NZ582692A - Pyrimidyl cyclopentanes as akt protein kinase inhibitors - Google Patents

Info

Publication number

NZ582692A

NZ582692A NZ582692A NZ58269208A NZ582692A NZ 582692 A NZ582692 A NZ 582692A NZ 582692 A NZ582692 A NZ 582692A NZ 58269208 A NZ58269208 A NZ 58269208A NZ 582692 A NZ582692 A NZ 582692A

Authority

NZ

New Zealand

Prior art keywords

cyclopenta

pyrimidin

dihydro

piperazin

methyl

Prior art date

2007-07-05

Links

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• -1 Pyrimidyl cyclopentanes Chemical class 0.000 title claims abstract description 264
• 108091008611 Protein Kinase B Proteins 0.000 title claims abstract description 54
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
• 239000003909 protein kinase inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 219
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 55
• 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 claims abstract description 36
• 201000010099 disease Diseases 0.000 claims abstract description 33
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• 208000035475 disorder Diseases 0.000 claims abstract description 22
• 239000003814 drug Substances 0.000 claims abstract description 21
• 230000001404 mediated effect Effects 0.000 claims abstract description 19
• 241000124008 Mammalia Species 0.000 claims abstract description 16
• 238000004519 manufacturing process Methods 0.000 claims abstract description 11
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 10
• NEEIYKGPXDSGBL-LKRGOLFISA-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]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1 NEEIYKGPXDSGBL-LKRGOLFISA-N 0.000 claims abstract description 5
• 230000002526 effect on cardiovascular system Effects 0.000 claims abstract description 4
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 4
• 230000000626 neurodegenerative effect Effects 0.000 claims abstract description 4
• ZVYGXDZKUJTOIX-ZXFPDNNPSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](F)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1 ZVYGXDZKUJTOIX-ZXFPDNNPSA-N 0.000 claims abstract 2
• 238000000034 method Methods 0.000 claims description 85
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 claims description 75
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000004429 atom Chemical group 0.000 claims description 23
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 20
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
• 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 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
• 230000014759 maintenance of location Effects 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 10
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 10
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 10
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 10
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 9
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 9
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 9
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 8
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• KOHGXVITISGBPV-QEMXTEJRSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(C)(C)N1 KOHGXVITISGBPV-QEMXTEJRSA-N 0.000 claims description 4
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 230000004048 modification Effects 0.000 claims description 4
• 238000012986 modification Methods 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• AJAUYRZUZLBSAI-QEMXTEJRSA-N (2s)-1-[4-[(5r,7r)-7-methoxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C2=NC=NC3=C2[C@H](C)C[C@H]3OC)C=2C=CC(=CC=2)C(F)(F)F)CCN1 AJAUYRZUZLBSAI-QEMXTEJRSA-N 0.000 claims description 3
• GGAYRRSQBOODLT-LDQFHDLZSA-N (2s)-2-(4-chloro-2,5-difluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(Cl)=C(F)C=2)F)CC(C)(C)N1 GGAYRRSQBOODLT-LDQFHDLZSA-N 0.000 claims description 3
• XLELDVURKKAFNR-QEMXTEJRSA-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]-2-[(2s)-piperidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCCN1 XLELDVURKKAFNR-QEMXTEJRSA-N 0.000 claims description 3
