RU2015104123A - Производные пиримидинпиразолила - Google Patents
Производные пиримидинпиразолила Download PDFInfo
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- RU2015104123A RU2015104123A RU2015104123A RU2015104123A RU2015104123A RU 2015104123 A RU2015104123 A RU 2015104123A RU 2015104123 A RU2015104123 A RU 2015104123A RU 2015104123 A RU2015104123 A RU 2015104123A RU 2015104123 A RU2015104123 A RU 2015104123A
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- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract 5
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 2
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003003 spiro group Chemical group 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 150000004677 hydrates Chemical class 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- 208000002552 acute disseminated encephalomyelitis Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 208000026872 Addison Disease Diseases 0.000 claims 1
- 201000004384 Alopecia Diseases 0.000 claims 1
- 206010001935 American trypanosomiasis Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 208000024699 Chagas disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 208000007465 Giant cell arteritis Diseases 0.000 claims 1
- 208000024869 Goodpasture syndrome Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 208000003807 Graves Disease Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 208000001204 Hashimoto Disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 1
- 208000010159 IgA glomerulonephritis Diseases 0.000 claims 1
- 206010021263 IgA nephropathy Diseases 0.000 claims 1
- 102100036342 Interleukin-1 receptor-associated kinase 1 Human genes 0.000 claims 1
- 101710199015 Interleukin-1 receptor-associated kinase 1 Proteins 0.000 claims 1
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 1
- 208000000209 Isaacs syndrome Diseases 0.000 claims 1
- 208000011200 Kawasaki disease Diseases 0.000 claims 1
- 208000005777 Lupus Nephritis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010072359 Neuromyotonia Diseases 0.000 claims 1
- 206010034277 Pemphigoid Diseases 0.000 claims 1
- 241000721454 Pemphigus Species 0.000 claims 1
- 208000031845 Pernicious anaemia Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 206010072148 Stiff-Person syndrome Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims 1
- 241000223109 Trypanosoma cruzi Species 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 206010047642 Vitiligo Diseases 0.000 claims 1
- 230000003187 abdominal effect Effects 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 1
- 208000000594 bullous pemphigoid Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000001981 dermatomyositis Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 210000003027 ear inner Anatomy 0.000 claims 1
- 208000002557 hidradenitis Diseases 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 230000002018 overexpression Effects 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 206010043207 temporal arteritis Diseases 0.000 claims 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052727 yttrium Inorganic materials 0.000 abstract 1
- 0 CC1(C)C(B(O*)O*)=CN(*)N=C1 Chemical compound CC1(C)C(B(O*)O*)=CN(*)N=C1 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
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- 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
- C07D487/08—Bridged systems
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- 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
- C07D491/02—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 two hetero rings
- C07D491/08—Bridged systems
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- 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
- C07D491/02—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 two hetero rings
- C07D491/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D491/02—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 two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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| US61/669,843 | 2012-07-10 | ||
| PCT/EP2013/001950 WO2014008992A1 (en) | 2012-07-10 | 2013-07-03 | Pyrimidine pyrazolyl derivatives |
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| CN106068264B (zh) * | 2014-01-09 | 2019-06-21 | 默克专利有限公司 | 嘧啶吡唑基衍生物及其作为irak抑制剂的用途 |
| PL3129023T3 (pl) | 2014-03-27 | 2021-08-16 | Eicosis, Llc | Silne inhibitory rozpuszczalnej hydrolazy epoksydowej |
| PT3221306T (pt) | 2014-11-20 | 2020-02-19 | Merck Patent Gmbh | Compostos de heteroarilo como inibidores de irak e utilização dos mesmos |
