JP2014520863A - Ｂｒｕｔｏｎ型チロシンキナーゼの阻害剤 - Google Patents
Ｂｒｕｔｏｎ型チロシンキナーゼの阻害剤 Download PDFInfo
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Landscapes
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| PCT/US2012/046779 WO2013010136A2 (en) | 2011-07-13 | 2012-07-13 | Inhibitors of bruton's tyrosine kinase |
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| JP2014520863A true JP2014520863A (ja) | 2014-08-25 |
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| MX (1) | MX2014000518A (enExample) |
| PH (1) | PH12014500122A1 (enExample) |
| WO (1) | WO2013010136A2 (enExample) |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016121953A1 (ja) * | 2015-01-30 | 2016-08-04 | 大鵬薬品工業株式会社 | 免疫疾患の予防及び／又は治療剤 |
| JP2018527384A (ja) * | 2015-09-16 | 2018-09-20 | ロクソ オンコロジー， インコーポレイテッドＬｏｘｏ Ｏｎｃｏｌｏｇｙ， Ｉｎｃ． | がんの治療のためのｂｔｋ阻害剤としてのピラゾロピリミジン誘導体 |
| JP2019507793A (ja) * | 2016-03-11 | 2019-03-22 | コーバス・ファーマシューティカルズ・インコーポレイテッド | ブルトン型チロシンキナーゼを調節する化合物及び方法 |
| JP2019535820A (ja) * | 2016-11-15 | 2019-12-12 | ハンヂョウ ハーツ ファーマシューティカル カンパニー リミテッド | 選択性ブルトン型チロシンキナーゼ阻害剤及びその使用 |
| JP2022523480A (ja) * | 2019-01-18 | 2022-04-25 | ミンフイ ファーマシューティカル （シャンハイ） リミテッド | ブルトン型チロシンキナーゼ阻害剤としての環状分子 |
| JP2023545414A (ja) * | 2020-10-05 | 2023-10-30 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | Ｈｅｒ２の強力かつ選択的な阻害剤 |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20220213106A1 (en) * | 2006-09-22 | 2022-07-07 | Pharmacyclics Llc | Inhibitors of Bruton's Tyrosine Kinase |
| BR112013017722A2 (pt) | 2011-01-11 | 2016-07-12 | Glaxosmithkline Llc | combinação |
| US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| CN103534258B (zh) | 2011-05-17 | 2016-09-14 | 普林斯匹亚生物制药公司 | 酪氨酸激酶抑制剂 |
| JP2014517079A (ja) | 2011-06-22 | 2014-07-17 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| CN103857396A (zh) | 2011-07-13 | 2014-06-11 | 药品循环公司 | 布鲁顿酪氨酸激酶抑制剂 |
| SI3689878T1 (sl) | 2011-07-19 | 2021-12-31 | Merck Sharp & Dohme B.V. | 4-imidazopiridazin-1-il-benzamidi in 4-imidazotriazin-1-il-benzamidi kot Btk-zaviralci |
| EP2548877A1 (en) | 2011-07-19 | 2013-01-23 | MSD Oss B.V. | 4-(5-Membered fused pyridinyl)benzamides as BTK-inhibitors |
| PT3409278T (pt) | 2011-07-21 | 2020-12-18 | Sumitomo Dainippon Pharma Oncology Inc | Inibidores de proteína cinase heterocíclicos |
| US8377946B1 (en) | 2011-12-30 | 2013-02-19 | Pharmacyclics, Inc. | Pyrazolo[3,4-d]pyrimidine and pyrrolo[2,3-d]pyrimidine compounds as kinase inhibitors |
| LT3181567T (lt) | 2012-09-10 | 2019-07-25 | Principia Biopharma Inc. | Pirazolpirimidino junginiai kaip kinazės slopikliai |
| EP3418281B1 (en) | 2012-12-07 | 2020-09-30 | Vertex Pharmaceuticals Inc. | Pyrazolo[1,5-a]pyrimidines useful as inhibitors of atr kinase for the treatment of cancer diseases |
| US20160129084A1 (en) * | 2013-03-06 | 2016-05-12 | Acorda Therapeutics, Inc. | Therapeutic Dosing of a Neuregulin or a Fragment Thereof for Treatment or Prophylaxis of Heart Failure |
| US9152578B1 (en) * | 2013-03-12 | 2015-10-06 | Emc Corporation | Securing data replication, backup and mobility in cloud storage |
| DK2970205T3 (da) | 2013-03-14 | 2019-07-29 | Tolero Pharmaceuticals Inc | JAK2- og ALK2-inhibitorer og fremgangsmåder til anvendelse deraf |
| EP2970286A1 (en) | 2013-03-15 | 2016-01-20 | Vertex Pharmaceuticals Inc. | Fused pyrazolopyrimidine derivatives useful as inhibitors of atr kinase |
| KR102311329B1 (ko) * | 2013-03-15 | 2021-10-14 | 얀센 파마슈티카 엔.브이. | 약제를 제조하기 위한 방법 및 중간체 |
| EP2970288A1 (en) | 2013-03-15 | 2016-01-20 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| JP2016512239A (ja) | 2013-03-15 | 2016-04-25 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | Ａｔｒキナーゼの阻害剤として有用な化合物 |
