RU2014130214A - Пиримидин-2, 4-диаминовые производные в качестве ингибиторов киназы - Google Patents
Пиримидин-2, 4-диаминовые производные в качестве ингибиторов киназы Download PDFInfo
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- RU2014130214A RU2014130214A RU2014130214A RU2014130214A RU2014130214A RU 2014130214 A RU2014130214 A RU 2014130214A RU 2014130214 A RU2014130214 A RU 2014130214A RU 2014130214 A RU2014130214 A RU 2014130214A RU 2014130214 A RU2014130214 A RU 2014130214A
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- Prior art keywords
- methyl
- amino
- pyrazol
- chloro
- pyrimidin
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- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 title claims 5
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 14
- 125000001424 substituent group Chemical group 0.000 claims abstract 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract 13
- 125000005843 halogen group Chemical group 0.000 claims abstract 10
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 8
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 28
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 28
- -1 (5-chloro-4 - (((1- (methylsulfonyl) pyrrolidin-2-yl) methyl) amino) pyrimidin-2-yl) amino Chemical group 0.000 claims 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 230000000155 isotopic effect Effects 0.000 claims 6
- 239000010802 sludge Substances 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- LBEISLAZIABLCY-UHFFFAOYSA-N hydron;pyrimidine-2,4-diamine;chloride Chemical compound Cl.NC1=CC=NC(N)=N1 LBEISLAZIABLCY-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- CDVJKQIIUPKHAL-CYBMUJFWSA-N (2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]-n-cyclopropylpyrrolidine-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)NC2CC2)=N1 CDVJKQIIUPKHAL-CYBMUJFWSA-N 0.000 claims 1
- CMWWRTGOBSKAJZ-GFCCVEGCSA-N (2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]-n-ethylpyrrolidine-1-carboxamide Chemical compound CCNC(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl CMWWRTGOBSKAJZ-GFCCVEGCSA-N 0.000 claims 1
- ONIJLSBDIIRAFS-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl ONIJLSBDIIRAFS-CYBMUJFWSA-N 0.000 claims 1
- PSVYKMBUIKACRQ-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCCC2)C(=O)C=C)=N1 PSVYKMBUIKACRQ-CYBMUJFWSA-N 0.000 claims 1
- ANCXLJLCQQIKKP-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound CN(C)CC(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl ANCXLJLCQQIKKP-CYBMUJFWSA-N 0.000 claims 1
- QZCQRTWGRNBEDH-LLVKDONJSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-2-hydroxyethanone Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)CO)=N1 QZCQRTWGRNBEDH-LLVKDONJSA-N 0.000 claims 1
- HKVIEWIXNYVQSS-GFCCVEGCSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl HKVIEWIXNYVQSS-GFCCVEGCSA-N 0.000 claims 1
- ZOPYHDHDONFLRQ-GFCCVEGCSA-N 1-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)C=C)=N1 ZOPYHDHDONFLRQ-GFCCVEGCSA-N 0.000 claims 1
