PL219449B1 - Pochodne 5-fenylotiazolu, zawierające je kompozycje farmaceutyczne oraz lecznicze zastosowania tych związków - Google Patents
Pochodne 5-fenylotiazolu, zawierające je kompozycje farmaceutyczne oraz lecznicze zastosowania tych związkówInfo
- Publication number
- PL219449B1 PL219449B1 PL403456A PL40345603A PL219449B1 PL 219449 B1 PL219449 B1 PL 219449B1 PL 403456 A PL403456 A PL 403456A PL 40345603 A PL40345603 A PL 40345603A PL 219449 B1 PL219449 B1 PL 219449B1
- Authority
- PL
- Poland
- Prior art keywords
- phenyl
- methanesulfonyl
- methyl
- thiazol
- acid
- Prior art date
Links
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- PAWMWHKFNGHSCO-UHFFFAOYSA-N 1-[5-(4-chloro-3-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]-3-propylurea Chemical compound S1C(NC(=O)NCCC)=NC(C)=C1C1=CC=C(Cl)C(S(C)(=O)=O)=C1 PAWMWHKFNGHSCO-UHFFFAOYSA-N 0.000 claims description 3
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| CN101965408B (zh) | 2008-02-04 | 2013-08-28 | 塞尔卓姆有限责任公司 | 针对多重靶的pi3k相互作用分子的选择性概况分析 |
| UA104147C2 (uk) | 2008-09-10 | 2014-01-10 | Новартис Аг | Похідна піролідиндикарбонової кислоти та її застосування у лікуванні проліферативних захворювань |
| CN101684106B (zh) * | 2008-09-22 | 2013-06-12 | 北京摩力克科技有限公司 | 噻唑鎓盐类化合物及其治疗蛋白老化相关疾病的用途 |
| PL2404908T3 (pl) * | 2009-02-27 | 2014-12-31 | Teijin Ltd | Sposób wytwarzania podstawionej fenylem pochodnej heterocyklicznej przez sprzężenie z użyciem katalizatora metalu przejściowego |
| TW201103943A (en) * | 2009-04-27 | 2011-02-01 | Shionogi & Co | Urea derivative having pi3k inhibitory activity |
| US8293753B2 (en) | 2009-07-02 | 2012-10-23 | Novartis Ag | Substituted 2-carboxamide cycloamino ureas |
| EA201200087A1 (ru) | 2009-07-02 | 2012-07-30 | Новартис Аг | 2-карбоксамиды циклоаминомочевин, которые являются ингибиторами pi3k |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011048936A1 (ja) | 2009-10-19 | 2011-04-28 | 大正製薬株式会社 | アミノチアゾール誘導体 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| ES2670659T3 (es) | 2010-02-03 | 2018-05-31 | Signal Pharmaceuticals, Llc | Identificación de mutación en LKB1 como un biomarcador predictivo para la sensibilidad a inhibidores de la quinasa TOR |
| GB2485886A (en) * | 2010-11-24 | 2012-05-30 | Lithera Inc | Injectable formulations comprising a lipophilic glucocorticosteroid for regional adiposity reduction |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| WO2013019927A1 (en) | 2011-08-03 | 2013-02-07 | Signal Pharmaceuticals, Llc | Identification of gene expression profile as a predictive biomarker for lkb1 status |
| US9926309B2 (en) | 2011-10-05 | 2018-03-27 | The Board Of Trustees Of The Leland Stanford Junior University | Pi-kinase inhibitors with anti-infective activity |
| EP2763532B1 (en) * | 2011-10-05 | 2018-09-19 | The Board of Trustees of the Leland Stanford Junior University | Pi-kinase inhibitors with broad spectrum anti-infective activity |
| JP6348848B2 (ja) | 2012-02-13 | 2018-06-27 | ガミダ セル リミテッド | 間葉系幹細胞の増殖 |
| US9567569B2 (en) | 2012-07-23 | 2017-02-14 | Gamida Cell Ltd. | Methods of culturing and expanding mesenchymal stem cells |
| US9175266B2 (en) | 2012-07-23 | 2015-11-03 | Gamida Cell Ltd. | Enhancement of natural killer (NK) cell proliferation and activity |
| AU2013203714B2 (en) | 2012-10-18 | 2015-12-03 | Signal Pharmaceuticals, Llc | Inhibition of phosphorylation of PRAS40, GSK3-beta or P70S6K1 as a marker for TOR kinase inhibitory activity |
| UA115805C2 (uk) | 2013-04-17 | 2017-12-26 | Сігнал Фармасьютікалз, Елелсі | Комбінована терапія, яка включає сполуку дигідропіразинопіразину й антагоніст рецептора андрогену, для лікування раку простати |
