JP2013515729A5 - - Google Patents
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- JP2013515729A5 JP2013515729A5 JP2012546092A JP2012546092A JP2013515729A5 JP 2013515729 A5 JP2013515729 A5 JP 2013515729A5 JP 2012546092 A JP2012546092 A JP 2012546092A JP 2012546092 A JP2012546092 A JP 2012546092A JP 2013515729 A5 JP2013515729 A5 JP 2013515729A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- fluoro
- pyridin
- aminocyclohexylamino
- ylamino
- 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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- -1 pyrazol-4-yl Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 22
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims description 4
- BSLMYSMDBCERIF-LLVKDONJSA-N (2r)-2-[[7-fluoro-4-(5-methylfuran-2-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC=C(C)O1 BSLMYSMDBCERIF-LLVKDONJSA-N 0.000 claims description 3
- FGNXLVIOOATBPG-CYBMUJFWSA-N (2r)-2-[(7-fluoro-3-oxo-4-pyrazolo[1,5-a]pyridin-3-yl-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl)amino]-4-methylpentanamide Chemical compound C1=NN2C=CC=CC2=C1C1=C(C(=O)NC2)C2=C(F)C(N[C@H](CC(C)C)C(N)=O)=N1 FGNXLVIOOATBPG-CYBMUJFWSA-N 0.000 claims description 2
- JJLZPPPPMCXNMR-SNVBAGLBSA-N (2r)-2-[(7-fluoro-3-oxo-4-thiophen-2-yl-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl)amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC=CS1 JJLZPPPPMCXNMR-SNVBAGLBSA-N 0.000 claims description 2
- CIGKEEPNOLLPRK-LLVKDONJSA-N (2r)-2-[(7-fluoro-3-oxo-4-thiophen-3-yl-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl)amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C=1C=CSC=1 CIGKEEPNOLLPRK-LLVKDONJSA-N 0.000 claims description 2
- XXXHWWOKBAILHE-CQSZACIVSA-N (2r)-2-[[4-(1-benzofuran-3-yl)-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C1=CC=C2C(C=3N=C(C(=C4CNC(=O)C4=3)F)N[C@H](CC(C)C)C(N)=O)=COC2=C1 XXXHWWOKBAILHE-CQSZACIVSA-N 0.000 claims description 2
- KDUTVDRIWILGKD-CYBMUJFWSA-N (2r)-2-[[4-(1-cyclopropylpyrazol-4-yl)-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C(=C1)C=NN1C1CC1 KDUTVDRIWILGKD-CYBMUJFWSA-N 0.000 claims description 2
- HZWOOJCFQCXZBU-LLVKDONJSA-N (2r)-2-[[4-(4-cyanothiophen-2-yl)-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC(C#N)=CS1 HZWOOJCFQCXZBU-LLVKDONJSA-N 0.000 claims description 2
- JTHONIAHQFULQN-LLVKDONJSA-N (2r)-2-[[4-(5-cyanothiophen-2-yl)-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC=C(C#N)S1 JTHONIAHQFULQN-LLVKDONJSA-N 0.000 claims description 2
- XRGNIAJRYCAFFV-SNVBAGLBSA-N (2r)-2-[[4-[1-(difluoromethyl)pyrazol-4-yl]-7-fluoro-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C=1C=NN(C(F)F)C=1 XRGNIAJRYCAFFV-SNVBAGLBSA-N 0.000 claims description 2
- MBLSIKKPQOPSNQ-SECBINFHSA-N (2r)-2-[[7-fluoro-3-oxo-4-(1,3-thiazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CN=CS1 MBLSIKKPQOPSNQ-SECBINFHSA-N 0.000 claims description 2
- BAWQWVQBXIDYII-LLVKDONJSA-N (2r)-2-[[7-fluoro-4-(1-methylpyrazol-4-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C=1C=NN(C)C=1 BAWQWVQBXIDYII-LLVKDONJSA-N 0.000 claims description 2
- ORFPWEPWRPUBLL-GFCCVEGCSA-N (2r)-2-[[7-fluoro-4-(1-methylpyrazol-4-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-n,4-dimethylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(=O)NC)=NC=1C=1C=NN(C)C=1 ORFPWEPWRPUBLL-GFCCVEGCSA-N 0.000 claims description 2
- KUOCWDDVPWWSKP-SNVBAGLBSA-N (2r)-2-[[7-fluoro-4-(2-methyl-1,3-thiazol-5-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CN=C(C)S1 KUOCWDDVPWWSKP-SNVBAGLBSA-N 0.000 claims description 2
