CA2673683C - Compounds and method for treatment of cancer - Google Patents
Compounds and method for treatment of cancer Download PDFInfo
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- CA2673683C CA2673683C CA2673683A CA2673683A CA2673683C CA 2673683 C CA2673683 C CA 2673683C CA 2673683 A CA2673683 A CA 2673683A CA 2673683 A CA2673683 A CA 2673683A CA 2673683 C CA2673683 C CA 2673683C
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US88450407P | 2007-01-11 | 2007-01-11 | |
| US60/884,504 | 2007-01-11 | ||
| US60/884,489 | 2007-01-11 | ||
| PCT/CA2008/000045 WO2008083491A1 (en) | 2007-01-11 | 2008-01-11 | Compounds and method for treatment of cancer |
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| CA2673683A1 CA2673683A1 (en) | 2008-07-17 |
| CA2673683C true CA2673683C (en) | 2014-07-29 |
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| EP (1) | EP2121681B1 (https=) |
| JP (1) | JP5571387B2 (https=) |
| CA (1) | CA2673683C (https=) |
| IL (1) | IL199689A0 (https=) |
| WO (1) | WO2008083491A1 (https=) |
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| EP2121681B1 (en) | 2007-01-11 | 2015-04-15 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| US20080176958A1 (en) | 2007-01-24 | 2008-07-24 | Insert Therapeutics, Inc. | Cyclodextrin-based polymers for therapeutics delivery |
| CA2710039C (en) | 2007-12-26 | 2018-07-03 | Critical Outcome Technologies, Inc. | Semicarbazones, thiosemicarbazones and related compounds and methods for treatment of cancer |
| EP2318406B1 (en) | 2008-07-17 | 2016-01-27 | Critical Outcome Technologies, Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| CN102781237A (zh) * | 2009-11-23 | 2012-11-14 | 天蓝制药公司 | 用于传递治疗剂的基于环糊精的聚合物 |
| EP2552915B1 (en) | 2010-04-01 | 2017-07-19 | Critical Outcome Technologies Inc. | Compounds for the treatment of hiv |
| US20140094432A1 (en) | 2012-10-02 | 2014-04-03 | Cerulean Pharma Inc. | Methods and systems for polymer precipitation and generation of particles |
| US20140271812A1 (en) * | 2013-03-14 | 2014-09-18 | Panacea Pharmaceuticals | Treatment for chemotherapy-induced cognitive impairment |
| US10392397B2 (en) | 2015-08-06 | 2019-08-27 | Nantbio, Inc. | Heterocyclic thiosemicarbazone derivatives and their therapeutical applications |
| MA45865A (fr) | 2016-08-07 | 2021-04-14 | Wistar Inst | Procédés de détection et de traitement d'une tumeur exprimant pt346 pdk1 |
Family Cites Families (157)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239539A (en) | 1960-12-02 | 1966-03-08 | Exxon Research Engineering Co | Gem dimethylol alicyclic esters |
| GB1026401A (en) | 1961-02-23 | 1966-04-20 | Wellcome Found | Isatin thiosemicarbazones,their preparation and pharmaceutical formulations containing them |
| US3250791A (en) | 1961-12-29 | 1966-05-10 | Du Pont | Tetracyanoethylene oxide and process for preparing same |
| GB1231783A (en) | 1967-05-16 | 1971-05-12 | May & Baker Ltd | Benzene derivatives |
| DE1767924A1 (de) | 1968-07-02 | 1971-10-07 | Bayer Ag | 1-Phenyl-4,4-dialkyl-thiosemicarbazide |
| JPS5695161A (en) * | 1979-12-28 | 1981-08-01 | Otsuka Pharmaceut Factory Inc | 2-admantanon derivative |
| US4463077A (en) | 1982-05-26 | 1984-07-31 | Toray Industries, Inc. | Electrophotographic photosensitive material comprises pyrazoline and hydrazone derivatives |