| CN105153211B (zh) * | 2015-09-22 | 2017-02-01 | 上海晋鲁医药科技有限公司 | 一种合成1‑(N‑Boc‑4‑哌啶)‑4‑吡唑硼酸频哪醇酯的方法 |
| JP6947743B2 (ja) | 2016-03-03 | 2021-10-13 | バイエル・ファルマ・アクティエンゲゼルシャフト | 新規な２−置換インダゾール、その製造方法、それを含有する医薬製剤、および薬物を製造するためのその使用 |
| JOP20180011A1 (ar) | 2017-02-16 | 2019-01-30 | Gilead Sciences Inc | مشتقات بيرولو [1، 2-b]بيريدازين |
| US10894796B2 (en) | 2017-03-16 | 2021-01-19 | Celgene Car Llc | MK2 inhibitors, synthesis thereof, and intermediates thereto |
| CN106967073A (zh) * | 2017-04-24 | 2017-07-21 | 刘双伟 | 一种治疗类风湿性关节炎的药物 |
| CN106946891B (zh) * | 2017-05-08 | 2018-07-13 | 宿州市徽腾知识产权咨询有限公司 | 一种用于治疗类风湿性关节炎的药物 |
| AU2018338314B2 (en) | 2017-09-22 | 2024-12-12 | Kymera Therapeutics, Inc | Protein degraders and uses thereof |
| WO2019060693A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES THEREOF |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| EP3737675A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| EP3737666A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | PROTEIN DEGRADATION AGENTS AND ASSOCIATED USES |
| WO2020010227A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| EP3817748A4 (en) | 2018-07-06 | 2022-08-24 | Kymera Therapeutics, Inc. | TRICYCLIC CRBN LIGANDS AND USES THEREOF |
| TWI842978B (zh) | 2018-07-13 | 2024-05-21 | 美商基利科學股份有限公司 | 衍生物 |
| EP3870177A1 (en) * | 2018-10-26 | 2021-09-01 | Arrien Pharmaceuticals LLC | Pyrazolyl compounds and methods of use thereof |
| SG11202105424PA (en) | 2018-11-30 | 2021-06-29 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| EP4061821B1 (en) * | 2019-11-20 | 2025-08-06 | F. Hoffmann-La Roche AG | Spiro(isobenzofuranazetidine) compounds for the treatment of autoimmune disease |
| WO2021127283A2 (en) | 2019-12-17 | 2021-06-24 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| JP2023509366A (ja) | 2019-12-17 | 2023-03-08 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ分解剤およびそれらの使用 |
| CN110950839B (zh) * | 2019-12-17 | 2023-04-14 | 蚌埠中实化学技术有限公司 | 4-（4-卤代-1h-吡唑-1-基）哌啶-1-羧酸叔丁酯的制备方法 |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| MX2023007852A (es) | 2020-12-30 | 2023-07-07 | Kymera Therapeutics Inc | Degradadores de cinasas asociadas al receptor de interleucina-1 (irak) y usos de los mismos. |
| WO2022165148A1 (en) * | 2021-02-01 | 2022-08-04 | Celgene Corporation | Mk2 inhibitors, the synthesis thereof, and intermediates thereto |
| WO2022174268A1 (en) | 2021-02-15 | 2022-08-18 | Kymera Therapeutics, Inc. | Irak4 degraders and uses thereof |
| AU2022271290A1 (en) | 2021-05-07 | 2023-11-23 | Kymera Therapeutics, Inc. | Cdk2 degraders and uses thereof |
| WO2023076556A1 (en) | 2021-10-29 | 2023-05-04 | Kymera Therapeutics, Inc. | Irak4 degraders and synthesis thereof |
| IL314437A (en) | 2022-01-31 | 2024-09-01 | Kymera Therapeutics Inc | IRAK joints and their uses |
| EP4551218A2 (en) * | 2022-07-07 | 2025-05-14 | Dana-Farber Cancer Institute, Inc. | Potent and selective irreversible inhibitors of irak1 |
| CN115490621B (zh) * | 2022-10-14 | 2024-06-21 | 浙江工业大学 | 一种碘代双环[1.1.1]戊烷衍生物的制备方法 |
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| US5559137A (en) * | 1994-05-16 | 1996-09-24 | Smithkline Beecham Corp. | Compounds |
| CA2432131C (en) * | 2000-12-21 | 2008-07-08 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US7659270B2 (en) * | 2006-08-11 | 2010-02-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| DE102008025750A1 (de) * | 2008-05-29 | 2009-12-03 | Merck Patent Gmbh | Dihydropyrazolderivate |
| DE102008062825A1 (de) * | 2008-12-23 | 2010-06-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo [4,3-b]pyridazin-derivate |
| WO2010100144A1 (en) | 2009-03-04 | 2010-09-10 | Merck Serono S.A. | Fused bicyclic compounds as inhibitors for pi3 kinase |
| EP2414337B1 (en) * | 2009-04-03 | 2013-05-01 | Cellzome GmbH | Methods for the identification of kinase interacting molecules and for the purification of kinase proteins |
| DE102009033208A1 (de) * | 2009-07-15 | 2011-01-20 | Merck Patent Gmbh | Aminopyridinderivate |
| JP2013514973A (ja) * | 2009-12-21 | 2013-05-02 | メルク・シャープ・エンド・ドーム・コーポレイション | チロシンキナーゼ阻害剤 |
| KR101995013B1 (ko) * | 2010-07-13 | 2019-07-02 | 에프. 호프만-라 로슈 아게 | Irak4 조절제로서 피라졸로[1,5a]피리미딘 및 티에노[3,2b]피리미딘 유도체 |
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| CN104662014A (zh) | 2015-05-27 |
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| EP2872501A1 (en) | 2015-05-20 |
| CA2878621C (en) | 2020-09-15 |
| US9216991B2 (en) | 2015-12-22 |
| WO2014008992A1 (en) | 2014-01-16 |
| HK1210778A1 (en) | 2016-05-06 |
| BR112015000399A2 (pt) | 2017-06-27 |
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