CA2656364C - Dihydrothieno pyrimidines as akt protein kinase inhibitors - Google Patents

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Publication number

CA2656364C

CA2656364C CA2656364A CA2656364A CA2656364C CA 2656364 C CA2656364 C CA 2656364C CA 2656364 A CA2656364 A CA 2656364A CA 2656364 A CA2656364 A CA 2656364A CA 2656364 C CA2656364 C CA 2656364C

Authority

CA

Canada

Prior art keywords

methyl

dihydrothieno

compound

piperazin

pyrimidin

Prior art date

2006-07-06

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 108091008611 Protein Kinase B Proteins 0.000 title claims abstract description 55
• 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract description 3
• 239000003909 protein kinase inhibitor Substances 0.000 title abstract description 3
• 150000003230 pyrimidines Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 283
• -1 resolved enantiomers Chemical class 0.000 claims abstract description 201
• 238000000034 method Methods 0.000 claims abstract description 81
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 238000011282 treatment Methods 0.000 claims abstract description 50
• 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 claims abstract description 36
• 201000010099 disease Diseases 0.000 claims abstract description 32
• 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 description 20
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 85
• UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 61
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
• 125000004429 atom Chemical group 0.000 claims description 35
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims description 32
• 239000003814 drug Substances 0.000 claims description 31
• 208000035475 disorder Diseases 0.000 claims description 26
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 241000124008 Mammalia Species 0.000 claims description 21
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 20
• 230000001404 mediated effect Effects 0.000 claims description 19
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
• 229910052731 fluorine Inorganic materials 0.000 claims description 17
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 15
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 12
• 125000004043 oxo group Chemical group O=* 0.000 claims description 11
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 8
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 8
• 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 8
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 8
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
• 125000002757 morpholinyl group Chemical group 0.000 claims description 7
• 230000026731 phosphorylation Effects 0.000 claims description 7
• 238000006366 phosphorylation reaction Methods 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 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 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
• 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 description 3
• 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 description 3
• 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims description 3
