JP2015526394A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2015526394A5 JP2015526394A5 JP2015518522A JP2015518522A JP2015526394A5 JP 2015526394 A5 JP2015526394 A5 JP 2015526394A5 JP 2015518522 A JP2015518522 A JP 2015518522A JP 2015518522 A JP2015518522 A JP 2015518522A JP 2015526394 A5 JP2015526394 A5 JP 2015526394A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- methyl
- thieno
- pyrimidin
- methoxybenzyl
- 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
Links
- -1 —C 1-6 haloalkoxy Chemical group 0.000 claims 85
- 125000000217 alkyl group Chemical group 0.000 claims 43
- 239000000126 substance Substances 0.000 claims 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 9
- GLZXFITXXAMCRJ-UHFFFAOYSA-N azepin-4-one Chemical compound O=C1C=CC=NC=C1 GLZXFITXXAMCRJ-UHFFFAOYSA-N 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000004001 thioalkyl group Chemical group 0.000 claims 4
- MOXYYGKEQAGQLQ-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2COCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2COCC2)=NC=N3)=O)C=C1 MOXYYGKEQAGQLQ-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical compound C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- UMGAUDXFCWKGEF-UHFFFAOYSA-N 10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C12=NC=NN2C(=O)NC2=C1C=CS2 UMGAUDXFCWKGEF-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- HXZVLEPQCCBBTO-UHFFFAOYSA-N FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2COCC2)=NC=N3)=O)C=CC(=C1)OC Chemical compound FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2COCC2)=NC=N3)=O)C=CC(=C1)OC HXZVLEPQCCBBTO-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000002207 metabolite Substances 0.000 claims 2
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- IFNWESYYDINUHV-OLQVQODUSA-N (2s,6r)-2,6-dimethylpiperazine Chemical compound C[C@H]1CNC[C@@H](C)N1 IFNWESYYDINUHV-OLQVQODUSA-N 0.000 claims 1
- RFAPOGMFZTYBEW-UHFFFAOYSA-N 1,2,2-trimethylpiperazine Chemical compound CN1CCNCC1(C)C RFAPOGMFZTYBEW-UHFFFAOYSA-N 0.000 claims 1
- ARHYWWAJZDAYDJ-UHFFFAOYSA-N 1,2-dimethylpiperazine Chemical compound CC1CNCCN1C ARHYWWAJZDAYDJ-UHFFFAOYSA-N 0.000 claims 1
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 1
- TWJPZMYNUBAUGA-UHFFFAOYSA-N 1-(1,4-diazepan-1-yl)ethanone Chemical compound CC(=O)N1CCCNCC1 TWJPZMYNUBAUGA-UHFFFAOYSA-N 0.000 claims 1
- IVTZRJKKXSKXKO-UHFFFAOYSA-N 1-(2-fluorophenyl)piperazine Chemical compound FC1=CC=CC=C1N1CCNCC1 IVTZRJKKXSKXKO-UHFFFAOYSA-N 0.000 claims 1
- KIFCSMQTGWVMOD-UHFFFAOYSA-N 1-(3-fluorophenyl)piperazine Chemical compound FC1=CC=CC(N2CCNCC2)=C1 KIFCSMQTGWVMOD-UHFFFAOYSA-N 0.000 claims 1
- AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- SCGAVZGSIVHGPP-UHFFFAOYSA-N 1-ethylpiperazin-2-one Chemical compound CCN1CCNCC1=O SCGAVZGSIVHGPP-UHFFFAOYSA-N 0.000 claims 1
- ZZAKLGGGMWORRT-UHFFFAOYSA-N 1-methylsulfonylpiperazine Chemical compound CS(=O)(=O)N1CCNCC1 ZZAKLGGGMWORRT-UHFFFAOYSA-N 0.000 claims 1
- PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims 1
- WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 claims 1
- FCERXADALQBVMI-UHFFFAOYSA-N 11-[(2,2-difluoro-5-azaspiro[2.4]heptan-5-yl)methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound FC1(CC12CN(CC2)CC2=CC=1C=3N(C(N(C1S2)CC2=CC=C(C=C2)OC)=O)N=CN3)F FCERXADALQBVMI-UHFFFAOYSA-N 0.000 claims 1
- PKFRPYWHUPDFRP-UHFFFAOYSA-N 11-[(2,2-dimethylmorpholin-4-yl)methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CC(C)(C)OCC1)=C2 PKFRPYWHUPDFRP-UHFFFAOYSA-N 0.000 claims 1
- XCKBPBDVDNCKNT-UHFFFAOYSA-N 11-[(2,2-dimethylmorpholin-4-yl)methyl]-8-[(4-methoxyphenyl)methyl]-12-methyl-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CC(C)(C)OCC1)=C2C XCKBPBDVDNCKNT-UHFFFAOYSA-N 0.000 claims 1
- RLQYDIPTXSYJLZ-UHFFFAOYSA-N 11-[(4-acetyl-1,4-diazepan-1-yl)methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CCCN(CC4)C(C)=O)cc3c3ncnn3c2=O)cc1 RLQYDIPTXSYJLZ-UHFFFAOYSA-N 0.000 claims 1
- XPLOSUPPLOGKJB-UHFFFAOYSA-N 11-[(4-ethyl-3-oxopiperazin-1-yl)methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1C(=O)N(CC)CCN1CC(S1)=CC2=C1N(CC=1C=CC(OC)=CC=1)C(=O)N1N=CN=C12 XPLOSUPPLOGKJB-UHFFFAOYSA-N 0.000 claims 1
- PYUJMNICSBNTRJ-UHFFFAOYSA-N 11-[[(2,2-dimethyloxan-4-yl)-ethylamino]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound CCN(Cc1cc2c(s1)n(Cc1ccc(OC)cc1)c(=O)n1ncnc21)C1CCOC(C)(C)C1 PYUJMNICSBNTRJ-UHFFFAOYSA-N 0.000 claims 1
- PTGKOMCAGVDKDO-OKILXGFUSA-N 11-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(3-fluoro-4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)cc1F PTGKOMCAGVDKDO-OKILXGFUSA-N 0.000 claims 1
- NTIYYAAIFWMGJF-GASCZTMLSA-N 11-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1C[C@@H](C)O[C@@H](C)C1)=C2 NTIYYAAIFWMGJF-GASCZTMLSA-N 0.000 claims 1
- IGXFKTXSXXYESU-GASCZTMLSA-N 11-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(4-methoxyphenyl)methyl]-12-methyl-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1C[C@@H](C)O[C@@H](C)C1)=C2C IGXFKTXSXXYESU-GASCZTMLSA-N 0.000 claims 1
- XWXKXSSBWBEDIU-OKILXGFUSA-N 11-[[(2S,6R)-2,6-dimethylmorpholin-4-yl]methyl]-8-[(2-fluoro-4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(F)c1 XWXKXSSBWBEDIU-OKILXGFUSA-N 0.000 claims 1
- VJFCCYJQIDZNPT-UHFFFAOYSA-N 11-[[3-(2-fluorophenoxy)azetidin-1-yl]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CC(C4)Oc4ccccc4F)cc3c3ncnn3c2=O)cc1 VJFCCYJQIDZNPT-UHFFFAOYSA-N 0.000 claims 1
- NKDJIZYLNHNUHI-UHFFFAOYSA-N 11-[[4-(2-fluorophenyl)piperazin-1-yl]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CCN(CC4)c4ccccc4F)cc3c3ncnn3c2=O)cc1 NKDJIZYLNHNUHI-UHFFFAOYSA-N 0.000 claims 1
- YQVDRGAUOCOWFA-UHFFFAOYSA-N 11-[[4-(3-fluorophenyl)piperazin-1-yl]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CCN(CC4)c4cccc(F)c4)cc3c3ncnn3c2=O)cc1 YQVDRGAUOCOWFA-UHFFFAOYSA-N 0.000 claims 1
- PHRBZWNIFIAPMZ-UHFFFAOYSA-N 11-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CCN(CC4)c4ccc(F)cc4)cc3c3ncnn3c2=O)cc1 PHRBZWNIFIAPMZ-UHFFFAOYSA-N 0.000 claims 1
- YCVAKHOUZFMOKP-UHFFFAOYSA-N 12-[[3-(hydroxymethyl)-3-(2-methylpropyl)piperidin-1-yl]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3scc(CN4CCCC(CO)(CC(C)C)C4)c3c3ncnn3c2=O)cc1 YCVAKHOUZFMOKP-UHFFFAOYSA-N 0.000 claims 1
- SQRPEYWZFOVFCF-UHFFFAOYSA-N 12-[[di(propan-2-yl)amino]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3scc(CN(C(C)C)C(C)C)c3c3ncnn3c2=O)cc1 SQRPEYWZFOVFCF-UHFFFAOYSA-N 0.000 claims 1
- GQJFPQOEFNWXRS-UHFFFAOYSA-N 12-[[ethyl(oxan-4-ylmethyl)amino]methyl]-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound CCN(CC1CCOCC1)Cc1csc2n(Cc3ccc(OC)cc3)c(=O)n3ncnc3c12 GQJFPQOEFNWXRS-UHFFFAOYSA-N 0.000 claims 1
- ONYFFKRZGFBNJU-UHFFFAOYSA-N 15,15-difluoro-8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8,13-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound FC1(CNCC2=C1C=1C=3N(C(N(C1S2)CC2=CC=C(C=C2)OC)=O)N=CN3)F ONYFFKRZGFBNJU-UHFFFAOYSA-N 0.000 claims 1
- HKGBBVNWBZRMAL-UHFFFAOYSA-N 15,15-difluoro-8-[(4-methoxyphenyl)methyl]-13-(2-methylpropyl)-10-thia-3,5,6,8,13-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound FC1(CN(CC2=C1C=1C=3N(C(N(C1S2)CC2=CC=C(C=C2)OC)=O)N=CN3)CC(C)C)F HKGBBVNWBZRMAL-UHFFFAOYSA-N 0.000 claims 1
- LYJSPCIIWWKSML-UHFFFAOYSA-N 15,15-difluoro-8-[(4-methoxyphenyl)methyl]-13-(oxan-4-ylmethyl)-10-thia-3,5,6,8,13-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2C(F)(F)CN(CC2CCOCC2)C1 LYJSPCIIWWKSML-UHFFFAOYSA-N 0.000 claims 1
- AMKKJOJODSUMDI-UHFFFAOYSA-N 2,2-difluoro-5-azaspiro[2.4]heptane Chemical compound FC1(F)CC11CNCC1 AMKKJOJODSUMDI-UHFFFAOYSA-N 0.000 claims 1
- UFLFSJVTFSZTKX-UHFFFAOYSA-N 2,2-dimethylmorpholine Chemical compound CC1(C)CNCCO1 UFLFSJVTFSZTKX-UHFFFAOYSA-N 0.000 claims 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims 1
