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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (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) | EP3068785B1 (enExample) |
| JP (2) | JP6494624B2 (enExample) |
| CN (2) | CN105916856B (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 |
| WO2015129821A1 (ja) | 2014-02-27 | 2015-09-03 | 国立大学法人東京大学 | オートタキシン阻害活性を有する縮合ピラゾール誘導体 |
| MA41338B1 (fr) * | 2015-01-16 | 2019-07-31 | Hoffmann La Roche | Composés de pyrazine pour le traitement de maladies infectieuses |
| EP3426245B1 (en) | 2016-03-07 | 2022-12-14 | 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 |
| EP3481835A4 (en) | 2016-07-05 | 2020-02-26 | Blade Therapeutics, Inc. | CALPAIN MODULATORS AND THEIR THERAPEUTIC USES |
| CN109476668B (zh) * | 2016-07-14 | 2022-03-22 | 豪夫迈·罗氏有限公司 | 用于治疗感染性疾病的6,7-二氢-4H-吡唑并[1,5-a]吡嗪和6,7-二氢-4H-三唑并[1,5-a]吡嗪化合物 |
| WO2018064119A1 (en) * | 2016-09-28 | 2018-04-05 | Blade Therapeutics, Inc. | Calpain modulators and therapeutic uses thereof |
| 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 |
| JP2020528062A (ja) * | 2017-07-27 | 2020-09-17 | 江蘇恒瑞医薬股▲ふん▼有限公司 | ピペラジンヘテロアリール誘導体、その製造方法、およびその医薬での使用 |
| AU2018326474B2 (en) | 2017-08-28 | 2024-07-25 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| TWI846350B (zh) | 2017-09-15 | 2024-06-21 | 美商佛瑪治療公司 | 作為CBP/p300抑制劑之四氫-咪唑並喹啉化合物 |
| AU2018360577A1 (en) | 2017-11-01 | 2020-06-18 | Bristol-Myers Squibb Company | Bridged bicyclic compounds as farnesoid X receptor modulators |
| WO2019143902A2 (en) | 2018-01-22 | 2019-07-25 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
| US10729688B2 (en) * | 2018-03-29 | 2020-08-04 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
| US11591328B2 (en) * | 2018-06-01 | 2023-02-28 | Xiamen Biotime Biotechnology Co., Ltd. | Highly active CSF1R inhibitor compound |
| KR102805503B1 (ko) | 2018-06-29 | 2025-05-09 | 포르마 세라퓨틱스 인크. | Creb 결합 단백질(cbp)의 저해 |
| AR116474A1 (es) | 2018-09-21 | 2021-05-12 | Enanta Pharm Inc | DERIVADOS DEL ÁCIDO 6,7-DIHIDRO-2H-BENZOFURO[2,3-a]QUINOLIZIN-3-CARBOXÍLICO COMO AGENTES ANTIVIRALES PARA EL TRATAMIENTO O PREVENCIÓN DE UNA INFECCIÓN POR HBV |
| BR112021009854A2 (pt) | 2018-11-21 | 2021-08-17 | Enanta Pharmaceuticals, Inc. | heterociclos funcionalizados como agentes antivirais |
| EP3909583A4 (en) | 2019-01-11 | 2022-08-17 | Shionogi & Co., Ltd | DIHYDROPYRAZOLOPYRAZINONE DERIVATIVES WITH MGAT2 INHIBITORY ACTIVITY |
| TW202043233A (zh) * | 2019-01-25 | 2020-12-01 | 大陸商江蘇恒瑞醫藥股份有限公司 | 1,2,3-三氮唑并[1,5-a]吡類衍生物的晶型及其製備方法 |
| 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 |
| 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 |
| CA3128946A1 (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 |
| WO2020190791A1 (en) | 2019-03-15 | 2020-09-24 | 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 |
| WO2020247561A1 (en) | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc, | Hepatitis b antiviral agents |
| WO2020247575A1 (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 |
| WO2021055425A2 (en) | 2019-09-17 | 2021-03-25 | Enanta Pharmaceuticals, Inc. | Functionalized heterocycles as antiviral agents |
| US11802125B2 (en) | 2020-03-16 | 2023-10-31 | 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 |
| AU2021342792A1 (en) * | 2020-09-17 | 2023-06-01 | 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) |
| WO2022166778A1 (zh) * | 2021-02-04 | 2022-08-11 | 江苏恒瑞医药股份有限公司 | 一种衣壳蛋白抑制剂的药物组合物及其制备方法 |
| EP4469457A1 (en) * | 2022-01-27 | 2024-12-04 | The Broad Institute Inc. | Substituted heterocyclic csnk1 inhibitors |
| KR20250022711A (ko) * | 2022-06-13 | 2025-02-17 | 시오노기 앤드 컴파니, 리미티드 | 다이하이드로피리딘온 유도체 또는 그 용매화물의 결정 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04002243A (es) * | 2001-09-19 | 2004-06-29 | Aventis Pharma Sa | Compuestos quimicos. |
| ATE428711T1 (de) * | 2003-12-11 | 2009-05-15 | Aventis Pharma Inc | Substituierte 1h-pyrroloä3,2-b, 3,2-c und 2,3- cüpyridin-2-carbonsäureamide und verwandte analoga als inhibitoren von caseinkinase-i- epsilon |
| 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 |
| JP2012503623A (ja) | 2008-09-24 | 2012-02-09 | ビーエーエスエフ ソシエタス・ヨーロピア | 無脊椎動物系害虫防除用ピラゾール化合物 |
| US8703778B2 (en) | 2008-09-26 | 2014-04-22 | Intellikine Llc | 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 |
| US9226929B2 (en) | 2011-03-02 | 2016-01-05 | Bayer Intellectual Property 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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