HRP20110908T1 - Hidroksilirani i metoksilirani ciklopenta [d] pirimidini kao inhibitori kinaze akt proteina - Google Patents
Hidroksilirani i metoksilirani ciklopenta [d] pirimidini kao inhibitori kinaze akt proteina Download PDFInfo
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- HRP20110908T1 HRP20110908T1 HR20110908T HRP20110908T HRP20110908T1 HR P20110908 T1 HRP20110908 T1 HR P20110908T1 HR 20110908 T HR20110908 T HR 20110908T HR P20110908 T HRP20110908 T HR P20110908T HR P20110908 T1 HRP20110908 T1 HR P20110908T1
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- Croatia
- Prior art keywords
- methyl
- piperazin
- hydroxy
- cyclopenta
- dihydro
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- LTFBFZBWUKWXID-UHFFFAOYSA-N 1h-cyclopenta[d]pyrimidine Chemical class N1=CNC2=CC=CC2=C1 LTFBFZBWUKWXID-UHFFFAOYSA-N 0.000 title 1
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title 1
- 239000003909 protein kinase inhibitor Substances 0.000 title 1
- -1 C1-C6-alkyl Chemical group 0.000 claims abstract 34
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract 5
- 125000005843 halogen group Chemical group 0.000 claims abstract 5
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 4
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 4
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 3
- 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 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims abstract 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims abstract 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims abstract 2
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract 2
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 14
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 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
- 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 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
- 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 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
- UVHCRURXEOGIOT-YHYVQYDKSA-N (2s)-2-(4-chlorophenyl)-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)NC1CCOCC1 UVHCRURXEOGIOT-YHYVQYDKSA-N 0.000 claims 2
- GPXSIDKEQZLUST-YSZBQJHXSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7s)-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-YSZBQJHXSA-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
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 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 2
- ISTGFHMOXNIXNZ-GTCCEBARSA-N (2r)-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-(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(Cl)C(Cl)=CC=1)N1CCC(O)CC1 ISTGFHMOXNIXNZ-GTCCEBARSA-N 0.000 claims 1
- RBYYDKZLYVHVME-GTCCEBARSA-N (2r)-2-(4-bromo-3-fluorophenyl)-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(Br)=CC=1)N1CCC(O)CC1 RBYYDKZLYVHVME-GTCCEBARSA-N 0.000 claims 1
- NCSAHEXYKZKHST-MOXGXCLJSA-N (2r)-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-MOXGXCLJSA-N 0.000 claims 1
- ASIBYZZEGYJDKR-ZWCUEREDSA-N (2r)-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-(4-methylpiperazin-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)N1CCN(C)CC1 ASIBYZZEGYJDKR-ZWCUEREDSA-N 0.000 claims 1
- QGNYHPZDWVMHJH-PLMTUMEDSA-N (2r)-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-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(Cl)=CC=1)N1CCOCC1 QGNYHPZDWVMHJH-PLMTUMEDSA-N 0.000 claims 1
- DACYNDHEVFUCHW-BVYCBKJFSA-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]-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-BVYCBKJFSA-N 0.000 claims 1
- BDKRQVSZTNVSIM-TYCQWZJGSA-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]-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-TYCQWZJGSA-N 0.000 claims 1
- MVKDZJLQKKHGGJ-VOQZNFBZSA-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]-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-VOQZNFBZSA-N 0.000 claims 1
- NHOOVUOOHFQRHO-YFXJRYMSSA-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]-3-(4-methoxypiperidin-1-yl)propan-1-one Chemical compound C1CC(OC)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 NHOOVUOOHFQRHO-YFXJRYMSSA-N 0.000 claims 1
- OBYJRNHAFUOFQQ-BVYCBKJFSA-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]-3-(4-methylpiperazin-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)CC1 OBYJRNHAFUOFQQ-BVYCBKJFSA-N 0.000 claims 1
- RFBSNQAGNGBTPW-BVYCBKJFSA-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]-3-(4-methylsulfonylpiperazin-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(S(C)(=O)=O)CC1 RFBSNQAGNGBTPW-BVYCBKJFSA-N 0.000 claims 1
- JKUFKXQNEFTSBQ-FGCOXFRFSA-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]-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-FGCOXFRFSA-N 0.000 claims 1
- GRZXWCHAXNAUHY-LSTHTHJFSA-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]-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=C1 GRZXWCHAXNAUHY-LSTHTHJFSA-N 0.000 claims 1
- OYPIQVBFWWVKTL-RZXSNQJFSA-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]-3-[(3r)-3-hydroxypyrrolidin-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](O)C1 OYPIQVBFWWVKTL-RZXSNQJFSA-N 0.000 claims 1
