JP2009542720A5 - - Google Patents
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- JP2009542720A5 JP2009542720A5 JP2009518629A JP2009518629A JP2009542720A5 JP 2009542720 A5 JP2009542720 A5 JP 2009542720A5 JP 2009518629 A JP2009518629 A JP 2009518629A JP 2009518629 A JP2009518629 A JP 2009518629A JP 2009542720 A5 JP2009542720 A5 JP 2009542720A5
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- JP
- Japan
- Prior art keywords
- alkyl
- compound according
- cycloalkyl
- item
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 claims description 76
- -1 CH 2 F Chemical compound 0.000 claims description 69
- 125000004429 atom Chemical group 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 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 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims description 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 0 *C1OC(*)c2ncnc(N3C(*)CN(*)CC3)c12 Chemical compound *C1OC(*)c2ncnc(N3C(*)CN(*)CC3)c12 0.000 description 90
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 201000010099 disease Diseases 0.000 description 5
- YUIYTAHPRXTDGF-UHFFFAOYSA-N CC(C)(CC(C(C)=O)c(cc1)ccc1Cl)N Chemical compound CC(C)(CC(C(C)=O)c(cc1)ccc1Cl)N YUIYTAHPRXTDGF-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 230000001404 mediated effect Effects 0.000 description 4
- DASHHCMDGVYWSH-LSLKUGRBSA-N CC(C(CN(CC1)C[C@H]1O)c(cc1)ccc1Cl)=O Chemical compound CC(C(CN(CC1)C[C@H]1O)c(cc1)ccc1Cl)=O DASHHCMDGVYWSH-LSLKUGRBSA-N 0.000 description 3
- PVPNMLQGACPPGM-UHFFFAOYSA-N CC(C(CN1CCCC1)c(cc1)ccc1Cl)=O Chemical compound CC(C(CN1CCCC1)c(cc1)ccc1Cl)=O PVPNMLQGACPPGM-UHFFFAOYSA-N 0.000 description 3
- XSHVROGZGRKCDZ-UHFFFAOYSA-N CC(C)NC(C1)C1(C[NH+](C)[O-])c(cc1)ccc1Cl Chemical compound CC(C)NC(C1)C1(C[NH+](C)[O-])c(cc1)ccc1Cl XSHVROGZGRKCDZ-UHFFFAOYSA-N 0.000 description 3
- VVOFMUSZUYTPOK-UHFFFAOYSA-N CC(C)NCC(C(C(C)=C)=O)(c(cc1)ccc1Cl)O Chemical compound CC(C)NCC(C(C(C)=C)=O)(c(cc1)ccc1Cl)O VVOFMUSZUYTPOK-UHFFFAOYSA-N 0.000 description 3
- KRSDAJKDGZOADN-UHFFFAOYSA-N CC(C)NCC(C(C)=O)c(cc1)ccc1F Chemical compound CC(C)NCC(C(C)=O)c(cc1)ccc1F KRSDAJKDGZOADN-UHFFFAOYSA-N 0.000 description 3
- XDLBGBLQVRNEJW-UHFFFAOYSA-N CC(C)NCC(C(N)=O)c(cc1)cc(F)c1F Chemical compound CC(C)NCC(C(N)=O)c(cc1)cc(F)c1F XDLBGBLQVRNEJW-UHFFFAOYSA-N 0.000 description 3
- DNAQFEUBMBDVSR-UHFFFAOYSA-N CC(C)NCC(C(N)=O)c(cc1)ccc1OC Chemical compound CC(C)NCC(C(N)=O)c(cc1)ccc1OC DNAQFEUBMBDVSR-UHFFFAOYSA-N 0.000 description 3
- MGFXAHFTLAKBRH-UHFFFAOYSA-N CC(C)NCC(C(N1CC1)=O)c(cc1)c(C)c(F)c1Cl Chemical compound CC(C)NCC(C(N1CC1)=O)c(cc1)c(C)c(F)c1Cl MGFXAHFTLAKBRH-UHFFFAOYSA-N 0.000 description 3
- GXTRJCYTCAROAS-UHFFFAOYSA-N CC(C)NCC(C(N1CC1)=O)c(cc1)ccc1Cl Chemical compound CC(C)NCC(C(N1CC1)=O)c(cc1)ccc1Cl GXTRJCYTCAROAS-UHFFFAOYSA-N 0.000 description 3
- DEXDQYQZKYQAQF-UHFFFAOYSA-N NC(C(CN(CC1)CCC1O)c(cc1)ccc1Cl)=O Chemical compound NC(C(CN(CC1)CCC1O)c(cc1)ccc1Cl)=O DEXDQYQZKYQAQF-UHFFFAOYSA-N 0.000 description 3
