AU2004298511B2 - Compounds for treatment of cell proliferative diseases - Google Patents
Compounds for treatment of cell proliferative diseases Download PDFInfo
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- AU2004298511B2 AU2004298511B2 AU2004298511A AU2004298511A AU2004298511B2 AU 2004298511 B2 AU2004298511 B2 AU 2004298511B2 AU 2004298511 A AU2004298511 A AU 2004298511A AU 2004298511 A AU2004298511 A AU 2004298511A AU 2004298511 B2 AU2004298511 B2 AU 2004298511B2
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- C07D213/02—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
- 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
- C07D213/61—Halogen atoms or nitro radicals
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| PT1701941E (pt) | 2003-12-11 | 2012-08-03 | Univ Texas | Compostos para o tratamento de doenças proliferativas celulares |
| ZA200803226B (en) * | 2005-10-13 | 2009-11-25 | Orchid Res Lab Ltd | Heterocyclic Compounds as Pstat3/IL-6 Inhibitors |
| RU2456265C2 (ru) * | 2006-03-31 | 2012-07-20 | Дзе Борд Оф Риджентс Оф Дзе Юниверсити Оф Техас Систем | Биологически доступная для перорального применения кофейная кислота, относящаяся к противоопухолевым лекарственным средствам |
| US20100292229A1 (en) * | 2006-06-30 | 2010-11-18 | The Board Of Regents Of The University Of Texas System | Tryphostin-analogs for the treatment of cell proliferative diseases |
| KR20140097446A (ko) | 2006-11-20 | 2014-08-06 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 통증 및 소양증 치료용 방법, 조성물 및 키트 |
| WO2008083389A1 (en) * | 2006-12-29 | 2008-07-10 | Moleculin, L.L.C. | Methods of treating skin disorders with caffeic acid analogs |
| US20100144802A1 (en) * | 2007-03-28 | 2010-06-10 | Heimberger Amy B | Small Molecule Inhibitors for Immune Modulation |
| JP5688840B2 (ja) * | 2007-09-10 | 2015-03-25 | ボストン バイオメディカル， インコーポレイテッド | 新規のＳｔａｔ３経路阻害剤及び癌幹細胞阻害剤 |
| ES2521676T3 (es) | 2008-07-08 | 2014-11-13 | Board Of Regents, The University Of Texas System | Nuevos agentes inhibidores de la proliferación y de la activación de transductores de señales y activadores de la transcripción (STATS) |
| ES2743412T3 (es) | 2008-09-30 | 2020-02-19 | Curium Us Llc | Productos conjugados de hexosa y compuestos de coordinación de metales para la generación de imágenes |
| US8450337B2 (en) * | 2008-09-30 | 2013-05-28 | Moleculin, Llc | Methods of treating skin disorders with caffeic acid analogs |
| US20120021941A1 (en) * | 2009-01-12 | 2012-01-26 | The Board Of Regents Of The University Of Texas System | Blood test for the detection of cancer |
| EP3485881B1 (en) | 2009-07-10 | 2024-03-13 | President and Fellows of Harvard College | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| JP5940452B2 (ja) | 2009-10-16 | 2016-06-29 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 殺菌剤としてのアミノプロペン酸化合物 |
| WO2011069141A2 (en) | 2009-12-04 | 2011-06-09 | Board Of Regents, The University Of Texas System | Interferon therapies in combination with blockade of stat3 activation |
| EP2544686A4 (en) | 2010-02-05 | 2013-06-26 | Whitehead Biomedical Inst | COMBINATION PROCEDURE FOR THE TREATMENT OF A DISEASE |
| LT2547205T (lt) | 2010-03-19 | 2024-06-10 | 1Globe Biomedical Co., Ltd. | Nauji tikslinio poveikio vėžio kamieninėms ląstelėms būdai |
| JP5852658B2 (ja) * | 2010-09-24 | 2016-02-03 | ザ リージェンツ オブ ザ ユニバーシティー オブ ミシガン | デユビキチナーゼ阻害剤およびその使用方法 |
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| CA2927023C (en) * | 2013-10-10 | 2022-08-02 | The Regents Of The University Of Michigan | Deubiquitinase inhibitors and methods for use of the same |
| WO2016069906A1 (en) | 2014-10-29 | 2016-05-06 | Massachusetts Eye And Ear Infirmary | Efficient delivery of therapeutic molecules to cells of the inner ear |
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| CA3062656A1 (en) | 2017-05-17 | 2018-11-22 | Boston Biomedical, Inc. | Methods for treating cancer |
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| EP3743057A4 (en) | 2018-01-26 | 2021-11-17 | Massachusetts Eye & Ear Infirmary | TREATMENT OF HEARING LOSS |