| US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| GB201309085D0 (en) | 2013-05-20 | 2013-07-03 | Redx Pharma Ltd | Compounds |
| WO2014187319A1 (en) | 2013-05-21 | 2014-11-27 | Jiangsu Medolution Ltd | Substituted pyrazolopyrimidines as kinases inhibitors |
| BR112016002069B1 (pt) * | 2013-08-12 | 2020-08-18 | Taiho Pharmaceutical Co., Ltd | Composto de pirimidina fusionada ou sal deste, sonda, inibidor de btk, agente antitumor e composição farmacêutica compreendendo dito composto e usos terapêuticos do mesmo |
| EA201690618A1 (ru) * | 2013-09-30 | 2016-09-30 | Фармасайкликс Элэлси | Ингибиторы тирозинкиназы брутона |
| CN103626774B (zh) * | 2013-11-20 | 2015-11-04 | 苏州明锐医药科技有限公司 | 伊鲁替尼的制备方法 |
| KR20160093062A (ko) | 2013-12-05 | 2016-08-05 | 아세르타 파마. 비.브이. | Pi3k 억제제 및 btk 억제제의 치료적 조합 |
| EP3077397B1 (en) | 2013-12-06 | 2019-09-18 | Vertex Pharmaceuticals Inc. | 2-amino-6-fluoro-n-[5-fluoro-pyridin-3-yl]pyrazolo[1,5-a]pyrimidin-3-carboxamide compound useful as atr kinase inhibitor, its preparation, different solid forms and radiolabelled derivatives thereof |
| US10272083B2 (en) | 2014-01-21 | 2019-04-30 | Acerta Pharma B.V. | Methods of treating chronic lymphocytic leukemia and small lymphocytic leukemia using a BTK inhibitor |
| KR20220027271A (ko) | 2014-02-21 | 2022-03-07 | 프린시피아 바이오파마, 인코퍼레이티드 | Btk 억제제의 염 및 고체 형태 |
| RU2016139697A (ru) * | 2014-03-12 | 2018-04-12 | Новартис Аг | Комбинация, содержащая ингибитор btk и ингибитор akt |
| US9937171B2 (en) | 2014-04-11 | 2018-04-10 | Acerta Pharma B.V. | Methods of blocking the CXCR-4/SDF-1 signaling pathway with inhibitors of bruton's tyrosine kinase |
| CN105017256A (zh) | 2014-04-29 | 2015-11-04 | 浙江导明医药科技有限公司 | 多氟化合物作为布鲁顿酪氨酸激酶抑制剂 |
| CN103965201A (zh) * | 2014-04-30 | 2014-08-06 | 淮海工学院 | 一种合成依鲁替尼中间体4-氨基-3-(4-苯氧基苯基)-1H-吡唑并[3,4-d]嘧啶的方法 |
| ES2777608T3 (es) | 2014-06-05 | 2020-08-05 | Vertex Pharma | Derivados radiomarcados de un compuesto de 2-amino-6-fluoro-N-[5-fluoro-piridin-3-il]-pirazolo[1,5-a]pirimidin-3-carboxamida útiles como inhibidores de ATR cinasa, la preparación de dicho compuesto y diferentes formas sólidas del mismo |
| GB201410430D0 (en) * | 2014-06-11 | 2014-07-23 | Redx Pharma Ltd | Compounds |
| US9949971B2 (en) | 2014-06-17 | 2018-04-24 | Acerta Pharma B.V. | Therapeutic combinations of a BTK inhibitor, a PI3K inhibitor and/or a JAK-2 inhibitor |
| CA2950780C (en) | 2014-06-17 | 2023-05-16 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of chk1 and atr inhibitors |
| AT515941B1 (de) | 2014-07-29 | 2016-01-15 | Avl List Gmbh | Kondensationspartikelzähler mit einer Sättigungseinheit und einer nachgeschalteten Kondensationseinheit |
| WO2016019233A1 (en) | 2014-08-01 | 2016-02-04 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| PT3179991T (pt) | 2014-08-11 | 2021-11-26 | Acerta Pharma Bv | Combinações terapêuticas de um inibidor de btk e um inibidor de bcl-2 |
| TW201702218A (zh) | 2014-12-12 | 2017-01-16 | 美國杰克森實驗室 | 關於治療癌症、自體免疫疾病及神經退化性疾病之組合物及方法 |
| ES2843323T3 (es) | 2014-12-18 | 2021-07-16 | Principia Biopharma Inc | Tratamiento de pénfigo |
| US9717745B2 (en) | 2015-03-19 | 2017-08-01 | Zhejiang DTRM Biopharma Co. Ltd. | Pharmaceutical compositions and their use for treatment of cancer and autoimmune diseases |
| CN106146508A (zh) * | 2015-03-19 | 2016-11-23 | 浙江导明医药科技有限公司 | 优化的联合用药及其治疗癌症和自身免疫疾病的用途 |
| CN104844573A (zh) * | 2015-04-17 | 2015-08-19 | 中国药科大学 | 嘧啶类btk抑制剂、其制备方法及医药用途 |
| US20180305350A1 (en) | 2015-06-24 | 2018-10-25 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| SI3317281T1 (sl) | 2015-07-02 | 2020-08-31 | Acerta Pharma B.V. | Trdne oblike in formulacije (s)-4-(8-amino-3-(1-(but-2-inoil)pirolidin -2-il)imidazo(1,5-a)pirazin-1-il)-n-(piridin-2-il)benzamida |
