ES2672701T3 - Nuevos inhibidores de histona deacetilasa y su uso en terapia - Google Patents
Nuevos inhibidores de histona deacetilasa y su uso en terapia Download PDFInfo
- Publication number
- ES2672701T3 ES2672701T3 ES13792060.9T ES13792060T ES2672701T3 ES 2672701 T3 ES2672701 T3 ES 2672701T3 ES 13792060 T ES13792060 T ES 13792060T ES 2672701 T3 ES2672701 T3 ES 2672701T3
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- amino
- mmol
- pyridin
- methyl
- alkyl
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- 239000003276 histone deacetylase inhibitor Substances 0.000 title claims description 24
- 229940121372 histone deacetylase inhibitor Drugs 0.000 title claims description 7
- 238000002560 therapeutic procedure Methods 0.000 title claims description 4
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- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 29
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 22
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims abstract description 11
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
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- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
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- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims abstract description 7
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- 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 claims abstract description 6
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims abstract description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910006069 SO3H Inorganic materials 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
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- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
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- DTSWVZIEMROXHQ-UHFFFAOYSA-N 7-[(5-fluoropyridin-2-yl)-(1-methylpyrazol-3-yl)amino]-n-hydroxyheptanamide Chemical compound CN1C=CC(N(CCCCCCC(=O)NO)C=2N=CC(F)=CC=2)=N1 DTSWVZIEMROXHQ-UHFFFAOYSA-N 0.000 claims description 3
- RUGSZKOQAROHTP-UHFFFAOYSA-N 7-[(5-fluoropyridin-2-yl)-(3-methyl-1,2,4-thiadiazol-5-yl)amino]-n-hydroxyheptanamide Chemical compound CC1=NSC(N(CCCCCCC(=O)NO)C=2N=CC(F)=CC=2)=N1 RUGSZKOQAROHTP-UHFFFAOYSA-N 0.000 claims description 3
- FCQMZQPBVGDJRA-UHFFFAOYSA-N 7-[(5-fluoropyridin-2-yl)-[3-(trifluoromethyl)-1,2,4-thiadiazol-5-yl]amino]-n-hydroxyheptanamide Chemical compound C=1C=C(F)C=NC=1N(CCCCCCC(=O)NO)C1=NC(C(F)(F)F)=NS1 FCQMZQPBVGDJRA-UHFFFAOYSA-N 0.000 claims description 3
- SDHCJCKTSOINRV-UHFFFAOYSA-N 7-[1,3-benzoxazol-2-yl(pyridin-2-yl)amino]-n-hydroxyheptanamide Chemical compound N=1C2=CC=CC=C2OC=1N(CCCCCCC(=O)NO)C1=CC=CC=N1 SDHCJCKTSOINRV-UHFFFAOYSA-N 0.000 claims description 3
- XZLSRIUXMLZDIG-UHFFFAOYSA-N 7-[1,3-benzoxazol-2-yl-(5-fluoropyridin-2-yl)amino]-n-hydroxyheptanamide Chemical compound N=1C2=CC=CC=C2OC=1N(CCCCCCC(=O)NO)C1=CC=C(F)C=N1 XZLSRIUXMLZDIG-UHFFFAOYSA-N 0.000 claims description 3
- LYKCBCSSOCTSJS-UHFFFAOYSA-N 8-[1,3-benzoxazol-2-yl(pyridin-2-yl)amino]-n-hydroxyoctanamide Chemical compound N=1C2=CC=CC=C2OC=1N(CCCCCCCC(=O)NO)C1=CC=CC=N1 LYKCBCSSOCTSJS-UHFFFAOYSA-N 0.000 claims description 3