- CHPRFKYDQRKRRK-UHFFFAOYSA-N 2-(methoxymethyl)pyrrolidine Chemical compound COCC1CCCN1 CHPRFKYDQRKRRK-UHFFFAOYSA-N 0.000 claims 1
- RGNFMQJLAOONTP-UHFFFAOYSA-N 2-ethylmorpholine Chemical compound CCC1CNCCO1 RGNFMQJLAOONTP-UHFFFAOYSA-N 0.000 claims 1
- LQMMFVPUIVBYII-UHFFFAOYSA-N 2-methylmorpholine Chemical compound CC1CNCCO1 LQMMFVPUIVBYII-UHFFFAOYSA-N 0.000 claims 1
- DIQOUXNTSMWQSA-UHFFFAOYSA-N 2-oxa-5-azabicyclo[2.2.1]heptane Chemical compound C1OC2CNC1C2 DIQOUXNTSMWQSA-UHFFFAOYSA-N 0.000 claims 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- BJPFEMLBDNVRDZ-UHFFFAOYSA-N 3-(2-fluorophenoxy)azetidine Chemical compound FC1=CC=CC=C1OC1CNC1 BJPFEMLBDNVRDZ-UHFFFAOYSA-N 0.000 claims 1
- SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 claims 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
- YYBXNWIRMJXEQJ-UHFFFAOYSA-N 4-piperidin-4-ylmorpholine Chemical compound C1CNCCC1N1CCOCC1 YYBXNWIRMJXEQJ-UHFFFAOYSA-N 0.000 claims 1
- UNKDCRUEJJZIIB-UHFFFAOYSA-N 4-piperidin-4-yloxypyridine Chemical compound C1CNCCC1OC1=CC=NC=C1 UNKDCRUEJJZIIB-UHFFFAOYSA-N 0.000 claims 1
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims 1
- WPXDGBOUSNURDA-UHFFFAOYSA-N 6,7-dihydro-1H-triazolo[1,5-c]pyrimidin-5-one Chemical compound N1N=CC=2N1CNC(C2)=O WPXDGBOUSNURDA-UHFFFAOYSA-N 0.000 claims 1
- MYKOUVIRYZPGCV-UHFFFAOYSA-N 6-(4-chlorobenzyl)-8,9,10,11-tetrahydropyrido[4',3':4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6h)-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCNC1 MYKOUVIRYZPGCV-UHFFFAOYSA-N 0.000 claims 1
- VXDFTBUHLLVVCZ-UHFFFAOYSA-N 6-(4-chlorobenzyl)-9-benzyl-8,9,10,11-tetrahydropyrido[4',3':4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6h)-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(CC=2C=CC=CC=2)C1 VXDFTBUHLLVVCZ-UHFFFAOYSA-N 0.000 claims 1
- YKZMTBOJYHNJHA-UHFFFAOYSA-N 6-(4-methoxybenzyl)-9-methylthieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6h)-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC=C2C YKZMTBOJYHNJHA-UHFFFAOYSA-N 0.000 claims 1
- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 claims 1
- OGIUFWUWTNIJSU-UHFFFAOYSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-11-(1,4-oxazepan-4-ylmethyl)-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CCCOCC4)cc3c3ncnn3c2=O)c(F)c1F OGIUFWUWTNIJSU-UHFFFAOYSA-N 0.000 claims 1
- JRJKJTUTUITCJQ-UHFFFAOYSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-11-[(3-hydroxyazetidin-1-yl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CC(O)C4)cc3c3ncnn3c2=O)c(F)c1F JRJKJTUTUITCJQ-UHFFFAOYSA-N 0.000 claims 1
- HJQHBCRNCDYCNA-UHFFFAOYSA-N 8-[(2,3-difluoro-4-methoxyphenyl)methyl]-11-[[methyl-[(3-methyloxetan-3-yl)methyl]amino]methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN(C)CC4(C)COC4)cc3c3ncnn3c2=O)c(F)c1F HJQHBCRNCDYCNA-UHFFFAOYSA-N 0.000 claims 1
- FUSXGVSIUUIDIZ-UHFFFAOYSA-N 8-[(2-fluoro-4-methoxyphenyl)methyl]-11-[(3-hydroxyazetidin-1-yl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CC(O)C4)cc3c3ncnn3c2=O)c(F)c1 FUSXGVSIUUIDIZ-UHFFFAOYSA-N 0.000 claims 1
- FOZFBBKUKXGMND-UHFFFAOYSA-N 8-[(2-fluoro-4-methoxyphenyl)methyl]-13-(oxan-4-ylmethyl)-10-thia-3,5,6,8,13-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound FC1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(CC2CCOCC2)C1 FOZFBBKUKXGMND-UHFFFAOYSA-N 0.000 claims 1
- CRJROJCTKLILAY-BETUJISGSA-N 8-[(3-chloro-4-fluorophenyl)methyl]-11-[[(2R,6S)-2,6-dimethylmorpholin-4-yl]methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C[C@H]1CN(Cc2cc3c(s2)n(Cc2ccc(F)c(Cl)c2)c(=O)n2ncnc32)C[C@@H](C)O1 CRJROJCTKLILAY-BETUJISGSA-N 0.000 claims 1
- IDTOXCSJPHTASJ-UHFFFAOYSA-N 8-[(4-chlorophenyl)methyl]-13-(oxan-4-ylmethyl)-10-thia-3,5,6,8,13-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(CC2CCOCC2)C1 IDTOXCSJPHTASJ-UHFFFAOYSA-N 0.000 claims 1
- OCIONBIYKSRJEQ-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8,12-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2)=NC=N3)=O)C=C1 OCIONBIYKSRJEQ-UHFFFAOYSA-N 0.000 claims 1
- SHPGAXMVMAZQHZ-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8,13-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCNC1 SHPGAXMVMAZQHZ-UHFFFAOYSA-N 0.000 claims 1
- VQOGETOACCVRJC-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-10-thia-3,5,6,8,14-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CNCC2)=NC=N3)=O)C=C1 VQOGETOACCVRJC-UHFFFAOYSA-N 0.000 claims 1
- QMCNORGJOSNNGX-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-(2-oxa-7-azaspiro[3.5]nonan-7-ylmethyl)-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCC3(COC3)CC1)=C2 QMCNORGJOSNNGX-UHFFFAOYSA-N 0.000 claims 1
- OMLGJDGTSASRIX-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-(7-oxa-2-azaspiro[3.5]nonan-2-ylmethyl)-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CC3(C1)CCOCC3)=C2 OMLGJDGTSASRIX-UHFFFAOYSA-N 0.000 claims 1
- XXXXKQKGQGTKGC-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-(morpholin-4-ylmethyl)-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCOCC1)=C2 XXXXKQKGQGTKGC-UHFFFAOYSA-N 0.000 claims 1
- UUVLSPFIRUMMMJ-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-[(4-methylsulfonylpiperazin-1-yl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCN(CC1)S(C)(=O)=O)=C2 UUVLSPFIRUMMMJ-UHFFFAOYSA-N 0.000 claims 1
- AMKCZFYYGNUXMO-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-[(4-morpholin-4-ylpiperidin-1-yl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CCC(CC4)N4CCOCC4)cc3c3ncnn3c2=O)cc1 AMKCZFYYGNUXMO-UHFFFAOYSA-N 0.000 claims 1
- KDZMWVHVOMQCHJ-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-11-[(4-pyridin-4-yloxypiperidin-1-yl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3sc(CN4CCC(CC4)Oc4ccncc4)cc3c3ncnn3c2=O)cc1 KDZMWVHVOMQCHJ-UHFFFAOYSA-N 0.000 claims 1
- BRBRGARFDJFTNA-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-[(3-phenoxypyrrolidin-1-yl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3scc(CN4CCC(C4)Oc4ccccc4)c3c3ncnn3c2=O)cc1 BRBRGARFDJFTNA-UHFFFAOYSA-N 0.000 claims 1
- VSKCACVTROOONH-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-[[methyl(oxan-4-ylmethyl)amino]methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound COc1ccc(Cn2c3scc(CN(C)CC4CCOCC4)c3c3ncnn3c2=O)cc1 VSKCACVTROOONH-UHFFFAOYSA-N 0.000 claims 1
- RSFXDARWDHAYSY-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-methyl-11-(morpholin-4-ylmethyl)-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCOCC1)=C2C RSFXDARWDHAYSY-UHFFFAOYSA-N 0.000 claims 1
- VGWWVZFFYNRKCX-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-methyl-11-[(4-methylpiperazin-1-yl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCN(C)CC1)=C2C VGWWVZFFYNRKCX-UHFFFAOYSA-N 0.000 claims 1
- CJFCNJUXSGZUNC-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-12-methyl-11-[(4-methylsulfonylpiperazin-1-yl)methyl]-10-thia-3,5,6,8-tetrazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,11-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCN(CC1)S(C)(=O)=O)=C2C CJFCNJUXSGZUNC-UHFFFAOYSA-N 0.000 claims 1
- BQOIGGMSKKKZRK-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-13-(oxan-4-ylmethyl)-10-thia-3,5,6,8,13-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(CC2CCOCC2)C1 BQOIGGMSKKKZRK-UHFFFAOYSA-N 0.000 claims 1
- ZCGVQRHIBAZEPG-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-13-[(5-methyl-1,3,4-thiadiazol-2-yl)methyl]-10-thia-3,5,6,8,13-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(CC=2SC(C)=NN=2)C1 ZCGVQRHIBAZEPG-UHFFFAOYSA-N 0.000 claims 1