| US9358232B2 (en) | 2013-04-17 | 2016-06-07 | Signal Pharmaceuticals, Llc | Methods for treating cancer using TOR kinase inhibitor combination therapy |
| NZ631082A (en) | 2013-04-17 | 2017-06-30 | Signal Pharm Llc | Methods for treating cancer using tor kinase inhibitor combination therapy |
| WO2014172436A1 (en) | 2013-04-17 | 2014-10-23 | Signal Pharmaceuticals, Llc | Combination therapy comprising a tor kinase inhibitor and a 5-substituted quinazolinone compound for treating cancer |
| PH12021552945B1 (en) | 2013-04-17 | 2024-02-28 | Signal Pharm Llc | Treatment of cancer with dihydropyrazino-pyrazines |
| EA037683B1 (ru) | 2013-04-17 | 2021-04-29 | СИГНАЛ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Фармацевтические составы, способы, твердые формы и способы применения, относящиеся к 1-этил-7-(2-метил-6-(1h-1,2,4-триазол-3-ил)пиридин-3-ил)-3,4-дигидропиразино[2,3-b] пиразин-2(1h)-ону |
| KR102221029B1 (ko) | 2013-04-17 | 2021-02-26 | 시그날 파마소티칼 엘엘씨 | 디하이드로피라지노-피라진을 사용한 암의 치료 |
| CN105407892B (zh) | 2013-05-29 | 2019-05-07 | 西格诺药品有限公司 | 一种化合物的药物组合物、其固体形式及它们的使用方法 |
| CN104418858B (zh) | 2013-08-30 | 2018-12-11 | 浙江医药股份有限公司新昌制药厂 | 2,6-二含氮取代的嘌呤衍生物及其制备方法和其药物组合物与应用 |
| DE102013226711A1 (de) * | 2013-12-19 | 2015-06-25 | Beiersdorf Ag | Verwendung von Alkylamidothiazolen in kosmetischen oder dermatologischen Zubereitungen zur Prophylaxe vor und Behandlung von sensibler Haut |
| WO2015160880A1 (en) | 2014-04-16 | 2015-10-22 | Signal Pharmaceuticals, Llc | SOLID FORMS COMPRISING 1-ETHYL-7-(2-METHYL-6-(1H-1,2,4-TRIAZOL-3-YL) PYRIDIN-3-YL)-3,4-DIHYDROPYRAZINO(2,3-b)PYRAZIN-2(1H)-ONE, AND A COFORMER, COMPOSITIONS AND METHODS OF USE THEREOF |
| NZ714742A (en) | 2014-04-16 | 2017-04-28 | Signal Pharm Llc | Solid forms of 1-ethyl-7-(2-methyl-6-(1h-1,2,4-triazol-3-yl)pyridin-3-yl)-3,4-dihydropyrazino[2,3-b]pyrazin-2(1h)-one, compositions thereof and methods of their use |
| WO2015162584A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Crystalline forms of the sulfate salt of n-[5-(3-imidazol-1-yl-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide |
| WO2016065583A1 (en) | 2014-10-30 | 2016-05-06 | Merck Sharp & Dohme Corp. | Oxazole orexin receptor antagonists |
| BR112018003622B8 (pt) * | 2015-09-04 | 2022-08-23 | Dow Agrosciences Llc | Moléculas apresentando utilidade pesticida, e composição pesticida |
| CN108290832B (zh) * | 2015-09-04 | 2020-11-27 | 美国陶氏益农公司 | 有杀虫效用的分子,以及与其相关的中间体、组合物和方法 |
| US9758491B2 (en) * | 2015-09-10 | 2017-09-12 | Dow Agrosciences Llc | Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto |
| EP3395801B1 (en) * | 2015-12-16 | 2021-03-31 | Nippon Soda Co., Ltd. | Arylazole compound and pest control agent |
| CA3012861C (en) | 2016-02-01 | 2023-01-24 | The Governing Council Of The University Of Toronto | 53bp1 inhibitors |
| ES3010661T3 (en) * | 2016-02-26 | 2025-04-04 | Univ Leland Stanford Junior | Pi-kinase inhibitors with anti-infective activity |
| IL271491B2 (en) | 2017-06-22 | 2023-09-01 | Celgene Corp | Treatment of carcinoma of the liver characterized by hepatitis b virus infection |
| EP3713963A1 (en) | 2017-11-23 | 2020-09-30 | INSERM (Institut National de la Santé et de la Recherche Médicale) | A new marker for predicting the sensitivity to pi3k inhibitors |
| EP3941909A4 (en) | 2019-03-21 | 2023-01-25 | The Board Of Trustees Of The Leland Stanford Junior University | Pi4-kinase inhibitors and methods of using the same |
| AU2020338971B2 (en) * | 2019-08-28 | 2023-11-23 | Novartis Ag | Substituted 1,3-phenyl heteroaryl derivatives and their use in the treatment of disease |
| CN115028596B (zh) * | 2021-03-03 | 2024-06-07 | 帕潘纳(北京)科技有限公司 | 制备苯唑草酮中间体的方法 |
