BR112014021531B1 - Composto, composição farmacêutica e usos dos mesmos - Google Patents
Composto, composição farmacêutica e usos dos mesmos Download PDFInfo
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- BR112014021531B1 BR112014021531B1 BR112014021531-6A BR112014021531A BR112014021531B1 BR 112014021531 B1 BR112014021531 B1 BR 112014021531B1 BR 112014021531 A BR112014021531 A BR 112014021531A BR 112014021531 B1 BR112014021531 B1 BR 112014021531B1
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- Prior art keywords
- pyridin
- pyrano
- 8alkyl
- formula
- amino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 1365
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 53
- 208000002320 spinal muscular atrophy Diseases 0.000 claims abstract description 311
- 238000011282 treatment Methods 0.000 claims abstract description 26
- -1 2,5-diazabicyclo[2.2.1]heptyl Chemical group 0.000 claims description 556
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 313
- 241000282414 Homo sapiens Species 0.000 claims description 208
- 125000000623 heterocyclic group Chemical group 0.000 claims description 135
- 125000001424 substituent group Chemical group 0.000 claims description 130
- 125000001072 heteroaryl group Chemical group 0.000 claims description 92
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 239000003814 drug Substances 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000003981 vehicle Substances 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims description 5
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 150000001805 chlorine compounds Chemical group 0.000 claims description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 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
- KSROZPZSAMXOQB-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-(1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1=CC=2C=C(C=3SC4=CC=CC=C4N=3)C(=O)OC=2N=C1N1CCCNCC1 KSROZPZSAMXOQB-UHFFFAOYSA-N 0.000 claims 1
- GVPDMNFIFJNGSM-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-(1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1=CC=2C=C(C=3SC4=CC=CC=C4N=3)C(=O)OC=2N=C1N1CCCNCC1 GVPDMNFIFJNGSM-UHFFFAOYSA-N 0.000 claims 1
- KRYPYZIBXDPCHL-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-(4-ethylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC)CCN1C1=CC=C(C=C(C=2SC3=CC=CC=C3N=2)C(=O)O2)C2=N1 KRYPYZIBXDPCHL-UHFFFAOYSA-N 0.000 claims 1
- QSUPGJHJMRNGSZ-UHFFFAOYSA-N 3-(1,3-benzothiazol-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=2SC3=CC=CC=C3N=2)C(=O)O2)C2=N1 QSUPGJHJMRNGSZ-UHFFFAOYSA-N 0.000 claims 1
- WQOHETICJCDXLH-UHFFFAOYSA-N 3-(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=C3N=2)C(=O)O2)C2=N1 WQOHETICJCDXLH-UHFFFAOYSA-N 0.000 claims 1
- QPSWZTHMQYHNFC-UHFFFAOYSA-N 3-(1,3-benzothiazol-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=1SC3=CC=CC=C3N=1)C(=O)O2 QPSWZTHMQYHNFC-UHFFFAOYSA-N 0.000 claims 1
- QCDUSPWEQJOLIK-UHFFFAOYSA-N 3-(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=C3N=2)C(=O)O2)C2=N1 QCDUSPWEQJOLIK-UHFFFAOYSA-N 0.000 claims 1
- AJVSYQAXYJXDOX-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-(4-propylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CCC)CCN1C1=CC=C(C=C(C=2SC3=CC=CC=C3N=2)C(=O)O2)C2=N1 AJVSYQAXYJXDOX-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
- QKVXTKBCXDNJJF-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-[4-(2-chloroethyl)piperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CCCl)CCN1C1=CC=C(C=C(C=2SC3=CC=CC=C3N=2)C(=O)O2)C2=N1 QKVXTKBCXDNJJF-UHFFFAOYSA-N 0.000 claims 1
- OCDOOVAHVZMFAM-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-[4-(2-hydroxyethyl)piperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CCO)CCN1C1=CC=C(C=C(C=2SC3=CC=CC=C3N=2)C(=O)O2)C2=N1 OCDOOVAHVZMFAM-UHFFFAOYSA-N 0.000 claims 1
- LKCJLQRQALLCNM-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1=CC=2C=C(C=3SC4=CC=CC=C4N=3)C(=O)OC=2N=C1N1CCNCC1 LKCJLQRQALLCNM-UHFFFAOYSA-N 0.000 claims 1