- KIBTWBYZVQEYBB-UHFFFAOYSA-N 8-[(4-methoxyphenyl)methyl]-14-(oxan-4-ylmethyl)-10-thia-3,5,6,8,14-pentazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,11(16)-tetraen-7-one Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CN(CC2)CC2CCOCC2)=NC=N3)=O)C=C1 KIBTWBYZVQEYBB-UHFFFAOYSA-N 0.000 claims 1
- POOPWPIOIMBTOH-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1O2 POOPWPIOIMBTOH-UHFFFAOYSA-N 0.000 claims 1
- GGYYLWAVOQXCML-UHFFFAOYSA-N C(C)OC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1 Chemical compound C(C)OC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1 GGYYLWAVOQXCML-UHFFFAOYSA-N 0.000 claims 1
- QGJLXKVVJWINHV-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)N1CCCC2=C1SC1=C2C=2N(C(N1CC1=CC(=C(C=C1)OC)OC)=O)N=CN2 Chemical compound C(C1=CC=CC=C1)(=O)N1CCCC2=C1SC1=C2C=2N(C(N1CC1=CC(=C(C=C1)OC)OC)=O)N=CN2 QGJLXKVVJWINHV-UHFFFAOYSA-N 0.000 claims 1
- UPXWPIHSRBNSTO-UHFFFAOYSA-N C(C1=CC=CC=C1)N1C(N2C(C3=C1SC1=C3CCCC1)=NC=N2)=O Chemical compound C(C1=CC=CC=C1)N1C(N2C(C3=C1SC1=C3CCCC1)=NC=N2)=O UPXWPIHSRBNSTO-UHFFFAOYSA-N 0.000 claims 1
- ZTZWPLIGKXUGEZ-UHFFFAOYSA-N C1(=CC=C(C=C1)CN1C(N2C(C3=C1SC(=C3)C)=NC=N2)=O)C2=CC=CC=C2 Chemical compound C1(=CC=C(C=C1)CN1C(N2C(C3=C1SC(=C3)C)=NC=N2)=O)C2=CC=CC=C2 ZTZWPLIGKXUGEZ-UHFFFAOYSA-N 0.000 claims 1
- AHCYLQBRMYWODR-UHFFFAOYSA-N C1(=CC=C(C=C1)CN1C(N2C(C3=C1SC(=C3)CC3=CC=CC=C3)=NC=N2)=O)C2=CC=CC=C2 Chemical compound C1(=CC=C(C=C1)CN1C(N2C(C3=C1SC(=C3)CC3=CC=CC=C3)=NC=N2)=O)C2=CC=CC=C2 AHCYLQBRMYWODR-UHFFFAOYSA-N 0.000 claims 1
- IDYZHJSVCPZQLL-UHFFFAOYSA-N C1(=CC=C(C=C1)CN1C(N2C(C3=C1SC1=C3CCCC1)=NC=N2)=O)C2=CC=CC=C2 Chemical compound C1(=CC=C(C=C1)CN1C(N2C(C3=C1SC1=C3CCCC1)=NC=N2)=O)C2=CC=CC=C2 IDYZHJSVCPZQLL-UHFFFAOYSA-N 0.000 claims 1
- MVAVPTWYQNOMHZ-UHFFFAOYSA-N C1(=CC=C(C=C1)CN1C(N2C(C3=C1SC=C3C)=NC=N2)=O)C2=CC=CC=C2 Chemical compound C1(=CC=C(C=C1)CN1C(N2C(C3=C1SC=C3C)=NC=N2)=O)C2=CC=CC=C2 MVAVPTWYQNOMHZ-UHFFFAOYSA-N 0.000 claims 1
- QPTFIKYNYFIRHU-UHFFFAOYSA-N C1(CC1)C(=O)N1CC2=C(C=3C=4N(C(N(C3S2)CC2=C(C=C(C=C2)OC)F)=O)N=CN4)CC1 Chemical compound C1(CC1)C(=O)N1CC2=C(C=3C=4N(C(N(C3S2)CC2=C(C=C(C=C2)OC)F)=O)N=CN4)CC1 QPTFIKYNYFIRHU-UHFFFAOYSA-N 0.000 claims 1
- IGQTXZGNQVGIDF-UHFFFAOYSA-N C1(CC1)C(=O)N1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1 Chemical compound C1(CC1)C(=O)N1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1 IGQTXZGNQVGIDF-UHFFFAOYSA-N 0.000 claims 1
- ZZMAHWVXPKOISS-UHFFFAOYSA-N C1(CC1)CN1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1 Chemical compound C1(CC1)CN1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1 ZZMAHWVXPKOISS-UHFFFAOYSA-N 0.000 claims 1
- DOOMVGKASLRWHP-UHFFFAOYSA-N C1=CC(Cl)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(C(=O)C=2N=CC=NC=2)C1 Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(C(=O)C=2N=CC=NC=2)C1 DOOMVGKASLRWHP-UHFFFAOYSA-N 0.000 claims 1
- VOFWYPSRCNVWHC-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CC=C2C2=C1SC(CN1CCOCC1)=C2 Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CC=C2C2=C1SC(CN1CCOCC1)=C2 VOFWYPSRCNVWHC-UHFFFAOYSA-N 0.000 claims 1
- SXMULLONNJPKMD-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(Br)=C2C Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(Br)=C2C SXMULLONNJPKMD-UHFFFAOYSA-N 0.000 claims 1
- DSGFRMTXYJCZCO-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(C=1N(N=C(C=1)C(F)(F)F)C)=C2 Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(C=1N(N=C(C=1)C(F)(F)F)C)=C2 DSGFRMTXYJCZCO-UHFFFAOYSA-N 0.000 claims 1
- HQVWPNDKRKECEE-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCCC1)=C2C Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCCC1)=C2C HQVWPNDKRKECEE-UHFFFAOYSA-N 0.000 claims 1
- YNBFSZRGQWYVKW-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCOCCC1)=C2 Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CN1CCOCCC1)=C2 YNBFSZRGQWYVKW-UHFFFAOYSA-N 0.000 claims 1
- NNBWDMZZJVBETD-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CO)=C2C Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC(CO)=C2C NNBWDMZZJVBETD-UHFFFAOYSA-N 0.000 claims 1
- CFUHRLVGDJBOFY-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(C(=O)OC(C)(C)C)C1 Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(C(=O)OC(C)(C)C)C1 CFUHRLVGDJBOFY-UHFFFAOYSA-N 0.000 claims 1
- XMGSTLRVMCSGES-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(C=2N=CC=CC=2)C1 Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(C=2N=CC=CC=2)C1 XMGSTLRVMCSGES-UHFFFAOYSA-N 0.000 claims 1
- JLCSCIZFPJNSHD-UHFFFAOYSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(CC2OCCNC2)C1 Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCN(CC2OCCNC2)C1 JLCSCIZFPJNSHD-UHFFFAOYSA-N 0.000 claims 1
- VCEXQGYAKQSDFT-GASCZTMLSA-N C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC=C2CN1C[C@@H](C)O[C@@H](C)C1 Chemical compound C1=CC(OC)=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC=C2CN1C[C@@H](C)O[C@@H](C)C1 VCEXQGYAKQSDFT-GASCZTMLSA-N 0.000 claims 1
- AXPVGJNPJSMCLA-UHFFFAOYSA-N C1N(C)CCC(C=2C3=NC=NN3C3=O)=C1SC=2N3CC1=CC=C(Cl)C=C1 Chemical compound C1N(C)CCC(C=2C3=NC=NN3C3=O)=C1SC=2N3CC1=CC=C(Cl)C=C1 AXPVGJNPJSMCLA-UHFFFAOYSA-N 0.000 claims 1
- LWDNEIWBMXZMGB-SFHVURJKSA-N C1[C@H]2N(CCN1CC1=C(C=3C=4N(C(N(C3S1)CC1=CC=C(C=C1)OC)=O)N=CN4)C)CCC2 Chemical compound C1[C@H]2N(CCN1CC1=C(C=3C=4N(C(N(C3S1)CC1=CC=C(C=C1)OC)=O)N=CN4)C)CCC2 LWDNEIWBMXZMGB-SFHVURJKSA-N 0.000 claims 1
- HHOIINRJWQWHOF-UHFFFAOYSA-N CC(C)CCc1cc2c(s1)n(Cc1ccc(Cl)cc1)c(=O)n1ncnc21 Chemical compound CC(C)CCc1cc2c(s1)n(Cc1ccc(Cl)cc1)c(=O)n1ncnc21 HHOIINRJWQWHOF-UHFFFAOYSA-N 0.000 claims 1
- XNPUJCYRXRJEME-UHFFFAOYSA-N CC(C)CCc1cc2c(s1)n(Cc1cccc(Cl)c1)c(=O)n1ncnc21 Chemical compound CC(C)CCc1cc2c(s1)n(Cc1cccc(Cl)c1)c(=O)n1ncnc21 XNPUJCYRXRJEME-UHFFFAOYSA-N 0.000 claims 1
- NVAMAYJVRMBCIS-UHFFFAOYSA-N CC(C)CCc1cc2c(s1)n(Cc1ccccc1Cl)c(=O)n1ncnc21 Chemical compound CC(C)CCc1cc2c(s1)n(Cc1ccccc1Cl)c(=O)n1ncnc21 NVAMAYJVRMBCIS-UHFFFAOYSA-N 0.000 claims 1
- KDMBLSDUPJJLBB-UHFFFAOYSA-N CC(C)CCc1cc2c3ncnn3c(=O)n(Cc3ccc(cc3)-c3ccccc3)c2s1 Chemical compound CC(C)CCc1cc2c3ncnn3c(=O)n(Cc3ccc(cc3)-c3ccccc3)c2s1 KDMBLSDUPJJLBB-UHFFFAOYSA-N 0.000 claims 1
- LWTLQBGRUTUGAZ-UHFFFAOYSA-N CC(C)CCc1cc2c3ncnn3c(=O)n(Cc3ccccc3)c2s1 Chemical compound CC(C)CCc1cc2c3ncnn3c(=O)n(Cc3ccccc3)c2s1 LWTLQBGRUTUGAZ-UHFFFAOYSA-N 0.000 claims 1
- GWRNATXQNKVNCT-UHFFFAOYSA-N CCN1CCN(Cc2sc3n(Cc4ccc(OC)cc4)c(=O)n4ncnc4c3c2C)CC1=O Chemical compound CCN1CCN(Cc2sc3n(Cc4ccc(OC)cc4)c(=O)n4ncnc4c3c2C)CC1=O GWRNATXQNKVNCT-UHFFFAOYSA-N 0.000 claims 1
- SZJGBEYYBHAJTB-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2C(=O)C2COCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2C(=O)C2COCC2)=NC=N3)=O)C=C1 SZJGBEYYBHAJTB-UHFFFAOYSA-N 0.000 claims 1
- KETMFKWAMXNOIW-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2CC2CCOCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2CC2CCOCC2)=NC=N3)=O)C=C1 KETMFKWAMXNOIW-UHFFFAOYSA-N 0.000 claims 1
- WXFVOFKSOUEYNT-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2CC2COCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2CC2COCC2)=NC=N3)=O)C=C1 WXFVOFKSOUEYNT-UHFFFAOYSA-N 0.000 claims 1
- HJWYWRQHSOPYSO-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2CC2COCCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCCN2CC2COCCC2)=NC=N3)=O)C=C1 HJWYWRQHSOPYSO-UHFFFAOYSA-N 0.000 claims 1
- JRHZEOAYYYPWDQ-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2CN(CC2)C)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2CN(CC2)C)=NC=N3)=O)C=C1 JRHZEOAYYYPWDQ-UHFFFAOYSA-N 0.000 claims 1
- LRRTUSKWLLJCEV-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2CNCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2CNCC2)=NC=N3)=O)C=C1 LRRTUSKWLLJCEV-UHFFFAOYSA-N 0.000 claims 1
