KR20100017184A - 골수증식성 질환 및 다른 증식성 질환의 치료에 유용한 키나제 억제제 - Google Patents
골수증식성 질환 및 다른 증식성 질환의 치료에 유용한 키나제 억제제 Download PDFInfo
- Publication number
- KR20100017184A KR20100017184A KR1020097024209A KR20097024209A KR20100017184A KR 20100017184 A KR20100017184 A KR 20100017184A KR 1020097024209 A KR1020097024209 A KR 1020097024209A KR 20097024209 A KR20097024209 A KR 20097024209A KR 20100017184 A KR20100017184 A KR 20100017184A
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- South Korea
- Prior art keywords
- alkyl
- pyrazol
- phenyl
- methyl
- pyridin
- Prior art date
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Classifications
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D401/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P27/00—Drugs for disorders of the senses
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- A—HUMAN NECESSITIES
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110189167A1 (en) * | 2007-04-20 | 2011-08-04 | Flynn Daniel L | Methods and Compositions for the Treatment of Myeloproliferative Diseases and other Proliferative Diseases |
| BRPI0807717A2 (pt) | 2007-04-20 | 2014-05-20 | Deciphera Pharmaceuticals Llc | Inibidores de quinase úteis para o tratamento de doenças mieloproliferativas e outras doenças proliferativas. |
| KR20110099687A (ko) * | 2008-10-29 | 2011-09-08 | 데시페라 파마슈티칼스, 엘엘씨. | 항-암과 항-증식성 활성을 나타내는 시클로프로판 아미드와 유사체 |
| AU2010289353B2 (en) * | 2009-09-03 | 2016-12-08 | Allergan, Inc. | Compounds as tyrosine kinase modulators |
| WO2011062955A2 (en) * | 2009-11-18 | 2011-05-26 | University Of Massachusetts | Compounds for modulating tlr2 |
| PL2509961T3 (pl) | 2009-12-11 | 2016-09-30 | Pochodne imidazolidynodionu | |
| US8912184B1 (en) | 2010-03-01 | 2014-12-16 | Alzheimer's Institute Of America, Inc. | Therapeutic and diagnostic methods |
| EP2594566A4 (en) * | 2010-07-16 | 2014-10-01 | Kyowa Hakko Kirin Co Ltd | AROMATIC HETEROCYCLIC NITROGEN CYCLE DERIVATIVE |
| CN103080109A (zh) * | 2010-09-01 | 2013-05-01 | 苏州爱斯鹏药物研发有限责任公司 | 氘代杂环化合物激酶抑制剂 |
| CN102408408A (zh) * | 2010-09-20 | 2012-04-11 | 北大方正集团有限公司 | 具有抗肿瘤作用的芳基脲衍生物 |
| CN102432592A (zh) * | 2010-09-29 | 2012-05-02 | 北大方正集团有限公司 | 具有抗肿瘤作用的芳基脲衍生物及其制备方法 |
| US9346790B2 (en) | 2010-12-06 | 2016-05-24 | Autifony Therapeutics Limited | Hydantoin derivatives useful as Kv3 inhibitors |
| US8563558B2 (en) * | 2010-12-06 | 2013-10-22 | Confluence Life Sciences, Inc. | Substituted pyridine urea compounds |
| CN102558144A (zh) * | 2010-12-22 | 2012-07-11 | 北大方正集团有限公司 | 一种芳基脲衍生物 |
| CN102532113B (zh) * | 2010-12-22 | 2014-09-10 | 北大方正集团有限公司 | 芳基脲衍生物 |
| KR20120100027A (ko) * | 2011-03-02 | 2012-09-12 | 한국생명공학연구원 | 엔도사이토시스 모티프 및 단백질 도입 도메인을 포함하는 암 예방 또는 치료용 약학적 조성물 |
| UA114711C2 (uk) | 2011-05-13 | 2017-07-25 | Еррей Біофарма Інк. | Сполуки піролідинілсечовини й піролідинілтіосечовини як інгібітори кінази trka |
| JP6008953B2 (ja) | 2011-06-07 | 2016-10-19 | アウトイフオンイ トヘラペウトイクス リミテッド | Ｋｖ３阻害剤としてのヒダントイン誘導体 |
| WO2013036232A2 (en) * | 2011-09-08 | 2013-03-14 | Deciphera Pharmaceuticals, Llc | Methods and compositions for the treatment of myeloproliferative diseases and other proliferative diseases |