- DKXHSPBEZFMMFY-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-7-(1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1=CC=2C=C(C=3OC4=CC=CC=C4N=3)C(=O)OC=2N=C1N1CCCNCC1 DKXHSPBEZFMMFY-UHFFFAOYSA-N 0.000 claims 1
- IPQJUUHZJXVKRD-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-7-(1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1=CC=2C=C(C=3OC4=CC=CC=C4N=3)C(=O)OC=2N=C1N1CCCNCC1 IPQJUUHZJXVKRD-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
- YPWUQKZEUMJXSK-UHFFFAOYSA-N 3-(2-methylimidazo[2,1-b][1,3]thiazol-6-yl)-7-piperazin-1-ylpyrano[3,2-c]pyridin-2-one Chemical compound N1=C2SC(C)=CN2C=C1C(C(OC1=C2)=O)=CC1=CN=C2N1CCNCC1 YPWUQKZEUMJXSK-UHFFFAOYSA-N 0.000 claims 1
- ACRMRNRAPTVPIH-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-(1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound N=1C=2C(Cl)=CC=CC=2SC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 ACRMRNRAPTVPIH-UHFFFAOYSA-N 0.000 claims 1
- OBZZIDNNWHXFBO-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-(1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.N=1C=2C(Cl)=CC=CC=2SC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 OBZZIDNNWHXFBO-UHFFFAOYSA-N 0.000 claims 1
- GPRDQMSNENVDCR-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-(4-ethylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC)CCN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 GPRDQMSNENVDCR-UHFFFAOYSA-N 0.000 claims 1
- GEEQERIGFMNVAM-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-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=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 GEEQERIGFMNVAM-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
- UYNKFYXWIKBTSI-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-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=1SC3=CC=CC(Cl)=C3N=1)C(=O)O2 UYNKFYXWIKBTSI-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
- WEMYQMNSOOBMKJ-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-(4-propylpiperazin-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CCC)CCN1C1=CC=C(C=C(C=2SC3=CC=CC(Cl)=C3N=2)C(=O)O2)C2=N1 WEMYQMNSOOBMKJ-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
- GEMKKRVPDZRBCJ-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound N=1C=2C(Cl)=CC=CC=2SC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCNCC1 GEMKKRVPDZRBCJ-UHFFFAOYSA-N 0.000 claims 1
- DSNMEXZHKJAMLN-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-piperazin-1-ylpyrano[3,2-c]pyridin-2-one Chemical compound N=1C=2C(Cl)=CC=CC=2SC=1C(C(OC1=C2)=O)=CC1=CN=C2N1CCNCC1 DSNMEXZHKJAMLN-UHFFFAOYSA-N 0.000 claims 1
- FHXBZCYRNGKJAB-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-piperazin-1-ylpyrano[3,2-c]pyridin-2-one;hydrochloride Chemical compound Cl.N=1C=2C(Cl)=CC=CC=2SC=1C(C(OC1=C2)=O)=CC1=CN=C2N1CCNCC1 FHXBZCYRNGKJAB-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
- ASTMLKWFFMVMTQ-UHFFFAOYSA-N 3-(4-methyl-1,3-thiazol-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound CC1=CSC(C=2C(OC3=NC(=CC=C3C=2)N2CCNCC2)=O)=N1 ASTMLKWFFMVMTQ-UHFFFAOYSA-N 0.000 claims 1
- JUQCNMHHFCYGKG-UHFFFAOYSA-N 3-(4-methyl-1,3-thiazol-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.CC1=CSC(C=2C(OC3=NC(=CC=C3C=2)N2CCNCC2)=O)=N1 JUQCNMHHFCYGKG-UHFFFAOYSA-N 0.000 claims 1
- ZGDMSGFYSVCVOZ-UHFFFAOYSA-N 3-(5-methylpyrazolo[1,5-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1=C2C=C(C)C=CN2N=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCNCC1 ZGDMSGFYSVCVOZ-UHFFFAOYSA-N 0.000 claims 1
- RDYGYYFJVQLEOS-UHFFFAOYSA-N 3-(5-methylpyrazolo[1,5-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1=C2C=C(C)C=CN2N=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCNCC1 RDYGYYFJVQLEOS-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
- YOTNTOHMVROYOB-LBPRGKRZSA-N 3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)-7-[(3S)-3-methylpiperazin-1-yl]pyrano[2,3-b]pyridin-2-one Chemical compound CC=1N=C(C=2N(C1)C=C(N2)C2=CC=1C(=NC(=CC1)N1C[C@@H](NCC1)C)OC2=O)C YOTNTOHMVROYOB-LBPRGKRZSA-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