- AKFVQBJAJZYJNS-YFXJRYMSSA-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]-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-YFXJRYMSSA-N 0.000 claims 1
- QIURAHCFIXKZFL-JRGCBEDISA-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]-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=CC(Cl)=CC=1)N1CCOCC1 QIURAHCFIXKZFL-JRGCBEDISA-N 0.000 claims 1
- SEOVPDGEKCGNRW-JRGCBEDISA-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]-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-JRGCBEDISA-N 0.000 claims 1
- VWFHPQXIADBYRU-JRGCBEDISA-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]-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-JRGCBEDISA-N 0.000 claims 1
- QGUOXJAMLQVZTF-UIAACRFSSA-N (2r)-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-UIAACRFSSA-N 0.000 claims 1
- XGQBOEHKQAUZEB-WTIAFYNJSA-N (2r)-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-WTIAFYNJSA-N 0.000 claims 1
- DMFQEDIRMMWZOK-VOQZNFBZSA-N (2r)-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-VOQZNFBZSA-N 0.000 claims 1
- DJKIPNZIOLJURK-TYCQWZJGSA-N (2r)-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-TYCQWZJGSA-N 0.000 claims 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 claims 1
- GBTFNEFNFRBZBJ-ILCQWTCRSA-N (2r)-2-(4-chlorophenyl)-3-[(3s,5r)-3,5-dimethylpiperazin-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)N1C[C@H](C)N[C@H](C)C1 GBTFNEFNFRBZBJ-ILCQWTCRSA-N 0.000 claims 1
- JOADGYMGMILDPB-WTIAFYNJSA-N (2r)-2-(4-chlorophenyl)-3-[4-(2-hydroxyethyl)piperazin-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)N1CCN(CCO)CC1 JOADGYMGMILDPB-WTIAFYNJSA-N 0.000 claims 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 claims 1
- 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
- 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 claims 1
- OJQBGEUQOPGUJO-SLYNCCJLSA-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-methylpiperazin-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)N1CCN(C)CC1 OJQBGEUQOPGUJO-SLYNCCJLSA-N 0.000 claims 1
- GROLACOOUFTTBG-WVGSSIFTSA-N (2r)-2-[3-fluoro-4-(trifluoromethoxy)phenyl]-1-[4-[(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)CC(C=12)C)C=1C=C(F)C(OC(F)(F)F)=CC=1)N1CCOCC1 GROLACOOUFTTBG-WVGSSIFTSA-N 0.000 claims 1
- JCNGTRXRBGDTTA-GTCCEBARSA-N (2r)-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-(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(=CC=1)C(F)(F)F)N1CCC(O)CC1 JCNGTRXRBGDTTA-GTCCEBARSA-N 0.000 claims 1
- XBLQKLOXSQXHJY-ZWCUEREDSA-N (2r)-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-(4-methylpiperazin-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)N1CCN(C)CC1 XBLQKLOXSQXHJY-ZWCUEREDSA-N 0.000 claims 1
- MHAHVLOPCSKGNI-NHCICSSKSA-N (2r)-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-(4-propan-2-ylpiperazin-1-yl)propan-1-one Chemical compound C1CN(C(C)C)CCN1C[C@@H](C=1C=C(F)C(=CC=1)C(F)(F)F)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 MHAHVLOPCSKGNI-NHCICSSKSA-N 0.000 claims 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 claims 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 claims 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 claims 1
- UWIOHODNDKXYAP-LSTHTHJFSA-N (2r)-3-(azetidin-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)N1CCC1 UWIOHODNDKXYAP-LSTHTHJFSA-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
- QSBNMLHJMWKHPC-PERKRYKHSA-N (2s)-2-(3,4-dichlorophenyl)-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(Cl)C(Cl)=CC=1)NC1CCOCC1 QSBNMLHJMWKHPC-PERKRYKHSA-N 0.000 claims 1
- RFVHSXAEGORYON-MDYRTPRTSA-N (2s)-2-(3,4-dichlorophenyl)-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)C(Cl)=C1 RFVHSXAEGORYON-MDYRTPRTSA-N 0.000 claims 1
- PWOQUDDUGDELMH-YVWKXTFCSA-N (2s)-2-(3-bromo-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(Br)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 PWOQUDDUGDELMH-YVWKXTFCSA-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
- 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
- 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
- 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-QLGUMYEUSA-N (2s)-2-(4-bromophenyl)-3-[(4,4-dimethylcyclohexyl)amino]-1-[4-[(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)CC(C=12)C)C=1C=CC(Br)=CC=1)NC1CCC(C)(C)CC1 LXYGYMUEGJOHPL-QLGUMYEUSA-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
- ACYVWONXYYNPDK-MDYRTPRTSA-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-(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(F)=C1 ACYVWONXYYNPDK-MDYRTPRTSA-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
- CHZXOMCJYQFHSX-HCLVMJGWSA-N (2s)-2-(4-chloro-3-fluorophenyl)-3-(cyclopentylmethylamino)-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)NCC1CCCC1 CHZXOMCJYQFHSX-HCLVMJGWSA-N 0.000 claims 1
- DCUUIEBXVIUTHO-FPDPHYFHSA-N (2s)-2-(4-chloro-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(Cl)=CC=1)NCC1CC1 DCUUIEBXVIUTHO-FPDPHYFHSA-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
- NHOOVUOOHFQRHO-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-methoxypiperidin-1-yl)propan-1-one Chemical compound C1CC(OC)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 NHOOVUOOHFQRHO-SXSPYAJSSA-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
- 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 1
