PT2194987T - Novos inibidores da via stat3 e de células estaminais cancerígenas - Google Patents
Novos inibidores da via stat3 e de células estaminais cancerígenas Download PDFInfo
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- PT2194987T PT2194987T PT88304712T PT08830471T PT2194987T PT 2194987 T PT2194987 T PT 2194987T PT 88304712 T PT88304712 T PT 88304712T PT 08830471 T PT08830471 T PT 08830471T PT 2194987 T PT2194987 T PT 2194987T
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| EP2542155B1 (en) | 2010-03-01 | 2015-11-04 | TAU Therapeutics LLC | Method for imaging a disease |
| LT2547205T (lt) | 2010-03-19 | 2024-06-10 | 1Globe Biomedical Co., Ltd. | Nauji tikslinio poveikio vėžio kamieninėms ląstelėms būdai |
| AU2015218436B9 (en) * | 2010-03-19 | 2017-03-09 | Boston Biomedical, Inc. | Novel Methods For Targeting Cancer Stem Cells |
| EP3108750B1 (en) * | 2010-03-19 | 2018-07-04 | 1Globe Biomedical Co., Ltd. | Novel compounds and compositions for targeting cancer stem cells |
| MX394137B (es) | 2010-03-19 | 2025-03-24 | Boston Biomedical Inc | Compuestos y composiciones novedosas para atacar las células madre del cáncer. |
| WO2011130677A1 (en) * | 2010-04-16 | 2011-10-20 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Inhibitors of cancer stem cells |
| US20110301194A1 (en) * | 2010-06-02 | 2011-12-08 | Arqule, Inc. | Method for Determining Treatment Efficacy |
| CN103153975B (zh) * | 2010-08-24 | 2016-01-20 | 杭州益尔生物科技有限公司 | 用于疾病治疗的新型萘醌 |
| EP2617435A4 (en) * | 2010-09-16 | 2014-03-12 | Univ Osaka | THERAPEUTICS AND PROPHYLACTIC AGENTS FOR COMPOSITIONS OF AUTOIMMUNE DISEASES, INFLAMMATORY DISEASES, ALLERGIC DISEASES AND ORGAN TRANSPLANTS |
| EP2643001A4 (en) * | 2010-11-22 | 2014-02-19 | Glaxosmithkline Ip Dev Ltd | METHOD OF TREATING CANCER |
| WO2012071648A1 (en) * | 2010-11-30 | 2012-06-07 | London Health Sciences Centre Research Inc. | Egfr antagonist for the treatment of heart disease |
| WO2012078982A2 (en) * | 2010-12-09 | 2012-06-14 | The Ohio State University | Xzh-5 inhibits constitutive and interleukin-6-induced stat3 phosphorylation in human hepatocellular carcinoma cells |
| CN103402993A (zh) * | 2011-03-04 | 2013-11-20 | 舟山海中洲新生药业有限公司 | 用于疾病治疗的4，9-二羟基-萘并[2,3-b] 呋喃新型酯 |
| KR20120130658A (ko) * | 2011-05-23 | 2012-12-03 | 주식회사 파멥신 | 펩타이드가 융합된 이중표적항체 및 그 용도 |
| EP3251671A1 (en) * | 2011-06-06 | 2017-12-06 | Akebia Therapeutics Inc. | Compositions for stabilizing hypoxia inducible factor-2 alpha as a method for treating cancer |
| SG10201601917XA (en) * | 2011-09-12 | 2016-04-28 | Tau Therapeutics Llc | Antagonists of products of the hs.459642 unigene cluster for the inhibition of proliferation, development or differentiation of stem cells including cancer stem cells |
| EP2776586B1 (en) * | 2011-11-11 | 2018-03-07 | Millennium Pharmaceuticals, Inc. | Biomarkers of response to proteasome inhibitors |
| JP2015506990A (ja) * | 2012-02-17 | 2015-03-05 | ゾウシャン ハイジョンジョウ シンシェン ファーマシューティカルズ カンパニー リミテッドＺｈｏｕｓｈａｎ Ｈａｉｚｈｏｎｇｚｈｏｕ Ｘｉｎｓｈｅｎｇ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｃｏ．， Ｌｔｄ． | ４，９−ジヒドロキシ−ナフト［２，３−ｂ］フラン脂肪族酸エステルの誘導体の水性ナノ粒子懸濁液を調製する方法 |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2013166618A1 (en) * | 2012-05-08 | 2013-11-14 | Zhoushan Haizhongzhou Xinsheng Pharmaceuticals Co., Ltd. | PRODRUGS OF 4,9-DIHYDROXY-NAPHTHO[2,3-b]FURANS FOR CIRCUMVENTING CANCER MULTIDRUG RESISTANCE |
