RU2478632C2 - Гидроксилированные и метоксилированные циклопента[d]пиримидины в качестве ингибиторов акт протеинкиназ - Google Patents
Гидроксилированные и метоксилированные циклопента[d]пиримидины в качестве ингибиторов акт протеинкиназ Download PDFInfo
- Publication number
- RU2478632C2 RU2478632C2 RU2009103900/04A RU2009103900A RU2478632C2 RU 2478632 C2 RU2478632 C2 RU 2478632C2 RU 2009103900/04 A RU2009103900/04 A RU 2009103900/04A RU 2009103900 A RU2009103900 A RU 2009103900A RU 2478632 C2 RU2478632 C2 RU 2478632C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- hydroxy
- cyclopenta
- dihydro
- piperazin
- Prior art date
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- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract 2
- 239000003909 protein kinase inhibitor Substances 0.000 title abstract 2
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 118
- 150000003839 salts Chemical class 0.000 claims abstract 24
- 239000012453 solvate Substances 0.000 claims abstract 8
- 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 claims abstract 6
- 206010028980 Neoplasm Diseases 0.000 claims abstract 4
- 201000011510 cancer Diseases 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- -1 CH 2 F Chemical compound 0.000 claims 123
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 28
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 20
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 14
- 125000004429 atom Chemical group 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000003386 piperidinyl group Chemical group 0.000 claims 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 239000001301 oxygen Substances 0.000 claims 10
- 239000011593 sulfur Substances 0.000 claims 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- 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 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 229910052740 iodine Inorganic materials 0.000 claims 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 4
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 4
- 125000006413 ring segment Chemical group 0.000 claims 4
- UVHCRURXEOGIOT-ZPMCFJSWSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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)NC1CCOCC1 UVHCRURXEOGIOT-ZPMCFJSWSA-N 0.000 claims 3
- GPXSIDKEQZLUST-SXSPYAJSSA-N (2s)-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(oxan-4-yl)amino]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)C1CCOCC1 GPXSIDKEQZLUST-SXSPYAJSSA-N 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- GRZXWCHAXNAUHY-NSISKUIASA-N (2S)-2-(4-chlorophenyl)-1-[4-[(5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl]-1-piperazinyl]-3-(propan-2-ylamino)-1-propanone Chemical compound C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Cl)C=C1 GRZXWCHAXNAUHY-NSISKUIASA-N 0.000 claims 2
- ZAPKSMBFGRLTBZ-QYRPDUKASA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-[[(3r)-oxolan-3-yl]amino]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]1CCOC1 ZAPKSMBFGRLTBZ-QYRPDUKASA-N 0.000 claims 2
- AQZUYEHYCSSTOS-QYRPDUKASA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-[[(3r)-pyrrolidin-3-yl]amino]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]1CCNC1 AQZUYEHYCSSTOS-QYRPDUKASA-N 0.000 claims 2
- AQZUYEHYCSSTOS-UMSONDCASA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-[[(3s)-pyrrolidin-3-yl]amino]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]1CCNC1 AQZUYEHYCSSTOS-UMSONDCASA-N 0.000 claims 2
- MGQHBEKIVYECCS-DUXKGJEZSA-N (2s)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CN(C)C(C)C)=CC=C(Cl)C=C1 MGQHBEKIVYECCS-DUXKGJEZSA-N 0.000 claims 2
- QGUOXJAMLQVZTF-CDHQVMDDSA-N (2s)-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 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(O)C1 QGUOXJAMLQVZTF-CDHQVMDDSA-N 0.000 claims 2
