JP2014511898A5 - - Google Patents
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- Publication number
- JP2014511898A5 JP2014511898A5 JP2014505720A JP2014505720A JP2014511898A5 JP 2014511898 A5 JP2014511898 A5 JP 2014511898A5 JP 2014505720 A JP2014505720 A JP 2014505720A JP 2014505720 A JP2014505720 A JP 2014505720A JP 2014511898 A5 JP2014511898 A5 JP 2014511898A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- pyrido
- methylamino
- propionamide
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000000623 heterocyclic group Chemical group 0.000 claims 18
- 125000004452 carbocyclyl group Chemical group 0.000 claims 11
- 125000005843 halogen group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 125000006239 protecting group Chemical group 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 150000001204 N-oxides Chemical class 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 230000008878 coupling Effects 0.000 claims 4
- 238000010168 coupling process Methods 0.000 claims 4
- 238000005859 coupling reaction Methods 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 238000010511 deprotection reaction Methods 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- -1 3-Benzyl-2-oxo-1-phenyl-1,2,3,4-tetrahydro-pyrido [3,2-d] pyrimidin-6-yl Chemical group 0.000 claims 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229910052720 vanadium Inorganic materials 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 108091007065 BIRCs Proteins 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 108700031544 X-Linked Inhibitor of Apoptosis Proteins 0.000 claims 2
- 102000050257 X-Linked Inhibitor of Apoptosis Human genes 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 229910052802 copper Inorganic materials 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 230000007170 pathology Effects 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 2
- PDTUOUCUVIKQME-INIZCTEOSA-N (2s)-2-(methylamino)-n-(2-oxo-1,3-diphenyl-4h-pyrido[3,2-d]pyrimidin-6-yl)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=CC=CC=2)C(=O)N1C1=CC=CC=C1 PDTUOUCUVIKQME-INIZCTEOSA-N 0.000 claims 1
- OXRSMRVXHWVPGN-NSHDSACASA-N (2s)-2-(methylamino)-n-(2-oxo-1-phenyl-3,4-dihydropyrido[3,2-d]pyrimidin-6-yl)propanamide Chemical compound O=C1NCC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=CC=C1 OXRSMRVXHWVPGN-NSHDSACASA-N 0.000 claims 1
- QKAPYJRSHYQNJL-LURJTMIESA-N (2s)-2-(methylamino)-n-(2-oxo-3,4-dihydro-1h-pyrido[2,3-b]pyrazin-6-yl)propanamide Chemical compound N1C(=O)CNC2=NC(NC(=O)[C@H](C)NC)=CC=C21 QKAPYJRSHYQNJL-LURJTMIESA-N 0.000 claims 1
- GMOAYSCTDXPNDF-RGMNGODLSA-N (2s)-2-(methylamino)-n-(2-oxo-3,4-dihydro-1h-pyrido[3,2-d]pyrimidin-6-yl)propanamide;hydrochloride Chemical compound Cl.N1C(=O)NCC2=NC(NC(=O)[C@H](C)NC)=CC=C21 GMOAYSCTDXPNDF-RGMNGODLSA-N 0.000 claims 1
- PNMAQVMJAJLUJR-VIFPVBQESA-N (2s)-2-(methylamino)-n-(2-oxo-3-propan-2-yl-1,4-dihydropyrido[3,2-d]pyrimidin-6-yl)propanamide Chemical compound N1C(=O)N(C(C)C)CC2=NC(NC(=O)[C@H](C)NC)=CC=C21 PNMAQVMJAJLUJR-VIFPVBQESA-N 0.000 claims 1