| KR101766194B1 (ko) * | 2015-08-07 | 2017-08-10 | 한국과학기술연구원 | RET 키나아제 저해제인 신규 3-(이속사졸-3-일)-피라졸로[3,4-d]피리미딘-4-아민 화합물 |
| MY191938A (en) * | 2015-09-01 | 2022-07-19 | Taiho Pharmaceutical Co Ltd | Novel pyrazolo[3,4-d]pyrimidine compound or salt thereof |
| WO2017059357A1 (en) | 2015-09-30 | 2017-04-06 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of dna damaging agents and atr inhibitors |
| CN114605327B (zh) | 2015-12-16 | 2025-03-11 | 洛克索肿瘤学股份有限公司 | 可用作激酶抑制剂的化合物 |
| TWI722080B (zh) | 2015-12-24 | 2021-03-21 | 日商武田藥品工業股份有限公司 | 共結晶、其製造方法及含有共結晶的醫藥 |
| CN108602834B (zh) * | 2016-02-05 | 2021-01-08 | 北京盛诺基医药科技股份有限公司 | 一种布鲁顿酪氨酸激酶抑制剂 |
| CN109600989B (zh) | 2016-06-29 | 2022-11-04 | 普林斯匹亚生物制药公司 | 2-[3-[4-氨基-3-(2-氟-4-苯氧基-苯基)吡唑并[3,4-d]嘧啶-1-基]哌啶-1-羰基]-4-甲基-4-[4-(氧杂环丁烷-3-基)哌嗪-1-基]戊-2-烯腈的改性的释放制剂 |
| CN109851620B (zh) * | 2016-08-17 | 2020-08-07 | 深圳市塔吉瑞生物医药有限公司 | 用于抑制酪氨酸激酶活性的稠合双环类化合物 |
| TW201837040A (zh) * | 2017-03-15 | 2018-10-16 | 美商微拉製藥公司 | Cdpk1抑制劑及與其相關之組合物及方法 |
| CN107043366B (zh) * | 2017-04-25 | 2020-05-26 | 中国药科大学 | 4-氨基嘧啶类化合物、其制备方法及医药用途 |
| CN107383015B (zh) * | 2017-07-03 | 2019-11-08 | 四川大学华西医院 | 烷硫端基寡PEG修饰的氨基吡唑并[3,4-d]嘧啶衍生物及抗非小细胞肺癌的应用 |
| WO2019036001A1 (en) * | 2017-08-17 | 2019-02-21 | Vyera Pharmaceuticals, LLC | CDPK1 INHIBITOR, COMPOSITIONS AND RELATED METHODS |
| CN109422749B (zh) * | 2017-08-21 | 2023-01-24 | 重庆医药工业研究院有限责任公司 | 一种抑制单羧酸转运蛋白的嘧啶二酮衍生物 |
| TW201922256A (zh) | 2017-10-27 | 2019-06-16 | 中國大陸商浙江導明醫藥科技有限公司 | 治療淋巴樣惡性疾病之方法 |
| CN109970740A (zh) * | 2017-12-27 | 2019-07-05 | 广东众生药业股份有限公司 | 4-氨基-嘧啶并氮杂环衍生物及其制备方法和用途 |
| MX2020010437A (es) | 2018-04-05 | 2021-01-29 | Sumitomo Pharma Oncology Inc | Inhibidores de axl cinasa y uso de los mismos. |
| AU2019252793A1 (en) | 2018-04-13 | 2020-10-15 | Sumitomo Pharma America, Inc. | PIM kinase inhibitors for treatment of myeloproliferative neoplasms and fibrosis associated with cancer |
| KR20210038906A (ko) | 2018-07-26 | 2021-04-08 | 스미토모 다이니폰 파마 온콜로지, 인크. | 비정상적 acvr1 발현과 연관된 질환을 치료하는 방법 및 그에 사용하기 위한 acvr1 억제제 |
| AU2020221247B2 (en) | 2019-02-12 | 2024-12-12 | Sumitomo Pharma America, Inc. | Formulations comprising heterocyclic protein kinase inhibitors |
| KR20220080179A (ko) | 2019-10-14 | 2022-06-14 | 프린시피아 바이오파마, 인코퍼레이티드 | (R)-2-[3-[4-아미노-3-(2-플루오로-4-페녹시-페닐)피라졸로[3,4-d]피리미딘-1-일]피페리딘-1-카르보닐]-4-메틸-4-[4-(옥세탄-3-일)피페라진-1-일]펜트-2-엔니트릴을 투여하여 면역 혈소판 감소증을 치료하는 방법 |
| KR20220130184A (ko) | 2020-01-22 | 2022-09-26 | 프린시피아 바이오파마, 인코퍼레이티드 | 2-[3-[4-아미노-3-(2-플루오로-4-페녹시-페닐)-1H-피라졸로[3,4-d]피리미딘-1-일]피페리딘-1-카르보닐]-4-메틸-4-[4-(옥세탄-3-일)피페라진-1-일]펜트-2-엔니트릴의 결정질 형태 |
| WO2021164697A1 (zh) * | 2020-02-18 | 2021-08-26 | 深圳市塔吉瑞生物医药有限公司 | 取代的酰胺衍生物及其组合物及用途 |
| CN111303158A (zh) * | 2020-04-09 | 2020-06-19 | 成都睿智化学研究有限公司 | 一种（4-氯-1H-吡唑啉[3,4-d]嘧啶-3-基）芳基甲酮的制备方法 |
| CA3217452A1 (en) | 2021-05-14 | 2022-11-17 | David Andrew Coates | Cocrystalline forms of a bruton's tyrosine kinase inhibitor |
| CN120302975A (zh) | 2022-10-31 | 2025-07-11 | 住友制药美国公司 | 治疗骨髓增生性肿瘤的pim1抑制剂 |
| WO2025007055A1 (en) * | 2023-06-29 | 2025-01-02 | Volastra Therapeutics, Inc. | Aryl indol-3-yl ketone and aryl indazol-3-yl ketone inhibitors of kif18a |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005007085A2 (en) * | 2003-06-20 | 2005-01-27 | The Regents Of The University Of California | Pyrazolo pyrimidine derivatives and methods of use thereof |
| JP2008520744A (ja) * | 2004-11-19 | 2008-06-19 | ザ・レジェンツ・オブ・ザ・ユニバーシティ・オブ・カリフォルニア | 抗炎症性ピラゾロピリミジン |
| US20080214501A1 (en) * | 2006-11-03 | 2008-09-04 | Pharmacyclics, Inc. | Bruton's tyrosine kinase activity probe and method of using |
