ES2554228T3 - Ciclopenta[d]pirimidinas hidroxiladas como inhibidores de la proteína quinasa AKT - Google Patents
Ciclopenta[d]pirimidinas hidroxiladas como inhibidores de la proteína quinasa AKT Download PDFInfo
- Publication number
- ES2554228T3 ES2554228T3 ES11166123.7T ES11166123T ES2554228T3 ES 2554228 T3 ES2554228 T3 ES 2554228T3 ES 11166123 T ES11166123 T ES 11166123T ES 2554228 T3 ES2554228 T3 ES 2554228T3
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- ES
- Spain
- Prior art keywords
- piperazin
- pyrimidin
- dihydro
- cyclopenta
- hydroxy
- 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.)
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- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
- 239000003909 protein kinase inhibitor Substances 0.000 title 1
- 150000003230 pyrimidines Chemical class 0.000 title 1
- -1 tetrahydrofuranoyl Chemical group 0.000 abstract description 194
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 6
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000003566 oxetanyl group Chemical group 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 105
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 71
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 55
- 238000005160 1H NMR spectroscopy Methods 0.000 description 53
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 25
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 11
- PVBCJJRNVMOSDK-IYSWYEEDSA-N (5R,7R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol Chemical compound O[C@@H]1C[C@H](C2=C1N=CN=C2)C PVBCJJRNVMOSDK-IYSWYEEDSA-N 0.000 description 9
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- PVBCJJRNVMOSDK-VDTYLAMSSA-N (5R,7S)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol Chemical compound O[C@H]1C[C@H](C2=C1N=CN=C2)C PVBCJJRNVMOSDK-VDTYLAMSSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- PVBCJJRNVMOSDK-NQPNHJOESA-N (7R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol Chemical compound CC1C[C@H](C2=NC=NC=C12)O PVBCJJRNVMOSDK-NQPNHJOESA-N 0.000 description 3
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- OXJYPGIKGXXPBP-AGILITTLSA-N (2r)-2-(4-bromophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-4-(3-imidazol-1-ylpropylamino)butan-1-one Chemical compound C([C@@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Br)=CC=1)CNCCCN1C=CN=C1 OXJYPGIKGXXPBP-AGILITTLSA-N 0.000 description 1
- KKDVAQZROSQFIO-OKRPEKNWSA-N (2r)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-4-[(2-hydroxy-1-phenylethyl)amino]butan-1-one Chemical compound C([C@@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Cl)=CC=1)CNC(CO)C1=CC=CC=C1 KKDVAQZROSQFIO-OKRPEKNWSA-N 0.000 description 1
- VEXSHJGNGILRJI-ILCQWTCRSA-N (2r)-2-(4-chlorophenyl)-3-[(2s,6r)-2,6-dimethylmorpholin-4-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Cl)=CC=1)N1C[C@H](C)O[C@H](C)C1 VEXSHJGNGILRJI-ILCQWTCRSA-N 0.000 description 1
- LHESKSDGVWTWIF-VEXUSMLFSA-N (2r)-2-(4-chlorophenyl)-3-[4-(dimethylamino)piperidin-1-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Cl)=CC=1)N1CCC(N(C)C)CC1 LHESKSDGVWTWIF-VEXUSMLFSA-N 0.000 description 1
