C=CN3C=2)C(=O)O2)C2=N1 MYGRPGGGVVBNHO-JKSUJKDBSA-N 0.000 claims 1
- ZCRFKGQPOWYMOL-AWEZNQCLSA-N 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-[(2s)-2-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@H]1CNCCN1C1=CC=C(C=C(C=2N=C3C=C(C)C=CN3C=2)C(=O)O2)C2=N1 ZCRFKGQPOWYMOL-AWEZNQCLSA-N 0.000 claims 1
- XMZFXZSRQASUTH-AWEZNQCLSA-N 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-[(3s)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=C(C)C=CN3C=2)C(=O)O2)C2=N1 XMZFXZSRQASUTH-AWEZNQCLSA-N 0.000 claims 1
- YUMOYINVWIVTGQ-UHFFFAOYSA-N 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.N1=C2C=C(C)C=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCNCC1 YUMOYINVWIVTGQ-UHFFFAOYSA-N 0.000 claims 1
- QHLFDKRADNKWLQ-UHFFFAOYSA-N 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[3,2-c]pyridin-2-one;hydrochloride Chemical compound Cl.N1=C2C=C(C)C=CN2C=C1C(C(OC1=C2)=O)=CC1=CN=C2N1CCNCC1 QHLFDKRADNKWLQ-UHFFFAOYSA-N 0.000 claims 1
- MPSOEGBAEWEKTC-UHFFFAOYSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-(4-ethyl-1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC)CCCN1C1=CC=C(C=C(C=2N=C3C(Cl)=CC=CN3C=2)C(=O)O2)C2=N1 MPSOEGBAEWEKTC-UHFFFAOYSA-N 0.000 claims 1
- ZJUZCAGDZXJODA-UHFFFAOYSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-(4-ethylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CCN1CCN(CC1)c1ccc2cc(-c3cn4cccc(Cl)c4n3)c(=O)oc2n1 ZJUZCAGDZXJODA-UHFFFAOYSA-N 0.000 claims 1
- RWTINPPSNQBARR-UONOGXRCSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(Cl)=CC=CN3C=2)C(=O)O2)C2=N1 RWTINPPSNQBARR-UONOGXRCSA-N 0.000 claims 1
- BCBJLTTVGXGMKN-QWHCGFSZSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-[(2r,5s)-2,5-dimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(Cl)=CC=CN3C=2)C(=O)O2)C2=N1 BCBJLTTVGXGMKN-QWHCGFSZSA-N 0.000 claims 1
- LKDMRPOMNKQVED-OKILXGFUSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound ClC=1C=2N(C=CC=1)C=C(N=2)C1=CC=2C(=NC(=CC=2)N2C[C@H](N([C@H](C2)C)C)C)OC1=O LKDMRPOMNKQVED-OKILXGFUSA-N 0.000 claims 1
- OLFZQCXJABDFBW-BETUJISGSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(Cl)=CC=CN3C=2)C(=O)O2)C2=N1 OLFZQCXJABDFBW-BETUJISGSA-N 0.000 claims 1
- MJYMJSWICZQZDF-AWEZNQCLSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-[(3s)-4-ethyl-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1[C@H](C)N(CC)CCN1C1=CC=C(C=C(C=2N=C3C(Cl)=CC=CN3C=2)C(=O)O2)C2=N1 MJYMJSWICZQZDF-AWEZNQCLSA-N 0.000 claims 1
- CLHBXYWHKZYNSU-UHFFFAOYSA-N 3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)-7-(4-methyl-1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound FC=1C=2N(C=C(C=1)C)C=C(N=2)C1=CC=2C(=NC(=CC=2)N2CCN(CCC2)C)OC1=O CLHBXYWHKZYNSU-UHFFFAOYSA-N 0.000 claims 1
- BAFJYLHYVNWFII-UHFFFAOYSA-N 3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)-7-(4-methyl-1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCCN1C1=CC=C(C=C(C=2N=C3C(F)=CC=CN3C=2)C(=O)O2)C2=N1 BAFJYLHYVNWFII-UHFFFAOYSA-N 0.000 claims 1