| WO2010045542A2 (en) * | 2008-10-16 | 2010-04-22 | The Regents Of The University Of California | Fused ring heteroaryl kinase inhibitors |
| EP2201840A1 (en) * | 2006-09-22 | 2010-06-30 | Pharmacyclics, Inc. | Inhibitors of Bruton's Tyrosine Kinase |
| JP2011503103A (ja) * | 2007-11-07 | 2011-01-27 | フォールドアールエックス ファーマシューティカルズ インコーポレーティッド | タンパク質輸送の調節方法 |
| US20110086866A1 (en) * | 2009-10-12 | 2011-04-14 | Pharmacyclics, Inc. | Inhibitors of bruton's tyrosine kinase |
Family Cites Families (120)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01167840A (ja) | 1987-12-24 | 1989-07-03 | Konica Corp | 新規な写真用シアンカプラー |
| GB9226855D0 (en) | 1992-12-23 | 1993-02-17 | Erba Carlo Spa | Vinylene-azaindole derivatives and process for their preparation |
| US6326469B1 (en) | 1994-04-22 | 2001-12-04 | Sugen, Inc. | Megakaryocytic protein tyrosine kinases |
| US5593997A (en) | 1995-05-23 | 1997-01-14 | Pfizer Inc. | 4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase inhibitors |
| CH690773A5 (de) | 1996-02-01 | 2001-01-15 | Novartis Ag | Pyrrolo(2,3-d)pyrimide und ihre Verwendung. |
| WO1997049706A1 (en) | 1996-06-25 | 1997-12-31 | Novartis Ag | SUBSTITUTED 7-AMINO-PYRROLO[3,2-d]PYRIMIDINES AND THE USE THEREOF |
| EP0970084B1 (en) | 1997-03-19 | 2003-06-04 | Basf Aktiengesellschaft | Pyrrolo 2,3d]pyrimidines and their use as tyrosine kinase inhibitors |
| US6303652B1 (en) | 1998-08-21 | 2001-10-16 | Hughes Institute | BTK inhibitors and methods for their identification and use |
| JP2002512216A (ja) | 1998-04-17 | 2002-04-23 | パーカー ヒューズ インスティテュート | Ｂｔｋインヒビターならびにその同定方法および使用方法 |
| US6335155B1 (en) | 1998-06-26 | 2002-01-01 | Sunesis Pharmaceuticals, Inc. | Methods for rapidly identifying small organic molecule ligands for binding to biological target molecules |
| US6998233B2 (en) | 1998-06-26 | 2006-02-14 | Sunesis Pharmaceuticals, Inc. | Methods for ligand discovery |
| US20050287596A9 (en) | 1998-06-26 | 2005-12-29 | Braisted Andrew C | Novel ligands and libraries of ligands |
| US6713474B2 (en) | 1998-09-18 | 2004-03-30 | Abbott Gmbh & Co. Kg | Pyrrolopyrimidines as therapeutic agents |
| HUP0200403A3 (en) | 1998-09-18 | 2004-07-28 | Abbott Gmbh & Co Kg | Pyrrolopyrimidines as protein kinase inhibitors, pharmaceutical compositions containing them and their use |
| US6306897B1 (en) | 1999-03-19 | 2001-10-23 | Parker Hughes Institute | Calanolides for inhibiting BTK |
| US6921763B2 (en) | 1999-09-17 | 2005-07-26 | Abbott Laboratories | Pyrazolopyrimidines as therapeutic agents |
| JP2003509428A (ja) | 1999-09-17 | 2003-03-11 | アボツト・ゲー・エム・ベー・ハー・ウント・コンパニー・カーゲー | 治療薬としてのピラゾロピリミジン |
| DE60014130T2 (de) | 1999-10-06 | 2006-03-09 | Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield | Heterocyclische verbindungen verwendbar als tyrosinkinase inhibitoren |
| US6506769B2 (en) | 1999-10-06 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic compounds useful as inhibitors of tyrosine kinases |
| JP2003516351A (ja) | 1999-11-30 | 2003-05-13 | パーカー ヒューズ インスティテュート | コラーゲン誘導血小板凝集阻害剤 |
| EP1246829A1 (en) | 1999-12-17 | 2002-10-09 | Ariad Pharmaceuticals, Inc. | Novel heterocycles |
| GB0005345D0 (en) | 2000-03-06 | 2000-04-26 | Mathilda & Terence Kennedy Ins | Methods of treating sepsis septic shock and inflammation |
| WO2001072751A1 (en) | 2000-03-29 | 2001-10-04 | Knoll Gesellschaft Mit Beschraenkter Haftung | Pyrrolopyrimidines as tyrosine kinase inhibitors |
| WO2002038797A2 (en) | 2000-10-23 | 2002-05-16 | Bristol-Myers Squibb Company | Modulators of bruton's tyrosine kinase, their identification and use |