- UZPROEIMLUTQLE-LLVKDONJSA-N (2r)-2-[[7-fluoro-4-(4-methylthiophen-2-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC(C)=CS1 UZPROEIMLUTQLE-LLVKDONJSA-N 0.000 claims description 2
- NHPYANOEODOMDL-LLVKDONJSA-N (2r)-2-[[7-fluoro-4-(5-methylthiophen-2-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC=C(C)S1 NHPYANOEODOMDL-LLVKDONJSA-N 0.000 claims description 2
- GEKOIFFWMZQBDJ-SNVBAGLBSA-N (2r)-2-[[7-fluoro-4-(furan-2-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C1=CC=CO1 GEKOIFFWMZQBDJ-SNVBAGLBSA-N 0.000 claims description 2
- NTOQJLGNEKUUHL-LLVKDONJSA-N (2r)-2-[[7-fluoro-4-(furan-3-yl)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]-4-methylpentanamide Chemical compound C=12C(=O)NCC2=C(F)C(N[C@H](CC(C)C)C(N)=O)=NC=1C=1C=COC=1 NTOQJLGNEKUUHL-LLVKDONJSA-N 0.000 claims description 2
- IZLQWNFMZKOICR-OAHLLOKOSA-N (2r)-4-methyl-2-[[4-(3-methylsulfonylanilino)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridin-6-yl]amino]pentanamide Chemical compound N=1C(N[C@H](CC(C)C)C(N)=O)=CC=2CNC(=O)C=2C=1NC1=CC=CC(S(C)(=O)=O)=C1 IZLQWNFMZKOICR-OAHLLOKOSA-N 0.000 claims description 2
- UXHMPPWAKKPFSX-UHFFFAOYSA-N 6-[(2-amino-3,3,3-trifluoropropyl)amino]-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C=C(NCC(N)C(F)(F)F)N=2)=C1 UXHMPPWAKKPFSX-UHFFFAOYSA-N 0.000 claims description 2
- ZSWNYKLXHIEKMU-VIFPVBQESA-N 6-[(3s)-3-aminopyrrolidin-1-yl]-7-fluoro-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N2C[C@@H](N)CC2)=C(F)C2=C1C(=O)NC2 ZSWNYKLXHIEKMU-VIFPVBQESA-N 0.000 claims description 2
- PNRLUYPLNOPXDL-MLGOLLRUSA-N 6-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-4-(1-cyclopropylpyrazol-4-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NC(C2=CN(N=C2)C2CC2)=C(C(=O)NC2)C2=C1F PNRLUYPLNOPXDL-MLGOLLRUSA-N 0.000 claims description 2
- FCVUZQDOZYEBBN-RHSMWYFYSA-N 6-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C=C(N[C@H]3[C@H](C(F)(F)CCC3)N)N=2)=C1 FCVUZQDOZYEBBN-RHSMWYFYSA-N 0.000 claims description 2
- HYXZKQNQMCBUBO-NOZJJQNGSA-N 6-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-4-[1-(difluoromethyl)pyrazol-4-yl]-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1CCC(F)(F)[C@H](N)[C@@H]1NC1=NC(C2=CN(N=C2)C(F)F)=C(C(=O)NC2)C2=C1F HYXZKQNQMCBUBO-NOZJJQNGSA-N 0.000 claims description 2
- XOTZDLZZONOQJK-QMTHXVAHSA-N 6-[[(1r,2r)-2-amino-3,3-difluorocyclohexyl]amino]-7-fluoro-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](C(F)(F)CCC2)N)=C(F)C2=C1C(=O)NC2 XOTZDLZZONOQJK-QMTHXVAHSA-N 0.000 claims description 2
- IBRCKLBEVCEQHD-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-benzofuran-3-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=2C3=CC=CC=C3OC=2)=C(C(=O)NC2)C2=C1F IBRCKLBEVCEQHD-LSDHHAIUSA-N 0.000 claims description 2
- NLHMXERGXZJVSA-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-benzothiophen-3-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=2C3=CC=CC=C3SC=2)=C(C(=O)NC2)C2=C1F NLHMXERGXZJVSA-LSDHHAIUSA-N 0.000 claims description 2
- RBAFUBZTBXELTG-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-cyclopropylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC(N=C1C2=CN(N=C2)C2CC2)=CC2=C1C(=O)NC2 RBAFUBZTBXELTG-LSDHHAIUSA-N 0.000 claims description 2
- FFDWUYASOWCJJD-UONOGXRCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-ethylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(CC)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=CC2=C1C(=O)NC2 FFDWUYASOWCJJD-UONOGXRCSA-N 0.000 claims description 2