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• IDXLRCUCCNYDMP-LKUPVBHCSA-N (2r)-1-[4-[(5r)-7,7-difluoro-5-methyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@H](C(=O)N2CCN(CC2)C=2N=CN=C3C(F)(F)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CC(C)(C)N1 IDXLRCUCCNYDMP-LKUPVBHCSA-N 0.000 claims description 2
• RHFLHCFOTKICHL-YHQLXQCYSA-N (2r)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[2-fluoro-4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](F)C[C@H](C=23)C)C=2C(=CC(=CC=2)C(F)(F)F)F)CC(C)(C)N1 RHFLHCFOTKICHL-YHQLXQCYSA-N 0.000 claims description 2
• GGXGZWAQHASGSZ-JJXUHFIVSA-N (2s)-1-[4-[(5r)-7,7-difluoro-5-methyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-2-[2-fluoro-4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3C(F)(F)C[C@H](C=23)C)C=2C(=CC(=CC=2)C(F)(F)F)F)CC(C)(C)N1 GGXGZWAQHASGSZ-JJXUHFIVSA-N 0.000 claims description 2
• PBQKPLNOMYBVEW-QLQMMUPBSA-N (2s)-1-[4-[(5r,7r)-7-hydroxy-5,7-dimethyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-1-methylpyrrolidin-2-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@](C)(O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CCN1C PBQKPLNOMYBVEW-QLQMMUPBSA-N 0.000 claims description 2
• VCGFUORZARZFEF-MLFRIMFESA-N (2s)-1-[4-[(5r,7r)-7-hydroxy-5,7-dimethyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@](C)(O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CCN1 VCGFUORZARZFEF-MLFRIMFESA-N 0.000 claims description 2
• DASSZTKFRRUZCP-DKOYFPBOSA-N (2s)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-1-methylpyrrolidin-2-yl]-2-(4-methylsulfonylphenyl)ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)S(C)(=O)=O)CCN1C DASSZTKFRRUZCP-DKOYFPBOSA-N 0.000 claims description 2
• XFHVYPRSEDNUFU-QEMXTEJRSA-N (2s)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-1-methylpyrrolidin-2-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CCN1C XFHVYPRSEDNUFU-QEMXTEJRSA-N 0.000 claims description 2
• RNDKLFPVTJZXMV-DKOYFPBOSA-N (2s)-1-[4-[(5r,7r)-7-methoxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-1-methylpyrrolidin-2-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C2=NC=NC3=C2[C@H](C)C[C@H]3OC)C=2C=CC(=CC=2)C(F)(F)F)CCN1C RNDKLFPVTJZXMV-DKOYFPBOSA-N 0.000 claims description 2
• ZGVMQUGMOPZOJC-PBEJRMEISA-N (2s)-2-(4-bromophenyl)-1-[4-[(5r)-7,7-difluoro-5-methyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3C(F)(F)C[C@H](C=23)C)C=2C=CC(Br)=CC=2)CC(C)(C)N1 ZGVMQUGMOPZOJC-PBEJRMEISA-N 0.000 claims description 2
• XQEXQPDMGGGJHS-WCSGGZKSSA-N (2s)-2-(4-bromophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5,7-dimethyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@](C)(O)C[C@H](C=23)C)C=2C=CC(Br)=CC=2)CC(C)(C)N1 XQEXQPDMGGGJHS-WCSGGZKSSA-N 0.000 claims description 2
• MCDVPXUUDXCZPQ-QEMXTEJRSA-N (2s)-2-(4-bromophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Br)=CC=2)CC(C)(C)N1 MCDVPXUUDXCZPQ-QEMXTEJRSA-N 0.000 claims description 2
• KOQKCNFHTUUWJI-SYNNKVJXSA-N (2s)-2-(4-bromophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](F)C[C@H](C=23)C)C=2C=CC(Br)=CC=2)CC(C)(C)N1 KOQKCNFHTUUWJI-SYNNKVJXSA-N 0.000 claims description 2
• IGINBFWJURHEML-RIYQWJRFSA-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]-2-[(2r)-pyrrolidin-2-yl]ethanone Chemical compound C([C@@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(Cl)=CC=2)CCN1 IGINBFWJURHEML-RIYQWJRFSA-N 0.000 claims description 2
• IGINBFWJURHEML-WBHLOVLFSA-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]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(Cl)=CC=2)CCN1 IGINBFWJURHEML-WBHLOVLFSA-N 0.000 claims description 2
• AXFGTDZYKBQYQW-MMCAFHBRSA-N (2s)-2-(4-chloro-3-fluorophenyl)-1-[4-[(5r,7s)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](F)C[C@H](C=23)C)C=2C=C(F)C(Cl)=CC=2)CCN1 AXFGTDZYKBQYQW-MMCAFHBRSA-N 0.000 claims description 2
• DBNPCFRCZQQNNM-BTIFBSDPSA-N (2s)-2-(4-chloro-3-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(Cl)=CC=2)CC(C)(C)N1 DBNPCFRCZQQNNM-BTIFBSDPSA-N 0.000 claims description 2
• DBNPCFRCZQQNNM-BZDYGPBWSA-N (2s)-2-(4-chloro-3-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=C(F)C(Cl)=CC=2)CC(C)(C)N1 DBNPCFRCZQQNNM-BZDYGPBWSA-N 0.000 claims description 2
