EA029155B1 - Соединения для лечения спинальной мышечной атрофии - Google Patents

Info

Publication number

EA029155B1

EA029155B1 EA201491617A EA201491617A EA029155B1 EA 029155 B1 EA029155 B1 EA 029155B1 EA 201491617 A EA201491617 A EA 201491617A EA 201491617 A EA201491617 A EA 201491617A EA 029155 B1 EA029155 B1 EA 029155B1

Authority

EA

Eurasian Patent Office

Prior art keywords

pyridin

pyrano

compound

patient

gene

Prior art date

2012-03-01

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 804
• 208000002320 spinal muscular atrophy Diseases 0.000 title claims abstract description 7
• 108090000623 proteins and genes Proteins 0.000 claims description 600
• 108020004999 messenger RNA Proteins 0.000 claims description 356
• -1 diazabicyclo [2.2.1] heptyl Chemical group 0.000 claims description 263
• 238000000034 method Methods 0.000 claims description 109
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 53
• 102000004169 proteins and genes Human genes 0.000 claims description 50
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 47
• 239000008194 pharmaceutical composition Substances 0.000 claims description 45
• 210000005260 human cell Anatomy 0.000 claims description 32
• 230000001965 increasing effect Effects 0.000 claims description 25
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 22
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 17
• 239000003085 diluting agent Substances 0.000 claims description 17
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
• 239000003937 drug carrier Substances 0.000 claims description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• NRGKFNDKBDBBGY-UHFFFAOYSA-N 1h-pyridin-2-one;hydrochloride Chemical compound Cl.O=C1C=CC=CN1 NRGKFNDKBDBBGY-UHFFFAOYSA-N 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 4
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• NZIJQALQNOFPQK-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-3-(5-methylpyrazolo[1,5-a]pyridin-2-yl)pyrano[2,3-b]pyridin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(C=C(C2=NN3C=CC(C)=CC3=C2)C(=O)O2)C2=N1 NZIJQALQNOFPQK-UHFFFAOYSA-N 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000001072 heteroaryl group Chemical group 0.000 claims 2
• 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
• 125000005960 1,4-diazepanyl group Chemical group 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
• 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
• 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
• 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
• 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
• 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
• NQLZUCIBVVEODX-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.N=1C=2C(Cl)=CC=CC=2SC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCNCC1 NQLZUCIBVVEODX-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
• 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
• QCUDZUJOEKKOMA-UHFFFAOYSA-N 3-(6-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=CC(C)=CN3C=2)C(=O)O2)C2=N1 QCUDZUJOEKKOMA-UHFFFAOYSA-N 0.000 claims 1
• WJRSFFLLTDWTEJ-UHFFFAOYSA-N 3-(6-methylimidazo[1,2-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound C=1N2C=C(C)C=CC2=NC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCNCC1 WJRSFFLLTDWTEJ-UHFFFAOYSA-N 0.000 claims 1
• MOMOZUMYVGXCPQ-UHFFFAOYSA-N 3-(6-methylimidazo[1,2-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one;hydrochloride Chemical compound Cl.C=1N2C=C(C)C=CC2=NC=1C(C(OC1=N2)=O)=CC1=CC=C2N1CCNCC1 MOMOZUMYVGXCPQ-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
• MEMNTFKPFPXDBQ-UHFFFAOYSA-N 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[2,3-b]pyridin-2-one Chemical compound N1=C2C=C(C)C=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCNCC1 MEMNTFKPFPXDBQ-UHFFFAOYSA-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
• YQTGGYHBSMQEJL-UHFFFAOYSA-N 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-piperazin-1-ylpyrano[3,2-c]pyridin-2-one Chemical compound N1=C2C=C(C)C=CN2C=C1C(C(OC1=C2)=O)=CC1=CN=C2N1CCNCC1 YQTGGYHBSMQEJL-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
• GNZDRRVEWCDHCN-UHFFFAOYSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-(1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one Chemical compound N1=C2C(Cl)=CC=CN2C=C1C(C(OC1=N2)=O)=CC1=CC=C2N1CCCNCC1 GNZDRRVEWCDHCN-UHFFFAOYSA-N 0.000 claims 1
• WSBZPLVIUUQWIZ-UHFFFAOYSA-N 3-(8-chloroimidazo[1,2-a]pyridin-2-yl)-7-(1,4-diazepan-1-yl)pyrano[2,3-b]pyridin-2-one hydrochloride Chemical compound Cl.Clc1cccn2cc(nc12)-c1cc2ccc(nc2oc1=O)N1CCCNCC1 WSBZPLVIUUQWIZ-UHFFFAOYSA-N 0.000 claims 1
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