- DJKIPNZIOLJURK-MAODMQOUSA-N (2s)-2-(4-chlorophenyl)-3-(cyclopropylmethylamino)-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)NCC1CC1 DJKIPNZIOLJURK-MAODMQOUSA-N 0.000 claims 2
- XCEGMTIINVNYNX-ATZDWAIDSA-N (2s)-2-(4-chlorophenyl)-3-(dimethylamino)-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](CN(C)C)C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)=CC=C(Cl)C=C1 XCEGMTIINVNYNX-ATZDWAIDSA-N 0.000 claims 2
- RRYMJFIXVPYGON-WRWLIDTKSA-N (2s)-2-[4-chloro-3-(trifluoromethyl)phenyl]-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Cl)C(C(F)(F)F)=C1 RRYMJFIXVPYGON-WRWLIDTKSA-N 0.000 claims 2
- FKWGZLUCQAOQDJ-KBRIMQKVSA-N (2s)-3-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 C1([C@@H](CN)C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)=CC=C(Cl)C=C1 FKWGZLUCQAOQDJ-KBRIMQKVSA-N 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- AGKRBOABBMQFSL-SZVBFZGTSA-N (2r)-2-(5-bromopyridin-2-yl)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Br)C=N1 AGKRBOABBMQFSL-SZVBFZGTSA-N 0.000 claims 1
- PSFGVYMXTXICGR-ZPMCFJSWSA-N (2s)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)-2-[4-(trifluoromethyl)phenyl]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(=CC=1)C(F)(F)F)NC1CCOCC1 PSFGVYMXTXICGR-ZPMCFJSWSA-N 0.000 claims 1
- XPLGOANHGFSMIB-NSISKUIASA-N (2s)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)-2-[4-(trifluoromethoxy)phenyl]propan-1-one Chemical compound C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(OC(F)(F)F)C=C1 XPLGOANHGFSMIB-NSISKUIASA-N 0.000 claims 1
- TXWKFKHXOFXTKU-BRWVUGGUSA-N (2s)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)-2-thiophen-2-ylpropan-1-one Chemical compound C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=CS1 TXWKFKHXOFXTKU-BRWVUGGUSA-N 0.000 claims 1
- PSFGVYMXTXICGR-YHYVQYDKSA-N (2s)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)-2-[4-(trifluoromethyl)phenyl]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(=CC=1)C(F)(F)F)NC1CCOCC1 PSFGVYMXTXICGR-YHYVQYDKSA-N 0.000 claims 1
- RFVHSXAEGORYON-WRWLIDTKSA-N (2s)-2-(3,4-dichlorophenyl)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Cl)C(Cl)=C1 RFVHSXAEGORYON-WRWLIDTKSA-N 0.000 claims 1
- SWWHWGUJQDFXIK-CDHQVMDDSA-N (2s)-2-(3-chloro-5-fluorophenyl)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC(F)=CC(Cl)=C1 SWWHWGUJQDFXIK-CDHQVMDDSA-N 0.000 claims 1
- MUXRDILUGIICGM-YVWKXTFCSA-N (2s)-2-(3-fluoro-4-methoxyphenyl)-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 C1=C(F)C(OC)=CC=C1[C@@H](CNC(C)C)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 MUXRDILUGIICGM-YVWKXTFCSA-N 0.000 claims 1
- DFIROWVISDLYGD-BSLALVQMSA-N (2s)-2-(4-bromo-2-fluorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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(Br)=CC=1)F)NC1CCOCC1 DFIROWVISDLYGD-BSLALVQMSA-N 0.000 claims 1
- BZFDVHZRSWYZDK-XFQXTVEOSA-N (2s)-2-(4-bromo-2-fluorophenyl)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Br)C=C1F BZFDVHZRSWYZDK-XFQXTVEOSA-N 0.000 claims 1
- BZFDVHZRSWYZDK-ZTNFWEORSA-N (2s)-2-(4-bromo-2-fluorophenyl)-1-[4-[(5r,7s)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Br)C=C1F BZFDVHZRSWYZDK-ZTNFWEORSA-N 0.000 claims 1
- FTWBLDCYUPIIAY-VMRPVKRXSA-N (2s)-2-(4-bromo-2-fluorophenyl)-3-(cyclopropylmethylamino)-1-[4-[(5r,7s)-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(Br)=CC=1)F)NCC1CC1 FTWBLDCYUPIIAY-VMRPVKRXSA-N 0.000 claims 1
- OCQNQFLNELAMDZ-PERKRYKHSA-N (2s)-2-(4-bromo-3-fluorophenyl)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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(Br)=CC=1)NC1CCOCC1 OCQNQFLNELAMDZ-PERKRYKHSA-N 0.000 claims 1
- XVEXKPVULYSHJA-MDYRTPRTSA-N (2s)-2-(4-bromo-3-fluorophenyl)-1-[4-[(5r,7s)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Br)C(F)=C1 XVEXKPVULYSHJA-MDYRTPRTSA-N 0.000 claims 1