- KBAMXFJMRDMARS-DQMJNTIXSA-N (2r)-2-[(1-acetylpiperidin-4-yl)amino]-3-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)NC1CCN(CC1)C(C)=O)C1=CC=C(Cl)C=C1 KBAMXFJMRDMARS-DQMJNTIXSA-N 0.000 description 1
- AZINUGHITMTEKR-LKUPVBHCSA-N (2r)-2-[3-fluoro-4-(trifluoromethoxy)phenyl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(4-hydroxypiperidin-1-yl)propan-1-one Chemical compound C([C@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=C(F)C(OC(F)(F)F)=CC=1)N1CCC(O)CC1 AZINUGHITMTEKR-LKUPVBHCSA-N 0.000 description 1
- GROLACOOUFTTBG-IMFGXOCKSA-N (2r)-2-[3-fluoro-4-(trifluoromethoxy)phenyl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-morpholin-4-ylpropan-1-one Chemical compound C([C@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=C(F)C(OC(F)(F)F)=CC=1)N1CCOCC1 GROLACOOUFTTBG-IMFGXOCKSA-N 0.000 description 1
- IWEOQEISAWDING-KBRIMQKVSA-N (2r)-2-amino-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(4-iodophenyl)propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C1=CC=C(I)C=C1 IWEOQEISAWDING-KBRIMQKVSA-N 0.000 description 1
- NZWOHIMDSZEHGF-KBRIMQKVSA-N (2r)-2-amino-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-[4-(trifluoromethyl)phenyl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C1=CC=C(C(F)(F)F)C=C1 NZWOHIMDSZEHGF-KBRIMQKVSA-N 0.000 description 1
- WXBZEODTEQDLCC-UIAACRFSSA-N (2r)-3-(3-aminoazetidin-1-yl)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Cl)=CC=1)N1CC(N)C1 WXBZEODTEQDLCC-UIAACRFSSA-N 0.000 description 1
- NLJZHCYNUJUZLQ-YFXJRYMSSA-N (2r)-3-(4-acetylpiperazin-1-yl)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Cl)=CC=1)N1CCN(C(C)=O)CC1 NLJZHCYNUJUZLQ-YFXJRYMSSA-N 0.000 description 1
- XQHJGSRNSFPVKJ-VOQZNFBZSA-N (2r)-3-(4-aminopiperidin-1-yl)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Cl)=CC=1)N1CCC(N)CC1 XQHJGSRNSFPVKJ-VOQZNFBZSA-N 0.000 description 1
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- WYOQJYFZPBGFBZ-ULLYJBBUSA-N (2s)-3-[[(3r)-1-acetylpyrrolidin-3-yl]amino]-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Cl)=CC=1)N[C@@H]1CCN(C(C)=O)C1 WYOQJYFZPBGFBZ-ULLYJBBUSA-N 0.000 description 1
- WYOQJYFZPBGFBZ-FJTGNWTPSA-N (2s)-3-[[(3s)-1-acetylpyrrolidin-3-yl]amino]-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](C(=O)N1CCN(CC1)C=1N=CN=C2[C@H](O)C[C@H](C=12)C)C=1C=CC(Cl)=CC=1)N[C@H]1CCN(C(C)=O)C1 WYOQJYFZPBGFBZ-FJTGNWTPSA-N 0.000 description 1
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- OWLDVUBHSFAGQJ-RKDXNWHRSA-N (5r,7r)-5-methyl-4-piperazin-1-yl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-7-ol Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N1CCNCC1 OWLDVUBHSFAGQJ-RKDXNWHRSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RIIRBWCELNIZOI-UHFFFAOYSA-N 1-(4-hydroxypiperidin-1-yl)propan-1-one Chemical compound CCC(=O)N1CCC(O)CC1 RIIRBWCELNIZOI-UHFFFAOYSA-N 0.000 description 1
- NPJDLBXOYGKXRN-UHFFFAOYSA-N 1-(4-methoxypiperidin-1-yl)propan-1-one Chemical compound CCC(=O)N1CCC(OC)CC1 NPJDLBXOYGKXRN-UHFFFAOYSA-N 0.000 description 1
- XRJADPSNZCNPAD-UHFFFAOYSA-N 1-(4-propan-2-ylpiperazin-1-yl)propan-1-one Chemical compound CCC(=O)N1CCN(C(C)C)CC1 XRJADPSNZCNPAD-UHFFFAOYSA-N 0.000 description 1