- GTKDUGMRABLHEB-GZWBLTSWSA-N (2s)-2-(methylamino)-n-[3-methyl-3-(3-methylbutyl)-2-oxo-1-phenylpyrido[2,3-b][1,4]oxazin-6-yl]propanamide Chemical compound O=C1C(C)(CCC(C)C)OC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=CC=C1 GTKDUGMRABLHEB-GZWBLTSWSA-N 0.000 claims 1
- KCQTUJRMPMFXJA-LBPRGKRZSA-N (2s)-2-amino-n-[1-(4-chlorophenyl)-3,3-diethyl-2-oxopyrido[2,3-b][1,4]oxazin-6-yl]propanamide Chemical compound O=C1C(CC)(CC)OC2=NC(NC(=O)[C@H](C)N)=CC=C2N1C1=CC=C(Cl)C=C1 KCQTUJRMPMFXJA-LBPRGKRZSA-N 0.000 claims 1
- CXCFXGRTMOQYJQ-QMMMGPOBSA-N (2s)-n-(1,3-dimethyl-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl)-2-(methylamino)propanamide Chemical compound CN1C(=O)N(C)CC2=NC(NC(=O)[C@H](C)NC)=CC=C21 CXCFXGRTMOQYJQ-QMMMGPOBSA-N 0.000 claims 1
- MHIUYTGBNFDDCR-ZETCQYMHSA-N (2s)-n-(1,3-dimethyl-2-oxoimidazo[4,5-b]pyridin-5-yl)-2-(methylamino)propanamide Chemical compound CN[C@@H](C)C(=O)NC1=CC=C2N(C)C(=O)N(C)C2=N1 MHIUYTGBNFDDCR-ZETCQYMHSA-N 0.000 claims 1
- YHPQTSVDHYTNDA-OWJWWREXSA-N (2s)-n-[(3s)-1-(4-chlorophenyl)-3-methyl-2-oxo-3-phenylpyrido[2,3-b][1,4]oxazin-6-yl]-2-(methylamino)propanamide Chemical compound C1([C@@]2(C)C(=O)N(C3=CC=C(N=C3O2)NC(=O)[C@H](C)NC)C=2C=CC(Cl)=CC=2)=CC=CC=C1 YHPQTSVDHYTNDA-OWJWWREXSA-N 0.000 claims 1
- MRMPGFDIHFITIZ-LBPRGKRZSA-N (2s)-n-[1,3-bis(3,5-dichlorophenyl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=C(Cl)C=C(Cl)C=2)C(=O)N1C1=CC(Cl)=CC(Cl)=C1 MRMPGFDIHFITIZ-LBPRGKRZSA-N 0.000 claims 1
- IZRZKEARCDIREJ-AWEZNQCLSA-N (2s)-n-[1,3-bis(3-chlorophenyl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=C(Cl)C=CC=2)C(=O)N1C1=CC=CC(Cl)=C1 IZRZKEARCDIREJ-AWEZNQCLSA-N 0.000 claims 1
- NNUAFICKSHAQML-AWEZNQCLSA-N (2s)-n-[1,3-bis(4-chlorophenyl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=CC(Cl)=CC=2)C(=O)N1C1=CC=C(Cl)C=C1 NNUAFICKSHAQML-AWEZNQCLSA-N 0.000 claims 1
- OYSZKSYOPMKKLG-ZDUSSCGKSA-N (2s)-n-[1-(3-chlorophenyl)-2-oxo-3-propan-2-yl-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1N(C(C)C)CC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=CC(Cl)=C1 OYSZKSYOPMKKLG-ZDUSSCGKSA-N 0.000 claims 1
- CAVXVPDORXHSDG-NSHDSACASA-N (2s)-n-[1-(3-chlorophenyl)-3,3-dimethyl-2-oxopyrido[2,3-b][1,4]oxazin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1C(C)(C)OC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=CC(Cl)=C1 CAVXVPDORXHSDG-NSHDSACASA-N 0.000 claims 1
- OIQCZTRNJCTGSE-MLCCFXAWSA-N (2s)-n-[1-(3-chlorophenyl)-3-(1-cyclobutylethyl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=C(Cl)C=CC=2)C(=O)N1C(C)C1CCC1 OIQCZTRNJCTGSE-MLCCFXAWSA-N 0.000 claims 1
- WWPGRSUZWJAQMC-MLCCFXAWSA-N (2s)-n-[1-(3-chlorophenyl)-3-(3-methylbutan-2-yl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1N(C(C)C(C)C)CC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=CC(Cl)=C1 WWPGRSUZWJAQMC-MLCCFXAWSA-N 0.000 claims 1
- HTFGTGMFHNJNHU-INIZCTEOSA-N (2s)-n-[1-(3-chlorophenyl)-3-(4,4-dimethylcyclohexyl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=C(Cl)C=CC=2)C(=O)N1C1CCC(C)(C)CC1 HTFGTGMFHNJNHU-INIZCTEOSA-N 0.000 claims 1