| WO2002045684A2 (en) | 2000-12-06 | 2002-06-13 | Pharmacia Corporation | Rapidly dispersing pharmaceutical composition comprising effervescent agents |
| MXPA03008560A (es) | 2001-03-22 | 2004-06-30 | Abbot Gmbh & Co Kg | Pirazolopirimidinas como agentes terapeuticos. |
| US8306897B2 (en) | 2001-05-04 | 2012-11-06 | Stockshield, Inc. | Method and system for insuring against investment loss |
| US20030114467A1 (en) | 2001-06-21 | 2003-06-19 | Shakespeare William C. | Novel pyrazolo- and pyrrolo-pyrimidines and uses thereof |
| US20040248906A1 (en) | 2001-08-10 | 2004-12-09 | Donato Nicholas J | Use of c-src inhibitors alone or in combination with st1571 for the treatment of leukaemia |
| WO2003016338A1 (en) | 2001-08-15 | 2003-02-27 | Parker Hughes Institute | Crystal structure of the btk kinase domain |
| IL161409A0 (en) | 2001-11-21 | 2004-09-27 | Sunesis Pharmaceuticals Inc | Methods for ligand discovery |
| US20050084905A1 (en) | 2002-03-21 | 2005-04-21 | Prescott John C. | Identification of kinase inhibitors |
| GB2388594A (en) | 2002-05-16 | 2003-11-19 | Bayer Ag | Imidazo-triazine PDE 4 inhibitors |
| CA2494942A1 (en) | 2002-08-08 | 2004-02-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted benzimidazole compounds |
| UA80171C2 (en) * | 2002-12-19 | 2007-08-27 | Pfizer Prod Inc | Pyrrolopyrimidine derivatives |
| GB0303910D0 (en) | 2003-02-20 | 2003-03-26 | Merck Sharp & Dohme | Therapeutic agents |
| US7687506B2 (en) | 2003-04-11 | 2010-03-30 | The Regents Of The University Of California | Selective serine/threonine kinase inhibitors |
| WO2004100868A2 (en) | 2003-04-23 | 2004-11-25 | Abbott Laboratories | Method of treating transplant rejection |
| EP1473039A1 (en) | 2003-05-02 | 2004-11-03 | Centre National De La Recherche Scientifique (Cnrs) | Use of inhibitors and antisense oligonucleotides of BTK for the treatment of proliferative mastocytosis |
| US7405295B2 (en) | 2003-06-04 | 2008-07-29 | Cgi Pharmaceuticals, Inc. | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
| WO2005005429A1 (en) | 2003-06-30 | 2005-01-20 | Cellular Genomics, Inc. | Certain heterocyclic substituted imidazo[1,2-a]pyrazin-8-ylamines and methods of inhibition of bruton’s tyrosine kinase by such compounds |
| EP1664762A4 (en) | 2003-09-03 | 2008-08-13 | Us Gov Health & Human Serv | METHOD OF IDENTIFYING AND DIAGNOSIS OF, AND VIEWING, SURVIVAL IN LYMPHOMA |
| CN1897950A (zh) | 2003-10-14 | 2007-01-17 | 惠氏公司 | 稠合芳基和杂芳基衍生物及其使用方法 |
| SG132683A1 (en) | 2003-10-15 | 2007-06-28 | Osi Pharm Inc | Imidazopyrazine tyrosine kinase inhibitors |
| US20070196395A1 (en) | 2003-12-12 | 2007-08-23 | Mackerell Alexander | Immunomodulatory compounds that target and inhibit the py'binding site of tyrosene kinase p56 lck sh2 domain |
| US20070281907A1 (en) | 2003-12-22 | 2007-12-06 | Watkins William J | Kinase Inhibitor Phosphonate Conjugates |
| AU2005228845A1 (en) | 2004-01-26 | 2005-10-13 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| WO2005074603A2 (en) | 2004-02-03 | 2005-08-18 | Abbott Laboratories | Aminobenzoxazoles as therapeutic agents |
| ITMI20041314A1 (it) | 2004-06-30 | 2004-09-30 | Nuvera Fuel Cells Europ Srl | Dispositivo di raffreddamento per celle a combustibili a membrana |
| MY139689A (en) | 2004-07-20 | 2009-10-30 | Osi Pharm Inc | Imidazotriazines as protein kinase inhibitors |
| WO2006036726A1 (en) | 2004-09-22 | 2006-04-06 | Tripath Imaging, Inc. | Methods and computer program products for analysis and optimization of marker candidates for cancer prognosis |
| WO2006036941A2 (en) | 2004-09-27 | 2006-04-06 | Kosan Biosciences Incorporated | Specific kinase inhibitors |
