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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| EA (1) | EA201490265A1 (enExample) |
| 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 |
| EA029000B1 (ru) | 2011-01-11 | 2018-01-31 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | КОМБИНАЦИЯ БОРТЕЗОМИДА И Akt-ИНГИБИТОРА ДЛЯ ЛЕЧЕНИЯ МНОЖЕСТВЕННОЙ МИЕЛОМЫ |
| US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| ES2604191T3 (es) | 2011-05-17 | 2017-03-03 | Principia Biopharma Inc. | Inhibidores de tirosina quinasas |
| EP2723746A1 (en) | 2011-06-22 | 2014-04-30 | Vertex Pharmaceuticals Inc. | Compounds useful as inhibitors of atr kinase |
| 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 |
| EP2548877A1 (en) | 2011-07-19 | 2013-01-23 | MSD Oss B.V. | 4-(5-Membered fused pyridinyl)benzamides as BTK-inhibitors |
| EP2734522B1 (en) | 2011-07-19 | 2018-10-31 | Merck Sharp & Dohme B.V. | 4-imidazopyridazin-1-yl-benzamides and 4-imidazotriazin-1-yl-benzamides as btk-inhibitors |
| EP3409278B8 (en) | 2011-07-21 | 2020-11-04 | Sumitomo Dainippon Pharma Oncology, Inc. | Heterocyclic protein kinase inhibitors |
| 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 |
| BR112015003859B1 (pt) | 2012-09-10 | 2023-04-11 | Principia Biopharma Inc. | Composto e/ou sal farmaceuticamente aceitável do mesmo, respectivo uso e composição farmacêutica |
| EP4534538A3 (en) | 2012-12-07 | 2025-06-11 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| CA2904055A1 (en) * | 2013-03-06 | 2014-09-12 | 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 |
| HUE044558T2 (hu) | 2013-03-14 | 2019-11-28 | Tolero Pharmaceuticals Inc | JAK és ALK2 inhibitorok és eljárások alkalmazásukra |
| WO2014143241A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of atr kinase |
| EA201591685A1 (ru) * | 2013-03-15 | 2016-01-29 | Янссен Фармацевтика Нв | Способы и промежуточные соединения для получения лекарственного препарата |
| US8969360B2 (en) | 2013-03-15 | 2015-03-03 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| WO2014143240A1 (en) | 2013-03-15 | 2014-09-18 | Vertex Pharmaceuticals Incorporated | Fused pyrazolopyrimidine derivatives useful as inhibitors of atr kinase |
| 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 |
| US9694011B2 (en) * | 2013-05-21 | 2017-07-04 | Jiangsu Medolution Ltd | Substituted pyrazolopyrimidines as kinases inhibitors |
| US9580432B2 (en) * | 2013-08-12 | 2017-02-28 | Taiho Pharmaceutical Co., Ltd. | Fused pyrimidine compound or salt thereof |
| MA38961A1 (fr) * | 2013-09-30 | 2018-05-31 | Pharmacyclics Llc | Composés 3-phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-ylamine substitués inhibiteurs de la tyrosine kinase de bruton utilisés pour traiter par exemple les maladies auto-immunes, respiratoires et inflammatoires, cancer, mastocytose et osteoporose |
| 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 |
| AU2014358868A1 (en) | 2013-12-05 | 2016-06-09 | Acerta Pharma B.V. | Therapeutic combination of a PI3K inhibitor and a BTK inhibitor |
| CA2932757C (en) | 2013-12-06 | 2023-10-31 | Vertex Pharmaceuticals Incorporated | 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 |