- BRUJHKOAXZXPMB-UHFFFAOYSA-N 3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)-7-(4-methylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CN1CCN(CC1)c1ccc2cc(-c3cn4cccc(F)c4n3)c(=O)oc2n1 BRUJHKOAXZXPMB-UHFFFAOYSA-N 0.000 claims 1
- VFSSNTHXSIRGRV-UONOGXRCSA-N 3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)-7-[(2r,5s)-2,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(F)=CC=CN3C=2)C(=O)O2)C2=N1 VFSSNTHXSIRGRV-UONOGXRCSA-N 0.000 claims 1
- PSIFJIDLKUTWIO-LBPRGKRZSA-N 3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)-7-[(2s)-2-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@H]1CNCCN1C1=CC=C(C=C(C=2N=C3C(F)=CC=CN3C=2)C(=O)O2)C2=N1 PSIFJIDLKUTWIO-LBPRGKRZSA-N 0.000 claims 1
- FTTVRBRIVZWOPS-OKILXGFUSA-N 3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)-7-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@H]1CN(C[C@@H](C)N1C)c1ccc2cc(-c3cn4cccc(F)c4n3)c(=O)oc2n1 FTTVRBRIVZWOPS-OKILXGFUSA-N 0.000 claims 1
- GZPYXAMOKAQBMJ-LBPRGKRZSA-N 3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)-7-[(3s)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(F)=CC=CN3C=2)C(=O)O2)C2=N1 GZPYXAMOKAQBMJ-LBPRGKRZSA-N 0.000 claims 1
- IKMDPBZUQVVVEK-UHFFFAOYSA-N 3-imidazo[1,2-a]pyridin-2-yl-7-(4-methyl-1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCCN1C1=CC=C(C=C(C=2N=C3C=CC=CN3C=2)C(=O)O2)C2=N1 IKMDPBZUQVVVEK-UHFFFAOYSA-N 0.000 claims 1
- UAOFDBZJMULGTC-GASCZTMLSA-N 3-imidazo[1,2-a]pyridin-2-yl-7-[(3S,5R)-3,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound N=1C(=CN2C=1C=CC=C2)C1=CC=2C(=NC(=CC=2)N2C[C@H](N([C@H](C2)C)C)C)OC1=O UAOFDBZJMULGTC-GASCZTMLSA-N 0.000 claims 1
- SRGAJSFEMHPNGS-CYBMUJFWSA-N 3-imidazo[1,2-a]pyridin-2-yl-7-[(3r)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN[C@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC=CN3C=2)C(=O)O2)C2=N1 SRGAJSFEMHPNGS-CYBMUJFWSA-N 0.000 claims 1
- SZILQYFKDBLWOB-BTQNPOSSSA-N 3-imidazo[1,2-a]pyridin-2-yl-7-[(3r)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1CN[C@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC=CN3C=2)C(=O)O2)C2=N1 SZILQYFKDBLWOB-BTQNPOSSSA-N 0.000 claims 1
- SRGAJSFEMHPNGS-ZDUSSCGKSA-N 3-imidazo[1,2-a]pyridin-2-yl-7-[(3s)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC=CN3C=2)C(=O)O2)C2=N1 SRGAJSFEMHPNGS-ZDUSSCGKSA-N 0.000 claims 1
- GMHHNJGSGLOCHX-UHFFFAOYSA-N 3-imidazo[1,2-a]pyridin-2-yl-7-piperazin-1-ylpyrano[3,2-c]pyridin-2-one 3-(5-methylpyrazolo[1,5-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound CC1=CC2=CC(=NN2C=C1)C3=CC4=C(N=C(C=C4)N5CCNCC5)OC3=O.C1CN(CCN1)C2=NC=C3C=C(C(=O)OC3=C2)C4=CN5C=CC=CC5=N4 GMHHNJGSGLOCHX-UHFFFAOYSA-N 0.000 claims 1
- XCPQAHZZXHVKJL-UHFFFAOYSA-N 3-imidazo[1,2-a]pyrimidin-2-yl-7-(4-methylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound N=1C(=CN2C=1N=CC=C2)C1=CC=2C(=NC(=CC=2)N2CCN(CC2)C)OC1=O XCPQAHZZXHVKJL-UHFFFAOYSA-N 0.000 claims 1