| BRPI0516166A (pt) | 2004-09-28 | 2008-08-26 | Janssen Pharmaceutica Nv | antagonista do ccr2 de dipiperidina substituìda |
| KR20070119606A (ko) | 2004-11-10 | 2007-12-20 | 씨지아이 파마슈티칼스, 인크. | 특정 이미다조[１,２-ａ]피라진-８-일아민, 그의 제조 방법및 용도 |
| GB0425035D0 (en) | 2004-11-12 | 2004-12-15 | Novartis Ag | Organic compounds |
| KR100735639B1 (ko) | 2004-12-29 | 2007-07-04 | 한미약품 주식회사 | 암세포 성장 억제 효과를 갖는 퀴나졸린 유도체 및 이의제조방법 |
| MX2007009317A (es) | 2005-02-03 | 2008-01-30 | Gen Hospital Corp | Metodo para tratar cancer resistente a gefitinib. |
| WO2006099075A2 (en) | 2005-03-10 | 2006-09-21 | Cgi Pharmaceuticals, Inc. | Certain substituted amides, method of making, and method of use thereof |
| RU2411242C2 (ru) | 2005-05-13 | 2011-02-10 | Айрм, Ллк. | Соединения и композиции в качестве ингибиторов протеинкиназ |
| CN102603581B (zh) | 2005-06-22 | 2015-06-24 | 普莱希科公司 | 作为蛋白质激酶抑制剂的吡咯并[2,3-b]吡啶衍生物 |
| EP1957491A2 (en) | 2005-11-12 | 2008-08-20 | Boehringer Ingelheim International GmbH | Pyrrolo (2,3-b) pyridine derivatives useful as tec kinase inhibitors |
| BRPI0621027A2 (pt) | 2006-01-13 | 2011-11-29 | Pharmacyclics Inc | composto, composição farmacêutica |
| US7908091B2 (en) | 2006-03-17 | 2011-03-15 | Prometheus Laboratories Inc. | Methods of predicting and monitoring tyrosine kinase inhibitor therapy |
| KR20140019032A (ko) | 2006-04-05 | 2014-02-13 | 노파르티스 아게 | 암을 치료하기 위한 치료제의 조합물 |
| AU2007254179B2 (en) | 2006-05-18 | 2013-03-21 | Pharmacyclics Llc | Intracellular kinase inhibitors |
| NL2000640C2 (nl) | 2007-03-05 | 2008-09-08 | Stichting Wetsus Ct Of Excelle | Werkwijze en systeem voor het zuiveren van een vloeistof. |
| EP2546651A1 (en) | 2007-03-14 | 2013-01-16 | Bionsil S.r.l. | Modulator compounds of the drug resistance in epithelial tumour cells |
| ES2562215T3 (es) | 2007-03-28 | 2016-03-03 | Pharmacyclics Llc | Inhibidores de la tirosina quinasa de Bruton |
| US8809273B2 (en) | 2007-03-28 | 2014-08-19 | Pharmacyclics, Inc. | Inhibitors of Bruton's tyrosine kinase |
| US20120065201A1 (en) | 2007-03-28 | 2012-03-15 | Pharmacyclics, Inc. | Inhibitors of bruton's tyrosine kinase |
| AU2008236634A1 (en) | 2007-04-05 | 2008-10-16 | Aureon Laboratories, Inc. | Systems and methods for treating, diagnosing and predicting the occurrence of a medical condition |
| US7989465B2 (en) | 2007-10-19 | 2011-08-02 | Avila Therapeutics, Inc. | 4,6-disubstituted pyrimidines useful as kinase inhibitors |
| US8426441B2 (en) | 2007-12-14 | 2013-04-23 | Roche Palo Alto Llc | Inhibitors of bruton's tyrosine kinase |
| US20150152115A1 (en) | 2007-12-27 | 2015-06-04 | Pharmacyclics, Inc. | Inhibitors of bruton's tyrosine kinase |
| CN104926815B (zh) | 2008-01-04 | 2017-11-03 | 英特利凯恩有限责任公司 | 某些化学实体、组合物和方法 |
| CN102159214A (zh) | 2008-07-16 | 2011-08-17 | 药品循环公司 | 用于实体肿瘤的治疗的布鲁顿酪氨酸激酶的抑制剂 |
| JP2012504553A (ja) | 2008-07-29 | 2012-02-23 | フロンティア サイエンティフィック インコーポレイテッド | 微生物の殺滅または増殖抑制のためのテトラキス（ｎ−アルキルピリジニウム）−ポルフィリン誘導体の使用 |
| EP2352827A4 (en) | 2008-09-05 | 2016-07-20 | Celgene Avilomics Res Inc | ALGORITHM FOR DESIGNING IRREVERSIBLE INHIBITORS |
| US8426428B2 (en) | 2008-12-05 | 2013-04-23 | Principia Biopharma, Inc. | EGFR kinase knockdown via electrophilically enhanced inhibitors |
| US8299077B2 (en) | 2009-03-02 | 2012-10-30 | Roche Palo Alto Llc | Inhibitors of Bruton's tyrosine kinase |
| LU91583B1 (en) | 2009-07-03 | 2011-01-04 | Wurth Paul Sa | Sealing valve arrangement for a shaft furnace charging installation |
| TWI557127B (zh) | 2009-09-04 | 2016-11-11 | 百健Ｍａ公司 | 布魯頓氏酪胺酸激酶抑制劑 |
| CA2773848A1 (en) | 2009-09-09 | 2011-03-17 | Avila Therapeutics, Inc. | Pi3 kinase inhibitors and uses thereof |