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- 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
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- OCSODONEUQPUNY-UHFFFAOYSA-N 3-(8-chloroimidazo[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(Cl)=CC=CN3C=2)C(=O)O2)C2=N1 OCSODONEUQPUNY-UHFFFAOYSA-N 0.000 claims 1
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- BIMLUZXBCLXBPR-UHFFFAOYSA-N 3-imidazo[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=CC=CN3C=2)C(=O)O2)C2=N1 BIMLUZXBCLXBPR-UHFFFAOYSA-N 0.000 claims 1
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- 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
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- 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
- SQHBGZUGDWHPJR-UHFFFAOYSA-N 3-imidazo[1,2-a]pyrimidin-2-yl-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1=CC=2C=C(C=3N=C4N=CC=CN4C=3)C(=O)OC=2N=C1N1CCNCC1 SQHBGZUGDWHPJR-UHFFFAOYSA-N 0.000 claims 1
- UAEDPNHIXVQCQP-UHFFFAOYSA-N 3-imidazo[1,2-a]pyrimidin-2-yl-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1=CC=2C=C(C=3N=C4N=CC=CN4C=3)C(=O)OC=2N=C1N1CCNCC1 UAEDPNHIXVQCQP-UHFFFAOYSA-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
- BRJUAMZRDGNETB-UHFFFAOYSA-N 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 BRJUAMZRDGNETB-UHFFFAOYSA-N 0.000 claims 1
- QGAKFEXLOBUILD-UHFFFAOYSA-N 3-imidazo[2,1-b][1,3]thiazol-6-yl-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1=CC=2C=C(C=3N=C4SC=CN4C=3)C(=O)OC=2N=C1N1CCNCC1 QGAKFEXLOBUILD-UHFFFAOYSA-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
- 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
- KRKUTJCTVIUJBG-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C=1N2C=C(C)C=CC2=NC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 KRKUTJCTVIUJBG-UHFFFAOYSA-N 0.000 claims 1
- WFDKIIWDOFBCAY-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(7-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound N1=C2C=C(C)C=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 WFDKIIWDOFBCAY-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
- CPRCFYHEMABGKH-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-(8-fluoroimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound N1=C2C(F)=CC=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 CPRCFYHEMABGKH-UHFFFAOYSA-N 0.000 claims 1
- UWYNBPZTLLSJNV-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-imidazo[1,2-a]pyridin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1=CC=2C=C(C=3N=C4C=CC=CN4C=3)C(=O)OC=2N=C1N1CCCNCC1 UWYNBPZTLLSJNV-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
- RSNDWRXPANGOEV-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-imidazo[1,2-a]pyrimidin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1=CC=2C=C(C=3N=C4N=CC=CN4C=3)C(=O)OC=2N=C1N1CCCNCC1 RSNDWRXPANGOEV-UHFFFAOYSA-N 0.000 claims 1
- XXVABIIPPDIUEX-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-imidazo[1,2-a]pyrimidin-2-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C1=CC=2C=C(C=3N=C4N=CC=CN4C=3)C(=O)OC=2N=C1N1CCCNCC1 XXVABIIPPDIUEX-UHFFFAOYSA-N 0.000 claims 1
- GUGNZJPYKLZTEV-UHFFFAOYSA-N 7-(1,4-diazepan-1-yl)-3-imidazo[2,1-b][1,3]thiazol-6-ylpyrano[2,3-b]pyridin-2-one Chemical compound C1=CC=2C=C(C=3N=C4SC=CN4C=3)C(=O)OC=2N=C1N1CCCNCC1 GUGNZJPYKLZTEV-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
- RGFZGIHTHBNPST-UHFFFAOYSA-N 7-(4-ethyl-1,4-diazepan-1-yl)-3-imidazo[1,2-a]pyrimidin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound CCN1CCCN(CC1)c1ccc2cc(-c3cn4cccnc4n3)c(=O)oc2n1 RGFZGIHTHBNPST-UHFFFAOYSA-N 0.000 claims 1
- SWIBBGGTAPGCQG-UHFFFAOYSA-N 7-(4-ethylpiperazin-1-yl)-3-(4-methyl-1,3-thiazol-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(CC)CCN1C1=CC=C(C=C(C=2SC=C(C)N=2)C(=O)O2)C2=N1 SWIBBGGTAPGCQG-UHFFFAOYSA-N 0.000 claims 1