- MOXYYGKEQAGQLQ-OAHLLOKOSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)[C@H]2COCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)[C@H]2COCC2)=NC=N3)=O)C=C1 MOXYYGKEQAGQLQ-OAHLLOKOSA-N 0.000 claims 1
- IBQSPUJNBUZFTM-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC(C)(C)C)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC(C)(C)C)=NC=N3)=O)C=C1 IBQSPUJNBUZFTM-UHFFFAOYSA-N 0.000 claims 1
- WZYMEOJEUDPUNG-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2(COC2)C)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2(COC2)C)=NC=N3)=O)C=C1 WZYMEOJEUDPUNG-UHFFFAOYSA-N 0.000 claims 1
- ZFPZSRYDZKCTQP-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=C(N=CS2)C)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=C(N=CS2)C)=NC=N3)=O)C=C1 ZFPZSRYDZKCTQP-UHFFFAOYSA-N 0.000 claims 1
- OKTDGJZRHBDOSL-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=CC=NC=C2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=CC=NC=C2)=NC=N3)=O)C=C1 OKTDGJZRHBDOSL-UHFFFAOYSA-N 0.000 claims 1
- FDYDHXXSOYBULH-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=C2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=C2)=NC=N3)=O)C=C1 FDYDHXXSOYBULH-UHFFFAOYSA-N 0.000 claims 1
- QXNUCIQEADCRLV-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=N2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=N2)=NC=N3)=O)C=C1 QXNUCIQEADCRLV-UHFFFAOYSA-N 0.000 claims 1
- XBCGEXNUHKXQDA-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=NC=C2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=NC=C2)=NC=N3)=O)C=C1 XBCGEXNUHKXQDA-UHFFFAOYSA-N 0.000 claims 1
- AJJCTLFRMWLOSQ-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2CCNCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2CCNCC2)=NC=N3)=O)C=C1 AJJCTLFRMWLOSQ-UHFFFAOYSA-N 0.000 claims 1
- GNTQEEGBMYWXON-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2COCCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2COCCC2)=NC=N3)=O)C=C1 GNTQEEGBMYWXON-UHFFFAOYSA-N 0.000 claims 1
- OPRBUEDTVKPTHM-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2OC(CC2)=O)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2OC(CC2)=O)=NC=N3)=O)C=C1 OPRBUEDTVKPTHM-UHFFFAOYSA-N 0.000 claims 1
- XHSLSWWMZQUNSC-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2OCCCC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2OCCCC2)=NC=N3)=O)C=C1 XHSLSWWMZQUNSC-UHFFFAOYSA-N 0.000 claims 1
- OTMHFDCPVQCROD-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC=2N(C=CN2)C)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC=2N(C=CN2)C)=NC=N3)=O)C=C1 OTMHFDCPVQCROD-UHFFFAOYSA-N 0.000 claims 1
- PKKIWMPURJCDPH-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CCCS(=O)(=O)C)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CCCS(=O)(=O)C)=NC=N3)=O)C=C1 PKKIWMPURJCDPH-UHFFFAOYSA-N 0.000 claims 1
- GFPNUIUXEODPLE-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)S(=O)(=O)C)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)S(=O)(=O)C)=NC=N3)=O)C=C1 GFPNUIUXEODPLE-UHFFFAOYSA-N 0.000 claims 1
- GORLOHJYLZILHO-UHFFFAOYSA-N COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1 Chemical compound COC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1 GORLOHJYLZILHO-UHFFFAOYSA-N 0.000 claims 1
- HTVNUXROSDMKAF-UHFFFAOYSA-N COC=1C=C(CN2C(N3C(C4=C2SC2=C4CCCN2)=NC=N3)=O)C=CC1OC Chemical compound COC=1C=C(CN2C(N3C(C4=C2SC2=C4CCCN2)=NC=N3)=O)C=CC1OC HTVNUXROSDMKAF-UHFFFAOYSA-N 0.000 claims 1
- XCWKALHWBDBIKK-KRWDZBQOSA-N COC[C@@H]1CCCN1Cc1sc2n(Cc3ccc(OC)cc3)c(=O)n3ncnc3c2c1C Chemical compound COC[C@@H]1CCCN1Cc1sc2n(Cc3ccc(OC)cc3)c(=O)n3ncnc3c2c1C XCWKALHWBDBIKK-KRWDZBQOSA-N 0.000 claims 1
- PPVLOQNFNFUCKX-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(C)C)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN(C)C)c(C)c3c3ncnn3c2=O)cc1 PPVLOQNFNFUCKX-UHFFFAOYSA-N 0.000 claims 1
- IRSQBXOETDHBRO-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(C)C)cc3c3ncnn3c2=O)c(F)c1F Chemical compound COc1ccc(Cn2c3sc(CN(C)C)cc3c3ncnn3c2=O)c(F)c1F IRSQBXOETDHBRO-UHFFFAOYSA-N 0.000 claims 1
- UMTKROZJIGITBI-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(C)C)cc3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN(C)C)cc3c3ncnn3c2=O)cc1 UMTKROZJIGITBI-UHFFFAOYSA-N 0.000 claims 1
- OHLNQUUHUMHKIH-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(C)C4CC4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN(C)C4CC4)c(C)c3c3ncnn3c2=O)cc1 OHLNQUUHUMHKIH-UHFFFAOYSA-N 0.000 claims 1
- HKGVNPAOJBYVEN-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(C)C4CCOCC4)cc3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN(C)C4CCOCC4)cc3c3ncnn3c2=O)cc1 HKGVNPAOJBYVEN-UHFFFAOYSA-N 0.000 claims 1
- KYTGPDAJJXPRTR-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(C)CC(=O)N(C)C)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN(C)CC(=O)N(C)C)c(C)c3c3ncnn3c2=O)cc1 KYTGPDAJJXPRTR-UHFFFAOYSA-N 0.000 claims 1
- NDCYLLYWYYUZHH-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(C)CC4CCCO4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN(C)CC4CCCO4)c(C)c3c3ncnn3c2=O)cc1 NDCYLLYWYYUZHH-UHFFFAOYSA-N 0.000 claims 1
- FYGPLJNIUXDWFV-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(C)CC4CCOC4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN(C)CC4CCOC4)c(C)c3c3ncnn3c2=O)cc1 FYGPLJNIUXDWFV-UHFFFAOYSA-N 0.000 claims 1
- ZQFXRZZVWMMAIT-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN(CCO)Cc4ccccc4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN(CCO)Cc4ccccc4)c(C)c3c3ncnn3c2=O)cc1 ZQFXRZZVWMMAIT-UHFFFAOYSA-N 0.000 claims 1
- FSPVQEKTRMLNAY-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CC5CC4CO5)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CC5CC4CO5)c(C)c3c3ncnn3c2=O)cc1 FSPVQEKTRMLNAY-UHFFFAOYSA-N 0.000 claims 1
- XISUKJTWWXHPKH-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CC5CC4CO5)cc3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CC5CC4CO5)cc3c3ncnn3c2=O)cc1 XISUKJTWWXHPKH-UHFFFAOYSA-N 0.000 claims 1
- BSAVECNSARKZIM-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CC5CCC(C4)O5)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CC5CCC(C4)O5)c(C)c3c3ncnn3c2=O)cc1 BSAVECNSARKZIM-UHFFFAOYSA-N 0.000 claims 1
- CCIZLYAPHABSBK-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCC(O)CC4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCC(O)CC4)c(C)c3c3ncnn3c2=O)cc1 CCIZLYAPHABSBK-UHFFFAOYSA-N 0.000 claims 1
- XTXQFFAWVVRIHG-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCN(C)C(C)(C)C4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCN(C)C(C)(C)C4)c(C)c3c3ncnn3c2=O)cc1 XTXQFFAWVVRIHG-UHFFFAOYSA-N 0.000 claims 1
- HPAKMLVKNNNIGG-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCN(C)C(C)C4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCN(C)C(C)C4)c(C)c3c3ncnn3c2=O)cc1 HPAKMLVKNNNIGG-UHFFFAOYSA-N 0.000 claims 1
- AJFIMLGRQGUDAI-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCN(C)CC4)cc3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCN(C)CC4)cc3c3ncnn3c2=O)cc1 AJFIMLGRQGUDAI-UHFFFAOYSA-N 0.000 claims 1
- LNUYYLUYXVAUEJ-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCN(CC4)C(C)=O)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCN(CC4)C(C)=O)c(C)c3c3ncnn3c2=O)cc1 LNUYYLUYXVAUEJ-UHFFFAOYSA-N 0.000 claims 1
- BXXJBQXXEAEFIZ-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCN(CC4)C(C)C)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCN(CC4)C(C)C)c(C)c3c3ncnn3c2=O)cc1 BXXJBQXXEAEFIZ-UHFFFAOYSA-N 0.000 claims 1
- HDNTXBRMYBWKLR-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCN5C(COC5=O)C4)cc3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCN5C(COC5=O)C4)cc3c3ncnn3c2=O)cc1 HDNTXBRMYBWKLR-UHFFFAOYSA-N 0.000 claims 1
- PWFPBRSOHLTLAA-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCNC(=O)C4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCNC(=O)C4)c(C)c3c3ncnn3c2=O)cc1 PWFPBRSOHLTLAA-UHFFFAOYSA-N 0.000 claims 1