- YEQAMPOYHLICPF-UHFFFAOYSA-N 1-piperazin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCNCC1 YEQAMPOYHLICPF-UHFFFAOYSA-N 0.000 description 1
- GGGQLFZGNGYUKR-ZNCRQWOUSA-N 2-(4-bromophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C1CN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(Br)C=C1 GGGQLFZGNGYUKR-ZNCRQWOUSA-N 0.000 description 1
- BDKRQVSZTNVSIM-PMYDAVCKSA-N 2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(3-methoxyazetidin-1-yl)propan-1-one Chemical compound C1C(OC)CN1CC(C=1C=CC(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 BDKRQVSZTNVSIM-PMYDAVCKSA-N 0.000 description 1
- MGQHBEKIVYECCS-UBCDJDFNSA-N 2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-[methyl(propan-2-yl)amino]propan-1-one Chemical compound C1CN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CCN1C(=O)C(CN(C)C(C)C)C1=CC=C(Cl)C=C1 MGQHBEKIVYECCS-UBCDJDFNSA-N 0.000 description 1
- MDVCJJCABHQSMG-UBCDJDFNSA-N 2-(4-chlorophenyl)-3-(2,2-dimethylpropylamino)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(CC1)CCN1C(=O)C(CNCC(C)(C)C)C1=CC=C(Cl)C=C1 MDVCJJCABHQSMG-UBCDJDFNSA-N 0.000 description 1
- GAIAZMBAFPYBJL-ZNCRQWOUSA-N 2-(4-chlorophenyl)-3-(3,3-difluoropyrrolidin-1-yl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CCC(F)(F)C1 GAIAZMBAFPYBJL-ZNCRQWOUSA-N 0.000 description 1
- QGUOXJAMLQVZTF-CSKFVBRQSA-N 2-(4-chlorophenyl)-3-(3-hydroxyazetidin-1-yl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CC(O)C1 QGUOXJAMLQVZTF-CSKFVBRQSA-N 0.000 description 1
- WLCCBAFZTRJPTN-UBCDJDFNSA-N 2-(4-chlorophenyl)-3-(4,4-difluoropiperidin-1-yl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CCC(F)(F)CC1 WLCCBAFZTRJPTN-UBCDJDFNSA-N 0.000 description 1
- DMFQEDIRMMWZOK-PNWAUMQTSA-N 2-(4-chlorophenyl)-3-(4-fluoropiperidin-1-yl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CCC(F)CC1 DMFQEDIRMMWZOK-PNWAUMQTSA-N 0.000 description 1
- GUIKFXNYDIOZDA-XHMZRDMFSA-N 2-(4-chlorophenyl)-3-[(3r)-3-fluoropyrrolidin-1-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CC[C@@H](F)C1 GUIKFXNYDIOZDA-XHMZRDMFSA-N 0.000 description 1
- GUIKFXNYDIOZDA-XBBZPSQXSA-N 2-(4-chlorophenyl)-3-[(3s)-3-fluoropyrrolidin-1-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1([C@H](O)C[C@H](C=21)C)=NC=NC=2N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CC[C@H](F)C1 GUIKFXNYDIOZDA-XBBZPSQXSA-N 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- KTHVGTCZPUAGIC-UBCDJDFNSA-N 4-[1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-1-oxo-3-(propan-2-ylamino)propan-2-yl]benzonitrile Chemical compound C1CN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(C#N)C=C1 KTHVGTCZPUAGIC-UBCDJDFNSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- FHHLXBNYYYCVNB-UHFFFAOYSA-N CC(C)NC(=O)C(C)c1cccs1 Chemical compound CC(C)NC(=O)C(C)c1cccs1 FHHLXBNYYYCVNB-UHFFFAOYSA-N 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- BDVHVHJDMDYWPR-UHFFFAOYSA-N n,2,3-trimethylbutanamide Chemical compound CNC(=O)C(C)C(C)C BDVHVHJDMDYWPR-UHFFFAOYSA-N 0.000 description 1
- FJGJWYRWPDCSLR-UHFFFAOYSA-N n-(oxan-4-yl)butanamide Chemical compound CCCC(=O)NC1CCOCC1 FJGJWYRWPDCSLR-UHFFFAOYSA-N 0.000 description 1