- HFGKNCISXBYAHW-FPDPHYFHSA-N (2s)-2-(4-bromo-3-fluorophenyl)-3-(cyclopropylmethylamino)-1-[4-[(5r,7s)-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=C(F)C(Br)=CC=1)NCC1CC1 HFGKNCISXBYAHW-FPDPHYFHSA-N 0.000 claims 1
- WVIZRBIXJGGNIL-ZPMCFJSWSA-N (2s)-2-(4-bromophenyl)-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=CC(Br)=CC=1)N1CCC(O)CC1 WVIZRBIXJGGNIL-ZPMCFJSWSA-N 0.000 claims 1
- FOQONSLSQMXHLK-AGILITTLSA-N (2s)-2-(4-bromophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(4-propan-2-ylpiperazin-1-yl)propan-1-one Chemical compound C1CN(C(C)C)CCN1C[C@H](C=1C=CC(Br)=CC=1)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 FOQONSLSQMXHLK-AGILITTLSA-N 0.000 claims 1
- SNDIBRJFLLYGDF-ZPMCFJSWSA-N (2s)-2-(4-bromophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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(Br)=CC=1)NC1CCOCC1 SNDIBRJFLLYGDF-ZPMCFJSWSA-N 0.000 claims 1
- PUPXZZLGFLTHDO-DUXKGJEZSA-N (2s)-2-(4-bromophenyl)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CN(C)C(C)C)=CC=C(Br)C=C1 PUPXZZLGFLTHDO-DUXKGJEZSA-N 0.000 claims 1
- SNDIBRJFLLYGDF-YHYVQYDKSA-N (2s)-2-(4-bromophenyl)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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(Br)=CC=1)NC1CCOCC1 SNDIBRJFLLYGDF-YHYVQYDKSA-N 0.000 claims 1
- GGGQLFZGNGYUKR-AHRSYUTCSA-N (2s)-2-(4-bromophenyl)-1-[4-[(5r,7s)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Br)C=C1 GGGQLFZGNGYUKR-AHRSYUTCSA-N 0.000 claims 1
- PUPXZZLGFLTHDO-UIFIKXQLSA-N (2s)-2-(4-bromophenyl)-1-[4-[(5r,7s)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@H](O)C=3N=CN=2)CN(C)C(C)C)=CC=C(Br)C=C1 PUPXZZLGFLTHDO-UIFIKXQLSA-N 0.000 claims 1
- WPELGIJMNKTPIX-HBGVWJBISA-N (2s)-2-(4-bromophenyl)-3-(cyclopropylmethylamino)-1-[4-[(5r,7s)-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(Br)=CC=1)NCC1CC1 WPELGIJMNKTPIX-HBGVWJBISA-N 0.000 claims 1
- HSOGRIPRDLRNDR-NSISKUIASA-N (2s)-2-(4-bromophenyl)-3-(tert-butylamino)-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](CNC(C)(C)C)C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)=CC=C(Br)C=C1 HSOGRIPRDLRNDR-NSISKUIASA-N 0.000 claims 1
- QKNAUPPDBNDABJ-OTDDCGGZSA-N (2s)-2-(4-bromophenyl)-3-[(3,3-dimethylcyclohexyl)amino]-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(Br)=CC=1)NC1CCCC(C)(C)C1 QKNAUPPDBNDABJ-OTDDCGGZSA-N 0.000 claims 1
- LXYGYMUEGJOHPL-CTUHWIOQSA-N (2s)-2-(4-bromophenyl)-3-[(4,4-dimethylcyclohexyl)amino]-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(Br)=CC=1)NC1CCC(C)(C)CC1 LXYGYMUEGJOHPL-CTUHWIOQSA-N 0.000 claims 1
- XWUHJIRBJMLAJN-YHYVQYDKSA-N (2s)-2-(4-bromophenyl)-3-[cyclopropylmethyl(methyl)amino]-1-[4-[(5r,7s)-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(Br)=CC=1)N(C)CC1CC1 XWUHJIRBJMLAJN-YHYVQYDKSA-N 0.000 claims 1
- ZTYJPNKNJIXMLC-BSLALVQMSA-N (2s)-2-(4-chloro-2-fluorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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)F)NC1CCOCC1 ZTYJPNKNJIXMLC-BSLALVQMSA-N 0.000 claims 1
- NCSAHEXYKZKHST-XFQXTVEOSA-N (2s)-2-(4-chloro-2-fluorophenyl)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Cl)C=C1F NCSAHEXYKZKHST-XFQXTVEOSA-N 0.000 claims 1
- ZTYJPNKNJIXMLC-CNDZOEFASA-N (2s)-2-(4-chloro-2-fluorophenyl)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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)F)NC1CCOCC1 ZTYJPNKNJIXMLC-CNDZOEFASA-N 0.000 claims 1
- SVXUNOUHNODYLE-QFIXIFRTSA-N (2s)-2-(4-chloro-2-fluorophenyl)-3-(cyclopropylmethylamino)-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)F)NCC1CC1 SVXUNOUHNODYLE-QFIXIFRTSA-N 0.000 claims 1
- VDABUDNQDPCQIC-HGHGUNKESA-N (2s)-2-(4-chloro-3-fluorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(2-methylpropylamino)propan-1-one Chemical compound C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNCC(C)C)=CC=C(Cl)C(F)=C1 VDABUDNQDPCQIC-HGHGUNKESA-N 0.000 claims 1