| US4537844A (en) | 1982-10-08 | 1985-08-27 | Ricoh Co. Ltd. | Electrophotographic element containing disazo compound |
| DE3237649A1 (de) | 1982-10-11 | 1984-04-12 | Hoechst Ag, 6230 Frankfurt | 3-aryl-7-chlor-10-hydroxy-3,4-dihydro-acridin-1,9-(2h, 10h)-dion-1-oxime und -1-hydrazonderivate, deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| DE3372094D1 (en) | 1982-10-11 | 1987-07-23 | Hoechst Ag | 3-aryl-7-chloro-3,4-dihydro-acridine-1,9-(2h,10h)-dione-1-oximes and 1-hydrazones, their salts, process for their preparation and pharmaceutical preparations containing them, and their application |
| HU189765B (en) | 1983-10-25 | 1986-07-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing n-substituted 1-(bis (hydroxy-metiol)-methyl)-isoquinoline-derivatives |
| US4619878A (en) | 1984-06-26 | 1986-10-28 | Ricoh Co., Ltd. | Tetrazonium salt compound, disazo compound, method for preparing the same, and photosensitive material containing said disazo compound for use in electrophotography |
| EP0183398B1 (en) | 1984-11-30 | 1989-04-12 | FISONS plc | Angiotensin converting enzyme inhibitors and their production and use as pharmaceuticals |
| US4833153A (en) | 1985-11-08 | 1989-05-23 | Glaxo Group Limited | Indole derivatives |
| IL77496A (en) | 1986-01-01 | 1989-02-28 | Univ Ramot | Anti-viral preparations comprising isatine 3-thiosemicarbazones |
| JPH01502022A (ja) | 1986-04-07 | 1989-07-13 | ジ・アップジョン・カンパニー | 駆虫薬第４級アルキルアシルヒドラゾン、使用方法および組成物 |
| US5023334A (en) | 1986-10-03 | 1991-06-11 | The Upjohn Company | Anthelmintic pyridinyl acylhydrazones |
| DE3851598T2 (de) | 1987-09-09 | 1995-05-24 | Zeneca Ltd | Schimmelbekämpfungsmittel. |
| US5155110A (en) | 1987-10-27 | 1992-10-13 | Warner-Lambert Company | Fenamic acid hydroxamate derivatives having cyclooxygenase and 5-lipoxygenase inhibition |
| US4958010A (en) | 1988-02-16 | 1990-09-18 | Bristol-Myers Company | Epipodophyllotoxin glucoside lactam derivatives |
| NZ229555A (en) | 1988-06-16 | 1992-03-26 | Rohm & Haas | Pharmaceutical compositions for combating helminths in animals |
| JP2521137B2 (ja) | 1988-11-08 | 1996-07-31 | 富士写真フイルム株式会社 | 電子写真感光体 |
| US5196291A (en) | 1989-05-24 | 1993-03-23 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| EP0420005B1 (en) | 1989-09-18 | 1996-07-10 | Fuji Photo Film Co., Ltd. | High contrast silver halide photographic material |
| FI905255A7 (fi) | 1989-10-25 | 1991-04-26 | Egyt Gyogyszervegyeszeti Gyar | Menetelmä uusien terapeuttisesti käyttökelpoisten triatsolojohdannaisten valmistamiseksi |
| US4985434A (en) | 1989-10-31 | 1991-01-15 | Biocryst, Inc. | 7-substituted derivatives of 2-amino-3H,5H-pyrrolo(3,2-d)pyrimidin-4-ones and pharamceutical uses and compositions containing the same |
| US5008265A (en) | 1989-10-31 | 1991-04-16 | Biocryst, Inc. | 2-amino-7-(alicyclomethyl)-3H,5H,-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same |
| US4985433A (en) | 1989-10-31 | 1991-01-15 | Biocryst, Inc. | 2-amino-7-(pyridinylmethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same |
| US5008270A (en) | 1989-10-31 | 1991-04-16 | Biocryst, Inc. | 2-amino-7-(heterocyclomethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same |