- OQWCNLZGMUXIPF-OKILXGFUSA-N 3-imidazo[1,2-a]pyrimidin-2-yl-7-[(3R,5S)-3,4,5-trimethylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C[C@H]1CN(C[C@@H](C)N1C)c1ccc2cc(-c3cn4cccnc4n3)c(=O)oc2n1 OQWCNLZGMUXIPF-OKILXGFUSA-N 0.000 claims 1
- CUDLQBVFNTTZCL-UHFFFAOYSA-N 3-imidazo[2,1-b][1,3]thiazol-6-yl-7-(4-methyl-1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCCN1C1=CC=C(C=C(C=2N=C3SC=CN3C=2)C(=O)O2)C2=N1 CUDLQBVFNTTZCL-UHFFFAOYSA-N 0.000 claims 1
- OSCIOPPNBUSYOB-UHFFFAOYSA-N 3-imidazo[2,1-b][1,3]thiazol-6-yl-7-(4-methylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(C=C(C=2N=C3SC=CN3C=2)C(=O)O2)C2=N1 OSCIOPPNBUSYOB-UHFFFAOYSA-N 0.000 claims 1
- QZWOTHFUDTXROU-LLVKDONJSA-N 3-imidazo[2,1-b][1,3]thiazol-6-yl-7-[(3r)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN[C@H](C)CN1C1=CC=C(C=C(C=2N=C3SC=CN3C=2)C(=O)O2)C2=N1 QZWOTHFUDTXROU-LLVKDONJSA-N 0.000 claims 1
- QZWOTHFUDTXROU-NSHDSACASA-N 3-imidazo[2,1-b][1,3]thiazol-6-yl-7-[(3s)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3SC=CN3C=2)C(=O)O2)C2=N1 QZWOTHFUDTXROU-NSHDSACASA-N 0.000 claims 1
- CHXRIRRICPPGIU-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound N1=C2C(C)=NC(C)=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 CHXRIRRICPPGIU-UHFFFAOYSA-N 0.000 claims 1
- VPKHXWDMSJQUSG-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)pyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.N1=C2C(C)=NC(C)=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 VPKHXWDMSJQUSG-UHFFFAOYSA-N 0.000 claims 1
- KPUQNPSBRQAJDC-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(6-methylimidazo[1,2-a]pyrazin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound N1=C2C=NC(C)=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 KPUQNPSBRQAJDC-UHFFFAOYSA-N 0.000 claims 1
- UZRRVTFDEUABOI-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(6-methylimidazo[1,2-a]pyrazin-2-yl)pyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.N1=C2C=NC(C)=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 UZRRVTFDEUABOI-UHFFFAOYSA-N 0.000 claims 1
- RTQGNINELUHECF-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C=1N2C=C(C)C=C(F)C2=NC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 RTQGNINELUHECF-UHFFFAOYSA-N 0.000 claims 1
- JOVQGPURTKDKCW-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C=1N2C=C(C)C=C(F)C2=NC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 JOVQGPURTKDKCW-UHFFFAOYSA-N 0.000 claims 1
- OLLQJERRXIGGRF-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one hydrochloride Chemical compound Cl.Fc1cccn2cc(nc12)-c1cc2ccc(nc2oc1=O)N1CCCNCC1 OLLQJERRXIGGRF-UHFFFAOYSA-N 0.000 claims 1
