CA2594860A1 - Cinnamide and hydrocinnamide derivatives with raf-kinase inhibitory activity - Google Patents

Cinnamide and hydrocinnamide derivatives with raf-kinase inhibitory activity Download PDF

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Publication number
CA2594860A1
CA2594860A1 CA002594860A CA2594860A CA2594860A1 CA 2594860 A1 CA2594860 A1 CA 2594860A1 CA 002594860 A CA002594860 A CA 002594860A CA 2594860 A CA2594860 A CA 2594860A CA 2594860 A1 CA2594860 A1 CA 2594860A1
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Prior art keywords
ring
optionally substituted
alkyl
aliphatic
independently
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CA002594860A
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English (en)
French (fr)
Inventor
Ruth S. Adams
Emily F. Calderwood
Alexandra E. Gould
Paul D. Greenspan
Matthew J. Lamarche
Yuan Tian
Tricia J. Vos
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Millennium Pharmaceuticals Inc
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Individual
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
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    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/28—Oxygen atom
    • C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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CA002594860A 2005-01-14 2006-01-12 Cinnamide and hydrocinnamide derivatives with raf-kinase inhibitory activity Abandoned CA2594860A1 (en)

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Families Citing this family (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008515961A (ja) * 2004-10-12 2008-05-15 アストラゼネカ アクチボラグ 癌に対する使用のためのキナゾリン誘導体
EP1802591B1 (en) 2004-10-12 2012-01-11 AstraZeneca AB Quinazoline derivatives
WO2007008926A1 (en) 2005-07-11 2007-01-18 Aerie Pharmaceuticals, Inc. Isoquinoline compounds
AR057455A1 (es) * 2005-07-22 2007-12-05 Merck & Co Inc Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica
US20090076075A1 (en) * 2006-03-02 2009-03-19 Frederic Henri Jung Quinoline derivatives
UY30183A1 (es) * 2006-03-02 2007-10-31 Astrazeneca Ab Derivados de quinolina
MX2008014450A (es) 2006-05-18 2009-03-09 Mannkind Corp Inhibidores de cinasa intracelular.
EP2061761A1 (en) * 2006-09-07 2009-05-27 Millennium Pharmaceuticals, Inc. Phenethylamide derivatives with kinase inhibitory activity
WO2008036540A2 (en) 2006-09-20 2008-03-27 Boehringer Ingelheim International Gmbh Rho kinase inhibitors
US8455513B2 (en) * 2007-01-10 2013-06-04 Aerie Pharmaceuticals, Inc. 6-aminoisoquinoline compounds
RU2009137190A (ru) * 2007-03-08 2011-04-20 Плексксикон, Инк. (Us) Соединения, обладающие активностью в отношении ppar
US8455514B2 (en) 2008-01-17 2013-06-04 Aerie Pharmaceuticals, Inc. 6-and 7-amino isoquinoline compounds and methods for making and using the same
US8822513B2 (en) 2010-03-01 2014-09-02 Gtx, Inc. Compounds for treatment of cancer
US9447049B2 (en) 2010-03-01 2016-09-20 University Of Tennessee Research Foundation Compounds for treatment of cancer
AU2009330686B2 (en) 2008-06-16 2014-07-03 The Ohio State University Research Foundation Compounds for the treatment of cancer
US9029408B2 (en) 2008-06-16 2015-05-12 Gtx, Inc. Compounds for treatment of cancer
TWI546290B (zh) 2008-06-27 2016-08-21 賽基艾維洛米斯研究股份有限公司 雜芳基化合物及其用途
US11351168B1 (en) 2008-06-27 2022-06-07 Celgene Car Llc 2,4-disubstituted pyrimidines useful as kinase inhibitors
US8338439B2 (en) 2008-06-27 2012-12-25 Celgene Avilomics Research, Inc. 2,4-disubstituted pyrimidines useful as kinase inhibitors
WO2010006792A1 (de) * 2008-07-16 2010-01-21 Bitop Ag Synthese von zyklischen amidinen
US8450344B2 (en) 2008-07-25 2013-05-28 Aerie Pharmaceuticals, Inc. Beta- and gamma-amino-isoquinoline amide compounds and substituted benzamide compounds