- VALXAWCBIMKNHR-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCNCC4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCNCC4)c(C)c3c3ncnn3c2=O)cc1 VALXAWCBIMKNHR-UHFFFAOYSA-N 0.000 claims 1
- BDXSHVYLINGYGV-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCOC(C)C4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCOC(C)C4)c(C)c3c3ncnn3c2=O)cc1 BDXSHVYLINGYGV-UHFFFAOYSA-N 0.000 claims 1
- NLPSBXRSPRVYQZ-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCOCC4)cc3c3ncnn3c2=O)c(F)c1 Chemical compound COc1ccc(Cn2c3sc(CN4CCOCC4)cc3c3ncnn3c2=O)c(F)c1 NLPSBXRSPRVYQZ-UHFFFAOYSA-N 0.000 claims 1
- SVRFDWBSJSUTKT-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCOCC4)cc3c3ncnn3c2=O)cc1F Chemical compound COc1ccc(Cn2c3sc(CN4CCOCC4)cc3c3ncnn3c2=O)cc1F SVRFDWBSJSUTKT-UHFFFAOYSA-N 0.000 claims 1
- IWQXPVVCHAMXSM-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4CCOCC4C)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4CCOCC4C)c(C)c3c3ncnn3c2=O)cc1 IWQXPVVCHAMXSM-UHFFFAOYSA-N 0.000 claims 1
- FMZSFAPMKBFABQ-GASCZTMLSA-N COc1ccc(Cn2c3sc(CN4C[C@H](C)N[C@H](C)C4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4C[C@H](C)N[C@H](C)C4)c(C)c3c3ncnn3c2=O)cc1 FMZSFAPMKBFABQ-GASCZTMLSA-N 0.000 claims 1
- ZTQSSUCPIDRHNB-BETUJISGSA-N COc1ccc(Cn2c3sc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(F)c1F Chemical compound COc1ccc(Cn2c3sc(CN4C[C@H](C)O[C@H](C)C4)cc3c3ncnn3c2=O)c(F)c1F ZTQSSUCPIDRHNB-BETUJISGSA-N 0.000 claims 1
- NQJVSNWUJKSBCA-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CN4Cc5ccccc5C4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CN4Cc5ccccc5C4)c(C)c3c3ncnn3c2=O)cc1 NQJVSNWUJKSBCA-UHFFFAOYSA-N 0.000 claims 1
- IGEWQFAZQLRPTL-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CNC4CC4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CNC4CC4)c(C)c3c3ncnn3c2=O)cc1 IGEWQFAZQLRPTL-UHFFFAOYSA-N 0.000 claims 1
- BSHKYVYWANSUQP-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CNCC4(C)COC4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CNCC4(C)COC4)c(C)c3c3ncnn3c2=O)cc1 BSHKYVYWANSUQP-UHFFFAOYSA-N 0.000 claims 1
- FPBVWFDXCDHTBP-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CNCC4(C)COC4)cc3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CNCC4(C)COC4)cc3c3ncnn3c2=O)cc1 FPBVWFDXCDHTBP-UHFFFAOYSA-N 0.000 claims 1
- FATOHHQXIOSXNB-UHFFFAOYSA-N COc1ccc(Cn2c3sc(CNCc4cccnc4)c(C)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc(CNCc4cccnc4)c(C)c3c3ncnn3c2=O)cc1 FATOHHQXIOSXNB-UHFFFAOYSA-N 0.000 claims 1
- LBNBGOUWBHZXCA-UHFFFAOYSA-N COc1ccc(Cn2c3sc(cc3c3ncnn3c2=O)-c2c(C)noc2C)cc1 Chemical compound COc1ccc(Cn2c3sc(cc3c3ncnn3c2=O)-c2c(C)noc2C)cc1 LBNBGOUWBHZXCA-UHFFFAOYSA-N 0.000 claims 1
- ANEODGSBULPLDD-UHFFFAOYSA-N COc1ccc(Cn2c3sc4CN(CC5CCOC5)CCc4c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sc4CN(CC5CCOC5)CCc4c3c3ncnn3c2=O)cc1 ANEODGSBULPLDD-UHFFFAOYSA-N 0.000 claims 1
- AHVMIYPBQWQIBD-UHFFFAOYSA-N COc1ccc(Cn2c3sc4CN(Cc5ncccn5)CCc4c3c3ncnn3c2=O)c(F)c1 Chemical compound COc1ccc(Cn2c3sc4CN(Cc5ncccn5)CCc4c3c3ncnn3c2=O)c(F)c1 AHVMIYPBQWQIBD-UHFFFAOYSA-N 0.000 claims 1
- APOFBWXSMCOIBV-UHFFFAOYSA-N COc1ccc(Cn2c3scc(CNCC4CCOCC4)c3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3scc(CNCC4CCOCC4)c3c3ncnn3c2=O)cc1 APOFBWXSMCOIBV-UHFFFAOYSA-N 0.000 claims 1
- SEXIYRMHCOVIFH-UHFFFAOYSA-N COc1ccc(Cn2c3sccc3c3ncnn3c2=O)cc1 Chemical compound COc1ccc(Cn2c3sccc3c3ncnn3c2=O)cc1 SEXIYRMHCOVIFH-UHFFFAOYSA-N 0.000 claims 1
- VVZWJUPKEOQTQC-UHFFFAOYSA-N Cc1cc2c(s1)n(Cc1ccc(Cl)cc1)c(=O)n1ncnc21 Chemical compound Cc1cc2c(s1)n(Cc1ccc(Cl)cc1)c(=O)n1ncnc21 VVZWJUPKEOQTQC-UHFFFAOYSA-N 0.000 claims 1
- MFMNBVNZRPIHBX-UHFFFAOYSA-N Cc1cc2c(s1)n(Cc1cccc(Cl)c1)c(=O)n1ncnc21 Chemical compound Cc1cc2c(s1)n(Cc1cccc(Cl)c1)c(=O)n1ncnc21 MFMNBVNZRPIHBX-UHFFFAOYSA-N 0.000 claims 1
- SGQMFQBSVVLQHR-UHFFFAOYSA-N Cc1cc2c(s1)n(Cc1ccccc1Cl)c(=O)n1ncnc21 Chemical compound Cc1cc2c(s1)n(Cc1ccccc1Cl)c(=O)n1ncnc21 SGQMFQBSVVLQHR-UHFFFAOYSA-N 0.000 claims 1
- XALOIJXHGLAHIU-UHFFFAOYSA-N Cc1cc2c3ncnn3c(=O)n(Cc3ccccc3)c2s1 Chemical compound Cc1cc2c3ncnn3c(=O)n(Cc3ccccc3)c2s1 XALOIJXHGLAHIU-UHFFFAOYSA-N 0.000 claims 1
- HOZLUVKUQYVKCL-UHFFFAOYSA-N Cc1csc2n(Cc3ccc(Cl)cc3)c(=O)n3ncnc3c12 Chemical compound Cc1csc2n(Cc3ccc(Cl)cc3)c(=O)n3ncnc3c12 HOZLUVKUQYVKCL-UHFFFAOYSA-N 0.000 claims 1
- NUIMPXSRZYAKBV-UHFFFAOYSA-N Cc1csc2n(Cc3cccc(Cl)c3)c(=O)n3ncnc3c12 Chemical compound Cc1csc2n(Cc3cccc(Cl)c3)c(=O)n3ncnc3c12 NUIMPXSRZYAKBV-UHFFFAOYSA-N 0.000 claims 1
- AGKQXSKVBAGFRO-UHFFFAOYSA-N Cc1csc2n(Cc3ccccc3)c(=O)n3ncnc3c12 Chemical compound Cc1csc2n(Cc3ccccc3)c(=O)n3ncnc3c12 AGKQXSKVBAGFRO-UHFFFAOYSA-N 0.000 claims 1
- HSDCBXZVTONFKT-UHFFFAOYSA-N Cc1csc2n(Cc3ccccc3Cl)c(=O)n3ncnc3c12 Chemical compound Cc1csc2n(Cc3ccccc3Cl)c(=O)n3ncnc3c12 HSDCBXZVTONFKT-UHFFFAOYSA-N 0.000 claims 1
- PWITZHFHWDTWNC-UHFFFAOYSA-N Cc1sc2n(Cc3ccc(Cl)cc3)c(=O)n3ncnc3c2c1C Chemical compound Cc1sc2n(Cc3ccc(Cl)cc3)c(=O)n3ncnc3c2c1C PWITZHFHWDTWNC-UHFFFAOYSA-N 0.000 claims 1
- DGAOAGBVDNUYSF-UHFFFAOYSA-N ClC1=C(C=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1)F Chemical compound ClC1=C(C=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1)F DGAOAGBVDNUYSF-UHFFFAOYSA-N 0.000 claims 1
- VOXIRWKOACOMEA-UHFFFAOYSA-N ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2CC2)=NC=N3)=O)C=C1)F Chemical compound ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2CC2)=NC=N3)=O)C=C1)F VOXIRWKOACOMEA-UHFFFAOYSA-N 0.000 claims 1
- GEYAWCZYMGLHIX-UHFFFAOYSA-N ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2COCC2)=NC=N3)=O)C=C1)F Chemical compound ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2COCC2)=NC=N3)=O)C=C1)F GEYAWCZYMGLHIX-UHFFFAOYSA-N 0.000 claims 1
- UVXBVHXLVXMKLE-UHFFFAOYSA-N ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=C2)=NC=N3)=O)C=C1)F Chemical compound ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=C2)=NC=N3)=O)C=C1)F UVXBVHXLVXMKLE-UHFFFAOYSA-N 0.000 claims 1
- ZOQMFXLWQXULLC-UHFFFAOYSA-N ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=N2)=NC=N3)=O)C=C1)F Chemical compound ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=N2)=NC=N3)=O)C=C1)F ZOQMFXLWQXULLC-UHFFFAOYSA-N 0.000 claims 1
- QXDARSBTZZQMEA-UHFFFAOYSA-N ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2CCOCC2)=NC=N3)=O)C=C1)F Chemical compound ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2CCOCC2)=NC=N3)=O)C=C1)F QXDARSBTZZQMEA-UHFFFAOYSA-N 0.000 claims 1
- QVMNZSZLGXSPIS-UHFFFAOYSA-N ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC=2N(C=CN2)C)=NC=N3)=O)C=C1)F Chemical compound ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC=2N(C=CN2)C)=NC=N3)=O)C=C1)F QVMNZSZLGXSPIS-UHFFFAOYSA-N 0.000 claims 1
- WWBSJDAJGFOJCZ-UHFFFAOYSA-N ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1)F Chemical compound ClC1=CC(=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1)F WWBSJDAJGFOJCZ-UHFFFAOYSA-N 0.000 claims 1
- APEZIQPMBZZQOG-UHFFFAOYSA-N ClC1=CC=C(C(=O)N2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC(=C(C=C2)OC)OC)=O)N=CN3)C=C1 Chemical compound ClC1=CC=C(C(=O)N2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC(=C(C=C2)OC)OC)=O)N=CN3)C=C1 APEZIQPMBZZQOG-UHFFFAOYSA-N 0.000 claims 1
- LDKZURJACNZTAQ-UHFFFAOYSA-N ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CC(OC2)(C)C)=NC=N3)=O)C=C1 Chemical compound ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CC(OC2)(C)C)=NC=N3)=O)C=C1 LDKZURJACNZTAQ-UHFFFAOYSA-N 0.000 claims 1
- FYTZTJBBBNSPSE-UHFFFAOYSA-N ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2CC2)=NC=N3)=O)C=C1 Chemical compound ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C(=O)C2CC2)=NC=N3)=O)C=C1 FYTZTJBBBNSPSE-UHFFFAOYSA-N 0.000 claims 1