| CA2939186C (en) | 2014-02-21 | 2023-03-07 | Principia Biopharma Inc. | Salts and solid form of a btk inhibitor |
| CN106456642A (zh) | 2014-03-12 | 2017-02-22 | 诺华股份有限公司 | 含btk抑制剂与akt抑制剂的组合 |
| 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 |
| RU2719583C2 (ru) | 2014-06-05 | 2020-04-21 | Вертекс Фармасьютикалз Инкорпорейтед | Радиоактивно меченные производные 2-амино-6-фтор-n-[5-фтор-пиридин-3-ил]-пиразоло[1, 5-а]пиримидин-3-карбоксамида, используемые в качестве ингибитора atr киназы, препараты на основе этого соединения и его различные твердые формы |
| GB201410430D0 (en) * | 2014-06-11 | 2014-07-23 | Redx Pharma Ltd | Compounds |
| SG11201610500WA (en) | 2014-06-17 | 2017-01-27 | Vertex Pharma | Method for treating cancer using a combination of chk1 and atr inhibitors |
| 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 |
| AT515941B1 (de) | 2014-07-29 | 2016-01-15 | Avl List Gmbh | Kondensationspartikelzähler mit einer Sättigungseinheit und einer nachgeschalteten Kondensationseinheit |
| EP3174539A4 (en) | 2014-08-01 | 2017-12-13 | Pharmacyclics, LLC | Inhibitors of bruton's tyrosine kinase |
| ES2900184T3 (es) | 2014-08-11 | 2022-03-16 | Acerta Pharma Bv | Combinaciones terapéuticas de un inhibidor de BTK y un inhibidor 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 |
| 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 |
| 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 |
| 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 |
| WO2016210165A1 (en) | 2015-06-24 | 2016-12-29 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| DK3317281T3 (da) | 2015-07-02 | 2020-06-15 | Acerta Pharma Bv | Faste former og formuleringer af (s)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-n-(pyridin-2-yl)benzamid |
| 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 |
| PT3345907T (pt) * | 2015-09-01 | 2020-06-23 | Taiho Pharmaceutical Co Ltd | Compostos de pirazolo[3,4-d]pirimidina ou sais dos mesmos |
| KR102678021B1 (ko) | 2015-09-30 | 2024-06-26 | 버텍스 파마슈티칼스 인코포레이티드 | Dna 손상제와 병용되는, atr 저해제를 포함하는 암 치료용 약제학적 조성물 |
| MX380907B (es) | 2015-12-16 | 2025-03-12 | Loxo Oncology Inc | Compuestos útiles como inhibidores de cinasa. |
| EA039213B1 (ru) | 2015-12-24 | 2021-12-17 | Такеда Фармасьютикал Компани Лимитед | Сокристалл, способ его получения и лекарственное средство, содержащее сокристалл |
| 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 |
| IL293621B2 (en) | 2016-06-29 | 2023-09-01 | Principia Biopharma Inc | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[4,3-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4 -Methyl-4-[4-(oxane-3-yl)piperazine-1-yl)penta-2-ananitrile |
| JP6737952B2 (ja) * | 2016-08-17 | 2020-08-12 | 深▲セン▼市塔吉瑞生物医▲薬▼有限公司Ｓｈｅｎｚｈｅｎ ＴａｒｇｅｔＲｘ，Ｉｎｃ． | チロシンキナーゼ活性を阻害するための縮合二環式化合物 |
| 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 |
| US11518761B2 (en) | 2017-08-17 | 2022-12-06 | Vyera Pharmaceuticals, LLC | CDPK1 inhibitors, compositions, and methods related thereto |
| 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 |
| WO2019195753A1 (en) | 2018-04-05 | 2019-10-10 | Tolero Pharmaceuticals, Inc. | Axl kinase inhibitors and use of the same |
| US20210113562A1 (en) | 2018-04-13 | 2021-04-22 | Sumitomo Dainippon Pharma Oncology, Inc. | Pim kinase inhibitors for treatment of myeloproliferative neoplasms and fibrosis associated with cancer |