- KFULROJDRYWQNS-CQSZACIVSA-N 1-[(2r)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl KFULROJDRYWQNS-CQSZACIVSA-N 0.000 claims 1
- DEAIETUFAWQIJP-CQSZACIVSA-N 1-[(2r)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCCC2)C(=O)C=C)=N1 DEAIETUFAWQIJP-CQSZACIVSA-N 0.000 claims 1
- ZDVMTKYERGFKSH-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl ZDVMTKYERGFKSH-CYBMUJFWSA-N 0.000 claims 1
- CPJRKQDKFMIEGI-CYBMUJFWSA-N 1-[(2r)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)C=C)=N1 CPJRKQDKFMIEGI-CYBMUJFWSA-N 0.000 claims 1
- ONIJLSBDIIRAFS-ZDUSSCGKSA-N 1-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC[C@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl ONIJLSBDIIRAFS-ZDUSSCGKSA-N 0.000 claims 1
- PSVYKMBUIKACRQ-ZDUSSCGKSA-N 1-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCCC2)C(=O)C=C)=N1 PSVYKMBUIKACRQ-ZDUSSCGKSA-N 0.000 claims 1
- HKVIEWIXNYVQSS-LBPRGKRZSA-N 1-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl HKVIEWIXNYVQSS-LBPRGKRZSA-N 0.000 claims 1
- ZOPYHDHDONFLRQ-LBPRGKRZSA-N 1-[(2s)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)C(=O)C=C)=N1 ZOPYHDHDONFLRQ-LBPRGKRZSA-N 0.000 claims 1
- KFULROJDRYWQNS-AWEZNQCLSA-N 1-[(2s)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCCC[C@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl KFULROJDRYWQNS-AWEZNQCLSA-N 0.000 claims 1
- DEAIETUFAWQIJP-AWEZNQCLSA-N 1-[(2s)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCCC2)C(=O)C=C)=N1 DEAIETUFAWQIJP-AWEZNQCLSA-N 0.000 claims 1
- ZDVMTKYERGFKSH-ZDUSSCGKSA-N 1-[(2s)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound CC(=O)N1CCC[C@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl ZDVMTKYERGFKSH-ZDUSSCGKSA-N 0.000 claims 1
- CPJRKQDKFMIEGI-ZDUSSCGKSA-N 1-[(2s)-2-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)C(=O)C=C)=N1 CPJRKQDKFMIEGI-ZDUSSCGKSA-N 0.000 claims 1
- UYUBGNTYPRFJIZ-GFCCVEGCSA-N 1-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-2-(dimethylamino)ethanone Chemical compound C1N(C(=O)CN(C)C)CC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl UYUBGNTYPRFJIZ-GFCCVEGCSA-N 0.000 claims 1
- XLDJUSNJZDOQHI-LLVKDONJSA-N 1-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl XLDJUSNJZDOQHI-LLVKDONJSA-N 0.000 claims 1
- XYFZTXIUUMNXCR-LLVKDONJSA-N 1-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CC2)C(=O)C=C)=N1 XYFZTXIUUMNXCR-LLVKDONJSA-N 0.000 claims 1
- OEURTTGUJDNBDQ-GFCCVEGCSA-N 1-[(3r)-3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl OEURTTGUJDNBDQ-GFCCVEGCSA-N 0.000 claims 1
- RPMAACYUOMABIE-GFCCVEGCSA-N 1-[(3r)-3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CC2)C(=O)C=C)=N1 RPMAACYUOMABIE-GFCCVEGCSA-N 0.000 claims 1
- XLDJUSNJZDOQHI-NSHDSACASA-N 1-[(3s)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl XLDJUSNJZDOQHI-NSHDSACASA-N 0.000 claims 1
- XYFZTXIUUMNXCR-NSHDSACASA-N 1-[(3s)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2CN(CC2)C(=O)C=C)=N1 XYFZTXIUUMNXCR-NSHDSACASA-N 0.000 claims 1