- BIRMRVDNUGHXQF-QWHCGFSZSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=CC2=C1C(=O)NC2 BIRMRVDNUGHXQF-QWHCGFSZSA-N 0.000 claims description 2
- LOFXHRXBASKCPJ-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(1h-indazol-6-ylamino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC(N=C1NC=2C=C3NN=CC3=CC=2)=CC2=C1C(=O)NC2 LOFXHRXBASKCPJ-LSDHHAIUSA-N 0.000 claims description 2
- BCQZEYKBUNMINW-DTWKUNHWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(2-amino-1,3-thiazol-5-yl)-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=2SC(N)=NC=2)=C(C(=O)NC2)C2=C1F BCQZEYKBUNMINW-DTWKUNHWSA-N 0.000 claims description 2
- UITJPHZNGQVUHM-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 UITJPHZNGQVUHM-JKSUJKDBSA-N 0.000 claims description 2
- UOBUBZWFFCOCAE-DLBZAZTESA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-3-oxo-1,2-dihydropyrrolo[3,4-c]pyridine-7-carbonitrile Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(C#N)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 UOBUBZWFFCOCAE-DLBZAZTESA-N 0.000 claims description 2
- ZHCYNQAPDHKDTK-ZWKOTPCHSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-7-(2-methylpyrazol-3-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(=C(N[C@H]3[C@H](CCCC3)N)N=2)C=2N(N=CC=2)C)=C1 ZHCYNQAPDHKDTK-ZWKOTPCHSA-N 0.000 claims description 2
- JCKXIUBFRBOHRV-DLBZAZTESA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylanilino)-7-prop-2-enoyl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(C(=O)C=C)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 JCKXIUBFRBOHRV-DLBZAZTESA-N 0.000 claims description 2
- JHMLNISRSWFRDP-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(3-methylsulfonylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CS(=O)(=O)C1=CC=CC(NC=2C=3C(=O)NCC=3C=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 JHMLNISRSWFRDP-JKSUJKDBSA-N 0.000 claims description 2
- VHBREDNCCOLHGT-JKSUJKDBSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-(4-fluoro-3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=C(F)C(C)=CC(NC=2C=3C(=O)NCC=3C=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 VHBREDNCCOLHGT-JKSUJKDBSA-N 0.000 claims description 2
- WELNIAICBOVSLC-WDEREUQCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-4-[1-(difluoromethyl)pyrazol-4-yl]-7-fluoro-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=CN(N=C2)C(F)F)=C(C(=O)NC2)C2=C1F WELNIAICBOVSLC-WDEREUQCSA-N 0.000 claims description 2
- QGIZHMIRSUGPQA-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-chloro-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(Cl)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 QGIZHMIRSUGPQA-LSDHHAIUSA-N 0.000 claims description 2
- XLLZLRGOFITEPW-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-1,1-dimethyl-4-(1-methylpyrazol-4-yl)-2h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NN(C)C=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2(C)C XLLZLRGOFITEPW-NWDGAFQWSA-N 0.000 claims description 2
- DDFCHGYRRJNLDH-CLGJWYQZSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-1-methyl-4-(1-methylpyrazol-4-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1NC(=O)C(C(=N2)C3=CN(C)N=C3)=C1C(F)=C2N[C@@H]1CCCC[C@@H]1N DDFCHGYRRJNLDH-CLGJWYQZSA-N 0.000 claims description 2
- XYDQHRTVTJCMOX-WDEREUQCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(2-methyl-1,3-thiazol-5-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound S1C(C)=NC=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2 XYDQHRTVTJCMOX-WDEREUQCSA-N 0.000 claims description 2