| JP3093767B2 (ja) | 1989-11-27 | 2000-10-03 | 松下電工株式会社 | 洗浄装置 |
| US5189039A (en) | 1989-11-29 | 1993-02-23 | Biocryst, Inc. | 7-disubstituted-methyl-4-oxo-3H,5H-pyrrolo[3,2d]pyrimidine and pharmaceutical uses and compositions containing the same |
| US5230983A (en) | 1990-04-13 | 1993-07-27 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| LU87766A1 (fr) | 1990-07-20 | 1992-03-11 | Oreal | Utilisation de derives de pyrimidine 3-oxyde pour freiner la chute des cheveux et compositions topiques mises en oeuvre |
| NZ239846A (en) | 1990-09-27 | 1994-11-25 | Merck & Co Inc | Sulphonamide derivatives and pharmaceutical compositions thereof |
| US5747469A (en) | 1991-03-06 | 1998-05-05 | Board Of Regents, The University Of Texas System | Methods and compositions comprising DNA damaging agents and p53 |
| JPH05333467A (ja) | 1991-05-02 | 1993-12-17 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
| SG64322A1 (en) | 1991-05-10 | 1999-04-27 | Rhone Poulenc Rorer Int | Bis mono and bicyclic aryl and heteroaryl compounds which inhibit egf and/or pdgf receptor tyrosine kinase |
| USRE37650E1 (en) | 1991-05-10 | 2002-04-09 | Aventis Pharmacetical Products, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| US5714493A (en) | 1991-05-10 | 1998-02-03 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| US5480883A (en) | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| US5344836A (en) | 1991-11-11 | 1994-09-06 | Ono Pharmaceutical Co., Ltd. | Fused benzeneoxyacetic acid derivatives |
| DE4138820A1 (de) | 1991-11-26 | 1993-05-27 | Basf Ag | Chinolin-3-carbonsaeureamide, deren herstellung und verwendung |
| JP2787630B2 (ja) | 1992-02-06 | 1998-08-20 | 富士写真フイルム株式会社 | ハロゲン化銀感光材料 |
| DE4207400A1 (de) | 1992-03-09 | 1993-09-16 | Bayer Ag | Hydrazone |
| US5521184A (en) | 1992-04-03 | 1996-05-28 | Ciba-Geigy Corporation | Pyrimidine derivatives and processes for the preparation thereof |
| US5358946A (en) | 1992-05-29 | 1994-10-25 | The Du Pont Merck Pharmaceutical Company | Heterocycle-substituted amides, carbamates and ureas as agents for the treatment of atherosclerosis |
| JP2994182B2 (ja) | 1992-07-23 | 1999-12-27 | 石原産業株式会社 | アミド系化合物又はその塩、それらの製造方法及びそれらを含有する有害動物防除剤 |
| EP0600832A1 (de) | 1992-11-27 | 1994-06-08 | Ciba-Geigy Ag | Diaminobenzoe- und Diaminophthalsäurederivate und ihre Verfahren als Proteinkinase-Inhibitoren |
| TW251302B (https=) | 1992-12-28 | 1995-07-11 | Kao Corp | |
| US5618829A (en) | 1993-01-28 | 1997-04-08 | Mitsubishi Chemical Corporation | Tyrosine kinase inhibitors and benzoylacrylamide derivatives |
| US5750088A (en) | 1993-03-30 | 1998-05-12 | The Dupont Merck Pharmaceutical Company | Stable hydrazones linked to a peptide moiety as reagents for the preparation of radiopharmaceuticals |
| JP3350739B2 (ja) | 1993-06-10 | 2002-11-25 | コニカ株式会社 | 黒白ハロゲン化銀写真感光材料の現像処理方法 |
| US5543520A (en) | 1993-10-01 | 1996-08-06 | Ciba-Geigy Corporation | Pyrimidine derivatives |
| WO1995009847A1 (en) | 1993-10-01 | 1995-04-13 | Ciba-Geigy Ag | Pyrimidineamine derivatives and processes for the preparation thereof |
| US5656643A (en) | 1993-11-08 | 1997-08-12 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| RU2137762C1 (ru) | 1994-02-23 | 1999-09-20 | Пфайзер Инк. | 4-гетероциклил-замещенные производные хиназолина, фармацевтическая композиция |