- OEURTTGUJDNBDQ-LBPRGKRZSA-N 1-[(3s)-3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@H]1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl OEURTTGUJDNBDQ-LBPRGKRZSA-N 0.000 claims 1
- RPMAACYUOMABIE-LBPRGKRZSA-N 1-[(3s)-3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@H]2CN(CC2)C(=O)C=C)=N1 RPMAACYUOMABIE-LBPRGKRZSA-N 0.000 claims 1
- DFZBGSUDSUAWFV-UHFFFAOYSA-N 1-[3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]azetidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl DFZBGSUDSUAWFV-UHFFFAOYSA-N 0.000 claims 1
- ICTNRLPCFQGQLY-UHFFFAOYSA-N 1-[3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]azetidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl ICTNRLPCFQGQLY-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- CEVFPLQCSHTYJP-GFCCVEGCSA-N 2-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]acetonitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CC#N)=N1 CEVFPLQCSHTYJP-GFCCVEGCSA-N 0.000 claims 1
- WIAHVYCQTMEZOK-JSGCOSHPSA-N 2-[(2s,4s)-4-fluoro-2-[[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]acetonitrile Chemical compound N1=C(NC[C@H]2N(C[C@@H](F)C2)CC#N)C(C)=CN=C1NC=1C=NN(C)C=1 WIAHVYCQTMEZOK-JSGCOSHPSA-N 0.000 claims 1
- FGMDDPURZPCLLZ-LLVKDONJSA-N 2-[(3r)-3-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CCO)CC2)=N1 FGMDDPURZPCLLZ-LLVKDONJSA-N 0.000 claims 1
- PCIBCIDUZFCAMU-QGZVFWFLSA-N 2-[4-[[4-[[(2r)-1-(3-cyanopropanoyl)pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-propan-2-ylacetamide Chemical compound C1=NN(CC(=O)NC(C)C)C=C1NC1=NC=CC(NC[C@@H]2N(CCC2)C(=O)CCC#N)=N1 PCIBCIDUZFCAMU-QGZVFWFLSA-N 0.000 claims 1
- UHMQNIBBVBVAHP-UHFFFAOYSA-N 2-[4-[[5-chloro-4-[(1-methylsulfonylazetidin-3-yl)methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1N(S(=O)(=O)C)CC1CNC1=NC(NC2=CN(CCO)N=C2)=NC=C1Cl UHMQNIBBVBVAHP-UHFFFAOYSA-N 0.000 claims 1
- UVLYRUPRPSIXDD-GFCCVEGCSA-N 2-[4-[[5-chloro-4-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)S(C)(=O)=O)=N1 UVLYRUPRPSIXDD-GFCCVEGCSA-N 0.000 claims 1
- LYGUHFBRHCGVQV-LLVKDONJSA-N 2-[4-[[5-chloro-4-[[(2r)-pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n,n-dimethylacetamide Chemical compound C1=NN(CC(=O)N(C)C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2NCCC2)=N1 LYGUHFBRHCGVQV-LLVKDONJSA-N 0.000 claims 1
- ZFEULNSJXLXHJH-SNVBAGLBSA-N 2-[4-[[5-chloro-4-[[(2r)-pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC[C@@H]2NCCC2)=N1 ZFEULNSJXLXHJH-SNVBAGLBSA-N 0.000 claims 1
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- ZFEULNSJXLXHJH-JTQLQIEISA-N 2-[4-[[5-chloro-4-[[(2s)-pyrrolidin-2-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]-n-methylacetamide Chemical compound C1=NN(CC(=O)NC)C=C1NC1=NC=C(Cl)C(NC[C@H]2NCCC2)=N1 ZFEULNSJXLXHJH-JTQLQIEISA-N 0.000 claims 1
- OFYGBRWUMAUGIT-JTQLQIEISA-N 2-[4-[[5-chloro-4-[[(3s)-pyrrolidin-3-yl]methylamino]pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CNCC2)=N1 OFYGBRWUMAUGIT-JTQLQIEISA-N 0.000 claims 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