- QSLDDROANYSPRV-LSDHHAIUSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(3-methylanilino)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CC=CC(NC=2C=3C(=O)NCC=3C(F)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 QSLDDROANYSPRV-LSDHHAIUSA-N 0.000 claims description 2
- HPFJFZGOUINWHT-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(4-methylthiophen-2-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound CC1=CSC(C=2C=3C(=O)NCC=3C(F)=C(N[C@H]3[C@H](CCCC3)N)N=2)=C1 HPFJFZGOUINWHT-NWDGAFQWSA-N 0.000 claims description 2
- JVWJCIFIORGGQG-NWDGAFQWSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-(5-methylthiophen-2-yl)-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound S1C(C)=CC=C1C1=NC(N[C@H]2[C@H](CCCC2)N)=C(F)C2=C1C(=O)NC2 JVWJCIFIORGGQG-NWDGAFQWSA-N 0.000 claims description 2
- NHGIXSAEPXILDH-QWHCGFSZSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-imidazo[1,2-a]pyridin-3-yl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C=2N3C=CC=CC3=NC=2)=C(C(=O)NC2)C2=C1F NHGIXSAEPXILDH-QWHCGFSZSA-N 0.000 claims description 2
- BRUXXXWLFWMGMH-UONOGXRCSA-N 6-[[(1r,2s)-2-aminocyclohexyl]amino]-7-fluoro-4-pyrazolo[1,5-a]pyridin-3-yl-1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound N[C@H]1CCCC[C@H]1NC1=NC(C2=C3C=CC=CN3N=C2)=C(C(=O)NC2)C2=C1F BRUXXXWLFWMGMH-UONOGXRCSA-N 0.000 claims description 2
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Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ601267A (en) * | 2009-12-23 | 2014-03-28 | Takeda Pharmaceutical | Fused heteroaromatic pyrrolidinones as syk inhibitors |
| EP2691399B1 (en) * | 2011-03-28 | 2016-07-13 | F.Hoffmann-La Roche Ag | Thiazolopyrimidine compounds |
| EP2723739B1 (en) | 2011-06-22 | 2016-08-24 | Takeda Pharmaceutical Company Limited | Substituted 6-aza-isoindolin-1-one derivatives |
| EP2900639B1 (en) * | 2012-09-27 | 2017-08-16 | Portola Pharmaceuticals, Inc. | Bicyclic dihydropyridone kinase inhibitors |
| WO2014051654A2 (en) * | 2012-09-27 | 2014-04-03 | Portola Pharmaceuticals, Inc. | Bicyclic oxa-lactam kinase inhibitors |
| AU2013337717B2 (en) | 2012-11-01 | 2018-10-25 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using PI3 kinase isoform modulators |
| WO2014151386A1 (en) | 2013-03-15 | 2014-09-25 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| CA2914284A1 (en) | 2013-05-30 | 2014-12-04 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| SG11201600373YA (en) | 2013-07-31 | 2016-02-26 | Gilead Sciences Inc | Syk inhibitors |
| US9751888B2 (en) | 2013-10-04 | 2017-09-05 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| PT3052485T (pt) | 2013-10-04 | 2021-10-22 | Infinity Pharmaceuticals Inc | Compostos heterocíclicos e suas utilizações |
| US20160244452A1 (en) | 2013-10-21 | 2016-08-25 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| TWI735853B (zh) | 2013-12-23 | 2021-08-11 | 美商克洛諾斯生技有限公司 | 脾酪胺酸激酶抑制劑 |
| WO2015131080A1 (en) * | 2014-02-28 | 2015-09-03 | Nimbus Lakshmi, Inc. | Tyk2 inhibitors and uses thereof |
| MX382033B (es) | 2014-03-19 | 2025-03-13 | Infinity Pharmaceuticals Inc | Compuestos heterocíclicos para utilizarlos en el tratamiento de trastornos mediados por pi3k-gamma. |
| US10245262B2 (en) | 2014-04-01 | 2019-04-02 | The University Of Queensland | Immunological reagents and uses therefor |
