EA027139B1 - Замещенные 5-(3,5-диметилизоксазол-4-ил)индолин-2-оны - Google Patents
Замещенные 5-(3,5-диметилизоксазол-4-ил)индолин-2-оны Download PDFInfo
- Publication number
- EA027139B1 EA027139B1 EA201592024A EA201592024A EA027139B1 EA 027139 B1 EA027139 B1 EA 027139B1 EA 201592024 A EA201592024 A EA 201592024A EA 201592024 A EA201592024 A EA 201592024A EA 027139 B1 EA027139 B1 EA 027139B1
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- EA
- Eurasian Patent Office
- Prior art keywords
- substituted
- group
- alkyl
- hydrocarbon
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- Prior art date
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- PNEOXXLEDMCUHR-UHFFFAOYSA-N 5-(3,5-dimethyl-1,2-oxazol-4-yl)-1,3-dihydroindol-2-one Chemical class Cc1noc(C)c1-c1ccc2NC(=O)Cc2c1 PNEOXXLEDMCUHR-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 173
- 150000002430 hydrocarbons Chemical class 0.000 claims description 95
- 239000003153 chemical reaction reagent Substances 0.000 claims description 89
- 229930195733 hydrocarbon Natural products 0.000 claims description 89
- 239000004215 Carbon black (E152) Substances 0.000 claims description 88
- 238000010828 elution Methods 0.000 claims description 68
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 54
- 238000004587 chromatography analysis Methods 0.000 claims description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 27
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 27
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 19
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 18
- 238000004296 chiral HPLC Methods 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 230000000694 effects Effects 0.000 claims description 12
- 239000002246 antineoplastic agent Substances 0.000 claims description 11
- 239000002552 dosage form Substances 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 241000710771 Tick-borne encephalitis virus Species 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
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- 229940002612 prodrug Drugs 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000004193 piperazinyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 3
- -1 4-substituted 5-(3,5-dimethylisoxazol-4-yl)indoline-2-one compound Chemical class 0.000 abstract description 142
- 102000001805 Bromodomains Human genes 0.000 abstract description 18
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- 230000001404 mediated effect Effects 0.000 abstract 1
- 238000004949 mass spectrometry Methods 0.000 description 140
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 135
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- AKUSZFPCJFNRSZ-UHFFFAOYSA-N 3,4-dimethyl-1,2-oxazole Chemical compound CC1=CON=C1C AKUSZFPCJFNRSZ-UHFFFAOYSA-N 0.000 description 12
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 125000002619 bicyclic group Chemical group 0.000 description 12
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- OWPNVXATCSXTBK-UHFFFAOYSA-N 1-phenyl-3h-indol-2-one Chemical compound O=C1CC2=CC=CC=C2N1C1=CC=CC=C1 OWPNVXATCSXTBK-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
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- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 11
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- JXOVITKVSBVDGV-UHFFFAOYSA-N 3-chloro-5-(3,5-dimethyl-1,2-oxazol-4-yl)-3-phenyl-1h-indol-2-one Chemical compound CC1=NOC(C)=C1C1=CC=C(NC(=O)C2(Cl)C=3C=CC=CC=3)C2=C1 JXOVITKVSBVDGV-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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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- Life Sciences & Earth Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Tropical Medicine & Parasitology (AREA)
- Heart & Thoracic Surgery (AREA)
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- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
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- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013074780 | 2013-04-26 | ||
| PCT/CN2014/075257 WO2014173241A1 (en) | 2013-04-26 | 2014-04-14 | Substituted5-(3,5-dimethylisoxazol-4-yl)indoline-2-ones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201592024A1 EA201592024A1 (ru) | 2016-05-31 |