- PERKUSDCGSKHRX-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-imidazo[1,2-a]pyridin-2-ylpyrano[2,3-b]pyridin-2-one;3-imidazo[2,1-b][1,3]thiazol-6-yl-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1=CC=2C=C(C=3N=C4SC=CN4C=3)C(=O)OC=2N=C1N1CCNCC1.C1=CC=2C=C(C=3N=C4C=CC=CN4C=3)C(=O)OC=2N=C1N1CCCNCC1 PERKUSDCGSKHRX-UHFFFAOYSA-N 0.000 claims 1
- ZQKWGTJVNOOWDA-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-imidazo[1,2-a]pyridin-2-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1=CC=2C=C(C=3N=C4C=CC=CN4C=3)C(=O)OC=2N=C1N1CCCNCC1 ZQKWGTJVNOOWDA-UHFFFAOYSA-N 0.000 claims 1
- SKOYRROKKOYJCL-UHFFFAOYSA-N 7-(4-ethyl-1,4-diazepan-1-yl)-3-(6-methylimidazo[1,2-a]pyrazin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C(C)N1CCN(CCC1)C1=CC=C2C(=N1)OC(C(=C2)C=1N=C2N(C=C(N=C2)C)C=1)=O SKOYRROKKOYJCL-UHFFFAOYSA-N 0.000 claims 1
- VMRIGBAADKCNSJ-UHFFFAOYSA-N 7-(4-ethyl-1,4-diazepan-1-yl)-3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CCN1CCCN(CC1)c1ccc2cc(-c3cn4cc(C)cc(F)c4n3)c(=O)oc2n1 VMRIGBAADKCNSJ-UHFFFAOYSA-N 0.000 claims 1
- KEZFRHHQNURTDX-UHFFFAOYSA-N 7-(4-ethyl-1,4-diazepan-1-yl)-3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C(C)N1CCN(CCC1)C1=CC=C2C(=N1)OC(C(=C2)C=1N=C2N(C=CC=C2F)C=1)=O KEZFRHHQNURTDX-UHFFFAOYSA-N 0.000 claims 1
- AAMDCFVCKOYINH-UHFFFAOYSA-N 7-(4-ethyl-1,4-diazepan-1-yl)-3-imidazo[1,2-a]pyridin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC)CCCN1C1=CC=C(C=C(C=2N=C3C=CC=CN3C=2)C(=O)O2)C2=N1 AAMDCFVCKOYINH-UHFFFAOYSA-N 0.000 claims 1
- DGKQMLLJQYHGJJ-UHFFFAOYSA-N 7-(4-ethylpiperazin-1-yl)-3-(7-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CCN1CCN(CC1)c1ccc2cc(-c3cn4ccc(C)cc4n3)c(=O)oc2n1 DGKQMLLJQYHGJJ-UHFFFAOYSA-N 0.000 claims 1
- ZXQBXQMZDNSKRV-UHFFFAOYSA-N 7-(4-ethylpiperazin-1-yl)-3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CCN1CCN(CC1)c1ccc2cc(-c3cn4cc(C)cc(F)c4n3)c(=O)oc2n1 ZXQBXQMZDNSKRV-UHFFFAOYSA-N 0.000 claims 1
- IMMRLWUDLMKITM-UHFFFAOYSA-N 7-(4-ethylpiperazin-1-yl)-3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CCN1CCN(CC1)c1ccc2cc(-c3cn4cccc(F)c4n3)c(=O)oc2n1 IMMRLWUDLMKITM-UHFFFAOYSA-N 0.000 claims 1
- ZPOPYGJKRXVMRH-UHFFFAOYSA-N 7-(4-methyl-1,4-diazepan-1-yl)-3-(6-methylimidazo[1,2-a]pyrazin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CN1CCCN(CC1)c1ccc2cc(-c3cn4cc(C)ncc4n3)c(=O)oc2n1 ZPOPYGJKRXVMRH-UHFFFAOYSA-N 0.000 claims 1
- JZMHQTXLUOPDMH-UHFFFAOYSA-N 7-(4-methyl-1,4-diazepan-1-yl)-3-(6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CN1CCN(CCC1)C1=CC=C2C(=N1)OC(C(=C2)C=1N=C2N(C=C(C=C2)C)C=1)=O JZMHQTXLUOPDMH-UHFFFAOYSA-N 0.000 claims 1
- IHJYNCKCJUELBJ-UHFFFAOYSA-N 7-(4-methyl-1,4-diazepan-1-yl)-3-(7-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCCN1C1=CC=C(C=C(C=2N=C3C=C(C)C=CN3C=2)C(=O)O2)C2=N1 IHJYNCKCJUELBJ-UHFFFAOYSA-N 0.000 claims 1
- DWRWHUFMVCPDEK-UONOGXRCSA-N 7-[(2R,5S)-2,5-dimethylpiperazin-1-yl]-3-(6-methylimidazo[1,2-a]pyrazin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C[C@H]1N(C[C@@H](NC1)C)C1=CC=C2C(=N1)OC(C(=C2)C=1N=C2N(C=C(N=C2)C)C=1)=O DWRWHUFMVCPDEK-UONOGXRCSA-N 0.000 claims 1