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- JATJXQVARVZNCX-UHFFFAOYSA-N n-hydroxy-7-[pyridin-2-yl(1,2,4-thiadiazol-5-yl)amino]heptanamide Chemical compound C=1C=CC=NC=1N(CCCCCCC(=O)NO)C1=NC=NS1 JATJXQVARVZNCX-UHFFFAOYSA-N 0.000 claims description 3
- NSWXYHYGBYWCCU-UHFFFAOYSA-N n-hydroxy-7-[pyridin-2-yl(1,3-thiazol-2-yl)amino]heptanamide Chemical compound C=1C=CC=NC=1N(CCCCCCC(=O)NO)C1=NC=CS1 NSWXYHYGBYWCCU-UHFFFAOYSA-N 0.000 claims description 3
- FJPDRDDLAWLIEY-UHFFFAOYSA-N n-hydroxy-8-[(3-methyl-1,2,4-oxadiazol-5-yl)-pyridin-2-ylamino]octanamide Chemical compound CC1=NOC(N(CCCCCCCC(=O)NO)C=2N=CC=CC=2)=N1 FJPDRDDLAWLIEY-UHFFFAOYSA-N 0.000 claims description 3
- PLXKEIWLYDAYRS-UHFFFAOYSA-N n-hydroxy-8-[pyridin-2-yl-[3-(trifluoromethyl)-1,2,4-thiadiazol-5-yl]amino]octanamide Chemical compound C=1C=CC=NC=1N(CCCCCCCC(=O)NO)C1=NC(C(F)(F)F)=NS1 PLXKEIWLYDAYRS-UHFFFAOYSA-N 0.000 claims description 3
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- SJHVTQMOCHVEGJ-UHFFFAOYSA-N 7-[(5-fluoropyridin-2-yl)-(3-methyl-1,2,4-oxadiazol-5-yl)amino]-n-hydroxyheptanamide Chemical compound CC1=NOC(N(CCCCCCC(=O)NO)C=2N=CC(F)=CC=2)=N1 SJHVTQMOCHVEGJ-UHFFFAOYSA-N 0.000 claims description 2
- DMKMUYIOEGFWFU-UHFFFAOYSA-N 7-[[4-(4-fluorophenyl)pyridin-2-yl]-(1-methylpyrazol-3-yl)amino]-n-hydroxyheptanamide Chemical compound CN1C=CC(N(CCCCCCC(=O)NO)C=2N=CC=C(C=2)C=2C=CC(F)=CC=2)=N1 DMKMUYIOEGFWFU-UHFFFAOYSA-N 0.000 claims description 2
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- C07D417/00—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
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Landscapes
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| GB201315254A GB201315254D0 (en) | 2013-08-28 | 2013-08-28 | Compounds |
| GB201315254 | 2013-08-28 | ||
| PCT/GB2013/052917 WO2014072714A1 (en) | 2012-11-07 | 2013-11-06 | Novel histone deacetylase inhibitors and their use in therapy |
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| PT2994465T (pt) | 2013-05-10 | 2018-10-25 | Karus Therapeutics Ltd | Novos inibidores de histona desacetilase |
| US10029997B2 (en) * | 2014-06-12 | 2018-07-24 | Cedars-Sinai Medical Center | Compositions and methods for treating cancers |
| GB201419228D0 (en) * | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
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| ES2983284T3 (es) | 2018-01-09 | 2024-10-22 | Shuttle Pharmaceuticals Inc | Inhibidores selectivos de histona deacetilasa para el tratamiento de enfermedades humanas |
| BR112021026334A2 (pt) | 2019-06-27 | 2022-05-10 | Medstar Health | Macrófagos ativados por hdac6, composições, e usos dos mesmos |
Family Cites Families (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017500A (en) | 1973-07-16 | 1977-04-12 | Schering Corporation | Certain 8-amino-1,7-naphthyridines |
| US4792562A (en) * | 1985-12-04 | 1988-12-20 | Hoechst-Roussel Pharmaceuticals, Inc. | N-(pyrrol-1-yl)pyridinamines having memory enhancing activity |
| JPH0532662A (ja) | 1990-11-09 | 1993-02-09 | Nissan Chem Ind Ltd | 置換ピラゾール誘導体および農園芸用殺菌剤 |
| US5214038A (en) | 1991-04-15 | 1993-05-25 | Hoechst-Roussel Pharmaceuticals Inc. | 1-(pyrido[3,4-b]-1,4-oxazinyl-4-yl)-1H-indoles and intermediates for the preparation thereof |