| US10786485B1 (en) | 2019-03-11 | 2020-09-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| BR112021017772A2 (pt) | 2019-03-11 | 2021-11-16 | Nocion Therapeutics Inc | Bloqueadores de canais de íons carregados e métodos para uso |
| EP3937945A4 (en) | 2019-03-11 | 2023-01-04 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
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| AU2020252372A1 (en) * | 2019-04-02 | 2021-10-28 | Board Of Regents, The University Of Texas System | Combinations of transcription inhibitors and immune checkpoint inhibitors for treatment of disease |
| CA3135802A1 (en) | 2019-04-05 | 2020-10-08 | Kymera Therapeutics, Inc. | Stat degraders and uses thereof |
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| WO2021091585A1 (en) | 2019-11-06 | 2021-05-14 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US12162851B2 (en) | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| EP4118070A4 (en) | 2020-03-11 | 2024-04-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| CN115381822A (zh) * | 2022-05-11 | 2022-11-25 | 暨南大学附属第一医院（广州华侨医院） | 一种基于激活免疫应答治疗肺癌的药物及制药应用 |
| KR102811597B1 (ko) * | 2022-06-22 | 2025-05-22 | 한국생명공학연구원 | 신규한 신남아마이드 유도체 및 이의 용도 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2555789A1 (de) * | 1975-12-11 | 1977-07-07 | Hoechst Ag | Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| WO1998006391A1 (en) * | 1996-08-14 | 1998-02-19 | Mor-Research Applications Ltd. | Pharmaceutical compositions comprising tyrphostins |
| EP1000935A1 (en) * | 1997-07-25 | 2000-05-17 | TSUMURA & CO. | PYRIDYLACRYLAMIDE DERIVATIVES AND NEPHRITIS REMEDIES AND TGF-$g(b) INHIBITORS CONTAINING THE SAME |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2629455B1 (fr) * | 1988-03-29 | 1991-09-27 | Rhone Poulenc Agrochimie | Derives de 2-(3-pyridinyl)3-(phenoxy) propanenitrile |
| GB9004483D0 (en) * | 1990-02-28 | 1990-04-25 | Erba Carlo Spa | New aryl-and heteroarylethenylene derivatives and process for their preparation |
| US5196446A (en) * | 1990-04-16 | 1993-03-23 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Certain indole compounds which inhibit EGF receptor tyrosine kinase |
| WO1991016305A1 (en) | 1990-04-16 | 1991-10-31 | Rhone-Poulenc Rorer International (Holdings), Inc. | Heterocyclicethenediyl compounds which inhibit egf receptor tyrosine kinase |
| JPH05301838A (ja) * | 1991-10-15 | 1993-11-16 | Mitsubishi Kasei Corp | スチレン誘導体 |
| CA2080554A1 (en) * | 1991-10-15 | 1993-04-16 | Mitsubishi Chemical Corporation | Styrene derivatives |
| CA2092017A1 (en) | 1992-03-26 | 1993-09-27 | Tameo Iwasaki | Butadiene derivatives and process for preparing the same |
| US5981569A (en) * | 1992-11-13 | 1999-11-09 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Substituted phenylacrylonitrile compounds and compositions thereof for the treatment of disease |
| JPH06247850A (ja) | 1993-02-24 | 1994-09-06 | Suntory Ltd | １２−リポキシゲナーゼ阻害剤 |
| US5823706A (en) | 1993-07-27 | 1998-10-20 | The University Of Birmingham | Pavements |
| GB9322781D0 (en) * | 1993-11-04 | 1993-12-22 | Roussel Lab Ltd | Aromatic amides |
| IL107736A (en) | 1993-11-24 | 2001-01-11 | Yissum Res Dev Co | Pharmaceutical composition for the prevention of septic shock and for the treatment of chronic inflammatory diseases |
| IL112205A0 (en) | 1994-01-06 | 1995-03-15 | Res Dev Foundation | Curcumin, analogues of curcumin and novel uses thereof |
| US5700823A (en) | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
| WO1995024190A2 (en) * | 1994-03-07 | 1995-09-14 | Sugen, Inc. | Receptor tyrosine kinase inhibitors for inhibiting cell proliferative disorders and compositions thereof |
| GB9406137D0 (en) * | 1994-03-28 | 1994-05-18 | Erba Carlo Spa | N-substituted beta-aryl- and betaheteroaryl-alpha-cyanoacrylamide derivatives and process for their preparation |
| AU2360595A (en) | 1994-04-22 | 1995-11-16 | Hospital For Sick Children Research and Developement Limited Partnership, The | Use of benzylidene-malononitrile derivates for the treatment of leukemia |
| US6331555B1 (en) * | 1995-06-01 | 2001-12-18 | University Of California | Treatment of platelet derived growth factor related disorders such as cancers |