- WATUEUDATSCBKI-UONOGXRCSA-N 7-[(2R,5S)-2,5-dimethylpiperazin-1-yl]-3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C[C@H]1CN([C@H](C)CN1)c1ccc2cc(-c3cn4cc(C)cc(F)c4n3)c(=O)oc2n1 WATUEUDATSCBKI-UONOGXRCSA-N 0.000 claims 1
- RWWPHSLTMMPNNF-LSDHHAIUSA-N 7-[(2r,5s)-2,5-dimethylpiperazin-1-yl]-3-(6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC(C)=CN3C=2)C(=O)O2)C2=N1 RWWPHSLTMMPNNF-LSDHHAIUSA-N 0.000 claims 1
- OIAWUWPDEPQEJW-LSDHHAIUSA-N 7-[(2r,5s)-2,5-dimethylpiperazin-1-yl]-3-(7-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=C(C)C=CN3C=2)C(=O)O2)C2=N1 OIAWUWPDEPQEJW-LSDHHAIUSA-N 0.000 claims 1
- LJCXGIFUMVFIMZ-QWHCGFSZSA-N 7-[(2r,5s)-2,5-dimethylpiperazin-1-yl]-3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(F)=CC=CN3C=2)C(=O)O2)C2=N1 LJCXGIFUMVFIMZ-QWHCGFSZSA-N 0.000 claims 1
- GUKZWIZTIYJNSI-HNNXBMFYSA-N 7-[(2s)-2,4-dimethylpiperazin-1-yl]-3-(7-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C[C@H]1CN(C)CCN1C1=CC=C(C=C(C=2N=C3C=C(C)C=CN3C=2)C(=O)O2)C2=N1 GUKZWIZTIYJNSI-HNNXBMFYSA-N 0.000 claims 1
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- HIHSTYLBOMSGGO-HNNXBMFYSA-N 7-[(3S)-4-ethyl-3-methylpiperazin-1-yl]-3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CCN1CCN(C[C@@H]1C)c1ccc2cc(-c3cn4cc(C)cc(F)c4n3)c(=O)oc2n1 HIHSTYLBOMSGGO-HNNXBMFYSA-N 0.000 claims 1
- HGWXQSAEFMPFTE-OAHLLOKOSA-N 7-[(3r)-3,4-dimethylpiperazin-1-yl]-3-(6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)[C@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC(C)=CN3C=2)C(=O)O2)C2=N1 HGWXQSAEFMPFTE-OAHLLOKOSA-N 0.000 claims 1
- KQNGAQLMGJJHMG-CQSZACIVSA-N 7-[(3r)-3,4-dimethylpiperazin-1-yl]-3-imidazo[1,2-a]pyridin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)[C@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC=CN3C=2)C(=O)O2)C2=N1 KQNGAQLMGJJHMG-CQSZACIVSA-N 0.000 claims 1
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- NQZPKBFGGTXWJQ-BETUJISGSA-N 7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C(F)=CC=CN3C=2)C(=O)O2)C2=N1 NQZPKBFGGTXWJQ-BETUJISGSA-N 0.000 claims 1
- NVWOXBHQEWTUAL-OKILXGFUSA-N 7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-3-imidazo[1,2-a]pyridin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC=CN3C=2)C(=O)O2)C2=N1 NVWOXBHQEWTUAL-OKILXGFUSA-N 0.000 claims 1
- PUWGZSJJDJLITM-BETUJISGSA-N 7-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-3-imidazo[1,2-a]pyrimidin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3N=CC=CN3C=2)C(=O)O2)C2=N1 PUWGZSJJDJLITM-BETUJISGSA-N 0.000 claims 1
- HGWXQSAEFMPFTE-HNNXBMFYSA-N 7-[(3s)-3,4-dimethylpiperazin-1-yl]-3-(6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC(C)=CN3C=2)C(=O)O2)C2=N1 HGWXQSAEFMPFTE-HNNXBMFYSA-N 0.000 claims 1