| HRP20171537T1 (hr) | 2009-11-05 | 2017-12-15 | Rhizen Pharmaceuticals S.A. | Novi modulatori benzopiran kinaze |
| KR101537148B1 (ko) | 2010-05-31 | 2015-07-15 | 오노 야꾸힝 고교 가부시키가이샤 | 푸리논 유도체 |
| MX342405B (es) | 2010-06-03 | 2016-09-28 | Pharmacyclics Inc | El uso de inhibidores de la tirosina quinasa de bruton (btk). |
| US8957065B2 (en) | 2010-06-23 | 2015-02-17 | Hanmi Science Co., Ltd | Fused pyrimidine derivatives for inhibition of tyrosine kinase activity |
| US20120053189A1 (en) * | 2010-06-28 | 2012-03-01 | Pharmacyclics, Inc. | Btk inhibitors for the treatment of immune mediated conditions |
| CA2820709C (en) | 2011-02-28 | 2016-02-16 | Sunshine Lake Pharma Co., Ltd. | Substituted quinoline compounds and methods of use |
| BR112013029508B1 (pt) | 2011-05-17 | 2022-05-03 | Principia Biopharma, Inc. | Composto, composição farmacêutica, e, uso do referido composto |
| CN103534258B (zh) | 2011-05-17 | 2016-09-14 | 普林斯匹亚生物制药公司 | 酪氨酸激酶抑制剂 |
| US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| WO2013003629A2 (en) | 2011-06-28 | 2013-01-03 | Pharmacyclics, Inc. | Methods and compositions for inhibition of bone resorption |
| CN103857396A (zh) | 2011-07-13 | 2014-06-11 | 药品循环公司 | 布鲁顿酪氨酸激酶抑制剂 |
| SI3689878T1 (sl) | 2011-07-19 | 2021-12-31 | Merck Sharp & Dohme B.V. | 4-imidazopiridazin-1-il-benzamidi in 4-imidazotriazin-1-il-benzamidi kot Btk-zaviralci |
| EP2548877A1 (en) | 2011-07-19 | 2013-01-23 | MSD Oss B.V. | 4-(5-Membered fused pyridinyl)benzamides as BTK-inhibitors |
| JP6506555B2 (ja) | 2011-10-19 | 2019-04-24 | ファーマサイクリックス エルエルシー | ブルトン型チロシンキナーゼ（Ｂｔｋ）阻害剤の使用 |
| US8377946B1 (en) | 2011-12-30 | 2013-02-19 | Pharmacyclics, Inc. | Pyrazolo[3,4-d]pyrimidine and pyrrolo[2,3-d]pyrimidine compounds as kinase inhibitors |
| US8501724B1 (en) | 2012-01-31 | 2013-08-06 | Pharmacyclics, Inc. | Purinone compounds as kinase inhibitors |
| JP5514256B2 (ja) | 2012-05-18 | 2014-06-04 | 株式会社東芝 | 磁気記憶素子及びその製造方法 |
| KR20230170108A (ko) | 2012-06-04 | 2023-12-18 | 파마싸이클릭스 엘엘씨 | 브루톤 타이로신 키나아제 저해제의 결정 형태 |
| WO2013191965A1 (en) | 2012-06-18 | 2013-12-27 | Principia Biopharma Inc. | Reversible covalent pyrrolo- or pyrazolopyrimidines useful for the treatment cancer and autoimmune diseases |
| WO2014004707A1 (en) | 2012-06-29 | 2014-01-03 | Principia Biopharma Inc. | Formulations comprising ibrutinib |
| EP2878601B1 (en) | 2012-07-27 | 2018-03-28 | Riken | Agent for treating or controlling recurrence of acute myelogenous leukemia |
| WO2014022569A1 (en) | 2012-08-03 | 2014-02-06 | Principia Biopharma Inc. | Treatment of dry eye |
| BR112015011171A2 (pt) | 2012-11-15 | 2017-07-11 | Pharmacyclics Inc | compostos de pirrolopirimidina como inibidores da quinase |
| EP2948458B1 (en) | 2013-01-23 | 2019-05-01 | Merck Sharp & Dohme Corp. | Btk inhibitors |
| CA2902099C (en) | 2013-03-08 | 2020-06-02 | F. Hoffmann-La Roche Ag | Egfr mutation blood testing |
| MX369503B (es) | 2013-04-08 | 2019-11-11 | Pharmacyclics Llc | Combinaciones que comprenden ibrutinib y abt-199 para tratar trastornos proliferativos de células b y métodos de uso de las mismas. |
| US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| US9421208B2 (en) | 2013-08-02 | 2016-08-23 | Pharmacyclics Llc | Methods for the treatment of solid tumors |
| CA2920534A1 (en) | 2013-08-12 | 2015-02-19 | Pharmacyclics Llc | Methods for the treatment of her2 amplified cancer |
| EA201690618A1 (ru) | 2013-09-30 | 2016-09-30 | Фармасайкликс Элэлси | Ингибиторы тирозинкиназы брутона |
| EP3060251A4 (en) | 2013-10-25 | 2017-12-06 | Pharmacyclics LLC | Treatment using bruton's tyrosine kinase inhibitors and immunotherapy |