• OZZBPRLCCCVZBE-ZNPMGDIFSA-N (2s)-2-(4-chlorophenyl)-1-[(3s)-4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]-3-methylpiperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN([C@H](C2)C)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1 OZZBPRLCCCVZBE-ZNPMGDIFSA-N 0.000 claims description 2
• PZDFWZSALKFSMT-ZEFBCVDJSA-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]-2-[(2r)-1-methylpyrrolidin-2-yl]ethanone Chemical compound C([C@@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1C PZDFWZSALKFSMT-ZEFBCVDJSA-N 0.000 claims description 2
• NEEIYKGPXDSGBL-FEGHXTNJSA-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]-2-[(2r)-pyrrolidin-2-yl]ethanone Chemical compound C([C@@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1 NEEIYKGPXDSGBL-FEGHXTNJSA-N 0.000 claims description 2
• ZOAWIPAEUPZJIV-QBTGUUFSSA-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]-2-[(2s)-1-(2-hydroxy-2-methylpropyl)pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1CC(C)(C)O ZOAWIPAEUPZJIV-QBTGUUFSSA-N 0.000 claims description 2
• SYVAKCTZZGZWME-QBTGUUFSSA-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]-2-[(2s)-1-(2-methoxyethyl)pyrrolidin-2-yl]ethanone Chemical compound COCCN1CCC[C@H]1[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 SYVAKCTZZGZWME-QBTGUUFSSA-N 0.000 claims description 2
• QLPNCJOLECYJKL-QEMXTEJRSA-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]-2-[(3r)-4-methylmorpholin-3-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)OCCN1C QLPNCJOLECYJKL-QEMXTEJRSA-N 0.000 claims description 2
• QLPNCJOLECYJKL-SYNNKVJXSA-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]-2-[(3r)-4-methylmorpholin-3-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)OCCN1C QLPNCJOLECYJKL-SYNNKVJXSA-N 0.000 claims description 2
• AMNJOBCQNPPENC-WOSKWAQLSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-1-(2,2-difluoroethyl)pyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1CC(F)F AMNJOBCQNPPENC-WOSKWAQLSA-N 0.000 claims description 2
• YWFVYRYNVFJMQP-ZJNJKDKRSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-1-(cyclopropylmethyl)pyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1CC1CC1 YWFVYRYNVFJMQP-ZJNJKDKRSA-N 0.000 claims description 2
• OJKNLOFSNGKISA-VPJOFFEXSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-1-ethyl-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CC(C)(C)N(CC)[C@@H]1[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 OJKNLOFSNGKISA-VPJOFFEXSA-N 0.000 claims description 2
• LHQSPTBYNIXHJS-HARLFGEKSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r)-5-(hydroxymethyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound N1C(C)(C)CC[C@H]1[C@H](C=1C=CC(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](CO)CCC=3N=CN=2)CC1 LHQSPTBYNIXHJS-HARLFGEKSA-N 0.000 claims description 2
• AATFGCSBGPLZTP-WJMWBRGCSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-5-(fluoromethyl)-7-hydroxy-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound N1C(C)(C)CC[C@H]1[C@H](C=1C=CC(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](CF)C[C@@H](O)C=3N=CN=2)CC1 AATFGCSBGPLZTP-WJMWBRGCSA-N 0.000 claims description 2
• ASVATSKHMUOZCG-WCSGGZKSSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5,7-dimethyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@](C)(O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(C)(C)N1 ASVATSKHMUOZCG-WCSGGZKSSA-N 0.000 claims description 2
• JFTIFYNZZKGWRZ-WJMWBRGCSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-(hydroxymethyl)-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound N1C(C)(C)CC[C@H]1[C@H](C=1C=CC(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](CO)C[C@@H](O)C=3N=CN=2)CC1 JFTIFYNZZKGWRZ-WJMWBRGCSA-N 0.000 claims description 2
• AXICWQITLRXKEH-DKOYFPBOSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-methoxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C2=NC=NC3=C2[C@H](C)C[C@H]3OC)C=2C=CC(Cl)=CC=2)CC(C)(C)N1 AXICWQITLRXKEH-DKOYFPBOSA-N 0.000 claims description 2
• QFJZHBJUDOSSHI-SYNNKVJXSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](F)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(C)(C)N1 QFJZHBJUDOSSHI-SYNNKVJXSA-N 0.000 claims description 2
• KOHGXVITISGBPV-SYNNKVJXSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(C)(C)N1 KOHGXVITISGBPV-SYNNKVJXSA-N 0.000 claims description 2