| MX2021000977A (es) | 2018-07-26 | 2021-04-12 | Sumitomo Pharma Oncology Inc | Metodos para tratar enfermedades asociadas con expresion anormal de receptor de activina a tipo 1 (acvr1) e inhibidores de acvr1 para uso en los mismos. |
| JP7662528B2 (ja) | 2019-02-12 | 2025-04-15 | スミトモ ファーマ アメリカ， インコーポレイテッド | 複素環式タンパク質キナーゼ阻害剤を含む製剤 |
| US20210106584A1 (en) | 2019-10-14 | 2021-04-15 | Principia Biopharma Inc. | Methods for treating immune thrombocytopenia by administering (r)-2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile |
| TW202140484A (zh) | 2020-01-22 | 2021-11-01 | 美商普林斯匹亞生物製藥公司 | ２－［３－［４－胺基－３－（２－氟－４－苯氧基－苯基）－１Ｈ－吡唑并［３，４－ｄ］嘧啶－１－基］哌啶－１－羰基］－４－甲基－４－［４－（氧環丁烷－３－基）哌𠯤－１－基］戊－２－烯腈之晶形 |
| CN113336760B (zh) * | 2020-02-18 | 2022-11-04 | 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 |
| JP2024517963A (ja) | 2021-05-14 | 2024-04-23 | ロクソ オンコロジー， インコーポレイテッド | ブルトン型チロシンキナーゼ阻害剤の共結晶形態 |
| WO2024097653A1 (en) | 2022-10-31 | 2024-05-10 | Sumitomo Pharma America, Inc. | Pim1 inhibitor for treating myeloproliferative neoplasms |
| 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 |
| PT970084E (pt) | 1997-03-19 | 2003-10-31 | Abbott Gmbh & Co Kg | Pirrolo¬2,3d|pirimidinas e sua utilizacao como inibidores da tirosina-cinase |
| US6303652B1 (en) | 1998-08-21 | 2001-10-16 | Hughes Institute | BTK inhibitors and methods for their identification and use |
| EP1071658B1 (en) | 1998-04-17 | 2004-06-16 | Parker Hughes Institute | Btk inhibitors and methods for their identification and use |
| 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 |
| 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 |
| US6713474B2 (en) | 1998-09-18 | 2004-03-30 | Abbott Gmbh & Co. Kg | Pyrrolopyrimidines as therapeutic agents |
| WO2000017203A1 (en) | 1998-09-18 | 2000-03-30 | Basf Aktiengesellschaft | Pyrrolopyrimidines as protein kinase inhibitors |
| US6306897B1 (en) | 1999-03-19 | 2001-10-23 | Parker Hughes Institute | Calanolides for inhibiting BTK |
| IL148718A0 (en) | 1999-09-17 | 2002-09-12 | Abbott Gmbh & Co Kg | Pyrazolopyrimidines as therapeutic agents |
| US6921763B2 (en) | 1999-09-17 | 2005-07-26 | Abbott Laboratories | Pyrazolopyrimidines as therapeutic agents |
| ES2225231T3 (es) | 1999-10-06 | 2005-03-16 | Boehringer Ingelheim Pharmaceuticals Inc. | Compuestos heterociclicos, utiles como inhibidores de tirosina quinasas. |
| US6506769B2 (en) | 1999-10-06 | 2003-01-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Heterocyclic compounds useful as inhibitors of tyrosine kinases |
| AU4508601A (en) | 1999-11-30 | 2001-06-18 | Parker Hughes Institute | Inhibitors of collagen-induced platelet aggregation |
| WO2001044258A1 (en) | 1999-12-17 | 2001-06-21 | 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 |
| JP2004533209A (ja) | 2000-10-23 | 2004-11-04 | ブリストル−マイヤーズ スクイブ カンパニー | ブルトンチロシンキナーゼおよびブルトンチロシンキナーゼ媒体のモデュレーターおよびその同定方法および骨粗鬆症および関連疾患状態の治療および予防におけるその使用 |
| US20030035833A1 (en) | 2000-12-06 | 2003-02-20 | Xiaorong He | Rapidly dispersing pharmaceutical composition |
| 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 |
