JP6494624B2 - カゼインキナーゼ1d/e阻害剤としての置換された4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピラジン誘導体 - Google Patents
カゼインキナーゼ1d/e阻害剤としての置換された4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピラジン誘導体 Download PDFInfo
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- JP6494624B2 JP6494624B2 JP2016531646A JP2016531646A JP6494624B2 JP 6494624 B2 JP6494624 B2 JP 6494624B2 JP 2016531646 A JP2016531646 A JP 2016531646A JP 2016531646 A JP2016531646 A JP 2016531646A JP 6494624 B2 JP6494624 B2 JP 6494624B2
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- heterocyclyl
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- 0 *C(*)(C1(*)*)[n]2nc(*)c(C(N)=O)c2CN1C(N*)=O Chemical compound *C(*)(C1(*)*)[n]2nc(*)c(C(N)=O)c2CN1C(N*)=O 0.000 description 35
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- MOGLBIJQGBUELJ-UHFFFAOYSA-N NC(c1c(CN(CC2)C(NC(C3)(CC3(F)F)c(cc3)ccc3F)=O)[n]2nc1-c(cc1Cl)ccc1F)=O Chemical compound NC(c1c(CN(CC2)C(NC(C3)(CC3(F)F)c(cc3)ccc3F)=O)[n]2nc1-c(cc1Cl)ccc1F)=O MOGLBIJQGBUELJ-UHFFFAOYSA-N 0.000 description 1
- DMLREOZQFLQUNK-UHFFFAOYSA-N NC(c1c(CN(CC2)C(NC3(CCC3)C(F)F)=O)[n]2nc1-c(cc1Cl)ccc1F)=O Chemical compound NC(c1c(CN(CC2)C(NC3(CCC3)C(F)F)=O)[n]2nc1-c(cc1Cl)ccc1F)=O DMLREOZQFLQUNK-UHFFFAOYSA-N 0.000 description 1
- AJACRCHGTXEVJB-SAABIXHNSA-N NC(c1c(CN(CC2)C(N[C@H](C3)C[C@@H]3Oc(cc3)ccc3C#N)=O)[n]2nc1-c(cc1Cl)ccc1F)=O Chemical compound NC(c1c(CN(CC2)C(N[C@H](C3)C[C@@H]3Oc(cc3)ccc3C#N)=O)[n]2nc1-c(cc1Cl)ccc1F)=O AJACRCHGTXEVJB-SAABIXHNSA-N 0.000 description 1
- VUXKAUQPJSJCEU-JLOHTSLTSA-N NC(c1c(CN(CC2)C(N[C@H](CC3)C3C(F)F)=O)[n]2nc1-c(cc1Cl)ccc1F)=O Chemical compound NC(c1c(CN(CC2)C(N[C@H](CC3)C3C(F)F)=O)[n]2nc1-c(cc1Cl)ccc1F)=O VUXKAUQPJSJCEU-JLOHTSLTSA-N 0.000 description 1
- QVTYNXCZSDQXEH-UHFFFAOYSA-N NC(c1c(CN(CC2CO)C(Nc(cc3)ccc3C#N)=O)[n]2nc1-c1cccc(Cl)c1)=O Chemical compound NC(c1c(CN(CC2CO)C(Nc(cc3)ccc3C#N)=O)[n]2nc1-c1cccc(Cl)c1)=O QVTYNXCZSDQXEH-UHFFFAOYSA-N 0.000 description 1
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- RJOPIKAIDVYVMH-UHFFFAOYSA-N NC(c1c(CNCC2C(F)(F)F)[n]2nc1-c(cc1Cl)ccc1F)=O Chemical compound NC(c1c(CNCC2C(F)(F)F)[n]2nc1-c(cc1Cl)ccc1F)=O RJOPIKAIDVYVMH-UHFFFAOYSA-N 0.000 description 1
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- RIJJVGRDVFWSRI-CBLAIPOGSA-N OC([C@H](C1)C[C@H]1C1C=CC(F)=CC1)=O Chemical compound OC([C@H](C1)C[C@H]1C1C=CC(F)=CC1)=O RIJJVGRDVFWSRI-CBLAIPOGSA-N 0.000 description 1
- AMEKJSMYCSRKOR-UHFFFAOYSA-N OCC(CNC(c1c2)=O)[n]1nc2-c1cccc(Cl)c1 Chemical compound OCC(CNC(c1c2)=O)[n]1nc2-c1cccc(Cl)c1 AMEKJSMYCSRKOR-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/20—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361904116P | 2013-11-14 | 2013-11-14 | |