| US20150320754A1 (en) | 2014-04-16 | 2015-11-12 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| JP2017518737A (ja) * | 2014-04-21 | 2017-07-13 | ミレニアム ファーマシューティカルズ， インコーポレイテッドＭｉｌｌｅｎｎｉｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ， Ｉｎｃ． | ＳＹＫ標的治療薬のための抗ｐＳＹＫ抗体分子及びその使用 |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN107278203B (zh) | 2014-12-05 | 2020-05-19 | 阵列生物制药公司 | 作为JANUS激酶抑制剂的4,6-取代的吡唑并[1,5-a]吡嗪 |
| TN2017000080A1 (en) * | 2014-12-18 | 2018-07-04 | Takeda Pharmaceuticals Co | Solid state forms of fused heteroaromatic pyrrolidinones |
| TWI788655B (zh) * | 2015-02-27 | 2023-01-01 | 美商林伯士拉克許米公司 | 酪胺酸蛋白質激酶2(tyk2)抑制劑及其用途 |
| TWI707852B (zh) * | 2015-09-02 | 2020-10-21 | 美商林伯士拉克許米公司 | Tyk2 抑制劑及其用途 |
| WO2017048702A1 (en) | 2015-09-14 | 2017-03-23 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| GB201604970D0 (en) | 2016-03-23 | 2016-05-04 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
| WO2017205801A1 (en) * | 2016-05-27 | 2017-11-30 | Takeda Pharmaceutical Company Limited | Combination of immunotherapy agents and spleen tyrosine kinase inhibitors |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2017216726A1 (en) | 2016-06-13 | 2017-12-21 | Glaxosmithkline Intellectual Property Development Limited | Substituted pyridines as inhibitors of dnmt1 |
| SG11201811237WA (en) | 2016-06-24 | 2019-01-30 | Infinity Pharmaceuticals Inc | Combination therapies |
| US20190231757A1 (en) * | 2016-07-13 | 2019-08-01 | Takeda Pharmaceutical Company Limited | Combination of spleen tyrosine kinase inhibitors and other therapeutic agents |
| AU2017325844A1 (en) | 2016-09-14 | 2019-03-07 | Gilead Sciences, Inc. | SYK inhibitors |
| TW201822764A (zh) | 2016-09-14 | 2018-07-01 | 美商基利科學股份有限公司 | Syk抑制劑 |
| WO2018195471A1 (en) | 2017-04-21 | 2018-10-25 | Gilead Sciences, Inc. | Syk inhibitors in combination with hypomethylating agents |
| AU2018286247B2 (en) * | 2017-06-14 | 2021-12-23 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Syk inhibitor and use method therefor |
| TWI782056B (zh) | 2017-07-14 | 2022-11-01 | 日商鹽野義製藥股份有限公司 | 具有ｍｇａｔ２抑制活性的縮合環衍生物 |
| US11174254B2 (en) * | 2017-09-28 | 2021-11-16 | Yangtze River Pharmaceutical Group Co., Ltd. | Aniline-substituted 1,2-dihydropyrrol[3,4-C]pyridin/pyrimidin-3-one derivative and use thereof |
| KR20190043437A (ko) | 2017-10-18 | 2019-04-26 | 씨제이헬스케어 주식회사 | 단백질 키나제 억제제로서의 헤테로고리 화합물 |
| CN111194319A (zh) * | 2017-10-19 | 2020-05-22 | 拜耳动物保健有限责任公司 | 稠合的杂芳族吡咯烷酮类化合物用于治疗和预防动物中的疾病的用途 |
| WO2019088039A1 (en) | 2017-10-30 | 2019-05-09 | Takeda Pharmaceutical Company Limited | Treatment of acute myeloid leukemia |
| CN111295384B (zh) * | 2018-10-10 | 2022-08-12 | 江苏豪森药业集团有限公司 | 双环类衍生物抑制剂、其制备方法和应用 |
| KR102195348B1 (ko) | 2018-11-15 | 2020-12-24 | 에이치케이이노엔 주식회사 | 단백질 키나제 억제제로서의 신규 화합물 및 이를 포함하는 약제학적 조성물 |
| MX2021008050A (es) | 2019-01-11 | 2021-08-05 | Shionogi & Co | Derivado de dihidropirazolopirazinona que tiene actividad inhibidora de monoacilglicerol aciltransferasa 2 (mgat2). |
| US11339168B2 (en) * | 2019-02-22 | 2022-05-24 | Kronos Bio, Inc. | Crystalline forms of 6-(6-aminopyrazin-2-yl)-N-(4-(4-(oxetan-3-yl)piperazin-1-yl)phenyl)imidazo[1,2-a]pyrazin-8-amine as Syk inhibitors |
| US20210395247A1 (en) * | 2019-03-18 | 2021-12-23 | Shanghai Haiyan Pharmaceutical Technology Co., Ltd. | Btk inhibitors, pharmaceutically acceptable salts, polymorphs and application thereof |
| EA202192575A1 (ru) | 2019-03-21 | 2022-01-14 | Онксео | Соединения dbait в сочетании с ингибиторами киназ для лечения рака |