| AU2002315389A1 (en) | 2001-06-21 | 2003-01-08 | Ariad Pharmaceuticals, Inc. | Novel pyrazolo-and pyrrolo-pyrimidines and uses thereof |
| CA2450777C (en) | 2001-08-10 | 2013-04-09 | Novartis Ag | Use of c-src inhibitors alone or in combination with sti571 for the treatment of leukaemia |
| WO2003016338A1 (en) | 2001-08-15 | 2003-02-27 | Parker Hughes Institute | Crystal structure of the btk kinase domain |
| EP1939625A3 (en) | 2001-11-21 | 2008-09-03 | 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 |
| AU2003257094A1 (en) | 2002-08-08 | 2004-02-25 | 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 |
| US20050008640A1 (en) | 2003-04-23 | 2005-01-13 | Wendy Waegell | 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 |
| WO2005014599A1 (en) | 2003-06-04 | 2005-02-17 | Cellular Genomics, Inc. | Imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of bruton’s tyrosine kinase by such compounds |
| US7393848B2 (en) | 2003-06-30 | 2008-07-01 | Cgi Pharmaceuticals, Inc. | Certain heterocyclic substituted imidazo[1,2-A]pyrazin-8-ylamines and methods of inhibition of Bruton's tyrosine kinase by such compounds |
| EP2157524A3 (en) | 2003-09-03 | 2010-12-08 | GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | Methods for identifying, diagnosing, and predicting survival of lymphomas |
| 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 |
| JP4916883B2 (ja) | 2003-10-15 | 2012-04-18 | オーエスアイ・ファーマスーティカルズ・インコーポレーテッド | イミダゾピラジンチロシンキナーゼ阻害剤 |
| 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 |
| BRPI0418031A (pt) | 2003-12-22 | 2007-04-17 | Gilead Sciences Inc | inibidores de quinase fosfonato-substituìdos |
| US7855214B2 (en) | 2004-01-26 | 2010-12-21 | Vertex Pharmaceuticals Incorporated | Fused cyclic systems useful as inhibitors of TEC family protein kinases |
| US20060025383A1 (en) | 2004-02-03 | 2006-02-02 | Neil Wishart | 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 |
| AR053090A1 (es) | 2004-07-20 | 2007-04-25 | Osi Pharm Inc | Imidazotriazinas como inhibidores de proteina quinasas y su uso para la preparacion de medicamentos |
| KR20070061893A (ko) | 2004-09-22 | 2007-06-14 | 트리패스 이미징, 인코포레이티드 | 유방암 예후를 평가하기 위한 방법 및 조성물 |
| EP1794137A4 (en) | 2004-09-27 | 2009-12-02 | Kosan Biosciences Inc | SPECIFIC KINASE INHIBITORS |
| MX2007003793A (es) | 2004-09-28 | 2007-07-11 | Johnson & Johnson | Antagonistas del receptor 2 de citocina quimioatrayente de dipiperidina sustituida. |
| BRPI0517619A (pt) | 2004-11-10 | 2008-10-14 | Cgi Pharmaceuticals Inc | entidades quìmicas de imidazo[1,2-a] pirazin-8-ilaminas, suas composições farmacêuticas, uso dos referidos compostos na preparação de medicamento, processo de preparação de medicamento e métodos de utilização dos referidos compostos |
| 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 |
| DE602006021142D1 (de) | 2005-02-03 | 2011-05-19 | Gen Hospital Corp | Verfahren zur behandlung von gefitinib-resistentem krebs |
| JP2008533032A (ja) | 2005-03-10 | 2008-08-21 | シージーアイ ファーマシューティカルズ，インコーポレイティド | 或る種の置換アミド、その製造方法及び使用方法 |
| PL1891066T3 (pl) | 2005-05-13 | 2011-05-31 | Irm Llc | Związki i kompozycje jako inhibitory kinazy białkowej |
| BRPI0611863B1 (pt) | 2005-06-22 | 2021-11-23 | Plexxikon, Inc | Composto, bem como composição e kit compreendendo o mesmo, composto intermediário na preparação do mesmo, método para tratamento e uso do mesmo |