| SG10201805807PA (en) | 2012-06-26 | 2018-08-30 | Del Mar Pharmaceuticals | Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof |
| CN106421795A (zh) * | 2012-10-08 | 2017-02-22 | 贾力 | 预防原发性肿瘤在手术切除后再转移的药用组合物 |
| DE102013003107A1 (de) | 2013-02-25 | 2014-09-11 | Thomas Rühl | Naphthofurandione mit einer 1-Bromalkylgruppe oder einer 1-Hydroxyalkylgruppe in 2-Position und einer Alkylgruppe in 3-Position zum Furanring-Sauerstoff und Verfahren zu deren Herstellung |
| CN105492011A (zh) | 2013-04-08 | 2016-04-13 | 丹尼斯·M·布朗 | 不理想给药化学化合物的治疗增效 |
| MX2015014181A (es) * | 2013-04-09 | 2016-05-24 | Boston Biomedical Inc | 2-acetilnafto [2,3-b]furano -4,9-diona para uso en el tratamiento del cáncer. |
| EP2992018B1 (en) | 2013-04-29 | 2019-02-13 | OGD2 Pharma | Targeting o-acetylated gd2 ganglioside as a new therapeutic and diagnostic strategy for cancer stem cells cancer |
| US10745489B2 (en) | 2013-04-29 | 2020-08-18 | Ogd2 Pharma | Targeting o-acetylated gd2 ganglioside as a new therapeutic and diagnostic strategy for Cancer Stem Cells cancer |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| PH12016500582B1 (en) | 2013-10-04 | 2023-06-30 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
| RU2016128396A (ru) * | 2014-01-27 | 2018-03-02 | Бостон Биомедикал, Инк. | Новые способы лечения рака |
| EP3102036A4 (en) * | 2014-02-07 | 2017-09-20 | Boston Biomedical, Inc. | 3-substituted carbonyl-naphtho[2,3-b]furane derivative or pharmaceutically acceptable salt thereof |
| US11406707B2 (en) | 2014-02-10 | 2022-08-09 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | STAT3 phosphorylation during graft-versus-host disease |
| JP6701088B2 (ja) | 2014-03-19 | 2020-05-27 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | Ｐｉ３ｋ−ガンマ媒介障害の治療で使用するための複素環式化合物 |
| JP6894236B2 (ja) * | 2014-03-26 | 2021-06-30 | デノボ バイオファーマ エルエルシー | 免疫刺激活性を有するレトロウイルスベクター |
| WO2015164870A1 (en) | 2014-04-25 | 2015-10-29 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Gamma-aa-peptide stat3/dna inhibitors and methods of use |
| WO2015171985A1 (en) * | 2014-05-09 | 2015-11-12 | The Brigham And Women's Hospital, Inc. | Treatment of igg-immune complex-mediated organ damage |
| ES2792851T3 (es) * | 2014-06-09 | 2020-11-12 | Kyoto Pharma Ind | Derivados de naftofurano para uso como agentes antineoplásicos |
| US10869926B2 (en) * | 2014-07-15 | 2020-12-22 | The Johns Hopkins University | Suppression of myeloid derived suppressor cells and immune checkpoint blockade |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| KR20160066490A (ko) * | 2014-12-02 | 2016-06-10 | 주식회사 씨앤드씨신약연구소 | 헤테로사이클 유도체 및 그의 용도 |
| US10906914B2 (en) | 2015-01-08 | 2021-02-02 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Furoquinolinediones as inhibitors of TDP2 |
| JP6630364B2 (ja) | 2015-03-27 | 2020-01-15 | ボストン バイオメディカル， インコーポレイテッド | 水溶性プロドラッグ |
| CN104725480A (zh) * | 2015-04-06 | 2015-06-24 | 苏州普罗达生物科技有限公司 | 一种信号传导及转录激活因子抑制多肽及其应用 |