- LRGDTQNREMKEQE-LYKKTTPLSA-N (2s)-n-[1-(3-chlorophenyl)-3-(4,4-dimethylpentan-2-yl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1N(C(C)CC(C)(C)C)CC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=CC(Cl)=C1 LRGDTQNREMKEQE-LYKKTTPLSA-N 0.000 claims 1
- MVSGCFSZUJVYHJ-HNNXBMFYSA-N (2s)-n-[1-(3-chlorophenyl)-3-(cyclopentylmethyl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=C(Cl)C=CC=2)C(=O)N1CC1CCCC1 MVSGCFSZUJVYHJ-HNNXBMFYSA-N 0.000 claims 1
- FNZAQTFFAODKPS-JRQMZCAUSA-N (2s)-n-[1-(3-chlorophenyl)-3-cyclopentyl-3-methyl-2-oxopyrido[2,3-b][1,4]oxazin-6-yl]-2-(methylamino)propanamide Chemical compound O1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=C(Cl)C=CC=2)C(=O)C1(C)C1CCCC1 FNZAQTFFAODKPS-JRQMZCAUSA-N 0.000 claims 1
- PSDACRUMHAHVGP-XLEXHMCLSA-N (2s)-n-[1-(3-chlorophenyl)-3-methyl-3-(2-methylpropyl)-2-oxopyrido[2,3-b][1,4]oxazin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1C(C)(CC(C)C)OC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=CC(Cl)=C1 PSDACRUMHAHVGP-XLEXHMCLSA-N 0.000 claims 1
- METJSNYQFRXVOZ-JTQLQIEISA-N (2s)-n-[1-(4-chlorophenyl)-2-oxo-3,4-dihydropyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1NCC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=C(Cl)C=C1 METJSNYQFRXVOZ-JTQLQIEISA-N 0.000 claims 1
- UDJRBEWYQBAVQL-ZDUSSCGKSA-N (2s)-n-[1-(4-chlorophenyl)-2-oxo-3-(1,3-thiazol-4-ylmethyl)-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=CC(Cl)=CC=2)C(=O)N1CC1=CSC=N1 UDJRBEWYQBAVQL-ZDUSSCGKSA-N 0.000 claims 1
- JZEUNILQFMESSA-KRWDZBQOSA-N (2s)-n-[1-(4-chlorophenyl)-2-oxo-3-(2-phenylethyl)-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=CC(Cl)=CC=2)C(=O)N1CCC1=CC=CC=C1 JZEUNILQFMESSA-KRWDZBQOSA-N 0.000 claims 1
- LWMUZICIPCPIGH-ZDUSSCGKSA-N (2s)-n-[1-(4-chlorophenyl)-2-oxo-3-propan-2-yl-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1N(C(C)C)CC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=C(Cl)C=C1 LWMUZICIPCPIGH-ZDUSSCGKSA-N 0.000 claims 1
- QBEYSGGKZNSRMT-JTQLQIEISA-N (2s)-n-[1-(4-chlorophenyl)-2-oxopyrido[2,3-b][1,4]oxazin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1COC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=C(Cl)C=C1 QBEYSGGKZNSRMT-JTQLQIEISA-N 0.000 claims 1
- IFHUXCXCPXUUHR-ZDUSSCGKSA-N (2s)-n-[1-(4-chlorophenyl)-3,3-diethyl-2-oxopyrido[2,3-b][1,4]oxazin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1C(CC)(CC)OC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=C(Cl)C=C1 IFHUXCXCPXUUHR-ZDUSSCGKSA-N 0.000 claims 1
- QZYBEEMBWZGJBJ-NSHDSACASA-N (2s)-n-[1-(4-chlorophenyl)-3,3-dimethyl-2-oxopyrido[2,3-b][1,4]oxazin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1C(C)(C)OC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=C(Cl)C=C1 QZYBEEMBWZGJBJ-NSHDSACASA-N 0.000 claims 1
- IWQCYLBUROOEFW-LYKKTTPLSA-N (2s)-n-[1-(4-chlorophenyl)-3-(4-methylpentan-2-yl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1N(C(C)CC(C)C)CC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=C(Cl)C=C1 IWQCYLBUROOEFW-LYKKTTPLSA-N 0.000 claims 1