| JP3875263B2 (ja) | 1994-04-06 | 2007-01-31 | 塩野義製薬株式会社 | α−置換フェニル酢酸誘導体、その製造法ならびにそれを含有する農業用殺菌剤 |
| EP0704215A3 (en) | 1994-06-02 | 1998-04-01 | Takeda Chemical Industries, Ltd. | Inhibitor of vascular permeability enhancer |
| TW280906B (https=) | 1994-12-01 | 1996-07-11 | Ibm | |
| DE19501481A1 (de) | 1995-01-19 | 1996-07-25 | Bayer Ag | 2,8-Disubstituierte Chinazolinone |
| JPH08220666A (ja) | 1995-02-15 | 1996-08-30 | Konica Corp | 黒白ハロゲン化銀写真感光材料及びその処理方法 |
| JPH11507329A (ja) | 1995-04-27 | 1999-06-29 | ゼネカ リミテッド | キナゾリン誘導体 |
| US5763470A (en) | 1995-06-07 | 1998-06-09 | Sugen Inc. | Benzopyran compounds and methods for their use |
| US6265427B1 (en) | 1995-06-07 | 2001-07-24 | The Proctor & Gamble Company | Pharmaceutical composition for the method of treating leukemia |
| CA2222545A1 (en) | 1995-06-07 | 1996-12-19 | Sugen, Inc. | Quinazolines and pharmaceutical compositions |
| US5633786A (en) | 1995-08-21 | 1997-05-27 | Motorola | Shield assembly and method of shielding suitable for use in a communication device |
| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| DE19545878A1 (de) | 1995-12-08 | 1997-06-12 | Basf Ag | Pyridylcarbamate, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| DE19619518A1 (de) | 1996-05-15 | 1997-11-20 | Haeussler & Sauter Kg | Verfahren zur Anbringung eines Fadens an einem Aufgußbeutel |
| US6306574B1 (en) | 1996-05-17 | 2001-10-23 | Fuji Photo Film Co., Ltd. | Photothermographic material |
| US20040171032A1 (en) | 1996-06-06 | 2004-09-02 | Baker Brenda F. | Non-phosphorous-linked oligomeric compounds and their use in gene modulation |
| AR007857A1 (es) | 1996-07-13 | 1999-11-24 | Glaxo Group Ltd | Compuestos heterociclicos fusionados como inhibidores de proteina tirosina quinasa, sus metodos de preparacion, intermediarios uso en medicina ycomposiciones farmaceuticas que los contienen. |
| HRP970371A2 (en) | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
| EA199900021A1 (ru) | 1996-07-13 | 1999-08-26 | Глаксо, Груп Лимитед | Бициклические гетероароматические соединения в качестве ингибиторов протеинтирозинкиназы |
| WO1998007726A1 (en) | 1996-08-23 | 1998-02-26 | Novartis Ag | Substituted pyrrolopyrimidines and processes for their preparation |
| US6251911B1 (en) | 1996-10-02 | 2001-06-26 | Novartis Ag | Pyrimidine derivatives and processes for the preparation thereof |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| ZA986729B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitors of tyrosine kinases |
| ZA986732B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitiors of tyrosine kinases |
| GB9716557D0 (en) | 1997-08-06 | 1997-10-08 | Glaxo Group Ltd | Benzylidene-1,3-dihydro-indol-2-one derivatives having anti-cancer activity |
| EP0902028A1 (en) | 1997-09-11 | 1999-03-17 | E.I. Du Pont De Nemours And Company | Tetrazoline herbicides |
| US6184377B1 (en) | 1997-12-15 | 2001-02-06 | Sepracor Inc. | Compositions containing N-amino- and N-hydroxy-quinazolinones and methods for preparing libraries thereof |
| EP1054004B1 (en) | 1997-12-15 | 2008-07-16 | Astellas Pharma Inc. | Novel pyrimidine-5-carboxamide derivatives |
| JP4642226B2 (ja) | 1998-02-06 | 2011-03-02 | デ モントフォート ユニヴァーシティ | ヒドロキシル化により活性化されたプロドラッグ |