• LWAIVXYLRFXPLQ-ZJNJKDKRSA-N (2s)-2-(4-cyclopropylphenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-1-methylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C2CC2)CCN1C LWAIVXYLRFXPLQ-ZJNJKDKRSA-N 0.000 claims description 2
• GMSADNDLRCPPJI-TVZVLCPFSA-N (2s)-2-(4-cyclopropylphenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-1-propan-2-ylpyrrolidin-2-yl]ethanone Chemical compound CC(C)N1CCC[C@H]1[C@H](C=1C=CC(=CC=1)C1CC1)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 GMSADNDLRCPPJI-TVZVLCPFSA-N 0.000 claims description 2
• DNNUTZJOWDKFAP-TYVKFHQSSA-N (2s)-2-(4-cyclopropylphenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C2CC2)CCN1 DNNUTZJOWDKFAP-TYVKFHQSSA-N 0.000 claims description 2
• XFWADCSXSMAOJS-UIVXKWKOSA-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]-2-[(2s)-1-methylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2SC(Br)=CC=2)CCN1C XFWADCSXSMAOJS-UIVXKWKOSA-N 0.000 claims description 2
• UZDZFNQDPRZUQA-NXEZDXNNSA-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]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2SC(Br)=CC=2)CCN1 UZDZFNQDPRZUQA-NXEZDXNNSA-N 0.000 claims description 2
• WHMFGSWUZHPYBQ-UIVXKWKOSA-N (2s)-2-(5-bromothiophen-2-yl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2SC(Br)=CC=2)CC(C)(C)N1 WHMFGSWUZHPYBQ-UIVXKWKOSA-N 0.000 claims description 2
• UDTHWQUTUKXHIH-NXEZDXNNSA-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]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2SC(Cl)=CC=2)CCN1 UDTHWQUTUKXHIH-NXEZDXNNSA-N 0.000 claims description 2
• UDTHWQUTUKXHIH-MMMWYMCRSA-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]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2SC(Cl)=CC=2)CCN1 UDTHWQUTUKXHIH-MMMWYMCRSA-N 0.000 claims description 2
• LVLHDTXRNMGABW-QBTGUUFSSA-N (2s)-2-[(2s)-1-azaspiro[4.4]nonan-2-yl]-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H](N1)[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC21CCCC2 LVLHDTXRNMGABW-QBTGUUFSSA-N 0.000 claims description 2
• CFQSALVGMXONTH-DEZRYOJYSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](F)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CC(C)(C)N1 CFQSALVGMXONTH-DEZRYOJYSA-N 0.000 claims description 2
• YYOOIOTXVIMDGC-WCSGGZKSSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5,7-dimethyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@](C)(O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CC(C)(C)N1 YYOOIOTXVIMDGC-WCSGGZKSSA-N 0.000 claims description 2
• ONNYNNSBAHXUJA-DKOYFPBOSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-(4-methylsulfonylphenyl)ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)S(C)(=O)=O)CC(C)(C)N1 ONNYNNSBAHXUJA-DKOYFPBOSA-N 0.000 claims description 2
• FAMGBAKCSHPHBO-DQFIBICCSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-(4-phenylphenyl)ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC(C)(C)N1 FAMGBAKCSHPHBO-DQFIBICCSA-N 0.000 claims description 2
• KNHPRTNPYBKUFV-ZJNJKDKRSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[4-(1h-pyrazol-4-yl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C2=CNN=C2)CC(C)(C)N1 KNHPRTNPYBKUFV-ZJNJKDKRSA-N 0.000 claims description 2
• LMSHQCHTOMUFAR-SYNNKVJXSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CC(C)(C)N1 LMSHQCHTOMUFAR-SYNNKVJXSA-N 0.000 claims description 2
• GTFHQLRIFMRUIV-LKRGOLFISA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-2-[2-fluoro-3-(trifluoromethyl)phenyl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=C(C=CC=2)C(F)(F)F)F)CC(C)(C)N1 GTFHQLRIFMRUIV-LKRGOLFISA-N 0.000 claims description 2
• MARWZZULKRRMKU-BTIFBSDPSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-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]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(=CC=2)C(F)(F)F)F)CC(C)(C)N1 MARWZZULKRRMKU-BTIFBSDPSA-N 0.000 claims description 2
• MARWZZULKRRMKU-BZDYGPBWSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-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]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C(=CC(=CC=2)C(F)(F)F)F)CC(C)(C)N1 MARWZZULKRRMKU-BZDYGPBWSA-N 0.000 claims description 2
