JP5231410B2 - Ａｋｔプロテインキナーゼ阻害剤としてのジヒドロフロピリミジン - Google Patents
Ａｋｔプロテインキナーゼ阻害剤としてのジヒドロフロピリミジン Download PDFInfo
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- JP5231410B2 JP5231410B2 JP2009518629A JP2009518629A JP5231410B2 JP 5231410 B2 JP5231410 B2 JP 5231410B2 JP 2009518629 A JP2009518629 A JP 2009518629A JP 2009518629 A JP2009518629 A JP 2009518629A JP 5231410 B2 JP5231410 B2 JP 5231410B2
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- 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 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 254
- -1 resolved enantiomers Chemical class 0.000 claims abstract description 252
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 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 18
- 125000004429 atom Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
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- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000003386 piperidinyl group Chemical group 0.000 claims description 20
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 9
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- 229910052799 carbon Inorganic materials 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
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- 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
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- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
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Landscapes
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| ATE532789T1 (de) | 2006-07-06 | 2011-11-15 | Array Biopharma Inc | Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated 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 |
| WO2009006567A2 (en) * | 2007-07-05 | 2009-01-08 | 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 |
| WO2009089453A1 (en) | 2008-01-09 | 2009-07-16 | Array Biopharma Inc. | Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor |
| US8329709B2 (en) | 2008-01-09 | 2012-12-11 | Genentech, Inc. | 5H-cyclopenta[D]pyrimidines as AKT protein kinase inhibitors |
| EP2242757B1 (en) | 2008-01-09 | 2012-08-01 | Array Biopharma, Inc. | Pyrazolopyridines as kinase inhibitors |
| KR20110046514A (ko) | 2008-07-31 | 2011-05-04 | 제넨테크, 인크. | 피리미딘 화합물, 조성물 및 사용 방법 |
| US8288381B2 (en) | 2009-11-12 | 2012-10-16 | Genentech, Inc. | 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 |
| CN113272304B (zh) | 2019-01-29 | 2024-03-29 | 南京正大天晴制药有限公司 | Akt抑制剂 |
| WO2021228223A1 (zh) * | 2020-05-15 | 2021-11-18 | 南京正大天晴制药有限公司 | 氘代akt激酶抑制剂 |
| CA3186568A1 (en) | 2020-07-22 | 2022-01-27 | Changyou MA | Salt of dihydropyrido[2,3-d]pyrimidinone derivative, preparation method therefor, and use thereof |
| US20230321108A1 (en) * | 2020-07-22 | 2023-10-12 | Nanjing Chia Tai Tianqing Pharmaceutical Co., Ltd. | Unit dosage composition of akt inhibitor |
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| US3885035A (en) | 1972-04-05 | 1975-05-20 | Sandoz Ag | Method for treating arrhythmia by using 1,4-bis(4 quinazolinyl) piperazines |
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| US3966936A (en) | 1974-02-21 | 1976-06-29 | Pfizer Inc. | Piperazino quinazoline bronchodilators |
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| JPS562968A (en) | 1979-06-21 | 1981-01-13 | Mitsubishi Yuka Yakuhin Kk | Novel pyrimidine derivative |
| US4749704A (en) | 1985-03-07 | 1988-06-07 | Sankyo Company Limited | Cyclopenta[d]pyrimidine derivatives and use as antidepressants |
| US4959368A (en) * | 1986-02-24 | 1990-09-25 | Mitsui Petrochemical Industries Ltd. | Therapeutic agent for neurological diseases |
| WO1990007926A1 (en) | 1989-01-20 | 1990-07-26 | Pfizer Inc. | 3-(1,2,5,6-tetrahydropyridyl)-pyrrolopyridines |
| PT664291E (pt) | 1992-10-05 | 2000-11-30 | Ube Industries | Composto de pirimidina |
| EP0710654A4 (en) | 1993-07-23 | 1996-08-28 | Green Cross Corp | TRIAZOLE DERIVATIVE AND ITS PHARMACEUTICAL USE |
| GB9416189D0 (en) | 1994-08-10 | 1994-09-28 | Merck Sharp & Dohme | Therapeutic agents |
| CN1102144C (zh) | 1994-08-13 | 2003-02-26 | 株式会社柳韩洋行 | 新的嘧啶衍生物及其制备方法 |
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| ZA979961B (en) | 1996-11-15 | 1999-05-05 | Lilly Co Eli | 5-HT1F agonists |
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| CA2290506C (en) | 1997-07-01 | 2005-12-27 | Warner-Lambert Company | 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as mek inhibitors |
| DE69836378T2 (de) | 1997-07-01 | 2007-10-11 | Warner-Lambert Co. Llc | Benzoesäure- und Benzamid-Derivate von Anthranilsäure und ihre Anwendung als MEK-Inhibitoren |
| US6506798B1 (en) | 1997-07-01 | 2003-01-14 | Warner-Lambert Company | 4-Arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective MEK inhibitors |
| US6821963B2 (en) | 1997-07-01 | 2004-11-23 | Warner-Lambert Company | 4-Bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as MEK inhibitors |
| US6310060B1 (en) | 1998-06-24 | 2001-10-30 | Warner-Lambert Company | 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as MEK inhibitors |
| CA2326324C (en) | 1998-03-31 | 2010-05-11 | Kyowa Hakko Kogyo Co., Ltd. | Nitrogen-containing heterocyclic compound |
| DE19853278A1 (de) | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| BR9916785A (pt) | 1999-01-07 | 2001-10-23 | Warner Lambert Co | Tratamento de asma com inibidores mek |
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- 2007-07-05 EP EP07799326A patent/EP2049546B1/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| US20110269773A1 (en) | 2011-11-03 |
| CN101511842A (zh) | 2009-08-19 |
| JP2009542720A (ja) | 2009-12-03 |
| WO2008006025A1 (en) | 2008-01-10 |
| ATE493418T1 (de) | 2011-01-15 |
| CA2656566C (en) | 2014-06-17 |
| EP2049546B1 (en) | 2010-12-29 |
| US8329701B2 (en) | 2012-12-11 |
| EP2049546A1 (en) | 2009-04-22 |
| CA2656566A1 (en) | 2008-01-10 |
| CN101511842B (zh) | 2012-10-31 |
| DE602007011628D1 (de) | 2011-02-10 |
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