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
• 230000002757 inflammatory effect Effects 0.000 claims description 3
• 230000000626 neurodegenerative effect Effects 0.000 claims description 3
• 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 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
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
• QJCNXDZONNGTKP-LPHOPBHVSA-N (2r)-2-(4-chlorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-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)SCC=3N=CN=2)CNC(C)C)=CC=C(Cl)C=C1 QJCNXDZONNGTKP-LPHOPBHVSA-N 0.000 claims 1
• PNSNFWCLDHJDOS-STWLZBDKSA-N (2r)-2-(methylamino)-1-[(3s)-3-methyl-4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-(4-phenylmethoxyphenyl)propan-1-one Chemical compound C([C@@H](NC)C(=O)N1C[C@H](C)N(CC1)C=1C=2[C@H](C)SCC=2N=CN=1)C(C=C1)=CC=C1OCC1=CC=CC=C1 PNSNFWCLDHJDOS-STWLZBDKSA-N 0.000 claims 1
• IJEHBYUHSGXQIL-GDZNZVCISA-N (2r)-2-amino-3-(3,4-difluorophenyl)-1-[(3s)-3-methyl-4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN([C@H](C1)C)C=1N=CN=C2CS[C@H](C=12)C)C1=CC=C(F)C(F)=C1 IJEHBYUHSGXQIL-GDZNZVCISA-N 0.000 claims 1
• DJVNBIYWLMRTEL-PVQCJRHBSA-N (2r)-2-amino-3-(3,4-difluorophenyl)-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CSC(C=12)C)C1=CC=C(F)C(F)=C1 DJVNBIYWLMRTEL-PVQCJRHBSA-N 0.000 claims 1
• DJVNBIYWLMRTEL-MLGOLLRUSA-N (2r)-2-amino-3-(3,4-difluorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CS[C@@H](C=12)C)C1=CC=C(F)C(F)=C1 DJVNBIYWLMRTEL-MLGOLLRUSA-N 0.000 claims 1
• DJVNBIYWLMRTEL-BLLLJJGKSA-N (2r)-2-amino-3-(3,4-difluorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CS[C@H](C=12)C)C1=CC=C(F)C(F)=C1 DJVNBIYWLMRTEL-BLLLJJGKSA-N 0.000 claims 1
• KQMHAUFMTWRFTF-GDZNZVCISA-N (2r)-2-amino-3-(4-chloro-3-fluorophenyl)-1-[(3s)-3-methyl-4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN([C@H](C1)C)C=1N=CN=C2CS[C@H](C=12)C)C1=CC=C(Cl)C(F)=C1 KQMHAUFMTWRFTF-GDZNZVCISA-N 0.000 claims 1
• OBUSXZSNDGQNNR-PYUWXLGESA-N (2r)-2-amino-3-(4-chloro-3-fluorophenyl)-1-[4-(5-ethyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CSC(C=12)CC)C1=CC=C(Cl)C(F)=C1 OBUSXZSNDGQNNR-PYUWXLGESA-N 0.000 claims 1
• XAWQAIPEIPNSGB-PYUWXLGESA-N (2r)-2-amino-3-(4-chloro-3-fluorophenyl)-1-[4-(5-ethyl-6,6-dioxo-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C1=NC=NC2=C1C(S(C2)(=O)=O)CC)C1=CC=C(Cl)C(F)=C1 XAWQAIPEIPNSGB-PYUWXLGESA-N 0.000 claims 1
• MGUZARQONFVYEN-PVQCJRHBSA-N (2r)-2-amino-3-(4-chloro-3-fluorophenyl)-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CSC(C=12)C)C1=CC=C(Cl)C(F)=C1 MGUZARQONFVYEN-PVQCJRHBSA-N 0.000 claims 1
• MGUZARQONFVYEN-MLGOLLRUSA-N (2r)-2-amino-3-(4-chloro-3-fluorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CS[C@@H](C=12)C)C1=CC=C(Cl)C(F)=C1 MGUZARQONFVYEN-MLGOLLRUSA-N 0.000 claims 1
• MGUZARQONFVYEN-BLLLJJGKSA-N (2r)-2-amino-3-(4-chloro-3-fluorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CS[C@H](C=12)C)C1=CC=C(Cl)C(F)=C1 MGUZARQONFVYEN-BLLLJJGKSA-N 0.000 claims 1
• YFMREFBRFDJPDU-JJRVBVJISA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[(3s)-3-methyl-4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN([C@H](C1)C)C=1N=CN=C2CS[C@@H](C=12)C)C1=CC=C(Cl)C=C1 YFMREFBRFDJPDU-JJRVBVJISA-N 0.000 claims 1