| US5854285A (en) * | 1997-04-03 | 1998-12-29 | Natpro, Inc. | Protein kinase inhibitor |
| US6420338B1 (en) * | 1997-06-13 | 2002-07-16 | New York University Medical Center | Inhibition of the Src kinase family pathway as a method of treating HBV infection and hepatocellular carcinoma |
| US6225346B1 (en) * | 1997-10-24 | 2001-05-01 | Sugen, Inc. | Tyrphostin like compounds |
| WO2000052062A1 (fr) | 1999-03-04 | 2000-09-08 | Riken | Composition de catalyseur |
| US20020045191A1 (en) * | 2000-09-15 | 2002-04-18 | Schneider Robert J. | Inhibition of the SRC kinase family pathway as a method of treating HBV infection and hepatocellular carcinoma |
| JP2003119169A (ja) | 2001-07-30 | 2003-04-23 | Shigetoshi Kadota | 細胞毒性活性を有する化合物およびそれを有効成分とする医薬組成物 |
| US6433018B1 (en) | 2001-08-31 | 2002-08-13 | The Research Foundation Of State University Of New York | Method for reducing hypertrophy and ischemia |
| WO2003045367A1 (en) | 2001-11-30 | 2003-06-05 | Santen Pharmaceutical Co., Ltd. | Angiogenesis inhibitor |
| AU2003210983A1 (en) | 2002-02-11 | 2003-09-04 | The Brigham And Women's Hospital, Inc. | Kinase inhibitors and methods of use thereof |
| AU2003294441A1 (en) | 2002-11-22 | 2004-06-18 | Bristol-Myers Squibb Company | 1-aryl-2-hydroxyethyl amides as potassium channel openers |
| KR20050055479A (ko) | 2003-12-08 | 2005-06-13 | 김철호 | 카페인산 또는 카페인산 페네틸에스테르를 유효성분으로하는 ｍｍｐ-9 억제제 |
| PT1701941E (pt) * | 2003-12-11 | 2012-08-03 | Univ Texas | Compostos para o tratamento de doenças proliferativas celulares |
| RU2456265C2 (ru) * | 2006-03-31 | 2012-07-20 | Дзе Борд Оф Риджентс Оф Дзе Юниверсити Оф Техас Систем | Биологически доступная для перорального применения кофейная кислота, относящаяся к противоопухолевым лекарственным средствам |
| US20100292229A1 (en) | 2006-06-30 | 2010-11-18 | The Board Of Regents Of The University Of Texas System | Tryphostin-analogs for the treatment of cell proliferative diseases |
| WO2008053297A2 (en) * | 2006-10-30 | 2008-05-08 | Wockhardt Research Centre | Pharmaceutical compositions comprising entacapone, levodopa, and carbidopa |
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- 2004-12-13 WO PCT/US2004/041712 patent/WO2005058829A1/en not_active Ceased
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- 2006-05-30 IL IL176028A patent/IL176028A/en active IP Right Review Request
- 2006-06-07 ZA ZA2006/04682A patent/ZA200604682B/en unknown
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- 2010-06-28 US US12/824,901 patent/US8119827B2/en not_active Expired - Fee Related
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- 2012-01-13 US US13/350,637 patent/US8648102B2/en not_active Expired - Lifetime
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- 2014-01-03 US US14/147,089 patent/US9096499B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2555789A1 (de) * | 1975-12-11 | 1977-07-07 | Hoechst Ag | Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| WO1998006391A1 (en) * | 1996-08-14 | 1998-02-19 | Mor-Research Applications Ltd. | Pharmaceutical compositions comprising tyrphostins |
| EP1000935A1 (en) * | 1997-07-25 | 2000-05-17 | TSUMURA & CO. | PYRIDYLACRYLAMIDE DERIVATIVES AND NEPHRITIS REMEDIES AND TGF-$g(b) INHIBITORS CONTAINING THE SAME |
Non-Patent Citations (4)
| Title |
|---|
| Abdel-Latif, F.F., et al, 'Heterocycles synthesis through reactions of nucleophiles with acrylonitriles: Part III', Indian Journal of Chemistry, 1990, vol. 29B, pp 322-5 * |
| Holmes, H.L., 'Structure-Activity Relationships for some Conjugated Heteroenoid Compounds, Catechol Monoethers and Morphine Alkaloids', Defence Research Establishment Suffield, Ralston, Alberta, Canada, 1975, pages 649 to 660 * |
| McCluskey, A., et al, 'Green chemistry approaches to the Knoevenagel condensation: comparison of ethanol, water, and solvent free (dry grind) approaches', Tetrahedron Letters, 2002, vol. 43, pp 3117-20 * |
| Tamiz, A.P., et al, 'Structure-Activity Relationship of N-(Phenylalkyl)cinnamides as Novel NR2B Subtype-Selective NMDA Receptor Antagonists', Journal of Medicinal Chemistry, 1999, vol. 42, pp 3412-20 * |
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