| CN104693279A (zh) * | 2015-04-06 | 2015-06-10 | 苏州普罗达生物科技有限公司 | 关于信号传导及转录激活因子抑制多肽及其应用 |
| CN104693280A (zh) * | 2015-04-06 | 2015-06-10 | 苏州普罗达生物科技有限公司 | 信号传导及转录激活因子抑制多肽及其应用 |
| BR112017022281A2 (pt) * | 2015-04-17 | 2018-07-10 | Boston Biomedical Inc | métodos para tratar câncer |
| TW201713328A (zh) * | 2015-04-17 | 2017-04-16 | 波士頓生醫公司 | 治療癌症之方法 |
| MX2017013358A (es) * | 2015-04-17 | 2018-08-01 | Boston Biomedical Inc | Métodos para tratar el cáncer. |
| BR112017022958A2 (pt) * | 2015-04-27 | 2018-07-17 | Boston Biomedical Inc | métodos para tratamento de câncer com inibidor da via da stat3 e inibidor de quinase |
| RS57371B1 (sr) * | 2015-05-14 | 2018-08-31 | NuCana plc | Tretman kancera |
| EP3294299A1 (en) * | 2015-05-15 | 2018-03-21 | Novartis AG | Methods for treating egfr mutant cancers |
| WO2016196935A1 (en) * | 2015-06-03 | 2016-12-08 | Boston Biomedical, Inc. | Compositions comprising a cancer stemness inhibitor and an immunotherapeutic agent for use in treating cancer |
| US10329267B2 (en) | 2015-07-17 | 2019-06-25 | Sumitomo Dainippon Pharma Co., Ltd. | Method for producing 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione |
| WO2017013270A1 (en) | 2015-07-23 | 2017-01-26 | Universite De Strasbourg | Use of leptin signaling inhibitor for protecting kidneys from patients having ciliopathy |
| WO2017023866A1 (en) * | 2015-07-31 | 2017-02-09 | Boston Biomedical, Inc. | Method of targeting stat3 and other non-druggable proteins |
| AU2016322552B2 (en) | 2015-09-14 | 2021-03-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| PH12018500691B1 (en) | 2015-10-05 | 2022-08-10 | NuCana plc | Combination therapy |
| US20190017054A1 (en) * | 2016-01-07 | 2019-01-17 | Luni Emdad | Method of modulating survival and stemness of cancer stem cells by mda-9/syntenin (sdcbp) |
| WO2017132049A1 (en) | 2016-01-20 | 2017-08-03 | Boston Biomedical, Inc. | Methods for treating cancer |
| CN109104862A (zh) * | 2016-03-01 | 2018-12-28 | 中央研究院 | 4,9-二氧代-4,9-二氢萘并[2,3-b]呋喃-3-羧酰胺衍生物及其用于治疗增生性疾病与感染性疾病的用途 |
| US11946927B2 (en) | 2016-03-14 | 2024-04-02 | Musidora Biotechnology Llc | Process and system for identifying individuals having a high risk of inflammatory bowel disease and a method of treatment |
| US10295527B2 (en) | 2016-03-14 | 2019-05-21 | Bruce Yacyshyn | Process and system for predicting responders and non-responders to mesalamine treatment of ulcerative colitis |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
| WO2017164379A1 (ja) * | 2016-03-25 | 2017-09-28 | 大日本住友製薬株式会社 | ２－アルキルカルボニルナフト［２，３－ｂ］フラン－４，９－ジオンの関連物質の製造方法、及びその関連物質 |
| JP2017171640A (ja) * | 2016-03-25 | 2017-09-28 | 学校法人兵庫医科大学 | 癌の治療システム |
| CN105837541A (zh) * | 2016-04-23 | 2016-08-10 | 何淑琼 | 磷酸苯丙哌林的药物组合物及其在生物医药中的应用 |
| CN105906595A (zh) * | 2016-04-23 | 2016-08-31 | 陈斌 | 丙酸倍氯米松的药物组合物及其在生物医药中的应用 |
| GB201609600D0 (en) | 2016-06-01 | 2016-07-13 | Nucuna Biomed Ltd | Cancer treatments |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2018005444A2 (en) | 2016-06-28 | 2018-01-04 | Boston Biomedical, Inc. | Methods for treating cancer |
| CN106380456B (zh) * | 2016-08-29 | 2019-03-26 | 中南大学 | 一种合成苯并呋喃萘醌衍生物的方法 |