• YFMREFBRFDJPDU-GRDNDAEWSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[(3s)-3-methyl-4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN([C@H](C1)C)C=1N=CN=C2CS[C@H](C=12)C)C1=CC=C(Cl)C=C1 YFMREFBRFDJPDU-GRDNDAEWSA-N 0.000 claims 1
• OBTIKMLDJKQPKL-MRXNPFEDSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-(5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1C=2CSCC=2N=CN=1)C1=CC=C(Cl)C=C1 OBTIKMLDJKQPKL-MRXNPFEDSA-N 0.000 claims 1
• ANUUSLSUVOFECW-PYUWXLGESA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-(5-ethyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CSC(C=12)CC)C1=CC=C(Cl)C=C1 ANUUSLSUVOFECW-PYUWXLGESA-N 0.000 claims 1
• ATNJKZPWHJZLJU-PYUWXLGESA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-(5-ethyl-6,6-dioxo-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C1=NC=NC2=C1C(S(C2)(=O)=O)CC)C1=CC=C(Cl)C=C1 ATNJKZPWHJZLJU-PYUWXLGESA-N 0.000 claims 1
• UDCLTQDGBYLTCA-FQNRMIAFSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CSC(C=12)C)C1=CC=C(Cl)C=C1 UDCLTQDGBYLTCA-FQNRMIAFSA-N 0.000 claims 1
• APVSADMEKPFZED-FQNRMIAFSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-(5-methyl-6,6-dioxo-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C1=NC=NC2=C1C(S(C2)(=O)=O)C)C1=CC=C(Cl)C=C1 APVSADMEKPFZED-FQNRMIAFSA-N 0.000 claims 1
• POIRUZQLUPFLEG-CRXJSJBGSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-(5-methyl-6-oxo-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C1=NC=NC2=C1C(S(C2)=O)C)C1=CC=C(Cl)C=C1 POIRUZQLUPFLEG-CRXJSJBGSA-N 0.000 claims 1
• SGWVDWXKEWMGSE-MRXNPFEDSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-(6,6-dioxo-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1C=2CS(=O)(=O)CC=2N=CN=1)C1=CC=C(Cl)C=C1 SGWVDWXKEWMGSE-MRXNPFEDSA-N 0.000 claims 1
• NENVRGDLRXIBLJ-NFXOVVRFSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-(6-oxo-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1C=2CS(=O)CC=2N=CN=1)C1=CC=C(Cl)C=C1 NENVRGDLRXIBLJ-NFXOVVRFSA-N 0.000 claims 1
• UDCLTQDGBYLTCA-CZUORRHYSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CS[C@@H](C=12)C)C1=CC=C(Cl)C=C1 UDCLTQDGBYLTCA-CZUORRHYSA-N 0.000 claims 1
• UDCLTQDGBYLTCA-XJKSGUPXSA-N (2r)-2-amino-3-(4-chlorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CS[C@H](C=12)C)C1=CC=C(Cl)C=C1 UDCLTQDGBYLTCA-XJKSGUPXSA-N 0.000 claims 1
• IRYJDAFKRUWQAH-GRDNDAEWSA-N (2r)-2-amino-3-(4-fluorophenyl)-1-[(3s)-3-methyl-4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN([C@H](C1)C)C=1N=CN=C2CS[C@H](C=12)C)C1=CC=C(F)C=C1 IRYJDAFKRUWQAH-GRDNDAEWSA-N 0.000 claims 1
• BXFVCKWLQHOSTC-FQNRMIAFSA-N (2r)-2-amino-3-(4-fluorophenyl)-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CSC(C=12)C)C1=CC=C(F)C=C1 BXFVCKWLQHOSTC-FQNRMIAFSA-N 0.000 claims 1
• BXFVCKWLQHOSTC-CZUORRHYSA-N (2r)-2-amino-3-(4-fluorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CS[C@@H](C=12)C)C1=CC=C(F)C=C1 BXFVCKWLQHOSTC-CZUORRHYSA-N 0.000 claims 1
• BXFVCKWLQHOSTC-XJKSGUPXSA-N (2r)-2-amino-3-(4-fluorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound C([C@@H](N)C(=O)N1CCN(CC1)C=1N=CN=C2CS[C@H](C=12)C)C1=CC=C(F)C=C1 BXFVCKWLQHOSTC-XJKSGUPXSA-N 0.000 claims 1