- CGQYENQUBSUWSG-UHFFFAOYSA-N 7-(4-ethylpiperazin-1-yl)-3-(6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CCN1CCN(CC1)c1ccc2cc(-c3cn4cc(C)ccc4n3)c(=O)oc2n1 CGQYENQUBSUWSG-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
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- 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
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- ZUWFIJLBAVYCHG-GJZGRUSLSA-N 7-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(6,8-dimethylimidazo[1,2-a]pyrazin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound Cc1cn2cc(nc2c(C)n1)-c1cc2ccc(nc2oc1=O)N1C[C@@H]2C[C@H]1CN2 ZUWFIJLBAVYCHG-GJZGRUSLSA-N 0.000 claims 1
- TZOZSDCIOVYTEM-KBPBESRZSA-N 7-[(1S,4S)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(8-fluoro-6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound Cc1cc(F)c2nc(cn2c1)-c1cc2ccc(nc2oc1=O)N1C[C@@H]2C[C@H]1CN2 TZOZSDCIOVYTEM-KBPBESRZSA-N 0.000 claims 1
- MECYKQWCJOBTFL-HOTGVXAUSA-N 7-[(1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound CN1[C@@H]2CN([C@H](C1)C2)C1=CC=C2C(=N1)OC(C(=C2)C=1N=C2N(C=C(C=C2)C)C=1)=O MECYKQWCJOBTFL-HOTGVXAUSA-N 0.000 claims 1
- BNVRQZNXUOJTFA-GJZGRUSLSA-N 7-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-3-(6-methylimidazo[1,2-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C=1N2C=C(C)C=CC2=NC=1C(C(OC1=N2)=O)=CC1=CC=C2N1[C@H](CN2)C[C@H]2C1 BNVRQZNXUOJTFA-GJZGRUSLSA-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
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- 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
- YMRMCXXOOSTWGL-ZDUSSCGKSA-N 7-[(2s)-2,4-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)CCN1C1=CC=C(C=C(C=2N=C3C(F)=CC=CN3C=2)C(=O)O2)C2=N1 YMRMCXXOOSTWGL-ZDUSSCGKSA-N 0.000 claims 1
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- OSVXRUXEPLRJBU-OKILXGFUSA-N 7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-3-(7-methylimidazo[1,2-a]pyrimidin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C[C@@H]1CN(C[C@@H](N1)C)C1=CC=C2C(=N1)OC(C(=C2)C=1N=C2N(C=CC(=N2)C)C=1)=O OSVXRUXEPLRJBU-OKILXGFUSA-N 0.000 claims 1
- OZDNVORSFCQWEI-IYBDPMFKSA-N 7-[(3R,5S)-4-ethyl-3,5-dimethylpiperazin-1-yl]-3-imidazo[1,2-a]pyridin-2-ylpyrano[2,3-b]pyridin-2-one Chemical compound CCN1[C@@H](C)CN(C[C@H]1C)c1ccc2cc(-c3cn4ccccc4n3)c(=O)oc2n1 OZDNVORSFCQWEI-IYBDPMFKSA-N 0.000 claims 1
- 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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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
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| PL2809322T3 (pl) | 2012-01-26 | 2019-11-29 | Ptc Therapeutics Inc | Związki do leczenia zaniku mięśni pochodzenia rdzeniowego |
| DK2812004T3 (en) | 2012-02-10 | 2018-10-15 | Ptc Therapeutics Inc | COMPOUNDS FOR TREATMENT OF SPINAL MUSCLE DROPHY |
| KR102109992B1 (ko) | 2012-03-23 | 2020-05-13 | 피티씨 테라퓨틱스, 인크. | 척수성 근위축증을 치료하기 위한 화합물 |
| KR20150098675A (ko) * | 2012-12-24 | 2015-08-28 | 라모트 앳 텔-아비브 유니버시티 리미티드 | 넌센스 돌연변이로부터 생긴 유전적 질환을 치료하기 위한 물질 및 이를 확인하는 방법 |
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| EP3082820B1 (en) | 2013-12-19 | 2022-07-20 | PTC Therapeutics, Inc. | Methods for modulating the amount of rna transcripts |
| EP4249472A3 (en) | 2015-05-30 | 2023-12-13 | PTC Therapeutics, Inc. | Methods for modulating rna splicing |
| EP3133065A1 (en) | 2015-08-21 | 2017-02-22 | Merck Patent GmbH | Compounds for optically active devices |
| IL294124B2 (en) | 2015-12-10 | 2024-02-01 | Ptc Therapeutics Inc | Methods for treating huntington's disease |
| EA201991309A1 (ru) | 2016-11-28 | 2019-11-29 | Способы модуляции сплайсинга рнк | |
| 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 |
| US11407753B2 (en) | 2017-06-05 | 2022-08-09 | Ptc Therapeutics, Inc. | Compounds for treating Huntington's disease |
| KR20200017476A (ko) | 2017-06-14 | 2020-02-18 | 피티씨 테라퓨틱스, 인크. | Rna 스플라이싱의 변경 방법 |
| US11382918B2 (en) | 2017-06-28 | 2022-07-12 | Ptc Therapeutics, Inc. | Methods for treating Huntington's Disease |