• AYQHZUUHZNXEBP-LRYKZCBQSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-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]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(OC(F)(F)F)=CC=2)CC(C)(C)N1 AYQHZUUHZNXEBP-LRYKZCBQSA-N 0.000 claims description 2
• VERHIYABCPTLIA-BTIFBSDPSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-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]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(=CC=2)C(F)(F)F)CC(C)(C)N1 VERHIYABCPTLIA-BTIFBSDPSA-N 0.000 claims description 2
• VERHIYABCPTLIA-BZDYGPBWSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-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]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=C(F)C(=CC=2)C(F)(F)F)CC(C)(C)N1 VERHIYABCPTLIA-BZDYGPBWSA-N 0.000 claims description 2
• JSPWPZFSOXQLPH-WBHLOVLFSA-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]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(=CC=2)C(F)(F)F)CCN1 JSPWPZFSOXQLPH-WBHLOVLFSA-N 0.000 claims description 2
• JSPWPZFSOXQLPH-MMCAFHBRSA-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]-2-[(2s)-pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=C(F)C(=CC=2)C(F)(F)F)CCN1 JSPWPZFSOXQLPH-MMCAFHBRSA-N 0.000 claims description 2
• QGHFVNNDJJNFFE-ZJNJKDKRSA-N (2s)-2-[4-(2-aminopyrimidin-5-yl)phenyl]-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C=2C=NC(N)=NC=2)CC(C)(C)N1 QGHFVNNDJJNFFE-ZJNJKDKRSA-N 0.000 claims description 2
• UYSANVPQADKUEN-UTQVJTIVSA-N (5r)-5-[(1s)-1-(4-chlorophenyl)-2-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-oxoethyl]pyrrolidin-2-one Chemical compound C([C@@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(=O)N1 UYSANVPQADKUEN-UTQVJTIVSA-N 0.000 claims description 2
• UYSANVPQADKUEN-IZQPOCBFSA-N (5s)-5-[(1s)-1-(4-chlorophenyl)-2-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-oxoethyl]pyrrolidin-2-one Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(=O)N1 UYSANVPQADKUEN-IZQPOCBFSA-N 0.000 claims description 2
• DVIKZCZCIOJAFS-IZQPOCBFSA-N (5s)-5-[(1s)-2-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-oxo-1-[4-(trifluoromethyl)phenyl]ethyl]pyrrolidin-2-one Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CC(=O)N1 DVIKZCZCIOJAFS-IZQPOCBFSA-N 0.000 claims description 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
• UBLVXRGFUNXRSK-DKOYFPBOSA-N 4-[(1s)-1-[(2s)-5,5-dimethylpyrrolidin-2-yl]-2-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-oxoethyl]benzonitrile Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C#N)CC(C)(C)N1 UBLVXRGFUNXRSK-DKOYFPBOSA-N 0.000 claims description 2
• ARPFPMPETZCDAU-QEMXTEJRSA-N 4-[(1s)-2-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-1-[(2s)-1-methylpyrrolidin-2-yl]-2-oxoethyl]benzamide Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(N)=O)CCN1C ARPFPMPETZCDAU-QEMXTEJRSA-N 0.000 claims description 2
• MHHOJWBDPSBBDI-LKRGOLFISA-N 4-[(1s)-2-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-oxo-1-[(2s)-pyrrolidin-2-yl]ethyl]benzamide Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(N)=O)CCN1 MHHOJWBDPSBBDI-LKRGOLFISA-N 0.000 claims description 2
• LEOWJIGMXXBIMH-QEMXTEJRSA-N 4-[(1s)-2-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-oxo-1-[(2s)-pyrrolidin-2-yl]ethyl]benzonitrile Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C#N)CCN1 LEOWJIGMXXBIMH-QEMXTEJRSA-N 0.000 claims description 2
• UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical group CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 2
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
• 125000004043 oxo group Chemical group O=* 0.000 claims 3
• WGEJIVLERCLFNF-BTIFBSDPSA-N (2s)-2-(2,4-dichlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(Cl)=CC=2)Cl)CC(C)(C)N1 WGEJIVLERCLFNF-BTIFBSDPSA-N 0.000 claims 1
• DVWLEAFBRLTUKQ-BTIFBSDPSA-N (2s)-2-(3,4-dichlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(Cl)C(Cl)=CC=2)CC(C)(C)N1 DVWLEAFBRLTUKQ-BTIFBSDPSA-N 0.000 claims 1
• GEERFIKIHAKETR-BTIFBSDPSA-N (2s)-2-(3,4-difluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(F)=CC=2)CC(C)(C)N1 GEERFIKIHAKETR-BTIFBSDPSA-N 0.000 claims 1
• BGOWNUNGLJHGKO-FHZYATBESA-N (2s)-2-(3-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3CC[C@H](C=23)C)C=2C=C(Cl)C=CC=2)CC(C)(C)N1 BGOWNUNGLJHGKO-FHZYATBESA-N 0.000 claims 1