- PSNRYUGYGZTZSY-PERKRYKHSA-N (2s)-2-(4-chloro-3-fluorophenyl)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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(Cl)=CC=1)NC1CCOCC1 PSNRYUGYGZTZSY-PERKRYKHSA-N 0.000 claims 1
- YCWGOSQFOZHSQF-ZWDAVXSWSA-N (2s)-2-(4-chloro-3-fluorophenyl)-3-(cyclopentylamino)-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=C(F)C(Cl)=CC=1)NC1CCCC1 YCWGOSQFOZHSQF-ZWDAVXSWSA-N 0.000 claims 1
- DACYNDHEVFUCHW-STZQEDGTSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(1,4-oxazepan-4-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)N1CCCOCC1 DACYNDHEVFUCHW-STZQEDGTSA-N 0.000 claims 1
- BDKRQVSZTNVSIM-MAODMQOUSA-N (2s)-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)CN1C[C@H](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-MAODMQOUSA-N 0.000 claims 1
- MVKDZJLQKKHGGJ-ZPMCFJSWSA-N (2s)-2-(4-chlorophenyl)-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=CC(Cl)=CC=1)N1CCC(O)CC1 MVKDZJLQKKHGGJ-ZPMCFJSWSA-N 0.000 claims 1
- JKUFKXQNEFTSBQ-AGILITTLSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(4-propan-2-ylpiperazin-1-yl)propan-1-one Chemical compound C1CN(C(C)C)CCN1C[C@H](C=1C=CC(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 JKUFKXQNEFTSBQ-AGILITTLSA-N 0.000 claims 1
- OMFKFXBPXIIGLQ-ZTFGCOKTSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(methoxyamino)propan-1-one Chemical compound C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNOC)=CC=C(Cl)C=C1 OMFKFXBPXIIGLQ-ZTFGCOKTSA-N 0.000 claims 1
- AKFVQBJAJZYJNS-SXSPYAJSSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-[4-(methylamino)piperidin-1-yl]propan-1-one Chemical compound C1CC(NC)CCN1C[C@H](C=1C=CC(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 AKFVQBJAJZYJNS-SXSPYAJSSA-N 0.000 claims 1
- SEOVPDGEKCGNRW-DUXKGJEZSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-piperazin-1-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=CC(Cl)=CC=1)N1CCNCC1 SEOVPDGEKCGNRW-DUXKGJEZSA-N 0.000 claims 1
- VWFHPQXIADBYRU-DUXKGJEZSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-thiomorpholin-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=CC(Cl)=CC=1)N1CCSCC1 VWFHPQXIADBYRU-DUXKGJEZSA-N 0.000 claims 1
- XGQBOEHKQAUZEB-UEVCKROQSA-N (2s)-2-(4-chlorophenyl)-3-(4-ethylpiperazin-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 C1CN(CC)CCN1C[C@H](C=1C=CC(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 XGQBOEHKQAUZEB-UEVCKROQSA-N 0.000 claims 1
- DMFQEDIRMMWZOK-ZPMCFJSWSA-N (2s)-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 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(F)CC1 DMFQEDIRMMWZOK-ZPMCFJSWSA-N 0.000 claims 1
- SBBKNPLQAOQYBE-YSZBQJHXSA-N (2s)-2-(4-chlorophenyl)-3-(cyclohexylamino)-1-[4-[(5r,7s)-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)NC1CCCCC1 SBBKNPLQAOQYBE-YSZBQJHXSA-N 0.000 claims 1
- KMKLBXPCPBKGKR-CDHQVMDDSA-N (2s)-2-(4-chlorophenyl)-3-(cyclopropylamino)-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)NC1CC1 KMKLBXPCPBKGKR-CDHQVMDDSA-N 0.000 claims 1
- KGJFDXSJMOTVJN-OTDDCGGZSA-N (2s)-2-(4-chlorophenyl)-3-[(3,3-dimethylcyclohexyl)amino]-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)NC1CCCC(C)(C)C1 KGJFDXSJMOTVJN-OTDDCGGZSA-N 0.000 claims 1
- UKUKRSMZCFAQGY-YJSIEXFISA-N (2s)-2-(4-chlorophenyl)-3-[(3s)-3-(dimethylamino)pyrrolidin-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)N1CC[C@H](N(C)C)C1 UKUKRSMZCFAQGY-YJSIEXFISA-N 0.000 claims 1
- KEPZFCOIQOGOAI-CTUHWIOQSA-N (2s)-2-(4-chlorophenyl)-3-[(4,4-dimethylcyclohexyl)amino]-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)NC1CCC(C)(C)CC1 KEPZFCOIQOGOAI-CTUHWIOQSA-N 0.000 claims 1