| JP2000511883A (ja) | 1996-04-19 | 2000-09-12 | ノボ ノルディスク アクティーゼルスカブ | ホスホチロシン認識ユニットを有する分子のモジュレーター |
| EP0887348A1 (en) * | 1997-06-25 | 1998-12-30 | Boehringer Mannheim Italia S.p.A. | Bis-Indole derivatives having antimetastatic activity, a process for their preparation and pharmaceutical compositions containing them |
| JP3712529B2 (ja) | 1998-04-24 | 2005-11-02 | 大鵬薬品工業株式会社 | ３，３−ジピリジルアクリル酸アミド誘導体又はその薬学的に許容される塩 |
| ATE438880T1 (de) | 1999-02-12 | 2009-08-15 | Hoya Corp | Brille und ihre herstellung |
| JP5278983B2 (ja) | 1999-11-17 | 2013-09-04 | 塩野義製薬株式会社 | アミド化合物の新規用途 |
| GB9929988D0 (en) | 1999-12-17 | 2000-02-09 | Celltech Therapeutics Ltd | Chemical compounds |
| WO2001083456A1 (en) | 2000-04-27 | 2001-11-08 | Yamanouchi Pharmaceutical Co., Ltd. | Condensed heteroaryl derivatives |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| JP2004502686A (ja) | 2000-06-30 | 2004-01-29 | スージェン・インコーポレーテッド | ４−ヘテロアリール−３−ヘテロアリーリデニル−２−インドリノンおよび蛋白質キナーゼ阻害剤としてのその使用 |
| WO2002034748A1 (fr) * | 2000-10-24 | 2002-05-02 | Sankyo Company, Limited | Derives d'imidazopyridine |
| JP2002255964A (ja) * | 2000-10-24 | 2002-09-11 | Sankyo Co Ltd | イミダゾピリジン誘導体 |
| US6905669B2 (en) | 2001-04-24 | 2005-06-14 | Supergen, Inc. | Compositions and methods for reestablishing gene transcription through inhibition of DNA methylation and histone deacetylase |
| US7429593B2 (en) | 2001-09-14 | 2008-09-30 | Shionogi & Co., Ltd. | Utilities of amide compounds |
| ES2347544T3 (es) | 2002-03-13 | 2010-11-02 | Janssen Pharmaceutica Nv | Inhibidores de histona-desacetilasas. |
| JP2003313126A (ja) * | 2002-04-23 | 2003-11-06 | Sankyo Co Ltd | イミダゾピリジン誘導体を有効成分とする医薬 |
| JP2004002826A (ja) * | 2002-04-24 | 2004-01-08 | Sankyo Co Ltd | 高分子イミダゾピリジン誘導体 |
| JP4235726B2 (ja) | 2002-11-19 | 2009-03-11 | 国立大学法人 奈良先端科学技術大学院大学 | 大きな二光子吸収特性を示すアセチレン結合により連結されたビス（イミダゾリルポルフィリン金属錯体）を構成単位とするポルフィリン連鎖体及びその製造方法 |
| AU2003900608A0 (en) | 2003-02-11 | 2003-02-27 | Fujisawa Pharmaceutical Co., Ltd. | Hdac inhibitor |
| WO2005082887A1 (ja) | 2004-02-26 | 2005-09-09 | Aska Pharmaceutical Co., Ltd. | ピリミジン誘導体 |
| JP4698671B2 (ja) * | 2004-06-01 | 2011-06-08 | エフ．ホフマン−ラ ロシュ アーゲー | モノアミン再取り込み阻害剤としての３−アミノ−１−アリールプロピルインドール |
| CA2581489A1 (en) | 2004-10-06 | 2006-04-13 | Recepticon Aps | Use of compounds for the prevention of drug-induced cell toxicity |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| EP1851219A1 (en) | 2005-02-14 | 2007-11-07 | Miikana Therapeutics, Inc. | Fused heterocyclic compounds useful as inhibitors of histone deacetylase |
| EP1881983B1 (en) | 2005-05-20 | 2012-01-11 | Vertex Pharmaceuticals, Inc. | Pyrrolopyridines useful as inhibitors of protein kinase |
| TW200716545A (en) * | 2005-06-10 | 2007-05-01 | Sigma Tau Ind Farmaceuti | Indole derivatives having anti-tumor activity |
| AU2006306542B2 (en) | 2005-10-21 | 2012-04-19 | Merck Sharp & Dohme Corp. | Potassium channel inhibitors |
| CA2635899A1 (en) | 2006-01-19 | 2007-07-26 | Osi Pharmaceuticals, Inc. | Fused heterobicyclic kinase inhibitors |
| WO2007085540A1 (en) | 2006-01-27 | 2007-08-02 | Glaxo Group Limited | 1h-indaz0l-4-yl-2 , 4-pyrimidinediamine derivatives |
| KR101402474B1 (ko) | 2006-04-26 | 2014-06-19 | 제넨테크, 인크. | 포스포이노시티드 3-키나제 억제제 화합물 및 이를 포함하는 약학적 조성물 |