- FUNWARJNYBEYBG-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropanamide Chemical compound CCC(=O)N(C)C(C)C FUNWARJNYBEYBG-UHFFFAOYSA-N 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UFWDDENALBDFOJ-UHFFFAOYSA-N tert-butyl N-(3-oxopropyl)-N-propan-2-ylcarbamate Chemical compound CC(C)N(CCC=O)C(=O)OC(C)(C)C UFWDDENALBDFOJ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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| ES11166125.2T Active ES2554252T3 (es) | 2006-07-06 | 2007-07-05 | Ciclopenta[d]pirimidinas hidroxiladas como inhibidores de la proteína quinasa AKT |
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| CN101516891B (zh) * | 2006-07-06 | 2013-06-05 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的二氢噻吩并嘧啶 |
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| DE602007011628D1 (de) * | 2006-07-06 | 2011-02-10 | Array Biopharma Inc | Dihydrofuropyrimidine als akt-proteinkinaseinhibitoren |
| ES2372955T3 (es) | 2006-07-06 | 2012-01-30 | Array Biopharma, Inc. | Ciclopenta[d]pirimidinas como inhibidores de la proteína cinasa akt. |
| UA95641C2 (xx) * | 2006-07-06 | 2011-08-25 | Эррей Биофарма Инк. | Гідроксильовані піримідильні циклопентани як інгібітори акт протеїнкінази$гидроксилированные пиримидильные циклопентаны как ингибиторы акт протеинкиназы |
| WO2008115511A1 (en) | 2007-03-20 | 2008-09-25 | Peak Biosciences, Inc. | Method for therapeutic administration of radionucleosides |
| CN101801955B (zh) | 2007-07-05 | 2013-05-08 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的嘧啶基环戊烷 |
| CA2692506C (en) | 2007-07-05 | 2015-11-24 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| EP2247578B1 (en) * | 2008-01-09 | 2013-05-22 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
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| MX2010007546A (es) | 2008-01-09 | 2010-09-30 | Array Biopharma Inc | Pirimidil ciclopentanos hidroxilados en forma de inhibidores de akt proteína quinasa. |
| RU2013134359A (ru) * | 2010-12-23 | 2015-01-27 | Дженентек, Инк. | Комбинированная терапия с применением индуктора и ингибитора аутофагии для лечения новообразований |
| KR102016182B1 (ko) * | 2011-04-01 | 2019-08-29 | 제넨테크, 인크. | 암 치료에 대한 감수성을 예측하기 위한 바이오마커 |
| US9682082B2 (en) | 2011-04-01 | 2017-06-20 | Genentech, Inc. | Combinations of AKT and MEK inhibitor compounds, and methods of use |
| CN112915092A (zh) * | 2011-04-01 | 2021-06-08 | 基因泰克公司 | Akt抑制剂化合物和阿比特龙的组合及使用方法 |
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| RU2015127037A (ru) * | 2012-12-07 | 2017-01-11 | Дзе Дженерал Хоспитал Корпорейшн | Комбинации ингибитора pi3k/akt с ингибитором her3/egfr и способы их применения |
| JP6340162B2 (ja) * | 2012-12-20 | 2018-06-06 | 日東電工株式会社 | アポトーシス誘導剤 |
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| KR102569636B1 (ko) | 2016-08-10 | 2023-08-23 | 에프. 호프만-라 로슈 아게 | Akt 단백질 키나아제 저해제를 포함하는 약학 조성물 |
| KR20190084063A (ko) | 2016-10-28 | 2019-07-15 | 이칸 스쿨 오브 메디슨 엣 마운트 시나이 | Ｅｚｈ２-매개성 암 치료용 조성물 및 방법 |
| AU2019231689A1 (en) * | 2018-03-06 | 2020-09-24 | Icahn School Of Medicine At Mount Sinai | Serine threonine kinase (AKT) degradation / disruption compounds and methods of use |