| WO2018098352A2 (en) | 2016-11-22 | 2018-05-31 | Jun Oishi | Targeting kras induced immune checkpoint expression |
| US20190375723A1 (en) | 2016-11-22 | 2019-12-12 | Boston Biomedical, Inc. | New Naphtho[2,3-B]Furan Derivatives |
| US11299469B2 (en) | 2016-11-29 | 2022-04-12 | Sumitomo Dainippon Pharma Oncology, Inc. | Naphthofuran derivatives, preparation, and methods of use thereof |
| EP3548086A1 (en) * | 2016-11-30 | 2019-10-09 | Tyme, Inc. | Tyrosine derivatives and compositions comprising them |
| US20190358212A1 (en) * | 2017-01-22 | 2019-11-28 | Jiangsu Hengrui Medicine Co., Ltd. | Uses of egfr/her2 inhibitor combined with pyrimidine-type anti-metabolic drug |
| WO2018183908A1 (en) * | 2017-03-31 | 2018-10-04 | Dana-Farber Cancer Institute, Inc. | Compositions and methods for treating ovarian tumors |
| US10646464B2 (en) | 2017-05-17 | 2020-05-12 | Boston Biomedical, Inc. | Methods for treating cancer |
| EP3635410A4 (en) * | 2017-06-04 | 2021-03-10 | Rappaport Family Institute for Research in the Medical Sciences | PROCEDURE FOR PREDICTING PERSONALIZED RESPONSE TO CANCER TREATMENT USING IMMUNE CHECKPOINT INHIBITORS AND KITS |
| JP7387177B2 (ja) * | 2017-07-20 | 2023-11-28 | ボード オブ スーパーバイザーズ オブ ルイジアナ ステイト ユニバーシティ アンド アグリカルチュラル アンド メカニカル カレッジ | パルス磁場勾配を使用する悪性癌細胞の標的化浸透圧溶解 |
| CA3074981A1 (en) | 2017-09-22 | 2019-03-28 | Sumitomo Dainippon Pharma Co., Ltd. | Chemically activated water-soluble prodrug |
| IL274698B2 (en) * | 2017-11-16 | 2025-04-01 | Tyrnovo Ltd | Combinations of IRS/STAT3 activity modulators and PD–1/PD–L1 antibodies for cancer treatment |
| EP3501511A1 (en) * | 2017-12-22 | 2019-06-26 | Fundación Centro Nacional De Investigaciones Oncológicas Carlos III | Means for preventing and treating brain metastasis |
| WO2019131940A1 (ja) * | 2017-12-28 | 2019-07-04 | 株式会社カネカ | 多能性幹細胞凝集抑制剤 |
| CN107973788B (zh) * | 2018-01-09 | 2021-07-09 | 沈阳药科大学 | Bbi608衍生物及其制备与用途 |
| BR112020017481A8 (pt) | 2018-03-20 | 2022-12-06 | Sumitomo Dainippon Pharma Co Ltd | Derivados de di-hidrocromeno |
| DK3773537T3 (en) * | 2018-04-19 | 2022-04-25 | Tvardi Therapeutics Inc | Stat3-hæmmere |
| WO2019232214A1 (en) | 2018-05-31 | 2019-12-05 | Boston Biomedical, Inc. | Methods of using napabucasin |
| CN112703001A (zh) * | 2018-09-18 | 2021-04-23 | 株式会社益力多本社 | 使用喹啉羧酰胺衍生物的癌症联用疗法 |
| CN120168498A (zh) * | 2018-10-12 | 2025-06-20 | 北京强新生物科技有限公司 | 治疗化疗难治性癌症的新联合用药方案 |
| CN109223758A (zh) * | 2018-10-31 | 2019-01-18 | 南京先进生物材料与过程装备研究院有限公司 | 一种紫杉醇和芴类stat3抑制剂联合用药物组合物 |
| CN109966297A (zh) * | 2018-10-31 | 2019-07-05 | 南京先进生物材料与过程装备研究院有限公司 | 一种紫杉醇和咔唑类stat抑制剂马来酸盐晶型i联合用药物组合物 |
| CN109846888A (zh) * | 2018-10-31 | 2019-06-07 | 南京先进生物材料与过程装备研究院有限公司 | 一种紫杉醇和吲哚类stat3抑制剂联合用药物组合物 |
| CN109288846A (zh) * | 2018-10-31 | 2019-02-01 | 南京先进生物材料与过程装备研究院有限公司 | 一种紫杉醇和咔唑类stat3抑制剂晶型a联合用药物组合物 |
| CN109288845A (zh) * | 2018-10-31 | 2019-02-01 | 南京先进生物材料与过程装备研究院有限公司 | 一种咔唑类stat抑制剂马来酸盐晶型ii联合用药物组合物及其制备方法 |
| CN109288847A (zh) * | 2018-10-31 | 2019-02-01 | 南京先进生物材料与过程装备研究院有限公司 | 一种紫杉醇和咔唑类stat抑制剂甲磺酸盐晶型p联合用药物组合物 |
| CN109172563A (zh) * | 2018-10-31 | 2019-01-11 | 南京先进生物材料与过程装备研究院有限公司 | 一种噻吨酮类紫杉醇和stat3抑制剂联合用药物组合物 |