| EP4638477A1 (en) | 2022-12-19 | 2025-10-29 | Kamau Therapeutics, Inc. | Improved peptide inhibitors of p53 binding protein 53bp1 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB951885A (en) | 1961-05-13 | 1964-03-11 | Sankyo Co | A new process for the preparation of thiazole compounds |
| OA01933A (fr) | 1965-04-06 | 1970-02-04 | Pechiney Saint Gobain | Dérivés du thiazole. |
| US3749775A (en) | 1969-07-07 | 1973-07-31 | Stauffer Chemical Co | Insecticidal 2-aminothiazole phosphates and phosphonates |
| FR2429210A1 (fr) * | 1978-06-19 | 1980-01-18 | Fabre Sa Pierre | Derives de phenyl-4 thiazolyl-2 oxamates utiles dans le traitement de l'asthme |
| US4511574A (en) * | 1981-01-08 | 1985-04-16 | Mitsui Toatsu Kagaku Kabushiki Kaisha | N-(4-Phenyl-2-thiazolyl)carbamate derivatives |
| JPS57136579A (en) | 1981-01-21 | 1982-08-23 | Mitsui Toatsu Chem Inc | Thiazolylurea derivative, its preparation, and pharmaceutical composition containing the same |
| DE3413755A1 (de) | 1984-04-12 | 1985-10-24 | Basf Ag, 6700 Ludwigshafen | Thiazolylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| JPH0725754B2 (ja) | 1986-01-30 | 1995-03-22 | 富山化学工業株式会社 | 新規なチアゾール化合物またはその塩 |
| EP0321115B1 (en) * | 1987-12-14 | 1991-08-14 | Sawai Pharmaceutical Co., Ltd. | Carboxamide derivatives having tetrazole and thiazole rings and their use |
| US4891375A (en) | 1988-01-13 | 1990-01-02 | Pfizer Inc. | Arylpiperazinyl-alkylene-phenyl-heterocyclic compounds |
| CA2396738C (en) | 1990-11-30 | 2006-08-29 | Masatoshi Chihiro | Thiazole derivatives as active superoxide radical inhibitors |
| DE4401911A1 (de) | 1994-01-24 | 1995-08-03 | Basf Ag | Verwendung von Aryl- oder Heteroarylazoanilinen in der nichtlinearen Optik |
| AU3201095A (en) | 1994-07-27 | 1996-02-22 | G.D. Searle & Co. | Substituted thiazoles for the treatment of inflammation |
| CA2206315A1 (en) * | 1994-11-29 | 1996-06-06 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/or salt thereof |
| GB9625843D0 (en) * | 1996-12-12 | 1997-01-29 | Merck & Co Inc | Phenyl spiroethercycloalkyl tachykinn receptor antagonists |
| JP4437270B2 (ja) | 1997-12-22 | 2010-03-24 | バイエル コーポレイション | 置換複素環式尿素を用いたrafキナーゼの阻害 |
| US6100282A (en) * | 1998-01-02 | 2000-08-08 | Hoffman-La Roche Inc. | Thiazole derivatives |
| EP0928790B1 (en) * | 1998-01-02 | 2003-03-05 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
| US6043254A (en) * | 1998-04-03 | 2000-03-28 | Boehringer Ingelheim Pharma Kg | Indolinones having kinase-inhibiting activity |
| GB9823873D0 (en) * | 1998-10-30 | 1998-12-30 | Pharmacia & Upjohn Spa | 2-ureido-thiazole derivatives,process for their preparation,and their use as antitumour agents |
| CN1263743C (zh) | 2000-01-24 | 2006-07-12 | 基纳西亚股份有限公司 | 用于治疗的吗啉代基取代的化合物 |
| KR100785363B1 (ko) | 2000-04-25 | 2007-12-18 | 이코스 코포레이션 | 인간 포스파티딜-이노시톨 3-키나제 델타의 억제제 |
| PL365170A1 (en) | 2000-07-26 | 2004-12-27 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl] carboxamide inhibitors of cyclin dependent kinases |
| UA82827C2 (en) | 2000-12-18 | 2008-05-26 | Inhibitors against the production and release of inflammatory cytokines | |
| AR039059A1 (es) | 2001-08-06 | 2005-02-09 | Sanofi Aventis | Compuesto derivado de acilaminotiazol, su utilizacion, procedimientos para prepararlo, composicion farmaceutica que lo comprende, y compuestos intermediarios |
| AU2002327534A1 (en) * | 2001-08-17 | 2003-03-03 | Merck And Co., Inc. | Tyrosine kinase inhibitors |
| US6812653B2 (en) * | 2002-07-26 | 2004-11-02 | Richard S. Bellivean | Method and apparatus for controlling images with image projection lighting devices |
| GB0525671D0 (en) * | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
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