- SSHFXYKIOYSBSX-HNNXBMFYSA-N (2s)-n-[1-(4-chlorophenyl)-3-cyclohexyl-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=CC(Cl)=CC=2)C(=O)N1C1CCCCC1 SSHFXYKIOYSBSX-HNNXBMFYSA-N 0.000 claims 1
- YDGFAYJPDUNMEV-AWEZNQCLSA-N (2s)-n-[1-(4-chlorophenyl)-3-cyclopentyl-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=CC(Cl)=CC=2)C(=O)N1C1CCCC1 YDGFAYJPDUNMEV-AWEZNQCLSA-N 0.000 claims 1
- SOXBWWXKFGIPHB-NSHDSACASA-N (2s)-n-[1-(4-chlorophenyl)-3-methyl-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound O=C1N(C)CC2=NC(NC(=O)[C@H](C)NC)=CC=C2N1C1=CC=C(Cl)C=C1 SOXBWWXKFGIPHB-NSHDSACASA-N 0.000 claims 1
- JZAPJOLDXTWWMM-HNNXBMFYSA-N (2s)-n-[3-(1-acetylpiperidin-4-yl)-1-(3-chlorophenyl)-2-oxo-4h-pyrido[3,2-d]pyrimidin-6-yl]-2-(methylamino)propanamide Chemical compound C1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=C(Cl)C=CC=2)C(=O)N1C1CCN(C(C)=O)CC1 JZAPJOLDXTWWMM-HNNXBMFYSA-N 0.000 claims 1
- CNEXWMLEGPLCRR-YPHZTSLFSA-N (2s)-n-[3-benzyl-1-(3-chlorophenyl)-3-methyl-2-oxopyrido[2,3-b][1,4]oxazin-6-yl]-2-(methylamino)propanamide Chemical compound O1C2=NC(NC(=O)[C@H](C)NC)=CC=C2N(C=2C=C(Cl)C=CC=2)C(=O)C1(C)CC1=CC=CC=C1 CNEXWMLEGPLCRR-YPHZTSLFSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- RDHRHRUSZUJHRI-UHFFFAOYSA-N n-(3-benzyl-2-oxo-1h-imidazo[4,5-b]pyridin-5-yl)-2-(methylamino)propanamide;hydrochloride Chemical compound Cl.C12=NC(NC(=O)C(C)NC)=CC=C2NC(=O)N1CC1=CC=CC=C1 RDHRHRUSZUJHRI-UHFFFAOYSA-N 0.000 claims 1
- LQPQQRJLZWOHGF-UHFFFAOYSA-N n-[3-[(4-chlorophenyl)methyl]-2-oxo-1h-imidazo[4,5-b]pyridin-5-yl]-2-(methylamino)propanamide Chemical compound C12=NC(NC(=O)C(C)NC)=CC=C2NC(=O)N1CC1=CC=C(Cl)C=C1 LQPQQRJLZWOHGF-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161477718P | 2011-04-21 | 2011-04-21 | |
| US61/477,718 | 2011-04-21 | ||
| GBGB1106814.5A GB201106814D0 (en) | 2011-04-21 | 2011-04-21 | New compounds |
| GB1106814.5 | 2011-04-21 | ||
| PCT/GB2012/050866 WO2012143725A1 (en) | 2011-04-21 | 2012-04-20 | Bicyclic heterocycle compounds and their uses in therapy |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014511898A JP2014511898A (ja) | 2014-05-19 |
| JP2014511898A5 true JP2014511898A5 (enExample) | 2015-06-11 |
| JP6100237B2 JP6100237B2 (ja) | 2017-03-22 |
Family
ID=44147395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014505720A Active JP6100237B2 (ja) | 2011-04-21 | 2012-04-20 | 二環式複素環化合物および治療法におけるその使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9155743B2 (enExample) |
| EP (1) | EP2699574B1 (enExample) |
| JP (1) | JP6100237B2 (enExample) |
| GB (1) | GB201106814D0 (enExample) |
| WO (1) | WO2012143725A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201106817D0 (en) | 2011-04-21 | 2011-06-01 | Astex Therapeutics Ltd | New compound |
| GB201106814D0 (en) | 2011-04-21 | 2011-06-01 | Astex Therapeutics Ltd | New compounds |
| GB201218864D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218850D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| US9980973B2 (en) | 2012-10-19 | 2018-05-29 | Astex Therapeutics Limited | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218862D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| AU2014369446C1 (en) | 2013-12-20 | 2020-03-12 | Astex Therapeutics Limited | Bicyclic heterocycle compounds and their uses in therapy |