| CA2629314A1 (en) | 2005-11-12 | 2007-05-24 | Boehringer Ingelheim International Gmbh | Tec kinase inhibitors |
| CN101421269A (zh) | 2006-01-13 | 2009-04-29 | 环状药物公司 | 酪氨酸激酶抑制剂及其用途 |
| WO2007109571A2 (en) | 2006-03-17 | 2007-09-27 | Prometheus Laboratories, Inc. | Methods of predicting and monitoring tyrosine kinase inhibitor therapy |
| EP2004163B1 (en) | 2006-04-05 | 2014-09-17 | Novartis Pharma AG | Combination of everolimus and vinorelbine |
| CA2858520A1 (en) | 2006-05-18 | 2007-11-29 | Pharmacyclics Inc. | 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. |
| RS53165B (sr) | 2007-03-14 | 2014-06-30 | Bionsil S.R.L. | Inhibitori btk za lečenje epitelnih tumora rezistentnih na hemoterapijske lekove |
| US20120065201A1 (en) | 2007-03-28 | 2012-03-15 | Pharmacyclics, Inc. | Inhibitors of bruton's tyrosine kinase |
| US8809273B2 (en) | 2007-03-28 | 2014-08-19 | Pharmacyclics, Inc. | Inhibitors of Bruton's tyrosine kinase |
| CN103319488A (zh) * | 2007-03-28 | 2013-09-25 | 环状药物公司 | 布鲁顿氏酪氨酸激酶抑制剂 |
| US20100088264A1 (en) | 2007-04-05 | 2010-04-08 | 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 |
| MX2010007418A (es) | 2008-01-04 | 2010-11-12 | Intellikine Inc | Ciertas entidades quimicas, composiciones y metodos. |
| MX2011000661A (es) | 2008-07-16 | 2011-05-25 | Pharmacyclics Inc | Inhibidores de tirosina cinasa de bruton para el tratamiento de tumores solidos. |
| ES2620442T3 (es) | 2008-07-29 | 2017-06-28 | Frontier Scientific, Inc. | Uso de derivados de tetraquis(N-alquilpiridinio)-porfirina para la destrucción de microbios o la prevención de su crecimiento |
| WO2010028236A1 (en) | 2008-09-05 | 2010-03-11 | Avila Therapeutics, 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 |
| EP2496567B1 (en) | 2009-11-05 | 2017-07-12 | Rhizen Pharmaceuticals S.A. | Novel benzopyran kinase modulators |
| BR112012030711B1 (pt) | 2010-05-31 | 2020-10-13 | Ono Pharmaceutical Co. Ltd | derivado de purinona |
| EP2575818A4 (en) | 2010-06-03 | 2013-11-06 | Pharmacyclics Inc | USE OF BRUTON TYROSINE KINASE INHIBITORS (BTK) |
| CN105061438B (zh) | 2010-06-23 | 2017-07-04 | 韩美科学株式会社 | 用于抑制酪氨酸激酶活性的稠合嘧啶衍生物 |
| 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 |
| US9376438B2 (en) | 2011-05-17 | 2016-06-28 | Principia Biopharma, Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| ES2604191T3 (es) | 2011-05-17 | 2017-03-03 | Principia Biopharma Inc. | Inhibidores de tirosina quinasas |
| MX355728B (es) | 2011-05-17 | 2018-04-27 | Univ California | Inhibidores de cinasas. |
| 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 |
| EP2548877A1 (en) | 2011-07-19 | 2013-01-23 | MSD Oss B.V. | 4-(5-Membered fused pyridinyl)benzamides as BTK-inhibitors |
| EP2734522B1 (en) | 2011-07-19 | 2018-10-31 | Merck Sharp & Dohme B.V. | 4-imidazopyridazin-1-yl-benzamides and 4-imidazotriazin-1-yl-benzamides as btk-inhibitors |
| WO2013059738A2 (en) | 2011-10-19 | 2013-04-25 | Pharmacyclics, Inc. | Use of inhibitors of bruton's tyrosine kinase (btk) |
| 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 |
| CA2875986C (en) | 2012-06-04 | 2020-06-09 | Pharmacyclics, Inc. | Crystalline forms of a bruton's tyrosine kinase inhibitor |
