JP2017513955A5 - - Google Patents
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- Publication number
- JP2017513955A5 JP2017513955A5 JP2017507914A JP2017507914A JP2017513955A5 JP 2017513955 A5 JP2017513955 A5 JP 2017513955A5 JP 2017507914 A JP2017507914 A JP 2017507914A JP 2017507914 A JP2017507914 A JP 2017507914A JP 2017513955 A5 JP2017513955 A5 JP 2017513955A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- purin
- dihydroxytetrahydrofuran
- alkyl
- amino
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 120
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 96
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 94
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 40
- 125000005843 halogen group Chemical group 0.000 claims 34
- 125000001424 substituent group Chemical group 0.000 claims 33
- 125000003118 aryl group Chemical group 0.000 claims 29
- 150000003839 salts Chemical class 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 23
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 19
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 16
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- -1 (Methylsulfonyl) methyl Chemical group 0.000 claims 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- QMCUISJHXICPLC-XNIJJKJLSA-N NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=C(C=CC=C1F)F)O)O Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=C(C=CC=C1F)F)O)O QMCUISJHXICPLC-XNIJJKJLSA-N 0.000 claims 2
- OGXXBFXUZNNBBS-UQAWHXBNSA-N O[C@@H]1[C@@H](COC(C(O)=O)C(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C(N[C@@H]3CCOC3)N=C(Cl)N=C12 Chemical compound O[C@@H]1[C@@H](COC(C(O)=O)C(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C(N[C@@H]3CCOC3)N=C(Cl)N=C12 OGXXBFXUZNNBBS-UQAWHXBNSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- OYYIRWXXCQBYJG-QLRVTQMJSA-N 2-[[(1R,2R,3S,4R)-4-(5-chloro-4-oxoquinazolin-3-yl)-2,3-dihydroxycyclopentyl]methoxy]-2-phosphonoacetic acid Chemical compound ClC1=C2C(N(C=NC2=CC=C1)[C@H]1[C@@H]([C@@H]([C@H](C1)COC(C(=O)O)P(=O)(O)O)O)O)=O OYYIRWXXCQBYJG-QLRVTQMJSA-N 0.000 claims 1
- NNACJYKNBNMOIB-FDGLDMCPSA-N 2-[[(2R,3S,4R,5R)-3,4-dihydroxy-5-[6-(4-hydroxypiperidin-1-yl)purin-9-yl]oxolan-2-yl]methoxy]-2-phosphonoacetic acid Chemical compound O[C@@H]1[C@H](O[C@H]([C@@H]1O)N1C2=NC=NC(=C2N=C1)N1CCC(CC1)O)COC(C(=O)O)P(=O)(O)O NNACJYKNBNMOIB-FDGLDMCPSA-N 0.000 claims 1
- KJEXWSKRPPXAMG-XNIJJKJLSA-N 2-[[(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy]-2-[(4-fluorophenyl)methyl]propanedioic acid Chemical compound NC1=C2N=CN(C2=NC(=N1)Cl)[C@H]1[C@@H]([C@@H]([C@H](O1)COC(C(=O)O)(C(=O)O)CC1=CC=C(C=C1)F)O)O KJEXWSKRPPXAMG-XNIJJKJLSA-N 0.000 claims 1
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- BFHYAOVYTYZXAQ-HEOLNDPQSA-N CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2N)P(O)(O)=O Chemical compound CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2N)P(O)(O)=O BFHYAOVYTYZXAQ-HEOLNDPQSA-N 0.000 claims 1
- MAWBBBBUAWAYIY-RIEBNTRSSA-N CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2NC1CCCC1)P(O)(O)=O Chemical compound CCOC(=O)C(OC[C@H]1C[C@H]([C@H](O)[C@@H]1O)N1N=NC2=C1N=C(Cl)N=C2NC1CCCC1)P(O)(O)=O MAWBBBBUAWAYIY-RIEBNTRSSA-N 0.000 claims 1
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- 229940127272 CD73 inhibitor Drugs 0.000 claims 1
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| US10167302B2 (en) * | 2014-05-23 | 2019-01-01 | University College Cork | Phosphonate nucleosides useful in the treatment of viral diseases |
| HUE050596T2 (hu) | 2014-11-21 | 2020-12-28 | Bristol Myers Squibb Co | Antitestek CD73 ellen és azok felhasználásai |
| HUE052526T2 (hu) | 2014-11-21 | 2021-05-28 | Bristol Myers Squibb Co | Antitestek, amelyek tartalmaznak módosított nehéz konstans régiókat |
| WO2017120508A1 (en) | 2016-01-08 | 2017-07-13 | Arcus Biosciences, Inc. | Modulators of 5'-nucleotidase, ecto and the use thereof |
| TW201811782A (zh) * | 2016-08-26 | 2018-04-01 | 日商田邊三菱製藥股份有限公司 | 二環式含氮雜環化合物 |
| US10472364B2 (en) | 2016-09-09 | 2019-11-12 | Calithera Biosciences, Inc. | Ectonucleotidase inhibitors and methods of use thereof |