| WO2013161919A1 (ja) | 2012-04-26 | 2013-10-31 | 小野薬品工業株式会社 | Ｔｒｋ阻害化合物 |
| BR112014028718A2 (pt) | 2012-05-22 | 2017-06-27 | Autifony Therapeutics Ltd | derivados de hidantoína como inibidores de kv3 |
| US9422252B2 (en) | 2012-05-22 | 2016-08-23 | Autifony Therapeutics Limited | Triazoles as Kv3 inhibitors |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| EP2875014B1 (en) * | 2012-07-17 | 2017-11-29 | Washington University | Anti-mucus drugs and uses therefor |
| WO2014078328A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-bicyclic aryl,n'-pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9790178B2 (en) | 2012-11-13 | 2017-10-17 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| US9981959B2 (en) | 2012-11-13 | 2018-05-29 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078378A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9809578B2 (en) | 2012-11-13 | 2017-11-07 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trkA kinase inhibitors |
| EP2922844B1 (en) | 2012-11-13 | 2018-01-10 | Array Biopharma, Inc. | N-pyrrolidinyl, n'-pyrazolyl- urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9822118B2 (en) | 2012-11-13 | 2017-11-21 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078331A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(arylalkyl)-n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| US9790210B2 (en) | 2012-11-13 | 2017-10-17 | Array Biopharma Inc. | N-(monocyclic aryl),N'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| HRP20161613T1 (hr) | 2012-11-13 | 2017-01-13 | Array Biopharma, Inc. | Tvari bicikličke ureje, tioureje, gvanidina i cijanogvanidina korisne za liječenje boli |
| EP2960234B1 (en) | 2013-02-19 | 2018-12-19 | ONO Pharmaceutical Co., Ltd. | Trk-inhibiting compound |
| CA2903081A1 (en) | 2013-03-14 | 2014-09-25 | Quanticel Pharmaceuticals, Inc. | Histone demethylase inhibitors |
| WO2014172639A1 (en) * | 2013-04-19 | 2014-10-23 | Ruga Corporation | Raf kinase inhibitors |
| ITMI20132201A1 (it) * | 2013-12-23 | 2015-06-24 | Isagro Spa | Processo per la sintesi regioselettiva di pirazoli |
| CN104974132B (zh) * | 2014-04-08 | 2017-05-17 | 北大方正集团有限公司 | 多取代的吡啶化合物、制备方法、用途及药物组合物 |
| RU2719489C2 (ru) | 2014-05-15 | 2020-04-17 | Эррэй Биофарма Инк. | 1-((3S,4R)-4-(3-ФТОРФЕНИЛ)-1-(2-МЕТОКСИЭТИЛ)ПИРРОЛИДИН-3-ИЛ)-3-(4-МЕТИЛ-3-(2-МЕТИЛПИРИМИДИН-5-ИЛ)-1-ФЕНИЛ-1Н-ПИРАЗОЛ-5-ИЛ)МОЧЕВИНА В КАЧЕСТВЕ ИНГИБИТОРА TrkA КИНАЗЫ |
| PE20181539A1 (es) * | 2016-02-02 | 2018-09-26 | Basf Se | Proceso de hidrogenacion catalitico para preparar pirazoles |
| CN105646448B (zh) * | 2016-02-03 | 2019-03-01 | 沈阳药科大学 | 吡啶类化合物及其用途 |
| CN108341813B (zh) * | 2017-01-24 | 2020-11-17 | 四川大学 | 取代的1-(异恶唑-3-基)-3-(3-氟-4-苯基)脲衍生物及其制备方法和用途 |
| AU2018392816B2 (en) | 2017-12-22 | 2023-04-20 | HiberCell Inc. | Chromenopyridine derivatives as phosphatidylinositol phosphate kinase inhibitors |
| BR112020015581A2 (pt) | 2018-01-31 | 2021-02-02 | Deciphera Pharmaceuticals, Llc | terapia de combinação para o tratamento de tumores estromais gastrointestinais |