| EA027139B1 true EA027139B1 (ru) | 2017-06-30 |
Family
ID=51791046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201592024A EA027139B1 (ru) | 2013-04-26 | 2014-04-14 | Замещенные 5-(3,5-диметилизоксазол-4-ил)индолин-2-оны |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US9393232B2 (enExample) |
| EP (1) | EP2989096B1 (enExample) |
| JP (1) | JP6388915B2 (enExample) |
| AU (1) | AU2014256750B2 (enExample) |
| BR (1) | BR112015027130A2 (enExample) |
| CA (1) | CA2901083A1 (enExample) |
| EA (1) | EA027139B1 (enExample) |
| HK (1) | HK1217484A1 (enExample) |
| IL (1) | IL240126A0 (enExample) |
| MX (1) | MX366623B (enExample) |
| SG (1) | SG11201506829XA (enExample) |
| WO (1) | WO2014173241A1 (enExample) |
Families Citing this family (29)
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| WO2014080291A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Biaryl derivatives as bromodomain inhibitors |
| US9073878B2 (en) | 2012-11-21 | 2015-07-07 | Zenith Epigenetics Corp. | Cyclic amines as bromodomain inhibitors |
| WO2014096965A2 (en) | 2012-12-21 | 2014-06-26 | Rvx Therapeutics Inc. | Novel heterocyclic compounds as bromodomain inhibitors |
| MX366703B (es) | 2013-03-15 | 2019-07-22 | Incyte Holdings Corp | Heterociclos tricíclicos como inhibidores de la proteína bet. |
| CA2901083A1 (en) | 2013-04-26 | 2014-10-30 | Beigene, Ltd. | Substituted 5-(3,5-dimethylisoxazol-4-yl)indoline-2-ones |
| WO2015004533A2 (en) | 2013-06-21 | 2015-01-15 | Zenith Epigenetics Corp. | Novel substituted bicyclic compounds as bromodomain inhibitors |
| SG11201510409QA (en) | 2013-06-21 | 2016-01-28 | Zenith Epigenetics Corp | Novel bicyclic bromodomain inhibitors |
| WO2015006193A1 (en) | 2013-07-08 | 2015-01-15 | Incyte Corporation | Tricyclic heterocycles as bet protein inhibitors |
| WO2015015318A2 (en) | 2013-07-31 | 2015-02-05 | Zenith Epigenetics Corp. | Novel quinazolinones as bromodomain inhibitors |
| WO2015081203A1 (en) | 2013-11-26 | 2015-06-04 | Incyte Corporation | Bicyclic heterocycles as bet protein inhibitors |
| US9315501B2 (en) | 2013-11-26 | 2016-04-19 | Incyte Corporation | Bicyclic heterocycles as BET protein inhibitors |
| US9309246B2 (en) | 2013-12-19 | 2016-04-12 | Incyte Corporation | Tricyclic heterocycles as BET protein inhibitors |
| UA119870C2 (uk) | 2014-04-23 | 2019-08-27 | Інсайт Корпорейшн | 1H-ПІРОЛО[2,3-c]ПІРИДИН-7(6H)-ОНИ ТА ПІРАЗОЛО[3,4-c]ПІРИДИН-7(6H)-ОНИ ЯК ІНГІБІТОРИ БІЛКІВ BET |
| ES2855225T3 (es) | 2014-09-15 | 2021-09-23 | Incyte Corp | Heterociclos tricíclicos para su uso como inhibidores de proteínas BET |
| EP3227280B1 (en) | 2014-12-01 | 2019-04-24 | Zenith Epigenetics Ltd. | Substituted pyridines as bromodomain inhibitors |
| US10710992B2 (en) | 2014-12-01 | 2020-07-14 | Zenith Epigenetics Ltd. | Substituted pyridinones as bromodomain inhibitors |
| JP2017537946A (ja) | 2014-12-11 | 2017-12-21 | ゼニス・エピジェネティクス・リミテッドＺｅｎｉｔｈ Ｅｐｉｇｅｎｅｔｉｃｓ Ｌｔｄ． | ブロモドメイン阻害剤としての置換複素環 |
| HK1245247A1 (zh) | 2014-12-17 | 2018-08-24 | 恒翼生物医药科技(上海)有限公司 | 溴结构域的抑制剂 |
| CN105985282B (zh) * | 2015-01-28 | 2020-12-08 | 中国科学院广州生物医药与健康研究院 | 一种2-氧代-1,2-二氢苯并[cd]吲哚类化合物及其应用 |
| GB201504694D0 (en) | 2015-03-19 | 2015-05-06 | Glaxosmithkline Ip Dev Ltd | Covalent conjugates |
| WO2016203335A1 (en) | 2015-06-18 | 2016-12-22 | Pfizer Inc. | Novel pyrido[2,3-b]pyrazinones as bet-family bromodomain inhibitors |
| TW201722966A (zh) | 2015-10-29 | 2017-07-01 | 英塞特公司 | Bet蛋白質抑制劑之非晶固體形式 |
| AU2017281286B2 (en) | 2016-06-20 | 2021-05-20 | Incyte Corporation | Crystalline solid forms of a bet inhibitor |
| KR102282794B1 (ko) | 2016-07-29 | 2021-07-27 | 온크터널 테라퓨틱스, 인코포레이티드. | 인돌리논 화합물의 용도 |
| GB201716392D0 (en) | 2017-10-06 | 2017-11-22 | Glaxosmithkline Intellectual Property (No 2) Ltd | Compounds |
| ES3053198T3 (en) * | 2018-08-27 | 2026-01-20 | Arcus Biosciences Inc | Cd73 inhibitors |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
| CN118451073A (zh) * | 2021-12-29 | 2024-08-06 | 百济神州有限公司 | 杂环化合物 |
| WO2025064918A1 (en) * | 2023-09-20 | 2025-03-27 | The Board Of Regents Of The University Of Texas System | First-in-class phospho-brd4 inhibitors |
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| WO2010009166A1 (en) * | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Oxindolyl inhibitor compounds |