• AOOKIUGNQXTYRG-MAUKXSAKSA-N (2r)-4-amino-2-(4-chlorophenyl)-4-methyl-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound C1([C@@H](CC(C)(C)N)C(=O)N2CCN(CC2)C=2N=CN=C3CS[C@H](C=23)C)=CC=C(Cl)C=C1 AOOKIUGNQXTYRG-MAUKXSAKSA-N 0.000 claims 1
• QJCNXDZONNGTKP-QFBILLFUSA-N (2s)-2-(4-chlorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-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)SCC=3N=CN=2)CNC(C)C)=CC=C(Cl)C=C1 QJCNXDZONNGTKP-QFBILLFUSA-N 0.000 claims 1
• AOOKIUGNQXTYRG-YJBOKZPZSA-N (2s)-4-amino-2-(4-chlorophenyl)-4-methyl-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound C1([C@H](CC(C)(C)N)C(=O)N2CCN(CC2)C=2N=CN=C3CS[C@H](C=23)C)=CC=C(Cl)C=C1 AOOKIUGNQXTYRG-YJBOKZPZSA-N 0.000 claims 1
• PIYWXXWFNBIJSO-LROBGIAVSA-N 1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-2-(4-methylphenyl)-3-(propan-2-ylamino)propan-1-one Chemical compound C1CN(C=2C=3[C@H](C)SCC=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(C)C=C1 PIYWXXWFNBIJSO-LROBGIAVSA-N 0.000 claims 1
• AVTHZIOVAZSFMQ-MJTSIZKDSA-N 2-(1-aminocyclopropyl)-2-(4-chlorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(C1(N)CC1)C1=CC=C(Cl)C=C1 AVTHZIOVAZSFMQ-MJTSIZKDSA-N 0.000 claims 1
• AVTHZIOVAZSFMQ-KTQQKIMGSA-N 2-(1-aminocyclopropyl)-2-(4-chlorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]ethanone Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(C1(N)CC1)C1=CC=C(Cl)C=C1 AVTHZIOVAZSFMQ-KTQQKIMGSA-N 0.000 claims 1
• RRVNJKCGFWBUAU-UHFFFAOYSA-N 2-(1-aminocyclopropyl)-3-(4-chlorophenyl)-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C=12C(C)SCC2=NC=NC=1N(CC1)CCN1C(=O)C(C1(N)CC1)CC1=CC=C(Cl)C=C1 RRVNJKCGFWBUAU-UHFFFAOYSA-N 0.000 claims 1
• RRVNJKCGFWBUAU-NNJIEVJOSA-N 2-(1-aminocyclopropyl)-3-(4-chlorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(C1(N)CC1)CC1=CC=C(Cl)C=C1 RRVNJKCGFWBUAU-NNJIEVJOSA-N 0.000 claims 1
• RRVNJKCGFWBUAU-BUSXIPJBSA-N 2-(1-aminocyclopropyl)-3-(4-chlorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(C1(N)CC1)CC1=CC=C(Cl)C=C1 RRVNJKCGFWBUAU-BUSXIPJBSA-N 0.000 claims 1
• WJWVGEBEBBUJCK-MYJWUSKBSA-N 2-(3,4-difluorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C1CN(C=2C=3[C@H](C)SCC=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(F)C(F)=C1 WJWVGEBEBBUJCK-MYJWUSKBSA-N 0.000 claims 1
• PRAFBUAWROGPTB-MYJWUSKBSA-N 2-(4-chloro-3-fluorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C1CN(C=2C=3[C@H](C)SCC=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(Cl)C(F)=C1 PRAFBUAWROGPTB-MYJWUSKBSA-N 0.000 claims 1
• LIYZCWAXFVTFDF-QJNHQHDKSA-N 2-(4-chlorophenyl)-1-[(3s)-3-methyl-4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C([C@H](C)N(CC1)C=2C=3[C@@H](C)SCC=3N=CN=2)N1C(=O)C(CNC(C)C)C1=CC=C(Cl)C=C1 LIYZCWAXFVTFDF-QJNHQHDKSA-N 0.000 claims 1
• GOTDPFHEBCLFQR-GARIHTGFSA-N 2-(4-chlorophenyl)-1-[(3s)-3-methyl-4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-pyrrolidin-1-ylpropan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N([C@H](C1)C)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CCCC1 GOTDPFHEBCLFQR-GARIHTGFSA-N 0.000 claims 1
• LIYZCWAXFVTFDF-NBJLRHFZSA-N 2-(4-chlorophenyl)-1-[(3s)-3-methyl-4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C([C@H](C)N(CC1)C=2C=3[C@H](C)SCC=3N=CN=2)N1C(=O)C(CNC(C)C)C1=CC=C(Cl)C=C1 LIYZCWAXFVTFDF-NBJLRHFZSA-N 0.000 claims 1