| EP3746060A1 (en) | 2018-01-31 | 2020-12-09 | Deciphera Pharmaceuticals, LLC | Combination therapy for the treatment of mastocytosis |
| CA3121202A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| BR112021012812A2 (pt) | 2018-12-28 | 2021-12-07 | Deciphera Pharmaceuticals Llc | Csf1r inhibitors para uso e tratamento de câncer |
| EP3934763A4 (en) * | 2019-03-06 | 2023-03-15 | University Of Maryland, Baltimore | SCAFFOLDS OF TETRAMERIC PROTEINS USED AS NANO-CARRIERS OF THERAPEUTIC PEPTIDES FOR THE TREATMENT OF CANCER AND OTHER DISEASES |
| CN118878519A (zh) | 2019-05-10 | 2024-11-01 | 德西费拉制药有限责任公司 | 苯基氨基嘧啶酰胺自噬抑制剂及其使用方法 |
| IL287795B2 (en) | 2019-05-10 | 2025-05-01 | Deciphera Pharmaceuticals Llc | Heteroarylaminopyrimidine amides as autophagy inhibitors and methods of using them |
| WO2020257180A1 (en) | 2019-06-17 | 2020-12-24 | Deciphera Pharmaceuticals, Llc | Aminopyrimidine amide autophagy inhibitors and methods of use thereof |
| WO2021013712A1 (en) | 2019-07-19 | 2021-01-28 | Anagenesis Biotechnologies S.A.S. | Polyaromatic urea derivatives and their use in the treatment of muscle diseases |
| WO2021030405A1 (en) | 2019-08-12 | 2021-02-18 | Deciphera Pharmaceuticals, Llc | Ripretinib for treating gastrointestinal stromal tumors |
| KR20220045189A (ko) | 2019-08-12 | 2022-04-12 | 데시페라 파마슈티칼스, 엘엘씨. | 위장관 기질 종양을 치료하는 방법 |
| CN118948773A (zh) | 2019-12-30 | 2024-11-15 | 德西费拉制药有限责任公司 | 1-(4溴-5-(1乙基-7-(甲氨基)-2侧氧基-1,2-二氢-1,6-萘啶-3基)-2氟苯基)-3-苯基脲的组合物 |
| SMT202300467T1 (it) | 2019-12-30 | 2024-01-10 | Deciphera Pharmaceuticals Llc | Formulazioni di inibitori di chinasi amorfi e loro procedimenti d’uso |
| MX2022014021A (es) * | 2020-05-08 | 2023-02-16 | Georgiamune Llc | Moduladores de akt3. |
| EP4247795A1 (en) | 2020-11-18 | 2023-09-27 | Deciphera Pharmaceuticals, LLC | Gcn2 and perk kinase inhibitors and methods of use thereof |
| CN112830936B (zh) * | 2021-01-08 | 2022-01-28 | 广西师范大学 | 核黄素化合物、其制备方法及应用 |
| EP4029501A1 (en) | 2021-01-19 | 2022-07-20 | Anagenesis Biotechnologies | Combination of polyaromatic urea derivatives and glucocorticoid or hdac inhibitor for the treatment of diseases or conditions associated with muscle cells and/or satellite cells |
| CN115772167B (zh) * | 2021-09-08 | 2025-07-29 | 暨南大学 | 含脲结构的化合物及其应用 |
| MX2024007042A (es) | 2021-12-09 | 2024-09-04 | Deciphera Pharmaceuticals Llc | Inhibidores de raf quinasa y metodos de uso de los mismos. |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
| WO2025122952A1 (en) | 2023-12-08 | 2025-06-12 | Deciphera Pharmaceuticals, Llc | Formulations of vimseltinib |
Family Cites Families (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115350B (de) | 1959-04-17 | 1961-10-19 | Siemens Ag | Selbstschalter, insbesondere Leitungsschutz-schalter, mit einem aus einem Kniegelenk bestehenden Antriebsmechanismus fuer das Schaltorgan |
| GB971307A (en) | 1961-03-02 | 1964-09-30 | Wellcome Found | 5-anilinopyrimidines |
| GB1127875A (en) * | 1967-03-23 | 1968-09-18 | Parke Davis & Co | 4-(5-nitro-2-furyl) thiazolyl hydantoins and hydrouracils |