- SXIAJLYTRNHUQT-CQSZACIVSA-N 2-n-[1-(2,2-difluoroethyl)pyrazol-4-yl]-5-methyl-4-n-[[(3r)-1-(2-methylsulfonylethyl)pyrrolidin-3-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@@H]2CN(CCS(C)(=O)=O)CC2)C(C)=CN=C1NC=1C=NN(CC(F)F)C=1 SXIAJLYTRNHUQT-CQSZACIVSA-N 0.000 claims 1
- GCHHFXPKDXUPTF-CYBMUJFWSA-N 3-[(2r)-2-[[[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=CC(NC[C@@H]2N(CCC2)C(=O)CC#N)=N1 GCHHFXPKDXUPTF-CYBMUJFWSA-N 0.000 claims 1
- HJJHAJDOJOFIDR-GFCCVEGCSA-N 3-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]-3-oxopropanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)C(=O)CC#N)=N1 HJJHAJDOJOFIDR-GFCCVEGCSA-N 0.000 claims 1
- VLTFEEKKKFCFID-CYBMUJFWSA-N 3-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CCC#N)=N1 VLTFEEKKKFCFID-CYBMUJFWSA-N 0.000 claims 1
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- JJVILJFRZFPFTK-LBPRGKRZSA-N 5-chloro-4-n-[[(2s)-1-ethenylsulfonylpyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(CCC2)S(=O)(=O)C=C)=N1 JJVILJFRZFPFTK-LBPRGKRZSA-N 0.000 claims 1
- QNKVNZUDWNEQOQ-LBPRGKRZSA-N 5-chloro-4-n-[[(2s)-1-ethylpyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound CCN1CCC[C@H]1CNC1=NC(NC2=CN(C)N=C2)=NC=C1Cl QNKVNZUDWNEQOQ-LBPRGKRZSA-N 0.000 claims 1
- JXHCLEKLRIAQOG-JSGCOSHPSA-N 5-chloro-4-n-[[(2s,4s)-4-fluoro-1-(3-methylsulfonylpropyl)pyrrolidin-2-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2N(C[C@@H](F)C2)CCCS(C)(=O)=O)=N1 JXHCLEKLRIAQOG-JSGCOSHPSA-N 0.000 claims 1
- NPDSHYKPRROTSO-LLVKDONJSA-N 5-chloro-4-n-[[(3r)-1-ethenylsulfonylpyrrolidin-3-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2CN(CC2)S(=O)(=O)C=C)=N1 NPDSHYKPRROTSO-LLVKDONJSA-N 0.000 claims 1
- NPDSHYKPRROTSO-NSHDSACASA-N 5-chloro-4-n-[[(3s)-1-ethenylsulfonylpyrrolidin-3-yl]methyl]-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@H]2CN(CC2)S(=O)(=O)C=C)=N1 NPDSHYKPRROTSO-NSHDSACASA-N 0.000 claims 1
- TZLDKSUNDGKMCX-RFVHGSKJSA-N 5-fluoro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.C1=NN(C)C=C1NC1=NC=C(F)C(NC[C@@H]2N(CCC2)S(C)(=O)=O)=N1 TZLDKSUNDGKMCX-RFVHGSKJSA-N 0.000 claims 1
- DAATVZRKBFLUHN-SBSPUUFOSA-N 5-fluoro-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.C1=NN(C)C=C1NC1=NC=C(F)C(NC[C@@H]2NCCC2)=N1 DAATVZRKBFLUHN-SBSPUUFOSA-N 0.000 claims 1
- YTPSQOHQLAJLER-OAHLLOKOSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@@H]2N(CCC2)CCS(C)(=O)=O)C(C)=CN=C1NC=1C=NN(C)C=1 YTPSQOHQLAJLER-OAHLLOKOSA-N 0.000 claims 1
- PTXKOKBZWVETHC-CYBMUJFWSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2r)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@@H]2N(CCC2)S(C)(=O)=O)C(C)=CN=C1NC=1C=NN(C)C=1 PTXKOKBZWVETHC-CYBMUJFWSA-N 0.000 claims 1
- YTPSQOHQLAJLER-HNNXBMFYSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-1-(2-methylsulfonylethyl)pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@H]2N(CCC2)CCS(C)(=O)=O)C(C)=CN=C1NC=1C=NN(C)C=1 YTPSQOHQLAJLER-HNNXBMFYSA-N 0.000 claims 1
- PTXKOKBZWVETHC-ZDUSSCGKSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-1-methylsulfonylpyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine Chemical compound N1=C(NC[C@H]2N(CCC2)S(C)(=O)=O)C(C)=CN=C1NC=1C=NN(C)C=1 PTXKOKBZWVETHC-ZDUSSCGKSA-N 0.000 claims 1