- YNHRARXBLWKRFA-UHFFFAOYSA-N ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C2COC2)=NC=N3)=O)C=C1 Chemical compound ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)C2COC2)=NC=N3)=O)C=C1 YNHRARXBLWKRFA-UHFFFAOYSA-N 0.000 claims 1
- JHLXJDKOZHQURO-UHFFFAOYSA-N ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC(F)(F)F)=NC=N3)=O)C=C1 Chemical compound ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC(F)(F)F)=NC=N3)=O)C=C1 JHLXJDKOZHQURO-UHFFFAOYSA-N 0.000 claims 1
- KGQCLTUHOICIST-UHFFFAOYSA-N ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2CC2)=NC=N3)=O)C=C1 Chemical compound ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2CC2)=NC=N3)=O)C=C1 KGQCLTUHOICIST-UHFFFAOYSA-N 0.000 claims 1
- GIGHBSARDFNAEG-UHFFFAOYSA-N ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1 Chemical compound ClC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1 GIGHBSARDFNAEG-UHFFFAOYSA-N 0.000 claims 1
- YSIHBQFXLASEFI-UHFFFAOYSA-N ClC1=CC=C(CN2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC(=C(C=C2)OC)OC)=O)N=CN3)C=C1 Chemical compound ClC1=CC=C(CN2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC(=C(C=C2)OC)OC)=O)N=CN3)C=C1 YSIHBQFXLASEFI-UHFFFAOYSA-N 0.000 claims 1
- UGIUOPSHJMVORA-UHFFFAOYSA-N ClC1=CC=C(CN2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC=C(C=C2)OC)=O)N=CN3)C=C1 Chemical compound ClC1=CC=C(CN2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC=C(C=C2)OC)=O)N=CN3)C=C1 UGIUOPSHJMVORA-UHFFFAOYSA-N 0.000 claims 1
- IUFGFNGPXKSEGF-UHFFFAOYSA-N ClC1=CC=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC=C2 Chemical compound ClC1=CC=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC=C2 IUFGFNGPXKSEGF-UHFFFAOYSA-N 0.000 claims 1
- GWYOCNSTQSPTIH-UHFFFAOYSA-N ClC=1C=C(C(=O)N2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC(=C(C=C2)OC)OC)=O)N=CN3)C=CC1 Chemical compound ClC=1C=C(C(=O)N2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC(=C(C=C2)OC)OC)=O)N=CN3)C=CC1 GWYOCNSTQSPTIH-UHFFFAOYSA-N 0.000 claims 1
- RSCVFEIQNCCQJV-UHFFFAOYSA-N ClC=1C=C(CN2C(N3C(C4=C2SC2=C4CCCC2)=NC=N3)=O)C=CC1 Chemical compound ClC=1C=C(CN2C(N3C(C4=C2SC2=C4CCCC2)=NC=N3)=O)C=CC1 RSCVFEIQNCCQJV-UHFFFAOYSA-N 0.000 claims 1
- FUROPITVEUTFRT-UHFFFAOYSA-N ClC=1C=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=CC1Cl Chemical compound ClC=1C=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=CC1Cl FUROPITVEUTFRT-UHFFFAOYSA-N 0.000 claims 1
- IJPNTJFSFUIZOQ-UHFFFAOYSA-N ClC=1C=C(CN2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC(=C(C=C2)OC)OC)=O)N=CN3)C=CC1 Chemical compound ClC=1C=C(CN2CCCC3=C2SC2=C3C=3N(C(N2CC2=CC(=C(C=C2)OC)OC)=O)N=CN3)C=CC1 IJPNTJFSFUIZOQ-UHFFFAOYSA-N 0.000 claims 1
- MXUFVYHDCXAYDN-UHFFFAOYSA-N Clc1ccc(Cn2c3sc(Cc4ccccc4)cc3c3ncnn3c2=O)cc1 Chemical compound Clc1ccc(Cn2c3sc(Cc4ccccc4)cc3c3ncnn3c2=O)cc1 MXUFVYHDCXAYDN-UHFFFAOYSA-N 0.000 claims 1
- LTYRCXICCQLOGR-UHFFFAOYSA-N Clc1ccc(Cn2c3sccc3c3ncnn3c2=O)cc1 Chemical compound Clc1ccc(Cn2c3sccc3c3ncnn3c2=O)cc1 LTYRCXICCQLOGR-UHFFFAOYSA-N 0.000 claims 1
- WIUKRYCFMGWGIT-UHFFFAOYSA-N Clc1cccc(Cn2c3sc(Cc4ccccc4)cc3c3ncnn3c2=O)c1 Chemical compound Clc1cccc(Cn2c3sc(Cc4ccccc4)cc3c3ncnn3c2=O)c1 WIUKRYCFMGWGIT-UHFFFAOYSA-N 0.000 claims 1
- XKRMWNSYFNDDGV-UHFFFAOYSA-N Clc1cccc(Cn2c3sccc3c3ncnn3c2=O)c1 Chemical compound Clc1cccc(Cn2c3sccc3c3ncnn3c2=O)c1 XKRMWNSYFNDDGV-UHFFFAOYSA-N 0.000 claims 1
- DSRPGHZKWOJJBM-UHFFFAOYSA-N Clc1ccccc1Cn1c2sc(Cc3ccccc3)cc2c2ncnn2c1=O Chemical compound Clc1ccccc1Cn1c2sc(Cc3ccccc3)cc2c2ncnn2c1=O DSRPGHZKWOJJBM-UHFFFAOYSA-N 0.000 claims 1
- 101001117089 Drosophila melanogaster Calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1 Proteins 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- BTHXJFKRDTYHIR-UHFFFAOYSA-N FC(C(C)N1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1)F Chemical compound FC(C(C)N1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1)F BTHXJFKRDTYHIR-UHFFFAOYSA-N 0.000 claims 1
- DJASSSXMLDJHHC-UHFFFAOYSA-N FC(C1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1)(F)F Chemical compound FC(C1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1)(F)F DJASSSXMLDJHHC-UHFFFAOYSA-N 0.000 claims 1
- UNNFFXXGLGJBET-UHFFFAOYSA-N FC(F)(F)Oc1ccc(Cn2c3sc4COCCc4c3c3ncnn3c2=O)cc1 Chemical compound FC(F)(F)Oc1ccc(Cn2c3sc4COCCc4c3c3ncnn3c2=O)cc1 UNNFFXXGLGJBET-UHFFFAOYSA-N 0.000 claims 1
- PRDXEDQLSDAYKR-UHFFFAOYSA-N FC1(C(C1)C(=O)N1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1)F Chemical compound FC1(C(C1)C(=O)N1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1)F PRDXEDQLSDAYKR-UHFFFAOYSA-N 0.000 claims 1
- LUJPUQWVOGYEQY-UHFFFAOYSA-N FC1(CN(CC2=C1C=1C=3N(C(N(C1S2)CC2=C(C=C(C=C2)OC)F)=O)N=CN3)CC3CCOCC3)F Chemical compound FC1(CN(CC2=C1C=1C=3N(C(N(C1S2)CC2=C(C=C(C=C2)OC)F)=O)N=CN3)CC3CCOCC3)F LUJPUQWVOGYEQY-UHFFFAOYSA-N 0.000 claims 1
- DDIQDQJQFLRLOU-UHFFFAOYSA-N FC1(CN(CC2=C1C=1C=3N(C(N(C1S2)CC2=CC=C(C=C2)OC)=O)N=CN3)C(=O)C3COCC3)F Chemical compound FC1(CN(CC2=C1C=1C=3N(C(N(C1S2)CC2=CC=C(C=C2)OC)=O)N=CN3)C(=O)C3COCC3)F DDIQDQJQFLRLOU-UHFFFAOYSA-N 0.000 claims 1
- SKPQBAJQRFEPNX-UHFFFAOYSA-N FC1(CN(CC2=C1C=1C=3N(C(N(C1S2)CC2=CC=C(C=C2)OC)=O)N=CN3)CC3COCCC3)F Chemical compound FC1(CN(CC2=C1C=1C=3N(C(N(C1S2)CC2=CC=C(C=C2)OC)=O)N=CN3)CC3COCCC3)F SKPQBAJQRFEPNX-UHFFFAOYSA-N 0.000 claims 1
- ZXHSPMXDQPMINS-UHFFFAOYSA-N FC1(OC2=C(O1)C=CC(=C2)CN2CC1=C(C=3C=4N(C(N(C3S1)CC1=CC=C(C=C1)OC)=O)N=CN4)CC2)F Chemical compound FC1(OC2=C(O1)C=CC(=C2)CN2CC1=C(C=3C=4N(C(N(C3S1)CC1=CC=C(C=C1)OC)=O)N=CN4)CC2)F ZXHSPMXDQPMINS-UHFFFAOYSA-N 0.000 claims 1
- JCMYCGHHIQJUNH-UHFFFAOYSA-N FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=C2)=NC=N3)=O)C=CC(=C1)OC Chemical compound FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2=NC=CC=C2)=NC=N3)=O)C=CC(=C1)OC JCMYCGHHIQJUNH-UHFFFAOYSA-N 0.000 claims 1
- RTLFKFHKZXSLRE-UHFFFAOYSA-N FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2COCC2)=NC=N3)=O)C=CC(=C1)OC Chemical compound FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2COCC2)=NC=N3)=O)C=CC(=C1)OC RTLFKFHKZXSLRE-UHFFFAOYSA-N 0.000 claims 1
- AZYKIZQBZJNIIN-UHFFFAOYSA-N FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2COCCC2)=NC=N3)=O)C=CC(=C1)OC Chemical compound FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC2COCCC2)=NC=N3)=O)C=CC(=C1)OC AZYKIZQBZJNIIN-UHFFFAOYSA-N 0.000 claims 1
- RZEWIKYYPHPGQQ-UHFFFAOYSA-N FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC=2N(C=CN2)C)=NC=N3)=O)C=CC(=C1)OC Chemical compound FC1=C(CN2C(N3C(C4=C2SC2=C4CCN(C2)CC=2N(C=CN2)C)=NC=N3)=O)C=CC(=C1)OC RZEWIKYYPHPGQQ-UHFFFAOYSA-N 0.000 claims 1
- SFYMKCXNUYKNAW-UHFFFAOYSA-N FC1=C(CN2CC3=C(C=4C=5N(C(N(C4S3)CC3=CC=C(C=C3)OC)=O)N=CN5)CC2)C=CC=C1 Chemical compound FC1=C(CN2CC3=C(C=4C=5N(C(N(C4S3)CC3=CC=C(C=C3)OC)=O)N=CN5)CC2)C=CC=C1 SFYMKCXNUYKNAW-UHFFFAOYSA-N 0.000 claims 1
- MFGOQOZWFRLKMZ-UHFFFAOYSA-N FC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1 Chemical compound FC1=CC=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C1 MFGOQOZWFRLKMZ-UHFFFAOYSA-N 0.000 claims 1
- GVQGBAXLLVVARQ-UHFFFAOYSA-N FC1=CC=C(CN2CC3=C(C=4C=5N(C(N(C4S3)CC3=CC=C(C=C3)OC)=O)N=CN5)CC2)C=C1 Chemical compound FC1=CC=C(CN2CC3=C(C=4C=5N(C(N(C4S3)CC3=CC=C(C=C3)OC)=O)N=CN5)CC2)C=C1 GVQGBAXLLVVARQ-UHFFFAOYSA-N 0.000 claims 1
- XTUYHBIVKNBHKC-UHFFFAOYSA-N FC=1C=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C(C1OC)F Chemical compound FC=1C=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=C(C1OC)F XTUYHBIVKNBHKC-UHFFFAOYSA-N 0.000 claims 1
- YTKXUNSERQVERG-UHFFFAOYSA-N FC=1C=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=CC1OC Chemical compound FC=1C=C(CN2C(N3C(C4=C2SC2=C4CCOC2)=NC=N3)=O)C=CC1OC YTKXUNSERQVERG-UHFFFAOYSA-N 0.000 claims 1