| US20150140036A1 (en) | 2013-11-13 | 2015-05-21 | Novartis Institutes For Biomedical Research, Inc. | Low, immune enhancing, dose mtor inhibitors and uses thereof |
| CN105949197A (zh) | 2014-01-29 | 2016-09-21 | 苏州晶云药物科技有限公司 | 依鲁替尼的新晶型及其制备方法 |
| WO2015127234A1 (en) | 2014-02-20 | 2015-08-27 | Board Of Regents, The University Of Texas System | Use of ibrutinib to treat egfr mutant cancer |
| US20150238490A1 (en) | 2014-02-21 | 2015-08-27 | Pharmacyclics, Inc. | Biomarkers for predicting response of dlbcl to treatment with ibrutinib |
| JP2017509336A (ja) | 2014-03-20 | 2017-04-06 | ファーマサイクリックス エルエルシー | ホスホリパーゼｃガンマ２及び耐性に関連した変異 |
| WO2016019233A1 (en) | 2014-08-01 | 2016-02-04 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
-
2012
- 2012-07-13 CN CN201280044640.1A patent/CN103857396A/zh active Pending
- 2012-07-13 BR BR112014000653A patent/BR112014000653A2/pt not_active IP Right Cessation
- 2012-07-13 KR KR20147003521A patent/KR20140048968A/ko not_active Withdrawn
- 2012-07-13 CA CA2841080A patent/CA2841080A1/en not_active Abandoned
- 2012-07-13 EP EP20120811600 patent/EP2731612A4/en not_active Withdrawn
- 2012-07-13 MX MX2014000518A patent/MX2014000518A/es unknown
- 2012-07-13 WO PCT/US2012/046779 patent/WO2013010136A2/en not_active Ceased
- 2012-07-13 EA EA201490265A patent/EA201490265A1/ru unknown
- 2012-07-13 PH PH1/2014/500122A patent/PH12014500122A1/en unknown
- 2012-07-13 AU AU2012283775A patent/AU2012283775A1/en not_active Abandoned
- 2012-07-13 US US13/549,267 patent/US9138436B2/en active Active
- 2012-07-13 JP JP2014520391A patent/JP2014520863A/ja active Pending
-
2014
- 2014-01-06 ZA ZA2014/00012A patent/ZA201400012B/en unknown
-
2015
- 2015-07-28 US US14/811,541 patent/US9862722B2/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005007085A2 (en) * | 2003-06-20 | 2005-01-27 | The Regents Of The University Of California | Pyrazolo pyrimidine derivatives and methods of use thereof |
| JP2008520744A (ja) * | 2004-11-19 | 2008-06-19 | ザ・レジェンツ・オブ・ザ・ユニバーシティ・オブ・カリフォルニア | 抗炎症性ピラゾロピリミジン |
| EP2201840A1 (en) * | 2006-09-22 | 2010-06-30 | Pharmacyclics, Inc. | Inhibitors of Bruton's Tyrosine Kinase |
| US20080214501A1 (en) * | 2006-11-03 | 2008-09-04 | Pharmacyclics, Inc. | Bruton's tyrosine kinase activity probe and method of using |
| JP2011503103A (ja) * | 2007-11-07 | 2011-01-27 | フォールドアールエックス ファーマシューティカルズ インコーポレーティッド | タンパク質輸送の調節方法 |
| WO2010045542A2 (en) * | 2008-10-16 | 2010-04-22 | The Regents Of The University Of California | Fused ring heteroaryl kinase inhibitors |
| US20110086866A1 (en) * | 2009-10-12 | 2011-04-14 | Pharmacyclics, Inc. | Inhibitors of bruton's tyrosine kinase |
Non-Patent Citations (2)
| Title |
|---|
| CHEMMEDCHEM, vol. 2, JPN6016006598, 2007, pages 58 - 61, ISSN: 0003262108 * |
| PROTEIN SCIENCE, vol. 19, JPN6016006599, 2010, pages 429 - 439, ISSN: 0003262109 * |
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|---|---|
| US20130018032A1 (en) | 2013-01-17 |
| MX2014000518A (es) | 2014-05-30 |
| WO2013010136A2 (en) | 2013-01-17 |
| US9138436B2 (en) | 2015-09-22 |
| EP2731612A2 (en) | 2014-05-21 |
| AU2012283775A1 (en) | 2014-01-23 |
| WO2013010136A3 (en) | 2013-07-04 |
| BR112014000653A2 (pt) | 2017-02-14 |
| US9862722B2 (en) | 2018-01-09 |
| EA201490265A1 (ru) | 2014-12-30 |
| US20150329550A1 (en) | 2015-11-19 |
| AU2012283775A8 (en) | 2014-02-20 |
| ZA201400012B (en) | 2016-01-27 |
| CN103857396A (zh) | 2014-06-11 |
| PH12014500122A1 (en) | 2014-03-24 |
| NZ619642A (en) | 2016-04-29 |
| EP2731612A4 (en) | 2015-04-08 |
| CA2841080A1 (en) | 2013-01-17 |
| KR20140048968A (ko) | 2014-04-24 |
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