• QJCNXDZONNGTKP-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C1CN(C=2C=3C(C)SCC=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(Cl)C=C1 QJCNXDZONNGTKP-UHFFFAOYSA-N 0.000 claims 1
• XJNIFPCRJRIHDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]-3-pyrrolidin-1-ylpropan-1-one Chemical compound C=12C(C)SCC2=NC=NC=1N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CCCC1 XJNIFPCRJRIHDJ-UHFFFAOYSA-N 0.000 claims 1
• QJCNXDZONNGTKP-VTBWFHPJSA-N 2-(4-chlorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C1CN(C=2C=3[C@@H](C)SCC=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(Cl)C=C1 QJCNXDZONNGTKP-VTBWFHPJSA-N 0.000 claims 1
• XJNIFPCRJRIHDJ-DIAVIDTQSA-N 2-(4-chlorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-pyrrolidin-1-ylpropan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CCCC1 XJNIFPCRJRIHDJ-DIAVIDTQSA-N 0.000 claims 1
• QJCNXDZONNGTKP-UCFFOFKASA-N 2-(4-chlorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C1CN(C=2C=3[C@H](C)SCC=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(Cl)C=C1 QJCNXDZONNGTKP-UCFFOFKASA-N 0.000 claims 1
• XJNIFPCRJRIHDJ-DIMJTDRSSA-N 2-(4-chlorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-pyrrolidin-1-ylpropan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CN1CCCC1 XJNIFPCRJRIHDJ-DIMJTDRSSA-N 0.000 claims 1
• YCUZVWTUODUCKK-QLIWTEFASA-N 2-(4-chlorophenyl)-3-(2-methylaziridin-1-yl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound CC1CN1CC(C=1C=CC(Cl)=CC=1)C(=O)N1CCN(C=2C=3[C@H](C)SCC=3N=CN=2)CC1 YCUZVWTUODUCKK-QLIWTEFASA-N 0.000 claims 1
• PCTCWPXLRGTAKG-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-[1-(dimethylamino)cyclopropyl]-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C=12C(C)SCC2=NC=NC=1N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CC1(N(C)C)CC1 PCTCWPXLRGTAKG-UHFFFAOYSA-N 0.000 claims 1
• GRLMEBDHSXBRAB-UCFFOFKASA-N 2-(4-fluorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]-3-(propan-2-ylamino)propan-1-one Chemical compound C1CN(C=2C=3[C@H](C)SCC=3N=CN=2)CCN1C(=O)C(CNC(C)C)C1=CC=C(F)C=C1 GRLMEBDHSXBRAB-UCFFOFKASA-N 0.000 claims 1
• LNZUHSPFFJBYER-IURRXHLWSA-N 3-(1-aminocyclopropyl)-2-(4-chloro-3-fluorophenyl)-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(C=1C=C(F)C(Cl)=CC=1)CC1(N)CC1 LNZUHSPFFJBYER-IURRXHLWSA-N 0.000 claims 1
• LNZUHSPFFJBYER-LBAUFKAWSA-N 3-(1-aminocyclopropyl)-2-(4-chloro-3-fluorophenyl)-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]propan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(C=1C=C(F)C(Cl)=CC=1)CC1(N)CC1 LNZUHSPFFJBYER-LBAUFKAWSA-N 0.000 claims 1
• NKHMIVSITJLBHY-UHFFFAOYSA-N 3-(1-aminocyclopropyl)-2-(4-chlorophenyl)-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]propan-1-one Chemical compound C=12C(C)SCC2=NC=NC=1N(CC1)CCN1C(=O)C(C=1C=CC(Cl)=CC=1)CC1(N)CC1 NKHMIVSITJLBHY-UHFFFAOYSA-N 0.000 claims 1
• WCUOKGLUDVLIGP-IURRXHLWSA-N 4-amino-2-(3,4-difluorophenyl)-4-methyl-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(F)C(F)=C1 WCUOKGLUDVLIGP-IURRXHLWSA-N 0.000 claims 1