- AWFVEFPXVJEZNV-STZQEDGTSA-N (2s)-2-(4-chlorophenyl)-3-[2-hydroxyethyl(propan-2-yl)amino]-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](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CN(CCO)C(C)C)=CC=C(Cl)C=C1 AWFVEFPXVJEZNV-STZQEDGTSA-N 0.000 claims 1
- LHESKSDGVWTWIF-CTUHWIOQSA-N (2s)-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-CTUHWIOQSA-N 0.000 claims 1
- CBPFHOOOOIINAJ-KBAYOESNSA-N (2s)-2-(5-bromothiophen-2-yl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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=1SC(Br)=CC=1)NC1CCOCC1 CBPFHOOOOIINAJ-KBAYOESNSA-N 0.000 claims 1
- NYYIKRNWSFCJDK-BZUAXINKSA-N (2s)-2-(5-bromothiophen-2-yl)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Br)S1 NYYIKRNWSFCJDK-BZUAXINKSA-N 0.000 claims 1
- CBPFHOOOOIINAJ-NXHRZFHOSA-N (2s)-2-(5-bromothiophen-2-yl)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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=1SC(Br)=CC=1)NC1CCOCC1 CBPFHOOOOIINAJ-NXHRZFHOSA-N 0.000 claims 1
- NYYIKRNWSFCJDK-OAGGEKHMSA-N (2s)-2-(5-bromothiophen-2-yl)-1-[4-[(5r,7s)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Br)S1 NYYIKRNWSFCJDK-OAGGEKHMSA-N 0.000 claims 1
- CQZBIBHQPCYHOO-DJIMGWMZSA-N (2s)-2-(5-bromothiophen-2-yl)-3-(cyclopropylmethylamino)-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=1SC(Br)=CC=1)NCC1CC1 CQZBIBHQPCYHOO-DJIMGWMZSA-N 0.000 claims 1
- GJGDNLJWWOESDA-KBAYOESNSA-N (2s)-2-(5-chlorothiophen-2-yl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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=1SC(Cl)=CC=1)NC1CCOCC1 GJGDNLJWWOESDA-KBAYOESNSA-N 0.000 claims 1
- BBXCLVDVJJVPOU-BZUAXINKSA-N (2s)-2-(5-chlorothiophen-2-yl)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Cl)S1 BBXCLVDVJJVPOU-BZUAXINKSA-N 0.000 claims 1
- GJGDNLJWWOESDA-NXHRZFHOSA-N (2s)-2-(5-chlorothiophen-2-yl)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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=1SC(Cl)=CC=1)NC1CCOCC1 GJGDNLJWWOESDA-NXHRZFHOSA-N 0.000 claims 1
- BBXCLVDVJJVPOU-OAGGEKHMSA-N (2s)-2-(5-chlorothiophen-2-yl)-1-[4-[(5r,7s)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Cl)S1 BBXCLVDVJJVPOU-OAGGEKHMSA-N 0.000 claims 1
- HYAZYJQOAUYZSW-DJIMGWMZSA-N (2s)-2-(5-chlorothiophen-2-yl)-3-(cyclopropylmethylamino)-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=1SC(Cl)=CC=1)NCC1CC1 HYAZYJQOAUYZSW-DJIMGWMZSA-N 0.000 claims 1
- HYAZYJQOAUYZSW-OIISXLGYSA-N (2s)-2-(5-chlorothiophen-2-yl)-3-(cyclopropylmethylamino)-1-[4-[(5r,7s)-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=1SC(Cl)=CC=1)NCC1CC1 HYAZYJQOAUYZSW-OIISXLGYSA-N 0.000 claims 1
- NOLUQBGMNDMEJW-XFQXTVEOSA-N (2s)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(C(F)(F)F)C=C1F NOLUQBGMNDMEJW-XFQXTVEOSA-N 0.000 claims 1
- XWVOYCYKVHDZAO-OZOXKJRCSA-N (2s)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CN(C)C(C)C)=CC=C(C(F)(F)F)C=C1F XWVOYCYKVHDZAO-OZOXKJRCSA-N 0.000 claims 1
- PVPUTMAIINVYHH-CNDZOEFASA-N (2s)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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(=CC=1)C(F)(F)F)F)NC1CCOCC1 PVPUTMAIINVYHH-CNDZOEFASA-N 0.000 claims 1
- NOLUQBGMNDMEJW-ZTNFWEORSA-N (2s)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-1-[4-[(5r,7s)-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@H](O)C=3N=CN=2)CNC(C)C)=CC=C(C(F)(F)F)C=C1F NOLUQBGMNDMEJW-ZTNFWEORSA-N 0.000 claims 1
- BHIAOYWMILQADT-SZVBFZGTSA-N (2s)-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-(propan-2-ylamino)propan-1-one Chemical compound C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(OC(F)(F)F)C(F)=C1 BHIAOYWMILQADT-SZVBFZGTSA-N 0.000 claims 1
- ZZPRCGSANDNMBX-BSIFCXSSSA-N (2s)-2-[3-fluoro-4-(trifluoromethoxy)phenyl]-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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)NC1CCOCC1 ZZPRCGSANDNMBX-BSIFCXSSSA-N 0.000 claims 1