| US11058704B2 (en) | 2016-10-03 | 2021-07-13 | Arcus Biosciences, Inc. | Inhibitors of adenosine 5′-nucleotidase |
| JP7150712B2 (ja) * | 2016-11-18 | 2022-10-11 | アーカス バイオサイエンシズ インコーポレイティド | Ｃｄ７３媒介免疫抑制の阻害剤 |
| EP3558998A4 (en) * | 2016-12-22 | 2020-06-10 | Calithera Biosciences, Inc. | ECTONUCLEOTIDASE INHIBITORS AND METHODS OF USE |
| EP3596124A1 (en) | 2017-03-16 | 2020-01-22 | Innate Pharma | Compositions and methods for treating cancer |
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| KR101841604B1 (ko) | 2017-04-26 | 2018-03-26 | 순천대학교 산학협력단 | 퍼푸린을 유효성분으로 포함하는 우울증 및 불안증의 예방 또는 치료용 조성물 |
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| EA039042B1 (ru) * | 2017-09-08 | 2021-11-25 | Калитера Байосайенсиз, Инк. | Ингибиторы эктонуклеотидазы и способы их применения |
| CN111542539B (zh) | 2017-10-06 | 2023-10-20 | 先天制药公司 | 通过cd39/cd73轴恢复t细胞活性 |
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| WO2019173682A1 (en) * | 2018-03-09 | 2019-09-12 | Arcus Biosciences, Inc. | Parenterally administered immune enhancing drugs |
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| CN112334486B (zh) | 2018-06-18 | 2025-02-18 | 先天制药公司 | 用于治疗癌症的组合物和方法 |
| BR112020025132B1 (pt) * | 2018-06-21 | 2023-10-10 | Antengene Therapeutics Limited | Inibidores de ectonucleotidase e métodos de uso dos mesmos |
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| US11332492B2 (en) | 2018-08-28 | 2022-05-17 | Jiangsu Hengrui Medicine Co., Ltd. | CD73 inhibitors and therapeutic uses thereof |
| US11530234B2 (en) | 2018-09-11 | 2022-12-20 | Risen (Suzhou) Pharma Tech Co., Ltd. | CD73 inhibitors and pharmaceutical uses thereof |
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| WO2020151707A1 (zh) * | 2019-01-22 | 2020-07-30 | 江苏恒瑞医药股份有限公司 | 一种新型的小分子cd73抑制剂、其制备方法及其在医药上的应用 |
| CN113795267A (zh) | 2019-03-12 | 2021-12-14 | 艾库斯生物科学有限公司 | 致癌基因驱动的癌症的治疗 |
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| CN113905743B (zh) * | 2019-03-29 | 2024-04-16 | 江苏恒瑞医药股份有限公司 | Cd73抑制剂及其治疗用途 |
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| CN114008048A (zh) * | 2019-06-20 | 2022-02-01 | 卡利泰拉生物科技公司 | 外核苷酸酶抑制剂及其使用方法 |
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| CN114867529B (zh) | 2019-10-09 | 2024-09-27 | 拜耳公司 | 作为农药的新的杂芳基三唑化合物 |
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| CN118576599A (zh) * | 2020-10-23 | 2024-09-03 | 和记黄埔医药（上海）有限公司 | 一种药物组合产品在制备用于治疗非小细胞肺癌的药物中的用途 |
| CN113549076B (zh) * | 2021-07-23 | 2022-12-06 | 中国药科大学 | 一种多取代嘌呤类化合物及其制备方法和应用 |
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| AU762749B2 (en) | 1998-07-01 | 2003-07-03 | Trustees Of The University Of Pennsylvania, The | Cavity induced allosteric modification of intermolecular interactions and methods of identifying compounds that effect the same |
| US20040043959A1 (en) * | 2002-03-04 | 2004-03-04 | Bloom Laura A. | Combination therapies for treating methylthioadenosine phosphorylase deficient cells |
| US7247621B2 (en) | 2002-04-30 | 2007-07-24 | Valeant Research & Development | Antiviral phosphonate compounds and methods therefor |
| US20090156545A1 (en) * | 2005-04-01 | 2009-06-18 | Hostetler Karl Y | Substituted Phosphate Esters of Nucleoside Phosphonates |
| EP1860113A1 (en) * | 2006-05-24 | 2007-11-28 | Rheinische Friedrich-Wilhelms-Universität Bonn | Ectonucleotidase inhibitors |
| US8956824B2 (en) | 2006-12-04 | 2015-02-17 | British Columbia Cancer Agency Branch | Methods for identifying allosteric modulators of ship polypeptides |
| WO2011131472A1 (en) | 2010-04-22 | 2011-10-27 | Institut Gustave Roussy | Compounds and uses thereof to induce an immunogenic cancer cell death in a subject |
| US8865653B2 (en) | 2010-04-22 | 2014-10-21 | Institut Gustave Roussy | Method of treatment for immunogenic treatment resistant cancer |
| WO2012031320A1 (en) | 2010-09-06 | 2012-03-15 | Peter Maccallum Cancer Institute | Cancer diagnostic |
| WO2014153424A1 (en) | 2013-03-19 | 2014-09-25 | La Jolla Institute For Allergy And Immunology | Reducing diabetes in patients receiving hmg-coa reductase inhibitors (statins) |
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