- WBKRTQSFMUHMDY-MERQFXBCSA-N 5-methyl-2-n-(1-methylpyrazol-4-yl)-4-n-[[(2s)-pyrrolidin-2-yl]methyl]pyrimidine-2,4-diamine;hydrochloride Chemical compound Cl.N1=C(NC[C@H]2NCCC2)C(C)=CN=C1NC=1C=NN(C)C=1 WBKRTQSFMUHMDY-MERQFXBCSA-N 0.000 claims 1
- SGSVAYRXUJLLAB-OAHLLOKOSA-N Cc1cnc(Nc2cnn(CC(F)F)c2)nc1NC[C@H]1CCCN1CCC#N Chemical compound Cc1cnc(Nc2cnn(CC(F)F)c2)nc1NC[C@H]1CCCN1CCC#N SGSVAYRXUJLLAB-OAHLLOKOSA-N 0.000 claims 1
- TZLDKSUNDGKMCX-MERQFXBCSA-N Cl.Cn1cc(Nc2ncc(F)c(NC[C@@H]3CCCN3S(C)(=O)=O)n2)cn1 Chemical compound Cl.Cn1cc(Nc2ncc(F)c(NC[C@@H]3CCCN3S(C)(=O)=O)n2)cn1 TZLDKSUNDGKMCX-MERQFXBCSA-N 0.000 claims 1
- XWAIHPHTWPDHKD-AAEUAGOBSA-N Cn1cc(Nc2ncc(Cl)c(NC[C@@H]3C[C@H](F)CN3CCS(C)(=O)=O)n2)cn1 Chemical compound Cn1cc(Nc2ncc(Cl)c(NC[C@@H]3C[C@H](F)CN3CCS(C)(=O)=O)n2)cn1 XWAIHPHTWPDHKD-AAEUAGOBSA-N 0.000 claims 1
- KTNJAVTYORZGMV-INHRHCAVSA-N FC(CN1N=CC(=C1)C1(NC=C(C(=N1)NC[C@H]1N(C[C@H](C1)F)CCS(=O)(=O)C)C)N)F Chemical compound FC(CN1N=CC(=C1)C1(NC=C(C(=N1)NC[C@H]1N(C[C@H](C1)F)CCS(=O)(=O)C)C)N)F KTNJAVTYORZGMV-INHRHCAVSA-N 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 230000001900 immune effect Effects 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- OLGZNLFUXZSMAD-CYBMUJFWSA-N n-[2-[(2r)-2-[[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]methyl]pyrrolidin-1-yl]ethyl]methanesulfonamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC[C@@H]2N(CCC2)CCNS(C)(=O)=O)=N1 OLGZNLFUXZSMAD-CYBMUJFWSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 9
- 125000003342 alkenyl group Chemical group 0.000 abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 0 **N(*)c1c(*)cnc(N*)n1 Chemical compound **N(*)c1c(*)cnc(N*)n1 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Transplantation (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11195662.9 | 2011-12-23 | ||
| EP11195662 | 2011-12-23 | ||
| PCT/EP2012/076371 WO2013092854A1 (en) | 2011-12-23 | 2012-12-20 | Pyrimidine-2,4-diamine derivatives as kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014130214A true RU2014130214A (ru) | 2016-02-10 |
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| RU2014130214A RU2014130214A (ru) | 2011-12-23 | 2012-12-20 | Пиримидин-2, 4-диаминовые производные в качестве ингибиторов киназы |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20150005281A1 (https=) |
| EP (1) | EP2794598A1 (https=) |
| JP (1) | JP2015500862A (https=) |
| KR (1) | KR20140114344A (https=) |
| CN (1) | CN104169272A (https=) |
| AU (1) | AU2012357038B2 (https=) |
| BR (1) | BR112014015723A8 (https=) |
| CA (1) | CA2860095A1 (https=) |
| RU (1) | RU2014130214A (https=) |
| WO (1) | WO2013092854A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2641895C2 (ru) * | 2012-05-24 | 2018-01-23 | Целльзом Лимитид | ГЕТЕРОЦИКЛИЛЬНЫЕ ПИРИМИДИНОВЫЕ АНАЛОГИ В КАЧЕСТВЕ ИНГИБИТОРОВ Tук2 |
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| AR094537A1 (es) * | 2013-11-07 | 2015-08-12 | Bristol Myers Squibb Co | COMPUESTOS DE PIRIDILO SUSTITUIDOS CON ALQUILAMIDA ÚTILES COMO MODULADORES DE LAS RESPUESTAS DE IL-12, IL-23 Y/O IFNa |