- XMGQFGHGCVFDFK-ZWDAVXSWSA-N (2s)-2-[3-fluoro-4-(trifluoromethyl)phenyl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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(=CC=1)C(F)(F)F)NC1CCOCC1 XMGQFGHGCVFDFK-ZWDAVXSWSA-N 0.000 claims 1
- HPLLXKZTFYMEBR-WRWLIDTKSA-N (2s)-2-[3-fluoro-4-(trifluoromethyl)phenyl]-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(C(F)(F)F)C(F)=C1 HPLLXKZTFYMEBR-WRWLIDTKSA-N 0.000 claims 1
- XMGQFGHGCVFDFK-PERKRYKHSA-N (2s)-2-[3-fluoro-4-(trifluoromethyl)phenyl]-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-(oxan-4-ylamino)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(=CC=1)C(F)(F)F)NC1CCOCC1 XMGQFGHGCVFDFK-PERKRYKHSA-N 0.000 claims 1
- XCUWQXDXHIKEQH-SZVBFZGTSA-N (2s)-2-[4-chloro-3-(trifluoromethoxy)phenyl]-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(Cl)C(OC(F)(F)F)=C1 XCUWQXDXHIKEQH-SZVBFZGTSA-N 0.000 claims 1
- PXNRLWPGIVMVJJ-SZVBFZGTSA-N (2s)-2-[4-fluoro-3-(trifluoromethoxy)phenyl]-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(F)C(OC(F)(F)F)=C1 PXNRLWPGIVMVJJ-SZVBFZGTSA-N 0.000 claims 1
- KYSJQIIDJYBJQD-WRWLIDTKSA-N (2s)-2-[4-fluoro-3-(trifluoromethyl)phenyl]-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 C1([C@H](C(=O)N2CCN(CC2)C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CNC(C)C)=CC=C(F)C(C(F)(F)F)=C1 KYSJQIIDJYBJQD-WRWLIDTKSA-N 0.000 claims 1
- XQHJGSRNSFPVKJ-ZPMCFJSWSA-N (2s)-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-ZPMCFJSWSA-N 0.000 claims 1
- RRSHYJAMIPDULM-MAODMQOUSA-N (2s)-3-(cyclopropylmethylamino)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[4-(trifluoromethyl)phenyl]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(=CC=1)C(F)(F)F)NCC1CC1 RRSHYJAMIPDULM-MAODMQOUSA-N 0.000 claims 1
- RRSHYJAMIPDULM-HBGVWJBISA-N (2s)-3-(cyclopropylmethylamino)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[4-(trifluoromethyl)phenyl]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(=CC=1)C(F)(F)F)NCC1CC1 RRSHYJAMIPDULM-HBGVWJBISA-N 0.000 claims 1
- XGFQLCBCUUZIGA-QFIXIFRTSA-N (2s)-3-(cyclopropylmethylamino)-2-[2-fluoro-4-(trifluoromethyl)phenyl]-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(=CC=1)C(F)(F)F)F)NCC1CC1 XGFQLCBCUUZIGA-QFIXIFRTSA-N 0.000 claims 1
- ZLQWIDSPRZYJTH-ZTNFWEORSA-N (2s)-3-(cyclopropylmethylamino)-2-[3-fluoro-4-(trifluoromethoxy)phenyl]-1-[4-[(5r,7s)-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=C(F)C(OC(F)(F)F)=CC=1)NCC1CC1 ZLQWIDSPRZYJTH-ZTNFWEORSA-N 0.000 claims 1
- NRRILVLCPJUGCY-FPDPHYFHSA-N (2s)-3-(cyclopropylmethylamino)-2-[3-fluoro-4-(trifluoromethyl)phenyl]-1-[4-[(5r,7s)-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=C(F)C(=CC=1)C(F)(F)F)NCC1CC1 NRRILVLCPJUGCY-FPDPHYFHSA-N 0.000 claims 1
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- DYTNKKBQDCZIGM-DQMJNTIXSA-N (2s)-3-[(1-acetylpiperidin-4-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)NC1CCN(C(C)=O)CC1 DYTNKKBQDCZIGM-DQMJNTIXSA-N 0.000 claims 1
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- MOFXCWWIQFLBCN-MRRJBJDNSA-N (2s)-3-amino-2-(3,4-dichlorophenyl)-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C1([C@@H](CN)C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)=CC=C(Cl)C(Cl)=C1 MOFXCWWIQFLBCN-MRRJBJDNSA-N 0.000 claims 1
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Classifications
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
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| PCT/US2007/072885 WO2008006040A1 (en) | 2006-07-06 | 2007-07-05 | Hydroxylated and methoxylated cyclopenta [d] pyrimidines as akt protein kinase inhibitors |