• PKFWHNKIXDWAHF-QEMXTEJRSA-N (2s)-2-(3-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(Cl)C=CC=2)CC(C)(C)N1 PKFWHNKIXDWAHF-QEMXTEJRSA-N 0.000 claims 1
• YHTSWIVQYCSQER-BTIFBSDPSA-N (2s)-2-(4-bromo-2-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(Br)=CC=2)F)CC(C)(C)N1 YHTSWIVQYCSQER-BTIFBSDPSA-N 0.000 claims 1
• DMMDFDUBQHEPDQ-BTIFBSDPSA-N (2s)-2-(4-bromo-3-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(Br)=CC=2)CC(C)(C)N1 DMMDFDUBQHEPDQ-BTIFBSDPSA-N 0.000 claims 1
• OCYQNUNFTYVQRE-SURYNDKFSA-N (2s)-2-(4-chloro-2-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5,7-dimethyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@](C)(O)C[C@H](C=23)C)C=2C(=CC(Cl)=CC=2)F)CC(C)(C)N1 OCYQNUNFTYVQRE-SURYNDKFSA-N 0.000 claims 1
• ZBUKELXFBDMFKY-BTIFBSDPSA-N (2s)-2-(4-chloro-2-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(Cl)=CC=2)F)CC(C)(C)N1 ZBUKELXFBDMFKY-BTIFBSDPSA-N 0.000 claims 1
• AANZSBNNRYHRRN-BZDYGPBWSA-N (2s)-2-(4-chloro-2-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](F)C[C@H](C=23)C)C=2C(=CC(Cl)=CC=2)F)CC(C)(C)N1 AANZSBNNRYHRRN-BZDYGPBWSA-N 0.000 claims 1
• YHSDAHWHJFHOGJ-DKOYFPBOSA-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]-2-[(2s)-1-methylpiperidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCCN1C YHSDAHWHJFHOGJ-DKOYFPBOSA-N 0.000 claims 1
• PZDFWZSALKFSMT-QEMXTEJRSA-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]-2-[(2s)-1-methylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1C PZDFWZSALKFSMT-QEMXTEJRSA-N 0.000 claims 1
• BLBOCVKCGYAKDP-QBTGUUFSSA-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]-2-[(2s)-1-propan-2-ylpyrrolidin-2-yl]ethanone Chemical compound CC(C)N1CCC[C@H]1[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 BLBOCVKCGYAKDP-QBTGUUFSSA-N 0.000 claims 1
• PZDFWZSALKFSMT-SYNNKVJXSA-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]-2-[(2s)-1-methylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1C PZDFWZSALKFSMT-SYNNKVJXSA-N 0.000 claims 1
• PTVFSXRIKOGGFI-CCMRYFRJSA-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]-2-[(3r)-morpholin-3-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)OCCN1 PTVFSXRIKOGGFI-CCMRYFRJSA-N 0.000 claims 1
• JUPHFKZPZRICTE-SPTRTZJMSA-N (2s)-2-(4-cyclopropylphenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C2CC2)CC(C)(C)N1 JUPHFKZPZRICTE-SPTRTZJMSA-N 0.000 claims 1
• POXBGKDKQNKAPI-SRPRTCBCSA-N (2s)-2-(4-tert-butylphenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(C)(C)C)CC(C)(C)N1 POXBGKDKQNKAPI-SRPRTCBCSA-N 0.000 claims 1
• CJPXKLBOSQMEBL-UIVXKWKOSA-N (2s)-2-(5-chlorothiophen-2-yl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2SC(Cl)=CC=2)CC(C)(C)N1 CJPXKLBOSQMEBL-UIVXKWKOSA-N 0.000 claims 1
• TWOZFOQBKBCAAF-RAHIQWLESA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-naphthalen-1-ylethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3CC[C@H](C=23)C)C=2C3=CC=CC=C3C=CC=2)CC(C)(C)N1 TWOZFOQBKBCAAF-RAHIQWLESA-N 0.000 claims 1
• OVIAUVBNVNYRCU-QEMXTEJRSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[3-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(C=CC=2)C(F)(F)F)CC(C)(C)N1 OVIAUVBNVNYRCU-QEMXTEJRSA-N 0.000 claims 1
• JYYVIFBWCBTJLV-XVZHEKKHSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-naphthalen-1-ylethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C3=CC=CC=C3C=CC=2)CC(C)(C)N1 JYYVIFBWCBTJLV-XVZHEKKHSA-N 0.000 claims 1
• WNRFOGRLHLKYDA-XVZHEKKHSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-naphthalen-2-ylethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C3C=CC=CC3=CC=2)CC(C)(C)N1 WNRFOGRLHLKYDA-XVZHEKKHSA-N 0.000 claims 1
• CFQSALVGMXONTH-SYNNKVJXSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7s)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](F)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CC(C)(C)N1 CFQSALVGMXONTH-SYNNKVJXSA-N 0.000 claims 1
• DXJUDXWHQMNCRK-QSABTFIQSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-2-(2-fluoro-4-methoxyphenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound FC1=CC(OC)=CC=C1[C@H](C(=O)N1CCN(CC1)C=1C=2[C@H](C)C[C@@H](O)C=2N=CN=1)[C@H]1NC(C)(C)CC1 DXJUDXWHQMNCRK-QSABTFIQSA-N 0.000 claims 1