| CN109200052A (zh) * | 2018-10-31 | 2019-01-15 | 南京先进生物材料与过程装备研究院有限公司 | 一种紫杉醇和芴酮类stat3抑制剂联合用药物组合物 |
| CN109200044A (zh) * | 2018-10-31 | 2019-01-15 | 南京先进生物材料与过程装备研究院有限公司 | 一种紫杉醇和二苯并[b,d]噻吩类STAT抑制剂酒石酸盐联合用药物组合物 |
| CN109331004A (zh) * | 2018-10-31 | 2019-02-15 | 南京先进生物材料与过程装备研究院有限公司 | 一种紫杉醇和二苯并[b,d]噻吩类STAT抑制剂甲磺酸盐A晶型联合用药物组合物 |
| CN109364252B (zh) * | 2018-11-21 | 2021-09-28 | 南京大学 | 抑制ifn-i至arg1诱导通路在制备抗肿瘤药物组合物中的应用 |
| CN111374981B (zh) * | 2019-04-09 | 2023-09-26 | 健艾仕生物医药有限公司 | 匹莫齐特和甲氨蝶呤的药物组合及其应用 |
| US11564913B2 (en) | 2019-05-03 | 2023-01-31 | Children's Hospital Medical Center | Compositions and methods for treating cancer |
| CN110218198B (zh) * | 2019-05-22 | 2022-06-28 | 广州中医药大学(广州中医药研究院) | 一种萘醌并三氮唑核心骨架衍生物化合物及其制备方法和应用 |
| JPWO2020251015A1 (enExample) * | 2019-06-14 | 2020-12-17 | ||
| JP7287929B2 (ja) * | 2019-09-25 | 2023-06-06 | 住友ファーマ株式会社 | ジヒドロクロメン誘導体を含有する医薬 |
| WO2021089791A1 (en) * | 2019-11-08 | 2021-05-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
| WO2021101902A1 (en) * | 2019-11-20 | 2021-05-27 | Yale University | Compounds, compositions, and methods for treating ischemia-reperfusion injury and/or lung injury |
| CN115297850A (zh) * | 2019-12-05 | 2022-11-04 | 得克萨斯州大学系统董事会 | 用于肝纤维化和其他与纤维化相关的疾病的基于外排体的治疗 |
| WO2021138391A1 (en) | 2019-12-30 | 2021-07-08 | Tyra Biosciences, Inc. | Indazole compounds |
| WO2021185234A1 (zh) * | 2020-03-16 | 2021-09-23 | 正大天晴药业集团股份有限公司 | 作为c-Met激酶抑制剂的化合物的联用药物组合物及其用途 |
| WO2021230956A1 (en) * | 2020-05-11 | 2021-11-18 | Purdue Research Foundation | Scaled-up synthesis of lomustine under continuous flow conditions |
| CN114286684B (zh) * | 2020-07-27 | 2024-01-05 | 华中科技大学 | 与stat3相关的疾病的预防和/或治疗 |
| WO2022216930A1 (en) * | 2021-04-08 | 2022-10-13 | Virginia Commonwealth University | Novel mda-9 antagonist with anti-metastatic potential |
| CN114591306B (zh) * | 2022-03-03 | 2024-03-01 | 陕西中医药大学 | 一种1,2,4-三唑环的1,4萘醌类stat3抑制剂及其应用 |
Family Cites Families (84)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2472133A (en) * | 1947-03-20 | 1949-06-07 | Du Pont | Thiophanthraquinone derivatives |
| SU1049490A1 (ru) | 1982-05-18 | 1983-10-23 | Ордена Трудового Красного Знамени Институт Химии Ан Мсср | (3 @ ,9 @ ,9 @ )-6,6,9 @ -Триметилтранспергидронафто(2,1- @ )фуран,в качестве душистого компонента парфюмерной композиции |
| JPS616149A (ja) | 1984-06-20 | 1986-01-11 | Mitsubishi Electric Corp | 無機絶縁体の製法 |
| JPS63196576A (ja) * | 1987-02-10 | 1988-08-15 | Tetsuo Ikegawa | フラルナフトキノン誘導体と制癌剤及びその製造方法 |
| EP0309926A3 (de) | 1987-09-29 | 1990-12-05 | Siemens Aktiengesellschaft | Verfahren zur Herstellung vollparametrisierbarer Schaltungen in integrierter Schaltkreistechnik |
| JPH01121284A (ja) | 1987-11-06 | 1989-05-12 | Eisai Co Ltd | トコフェロール ｎ，ｎ−ジアルキルアミノアルキルカルボン酸エステルの胆汁酸塩 |
| EP0402192A1 (fr) | 1989-05-31 | 1990-12-12 | BODET, Jean Augustin | Article en carton ou matière analogue et procédé de fabrication |
| JPH04139177A (ja) | 1989-12-28 | 1992-05-13 | Dainippon Ink & Chem Inc | フラルベンゾキノン誘導体及びその製造方法並びに制癌剤 |
| JP2942015B2 (ja) * | 1990-07-10 | 1999-08-30 | キヤノン株式会社 | 電子写真感光体およびそれを用いた電子写真装置 |
| DE69131874T2 (de) * | 1990-07-10 | 2000-06-15 | Canon K.K., Tokio/Tokyo | Elektrophotographisches empfindliches Element |