| CN114761006A (zh) | 2019-11-08 | 2022-07-15 | Inserm(法国国家健康医学研究院) | 对激酶抑制剂产生耐药性的癌症的治疗方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| WO2022019920A1 (en) | 2020-07-24 | 2022-01-27 | Verastem, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| CN116096369B (zh) * | 2020-09-01 | 2025-09-16 | 上海海雁医药科技有限公司 | 布鲁顿酪氨酸激酶抑制剂的多晶型物及其制备方法和应用 |
| WO2022127753A1 (zh) * | 2020-12-18 | 2022-06-23 | 山东轩竹医药科技有限公司 | 稠环类AhR抑制剂 |
| US20240174662A1 (en) * | 2021-02-01 | 2024-05-30 | Janssen Biotech, Inc. | Small molecule inhibitors of salt inducible kinases |
| EP4291235A4 (en) | 2021-02-12 | 2025-01-08 | Nimbus Saturn, Inc. | HPK1 ANTAGONISTS AND USES THEREOF |
| US11926625B2 (en) | 2021-03-05 | 2024-03-12 | Nimbus Saturn, Inc. | HPK1 antagonists and uses thereof |
| WO2022213062A1 (en) * | 2021-03-29 | 2022-10-06 | Nimbus Saturn, Inc. | Hpk1 antagonists and uses thereof |
| WO2023079291A1 (en) * | 2021-11-04 | 2023-05-11 | Redx Pharma Plc | Ddr1 and ddr2 inhibitors for the treatement of cancer and fibrotic diseases |
| CN114907992B (zh) | 2022-05-18 | 2023-06-16 | 塔里木大学 | 拮抗植物病原菌的菌株c11及其应用 |
Family Cites Families (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63107966A (ja) | 1986-05-22 | 1988-05-12 | Fujisawa Pharmaceut Co Ltd | ピリミジン誘導体 |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| US5272158A (en) | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5238950A (en) * | 1991-12-17 | 1993-08-24 | Schering Corporation | Inhibitors of platelet-derived growth factor |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| EP1054004B1 (en) * | 1997-12-15 | 2008-07-16 | Astellas Pharma Inc. | Novel pyrimidine-5-carboxamide derivatives |
| WO1999032479A1 (en) | 1997-12-23 | 1999-07-01 | Alcon Laboratories, Inc. | Phthalimide-piperidine, -pyrrolidine and -azepine derivatives, their preparation and their use as muscarinic receptor (ant-)agonists |
| ATE288420T1 (de) | 1999-06-09 | 2005-02-15 | Yamanouchi Pharma Co Ltd | Neuartige heterocyclische carboxamid-derivate |
| FR2796946A1 (fr) | 1999-07-30 | 2001-02-02 | Aventis Pharma Sa | Nouveaux derives 8-carbonyl chromanes, leur preparation et leur utilisation en therapeutique |
| GB9918035D0 (en) | 1999-07-30 | 1999-09-29 | Novartis Ag | Organic compounds |
| BR0016415A (pt) | 1999-12-16 | 2002-12-24 | Alcon Inc | Inibidores de adenosina cinase para o tratamento de dano retinal e de nervo ótico |
| IL150594A0 (en) | 2000-01-07 | 2003-02-12 | Ustav Ex Botan Adademie Ved Ce | Purine derivatives, process for their preparation and use |
| AU2001232271A1 (en) | 2000-02-14 | 2001-08-20 | Japan Tobacco Inc. | Preventives/remedies for postoperative stress |
| JP2001302667A (ja) | 2000-04-28 | 2001-10-31 | Bayer Ag | イミダゾピリミジン誘導体およびトリアゾロピリミジン誘導体 |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| US7105667B2 (en) * | 2001-05-01 | 2006-09-12 | Bristol-Myers Squibb Co. | Fused heterocyclic compounds and use thereof |
| PE20030008A1 (es) | 2001-06-19 | 2003-01-22 | Bristol Myers Squibb Co | Inhibidores duales de pde 7 y pde 4 |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| US20040235867A1 (en) | 2001-07-24 | 2004-11-25 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| US20030158195A1 (en) | 2001-12-21 | 2003-08-21 | Cywin Charles L. | 1,6 naphthyridines useful as inhibitors of SYK kinase |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| GB0206215D0 (en) * | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
| AU2003262642B2 (en) | 2002-08-14 | 2010-06-17 | Vertex Pharmaceuticals Incorporated | Protein kinase inhibitors and uses thereof |