| US3949002A (en) * | 1970-11-13 | 1976-04-06 | Imperial Chemical Industries Limited | Process for producing sulfone containing thiophenols |
| US3818024A (en) * | 1972-02-16 | 1974-06-18 | Velsicol Chemical Corp | Benzothiazol substituted thiadiazolidines |
| CH565887A5 (enExample) | 1972-08-22 | 1975-08-29 | Ciba Geigy Ag | |
| US3939122A (en) * | 1973-04-11 | 1976-02-17 | Bayer Aktiengesellschaft | Process for the preparation of compounds which contain hydantoin rings |
| FR2337554A1 (fr) | 1976-01-08 | 1977-08-05 | Buzas Andre | Nouveaux derives de la pyrazolidinedione |
| US4093624A (en) * | 1977-01-31 | 1978-06-06 | Icn Pharmaceuticals, Inc. | 1,2,4-Thiadiazolidine-3,5-dione |
| FR2396549A2 (fr) | 1977-07-06 | 1979-02-02 | Buzas Andre | Nouveaux derives de la pyrazolidinedione |
| US4256758A (en) | 1979-06-11 | 1981-03-17 | Merck & Co., Inc. | 4-Substituted-3-hydroxy-3-pyrroline-2,5-dione inhibitors of glycolic acid oxidase |
| US4298743A (en) | 1979-09-11 | 1981-11-03 | Merck & Co., Inc. | 4-(Substituted phenyl thiazolyl)-3-hydroxy-3-pyrroline-2,5-diones |
| US4296237A (en) * | 1979-09-11 | 1981-10-20 | Merck & Co., Inc. | 4-(Pyridyl, piperazinyl and thiazolyl substituted thiazolyl)-3-hydroxy-3-pyrroline-2,5-diones |
| US4432992A (en) * | 1979-11-05 | 1984-02-21 | Merck & Co., Inc. | 4-[5(and 4)-Substituted-2-thienyl]-3-hydroxy-3-pyrroline-2,5-dione inhibitors of glycolic acid oxidase |
| US4366189A (en) * | 1979-12-21 | 1982-12-28 | Ciba-Geigy Corporation | 4-Heterocyclyl-4'-vinylstilbenes |
| JPS5915247A (ja) | 1982-07-16 | 1984-01-26 | Mitsubishi Paper Mills Ltd | 画像形成方法 |
| JPS59177557A (ja) * | 1983-03-28 | 1984-10-08 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| DE3406329A1 (de) | 1984-02-22 | 1985-08-22 | Merck Patent Gmbh, 6100 Darmstadt | Pyridone |
| US4816454A (en) * | 1984-09-21 | 1989-03-28 | Cassella Aktiengesellschaft | 4,5-dihydro-3(2H)-pyridazinones and their pharmacological use |
| US5103014A (en) * | 1987-09-30 | 1992-04-07 | American Home Products Corporation | Certain 3,3'-[[[(2-phenyl-4-thiazolyl)methoxy]phenyl]methylene]dithiobis-propanoic acid derivatives |
| AU606808B2 (en) | 1988-06-29 | 1991-02-14 | Otsuka Pharmaceutical Factory, Inc. | Arylcarboxamide substituted by alkylphosphonates, process for preparing the same and a pharmaceutical composition containing the same |
| GB9012936D0 (en) | 1990-06-11 | 1990-08-01 | Fujisawa Pharmaceutical Co | Thiophene derivatives,processes for preparation thereof and pharmaceutical composition comprising the same |
| US5254715A (en) | 1990-11-07 | 1993-10-19 | Warner-Lambert Company | Aminosulfonyl carbamates |
| EP0525197B1 (en) * | 1991-01-21 | 1997-08-27 | Shionogi Seiyaku Kabushiki Kaisha | 3-benzylidene-1-carbamoyl-2-pyrrolidone analogs |
| US5162360A (en) * | 1991-06-24 | 1992-11-10 | Warner-Lambert Company | 2-heteroatom containing urea and thiourea ACAT inhibitors |
| DE4302702A1 (de) | 1993-02-01 | 1994-08-04 | Bayer Ag | Arylaminosulfonylharnstoffe |
| WO1994021617A1 (en) | 1993-03-19 | 1994-09-29 | Dowelanco | A process for preparing halogenated isothiazoles |