- XHQVWUYYYYJYSN-HNNXBMFYSA-N 7-[(3s)-3,4-dimethylpiperazin-1-yl]-3-(7-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=C(C)C=CN3C=2)C(=O)O2)C2=N1 XHQVWUYYYYJYSN-HNNXBMFYSA-N 0.000 claims 1
- KQNGAQLMGJJHMG-AWEZNQCLSA-N 7-[(3s)-3,4-dimethylpiperazin-1-yl]-3-imidazo[1,2-a]pyridin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)[C@@H](C)CN1C1=CC=C(C=C(C=2N=C3C=CC=CN3C=2)C(=O)O2)C2=N1 KQNGAQLMGJJHMG-AWEZNQCLSA-N 0.000 claims 1
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| MX352861B (es) | 2011-12-30 | 2017-12-13 | Ptc Therapeutics Inc | Compuestos para tratar la atrofia muscular espinal. |
| MX357834B (es) | 2012-01-26 | 2018-07-26 | Ptc Therapeutics Inc | Compuestos de tipo isocumarina sustituidos para tratar la atrofia muscular espinal. |
| EP3406252B1 (en) | 2012-02-10 | 2020-05-13 | PTC Therapeutics, Inc. | Compounds for treating spinal muscular atrophy |
| EP2828247B1 (en) | 2012-03-23 | 2019-01-16 | PTC Therapeutics, Inc. | 4h-chromen-4-one derivatives for treating spinal muscular atrophy |
| JP2016503051A (ja) * | 2012-12-24 | 2016-02-01 | ラモット・アット・テル−アヴィヴ・ユニヴァーシティ・リミテッド | ナンセンス変異に起因する遺伝性疾患を治療する作用剤、及びこれを同定する方法 |
| CA2915764A1 (en) | 2013-08-19 | 2015-02-26 | F. Hoffmann-La Roche Ag | Screening method |
| WO2015105657A1 (en) | 2013-12-19 | 2015-07-16 | Ptc Therapeutics, Inc. | Methods for modulating the amount of rna transcripts |
| EP3310169B1 (en) | 2015-05-30 | 2023-05-17 | PTC Therapeutics, Inc. | Methods for modulating rna splicing |
| EP3133065A1 (en) | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Compounds for optically active devices |
| CA3119019C (en) | 2015-12-10 | 2024-06-11 | Ptc Therapeutics, Inc. | Compounds and methods for treating huntington's disease |
| JP2019535789A (ja) | 2016-11-28 | 2019-12-12 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｒｎａスプライシングを調節する方法 |
| EP3363786A1 (en) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Compounds for optically active devices |
| EP3363793A1 (en) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Hydrophobic compounds for optically active devices |
| EP4151627A1 (en) | 2017-06-05 | 2023-03-22 | PTC Therapeutics, Inc. | Compounds for treating huntington's disease |
| CN111372611A (zh) | 2017-06-14 | 2020-07-03 | Ptc医疗公司 | 修饰rna剪接的方法 |
| CN111163838B (zh) | 2017-06-28 | 2023-03-28 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| CN111182898B (zh) | 2017-06-28 | 2024-04-16 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| MX2020001425A (es) | 2017-08-04 | 2020-08-06 | Skyhawk Therapeutics Inc | Metodos y composiciones para modular el empalme. |
| BR112020019373A2 (pt) | 2018-03-27 | 2020-12-29 | Ptc Therapeutics, Inc. | Compostos para o tratamento da doença de hutington |
| KR20210038845A (ko) | 2018-06-27 | 2021-04-08 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료를 위한 헤테로아릴 화합물 |