• ZTXAANUHZVYPTI-DKOYFPBOSA-N (2s)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-2-(2-fluoro-4-methylphenyl)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(C)=CC=2)F)CC(C)(C)N1 ZTXAANUHZVYPTI-DKOYFPBOSA-N 0.000 claims 1
• MOZRQQTUYAYCQT-FQEVSTJZSA-N n-[[(3s)-3-amino-1-(5-ethyl-7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl]methyl]-2,4-difluorobenzamide Chemical compound C([C@]1(CCN(C1)C=1N=CN=C2NC=C(C=12)CC)N)NC(=O)C1=CC=C(F)C=C1F MOZRQQTUYAYCQT-FQEVSTJZSA-N 0.000 claims 1
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• YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
• FEMSWPPUYTTWKZ-LKRGOLFISA-N (2s)-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]-2-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(=CC=2)C(F)(F)F)CCN1 FEMSWPPUYTTWKZ-LKRGOLFISA-N 0.000 description 1
• IBRLWIUXHMUSTP-OXJVEHPISA-N (2s)-2-(2,4-dichlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(Cl)=CC=2)Cl)CC(C)(C)N1 IBRLWIUXHMUSTP-OXJVEHPISA-N 0.000 description 1
• IHAVIXJLIUSFNH-OXJVEHPISA-N (2s)-2-(3,4-dichlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(Cl)C(Cl)=CC=2)CC(C)(C)N1 IHAVIXJLIUSFNH-OXJVEHPISA-N 0.000 description 1
• HANLRSYEVKKMLS-OXJVEHPISA-N (2s)-2-(3,4-difluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(F)=CC=2)CC(C)(C)N1 HANLRSYEVKKMLS-OXJVEHPISA-N 0.000 description 1
• OVBDAWOSKCYUAM-JCPYKCQDSA-N (2s)-2-(3-bromophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3CC[C@H](C=23)C)C=2C=C(Br)C=CC=2)CC(C)(C)N1 OVBDAWOSKCYUAM-JCPYKCQDSA-N 0.000 description 1
• JFZGHODXOBMYRX-GVCHMSSBSA-N (2s)-2-(3-bromophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(Br)C=CC=2)CC(C)(C)N1 JFZGHODXOBMYRX-GVCHMSSBSA-N 0.000 description 1
• PZULBMJKMNBFHB-JCPYKCQDSA-N (2s)-2-(3-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r)-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3CC[C@H](C=23)C)C=2C=C(Cl)C=CC=2)CC(C)(C)N1 PZULBMJKMNBFHB-JCPYKCQDSA-N 0.000 description 1
• ZZSYVNDOBXNFEN-GVCHMSSBSA-N (2s)-2-(3-chlorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(Cl)C=CC=2)CC(C)(C)N1 ZZSYVNDOBXNFEN-GVCHMSSBSA-N 0.000 description 1
• XKFMDCCXXQVAAB-FHMFRLQOSA-N (2s)-2-(4-bromo-2-fluorophenyl)-2-[(2r)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(Br)=CC=2)F)CC(C)(C)N1 XKFMDCCXXQVAAB-FHMFRLQOSA-N 0.000 description 1
• UZSIVWJXCPHGSR-GJZGRUSLSA-N (2s)-2-(4-bromo-3-fluorophenyl)-2-[(2s)-5,5-dimethyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]acetic acid Chemical compound C1CC(C)(C)N(C(=O)OC(C)(C)C)[C@@H]1[C@@H](C(O)=O)C1=CC=C(Br)C(F)=C1 UZSIVWJXCPHGSR-GJZGRUSLSA-N 0.000 description 1
• OPKAFYORRULBNC-OXJVEHPISA-N (2s)-2-(4-bromo-3-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(Br)=CC=2)CC(C)(C)N1 OPKAFYORRULBNC-OXJVEHPISA-N 0.000 description 1
• KOQKCNFHTUUWJI-DEZRYOJYSA-N (2s)-2-(4-bromophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](F)C[C@H](C=23)C)C=2C=CC(Br)=CC=2)CC(C)(C)N1 KOQKCNFHTUUWJI-DEZRYOJYSA-N 0.000 description 1
• AZNKTECBENOMQB-GJZGRUSLSA-N (2s)-2-(4-chloro-2-fluorophenyl)-2-[(2s)-5,5-dimethyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]acetic acid Chemical compound C1CC(C)(C)N(C(=O)OC(C)(C)C)[C@@H]1[C@@H](C(O)=O)C1=CC=C(Cl)C=C1F AZNKTECBENOMQB-GJZGRUSLSA-N 0.000 description 1
• MTJMSVRKSCPDTI-OXJVEHPISA-N (2s)-2-(4-chloro-2-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C(=CC(Cl)=CC=2)F)CC(C)(C)N1 MTJMSVRKSCPDTI-OXJVEHPISA-N 0.000 description 1
• ZOUCQFSDWIJDNC-BTIFBSDPSA-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]-2-[(2s)-1-methylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=C(F)C(Cl)=CC=2)CCN1C ZOUCQFSDWIJDNC-BTIFBSDPSA-N 0.000 description 1
• XHDMYDLHSAAICG-TYVKFHQSSA-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]-2-[(2s)-1-propan-2-ylpyrrolidin-2-yl]ethanone Chemical compound CC(C)N1CCC[C@H]1[C@H](C=1C=C(F)C(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](C)C[C@@H](O)C=3N=CN=2)CC1 XHDMYDLHSAAICG-TYVKFHQSSA-N 0.000 description 1
• YEKYBFOXPKLPFD-SURYNDKFSA-N (2s)-2-(4-chloro-3-fluorophenyl)-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5,7-dimethyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@](C)(O)C[C@H](C=23)C)C=2C=C(F)C(Cl)=CC=2)CC(C)(C)N1 YEKYBFOXPKLPFD-SURYNDKFSA-N 0.000 description 1