| EP0692483A1 (en) | 1993-03-30 | 1996-01-17 | Yoshitomi Pharmaceutical Industries, Ltd. | Cell adhesion inhibitor and thienotriazolodiazepine compound |
| WO1994024095A1 (en) | 1993-04-16 | 1994-10-27 | Abbott Laboratories | Immunosuppressive agents |
| CA2123728A1 (en) * | 1993-05-21 | 1994-11-22 | Noriyoshi Sueda | Urea derivatives and their use as acat inhibitors |
| DE4337847A1 (de) | 1993-11-05 | 1995-05-11 | Bayer Ag | Substituierte Phenylaminosulfonylharnstoffe |
| EP0733048A1 (en) | 1993-12-07 | 1996-09-25 | Smithkline Beecham Plc | Heterocyclic biphenylylamides useful as 5ht1d antagonists |
| DE4343831A1 (de) | 1993-12-22 | 1995-06-29 | Magyar Tudomanyos Akademia | Substituierte Sulfonylharnstoffe |
| FR2715155B1 (fr) * | 1994-01-19 | 1996-07-26 | Mayoly Spindler | Inhibiteurs de la monoamine oxydase B et leurs procédés de préparation. |
| DE4414840A1 (de) | 1994-04-28 | 1995-11-02 | Bayer Ag | Substituierte Phenylaminosulfonylharnstoffe |
| CN100384825C (zh) | 1994-06-15 | 2008-04-30 | 大塚制药株式会社 | 苯并杂环衍生物 |
| DK0793656T3 (da) | 1994-11-24 | 2003-07-21 | Basilea Pharmaceutica Ag | Hidtil ukendte benzyl-pyrimidiner |
| US5494925A (en) * | 1994-12-02 | 1996-02-27 | Sterling Winthrop Inc. | 2-heterocyclyloxymethyl and 2-heterocyclylthiomethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxides and compositions and method of use thereof |
| US5972951A (en) | 1994-12-22 | 1999-10-26 | Smithkline Beecham Plc | Tetracyclic spiro compounds, process for their preparation and their use as 5HT1D receptor antagonists |
| EP0739884B1 (en) | 1995-04-24 | 2003-08-13 | Semiconductor Energy Laboratory Co., Ltd. | Liquid crystal compound and liquid crystal composition containing the same |
| JPH09221476A (ja) | 1995-12-15 | 1997-08-26 | Otsuka Pharmaceut Co Ltd | 医薬組成物 |
| GB9605945D0 (en) | 1996-03-21 | 1996-05-22 | Smithkline Beecham Plc | Novel compounds |
| PL192628B1 (pl) * | 1996-04-23 | 2006-11-30 | Vertex Pharma | Pochodne mocznika, kompozycje farmaceutyczne i zastosowanie związku i kompozycji |
| JPH107804A (ja) | 1996-06-25 | 1998-01-13 | Japan Synthetic Rubber Co Ltd | 熱硬化性樹脂組成物 |
| GB9623833D0 (en) | 1996-11-16 | 1997-01-08 | Zeneca Ltd | Chemical compound |
| US6020357A (en) * | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
| ATE230742T1 (de) | 1997-03-27 | 2003-01-15 | Great Lakes Chemical Europ | 2-(2'-hydroxphenyl)-benzotriazole und ihre verwendung als lichtschutzmittel für organische polymere |
| DE69826695T2 (de) | 1997-05-23 | 2006-02-02 | Bayer Pharmaceuticals Corp., West Haven | Arylharnstoffderivate zur behandlung von inflammatorischen oder immunomodulatorischen erkrankungen |
| US6235786B1 (en) * | 1997-08-06 | 2001-05-22 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| US6294573B1 (en) * | 1997-08-06 | 2001-09-25 | Abbott Laboratories | Reverse hydroxamate inhibitors of matrix metalloproteinases |
| CN1271279A (zh) | 1997-09-23 | 2000-10-25 | 普尼卡有限公司 | 用于治疗细胞因子介导性疾病的酰胺类衍生物 |
| IT1295933B1 (it) | 1997-10-30 | 1999-05-28 | Great Lakes Chemical Italia | 2-(2'-idrossifenil)benzotriazoli e procedimento per la loro preparazione |