| US61/904,116 | 2013-11-14 | ||
| PCT/US2014/065594 WO2015073763A1 (en) | 2013-11-14 | 2014-11-14 | Substituted 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine derivatives as casein kinase 1 d/e inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016537369A JP2016537369A (ja) | 2016-12-01 |
| JP2016537369A5 JP2016537369A5 (enExample) | 2017-12-21 |
| JP6494624B2 true JP6494624B2 (ja) | 2019-04-03 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016531646A Expired - Fee Related JP6494624B2 (ja) | 2013-11-14 | 2014-11-14 | カゼインキナーゼ1d/e阻害剤としての置換された4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピラジン誘導体 |
| JP2016531020A Expired - Fee Related JP6494622B2 (ja) | 2013-11-14 | 2014-11-14 | カゼインキナーゼ1d/e阻害剤としての置換された4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピラジン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016531020A Expired - Fee Related JP6494622B2 (ja) | 2013-11-14 | 2014-11-14 | カゼインキナーゼ1d/e阻害剤としての置換された4,5,6,7−テトラヒドロピラゾロ[1,5−a]ピラジン誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US9598423B2 (enExample) |
| EP (2) | EP3068784B1 (enExample) |
| JP (2) | JP6494624B2 (enExample) |
| CN (2) | CN105916855B (enExample) |
| AR (1) | AR098414A1 (enExample) |
| ES (2) | ES2718218T3 (enExample) |
| TW (1) | TW201605859A (enExample) |
| UY (1) | UY35834A (enExample) |
| WO (2) | WO2015073767A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR098414A1 (es) | 2013-11-14 | 2016-05-26 | Bristol Myers Squibb Co | PIPERAZINAS DE PIRAZOLO SUSTITUIDO COMO INHIBIDORES DE CASEÍNA QUINASA 1 d/e |
| EP3112369A4 (en) * | 2014-02-27 | 2017-09-20 | The University of Tokyo | Fused pyrazole derivative having autotaxin inhibitory activity |
| MA41338B1 (fr) * | 2015-01-16 | 2019-07-31 | Hoffmann La Roche | Composés de pyrazine pour le traitement de maladies infectieuses |
| CA3017020C (en) | 2016-03-07 | 2024-01-16 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| WO2017156071A1 (en) | 2016-03-09 | 2017-09-14 | Blade Therapeutics, Inc. | Cyclic keto-amide compounds as calpain modulators and methods of production and use thereof |
| CN109153682B (zh) * | 2016-05-20 | 2021-05-25 | 豪夫迈·罗氏有限公司 | 用于治疗感染性疾病的具有氧、硫和氮连接基的新的吡嗪化合物 |
| US11292801B2 (en) | 2016-07-05 | 2022-04-05 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| WO2018011163A1 (en) * | 2016-07-14 | 2018-01-18 | F. Hoffmann-La Roche Ag | 6,7-dihydro-4h-pyrazolo[1,5-a]pyrazine and 6,7-dihydro-4h-triazolo[1,5-a]pyrazine compounds for the treatment of infectious diseases |
| BR112019006110A2 (pt) | 2016-09-28 | 2019-09-10 | Blade Therapeutics Inc | moduladores de calpaína e usos terapêuticos dos mesmos |
| TWI782056B (zh) * | 2017-07-14 | 2022-11-01 | 日商鹽野義製藥股份有限公司 | 具有mgat2抑制活性的縮合環衍生物 |