| WO2020005882A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| IL279688B2 (en) | 2018-06-27 | 2025-01-01 | Ptc Therapeutics Inc | Heterocyclic and heteroaryl compounds for the treatment of Huntington's disease |
| WO2020004594A1 (ja) | 2018-06-27 | 2020-01-02 | 株式会社リボルナバイオサイエンス | 脊髄性筋萎縮症の予防または治療剤 |
| WO2020163248A1 (en) | 2019-02-04 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| KR102913697B1 (ko) | 2019-02-05 | 2026-01-15 | 스카이호크 테라퓨틱스, 인코포레이티드 | 스플라이싱을 조절하는 방법 및 조성물 |
| WO2020163541A1 (en) | 2019-02-05 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| KR102925385B1 (ko) | 2019-02-06 | 2026-02-11 | 스카이호크 테라퓨틱스, 인코포레이티드 | 스플라이싱을 조절하는 방법 및 조성물 |
| JP7603594B2 (ja) | 2019-02-06 | 2024-12-20 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| EP4327779A3 (en) | 2019-04-26 | 2024-05-08 | AMO Ireland | System and method |
| CA3139821A1 (en) | 2019-05-13 | 2020-11-19 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
| US11129829B2 (en) | 2019-06-17 | 2021-09-28 | Skyhawk Therapeutics, Inc. | Methods for modulating splicing |
| CN111116460A (zh) * | 2019-12-31 | 2020-05-08 | 阿里生物新材料（常州）有限公司 | 一种2-氯-4-羟基吡啶-3-甲醛氢溴酸盐的合成方法 |
| WO2021233800A1 (en) | 2020-05-20 | 2021-11-25 | Merck Patent Gmbh | Azacoumarin and azathiocoumarin derivatives for use in optically active devices |
| WO2023114539A1 (en) * | 2021-12-17 | 2023-06-22 | Pretzel Therapeutics, Inc. | Amino chromen-2-one modulators of polrmt |
| AU2024286618A1 (en) * | 2023-06-09 | 2025-10-30 | F. Hoffmann-La Roche Ag | Inducible gene expression system |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558618A (en) | 1968-04-01 | 1971-01-26 | Dow Chemical Co | Novel 4h-pyrazino(1,2-a)pyrimidine-4-ones |
| US4122274A (en) | 1977-05-25 | 1978-10-24 | Bristol-Myers Company | 3-Tetrazolo-5,6,7,8-substituted-pyrido[1,2-a]pyrimidin-4-ones |
| US4342870A (en) | 1980-03-28 | 1982-08-03 | Janssen Pharmaceutica N.V. | Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives |
| US5089633A (en) | 1987-04-28 | 1992-02-18 | Georgia Tech Research Corporation | Substituted isocoumarins |
| US5599816A (en) | 1990-05-02 | 1997-02-04 | Abbott Laboratories | Quinolizinone type compounds |
| EP0640083A1 (en) | 1992-05-13 | 1995-03-01 | E.I. Du Pont De Nemours And Company | Substituted pyrido 1,2-a]pyrimidinone derivatives as fungicides |
| US5597922A (en) * | 1994-07-29 | 1997-01-28 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Glycine receptor antagonist pharmacophore |
| HK1040076A1 (zh) | 1998-09-21 | 2002-05-24 | 希雷生物化学有限公司 | 作为整联蛋白抑制剂的喹嗪酮 |
| ATE363471T1 (de) | 2000-01-24 | 2007-06-15 | Astrazeneca Ab | Durch einen morpholinrest substituierte therapeutische verbindungen |
| GB0205281D0 (en) | 2002-03-06 | 2002-04-17 | Novartis Ag | Organic compounds |
| WO2003104216A1 (en) | 2002-06-10 | 2003-12-18 | Acadia Pharmaceuticals Inc. | Urotensin ii receptor modulators |