- RQFHKMJXRTUMGY-UHFFFAOYSA-N Fc1ccc(Cn2c3sc(CN4CCOCC4)cc3c3ncnn3c2=O)cc1Cl Chemical compound Fc1ccc(Cn2c3sc(CN4CCOCC4)cc3c3ncnn3c2=O)cc1Cl RQFHKMJXRTUMGY-UHFFFAOYSA-N 0.000 claims 1
- ZMBPRFJCDLDZOV-UHFFFAOYSA-N O1C(COCC1)CN1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1 Chemical compound O1C(COCC1)CN1CC2=C(C=3C=4N(C(N(C3S2)CC2=CC=C(C=C2)OC)=O)N=CN4)CC1 ZMBPRFJCDLDZOV-UHFFFAOYSA-N 0.000 claims 1
- PBOQMKNJXRTEHB-UHFFFAOYSA-N O=C1N2N=CN=C2C=2C(C)=C(C)OC=2N1CC1=CC=C(Cl)C=C1 Chemical compound O=C1N2N=CN=C2C=2C(C)=C(C)OC=2N1CC1=CC=C(Cl)C=C1 PBOQMKNJXRTEHB-UHFFFAOYSA-N 0.000 claims 1
- IRFZZATTYCKHHP-UHFFFAOYSA-N O=C1N=C2SC=CC2=C2N=CNN12 Chemical compound O=C1N=C2SC=CC2=C2N=CNN12 IRFZZATTYCKHHP-UHFFFAOYSA-N 0.000 claims 1
- QFKNLOGCGAEUGG-UHFFFAOYSA-N O=c1n(Cc2ccc(cc2)-c2ccccc2)c2sccc2c2ncnn12 Chemical compound O=c1n(Cc2ccc(cc2)-c2ccccc2)c2sccc2c2ncnn12 QFKNLOGCGAEUGG-UHFFFAOYSA-N 0.000 claims 1
- YRSMHCHSFURKGB-UHFFFAOYSA-N O=c1n(Cc2ccccc2)c2sc(Cc3ccccc3)cc2c2ncnn12 Chemical compound O=c1n(Cc2ccccc2)c2sc(Cc3ccccc3)cc2c2ncnn12 YRSMHCHSFURKGB-UHFFFAOYSA-N 0.000 claims 1
- YYEFLWJIMJJCFJ-UHFFFAOYSA-N O=c1n(Cc2ccccc2)c2sccc2c2ncnn12 Chemical compound O=c1n(Cc2ccccc2)c2sccc2c2ncnn12 YYEFLWJIMJJCFJ-UHFFFAOYSA-N 0.000 claims 1
- CXMQSCNDPBVQEJ-UHFFFAOYSA-N ac1lddoq Chemical compound ClC1=CC=CC=C1CN1C(=O)N2N=CN=C2C2=C1SC1=C2CCCC1 CXMQSCNDPBVQEJ-UHFFFAOYSA-N 0.000 claims 1
- GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 150000005829 chemical entities Chemical class 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261661091P | 2012-06-18 | 2012-06-18 | |
| PCT/US2013/046403 WO2013192225A1 (en) | 2012-06-18 | 2013-06-18 | Substituted thiophene- and furan-fused azolopyrimidine-5-(6h)-one compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015526394A JP2015526394A (ja) | 2015-09-10 |
| JP2015526394A5 true JP2015526394A5 (enExample) | 2016-07-21 |
| JP6240180B2 JP6240180B2 (ja) | 2017-11-29 |
Family
ID=49756458
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015518523A Active JP6129960B2 (ja) | 2012-06-18 | 2013-06-18 | 置換ピリジンアゾロピリミジン−５−（６ｈ）−オン化合物 |
| JP2015518522A Active JP6240180B2 (ja) | 2012-06-18 | 2013-06-18 | 置換チオフェン−およびフラン−縮合アゾロピリミジン−５−（６ｈ）−オン化合物 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015518523A Active JP6129960B2 (ja) | 2012-06-18 | 2013-06-18 | 置換ピリジンアゾロピリミジン−５−（６ｈ）−オン化合物 |
Country Status (17)
| Country | Link |
|---|---|
| US (7) | US9499562B2 (enExample) |
| EP (3) | EP3489238B8 (enExample) |
| JP (2) | JP6129960B2 (enExample) |
| KR (2) | KR102087756B1 (enExample) |
| CN (2) | CN104583213B (enExample) |
| AU (3) | AU2013277294C1 (enExample) |
| BR (2) | BR112014031730B1 (enExample) |
| CA (2) | CA2877149C (enExample) |
| DK (2) | DK2861603T3 (enExample) |
| ES (2) | ES2904267T3 (enExample) |
| IL (2) | IL236232A (enExample) |
| IN (2) | IN2015DN00334A (enExample) |
| MX (2) | MX359615B (enExample) |
| NZ (2) | NZ703949A (enExample) |
| RU (2) | RU2659779C2 (enExample) |
| SG (3) | SG11201408397SA (enExample) |
| WO (2) | WO2013192229A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7947731B2 (en) * | 2000-08-10 | 2011-05-24 | Cold Spring Harbor Laboratory | Augmented cognitive training |
| US9499562B2 (en) | 2012-06-18 | 2016-11-22 | Dart Neuroscience (Cayman) Ltd. | Substituted thiophene- and furan-fused azolopyrimidine-5-(6H)-one compounds |
| JP6396229B2 (ja) * | 2014-01-27 | 2018-09-26 | 株式会社ポーラファルマ | 使用時泡状を呈する外用医薬組成物 |
| JP6396231B2 (ja) * | 2014-01-27 | 2018-09-26 | 株式会社ポーラファルマ | 使用時泡状を呈する外用医薬組成物 |
| JP6396230B2 (ja) * | 2014-01-27 | 2018-09-26 | 株式会社ポーラファルマ | 使用時泡状を呈する外用医薬組成物 |
| GB201406486D0 (en) * | 2014-04-10 | 2014-05-28 | Redx Pharma Ltd | Antibacterial compounds |
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| WO2017046603A1 (en) * | 2015-09-18 | 2017-03-23 | Redx Pharma Plc | Antibacterial compounds and new uses thereof |
| TWI609870B (zh) * | 2016-02-12 | 2018-01-01 | 美國禮來大藥廠 | Pde1抑制劑 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| JOP20170164A1 (ar) * | 2016-08-25 | 2019-01-30 | Lilly Co Eli | مشتق ترايازولو بيرازينون مفيد كمثبط لـ pde1 بشري |
| US10633382B2 (en) | 2016-10-18 | 2020-04-28 | H. Lundbeck A/S | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as PDE1 inhibitors |
| LT3532064T (lt) | 2016-10-28 | 2020-09-25 | H. Lundbeck A/S | Kompleksiniai gydymai, apimantys imidazopirazonus, skirti psichiatrinių ir (arba) kognityvinių sutrikimų gydymui |
| RU2019108717A (ru) | 2016-10-28 | 2020-11-30 | Х. Лундбекк А/С | Комбинированные средства для лечения, предусматривающего введение имидазопиразинонов |
| EP3562828B1 (en) | 2016-12-28 | 2026-03-18 | Dart Neuroscience LLC | Substituted pyrazolopyrimidinone compounds as pde2 inhibitors |
| AU2017386417B2 (en) * | 2016-12-30 | 2022-07-14 | Frequency Therapeutics, Inc. | 1H-pyrrole-2,5-dione compounds and methods of using them to induce self-renewal of stem/progenitor supporting cells |
| US10919898B2 (en) * | 2017-02-23 | 2021-02-16 | Boehringer Ingelheim International Gmbh | Medical use of compound III |
| AR112457A1 (es) | 2017-08-02 | 2019-10-30 | Lilly Co Eli | Derivados de [1,2,4]triazolo[4,3-a]pirazin-6(5h)-ona |
| TW201920188A (zh) | 2017-08-10 | 2019-06-01 | 美商美國禮來大藥廠 | [1,2,4]三唑衍生物 |
| MX2020005447A (es) | 2017-11-27 | 2020-12-03 | Dart Neuroscience Llc | Compuestos de furanopirimidina sustituida como inhibidores de pde1. |
| IL296734B2 (en) | 2018-04-13 | 2025-06-01 | The Institute Of Cancer Res Royal Cancer Hospital | Bcl6 inhibitors |
| JP7493460B2 (ja) | 2018-05-25 | 2024-05-31 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| GB2575490A (en) * | 2018-07-12 | 2020-01-15 | Recordati Ind Chimica E Farmaceutica Spa | P2X3 receptor antagonists |
| WO2020146384A1 (en) | 2019-01-07 | 2020-07-16 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2021035157A1 (en) * | 2019-08-22 | 2021-02-25 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US12599603B2 (en) | 2019-09-03 | 2026-04-14 | Intra-Cellular Therapies, Inc. | Methods of treatment |
| GB201914860D0 (en) | 2019-10-14 | 2019-11-27 | Cancer Research Tech Ltd | Inhibitor compounds |
| CN112778311B (zh) * | 2019-11-01 | 2024-06-04 | 上海翰森生物医药科技有限公司 | 含氮并环类衍生物抑制剂、其制备方法和应用 |
| CN112979655A (zh) | 2019-12-16 | 2021-06-18 | 上海赛默罗生物科技有限公司 | 三唑并哒嗪类衍生物、其制备方法、药物组合物和用途 |
| EP4389746A3 (en) * | 2022-12-21 | 2024-07-03 | Recordati Industria Chimica E Farmaceutica SPA | P2x3 receptor antagonists |
| WO2025024543A1 (en) * | 2023-07-24 | 2025-01-30 | Bpgbio, Inc. | Tricyclic ube2k modulators and methods for their use |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3046366A1 (de) | 1980-12-09 | 1982-07-08 | Bayer Ag, 5090 Leverkusen | Tricyclische cytosinderivate zur verwendung in arzneimitteln und verfahren zu ihrer herstellung |
| DE3146599A1 (de) | 1981-11-25 | 1983-07-07 | Basf Ag, 6700 Ludwigshafen | Neue triazolochinazoline, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen |
| EP0181282A1 (de) | 1984-10-01 | 1986-05-14 | Ciba-Geigy Ag | Triazolochinazolinverbindungen |
| DE3677445D1 (de) | 1985-09-30 | 1991-03-14 | Ciba Geigy Ag | 2-substituierte-e-kondensierte(1,5-c)-pyrimidine, pharmazeutische zubereitungen und ihre verwendung. |
| JPS62135475A (ja) * | 1985-09-30 | 1987-06-18 | チバ−ガイギ− アクチエンゲゼルシヤフト | ２−置換−ｅ−融合−〔１，２，４〕トリアゾロ−〔１，５−Ｃ〕ピリミジン |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| FR2659329B1 (fr) | 1990-03-09 | 1994-06-03 | Adir | Nouveaux derives d'imidazo [1,2-c] quinazoline, leur procede de preparation et les compositions pharmaceutiques les renfermant. |