| US11247998B2 (en) | 2017-07-27 | 2022-02-15 | Jiangsu Hengrui Medicine Co., Ltd. | Piperazine heteroaryl derivative, preparation method therefor and use of same in medicine |
| AU2018326474B2 (en) | 2017-08-28 | 2024-07-25 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| DK3681885T3 (da) | 2017-09-15 | 2024-04-15 | Forma Therapeutics Inc | Tetrahydro-imidazo-quinolinsammensætninger som cbp/p300-inhibitorer |
| EP3704113B1 (en) | 2017-11-01 | 2023-10-11 | Bristol-Myers Squibb Company | Bridged bicyclic compounds as farnesoid x receptor modulators |
| US11058678B2 (en) | 2018-01-22 | 2021-07-13 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| WO2019191166A1 (en) * | 2018-03-29 | 2019-10-03 | Enanta Pharmaceuticals, Inc. | Hepatitis b antiviral agents |
| CN111518016B (zh) * | 2018-06-01 | 2022-02-25 | 厦门宝太生物科技股份有限公司 | 一种csf1r抑制剂中间体及其制备方法 |
| AU2019295790B2 (en) | 2018-06-29 | 2023-07-13 | Forma Therapeutics, Inc. | Inhibiting creb binding protein (CBP) |
| TW202024093A (zh) | 2018-09-21 | 2020-07-01 | 美商安塔製藥公司 | 作為抗病毒劑之官能化雜環 |
| EP3883570A4 (en) | 2018-11-21 | 2022-07-13 | Enanta Pharmaceuticals, Inc. | FUNCTIONALIZED HETEROCYCLES AS ANTIVIRAL AGENTS |
| JP7608166B2 (ja) | 2019-01-11 | 2025-01-06 | 塩野義製薬株式会社 | Mgat2阻害活性を有するジヒドロピラゾロピラジノン誘導体 |
| CN111484497B (zh) * | 2019-01-25 | 2021-07-02 | 江苏恒瑞医药股份有限公司 | 咪唑并[1,5-a]吡嗪类衍生物的可药用盐、晶型及其制备方法 |
| WO2020151746A1 (zh) * | 2019-01-25 | 2020-07-30 | 江苏恒瑞医药股份有限公司 | 1,2,3-三氮唑并[1,5-a]吡嗪类衍生物的晶型及其制备方法 |
| CN111484498B (zh) * | 2019-01-25 | 2021-05-14 | 江苏恒瑞医药股份有限公司 | 咪唑并[1,5-a]吡嗪类化合物的晶型及其制备方法 |
| WO2020161257A1 (en) | 2019-02-07 | 2020-08-13 | Bayer Aktiengesellschaft | 3-amino-2-[2-(acylamino)pyridin-4-yl]-1,5,6,7-tetrahydro-4h-pyrrolo[3,2-c]pyridin-4-one as csnk1 inhibitors |
| EP3937940A4 (en) | 2019-03-15 | 2022-12-21 | Forma Therapeutics, Inc. | Inhibiting cyclic amp-responsive element-binding protein (creb) |
| WO2020247444A1 (en) | 2019-06-03 | 2020-12-10 | Enanta Pharmaceuticals, Inc, | Hepatitis b antiviral agents |
| US11472808B2 (en) | 2019-06-04 | 2022-10-18 | Enanta Pharmaceuticals, Inc. | Substituted pyrrolo[1,2-c]pyrimidines as hepatitis B antiviral agents |
| WO2020247561A1 (en) | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc, | Hepatitis b antiviral agents |
| US11738019B2 (en) | 2019-07-11 | 2023-08-29 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| US11236108B2 (en) | 2019-09-17 | 2022-02-01 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
| WO2021188414A1 (en) | 2020-03-16 | 2021-09-23 | Enanta Pharmaceuticals, Inc. | Functionalized heterocyclic compounds as antiviral agents |
| CN114057745A (zh) * | 2020-07-29 | 2022-02-18 | 江苏恒瑞医药股份有限公司 | 一种三氮唑并[1,5-a]吡嗪制备方法及其应用 |
