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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| USRE47689E1 (en) | 2011-12-30 | 2019-11-05 | Ptc Therapeutics, Inc. | Compounds for treating spinal muscular atrophy |
| PL2809322T3 (pl) | 2012-01-26 | 2019-11-29 | Ptc Therapeutics Inc | Związki do leczenia zaniku mięśni pochodzenia rdzeniowego |
| CN119528903A (zh) | 2012-02-10 | 2025-02-28 | Ptc医疗公司 | 用于治疗脊髓性肌萎缩的化合物 |
| KR102109992B1 (ko) | 2012-03-23 | 2020-05-13 | 피티씨 테라퓨틱스, 인크. | 척수성 근위축증을 치료하기 위한 화합물 |
| US10987370B2 (en) * | 2012-12-24 | 2021-04-27 | Ramot At Tel-Aviv University Ltd. | Methods of inducing read-through of a nonsense mutation associated with ataxia telangiectasia, Rett syndrome or spinal muscular atrophy by erythromycin or azithromycin |
| BR112015032718A2 (pt) | 2013-08-19 | 2019-09-17 | Hoffmann La Roche | composto de modificação de splicing do gene foxm1, uso do composto, formulação farmacêutica e métodos de triagem de compostos |
| WO2015105657A1 (en) | 2013-12-19 | 2015-07-16 | Ptc Therapeutics, Inc. | Methods for modulating the amount of rna transcripts |
| US10668171B2 (en) | 2015-05-30 | 2020-06-02 | Ptc Therapeutics, Inc. | Methods for modulating RNA splicing |
| EP3133065A1 (en) | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Compounds for optically active devices |
| EA201800367A1 (ru) | 2015-12-10 | 2019-02-28 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения болезни хантингтона |
| US11702646B2 (en) | 2016-11-28 | 2023-07-18 | Ptc Therapeutics, Inc. | Methods for modulating RNA splicing |
| EP3363786A1 (en) | 2017-02-15 | 2018-08-22 | Merck Patent GmbH | Compounds for optically active devices |
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| KR20200033249A (ko) | 2017-06-05 | 2020-03-27 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료 화합물 |
| JP2020523365A (ja) | 2017-06-14 | 2020-08-06 | 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スプライシングを改変する方法 |
| US11395822B2 (en) | 2017-06-28 | 2022-07-26 | Ptc Therapeutics, Inc. | Methods for treating Huntington's disease |
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| CN111499615B (zh) | 2017-08-04 | 2024-02-02 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
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| EA202092899A1 (ru) | 2018-06-27 | 2021-05-14 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Гетероарильные соединения для лечения болезни гентингтона |
| EP3814360B8 (en) | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| BR112020026545A2 (pt) | 2018-06-27 | 2021-03-23 | Ptc Therapeutics, Inc. | Compostos heterocíclicos e de heteroarila para o tratamento da doença de huntington |
| SG11202013088YA (en) | 2018-06-27 | 2021-02-25 | Reborna Biosciences Inc | Prophylactic or therapeutic agent for spinal muscular atrophy |
| CN114007613A (zh) | 2019-02-05 | 2022-02-01 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
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| BR112022023523A2 (pt) | 2020-05-20 | 2023-01-17 | AMO Ireland | Derivados de azacumarina e azatiocumarina para uso em dispositivos opticamente ativos |
| US20250066377A1 (en) * | 2021-12-17 | 2025-02-27 | Pretzel Therapeutics, Inc. | Amino chromen-2-one modulators of polrmt |
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| CN119528903A (zh) | 2012-02-10 | 2025-02-28 | Ptc医疗公司 | 用于治疗脊髓性肌萎缩的化合物 |
| KR102109992B1 (ko) | 2012-03-23 | 2020-05-13 | 피티씨 테라퓨틱스, 인크. | 척수성 근위축증을 치료하기 위한 화합물 |
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