PT2953938T - Compostos de benzopirano funcionais e sua utilização - Google Patents
Compostos de benzopirano funcionais e sua utilização Download PDFInfo
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- PT2953938T PT2953938T PT157462110T PT15746211T PT2953938T PT 2953938 T PT2953938 T PT 2953938T PT 157462110 T PT157462110 T PT 157462110T PT 15746211 T PT15746211 T PT 15746211T PT 2953938 T PT2953938 T PT 2953938T
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
-
- 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
- A61P35/04—Antineoplastic agents specific for metastasis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US10265294B2 (en) * | 2016-03-31 | 2019-04-23 | Yale University | Compositions and methods for treating epithelial cancer |
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| US4447622A (en) | 1981-09-22 | 1984-05-08 | Council Of Scientific And Industrial Research Rafi Marg | Preparation of l- and d-isomers of dl-3,4-trans-2,2-disubstituted-3,4-diarylchromans and derivatives thereof |
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| US5280040A (en) | 1993-03-11 | 1994-01-18 | Zymogenetics, Inc. | Methods for reducing bone loss using centchroman derivatives |
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| CN1168098A (zh) | 1995-01-13 | 1997-12-17 | 诺沃挪第克公司 | 3,4-二苯基苯并二氢吡喃在生产用于治疗或预防高脂蛋白血症、高甘油三酯血症、高脂血症或高胆固醇血症或动脉硬化或用于抗凝治疗的药物组合物中的用途 |
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| ES2191170T3 (es) | 1996-10-28 | 2003-09-01 | Novo Nordisk As | Nuevos (-)-enantiomeros de derivados de cis-3,4-cromano utiles en la prevencion y tratamiento de sindromes o enfermedades relacionadas con el estrogeno. |
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| AU5550298A (en) | 1997-01-29 | 1998-08-25 | Novo Nordisk A/S | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical compositionfor increasing libido in post-menopausal women |
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| US6184005B1 (en) | 1998-04-28 | 2001-02-06 | Novo Nordisk A/S | Enzymatic resolvation for obtaining a (−)-3,4-trans-diarylchroman |
| IL142082A (en) * | 1998-09-23 | 2005-12-18 | Res Dev | Tocoflowers, tocotrinols, derivatives as a novel and other side-chain and their uses |
| WO2001007031A1 (en) | 1999-07-26 | 2001-02-01 | Shionogi & Co., Ltd. | Benzene derivatives and immunopotentiating compositions or drug-sensitivity restoring agents containing the same |
| JP2004510815A (ja) | 2000-10-13 | 2004-04-08 | アストラゼネカ・アクチエボラーグ | エストロゲン受容体−βリガンド |
| US20050119301A1 (en) | 2001-03-16 | 2005-06-02 | Alan Husband | Treatment of restenosis |
| WO2002074307A1 (en) | 2001-03-16 | 2002-09-26 | Novogen Research Pty Ltd | Treatment of restenosis |
| WO2003063859A1 (en) | 2002-01-14 | 2003-08-07 | Nordic Bioscience A/S | Suppression of cartilage degradation via the estrogen receptor |
| US20040167165A1 (en) | 2003-01-16 | 2004-08-26 | Geetha Shankar | Methods of treating conditions associated with an Edg-7 receptor |
| JPWO2004108944A1 (ja) | 2003-06-04 | 2006-07-20 | 三菱瓦斯化学株式会社 | 光学活性クロマンカルボン酸エステルの製造方法 |
