JP5231411B2 - Ａｋｔプロテインキナーゼ阻害剤としてのジヒドロチエノピリミジン - Google Patents
Ａｋｔプロテインキナーゼ阻害剤としてのジヒドロチエノピリミジン Download PDFInfo
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- JP5231411B2 JP5231411B2 JP2009518635A JP2009518635A JP5231411B2 JP 5231411 B2 JP5231411 B2 JP 5231411B2 JP 2009518635 A JP2009518635 A JP 2009518635A JP 2009518635 A JP2009518635 A JP 2009518635A JP 5231411 B2 JP5231411 B2 JP 5231411B2
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- methyl
- alkyl
- chlorophenyl
- dihydrothieno
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- 108091008611 Protein Kinase B Proteins 0.000 title abstract description 55
- 102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 title abstract description 37
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract 2
- 239000003909 protein kinase inhibitor Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 294
- -1 resolved enantiomers Chemical class 0.000 claims abstract description 289
- 150000003839 salts Chemical class 0.000 claims abstract description 50
- 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 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
- 125000004429 atom Chemical group 0.000 claims description 43
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 27
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000003386 piperidinyl group Chemical group 0.000 claims description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000003566 oxetanyl group Chemical group 0.000 claims description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 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 4
- 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 4
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims description 4
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 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 1
- 238000000034 method Methods 0.000 abstract description 77
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- 230000003463 hyperproliferative effect Effects 0.000 abstract description 8
- 239000012453 solvate Substances 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 237
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 171
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 42
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 34
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 28
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
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Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
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- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Vascular Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
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| US81895206P | 2006-07-06 | 2006-07-06 | |
| US60/818,952 | 2006-07-06 | ||
| PCT/US2007/072884 WO2008006039A1 (en) | 2006-07-06 | 2007-07-05 | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
Publications (3)
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| JP2009542722A JP2009542722A (ja) | 2009-12-03 |
| JP2009542722A5 JP2009542722A5 (enExample) | 2011-08-11 |
| JP5231411B2 true JP5231411B2 (ja) | 2013-07-10 |
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| US (1) | US9303040B2 (enExample) |
| EP (1) | EP2054418B1 (enExample) |
| JP (1) | JP5231411B2 (enExample) |
| CN (1) | CN101516891B (enExample) |
| AT (1) | ATE532789T1 (enExample) |
| CA (1) | CA2656364C (enExample) |
| DK (1) | DK2054418T3 (enExample) |
| SI (1) | SI2054418T1 (enExample) |
| WO (1) | WO2008006039A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US10751842B2 (en) | 2014-10-10 | 2020-08-25 | Kosmek Ltd. | Output device |
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| ATE532789T1 (de) * | 2006-07-06 | 2011-11-15 | Array Biopharma Inc | Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren |
| US8329701B2 (en) * | 2006-07-06 | 2012-12-11 | Array Biopharma Inc. | Dihydrofuro pyrimidines as AKT protein kinase inhibitors |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| UA95641C2 (xx) * | 2006-07-06 | 2011-08-25 | Эррей Биофарма Инк. | Гідроксильовані піримідильні циклопентани як інгібітори акт протеїнкінази$гидроксилированные пиримидильные циклопентаны как ингибиторы акт протеинкиназы |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | 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 |
| WO2009089352A1 (en) | 2008-01-08 | 2009-07-16 | Array Biopharma Inc. | Pyrrolopyridines as kinase inhibitors |
| EP2240455B1 (en) | 2008-01-09 | 2012-12-26 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor |
| US8372842B2 (en) | 2008-01-09 | 2013-02-12 | Array Biopharma Inc. | Pyrazolopyridines as kinase inhibitors |
| ES2426092T3 (es) | 2008-01-09 | 2013-10-21 | Array Biopharma, Inc. | 5H-Ciclopenta[d]pirimidinas como inhibidores de proteínas cinasas AKT |
| DE102010025663A1 (de) * | 2010-06-30 | 2012-01-05 | Karl-Heinz Glüsenkamp | Neue beta-Aminoaldehyd-Derivate, Verfahren zu ihrer Herstellung und ihre chemische Verwendung als reaktive Intermediate |
| SG10201504303SA (en) | 2011-04-01 | 2015-07-30 | Genentech Inc | Combinations Of AKT Inhibitor Compounds And Chemotherapeutic Agents, And Methods Of Use |
| TR201815685T4 (tr) | 2011-04-01 | 2018-11-21 | Genentech Inc | Kanser tedavisi için akt ve mek inhibe edici bileşiklerin kombinasyonları. |
| WO2014195276A1 (en) * | 2013-06-07 | 2014-12-11 | Bayer Pharma Aktiengesellschaft | Substituted triazolopyridines having activity as mps-1 inhibitors |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| CN113087718B (zh) * | 2020-01-09 | 2024-02-09 | 四川科伦博泰生物医药股份有限公司 | 噻吩并嘧啶酮类化合物及其医药应用 |
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2007
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- 2007-07-05 CA CA2656364A patent/CA2656364C/en active Active
- 2007-07-05 CN CN2007800330584A patent/CN101516891B/zh active Active
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- 2007-07-05 WO PCT/US2007/072884 patent/WO2008006039A1/en not_active Ceased
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10751842B2 (en) | 2014-10-10 | 2020-08-25 | Kosmek Ltd. | Output device |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2656364A1 (en) | 2008-01-10 |
| EP2054418B1 (en) | 2011-11-09 |
| WO2008006039A1 (en) | 2008-01-10 |
| EP2054418A1 (en) | 2009-05-06 |
| DK2054418T3 (da) | 2012-02-27 |
| US9303040B2 (en) | 2016-04-05 |
| ATE532789T1 (de) | 2011-11-15 |
| CN101516891B (zh) | 2013-06-05 |
| SI2054418T1 (sl) | 2012-02-29 |
| US20120329808A1 (en) | 2012-12-27 |
| JP2009542722A (ja) | 2009-12-03 |
| CN101516891A (zh) | 2009-08-26 |
| CA2656364C (en) | 2014-11-25 |
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