| WO2019005993A1 (en) | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | METHODS OF TREATING HUNTINGTON'S DISEASE |
| WO2019028440A1 (en) | 2017-08-04 | 2019-02-07 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATING SPLICING |
| MX2020009957A (es) | 2018-03-27 | 2021-01-15 | Ptc Therapeutics Inc | Compuestos para el tratamiento de enfermedad de hungtinton. |
| EP3814360B8 (en) | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| PL3814357T3 (pl) | 2018-06-27 | 2024-09-16 | Ptc Therapeutics, Inc. | Związki heterocykliczne i heteroarylowe do leczenia choroby huntingtona |
| EP3814345B8 (en) | 2018-06-27 | 2024-10-30 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| BR112020026637A2 (pt) | 2018-06-27 | 2021-03-30 | Reborna Biosciences, Inc. | Agente profilático ou terapêutico para atrofia muscular espinhal |
| WO2020163248A1 (en) | 2019-02-04 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| EP3920915A4 (en) | 2019-02-05 | 2022-10-05 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATING SPLICE |
| CN114126613A (zh) | 2019-02-05 | 2022-03-01 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| CN113661162A (zh) | 2019-02-06 | 2021-11-16 | 斯基霍克疗法公司 | 用于调节剪接的方法和组合物 |
| WO2020163544A1 (en) | 2019-02-06 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| WO2020231977A1 (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 |
| US20230203214A1 (en) | 2020-05-20 | 2023-06-29 | 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 |
| WO2024251925A1 (en) * | 2023-06-09 | 2024-12-12 | F. Hoffmann-La Roche Ag | Inducible gene expression system |
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| 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 |
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| CN1809563A (zh) | 2003-06-20 | 2006-07-26 | 希龙公司 | 吡啶并[1,2－a]嘧啶－4－酮化合物用作抗癌药 |
| US20050046698A1 (en) * | 2003-09-02 | 2005-03-03 | Knight Andrew Frederick | System and method for producing a selectable view of an object space |
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| WO2006045010A2 (en) | 2004-10-20 | 2006-04-27 | Resverlogix Corp. | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| AU2006206446A1 (en) | 2005-01-21 | 2006-07-27 | Janssen Pharmaceutica N.V. | Novel 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 |
| EP2215074B1 (en) * | 2007-09-27 | 2014-02-19 | The United States of America, as Represented by the Secretary, Department of Health and Human Services | Isoindoline compounds for the treatment of spinal muscular atrophy and other uses |
| WO2009151546A2 (en) | 2008-05-27 | 2009-12-17 | Ptc Therapeutics, Inc. | Methods for treating spinal muscular atrophy |
| WO2010019243A1 (en) | 2008-08-13 | 2010-02-18 | Ptc Therapeutics, Inc. | Methods for treating viral infections |
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| CN102812023A (zh) | 2010-01-13 | 2012-12-05 | 韩国巴斯德研究所 | 抗感染吡啶并(1,2-a)嘧啶类 |
| KR102057351B1 (ko) | 2011-12-30 | 2019-12-18 | 피티씨 테라퓨틱스, 인크. | 척수성 근위축증을 치료하기 위한 화합물 |
| PL2809322T3 (pl) | 2012-01-26 | 2019-11-29 | Ptc Therapeutics Inc | Związki do leczenia zaniku mięśni pochodzenia rdzeniowego |
| DK2812004T3 (en) | 2012-02-10 | 2018-10-15 | Ptc Therapeutics Inc | COMPOUNDS FOR TREATMENT OF SPINAL MUSCLE DROPHY |
| KR102109992B1 (ko) | 2012-03-23 | 2020-05-13 | 피티씨 테라퓨틱스, 인크. | 척수성 근위축증을 치료하기 위한 화합물 |
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| EP2819519A4 (en) | 2015-09-02 |
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| BR112014021531A8 (pt) | 2021-06-15 |
| EA029155B1 (ru) | 2018-02-28 |
| KR102099997B1 (ko) | 2020-04-13 |
| EP2819519B1 (en) | 2019-10-23 |
| CA2865957A1 (en) | 2013-09-06 |
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| EP2819519A1 (en) | 2015-01-07 |
| WO2013130689A1 (en) | 2013-09-06 |
| KR20140131384A (ko) | 2014-11-12 |
| US20150166575A1 (en) | 2015-06-18 |
| CA2865957C (en) | 2020-02-11 |
| US9371336B2 (en) | 2016-06-21 |
| CN104302181B (zh) | 2017-09-15 |
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