| CN101123958A (zh) * | 2003-11-19 | 2008-02-13 | 诺沃根研究股份有限公司 | 联合放射疗法与化学疗法的组合物和方法 |
| JP4976649B2 (ja) * | 2004-09-21 | 2012-07-18 | マーシャル エドワーズ，インク． | 化合物 |
| US8080675B2 (en) | 2004-09-21 | 2011-12-20 | Marshall Edwards, Inc. | Chroman derivatives, medicaments and use in therapy |
| EP2436680B1 (en) * | 2004-09-21 | 2016-05-18 | Marshall Edwards, Inc. | Chroman derivatives, medicaments and use in therapy |
| ES2377073T3 (es) * | 2004-09-21 | 2012-03-22 | Marshall Edwards, Inc. | Derivados de cromano sustituidos, medicamentos y utilización en terapia |
| CN101056868B (zh) | 2004-09-21 | 2012-05-02 | 马休爱德华兹股份有限公司 | 取代的苯并二氢吡喃衍生物、药物及其在治疗中的应用 |
| US7528267B2 (en) | 2005-08-01 | 2009-05-05 | Girindus America, Inc. | Method for enantioselective hydrogenation of chromenes |
| WO2007096362A1 (en) | 2006-02-21 | 2007-08-30 | Trigen Limited | Heterocyclic compounds and their use in the treatment of cardiovascular disease |
| CA2668008A1 (en) | 2006-10-30 | 2008-05-08 | Novogen Research Pty Ltd | Prevention and reversal of chemotherapy-induced peripheral neuropathy |
| CN101210012B (zh) | 2006-12-31 | 2011-09-14 | 南华大学 | 新的含烟酸异黄酮酯衍生物及其制造方法和用途 |
| CA2738328A1 (en) | 2008-08-29 | 2010-03-04 | Novogen Research Pty Ltd | Immunomodulating activities |
| AU2008230055A1 (en) | 2008-10-22 | 2010-05-06 | Novogen Research Pty Ltd | Methods for Inducing Programmed Cell Death |
| CN102596196A (zh) | 2008-10-22 | 2012-07-18 | 诺沃根研究控股有限公司 | 用于诱导程序性细胞死亡的方法 |
| WO2011115819A2 (en) | 2010-03-15 | 2011-09-22 | Genus Oncology, Llc | Small molecule inhibitors of muc1 and methods of identifying the same |
| WO2011156889A1 (en) | 2010-06-14 | 2011-12-22 | Trt Pharma Inc. | Novel modulators of nrf2 and uses thereof |
| WO2012061409A1 (en) * | 2010-11-01 | 2012-05-10 | Marshall Edwards, Inc. | Isoflavonoid compounds and methods for the treatment of cancer |
| CN102153535A (zh) | 2011-03-04 | 2011-08-17 | 中国海洋大学 | 一种抗肿瘤多药耐药抑制剂苯并吡喃-3-醇酯化衍生物及其制备方法和应用 |
| US20120251630A1 (en) * | 2011-03-29 | 2012-10-04 | Marshall Edwards, Inc. | Remission therapy of cancer with isoflavonoids |
| US20150018566A1 (en) * | 2011-08-25 | 2015-01-15 | The Provost, Fellows, Foundation Scholars, & the Other Members of Board, of The College of the Holy | Tubulin binding agents |
| CA2985787A1 (en) | 2012-06-07 | 2013-12-12 | Georgia State University Research Foundation, Inc. | Seca inhibitors and methods of making and using thereof |
| CN103408528B (zh) | 2013-08-13 | 2015-04-29 | 浙江大学 | 一种色满化合物及其制备方法和应用 |
| CN103450142B (zh) | 2013-09-04 | 2015-03-25 | 浙江大学 | 一种色满化合物及其提取方法和应用 |
| CN103585145A (zh) | 2013-11-28 | 2014-02-19 | 常州科立信医疗器械有限公司 | Artoxanthochromane在治疗前列腺癌药物中的应用 |
| CN103638008B (zh) | 2013-12-02 | 2015-09-16 | 刘艳娇 | Artoxanthochromane在治疗皮肤癌药物中的应用 |
| CN103690525A (zh) | 2013-12-02 | 2014-04-02 | 常州科立信医疗器械有限公司 | Artoxanthochromane在治疗舌癌药物中的应用 |
| CN103705503A (zh) | 2013-12-04 | 2014-04-09 | 常州科立信医疗器械有限公司 | Artoxanthochromane在治疗乳腺癌药物中的应用 |
| ES2643407T3 (es) * | 2014-02-07 | 2017-11-22 | Novogen Ltd. | Compuestos de benzopirano funcionalizados y uso de los mismos |
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