| JP2002513008A (ja) | 1998-04-29 | 2002-05-08 | ジョージタウン ユニヴァーシティー | Ｈｌａ−作動薬及び拮抗薬としてのｈｌａ結合性化合物の同定及び使用方法 |
| US20010051628A1 (en) | 1998-05-04 | 2001-12-13 | H.-J. Su Huang | Methods to modulate the resistance of cells to apoptosis mediated by mutant epidermal growth factor receptors |
| US6289352B1 (en) | 1998-05-29 | 2001-09-11 | Crystal Decisions, Inc. | Apparatus and method for compound on-line analytical processing in databases |
| JPH11345811A (ja) | 1998-06-01 | 1999-12-14 | Seiko Instruments Inc | 半導体装置の製造方法 |
| US6596770B2 (en) | 2000-05-05 | 2003-07-22 | Medinox, Inc. | Therapeutic methods employing disulfide derivatives of dithiocarbamates and compositions useful therefor |
| US20030181495A1 (en) | 1998-06-23 | 2003-09-25 | Medinox, Inc. | Therapeutic methods employing disulfide derivatives of dithiocarbamates and compositions useful therefor |
| JP2002523455A (ja) | 1998-08-31 | 2002-07-30 | スージェン・インコーポレーテッド | 蛋白質キナーゼ活性の調節剤としての幾何学的に制限された２−インドリノン誘導体 |
| JP2000143636A (ja) | 1998-09-02 | 2000-05-26 | Sumitomo Pharmaceut Co Ltd | アミノ誘導体 |
| US20010041964A1 (en) | 1998-09-14 | 2001-11-15 | George M. Grass | Pharmacokinetic-based drug design tool and method |
| US6420560B1 (en) | 1999-06-07 | 2002-07-16 | Theravance, Inc. | H1—histamine receptor antagonists |
| WO2000076511A1 (en) | 1999-06-11 | 2000-12-21 | Merck & Co., Inc. | Cyclopentyl modulators of chemokine receptor activity |
| US7169778B2 (en) | 1999-09-15 | 2007-01-30 | Warner-Lambert Company | Pteridinones as kinase inhibitors |
| US7264932B2 (en) | 1999-09-24 | 2007-09-04 | Applera Corporation | Nuclease inhibitor cocktail |
| GB9924862D0 (en) | 1999-10-20 | 1999-12-22 | Celltech Therapeutics Ltd | Chemical compounds |
| JP2001172217A (ja) | 1999-12-21 | 2001-06-26 | Shionogi & Co Ltd | 殺ダニ活性および殺菌活性を有するエチレン誘導体 |
| GB2357971A (en) | 1999-12-23 | 2001-07-11 | Novartis Ag | Protection of plants against microorganism attack |
| ITMI992711A1 (it) | 1999-12-27 | 2001-06-27 | Novartis Ag | Composti organici |
| HN2001000008A (es) | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| KR20010111298A (ko) | 2000-02-05 | 2001-12-17 | 버텍스 파마슈티칼스 인코포레이티드 | Ｅｒｋ의 억제제로서 유용한 피라졸 조성물 |
| US6313138B1 (en) | 2000-02-25 | 2001-11-06 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| US6420382B2 (en) | 2000-02-25 | 2002-07-16 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| JP2004500388A (ja) | 2000-03-01 | 2004-01-08 | スローン−ケッタリング インスティトュート フォア キャンサー リサーチ | エポチロン、その中間体およびその類似体の合成 |
| GB0007657D0 (en) | 2000-03-29 | 2000-05-17 | Celltech Therapeutics Ltd | Chemical compounds |
| GB2372562A (en) | 2000-04-26 | 2002-08-28 | Ribotargets Ltd | In silico screening |
| DE60141871D1 (de) | 2000-05-05 | 2010-06-02 | Wallac Oy | Oligonukleotidmarkierungsstoffe und ihre Verwendung |
| DE10023492A1 (de) | 2000-05-09 | 2001-11-22 | Schering Ag | Aza- und Polyazanthranylamide und deren Verwendung als Arzneimittel |
| US6489094B2 (en) | 2000-05-31 | 2002-12-03 | Pfizer Inc. | Method and device for drug-drug interaction testing sample preparation |
| US7211192B2 (en) | 2000-06-02 | 2007-05-01 | The Regents Of The University Of California | Hybrid organic-inorganic adsorbents |