| JP2001521934A (ja) * | 1997-11-03 | 2001-11-13 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症薬としての芳香族ヘテロ環式化合物 |
| CA2315720A1 (en) | 1997-12-22 | 1999-07-01 | Bayer Corporation | Inhibition of p38 kinase activity using substituted heterocyclic ureas |
| DK1043995T3 (da) | 1997-12-22 | 2007-03-05 | Bayer Pharmaceuticals Corp | Inhibering af p38 kinaseaktivitet ved anvendelse af aryl- og heteroaryl-substituerede, heterocykliske urinstoffer |
| RU2265597C2 (ru) | 1997-12-22 | 2005-12-10 | Байер Копэрейшн | Арил- и гетероарилзамещенные гетероциклические производные мочевины, способ ингибирования киназы raf и фармацевтическая композиция |
| DK1047418T3 (da) | 1997-12-22 | 2005-11-21 | Bayer Pharmaceuticals Corp | Inhibering af raf-kinase ved hjælp af substituerede heterocykliske urinstoffer |
| NZ333399A (en) | 1997-12-24 | 2000-05-26 | Sankyo Co | Cyclooxygenase-2 inhibitors (COX-2) for the prevention and treatment of tumors, cachexia and tumor-metastasis |
| EP0928790B1 (en) * | 1998-01-02 | 2003-03-05 | F. Hoffmann-La Roche Ag | Thiazole derivatives |
| EP0956855B1 (en) | 1998-04-24 | 2003-03-12 | K.U. Leuven Research & Development | Immunosuppressive effects of 8 substituted xanthine derivatives |
| US6197599B1 (en) * | 1998-07-30 | 2001-03-06 | Guorong Chin | Method to detect proteins |
| 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 |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| JP2000275886A (ja) | 1999-03-23 | 2000-10-06 | Konica Corp | 電子写真感光体、それを用いたプロセスカートリッジ及び画像形成装置 |
| US6410254B1 (en) * | 1999-05-18 | 2002-06-25 | Cytokinetics | Compositions and assays utilizing ADP or phosphate for detecting protein modulators |
| US6525046B1 (en) * | 2000-01-18 | 2003-02-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as antiinflammatory agents |
| US6500628B1 (en) * | 2000-05-25 | 2002-12-31 | Millennium Pharmaceuticals, Inc. | Nucleic acid molecules encoding human kinase and phosphatase homologues and uses therefor |
| US6645990B2 (en) * | 2000-08-15 | 2003-11-11 | Amgen Inc. | Thiazolyl urea compounds and methods of uses |
| EP1506962B1 (en) * | 2000-10-20 | 2008-07-02 | Eisai R&D Management Co., Ltd. | Nitrogen-containing aromatic heterocycles |
| WO2002066442A1 (en) * | 2001-02-15 | 2002-08-29 | Boehringer Ingelheim Pharmaceuticals, Inc. | Process for synthesis of heteroaryl-substituted urea compounds useful as antiinflammatory agents |
| WO2002070662A2 (en) * | 2001-03-02 | 2002-09-12 | Gpc Biotech Ag | Three hybrid assay system |
| ATE338758T1 (de) * | 2001-03-23 | 2006-09-15 | Merck Sharp & Dohme | Imidazopyrimidin-derivate als liganden für gaba- rezeptoren |
| EP1281399A3 (en) | 2001-08-01 | 2004-02-11 | Warner-Lambert Company | Dual inhibitors of wax ester and cholesteryl ester synthesis for inhibiting sebum production |
| EP1427412A1 (en) * | 2001-09-13 | 2004-06-16 | Boehringer Ingelheim Pharmaceuticals Inc. | Methods of treating cytokine mediated diseases |
| US20040023961A1 (en) | 2002-02-11 | 2004-02-05 | Bayer Corporation | Aryl ureas with raf kinase and angiogenisis inhibiting activity |