| TW252136B (enExample) | 1992-10-08 | 1995-07-21 | Ciba Geigy | |
| JP3598168B2 (ja) | 1996-03-18 | 2004-12-08 | 独立行政法人 科学技術振興機構 | 抗ウイルス剤 |
| JPH1121284A (ja) | 1997-06-30 | 1999-01-26 | Kotobuki:Kk | フラノナフトキノン誘導体及びこれを含有する医薬 |
| JPH1165141A (ja) * | 1997-08-11 | 1999-03-05 | Canon Inc | 電子写真感光体、該電子写真感光体を有するプロセスカ−トリッジ及び電子写真装置 |
| US6174913B1 (en) | 1998-06-05 | 2001-01-16 | The University Of North Carolina At Chapel Hill | Naphtho- and dihydrobenzo-thiophene derivatives as cytotoxic antitumor agents |
| JP2003525862A (ja) | 1999-01-27 | 2003-09-02 | ザ ユニヴァーシティー オブ サウス フロリダ | ヒト癌の治療のためのｓｔａｔ３シグナル伝達の阻害 |
| DK2266537T3 (en) | 1999-04-01 | 2014-12-15 | Talon Therapeutics Inc | Compositions for treating cancer |
| US6482943B1 (en) | 1999-04-30 | 2002-11-19 | Slil Biomedical Corporation | Quinones as disease therapies |
| CA2386793C (en) * | 1999-08-02 | 2006-03-28 | F. Hoffmann-La Roche Ag | New selective retinoid agonists |
| JP2001097860A (ja) | 1999-09-29 | 2001-04-10 | Japan Science & Technology Corp | 抗薬剤耐性菌剤と抗クラミジア剤 |
| UA75055C2 (uk) * | 1999-11-30 | 2006-03-15 | Пфайзер Продактс Інк. | Похідні бензоімідазолу, що використовуються як антипроліферативний засіб, фармацевтична композиція на їх основі |
| KR20010100194A (ko) | 2000-03-13 | 2001-11-14 | 박호군 | 여러 가지 물질의 가용화용 조성물과 제형 및 그들의제조방법 |
| AU2002307217A1 (en) | 2001-03-28 | 2002-10-15 | University Of South Florida | Materials and methods for treatment of cancer and identification of anti-cancer compounds |
| GB0117696D0 (en) | 2001-07-20 | 2001-09-12 | Bradford Particle Design Plc | Particle information |
| AU2002357012A1 (en) | 2001-11-27 | 2003-06-10 | Transform Pharmaceuticals, Inc. | Oral pharmaceutical formulations comprising paclitaxel, derivatives and methods of administration thereof |
| KR20040096497A (ko) | 2001-11-29 | 2004-11-16 | 테라코스, 인크. | 체외 광분리반출법 및/또는 세포소멸성 세포를 사용한특정 대상체의 전처리 방법 |
| EP1487436A4 (en) * | 2002-03-08 | 2009-06-03 | Signal Pharm Inc | POLYTHERAPY FOR TREATING, PREVENTING OR MANAGING PROLIFERATIVE DISORDERS AND CANCERS |
| DK1344533T3 (da) * | 2002-03-15 | 2007-01-08 | Natimmune As | Farmaceutiske præparater, der omfatter mannosebindende lectin |
| WO2004024145A1 (en) | 2002-09-10 | 2004-03-25 | Dabur Research Foundation | Anti-cancer activity of carvedilol and its isomers |
| WO2004026253A2 (en) * | 2002-09-17 | 2004-04-01 | Arqule, Inc. | Novel lapacho compounds and methods of use thereof |
| TWI323662B (en) | 2002-11-15 | 2010-04-21 | Telik Inc | Combination cancer therapy with a gst-activated anticancer compound and another anticancer therapy |
| AR042052A1 (es) | 2002-11-15 | 2005-06-08 | Vertex Pharma | Diaminotriazoles utiles como inhibidores de proteinquinasas |
| IS6633A (is) | 2002-11-22 | 2004-05-23 | Omega Farma Ehf. | Samsetningar af fínasteríð töflum |
| KR20060031809A (ko) * | 2003-06-09 | 2006-04-13 | 더 리젠츠 오브 더 유니버시티 오브 미시간 | 암 치료 및 진단용 조성물 및 방법 |
| WO2005023824A2 (en) | 2003-08-13 | 2005-03-17 | University Of South Florida | Methods for inhibiting tumor cell proliferation |
| US20050049207A1 (en) * | 2003-09-03 | 2005-03-03 | Kaufmann Doug A. | Method of treating and preventing cancer |