EP2179984A1 (en) * 2008-10-27 2010-04-28 Congenia S.r.l. Acrylamido derivatives useful as inhibitors of the mitochondrial permeability transition
EP3053913B1 (en) 2009-05-01 2018-03-07 Aerie Pharmaceuticals, Inc. Dual mechanism inhibitors for the treatment of disease
KR101705158B1 (ko) 2009-05-05 2017-02-09 다나-파버 캔서 인스티튜트 인크. Ｅｇｆｒ 억제제 및 질환 치료방법
MX2012010115A (es) 2010-03-01 2013-02-26 Gtx Inc Compuestos para el tratamiento de cancer.
CN105566229A (zh) 2010-08-10 2016-05-11 西建阿维拉米斯研究公司 Btk抑制剂的苯磺酸盐及其用途和制备方法
MX382354B (es) 2010-11-01 2025-03-13 Celgene Car Llc Compuestos heterocíclicos y usos de los mismos.
EP2635285B1 (en) 2010-11-01 2017-05-03 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
JP5957003B2 (ja) 2010-11-10 2016-07-27 セルジーン アヴィロミクス リサーチ， インコーポレイテッド 変異体選択的ｅｇｆｒ阻害剤およびその使用
AR088570A1 (es) 2011-10-28 2014-06-18 Celgene Avilomics Res Inc Metodos para tratar una enfermedad o trastorno relacionado con la tirosina quinasa de bruton
US9408885B2 (en) 2011-12-01 2016-08-09 Vib Vzw Combinations of therapeutic agents for treating melanoma
PL2825042T3 (pl) 2012-03-15 2019-02-28 Celgene Car Llc Sole inhibitora kinazy receptora czynnika wzrostu naskórka
KR102081042B1 (ko) 2012-03-15 2020-02-26 셀젠 카르 엘엘씨 상피 성장 인자 수용체 키나제 억제제의 고체 형태
BR112014027700A2 (pt) * 2012-05-08 2017-06-27 Ishihara Sangyo Kaisha método para produção de um composto de ácido benzoico substituído
CN103508961B (zh) * 2012-06-26 2015-07-22 中美冠科生物技术（太仓）有限公司 抗肿瘤药物
US20150225369A1 (en) * 2012-08-29 2015-08-13 Merck Patent Gmbh Ddr2 inhibitors for the treatment of osteoarthritis
US9126950B2 (en) 2012-12-21 2015-09-08 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
AU2014214846A1 (en) 2013-02-08 2015-07-23 Celgene Avilomics Research, Inc. ERK inhibitors and uses thereof
DK3811943T3 (da) 2013-03-15 2023-04-03 Aerie Pharmaceuticals Inc Forbindelse til anvendelse til behandling af øjenlidelser
US9492471B2 (en) 2013-08-27 2016-11-15 Celgene Avilomics Research, Inc. Methods of treating a disease or disorder associated with Bruton'S Tyrosine Kinase
US9415049B2 (en) 2013-12-20 2016-08-16 Celgene Avilomics Research, Inc. Heteroaryl compounds and uses thereof
HRP20220522T1 (hr) 2014-08-04 2022-06-10 Nuevolution A/S Proizvoljno kondenzirani heterociklil-supstituirani derivati pirimidina koji su korisni za liječenje upalnih, metaboličkih, onkoloških i autoimunih bolesti
US10005760B2 (en) 2014-08-13 2018-06-26 Celgene Car Llc Forms and compositions of an ERK inhibitor
CN106146395B (zh) * 2015-03-27 2019-01-01 沈阳三生制药有限责任公司 3-羟基吡啶化合物、其制备方法及其制药用途
US9643927B1 (en) 2015-11-17 2017-05-09 Aerie Pharmaceuticals, Inc. Process for the preparation of kinase inhibitors and intermediates thereof
US10550087B2 (en) 2015-11-17 2020-02-04 Aerie Pharmaceuticals, Inc. Process for the preparation of kinase inhibitors and intermediates thereof
KR102568079B1 (ko) 2016-08-31 2023-08-17 에어리 파마슈티컬즈, 인코포레이티드 안과용 조성물
JP7341060B2 (ja) 2017-02-10 2023-09-08 アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル Ｍａｐｋ経路の活性化に関連付けられる癌の処置のための方法及び医薬組成物
KR20190135027A (ko) 2017-03-31 2019-12-05 에어리 파마슈티컬즈, 인코포레이티드 아릴 시클로프로필-아미노-이소퀴놀리닐 아미드 화합물
EP3732285A1 (en) 2017-12-28 2020-11-04 Tract Pharmaceuticals, Inc. Stem cell culture systems for columnar epithelial stem cells, and uses related thereto
AU2019337703B2 (en) 2018-09-14 2023-02-02 Aerie Pharmaceuticals, Inc. Aryl cyclopropyl-amino-isoquinolinyl amide compounds
CN111233774B (zh) * 2018-11-28 2023-04-14 鲁南制药集团股份有限公司 一种胺基嘧啶类化合物
MX2022007265A (es) 2019-12-20 2022-09-09 Nuevolution As Compuestos activos frente a receptores nucleares.
US11685727B2 (en) 2019-12-20 2023-06-27 Nuevolution A/S Compounds active towards nuclear receptors
CA3174176A1 (en) 2020-03-31 2021-10-07 Sanne Schroder Glad Compounds active towards nuclear receptors
EP4126874A1 (en) 2020-03-31 2023-02-08 Nuevolution A/S Compounds active towards nuclear receptors