| AU2483599A (en) * | 1998-01-29 | 1999-08-16 | Sepracor, Inc. | Pharmaceutical uses of optically pure (-)-bupropion |
| ES2166270B1 (es) * | 1999-07-27 | 2003-04-01 | Almirall Prodesfarma Sa | Derivados de 8-fenil-6,9-dihidro-(1,2,4,)triazolo(3,4-i)purin-5-ona. |
| DE10012373A1 (de) * | 2000-03-14 | 2001-09-20 | Dresden Arzneimittel | Verwendung von Pyrido[3,2-e]-pyrazinonen als Inhibitoren der Phosphodiesterase 5 zur Therapie von erektiler Dysfunktion |
| US8153646B2 (en) | 2000-08-10 | 2012-04-10 | Dart Neuroscience (Cayman) Ltd. | Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation |
| US7947731B2 (en) | 2000-08-10 | 2011-05-24 | Cold Spring Harbor Laboratory | Augmented cognitive training |
| US7868015B2 (en) | 2000-08-10 | 2011-01-11 | Cold Spring Harbor Laboratory | Phosphodiesesterase 4 inhibitors for the treatment of a cognitive deficit |
| FR2897061B1 (fr) | 2006-02-03 | 2010-09-03 | Sanofi Aventis | Derives de n-heteroaryl-carboxamides tricycliques contenant un motif benzimidazole, leur preparation et leur application en therapeutique. |
| AU2007256633B2 (en) | 2006-06-06 | 2013-09-12 | Intra-Cellular Therapies, Inc. | Organic compounds |
| EP2139333A4 (en) * | 2007-03-28 | 2010-11-10 | Merck Sharp & Dohme | SUBSTITUTED PYRID- [3,2-E] - [1,2,4] -TRIAZOL- [4,3-C] -PYRIMIDINE DERIVATIVES AS CANNABINOID-1 RECEPTOR MODULATORS |
| AU2008254907A1 (en) | 2007-05-15 | 2008-11-27 | Helicon Therapeutics, Inc. | Methods of identifying genes involved in memory formation using small interfering RNA(siRNA) |
| CA2695802A1 (en) * | 2007-09-26 | 2009-04-02 | Ge Healthcare Bioscience Bioprocess Corp. | Three dimensional disposable bioreactor |
| EP2939676A1 (en) | 2007-12-06 | 2015-11-04 | Intra-Cellular Therapies, Inc. | Organic compounds |
| AU2008345225A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| PE20110922A1 (es) | 2008-12-06 | 2012-01-22 | Intra Cellular Therapies Inc | DERIVADOS DE PIRAZOLO[4,3-e]PIRIMIDIN COMO INHIBIDORES DE LA FOSFODIESTERASA 1 (PDE1) |
| BRPI0922700A2 (pt) * | 2008-12-06 | 2015-08-11 | Intracellular Therapies Inc | Compostos orgânicos |
| WO2010098839A1 (en) | 2009-02-25 | 2010-09-02 | Intra-Cellular Therapies, Inc. | Pde 1 inhibitors for ophthalmic disorders |
| EP2434895A4 (en) | 2009-05-13 | 2013-08-07 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| EP2575817A4 (en) | 2010-05-31 | 2014-01-08 | Intra Cellular Therapies Inc | ORGANIC CONNECTIONS |
| TW201206937A (en) | 2010-05-31 | 2012-02-16 | Intra Cellular Therapies Inc | Organic compounds |
| US9371327B2 (en) | 2010-05-31 | 2016-06-21 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| US9763948B2 (en) | 2010-05-31 | 2017-09-19 | Intra-Cellular Therapies, Inc. | PDE1 inhibitory compounds and methods |
| EP2717877B1 (en) | 2011-06-10 | 2017-11-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US9499562B2 (en) | 2012-06-18 | 2016-11-22 | Dart Neuroscience (Cayman) Ltd. | Substituted thiophene- and furan-fused azolopyrimidine-5-(6H)-one compounds |
-
2013
- 2013-06-18 US US14/408,927 patent/US9499562B2/en active Active
- 2013-06-18 KR KR1020157001117A patent/KR102087756B1/ko active Active
- 2013-06-18 MX MX2014015737A patent/MX359615B/es active IP Right Grant
- 2013-06-18 DK DK13807565.0T patent/DK2861603T3/en active
- 2013-06-18 ES ES18213541T patent/ES2904267T3/es active Active
- 2013-06-18 EP EP18213541.8A patent/EP3489238B8/en active Active
- 2013-06-18 CN CN201380043291.6A patent/CN104583213B/zh not_active Expired - Fee Related
- 2013-06-18 JP JP2015518523A patent/JP6129960B2/ja active Active
- 2013-06-18 IN IN334DEN2015 patent/IN2015DN00334A/en unknown
- 2013-06-18 US US13/920,974 patent/US9175010B2/en active Active
- 2013-06-18 AU AU2013277294A patent/AU2013277294C1/en not_active Ceased
- 2013-06-18 BR BR112014031730-5A patent/BR112014031730B1/pt not_active IP Right Cessation
- 2013-06-18 CA CA2877149A patent/CA2877149C/en active Active
- 2013-06-18 AU AU2013277298A patent/AU2013277298B2/en not_active Ceased
- 2013-06-18 SG SG11201408397SA patent/SG11201408397SA/en unknown
- 2013-06-18 DK DK18213541.8T patent/DK3489238T3/da active
- 2013-06-18 SG SG10201703253XA patent/SG10201703253XA/en unknown
- 2013-06-18 NZ NZ703949A patent/NZ703949A/en not_active IP Right Cessation
- 2013-06-18 ES ES13807565T patent/ES2715325T3/es active Active
- 2013-06-18 SG SG11201408395WA patent/SG11201408395WA/en unknown
- 2013-06-18 CN CN201380043254.5A patent/CN104583217B/zh not_active Expired - Fee Related
- 2013-06-18 RU RU2015100209A patent/RU2659779C2/ru active
- 2013-06-18 IN IN335DEN2015 patent/IN2015DN00335A/en unknown
- 2013-06-18 MX MX2014015740A patent/MX357320B/es active IP Right Grant
- 2013-06-18 JP JP2015518522A patent/JP6240180B2/ja active Active
- 2013-06-18 CA CA2877146A patent/CA2877146C/en active Active
- 2013-06-18 KR KR1020157001198A patent/KR102191816B1/ko active Active
- 2013-06-18 EP EP13807708.6A patent/EP2861605B1/en active Active
- 2013-06-18 WO PCT/US2013/046415 patent/WO2013192229A1/en not_active Ceased
- 2013-06-18 WO PCT/US2013/046403 patent/WO2013192225A1/en not_active Ceased
- 2013-06-18 NZ NZ703950A patent/NZ703950A/en not_active IP Right Cessation
- 2013-06-18 US US14/408,942 patent/US9284335B2/en active Active
- 2013-06-18 BR BR112014031731-3A patent/BR112014031731B1/pt active IP Right Grant
- 2013-06-18 RU RU2015100213A patent/RU2653054C2/ru active
- 2013-06-18 EP EP13807565.0A patent/EP2861603B1/en active Active
-
2014
- 2014-12-14 IL IL236232A patent/IL236232A/en active IP Right Grant
- 2014-12-14 IL IL236233A patent/IL236233A/en active IP Right Grant
-
2015
- 2015-09-14 US US14/853,856 patent/US9533996B2/en active Active
-
2016
- 2016-11-17 US US15/354,804 patent/US10092575B2/en active Active
- 2016-12-29 US US15/394,058 patent/US10105367B2/en active Active
-
2017
- 2017-12-07 AU AU2017272245A patent/AU2017272245B2/en active Active
-
2018
- 2018-10-18 US US16/164,726 patent/US10376514B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2015100209A (ru) | Замещенные соединения тиофен- и фуран-конденсированного азолопиримидин-5-(6н)-она | |
| EP4384159A1 (en) | Heterocyclic compounds and methods of use | |
| EP4705293A1 (en) | Spiro-heterocyclic inhibitors of kras g12c mutant proteins and uses thereof | |
| CN117651700A (zh) | 2-氨基苯并噻唑化合物及使用方法 | |
| JP2015526395A5 (enExample) | ||
| AU2023221732A1 (en) | Quinazoline compounds and use thereof as inhibtors of mutant kras proteins | |
| EP4329757A1 (en) | Heterocyclic compounds and methods of use | |
| US20250163064A1 (en) | Quinazoline compounds and uses thereof as inhibitors of mutant kras proteins | |
| WO2024076670A2 (en) | Tethered heterocyclic inhibitors of kras g12c mutant proteins and uses thereof | |
| IL275344B2 (en) | 4-azaindole compounds | |
| RU2019115115A (ru) | Производные пиперидина в качестве ингибиторов убиквитин-специфической протеазы 7 | |
| JP2011516558A5 (enExample) | ||
| JP2017505327A5 (enExample) | ||
| JP2019535664A5 (enExample) | ||
| RU2016135637A (ru) | 6-гетероарилокси- и 6-арилоксихинолин-2-карбоксамиды и их применение | |
| JP2005519086A5 (enExample) | ||
| CA2474823A1 (en) | Heteroaryl substituted 2-pyridinyl and 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a] pyrimidin-4-one derivatives | |
| WO2025217247A1 (en) | Tethered spiro-heterocyclic inhibitors of kras g12c mutant proteins and uses thereof | |
| WO2025230862A1 (en) | Macrocyclic amino compounds as modulators of kras and uses therof | |
| WO2025230878A1 (en) | Macrocyclic compounds as modulators of kras and uses thereof | |
| CN117835976A (zh) | 杂环化合物及使用方法 | |
| RU2019116137A (ru) | Пиридо[3,4-d]пиримидиновое производное и его фармацевтически приемлемая соль |