| WO2005033048A2 (en) | 2003-09-29 | 2005-04-14 | The Johns Hopkins University | Wnt pathway antagonists |
| EP1706133B1 (en) | 2003-12-02 | 2010-10-06 | Cleveland Clinic Foundation | Methods of protecting against radiation using flagellin |
| ES2385831T3 (es) * | 2003-12-11 | 2012-08-01 | Board Of Regents, The University Of Texas System | Compuestos para el tratamiento de enfermedades celulares proliferativas |
| DE10359828A1 (de) | 2003-12-12 | 2005-07-28 | Zoser B. Dr.Rer.Nat. Salama | CHP-Gemcitabin- Kombinationsmittel und ihre Verwendung als Antitumorwirkstoffe, insbesondere Antimetastasierungswirkstoffe |
| EP1748772A2 (en) * | 2004-04-09 | 2007-02-07 | University Of South Florida | Combination therapies for cancer and proliferative angiopathies |
| JP2004224802A (ja) * | 2004-04-21 | 2004-08-12 | Japan Science & Technology Agency | 抗菌剤 |
| CN101010316A (zh) * | 2004-07-02 | 2007-08-01 | 艾科斯有限公司 | 用于抑制chk1的化合物 |
| CN101023086A (zh) * | 2004-08-18 | 2007-08-22 | 阿斯利康(瑞典)有限公司 | 选择性稠合的杂环及其应用 |
| AU2005304952B2 (en) * | 2004-11-08 | 2013-04-04 | Baxter Healthcare S.A. | Nanoparticulate compositions of tubulin inhibitors |
| BRPI0517887A (pt) * | 2004-11-24 | 2008-10-21 | Novartis Ag | combinações de inibidores de jaks |
| WO2006071812A2 (en) * | 2004-12-23 | 2006-07-06 | H. Lee Moffitt Cancer Center And Research Institute | Platinum iv complex inhibitor |
| CN101511179A (zh) * | 2005-02-25 | 2009-08-19 | 密执安州立大学董事会 | Stat3的小分子抑制剂及其用途 |
| JP2006248978A (ja) * | 2005-03-10 | 2006-09-21 | Mebiopharm Co Ltd | 新規なリポソーム製剤 |
| JP2006290871A (ja) * | 2005-03-16 | 2006-10-26 | Taheebo Japan Kk | 抗癌性を示す化合物およびその中間体ならびにそれらの製造方法 |
| US20060252073A1 (en) * | 2005-04-18 | 2006-11-09 | Regents Of The University Of Michigan | Compositions and methods for the treatment of cancer |
| JPWO2006126505A1 (ja) | 2005-05-26 | 2008-12-25 | 国立大学法人 東京大学 | Ｓｔａｔ機能阻害剤およびその応用 |
| WO2007013946A2 (en) * | 2005-07-20 | 2007-02-01 | University Of South Florida | Method of predicting responsiveness to chemotherapy and selecting treatments |
| AU2006300877A1 (en) | 2005-10-13 | 2007-04-19 | Orchid Research Laboratories Limited | Heterocyclic compounds as pSTAT3/IL-6 inhibitors |
| UA96139C2 (uk) * | 2005-11-08 | 2011-10-10 | Дженентек, Інк. | Антитіло до нейропіліну-1 (nrp1) |
| AR057579A1 (es) * | 2005-11-23 | 2007-12-05 | Merck & Co Inc | Compuestos espirociclicos como inhibidores de histona de acetilasa (hdac) |
| JP2007145680A (ja) | 2005-11-30 | 2007-06-14 | Idemitsu Kosan Co Ltd | 水素発生材料および水素発生方法 |
| EP1971578A1 (en) * | 2005-12-24 | 2008-09-24 | Biotica Technology Limited | 21-deoxymacbecin analogues useful as antitumor agents |
| CA2635209A1 (en) * | 2006-01-12 | 2007-08-02 | Merck & Co., Inc. | Fluorinated arylamide derivatives |
| WO2007092620A2 (en) * | 2006-02-09 | 2007-08-16 | Macusight, Inc. | Stable formulations, and methods of their preparation and use |
| US20070243192A1 (en) * | 2006-02-21 | 2007-10-18 | Regents Of The University Of Michigan | Growth hormone receptor antagonist cancer treatment |
| CA2643562A1 (en) * | 2006-02-24 | 2007-08-30 | Anh Chau | 2-(phenyl or heterocyclic)-1h-phenanthro[9,10-d]imidazoles |