• KNIAUQMPYFBCJK-PBEJRMEISA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r)-7,7-difluoro-5-methyl-5,6-dihydrocyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-5,5-dimethylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3C(F)(F)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(C)(C)N1 KNIAUQMPYFBCJK-PBEJRMEISA-N 0.000 description 1
• WCNXWJIZALQLTH-VACSVPNNSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7r)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]ethanone;hydrochloride Chemical compound Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](F)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1 WCNXWJIZALQLTH-VACSVPNNSA-N 0.000 description 1
• GNMUHTCTEVMICV-DKOYFPBOSA-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]-2-[(2s)-1,5,5-trimethylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(C)(C)N1C GNMUHTCTEVMICV-DKOYFPBOSA-N 0.000 description 1
• PCTZNUMCLFOXCU-SRPRTCBCSA-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]-2-[(2s)-1-(2-methoxyethyl)-5,5-dimethylpyrrolidin-2-yl]ethanone Chemical compound C1CC(C)(C)N(CCOC)[C@@H]1[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 PCTZNUMCLFOXCU-SRPRTCBCSA-N 0.000 description 1
• GGDGKPLGOYLEOE-QBTGUUFSSA-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]-2-[(2s)-1-(3-hydroxypropyl)pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1CCCO GGDGKPLGOYLEOE-QBTGUUFSSA-N 0.000 description 1
• XCXDOUGVTGFDMW-XVZHEKKHSA-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]-2-[(2s)-1-(oxan-4-yl)pyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1C1CCOCC1 XCXDOUGVTGFDMW-XVZHEKKHSA-N 0.000 description 1
• YDNDIBKGHKIRJG-GVCHMSSBSA-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]-2-[(2s)-1-methylpyrrolidin-2-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1C YDNDIBKGHKIRJG-GVCHMSSBSA-N 0.000 description 1
• HGSLEKNTRDLMFX-RERKUMTJSA-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]-2-[(2s)-1-propan-2-ylpyrrolidin-2-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.CC(C)N1CCC[C@H]1[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 HGSLEKNTRDLMFX-RERKUMTJSA-N 0.000 description 1
• PTVFSXRIKOGGFI-LKRGOLFISA-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]-2-[(3r)-morpholin-3-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)OCCN1 PTVFSXRIKOGGFI-LKRGOLFISA-N 0.000 description 1
• AIUKOSMJIYDXJQ-ZPWIABMXSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5r,7s)-7-fluoro-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]-2-[(2s)-pyrrolidin-2-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](F)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1 AIUKOSMJIYDXJQ-ZPWIABMXSA-N 0.000 description 1
• GNMUHTCTEVMICV-NPWUYRIISA-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]-2-[(2s)-1,5,5-trimethylpyrrolidin-2-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CC(C)(C)N1C GNMUHTCTEVMICV-NPWUYRIISA-N 0.000 description 1
• IMJSQHFZPTUKDX-ZPWIABMXSA-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]-2-[(3r)-morpholin-3-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)OCCN1 IMJSQHFZPTUKDX-ZPWIABMXSA-N 0.000 description 1
• DOYYJLRNVHHMGU-DKOYFPBOSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-1-(2-fluoroethyl)pyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1CCF DOYYJLRNVHHMGU-DKOYFPBOSA-N 0.000 description 1
• DTWAQJRESWWCQZ-DKOYFPBOSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-1-(2-hydroxyethyl)pyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C([C@H]1[C@@H](C(=O)N2CCN(CC2)C=2N=CN=C3[C@H](O)C[C@H](C=23)C)C=2C=CC(Cl)=CC=2)CCN1CCO DTWAQJRESWWCQZ-DKOYFPBOSA-N 0.000 description 1
• OJKNLOFSNGKISA-QBTGUUFSSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-1-ethyl-5,5-dimethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CC(C)(C)N(CC)[C@@H]1[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 OJKNLOFSNGKISA-QBTGUUFSSA-N 0.000 description 1
• LUSLIVUWNSKMPC-DKOYFPBOSA-N (2s)-2-(4-chlorophenyl)-2-[(2s)-1-ethylpyrrolidin-2-yl]-1-[4-[(5r,7r)-7-hydroxy-5-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound CCN1CCC[C@H]1[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 LUSLIVUWNSKMPC-DKOYFPBOSA-N 0.000 description 1
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