| US7022484B2 (en) | 2000-06-08 | 2006-04-04 | Board Of Regents, The University Of Texas System | Methods for treating neuropathological states and neurogenic inflammatory states and methods for identifying compounds useful therein |
| US20020028826A1 (en) | 2000-06-15 | 2002-03-07 | Robl Jeffrey A. | HMG-CoA reductase inhibitors and method |
| US20020013334A1 (en) | 2000-06-15 | 2002-01-31 | Robl Jeffrey A. | HMG-CoA reductase inhibitors and method |
| US6620821B2 (en) | 2000-06-15 | 2003-09-16 | Bristol-Myers Squibb Company | HMG-CoA reductase inhibitors and method |
| BR0112355A (pt) | 2000-06-26 | 2005-04-19 | Univ Michigan | Uso de inibidores da proteìna egf-r tirosina cinase para a prevenção do fotoenvelhecimento da pele humana |
| EP1311277A4 (en) | 2000-07-18 | 2004-08-25 | Joslin Diabetes Center Inc | METHODS OF FIBROSIS MODULATION |
| US7067046B2 (en) | 2000-08-04 | 2006-06-27 | Essen Instruments, Inc. | System for rapid chemical activation in high-throughput electrophysiological measurements |
| US6647342B2 (en) | 2000-08-07 | 2003-11-11 | Novodynamics, Inc. | Knowledge-based process for the development of materials |
| GB0022438D0 (en) | 2000-09-13 | 2000-11-01 | Novartis Ag | Organic Compounds |
| ATE303998T1 (de) | 2000-10-17 | 2005-09-15 | Merck & Co Inc | Oral aktive salze mit tyrosinkinaseaktivität |
| WO2002094019A1 (en) | 2001-05-22 | 2002-11-28 | Eisai Co., Ltd | Highly purified antiendotoxin compound |
| JP2002361158A (ja) | 2001-06-07 | 2002-12-17 | Aica Kogyo Co Ltd | 塗布装置 |
| US6352168B1 (en) | 2001-06-21 | 2002-03-05 | Jung-Chuang Lin | Rotation cup |
| WO2003004489A1 (en) | 2001-07-05 | 2003-01-16 | Gpc Biotech Inc. | Compositions and methods for inhibiting prenyltransferases |
| JP2004534097A (ja) | 2001-07-09 | 2004-11-11 | フアルマシア・イタリア・エツセ・ピー・アー | ＴＣＦ−４とβ−カテニンの相互作用阻害剤 |
| WO2003070241A1 (en) | 2002-02-15 | 2003-08-28 | Rigel Pharmaceuticals, Inc. | Inhibitors of tubulin polymerization |
| WO2003084940A1 (en) | 2002-04-08 | 2003-10-16 | Alangudi Sankaranarayanan | Thiazolidine-4-carbonitriles and analogues and their use as dipeptidyl-peptidas inhibitors |
| US7202367B2 (en) | 2002-05-31 | 2007-04-10 | Rhodia Chimie | Process for arylating or vinylating or alkynating a nucleophilic compound |
| WO2004037787A1 (de) | 2002-10-18 | 2004-05-06 | Basf Aktiengesellschaft | 1-phenylpyrrolidin-2-on-3-carboxamide |
| WO2004069801A1 (en) | 2003-02-05 | 2004-08-19 | Unisearch Limited | Metal ion chelators and therapeutic use thereof |
| EP1594894A2 (en) | 2003-02-18 | 2005-11-16 | Whitehead Institute For Biomedical Research | Mtor kinase-associated proteins |
| EP1614676A4 (en) | 2003-03-27 | 2009-03-25 | Kirin Pharma Kk | CONNECTION TO INHIBITING IN VIVO PHOSPHORUS TRANSPORT AND MEDICAMENT CONTAINING THEREOF |
| US20040193538A1 (en) | 2003-03-31 | 2004-09-30 | Raines Walter L. | Receipt processing system and method |
| US7427683B2 (en) | 2003-04-25 | 2008-09-23 | Ortho-Mcneil Pharmaceutical, Inc. | c-fms kinase inhibitors |
| US20050010017A1 (en) | 2003-07-11 | 2005-01-13 | Blakely Dale Milton | Addition of UV inhibitors to pet process for maximum yield |
| US20050249697A1 (en) | 2003-09-24 | 2005-11-10 | Uhrich Kathryn E | Compositions and methods for the inhibition of bone growth and resorption |