| AU2003286711A1 (en) | 2002-10-25 | 2004-05-13 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| EP1560824A1 (en) | 2002-11-05 | 2005-08-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of jak and other protein kinases |
| JP2006522125A (ja) | 2003-03-25 | 2006-09-28 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なチアゾール |
| CA2518465A1 (en) | 2003-03-25 | 2004-10-14 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| CA2523125A1 (en) | 2003-03-25 | 2004-10-14 | Vertex Pharmaceuticals Incorporated | Thiazoles useful as inhibitors of protein kinases |
| WO2005012294A1 (en) | 2003-07-30 | 2005-02-10 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| US7320992B2 (en) | 2003-08-25 | 2008-01-22 | Amgen Inc. | Substituted 2,3-dihydro-1h-isoindol-1-one derivatives and methods of use |
| WO2005039564A1 (en) | 2003-10-02 | 2005-05-06 | Vertex Pharmaceuticals Incorporated | Phthalimide compounds useful as protein kinase inhibitors |
| CN1905873A (zh) * | 2003-11-19 | 2007-01-31 | 阵列生物制药公司 | Mek的杂环抑制剂及其使用方法 |
| WO2005056524A2 (en) | 2003-12-09 | 2005-06-23 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| US8057815B2 (en) * | 2004-04-19 | 2011-11-15 | Portola Pharmaceuticals, Inc. | Methods of treatment with Syk inhibitors |
| JP2008511659A (ja) | 2004-09-01 | 2008-04-17 | ライジェル ファーマシューティカルズ， インコーポレイテッド | ２，４−ピリミジンジアミン化合物の合成 |
| SI1814878T1 (sl) | 2004-11-24 | 2012-06-29 | Rigel Pharmaceuticals Inc | Spojine spiro-2,4-pirimidindiamina in njihova uporaba |
| US20060128710A1 (en) | 2004-12-09 | 2006-06-15 | Chih-Hung Lee | Antagonists to the vanilloid receptor subtype 1 (VR1) and uses thereof |
| RU2007140733A (ru) | 2005-04-06 | 2009-05-20 | Айрм Ллк (Bm) | Диариламинсодержащие соединения и композиции, и их применение в качестве модуляторов ядерных рецепторов стероидного гормона |
| KR20080011199A (ko) * | 2005-04-19 | 2008-01-31 | 교와 핫꼬 고교 가부시끼가이샤 | 질소 함유 복소환 화합물 |
| WO2006129100A1 (en) | 2005-06-03 | 2006-12-07 | Glaxo Group Limited | Novel compounds |
| WO2007002781A2 (en) | 2005-06-28 | 2007-01-04 | Bausch & Lomb Incorporated | Preparations comprising arylazine substituted with a carbonylic moiety to increase the activity of gelatinase a in ocular cells |
| US20070185063A1 (en) | 2005-08-23 | 2007-08-09 | Idenix Pharmaceuticals, Inc. | Seven-membered ring nucleosides |
| WO2007023382A2 (en) | 2005-08-25 | 2007-03-01 | Pfizer Inc. | Pyrimidine amino pyrazole compounds, potent kinase inhibitors |
| JP2009511528A (ja) * | 2005-10-13 | 2009-03-19 | グラクソ グループ リミテッド | Ｓｙｋ阻害物質としてのピロロピリミジン誘導体群 |
| WO2007053844A2 (en) | 2005-10-31 | 2007-05-10 | Rigel Pharmaceuticals, Inc. | Compositions and methods for treating inflammatory disorders |
| WO2007070872A1 (en) * | 2005-12-15 | 2007-06-21 | Rigel Pharmaceuticals, Inc. | Kinase inhibitors and their uses |
| UA95940C2 (uk) | 2006-01-17 | 2011-09-26 | Вертекс Фармасьютикалс Інкорпорейтед | Азаіндоли як інгібітори кіназ януса |
| CL2007002617A1 (es) | 2006-09-11 | 2008-05-16 | Sanofi Aventis | Compuestos derivados de pirrolo[2,3-b]pirazin-6-ilo; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar inflamacion de las articulaciones, artritis reumatoide, tumores, linfoma de las celulas del manto. |
| JPWO2008047831A1 (ja) * | 2006-10-17 | 2010-02-25 | 協和発酵キリン株式会社 | Ｊａｋ阻害剤 |
| MX337906B (es) | 2006-10-19 | 2016-03-28 | Signal Pharm Llc | Compuestos de heteroarilo, composiciones de los mismos, y su uso como inhibidores de proteina cinasas. |