| AU2003298719A1 (en) | 2002-11-25 | 2004-06-18 | Antonia C. Kaloidis | Treatment for sma disease |
| US9068234B2 (en) | 2003-01-21 | 2015-06-30 | Ptc Therapeutics, Inc. | Methods and agents for screening for compounds capable of modulating gene expression |
| ES2339862T3 (es) | 2003-06-20 | 2010-05-26 | Novartis Vaccines And Diagnostics, Inc. | Compuestos de piridino 1,2-a-pirimidin-4-ona como agentes anticancerosos. |
| US20050046698A1 (en) | 2003-09-02 | 2005-03-03 | Knight Andrew Frederick | System and method for producing a selectable view of an object space |
| CA2545340A1 (en) * | 2003-11-10 | 2005-05-26 | Synta Pharmaceuticals, Corp. | Fused heterocyclic compounds |
| WO2005105801A1 (en) | 2004-05-04 | 2005-11-10 | Warner-Lambert Company Llc | Pyrrolyl substituted pyrido[2,3-d]pyrimidin-7-ones and derivatives thereof as therapeutic agents |
| US7846915B2 (en) | 2004-10-20 | 2010-12-07 | Resverlogix Corporation | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| US7399767B2 (en) | 2005-01-21 | 2008-07-15 | Ortho-Mcneil Pharmaceutical, Inc. | Heterocyclic benzo[c]chromene derivatives useful as modulators of the estrogen receptors |
| AR059339A1 (es) | 2006-02-09 | 2008-03-26 | Chugai Pharmaceutical Co Ltd | Derivados de la cumarina para trastornos proliferativos de celulas, composicion farmaceutica y agente terapeutico que los contiene |
| US8337941B2 (en) | 2006-07-27 | 2012-12-25 | The Trustees Of Columbia University In The City Of New York | Fluorescent substrates for monoamine transporters as optical false neurotransmitters |
| CA2700841A1 (en) * | 2007-09-27 | 2009-04-02 | The United States Of America, As Represented By The Secretary, Departmen T Of Health And Human Services | Isoindoline compounds for the treatment of spinal muscular atrophy and other uses |
| US8633019B2 (en) * | 2008-05-27 | 2014-01-21 | Ptc Therapeutics, Inc. | Methods for treating spinal muscular atrophy |
| WO2010019236A1 (en) | 2008-08-13 | 2010-02-18 | Ptc Therapeutics, Inc | Methods for treating spinal muscular atrophy |
| EP2501231B1 (en) | 2009-11-20 | 2016-12-21 | Merck Sharp & Dohme Corp. | Quinolizidinone carboxamide m1 receptor positive allosteric modulators |
| KR20130088002A (ko) | 2010-01-13 | 2013-08-07 | 재단법인 한국파스퇴르연구소 | 항-감염성 피리도(1,2-ａ)피리미딘 |
| MX352861B (es) | 2011-12-30 | 2017-12-13 | Ptc Therapeutics Inc | Compuestos para tratar la atrofia muscular espinal. |
| MX357834B (es) | 2012-01-26 | 2018-07-26 | Ptc Therapeutics Inc | Compuestos de tipo isocumarina sustituidos para tratar la atrofia muscular espinal. |
| EP3406252B1 (en) | 2012-02-10 | 2020-05-13 | PTC Therapeutics, Inc. | Compounds for treating spinal muscular atrophy |
| EP2828247B1 (en) | 2012-03-23 | 2019-01-16 | PTC Therapeutics, Inc. | 4h-chromen-4-one derivatives for treating spinal muscular atrophy |
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