Family Cites Families (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE668367A (https=)
US2415554A (en) * 1947-02-11 Oh nh-cc
AU598750B2 (en) * 1985-09-27 1990-07-05 Mitsubishi Chemical Corporation Phenylalanine derivative and proteinase inhibitor
US4873253A (en) * 1987-03-30 1989-10-10 Shosuke Okamoto Phenylalanine derivative and proteinase inhibitor
JPH07113758B2 (ja) * 1988-03-28 1995-12-06 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
AU3737289A (en) 1988-06-06 1990-01-05 Okamoto, Shosuke Agent for treating pancreatitis or the like
TW202452B (https=) 1989-12-01 1993-03-21 Ciba Geigy Ag
EP0459702A1 (en) 1990-05-29 1991-12-04 Zeneca Limited Azole Derivatives
US5356894A (en) * 1990-05-29 1994-10-18 Rodney Peter W Morpholinyl substituted [1,2,4]-triazolo[1,5-a]triazine as antagonist
DE69216873T2 (de) * 1991-02-21 1997-08-21 Sankyo Co Benzolderivate zum Fördern der Produktion des Nervenwachstumsfaktors
JP2739260B2 (ja) 1991-04-10 1998-04-15 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
WO1993015043A1 (fr) 1992-01-24 1993-08-05 Yoshitomi Pharmaceutical Industries, Ltd. Compose arylalkananilide et utilisation pharmaceutique
ES2079315B1 (es) * 1994-02-24 1996-10-16 Uriach & Cia Sa J Nuevas imidazopiridinas.
ATE251141T1 (de) 1995-03-10 2003-10-15 Berlex Lab Benzamidin-derivate, deren herstellung und deren verwendung als anti-koagulantien
US5763463A (en) * 1995-04-28 1998-06-09 Kumiai Chemical Industry Co., Ltd. Pyridine compounds which are useful as pesticides
NO307879B1 (no) * 1995-09-18 2000-06-13 Sankyo Co Nye ureaderivater med ACAT-inhiberende aktivitet og farmasøytisk preparat inneholdende disse
AUPO252896A0 (en) 1996-09-24 1996-10-17 Fujisawa Pharmaceutical Co., Ltd. Amidine derivatives
GB9623833D0 (en) * 1996-11-16 1997-01-08 Zeneca Ltd Chemical compound
US5990147A (en) * 1997-11-07 1999-11-23 Schering Corporation H3 receptor ligands of the phenyl-alkyl-imidazoles type
CA2309121A1 (en) 1997-11-07 1999-05-20 Schering Corporation Phenyl-alkyl-imidazoles as h3 receptor antagonists
US6034251A (en) * 1997-11-07 2000-03-07 Schering Corporation Phenyl-alkyl-imidazoles
CA2308586A1 (en) 1997-11-07 1999-05-20 Schering Corporation H3 receptor ligands of the phenyl-alkyl-imidazoles type
US6593322B1 (en) 1999-03-17 2003-07-15 Signal Pharmaceuticals, Inc. Compounds and methods for modulation of estrogen receptors
GB9922173D0 (en) 1999-09-21 1999-11-17 Zeneca Ltd Chemical compounds
PL358271A1 (pl) 2000-03-06 2004-08-09 Warner-Lambert Company 5-alkilopirydo[2,3-D]pirymidyny jako inhibitory kinazy tyrozyny
KR20020081424A (ko) 2000-03-09 2002-10-26 아벤티스 파마 도이칠란트 게엠베하 Ｐｐａｒ 매개인자의 치료학적 용도
US6642252B2 (en) 2000-11-07 2003-11-04 Bristol-Myers Squibb Company Acid derivatives useful as serine protease inhibitors
US7235576B1 (en) * 2001-01-12 2007-06-26 Bayer Pharmaceuticals Corporation Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors
MXPA04001253A (es) * 2001-08-09 2004-06-03 Ono Pharmaceutical Co Derivados de acidos carboxilicos y agente farmaceutico que comprende los mismos como ingrediente activo.
EP1435946B8 (en) 2001-09-14 2013-12-18 Amgen Inc. Linked biaryl compounds
BR0305426A (pt) 2002-07-01 2004-08-24 Upjohn Co Compostos inibidores de ns5b polimerase de hcv, bem como composição farmacêutica compreendendo os mesmos
DE60322544D1 (de) 2002-08-27 2008-09-11 Merck Patent Gmbh Glycinamid-derivate als raf-kinase-hemmer
BR0316680A (pt) * 2002-11-28 2005-10-18 Schering Ag Pirimidinas inibidoras de chk, pdk e akt, sua produção e uso como agentes farmacêuticos
US20040198743A1 (en) * 2003-01-31 2004-10-07 Schering Corporation Methods for treating allergic skin and allergic ocular conditions using combinations of histamine receptor antagonists
ATE406360T1 (de) 2003-03-07 2008-09-15 Lilly Co Eli Antagonisten der opioidrezeptoren
DE10335725A1 (de) * 2003-08-05 2005-03-03 Bayer Cropscience Gmbh Safener auf Basis aromatisch-aliphatischer Carbonsäuredarivate
GB0319124D0 (en) 2003-08-14 2003-09-17 Smithkline Beecham Corp Chemical compounds
EP1663204B1 (en) 2003-08-29 2014-05-07 Exelixis, Inc. C-kit modulators and methods of use
WO2005028467A1 (en) 2003-09-15 2005-03-31 Anadys Pharmaceuticals, Inc. Antibacterial 3,5-diaminopiperidine-substitute aromatic and heteroaromatic compounds
MX2007001215A (es) 2004-08-06 2007-04-17 Otsuka Pharma Co Ltd Compuestos aromaticos.

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