| WO2015082583A1 (en) * | 2013-12-05 | 2015-06-11 | F. Hoffmann-La Roche Ag | Heteroaryl pyridone and aza-pyridone compounds with electrophilic functionality |
| EP3082819B1 (en) | 2013-12-20 | 2020-06-17 | Signal Pharmaceuticals, LLC | Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith |
| MX2016012574A (es) | 2014-03-28 | 2017-09-26 | Calitor Sciences Llc | Compuestos heteroarilo sustituidos y metodos de uso. |
| US10106507B2 (en) | 2014-08-03 | 2018-10-23 | H. Lee Moffitt Cancer Center and Research Insitute, Inc. | Potent dual BRD4-kinase inhibitors as cancer therapeutics |
| WO2017044434A1 (en) | 2015-09-11 | 2017-03-16 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
| US10738016B2 (en) | 2015-10-13 | 2020-08-11 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | BRD4-kinase inhibitors as cancer therapeutics |
| AU2018337138B2 (en) * | 2017-09-21 | 2021-04-01 | Beijing Scitech-Mq Pharmaceuticals Limited | 2-substituted pyrazole amino-4-substituted amino-5-pyrimidine formamide compound, composition, and application thereof |
| CN109535132B (zh) * | 2017-09-21 | 2021-07-20 | 北京赛特明强医药科技有限公司 | 2-取代吡唑氨基-4-取代氨基-5-嘧啶甲酰胺类化合物、组合物及其应用 |
| CN110734427B (zh) * | 2018-07-20 | 2021-01-15 | 北京赛特明强医药科技有限公司 | 含烯基的嘧啶甲酰胺类化合物、组合物及其应用 |
| WO2020187292A1 (zh) * | 2019-03-19 | 2020-09-24 | 北京赛特明强医药科技有限公司 | 2-取代吡唑氨基-4-取代氨基-5-嘧啶甲酰胺类化合物、组合物及其应用 |
| CN111004215B (zh) * | 2019-12-22 | 2022-08-09 | 华北理工大学 | 2,4-取代嘧啶类衍生物及其制备方法和在制备抗肿瘤药物中的应用 |
| WO2025166161A1 (en) * | 2024-02-02 | 2025-08-07 | Deciphera Pharmaceuticals, Llc | Ulk inhibitors and methods of use thereof |
| WO2025166124A1 (en) * | 2024-02-02 | 2025-08-07 | Deciphera Pharmaceuticals, Llc | Ulk inhibitors and methods of use thereof |
| CN120698987B (zh) * | 2025-06-20 | 2026-04-17 | 大连医科大学 | 2-芳氨基嘧啶类化合物及其应用 |
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| DE69837529T2 (de) | 1997-02-12 | 2007-07-26 | Electrophoretics Ltd., Cobham | Proteinmarker für lungenkrebs und deren verwendung |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| SK288365B6 (sk) | 1999-02-10 | 2016-07-01 | Astrazeneca Ab | Medziprodukty pre chinazolínové deriváty ako inhibítory angiogenézy |
| CZ301689B6 (cs) | 1999-11-05 | 2010-05-26 | Astrazeneca Ab | Derivát chinazolinu a farmaceutický prostredek, který ho obsahuje |
| EP1382339B1 (en) | 1999-12-10 | 2007-12-05 | Pfizer Products Inc. | Compositions containing pyrrolo ¬2,3-d pyrimidine derivatives |
| SI1255752T1 (sl) | 2000-02-15 | 2007-12-31 | Pharmacia & Upjohn Co Llc | S pirolom substituirani zaviralci 2-indolinon protein kinaza |
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| AU2006327871A1 (en) | 2005-12-21 | 2007-06-28 | Pfizer Products Inc. | Pyrimidine derivatives for the treatment of abnormal cell growth |
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| JP2010510211A (ja) | 2006-11-16 | 2010-04-02 | ファーマコペイア・リミテッド・ライアビリティ・カンパニー | 免疫抑制用７−置換プリン誘導体 |