| CN101910182A (zh) * | 2007-12-28 | 2010-12-08 | 田边三菱制药株式会社 | 抗癌剂 |
| CN102656147A (zh) * | 2009-12-11 | 2012-09-05 | 霍夫曼-拉罗奇有限公司 | 可用作ampk调节剂的螺吲哚-环丙烷二氢吲哚酮 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0420970D0 (en) | 2004-09-21 | 2004-10-20 | Smithkline Beecham Corp | Novel triazoloquinoline compounds |
| GB0919431D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| KR20120097508A (ko) | 2009-11-05 | 2012-09-04 | 글락소스미스클라인 엘엘씨 | 벤조디아제핀 브로모도메인 억제제 |
| GB0919434D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| GB0919432D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Use |
| MY160456A (en) | 2009-11-05 | 2017-03-15 | Glaxosmithkline Llc | Benzodiazepine bromodomain inhibitor |
| GB0919423D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| GB0919426D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
| WO2011069298A1 (en) | 2009-12-11 | 2011-06-16 | F. Hoffmann-La Roche Ag | Novel cyclopropane indolinone derivatives |
| CA2799381A1 (en) | 2010-05-14 | 2011-11-17 | Dana-Farber Cancer Institute, Inc. | Male contraceptive compositions and methods of use |
| US8981083B2 (en) | 2010-05-14 | 2015-03-17 | Dana Farber Cancer Institute, Inc. | Compositions and methods for treating neoplasia, inflammatory disease and other disorders |
| US9085582B2 (en) | 2010-06-22 | 2015-07-21 | Glaxosmithkline Llc | Benzotriazolodiazepine compounds inhibitors of bromodomains |
| AR084070A1 (es) | 2010-12-02 | 2013-04-17 | Constellation Pharmaceuticals Inc | Inhibidores del bromodominio y usos de los mismos |
| WO2012143436A1 (en) | 2011-04-21 | 2012-10-26 | Sanofi-Aventis Deutschland Gmbh | Medicated module with lock ring |
| WO2012151512A2 (en) | 2011-05-04 | 2012-11-08 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| CN105407894A (zh) | 2013-03-14 | 2016-03-16 | 康威基内有限公司 | 用于抑制含布罗莫结构域的蛋白质的方法和组合物 |
| EP2978757B1 (en) | 2013-03-27 | 2017-02-08 | Boehringer Ingelheim International GmbH | Indolinone analogues as brd4 inhibitors |
| CA2901083A1 (en) | 2013-04-26 | 2014-10-30 | Beigene, Ltd. | Substituted 5-(3,5-dimethylisoxazol-4-yl)indoline-2-ones |
-
2014
- 2014-04-14 CA CA2901083A patent/CA2901083A1/en not_active Abandoned
- 2014-04-14 BR BR112015027130A patent/BR112015027130A2/pt not_active Application Discontinuation
- 2014-04-14 EA EA201592024A patent/EA027139B1/ru not_active IP Right Cessation
- 2014-04-14 US US14/404,798 patent/US9393232B2/en active Active
- 2014-04-14 AU AU2014256750A patent/AU2014256750B2/en not_active Ceased
- 2014-04-14 HK HK16105442.5A patent/HK1217484A1/zh unknown
- 2014-04-14 WO PCT/CN2014/075257 patent/WO2014173241A1/en not_active Ceased
- 2014-04-14 MX MX2015014947A patent/MX366623B/es active IP Right Grant
- 2014-04-14 SG SG11201506829XA patent/SG11201506829XA/en unknown
- 2014-04-14 EP EP14788064.5A patent/EP2989096B1/en active Active
- 2014-04-14 JP JP2016509276A patent/JP6388915B2/ja not_active Expired - Fee Related
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2015
- 2015-07-23 IL IL240126A patent/IL240126A0/en unknown
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2016
- 2016-06-06 US US15/174,229 patent/US9827226B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101910182A (zh) * | 2007-12-28 | 2010-12-08 | 田边三菱制药株式会社 | 抗癌剂 |
| WO2010009166A1 (en) * | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Oxindolyl inhibitor compounds |
| CN102656147A (zh) * | 2009-12-11 | 2012-09-05 | 霍夫曼-拉罗奇有限公司 | 可用作ampk调节剂的螺吲哚-环丙烷二氢吲哚酮 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016517857A (ja) | 2016-06-20 |
| CA2901083A1 (en) | 2014-10-30 |
| EP2989096A4 (en) | 2016-11-02 |
| HK1217484A1 (zh) | 2017-01-13 |
| SG11201506829XA (en) | 2015-12-30 |
| EP2989096A1 (en) | 2016-03-02 |
| US9827226B2 (en) | 2017-11-28 |
| US20170027912A1 (en) | 2017-02-02 |
| US20160030395A1 (en) | 2016-02-04 |
| MX2015014947A (es) | 2016-03-07 |
| EP2989096B1 (en) | 2019-04-10 |
| JP6388915B2 (ja) | 2018-09-12 |
| AU2014256750A1 (en) | 2015-12-10 |
| AU2014256750B2 (en) | 2018-08-23 |
| WO2014173241A1 (en) | 2014-10-30 |
| MX366623B (es) | 2019-07-16 |
| BR112015027130A2 (pt) | 2018-07-24 |
| US9393232B2 (en) | 2016-07-19 |
| IL240126A0 (en) | 2015-09-24 |
| EA201592024A1 (ru) | 2016-05-31 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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