| US20230339970A1 (en) * | 2020-09-17 | 2023-10-26 | Janssen Pharmaceutica Nv | Casein kinase 1 delta modulators |
| US11801243B2 (en) | 2020-09-23 | 2023-10-31 | Forma Therapeutics, Inc. | Bromodomain inhibitors for androgen receptor-driven cancers |
| US11795168B2 (en) | 2020-09-23 | 2023-10-24 | Forma Therapeutics, Inc. | Inhibiting cyclic amp-responsive element-binding protein (CREB) binding protein (CBP) |
| TW202245772A (zh) * | 2021-02-04 | 2022-12-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 一種衣殼蛋白抑制劑的醫藥組成物及其製備方法 |
| WO2023147015A1 (en) * | 2022-01-27 | 2023-08-03 | The Broad Institute, Inc. | Substituted heterocyclic csnk1 inhibitors |
| EP4538275A1 (en) * | 2022-06-13 | 2025-04-16 | Shionogi & Co., Ltd | Crystal of dihydropyridinone derivative or solvate thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL160915A0 (en) * | 2001-09-19 | 2004-08-31 | Aventis Pharma Sa | Indolizines inhibiting kinase proteins |
| JP4691506B2 (ja) * | 2003-12-11 | 2011-06-01 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | カゼインキナーゼIεの阻害剤としての置換1H−ピロロ[3,2−b,3,2−c,及び2,3−c]ピリジン−2−カルボキシアミド及び関連類似物 |
| US20050222171A1 (en) | 2004-01-22 | 2005-10-06 | Guido Bold | Organic compounds |
| US20070155738A1 (en) | 2005-05-20 | 2007-07-05 | Alantos Pharmaceuticals, Inc. | Heterobicyclic metalloprotease inhibitors |
| CN101417999A (zh) | 2007-10-25 | 2009-04-29 | 上海恒瑞医药有限公司 | 哌嗪类衍生物,其制备方法及其在医药上的应用 |
| EP2085398A1 (en) | 2008-02-01 | 2009-08-05 | Merz Pharma GmbH & Co. KGaA | Pyrazolopyrimidines, a process for their preparation and their use as medicine |
| CN102223798A (zh) | 2008-09-24 | 2011-10-19 | 巴斯夫欧洲公司 | 用于防治无脊椎动物害虫的吡唑化合物 |
| CA2738429C (en) | 2008-09-26 | 2016-10-25 | Intellikine, Inc. | Heterocyclic kinase inhibitors |
| WO2010059836A1 (en) | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Substituted aza-bridged bicyclics for cardiovascular and cns disease |
| TW201035102A (en) | 2009-03-04 | 2010-10-01 | Gruenethal Gmbh | Sulfonylated tetrahydroazolopyrazines and their use as medicinal products |
| FR2960876B1 (fr) | 2010-06-03 | 2012-07-27 | Sanofi Aventis | Derives de 3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1h)-dicarboxamide leur preparation et leur application en therapeutique. |
| CN102372716A (zh) | 2010-08-09 | 2012-03-14 | 江苏恒瑞医药股份有限公司 | 酞嗪酮类衍生物、其制备方法及其在医药上的应用 |
| CA2826464C (en) | 2011-03-02 | 2020-07-28 | Lead Discovery Center Gmbh | Pharmaceutically active disubstituted triazine derivatives |
| AR098414A1 (es) | 2013-11-14 | 2016-05-26 | Bristol Myers Squibb Co | PIPERAZINAS DE PIRAZOLO SUSTITUIDO COMO INHIBIDORES DE CASEÍNA QUINASA 1 d/e |
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