| CA3104298A1 (en) | 2018-06-21 | 2019-12-26 | Icahn School Of Medicine At Mount Sinai | Wd40 repeat domain protein 5 (wdr5) degradation / disruption compounds and methods of use |
| JP2022515371A (ja) | 2018-12-19 | 2022-02-18 | ジェネンテック， インコーポレイテッド | Ａｋｔ阻害剤、タキサンおよびｐｄ－ｌ１阻害剤を含む併用療法を用いた乳癌の処置 |
| EP3903828A4 (en) | 2018-12-21 | 2022-10-05 | Daiichi Sankyo Company, Limited | ANTIBODY-DRUG CONJUGATE AND KINAS INHIBITOR COMBINATION |
| EP3919491B1 (en) | 2019-01-29 | 2025-05-28 | Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. | Akt inhibitor |
| EP3946330A1 (en) | 2019-03-29 | 2022-02-09 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Methods for the treatment of keloid, hypertrophic scars and/or hyperpigmentation disorders |
| AU2020270908B2 (en) * | 2019-04-09 | 2025-09-25 | Beth Israel Deaconess Medical Center, Inc. | Degradation of AKT by conjugation of ATP-competitive AKT inhibitor GDC-0068 with E3 ligase ligands and methods of use |
| EP4122922A4 (en) * | 2020-03-17 | 2023-08-23 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | CONDENSED BICYCLIC DERIVATIVE, METHOD OF MANUFACTURE THEREOF AND PHARMACEUTICAL USE THEREOF |
| US12103924B2 (en) | 2020-06-01 | 2024-10-01 | Icahn School Of Medicine At Mount Sinai | Mitogen-activated protein kinase kinase (MEK) degradation compounds and methods of use |
| EP4165026A1 (en) | 2020-06-16 | 2023-04-19 | F. Hoffmann-La Roche AG | Process for making hydroxylated cyclopentylpyrimidine compounds |
| US20230286979A1 (en) | 2020-07-22 | 2023-09-14 | Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. | Salt of dihydropyrido[2,3-d]pyrimidinone derivative, preparation method therefor, and use thereof |
| TWI750905B (zh) * | 2020-11-19 | 2021-12-21 | 財團法人國家衛生研究院 | 噻唑化合物作為蛋白質激酶抑制劑 |
| KR102689151B1 (ko) * | 2021-09-06 | 2024-07-29 | 연세대학교 산학협력단 | Akt 신호경로 억제제를 유효성분으로 포함하는 아토피피부염의 예방 또는 치료용 조성물 |
| WO2023043869A1 (en) * | 2021-09-15 | 2023-03-23 | Teva Pharmaceuticals International Gmbh | Solid state forms of ipatasertib citrate |
| CN113788834B (zh) * | 2021-09-18 | 2022-11-29 | 河南奥思恩医药科技有限公司 | 2,4-二氯-6,7-二氢-5H-吡咯并[3,4-d]嘧啶盐酸盐的制备方法 |
| WO2023109540A1 (zh) * | 2021-12-17 | 2023-06-22 | 中国医药研究开发中心有限公司 | 具有akt激酶抑制活性的杂环化合物及其制备方法和医药用途 |
| WO2023187037A1 (en) | 2022-03-31 | 2023-10-05 | Astrazeneca Ab | Epidermal growth factor receptor (egfr) tyrosine kinase inhibitors in combination with an akt inhibitor for the treatment of cancer |
| AU2023362285A1 (en) | 2022-10-17 | 2025-05-29 | Astrazeneca Ab | Combinations of a serd for the treatment of cancer |
| WO2024100236A1 (en) | 2022-11-11 | 2024-05-16 | Astrazeneca Ab | Combination therapies for the treatment of cancer |
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| UA95641C2 (xx) * | 2006-07-06 | 2011-08-25 | Эррей Биофарма Инк. | Гідроксильовані піримідильні циклопентани як інгібітори акт протеїнкінази$гидроксилированные пиримидильные циклопентаны как ингибиторы акт протеинкиназы |
| CN101516891B (zh) * | 2006-07-06 | 2013-06-05 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的二氢噻吩并嘧啶 |
| ES2372955T3 (es) * | 2006-07-06 | 2012-01-30 | Array Biopharma, Inc. | Ciclopenta[d]pirimidinas como inhibidores de la proteína cinasa akt. |
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