| PL2514742T3 (pl) * | 2006-03-31 | 2015-07-31 | Univ Texas | Leki przeciwnowotworowe będące pochodnymi kwasu kawowego dostępnymi biologicznie po podaniu doustnym |
| US20070238770A1 (en) | 2006-04-05 | 2007-10-11 | Bristol-Myers Squibb Company | Process for preparing novel crystalline forms of peliglitazar, novel stable forms produced therein and formulations |
| US8828451B2 (en) * | 2006-10-04 | 2014-09-09 | University Of South Florida | Akt sensitization of cancer cells |
| WO2008077062A2 (en) * | 2006-12-19 | 2008-06-26 | Board Of Regents, The University Of Texas System | Suppression of stat3 reactivation after src kinase inhibition to treat cancer |
| JP4077863B1 (ja) * | 2007-05-31 | 2008-04-23 | タヒボジャパン株式会社 | 抗癌活性を有する光学活性２−（１−ヒドロキシエチル）−５−ヒドロキシナフト［２，３−ｂ］フラン−４，９−ジオンの製法 |
| CA2736563C (en) | 2007-09-10 | 2016-01-26 | Boston Biomedical, Inc. | A novel group of stat3 pathway inhibitors and cancer stem cell pathway inhibitors |
| WO2009060282A2 (en) | 2007-11-06 | 2009-05-14 | Orchid Research Laboratories Limited | Stilbene derivatives as pstat3/il-6 inhibitors |
| EP3108750B1 (en) | 2010-03-19 | 2018-07-04 | 1Globe Biomedical Co., Ltd. | Novel compounds and compositions for targeting cancer stem cells |
| MX394137B (es) | 2010-03-19 | 2025-03-24 | Boston Biomedical Inc | Compuestos y composiciones novedosas para atacar las células madre del cáncer. |
| AU2015218436B9 (en) | 2010-03-19 | 2017-03-09 | Boston Biomedical, Inc. | Novel Methods For Targeting Cancer Stem Cells |
| LT2547205T (lt) | 2010-03-19 | 2024-06-10 | 1Globe Biomedical Co., Ltd. | Nauji tikslinio poveikio vėžio kamieninėms ląstelėms būdai |
| CN103402993A (zh) | 2011-03-04 | 2013-11-20 | 舟山海中洲新生药业有限公司 | 用于疾病治疗的4，9-二羟基-萘并[2,3-b] 呋喃新型酯 |
| US8977803B2 (en) | 2011-11-21 | 2015-03-10 | Western Digital Technologies, Inc. | Disk drive data caching using a multi-tiered memory |
| WO2013166618A1 (en) | 2012-05-08 | 2013-11-14 | Zhoushan Haizhongzhou Xinsheng Pharmaceuticals Co., Ltd. | PRODRUGS OF 4,9-DIHYDROXY-NAPHTHO[2,3-b]FURANS FOR CIRCUMVENTING CANCER MULTIDRUG RESISTANCE |
| MX2015014181A (es) | 2013-04-09 | 2016-05-24 | Boston Biomedical Inc | 2-acetilnafto [2,3-b]furano -4,9-diona para uso en el tratamiento del cáncer. |
| MX2017013358A (es) | 2015-04-17 | 2018-08-01 | Boston Biomedical Inc | Métodos para tratar el cáncer. |
| BR112017022281A2 (pt) | 2015-04-17 | 2018-07-10 | Boston Biomedical Inc | métodos para tratar câncer |
| TW201713328A (zh) | 2015-04-17 | 2017-04-16 | 波士頓生醫公司 | 治療癌症之方法 |
| BR112017022958A2 (pt) | 2015-04-27 | 2018-07-17 | Boston Biomedical Inc | métodos para tratamento de câncer com inibidor da via da stat3 e inibidor de quinase |
| WO2016196935A1 (en) | 2015-06-03 | 2016-12-08 | Boston Biomedical, Inc. | Compositions comprising a cancer stemness inhibitor and an immunotherapeutic agent for use in treating cancer |
| WO2017132049A1 (en) | 2016-01-20 | 2017-08-03 | Boston Biomedical, Inc. | Methods for treating cancer |
| US10646464B2 (en) | 2017-05-17 | 2020-05-12 | Boston Biomedical, Inc. | Methods for treating cancer |
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