| US7410961B2 (en) * | 2004-01-20 | 2008-08-12 | Merck & Co., Inc. | 2,6-disubstituted piperiddines as modulators |
| JP4902361B2 (ja) | 2004-01-30 | 2012-03-21 | メディヴィル・アクチエボラーグ | Ｈｃｖｎｓ−３セリンプロテアーゼインヒビター |
| ZA200607582B (en) | 2004-03-05 | 2009-02-25 | Univ California | Anti-parasitic compounds and methods of their use |
| EP1799679B1 (de) * | 2004-10-13 | 2008-01-23 | Merck Patent GmbH | Als kinaseinhibitoren geeignete derivate des n,n'-diphenylharnstoffs |
| FR2879194B1 (fr) | 2004-12-14 | 2007-01-19 | Galderma Res & Dev | Nouveaux composes bi-aromatiques modulateurs des recepteurs de type ppar, leur procede de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques |
| AR054416A1 (es) | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| JP2006181940A (ja) | 2004-12-28 | 2006-07-13 | Mitsubishi Paper Mills Ltd | インクジェット用記録材料 |
| CN1891701A (zh) | 2005-07-07 | 2007-01-10 | 桑迪亚医药技术（上海）有限责任公司 | 杂芳环缩氨基硫脲类化合物及其衍生物和它们在制备抗肿瘤药物中的应用 |
| CN100497309C (zh) | 2005-08-04 | 2009-06-10 | 卡南吉医药科技（上海）有限公司 | 杂芳环缩氨基硫脲类抗肿瘤药物的合成方法 |
| EP1928847A4 (en) | 2005-08-29 | 2011-08-10 | Gerard M Housey | THERAMUTEINE MODULATORS |
| EP1996193A2 (en) | 2006-03-13 | 2008-12-03 | OSI Pharmaceuticals, Inc. | Combined treatment with an egfr kinase inhibitor and an agent that sensitizes tumor cells to the effects of egfr kinase inhibitors |
| JP2008008853A (ja) | 2006-06-30 | 2008-01-17 | Univ Of Electro-Communications | 地点間距離変動検出装置及び方法 |
| JP2008088107A (ja) | 2006-10-02 | 2008-04-17 | Fujiyakuhin Co Ltd | 新規ピリダジン誘導体 |
| EP2121681B1 (en) | 2007-01-11 | 2015-04-15 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| CA2710039C (en) | 2007-12-26 | 2018-07-03 | Critical Outcome Technologies, Inc. | Semicarbazones, thiosemicarbazones and related compounds and methods for treatment of cancer |
| EP2318406B1 (en) | 2008-07-17 | 2016-01-27 | Critical Outcome Technologies, Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
-
2008
- 2008-01-11 EP EP08700510.4A patent/EP2121681B1/en not_active Not-in-force
- 2008-01-11 CA CA2673683A patent/CA2673683C/en not_active Expired - Fee Related
- 2008-01-11 US US12/013,079 patent/US8034815B2/en active Active - Reinstated
- 2008-01-11 JP JP2009545043A patent/JP5571387B2/ja not_active Expired - Fee Related
- 2008-01-11 WO PCT/CA2008/000045 patent/WO2008083491A1/en not_active Ceased
-
2009
- 2009-07-05 IL IL199689A patent/IL199689A0/en unknown
-
2011
- 2011-07-25 US US13/190,230 patent/US8367675B2/en not_active Expired - Fee Related
- 2011-12-02 US US13/310,506 patent/US8420643B2/en not_active Expired - Fee Related
-
2013
- 2013-02-19 US US13/770,749 patent/US8822475B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8822475B2 (en) | 2014-09-02 |
| US8034815B2 (en) | 2011-10-11 |
| US20130165449A1 (en) | 2013-06-27 |
| JP5571387B2 (ja) | 2014-08-13 |
| US20120077820A1 (en) | 2012-03-29 |
| US8367675B2 (en) | 2013-02-05 |
| US20080171744A1 (en) | 2008-07-17 |
| JP2010515693A (ja) | 2010-05-13 |
| US8420643B2 (en) | 2013-04-16 |
| EP2121681B1 (en) | 2015-04-15 |
| WO2008083491A1 (en) | 2008-07-17 |
| CA2673683A1 (en) | 2008-07-17 |
| US20110281887A1 (en) | 2011-11-17 |
| EP2121681A1 (en) | 2009-11-25 |
| EP2121681A4 (en) | 2011-06-15 |
| IL199689A0 (en) | 2010-04-15 |
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