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| RU2012155606/04A RU2012155606A (ru) | 2006-07-06 | 2012-12-20 | Гидроксилированные и метоксилированные циклопента[d]пиримидины в качестве ингибиторов акт протеинкиназ |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2643811C2 (ru) * | 2012-05-17 | 2018-02-06 | Аррэй Байофарма Инк. | Способ получения гидроксилированных циклопентилпиримидиновых соединений |
| RU2732404C2 (ru) * | 2014-09-26 | 2020-09-16 | Ф. Хоффманн-Ля Рош Аг | СПОСОБЫ ПОЛУЧЕНИЯ (ЦИКЛОПЕНТИЛ[d]ПИРИМИДИН-4-ИЛ)ПИПЕРАЗИНОВЫХ СОЕДИНЕНИЙ |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8329701B2 (en) | 2006-07-06 | 2012-12-11 | Array Biopharma Inc. | Dihydrofuro pyrimidines as AKT protein kinase inhibitors |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| 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 |
| CN103288753A (zh) | 2006-07-06 | 2013-09-11 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的环戊二烯并[d]嘧啶 |
| 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 |
| US20110135569A1 (en) | 2007-03-20 | 2011-06-09 | Peak Biosciences Inc. | Method for therapeutic administration of radionucleosides |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| KR101624361B1 (ko) | 2007-07-05 | 2016-05-25 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 억제제로서의 피리미딜 시클로펜탄 |
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| CA2692502C (en) | 2007-07-05 | 2016-03-01 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| EP2250155B1 (en) * | 2008-01-09 | 2013-07-03 | Array Biopharma, Inc. | 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors |
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| CN102015708B (zh) | 2008-01-09 | 2014-03-26 | 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 |
| ES2401685T3 (es) * | 2008-01-09 | 2013-04-23 | Array Biopharma, Inc. | Pirimidil ciclopentano hidroxilado como inhibidor de la proteína quinasa AKT |
| KR20130132956A (ko) * | 2010-12-23 | 2013-12-05 | 제넨테크, 인크. | 신생물의 치료를 위한 자식증 유도자 및 억제제 조합 요법 |
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| MY179607A (en) | 2011-04-01 | 2020-11-11 | Genentech Inc | Combinations of akt inhibitor compounds and abiraterone, and methods of use |
| JP6147246B2 (ja) | 2011-04-01 | 2017-06-14 | ジェネンテック， インコーポレイテッド | Ａｋｔ及びｍｅｋ阻害剤化合物の組み合わせ、及び使用方法 |
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| AU2013262521B2 (en) | 2012-05-17 | 2017-03-02 | Genentech, Inc. | Process of making hydroxylated cyclopentapyrimidine compounds and salts thereof |
| WO2014068070A1 (en) | 2012-10-31 | 2014-05-08 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for preventing antiphospholipid syndrome (aps) |
| JP2016502974A (ja) * | 2012-12-07 | 2016-02-01 | ザ ジェネラル ホスピタル コーポレイション | Ｐｉ３ｋ／ａｋｔ阻害剤化合物とｈｅｒ３／ｅｇｆｒ阻害剤化合物との組み合わせ及び高増殖性疾患の治療におけるその使用 |
| 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 |
| SG10201901578UA (en) | 2013-11-15 | 2019-03-28 | Hoffmann La Roche | Processes for the preparation of pyrimidinylcyclopentane compounds |
| EP3496722B1 (en) | 2016-08-10 | 2025-07-16 | F. Hoffmann-La Roche AG | Pharmaceutical compositions comprising akt protein kinase inhibitors |
| CA3041840A1 (en) | 2016-10-28 | 2018-05-03 | Icahn School Of Medicine At Mount Sinai | Compositions and methods for treating ezh2-mediated cancer |
| US11472799B2 (en) * | 2018-03-06 | 2022-10-18 | Icahn School Of Medicine At Mount Sinai | Serine threonine kinase (AKT) degradation / disruption compounds and methods of use |
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| US11701356B2 (en) | 2018-12-19 | 2023-07-18 | Genentech, Inc. | Treatment of breast cancer using combination therapies comprising an AKT inhibitor, a taxane, and a PD-L1 inhibitor |
| AU2019407426A1 (en) | 2018-12-21 | 2021-07-22 | Daiichi Sankyo Company, Limited | Combination of antibody-drug conjugate and kinase inhibitor |
| CN117964620A (zh) | 2019-01-29 | 2024-05-03 | 南京正大天晴制药有限公司 | Akt抑制剂 |