| MX2008013582A (es) | 2006-04-26 | 2009-01-19 | Hoffmann La Roche | Derivados de pirimidina como inhibidores de fosfatidilinositol-3-c inasa. |
| EP2050734A1 (en) | 2006-07-13 | 2009-04-22 | Kyowa Hakko Kirin Co., Ltd. | Pentadienamide derivative |
| WO2008033746A2 (en) | 2006-09-11 | 2008-03-20 | Curis, Inc. | Tyrosine kinase inhibitors containing a zinc binding moiety |
| CN103275067B (zh) | 2006-10-28 | 2015-09-02 | 梅特希尔基因公司 | 组蛋白脱乙酰酶抑制剂 |
| CA2670223A1 (en) | 2006-11-22 | 2008-05-29 | Karus Therapeutics Limited | Depsipeptides and their therapeutic use |
| AU2008210455A1 (en) | 2007-01-31 | 2008-08-07 | Vertex Pharmaceuticals Incorporated | 2-aminopyridine derivatives useful as kinase inhibitors |
| CN101663276A (zh) | 2007-01-31 | 2010-03-03 | 沃泰克斯药物股份有限公司 | 用作激酶抑制剂的2-氨基吡啶衍生物 |
| WO2008139987A1 (ja) | 2007-04-26 | 2008-11-20 | Japan Science And Technology Agency | Ｇタンパク質共役型レセプタ－作動剤 |
| WO2008137270A1 (en) * | 2007-05-04 | 2008-11-13 | H. Lundbeck A/S | Methods of diagnosing and monitoring of npy y5 based disorders |
| WO2008150827A1 (en) | 2007-05-29 | 2008-12-11 | Smithkline Beecham Corporation | Naphthyridine, derivatives as p13 kinase inhibitors |
| GB0710528D0 (en) | 2007-06-01 | 2007-07-11 | Glaxo Group Ltd | Novel compounds |
| WO2009063240A1 (en) | 2007-11-16 | 2009-05-22 | Arrow Therapeutics Limited | 2,4-diaminopyrimidine derivatives useful as inhibitors of aurora kinase |
| WO2009137462A2 (en) | 2008-05-05 | 2009-11-12 | Envivo Pharmaceuticals, Inc. | Methods for treating cognitive disorders using inhibitors of histone deacetylase |
| CA2732087A1 (en) | 2008-08-05 | 2010-02-11 | Boehringer Ingelheim International Gmbh | Substituted naphthyridines and their use as medicaments |
| AU2009299894A1 (en) | 2008-10-03 | 2010-04-08 | Merck Serono S.A. | 4 -morpholino-pyrido [3, 2 -d] pyrimidines active on Pi3k |
| GB2465405A (en) | 2008-11-10 | 2010-05-19 | Univ Basel | Triazine, pyrimidine and pyridine analogues and their use in therapy |
| MX2011007864A (es) | 2009-01-28 | 2011-09-30 | Karus Therapeutics Ltd | Isosteros para realzar la transcripcion y su uso en terapia. |
| CN102498115B (zh) | 2009-08-20 | 2016-12-07 | 卡鲁斯治疗有限公司 | 作为磷酸肌醇3-激酶抑制剂的三环杂环化合物 |
| GB201007347D0 (en) | 2010-04-30 | 2010-06-16 | Karus Therapeutics Ltd | Compounds |
| AU2011311531B2 (en) | 2010-10-08 | 2014-11-20 | Life Sciences Research Partners Vzw | HDAC inhibitors to treat Charcot-Marie-Tooth disease |
| MX2013006858A (es) | 2010-12-16 | 2013-07-29 | Hoffmann La Roche | Compuesto triciclicos inhibidores de la pi3k y metodos de uso. |
| WO2012106343A2 (en) | 2011-02-01 | 2012-08-09 | The Board Of Trustees Of The University Of Illinois | Hdac inhibitors and therapeutic methods using the same |
| EP2508510A1 (en) | 2011-04-06 | 2012-10-10 | Ikerchem, S.L. | Hydroxyphenyl pyrrole compounds containing an hydroxamic acid as hdac inhibitors and medicinal applications thereof |
| AU2012319188B2 (en) | 2011-10-03 | 2016-11-24 | Sloan-Kettering Institute For Cancer Research | Novel molecules that selectively inhibit histone deacetylase 6 relative to histone deacetylase 1 |
| JP6240078B2 (ja) * | 2011-10-04 | 2017-11-29 | バルーク エス．ブルームバーグ インスティテュート | 肝細胞癌を含む癌の阻害剤、および肝炎ウイルス複製の阻害剤としての置換アミノチアゾール |