| WO2013191965A1 (en) | 2012-06-18 | 2013-12-27 | Principia Biopharma Inc. | Reversible covalent pyrrolo- or pyrazolopyrimidines useful for the treatment cancer and autoimmune diseases |
| US20150140085A1 (en) | 2012-06-29 | 2015-05-21 | Principia Biopharma Inc. | Formulations comprising ibrutinib |
| WO2014017659A1 (ja) | 2012-07-27 | 2014-01-30 | 独立行政法人理化学研究所 | 急性骨髄性白血病の治療又は再発抑制剤 |
| US9572811B2 (en) | 2012-08-03 | 2017-02-21 | Principia Biopharma Inc. | Treatment of dry eye |
| KR20150084923A (ko) | 2012-11-15 | 2015-07-22 | 파마시클릭스, 인코포레이티드 | 키나제 억제제로서의 피롤로피리미딘 화합물 |
| 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 |
| MA38961A1 (fr) | 2013-09-30 | 2018-05-31 | Pharmacyclics Llc | Composés 3-phenyl-1h-pyrazolo[3,4-d]pyrimidin-4-ylamine substitués inhibiteurs de la tyrosine kinase de bruton utilisés pour traiter par exemple les maladies auto-immunes, respiratoires et inflammatoires, cancer, mastocytose et osteoporose |
| MX2016005283A (es) | 2013-10-25 | 2017-02-20 | Pharmacyclics Llc | Tratamiento que utiliza inhibidores de tirosina quinasa de bruton e inmunoterapia. |
| EP3068435A1 (en) | 2013-11-13 | 2016-09-21 | Novartis AG | Mtor inhibitors for enhancing the immune response |
| CN106008521A (zh) | 2014-01-29 | 2016-10-12 | 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 |
| EP3174539A4 (en) | 2014-08-01 | 2017-12-13 | Pharmacyclics, LLC | Inhibitors of bruton's tyrosine kinase |
-
2012
- 2012-07-13 CN CN201280044640.1A patent/CN103857396A/zh active Pending
- 2012-07-13 WO PCT/US2012/046779 patent/WO2013010136A2/en not_active Ceased
- 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 KR KR20147003521A patent/KR20140048968A/ko not_active Withdrawn
- 2012-07-13 EP EP20120811600 patent/EP2731612A4/en not_active Withdrawn
- 2012-07-13 JP JP2014520391A patent/JP2014520863A/ja active Pending
- 2012-07-13 EA EA201490265A patent/EA201490265A1/ru unknown
- 2012-07-13 MX MX2014000518A patent/MX2014000518A/es unknown
- 2012-07-13 PH PH1/2014/500122A patent/PH12014500122A1/en unknown
- 2012-07-13 BR BR112014000653A patent/BR112014000653A2/pt not_active IP Right Cessation
- 2012-07-13 CA CA2841080A patent/CA2841080A1/en not_active Abandoned
-
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- 2014-01-06 ZA ZA2014/00012A patent/ZA201400012B/en unknown
-
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- 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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| AU2012283775A8 (en) | 2014-02-20 |
| WO2013010136A3 (en) | 2013-07-04 |
| US9862722B2 (en) | 2018-01-09 |
| PH12014500122A1 (en) | 2014-03-24 |
| ZA201400012B (en) | 2016-01-27 |
| MX2014000518A (es) | 2014-05-30 |
| EP2731612A4 (en) | 2015-04-08 |
| AU2012283775A1 (en) | 2014-01-23 |
| EA201490265A1 (ru) | 2014-12-30 |
| US9138436B2 (en) | 2015-09-22 |
| CN103857396A (zh) | 2014-06-11 |
| CA2841080A1 (en) | 2013-01-17 |
| NZ619642A (en) | 2016-04-29 |
| EP2731612A2 (en) | 2014-05-21 |
| US20130018032A1 (en) | 2013-01-17 |
| KR20140048968A (ko) | 2014-04-24 |
| WO2013010136A2 (en) | 2013-01-17 |
| US20150329550A1 (en) | 2015-11-19 |
| BR112014000653A2 (pt) | 2017-02-14 |
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