| US20220249511A1 (en) | 2019-03-29 | 2022-08-11 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the treatment of keloid, hypertrophic scars and/or hyperpigmentation disorders |
| JP7667742B2 (ja) * | 2019-04-09 | 2025-04-23 | ダナ－ファーバー キャンサー インスティテュート，インコーポレイテッド | Ａｔｐ競合性ａｋｔ阻害剤ｇｄｃ－００６８とｅ３リガーゼリガンドとの結合によるａｋｔの分解および使用方法 |
| CA3167999A1 (en) * | 2020-03-17 | 2021-09-23 | Xin Li | Fused bicyclic derivative, preparation method therefor, 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 |
| WO2021254920A1 (en) | 2020-06-16 | 2021-12-23 | F. Hoffmann-La Roche Ag | Process for making hydroxylated cyclopentylpyrimidine compounds |
| WO2022017449A1 (zh) | 2020-07-22 | 2022-01-27 | 南京正大天晴制药有限公司 | 一种二氢吡啶并[2,3-d]嘧啶酮衍生物的盐、其制备方法及用途 |
| 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 |
| JP2025510910A (ja) | 2022-03-31 | 2025-04-15 | アストラゼネカ・アクチエボラーグ | 癌の処置のための、ａｋｔ阻害剤との組み合わせにおける上皮成長因子受容体（ｅｇｆｒ）チロシンキナーゼ阻害剤 |
| 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 |
| CN120712346A (zh) | 2023-01-31 | 2025-09-26 | 豪夫迈·罗氏有限公司 | 具有增加的酮还原酶活性的突变型酮还原酶以及涉及其的方法和用途 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005051304A2 (en) * | 2003-11-21 | 2005-06-09 | Array Biopharma Inc. | Akt protein kinase inhibitors |
| EA005809B1 (ru) * | 2000-08-18 | 2005-06-30 | Милленниум Фармасьютикалз, Инк. | Производные хиназолина в качестве ингибиторов киназы |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| NL7112938A (instruction) * | 1970-09-30 | 1972-04-05 | ||
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| JP3297058B2 (ja) * | 1997-01-08 | 2002-07-02 | エフ．ホフマン−ラ ロシュ アーゲー | 三環式ベンゾ［ｅ］イソインドール及びベンゾ［ｈ］イソキノリン |
| ES2152902B1 (es) * | 1999-07-27 | 2001-08-16 | Medichem Sa | Procedimiento de obtencion de venlafaxina |
| AU2001290914A1 (en) * | 2000-09-15 | 2002-03-26 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| ES2365905T3 (es) * | 2001-03-30 | 2011-10-13 | King Pharmaceuticals, Inc. | Compuestos de tiofeno condensados y uso de los mismos en el tratamiento del dolor crónico. |
| ATE424388T1 (de) * | 2001-12-06 | 2009-03-15 | Merck & Co Inc | Mitotische kinesinhemmer |
| MXPA04007191A (es) * | 2002-01-23 | 2005-03-31 | Bayer Pharmaceuticals Corp | Derivados de pirimidina como inhibidores de rho-quinasa. |
| TW200306819A (en) * | 2002-01-25 | 2003-12-01 | Vertex Pharma | Indazole compounds useful as protein kinase inhibitors |
| EP1751133B1 (en) * | 2004-04-28 | 2010-04-14 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of rock and other protein kinases |
| WO2005113762A1 (en) | 2004-05-18 | 2005-12-01 | Pfizer Products Inc. | CRYSTAL STRUCTURE OF PROTEIN KINASE B-α (AKT-1) AND USES THEREOF |
| EP1866822A4 (en) * | 2005-03-03 | 2010-09-01 | Burnham Inst Medical Research | SCREENING PROCEDURE FOR PROTEIN KINASE B INHIBITORS USING VIRTUAL DOCKING APPARATUS AND COMPOSITIONS AND COMPOSITIONS DISCOVERED THEREFOR |
| 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 |
| CN103288753A (zh) * | 2006-07-06 | 2013-09-11 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的环戊二烯并[d]嘧啶 |
| 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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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA005809B1 (ru) * | 2000-08-18 | 2005-06-30 | Милленниум Фармасьютикалз, Инк. | Производные хиназолина в качестве ингибиторов киназы |
| WO2005051304A2 (en) * | 2003-11-21 | 2005-06-09 | Array Biopharma Inc. | Akt protein kinase inhibitors |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2643811C2 (ru) * | 2012-05-17 | 2018-02-06 | Аррэй Байофарма Инк. | Способ получения гидроксилированных циклопентилпиримидиновых соединений |
| RU2732404C2 (ru) * | 2014-09-26 | 2020-09-16 | Ф. Хоффманн-Ля Рош Аг | СПОСОБЫ ПОЛУЧЕНИЯ (ЦИКЛОПЕНТИЛ[d]ПИРИМИДИН-4-ИЛ)ПИПЕРАЗИНОВЫХ СОЕДИНЕНИЙ |
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