| SI1478358T1 (sl) * | 2002-02-11 | 2013-09-30 | Bayer Healthcare Llc | Sorafenib tozilat za zdravljenje bolezni, značilnih po abnormalni angiogenezi |
| WO2003072569A1 (en) * | 2002-02-25 | 2003-09-04 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-disubstituted benzofused cycloalkyl urea compounds useful in treating cytokine mediated diseases |
| AR037647A1 (es) | 2002-05-29 | 2004-12-01 | Novartis Ag | Derivados de diarilurea utiles para el tratamiento de enfermedades dependientes de la cinasa de proteina |
| AU2003246927A1 (en) | 2002-07-03 | 2004-01-23 | Astex Technology Limited | 3-`(hetero) arylmethoxy ! pyridines and their analogues as p38 map kinase inhibitors |
| US20040138216A1 (en) | 2002-12-23 | 2004-07-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Process for the preparation of an essentially pure polymorph of an n-pyrazolyl-n'-naphthyl-urea |
| US20080045706A1 (en) * | 2002-12-31 | 2008-02-21 | Flynn Daniel L | Anti-inflammatory medicaments |
| US7202257B2 (en) * | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| US7144911B2 (en) * | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US20040171075A1 (en) * | 2002-12-31 | 2004-09-02 | Flynn Daniel L | Modulation of protein functionalities |
| EP1603879A2 (en) * | 2003-02-28 | 2005-12-14 | Bayer Pharmaceuticals Corporation | Substituted pyridine derivatives useful in the treatment of cancer and other disorders |
| US7557129B2 (en) * | 2003-02-28 | 2009-07-07 | Bayer Healthcare Llc | Cyanopyridine derivatives useful in the treatment of cancer and other disorders |
| WO2004113352A1 (en) | 2003-06-19 | 2004-12-29 | Amedis Pharmaceuticals Ltd. | Silylated heterocyclylurea derivatives as cytokine-inhibitors |
| WO2005002673A1 (en) | 2003-07-03 | 2005-01-13 | Astex Therapeutics Limited | Raf kinase inhibitors |
| EP1684762A4 (en) * | 2003-11-13 | 2009-06-17 | Ambit Biosciences Corp | UREA DERIVATIVES AS MODULATORS OF KINASE |
| US20070191336A1 (en) * | 2003-12-24 | 2007-08-16 | Flynn Daniel L | Anti-inflammatory medicaments |
| US20080220497A1 (en) * | 2003-12-24 | 2008-09-11 | Flynn Daniel L | Modulation of protein functionalities |
| AU2005321946B2 (en) * | 2004-12-23 | 2012-08-16 | Deciphera Pharmaceuticals, Llc | Enzyme modulators and treatments |
| US20090312349A1 (en) * | 2004-12-23 | 2009-12-17 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| US7622583B2 (en) * | 2005-01-14 | 2009-11-24 | Chemocentryx, Inc. | Heteroaryl sulfonamides and CCR2 |
| TW200804349A (en) | 2005-12-23 | 2008-01-16 | Kalypsys Inc | Novel substituted pyrimidinyloxy ureas as inhibitors of protein kinases |
| US7790756B2 (en) * | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| US20080248487A1 (en) * | 2007-04-09 | 2008-10-09 | Flynn Daniel L | Modulation of protein functionalities |
| US20080248548A1 (en) * | 2007-04-09 | 2008-10-09 | Flynn Daniel L | Modulation of protein functionalities |
| BRPI0807717A2 (pt) | 2007-04-20 | 2014-05-20 | Deciphera Pharmaceuticals Llc | Inibidores de quinase úteis para o tratamento de doenças mieloproliferativas e outras doenças proliferativas. |
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