• WCUOKGLUDVLIGP-LBAUFKAWSA-N 4-amino-2-(3,4-difluorophenyl)-4-methyl-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(F)C(F)=C1 WCUOKGLUDVLIGP-LBAUFKAWSA-N 0.000 claims 1
• FSOPFMNQEIQWFY-BTPDTDQASA-N 4-amino-2-(4-chloro-3-fluorophenyl)-4-methyl-1-[(3s)-3-methyl-4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N([C@H](C1)C)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C(F)=C1 FSOPFMNQEIQWFY-BTPDTDQASA-N 0.000 claims 1
• FSOPFMNQEIQWFY-GIIGEWEBSA-N 4-amino-2-(4-chloro-3-fluorophenyl)-4-methyl-1-[(3s)-3-methyl-4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N([C@H](C1)C)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C(F)=C1 FSOPFMNQEIQWFY-GIIGEWEBSA-N 0.000 claims 1
• OTUSYDRIAYYOGK-IURRXHLWSA-N 4-amino-2-(4-chloro-3-fluorophenyl)-4-methyl-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C(F)=C1 OTUSYDRIAYYOGK-IURRXHLWSA-N 0.000 claims 1
• OTUSYDRIAYYOGK-LBAUFKAWSA-N 4-amino-2-(4-chloro-3-fluorophenyl)-4-methyl-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C(F)=C1 OTUSYDRIAYYOGK-LBAUFKAWSA-N 0.000 claims 1
• PJDOKURCDYAVHJ-GWFKTICUSA-N 4-amino-2-(4-chlorophenyl)-4-methyl-1-[(3s)-3-methyl-4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N([C@H](C1)C)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C=C1 PJDOKURCDYAVHJ-GWFKTICUSA-N 0.000 claims 1
• PJDOKURCDYAVHJ-NRAVZPKASA-N 4-amino-2-(4-chlorophenyl)-4-methyl-1-[(3s)-3-methyl-4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N([C@H](C1)C)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C=C1 PJDOKURCDYAVHJ-NRAVZPKASA-N 0.000 claims 1
• AOOKIUGNQXTYRG-UHFFFAOYSA-N 4-amino-2-(4-chlorophenyl)-4-methyl-1-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]pentan-1-one Chemical compound C=12C(C)SCC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C=C1 AOOKIUGNQXTYRG-UHFFFAOYSA-N 0.000 claims 1
• AOOKIUGNQXTYRG-NNJIEVJOSA-N 4-amino-2-(4-chlorophenyl)-4-methyl-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C=C1 AOOKIUGNQXTYRG-NNJIEVJOSA-N 0.000 claims 1
• AOOKIUGNQXTYRG-BUSXIPJBSA-N 4-amino-2-(4-chlorophenyl)-4-methyl-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(Cl)C=C1 AOOKIUGNQXTYRG-BUSXIPJBSA-N 0.000 claims 1
• HSQHZBYOTVDLTC-NNJIEVJOSA-N 4-amino-2-(4-fluorophenyl)-4-methyl-1-[4-[(5r)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(F)C=C1 HSQHZBYOTVDLTC-NNJIEVJOSA-N 0.000 claims 1
• HSQHZBYOTVDLTC-BUSXIPJBSA-N 4-amino-2-(4-fluorophenyl)-4-methyl-1-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]pentan-1-one Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C(CC(C)(C)N)C1=CC=C(F)C=C1 HSQHZBYOTVDLTC-BUSXIPJBSA-N 0.000 claims 1
• OPPRKARULCJHNN-UHFFFAOYSA-N [4-(3-chlorophenyl)piperidin-4-yl]-[4-(5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl]methanone Chemical compound C=12C(C)SCC2=NC=NC=1N(CC1)CCN1C(=O)C1(C=2C=C(Cl)C=CC=2)CCNCC1 OPPRKARULCJHNN-UHFFFAOYSA-N 0.000 claims 1
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• OPPRKARULCJHNN-INIZCTEOSA-N [4-(3-chlorophenyl)piperidin-4-yl]-[4-[(5s)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl]piperazin-1-yl]methanone Chemical compound S([C@H](C=12)C)CC2=NC=NC=1N(CC1)CCN1C(=O)C1(C=2C=C(Cl)C=CC=2)CCNCC1 OPPRKARULCJHNN-INIZCTEOSA-N 0.000 claims 1
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