- IHLLUUVHYRQMCS-YGRUPMCMSA-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-methoxycyclohexyl)amino]propan-1-one Chemical compound C1CC(OC)CCC1NC[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 IHLLUUVHYRQMCS-YGRUPMCMSA-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
- 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 1
- 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 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
- GRZXWCHAXNAUHY-AHRSYUTCSA-N (2s)-2-(4-chlorophenyl)-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)C=C1 GRZXWCHAXNAUHY-AHRSYUTCSA-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-SXSPYAJSSA-N (2s)-2-(4-chlorophenyl)-3-(cyclohexylamino)-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)NC1CCCCC1 SBBKNPLQAOQYBE-SXSPYAJSSA-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
- 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 1
- DJKIPNZIOLJURK-HBGVWJBISA-N (2s)-2-(4-chlorophenyl)-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(Cl)=CC=1)NCC1CC1 DJKIPNZIOLJURK-HBGVWJBISA-N 0.000 claims 1
- 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 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
- 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
- AGKRBOABBMQFSL-HHXXYDBFSA-N (2s)-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-HHXXYDBFSA-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
- 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
- HPLLXKZTFYMEBR-MDYRTPRTSA-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-(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-MDYRTPRTSA-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
- 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 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
- 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
- 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
- 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
- CFBLBJLZEMERSN-KPCPBYSCSA-N (2s)-3-[bis(cyclopropylmethyl)amino]-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]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)N(CC1CC1)CC1CC1 CFBLBJLZEMERSN-KPCPBYSCSA-N 0.000 claims 1
- MOFXCWWIQFLBCN-SUYBPPKGSA-N (2s)-3-amino-2-(3,4-dichlorophenyl)-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(Cl)=C1 MOFXCWWIQFLBCN-SUYBPPKGSA-N 0.000 claims 1
- 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
- AEFICNJWUCHBJA-XYPHTWIQSA-N (2s)-3-amino-2-(4-bromophenyl)-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(Br)C=C1 AEFICNJWUCHBJA-XYPHTWIQSA-N 0.000 claims 1
- 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 1
- PDWRQDZWROMPGV-SRCQZFHVSA-N (2s)-3-amino-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 C1([C@@H](CN)C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)=CC=C(C(F)(F)F)C=C1F PDWRQDZWROMPGV-SRCQZFHVSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- VCZYNIODTLLAFV-LZQZEXGQSA-N 3-[[(2s)-2-(4-chlorophenyl)-3-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-oxopropyl]amino]propanamide Chemical compound C1([C@@H](CNCCC(N)=O)C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)=CC=C(Cl)C=C1 VCZYNIODTLLAFV-LZQZEXGQSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- PWWMNMFVAPKKLE-LSTHTHJFSA-N 4-[(2r)-2-(4-chlorophenyl)-3-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-3-oxopropyl]piperazin-2-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)N1CCNC(=O)C1 PWWMNMFVAPKKLE-LSTHTHJFSA-N 0.000 claims 1
- 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 1
- 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 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000013160 medical therapy Methods 0.000 claims 1
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
Classifications
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Applications Claiming Priority (2)
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| US81871806P | 2006-07-06 | 2006-07-06 | |
| PCT/US2007/072885 WO2008006040A1 (en) | 2006-07-06 | 2007-07-05 | Hydroxylated and methoxylated cyclopenta [d] pyrimidines as akt protein kinase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110908T1 true HRP20110908T1 (hr) | 2012-02-29 |
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| HR20110908T HRP20110908T1 (hr) | 2006-07-06 | 2011-12-02 | Hidroksilirani i metoksilirani ciklopenta [d] pirimidini kao inhibitori kinaze akt proteina |
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| EP2054418B1 (en) * | 2006-07-06 | 2011-11-09 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| US8329701B2 (en) | 2006-07-06 | 2012-12-11 | Array Biopharma Inc. | Dihydrofuro pyrimidines as AKT protein kinase inhibitors |
| UA95641C2 (en) * | 2006-07-06 | 2011-08-25 | Эррей Биофарма Инк. | Hydroxylated cyclopenta [d] 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 |
| BRPI0713555A2 (pt) | 2006-07-06 | 2012-03-20 | Array Biopharma, Inc. | ciclopenta [d] pirimidinas como inibidores de akt protéina cinase |
| US20110135569A1 (en) | 2007-03-20 | 2011-06-09 | Peak Biosciences Inc. | Method for therapeutic administration of radionucleosides |
| CA2692506C (en) | 2007-07-05 | 2015-11-24 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
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