| JP6576942B6 (ja) * | 2014-03-03 | 2019-11-27 | マドリガル ファーマシューティカルズ インコーポレイテッド | 標的治療薬 |
| US20200247794A1 (en) * | 2015-10-22 | 2020-08-06 | Mangosuthu University Of Technology | Pharmacophores, compounds and methods having application in the treatment of cancer through inhibition of cyp17a1 and cyp19a1 |
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| CA3087886A1 (en) | 2018-01-19 | 2019-07-25 | Idorsia Pharmaceuticals Ltd | C5a receptor modulators |
| CN108610343A (zh) * | 2018-06-12 | 2018-10-02 | 杨文思 | 一种用于治疗癌症的表皮生长因子受体抑制剂及其合成方法 |
| CN114380845B (zh) * | 2020-10-19 | 2025-06-20 | 四川科伦博泰生物医药股份有限公司 | 一种并杂环类化合物，包含其的药物组合物，其制备方法及其用途 |
| WO2025231323A1 (en) * | 2024-05-03 | 2025-11-06 | Xenon Pharmaceuticals Inc. | Bicyclic heteroaryl compounds and uses thereof |
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| US5192659A (en) | 1989-08-25 | 1993-03-09 | Genetype Ag | Intron sequence analysis method for detection of adjacent and remote locus alleles as haplotypes |
| US5525606A (en) * | 1994-08-01 | 1996-06-11 | The United States Of America As Represented By The Department Of Health And Human Services | Substituted 06-benzylguanines and 6(4)-benzyloxypyrimidines |
| WO1998004689A1 (en) | 1995-07-31 | 1998-02-05 | Urocor, Inc. | Biomarkers and targets for diagnosis, prognosis and management of prostate disease |
| US6218529B1 (en) | 1995-07-31 | 2001-04-17 | Urocor, Inc. | Biomarkers and targets for diagnosis, prognosis and management of prostate, breast and bladder cancer |
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| WO2004006906A2 (en) | 2002-07-15 | 2004-01-22 | Combinatorx, Incorporated | Methods for the treatment of neoplasms |
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| JP2004217582A (ja) * | 2003-01-16 | 2004-08-05 | Abbott Japan Co Ltd | ９ｈ−プリン誘導体 |
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| KR101250297B1 (ko) | 2008-03-31 | 2013-04-03 | 주식회사 씨앤드씨신약연구소 | 헤테로사이클 유도체 |
| GB201106814D0 (en) | 2011-04-21 | 2011-06-01 | Astex Therapeutics Ltd | New compounds |
| GB201106817D0 (en) | 2011-04-21 | 2011-06-01 | Astex Therapeutics Ltd | New compound |
| GB201218862D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218864D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| GB201218850D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
| AU2014369446C1 (en) | 2013-12-20 | 2020-03-12 | Astex Therapeutics Limited | Bicyclic heterocycle compounds and their uses in therapy |
-
2011
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2012
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- 2012-04-20 US US14/112,581 patent/US9155743B2/en active Active
- 2012-04-20 JP JP2014505720A patent/JP6100237B2/ja active Active
- 2012-04-20 EP EP12717459.7A patent/EP2699574B1/en active Active
-
2015
- 2015-08-26 US US14/836,326 patent/US9458158B2/en active Active
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