| WO2008057402A2 (en) | 2006-11-02 | 2008-05-15 | Cytovia, Inc. | N-aryl-isoxazolopyrimidin-4-amines and related compounds as activators of caspases and inducers of apoptosis and the use thereof |
| ATE540041T1 (de) | 2006-11-21 | 2012-01-15 | Rigel Pharmaceuticals Inc | Prodrug-salze von 2,4-pyrimidindiaminverbindungen und anwendungen davon |
| CA2673965A1 (en) | 2006-12-28 | 2008-07-10 | Taisho Pharmaceutical Co., Ltd. | Pyrazolopyrimidine compound |
| EP2114940A1 (en) * | 2007-02-09 | 2009-11-11 | AstraZeneca AB | Aza-isoindolones and their use as metabotropic glutamate receptor potentiators - 613 |
| MX2009010207A (es) | 2007-03-23 | 2009-10-19 | Schering Corp | Peptidos de hidrazido como inhibidores de proteasa ns3 de virus de hepatitis c. |
| KR20100033981A (ko) | 2007-06-03 | 2010-03-31 | 벤더르빌트 유니버시티 | 벤즈아미드 대사성 글루타민산염 수용체5 양성 알로스테릭 조절자 및 이의 제조 및 사용방법 |
| WO2009026107A1 (en) | 2007-08-17 | 2009-02-26 | Portola Pharmaceuticals, Inc. | Protein kinase inhibitors |
| JP2009067729A (ja) | 2007-09-14 | 2009-04-02 | Kyowa Hakko Kirin Co Ltd | Ｈｓｐ９０ファミリー蛋白質阻害剤 |
| CA2705303A1 (en) | 2007-11-07 | 2009-05-14 | Foldrx Pharmaceuticals, Inc. | Modulation of protein trafficking |
| CA2710118A1 (en) | 2007-12-20 | 2009-07-02 | Cellzome Limited | Sulfamides as zap-70 inhibitors |
| TW200938542A (en) * | 2008-02-01 | 2009-09-16 | Irm Llc | Compounds and compositions as kinase inhibitors |
| WO2009102468A1 (en) | 2008-02-13 | 2009-08-20 | Cgi Pharmaceuticals, Inc. | 6-aryl-imidaz0[l, 2-a] pyrazine derivatives, method of making, and method of use thereof |
| MX2010009159A (es) | 2008-02-22 | 2010-09-14 | Rigel Pharmaceuticals Inc | Uso de 2,4-pirimidindiaminas para el tratamiento de aterosclerosis. |
| US8436005B2 (en) | 2008-04-03 | 2013-05-07 | Abbott Laboratories | Macrocyclic pyrimidine derivatives |
| HRP20161310T1 (hr) | 2008-04-16 | 2016-12-02 | Portola Pharmaceuticals, Inc. | 2,6-diamino-pirimidin-5-il-karboksamidi kao inhibitori syk ili jak kinaza |
| SG165655A1 (en) | 2008-04-16 | 2010-11-29 | Portola Pharm Inc | 2, 6-diamino- pyrimidin- 5-yl-carboxamides as syk or JAK kinases inhibitors |
| JP2011522865A (ja) | 2008-06-13 | 2011-08-04 | ノバルティス アーゲー | Ｉａ心不全および癌の治療に有用なプロテインキナーゼｄ阻害剤としての２，４’−ビピリジニル化合物 |
| CA2731926A1 (en) | 2008-08-05 | 2010-02-11 | Boehringer Ingelheim International Gmbh | 4-dimethylamino-phenyl-substituted naphthyridines, and use thereof as medicaments |
| US20110201608A1 (en) | 2008-08-05 | 2011-08-18 | Boehringer Ingelheim International Gmbh | Substituted naphthyridines and use thereof as medicines |
| TWI453207B (zh) | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| PE20120121A1 (es) | 2008-12-08 | 2012-02-20 | Gilead Connecticut Inc | Derivados de imidazopirazina como inhibidores de syk |
| EP2443106A1 (en) | 2009-06-18 | 2012-04-25 | Cellzome Limited | Heterocyclylaminopyrimidines as kinase inhibitors |
| EP2512246B1 (en) | 2009-12-17 | 2015-09-30 | Merck Sharp & Dohme Corp. | Aminopyrimidines as syk inhibitors |
| KR101445012B1 (ko) | 2009-12-17 | 2014-09-26 | 머크 샤프 앤드 돔 코포레이션 | Ｓｙｋ 억제제로서의 아미노피리미딘 |
| NZ601267A (en) | 2009-12-23 | 2014-03-28 | Takeda Pharmaceutical | Fused heteroaromatic pyrrolidinones as syk inhibitors |
| GB201007203D0 (en) | 2010-04-29 | 2010-06-16 | Glaxo Group Ltd | Novel compounds |
| EP2723739B1 (en) | 2011-06-22 | 2016-08-24 | Takeda Pharmaceutical Company Limited | Substituted 6-aza-isoindolin-1-one derivatives |
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