| DK2790705T3 (en) | 2011-12-15 | 2018-03-12 | Novartis Ag | Use of inhibitors of the activity or function of PI3K |
| KR101415742B1 (ko) | 2011-12-21 | 2014-07-04 | 영남대학교 산학협력단 | 6―아미노피리딘―3―올 유도체 또는 이의 약제학적 허용가능한 염 및 이를 유효성분으로 함유하는 혈관신생으로 인한 질환의 예방 또는 치료용 약학조성물 |
| GB201204125D0 (en) | 2012-03-08 | 2012-04-25 | Karus Therapeutics Ltd | Compounds |
| WO2014032019A2 (en) | 2012-08-23 | 2014-02-27 | Georgetown University | Compounds and methods of use thereof for treating tumors |
| IN2015DN03235A (OSRAM) * | 2012-11-07 | 2015-10-02 | Karus Therapeutics Ltd | |
| US9737521B2 (en) | 2012-11-08 | 2017-08-22 | Rhizen Pharmaceuticals Sa | Pharmaceutical compositions containing a PDE4 inhibitor and a PI3 delta or dual PI3 delta-gamma kinase inhibitor |
| US9169214B2 (en) | 2012-12-21 | 2015-10-27 | The Board Of Trustees Of The Leland Stanford Junior University | Compounds and compositions that bind and stabilize transthyretin and their use for inhibiting transthyretin amyloidosis and protein-protein interactions |
| WO2014139145A1 (en) | 2013-03-15 | 2014-09-18 | Hutchison Medipharma Limited | Novel pyrimidine and pyridine compounds and usage thereof |
| WO2014153280A1 (en) | 2013-03-22 | 2014-09-25 | Merck Sharp & Dohme Corp. | 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
| PT2994465T (pt) | 2013-05-10 | 2018-10-25 | Karus Therapeutics Ltd | Novos inibidores de histona desacetilase |
| GB201402431D0 (en) | 2014-02-12 | 2014-03-26 | Karus Therapeutics Ltd | Compounds |
| EP3187497A4 (en) | 2014-08-26 | 2018-02-07 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| GB201419264D0 (en) | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
| GB201419228D0 (en) * | 2014-10-29 | 2014-12-10 | Karus Therapeutics Ltd | Compounds |
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2013
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- 2013-11-06 ES ES13792060.9T patent/ES2672701T3/es active Active
- 2013-11-06 JP JP2015540220A patent/JP6329958B2/ja not_active Expired - Fee Related
- 2013-11-06 NZ NZ707366A patent/NZ707366A/en not_active IP Right Cessation
- 2013-11-06 MX MX2015005132A patent/MX364295B/es active IP Right Grant
- 2013-11-06 CA CA2888861A patent/CA2888861A1/en not_active Abandoned
- 2013-11-06 US US14/441,401 patent/US9676765B2/en not_active Expired - Fee Related
- 2013-11-06 CN CN201380058397.3A patent/CN104797573A/zh active Pending
- 2013-11-06 EP EP13792060.9A patent/EP2917202B1/en not_active Not-in-force
- 2013-11-06 AU AU2013343291A patent/AU2013343291B2/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2014072714A1 (en) | 2014-05-15 |
| US10150763B2 (en) | 2018-12-11 |
| JP2015535273A (ja) | 2015-12-10 |
| EP2917202B1 (en) | 2018-05-02 |
| AU2013343291B2 (en) | 2018-05-10 |
| AU2013343291A1 (en) | 2015-05-07 |
| US20180086750A1 (en) | 2018-03-29 |
| NZ707366A (en) | 2018-11-30 |
| CA2888861A1 (en) | 2014-05-15 |
| IN2015DN03235A (OSRAM) | 2015-10-02 |
| CN104797573A (zh) | 2015-07-22 |
| EP2917202A1 (en) | 2015-09-16 |
| MX364295B (es) | 2019-04-22 |
| US20150361074A1 (en) | 2015-12-17 |
| MX2015005132A (es) | 2015-12-07 |
| US9676765B2 (en) | 2017-06-13 |
| JP6329958B2 (ja) | 2018-05-23 |
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