- 125000002393 azetidinyl group Chemical group 0.000 description 3
- XMNHYTVFSORYKH-UHFFFAOYSA-N CC(C(CC1(CC1)N(C)C)c(cc1)ccc1Cl)=O Chemical compound CC(C(CC1(CC1)N(C)C)c(cc1)ccc1Cl)=O XMNHYTVFSORYKH-UHFFFAOYSA-N 0.000 description 2
- AFNNDFNFOMRPSI-UHFFFAOYSA-N CC(C(CC1(CC1)N)c(cc1)ccc1Cl)=O Chemical compound CC(C(CC1(CC1)N)c(cc1)ccc1Cl)=O AFNNDFNFOMRPSI-UHFFFAOYSA-N 0.000 description 2
- CHIKWHCJOJMBFW-UHFFFAOYSA-N CC(C(CCN)c(cc1)ccc1Br)=O Chemical compound CC(C(CCN)c(cc1)ccc1Br)=O CHIKWHCJOJMBFW-UHFFFAOYSA-N 0.000 description 2
- FVNZUMZSHCJXOG-UHFFFAOYSA-N CC(C(Cc(cc1)ccc1Cl)C1(CC1)N)=O Chemical compound CC(C(Cc(cc1)ccc1Cl)C1(CC1)N)=O FVNZUMZSHCJXOG-UHFFFAOYSA-N 0.000 description 2
- GAFQXOOPISZEIU-UHFFFAOYSA-N CC(C)(CC(C(C)=O)c(cc1)ccc1F)N Chemical compound CC(C)(CC(C(C)=O)c(cc1)ccc1F)N GAFQXOOPISZEIU-UHFFFAOYSA-N 0.000 description 2
- CAICXYBBTBZAKS-UHFFFAOYSA-N CC(C)NCC(C(N(CC1)CCN1c1ncnc2c1C(C)OC2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NCC(C(N(CC1)CCN1c1ncnc2c1C(C)OC2)=O)c(cc1)ccc1Cl CAICXYBBTBZAKS-UHFFFAOYSA-N 0.000 description 2
- FGTBJDQJHUFZSB-UHFFFAOYSA-N CC(C1(CCNCC1)c(cc1)cc(F)c1Cl)=O Chemical compound CC(C1(CCNCC1)c(cc1)cc(F)c1Cl)=O FGTBJDQJHUFZSB-UHFFFAOYSA-N 0.000 description 2
- PRFRVPSGJHHMHG-UHFFFAOYSA-N CC(C1(CCNCC1)c(cc1)ccc1Cl)=O Chemical compound CC(C1(CCNCC1)c(cc1)ccc1Cl)=O PRFRVPSGJHHMHG-UHFFFAOYSA-N 0.000 description 2
- AFOVYKKGSJUFQA-UHFFFAOYSA-N CC(CCN)(C(NC)=O)c(cc1)ccc1Cl Chemical compound CC(CCN)(C(NC)=O)c(cc1)ccc1Cl AFOVYKKGSJUFQA-UHFFFAOYSA-N 0.000 description 2
- PIPMENIKBUTGQR-SNVBAGLBSA-N CC([C@@H](Cc(cc1)ccc1F)N)=O Chemical compound CC([C@@H](Cc(cc1)ccc1F)N)=O PIPMENIKBUTGQR-SNVBAGLBSA-N 0.000 description 2
- UKWPYCHZAPELGS-LLVKDONJSA-N CC([C@@H](Cc(cc1)ccc1OC)N)=O Chemical compound CC([C@@H](Cc(cc1)ccc1OC)N)=O UKWPYCHZAPELGS-LLVKDONJSA-N 0.000 description 2
- SANCTMWYECMLCR-UHFFFAOYSA-N CC1OCc2c1c(N(CC1)CCN1C(C(CC(C)(C)N)c(cc1F)ccc1Cl)=O)ncn2 Chemical compound CC1OCc2c1c(N(CC1)CCN1C(C(CC(C)(C)N)c(cc1F)ccc1Cl)=O)ncn2 SANCTMWYECMLCR-UHFFFAOYSA-N 0.000 description 2
- RBXFUWLZNZOTBN-UHFFFAOYSA-O CCC(C(CC(C)(C)[NH3+])c(cc1)cc(F)c1Cl)=O Chemical compound CCC(C(CC(C)(C)[NH3+])c(cc1)cc(F)c1Cl)=O RBXFUWLZNZOTBN-UHFFFAOYSA-O 0.000 description 2
- RIGDNGRCTWXWFW-MRJYIUEKSA-N CCC(C(CN[C@H](CC1)CC[C@@H]1O)c(cc1)ccc1Cl)=O Chemical compound CCC(C(CN[C@H](CC1)CC[C@@H]1O)c(cc1)ccc1Cl)=O RIGDNGRCTWXWFW-MRJYIUEKSA-N 0.000 description 2
- PNXREAUYPTXQHE-MRVPVSSYSA-N CCC([C@H](CN)c(cc1)cc(Cl)c1Cl)=O Chemical compound CCC([C@H](CN)c(cc1)cc(Cl)c1Cl)=O PNXREAUYPTXQHE-MRVPVSSYSA-N 0.000 description 2
- QPILAAUEILBAAN-VHSXEESVSA-N CCC([C@H](CNC1)[C@@H]1c(cc1)cc(Cl)c1Cl)=O Chemical compound CCC([C@H](CNC1)[C@@H]1c(cc1)cc(Cl)c1Cl)=O QPILAAUEILBAAN-VHSXEESVSA-N 0.000 description 2
- ROQQOZZRWJKYNO-TVKKRMFBSA-N CCCC([C@@H](CC1c2ccccc2NC1)N)=O Chemical compound CCCC([C@@H](CC1c2ccccc2NC1)N)=O ROQQOZZRWJKYNO-TVKKRMFBSA-N 0.000 description 2