| DE102007010801A1 (de) | 2007-03-02 | 2008-09-04 | Bayer Cropscience Ag | Diaminopyrimidine als Fungizide |
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| BRPI0810411B8 (pt) | 2007-04-18 | 2021-05-25 | Pfizer Prod Inc | derivados de sulfonil amida para o tratamento de crescimento celular anormal, seu sos, bem como composição farmacêutica |
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| EA024109B1 (ru) | 2008-04-16 | 2016-08-31 | Портола Фармасьютиклз, Инк. | Ингибиторы протеинкиназ |
| JP2012501982A (ja) * | 2008-09-03 | 2012-01-26 | バイエル・クロップサイエンス・アーゲー | 殺真菌剤として使用するためのチエニルアミノピリミジン |
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| ES2555982T3 (es) | 2009-01-15 | 2016-01-12 | Rigel Pharmaceuticals, Inc. | Inhibidores de la proteína quinasa C y usos de los mismos |
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| AR076550A1 (es) * | 2009-05-06 | 2011-06-22 | Portola Pharm Inc | Inhibidores de la janus tirosina kinasa (jak) |
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| EP2475648A1 (en) | 2009-09-11 | 2012-07-18 | Cellzome Limited | Ortho substituted pyrimidine compounds as jak inhibitors |
| US9242987B2 (en) | 2009-10-20 | 2016-01-26 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as JAK inhibitors |
| BR112012027803A2 (pt) | 2010-04-30 | 2016-08-09 | Cellzome Ltd | compostos de pirazol como inibidores de jak |
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| AU2011328237A1 (en) | 2010-11-09 | 2013-05-23 | Cellzome Limited | Pyridine compounds and aza analogues thereof as TYK2 inhibitors |
-
2012
- 2012-12-20 CN CN201280070527.0A patent/CN104169272A/zh active Pending
- 2012-12-20 AU AU2012357038A patent/AU2012357038B2/en not_active Expired - Fee Related
- 2012-12-20 BR BR112014015723A patent/BR112014015723A8/pt not_active IP Right Cessation
- 2012-12-20 RU RU2014130214A patent/RU2014130214A/ru not_active Application Discontinuation
- 2012-12-20 KR KR1020147016971A patent/KR20140114344A/ko not_active Withdrawn
- 2012-12-20 JP JP2014548012A patent/JP2015500862A/ja not_active Withdrawn
- 2012-12-20 CA CA2860095A patent/CA2860095A1/en not_active Abandoned
- 2012-12-20 EP EP12806057.1A patent/EP2794598A1/en not_active Withdrawn
- 2012-12-20 US US14/367,958 patent/US20150005281A1/en not_active Abandoned
- 2012-12-20 WO PCT/EP2012/076371 patent/WO2013092854A1/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2641895C2 (ru) * | 2012-05-24 | 2018-01-23 | Целльзом Лимитид | ГЕТЕРОЦИКЛИЛЬНЫЕ ПИРИМИДИНОВЫЕ АНАЛОГИ В КАЧЕСТВЕ ИНГИБИТОРОВ Tук2 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015500862A (ja) | 2015-01-08 |
| CA2860095A1 (en) | 2013-06-27 |
| CN104169272A (zh) | 2014-11-26 |
| US20150005281A1 (en) | 2015-01-01 |
| KR20140114344A (ko) | 2014-09-26 |
| BR112014015723A8 (pt) | 2017-07-04 |
| EP2794598A1 (en) | 2014-10-29 |
| BR112014015723A2 (pt) | 2017-06-13 |
| AU2012357038A1 (en) | 2014-07-17 |
| AU2012357038B2 (en) | 2016-05-12 |
| WO2013092854A1 (en) | 2013-06-27 |
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