- BIJHQFODGCREMQ-UHFFFAOYSA-N CNCC(C(CCN)=O)c(cc1)ccc1F Chemical compound CNCC(C(CCN)=O)c(cc1)ccc1F BIJHQFODGCREMQ-UHFFFAOYSA-N 0.000 description 2
- RUPAHVODHKPLTA-YCQNMSHMSA-N C[C@H]([C@@H](C)NCC(C(CN)=O)c(cc1)ccc1Cl)c1ccccc1 Chemical compound C[C@H]([C@@H](C)NCC(C(CN)=O)c(cc1)ccc1Cl)c1ccccc1 RUPAHVODHKPLTA-YCQNMSHMSA-N 0.000 description 2
- LBASRDAUCBGBOV-LHIURRSHSA-N NCCC([C@H](CN)C1C=CC(Cl)=CC1)=O Chemical compound NCCC([C@H](CN)C1C=CC(Cl)=CC1)=O LBASRDAUCBGBOV-LHIURRSHSA-N 0.000 description 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 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 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 description 2
- 239000012453 solvate Substances 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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| WO2008006039A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Dihydrothieno 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 |
| CA2692502C (en) * | 2007-07-05 | 2016-03-01 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| WO2009089352A1 (en) | 2008-01-08 | 2009-07-16 | Array Biopharma Inc. | Pyrrolopyridines as kinase inhibitors |
| US8853216B2 (en) | 2008-01-09 | 2014-10-07 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentane as AKT protein kinase inhibitor |
| CN104876921A (zh) | 2008-01-09 | 2015-09-02 | 阵列生物制药公司 | 作为AKT蛋白激酶抑制剂的5H-环戊二烯并[d]嘧啶 |
| EP2242757B1 (en) | 2008-01-09 | 2012-08-01 | Array Biopharma, Inc. | Pyrazolopyridines as kinase inhibitors |
| US8163763B2 (en) | 2008-07-31 | 2012-04-24 | Genentech, Inc. | Pyrimidine compounds, compositions and methods of use |
| WO2011058027A2 (en) | 2009-11-12 | 2011-05-19 | F. Hoffmann-La Roche Ag | N-9-substituted purine compounds, compositions and methods of use |
| ES2567168T3 (es) | 2009-11-12 | 2016-04-20 | F. Hoffmann-La Roche Ag | Compuestos purina y pirazolopirimidina N7-sustituidos, composiciones y métodos de utilización |
| AU2014293013A1 (en) | 2013-07-26 | 2016-03-17 | Race Oncology Ltd. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| US10722484B2 (en) | 2016-03-09 | 2020-07-28 | K-Gen, Inc. | Methods of cancer treatment |
| US12617784B2 (en) | 2019-01-29 | 2026-05-05 | Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. | AKT inhibitor |
| CN115485276B (zh) * | 2020-05-15 | 2024-05-31 | 南京正大天晴制药有限公司 | 氘代akt激酶抑制剂 |
| EP4186902A4 (en) | 2020-07-22 | 2024-06-05 | Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. | DIHYDROPYRIDO[2,3-D]PYRIMIDINONE DERIVATIVE SALT, PREPARATION METHOD AND USE THEREOF |
| US12673061B2 (en) | 2020-07-22 | 2026-07-07 | Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. | Unit dosage composition of AKT inhibitor |
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- 2007-07-05 WO PCT/US2007/072863 patent/WO2008006025A1/en not_active Ceased
- 2007-07-05 EP EP07799326A patent/EP2049546B1/en active Active
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