ES2643407T3 - Compuestos de benzopirano funcionalizados y uso de los mismos - Google Patents
Compuestos de benzopirano funcionalizados y uso de los mismos Download PDFInfo
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- ES2643407T3 ES2643407T3 ES15746211.0T ES15746211T ES2643407T3 ES 2643407 T3 ES2643407 T3 ES 2643407T3 ES 15746211 T ES15746211 T ES 15746211T ES 2643407 T3 ES2643407 T3 ES 2643407T3
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Classifications
-
- 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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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| US201461937368P | 2014-02-07 | ||
| US201461987323P | 2014-05-01 | 2014-05-01 | |
| US201461987323P | 2014-05-01 | ||
| PCT/AU2015/050040 WO2015117202A1 (en) | 2014-02-07 | 2015-02-05 | Functionalised benzopyran compounds and use thereof |
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| ES2643407T3 true ES2643407T3 (es) | 2017-11-22 |
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| ES15746211.0T Active ES2643407T3 (es) | 2014-02-07 | 2015-02-05 | Compuestos de benzopirano funcionalizados y uso de los mismos |
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| ES2877712T3 (es) | 2015-02-02 | 2021-11-17 | Mei Pharma Inc | Terapias combinadas para su uso en el tratamiento del cáncer de mama |
| US10265294B2 (en) * | 2016-03-31 | 2019-04-23 | Yale University | Compositions and methods for treating epithelial cancer |
| CA3058492A1 (en) * | 2016-04-06 | 2017-10-12 | Noxopharm Limited | Radiotherapy improvements |
| AU2017247008B2 (en) | 2016-04-06 | 2022-04-07 | Noxopharm Limited | Isoflavonoid composition with improved pharmacokinetics |
| CN109793737B (zh) * | 2017-03-01 | 2021-06-29 | 浙江大学 | 苯磺酰胺结构类型雄激素受体拮抗剂及其应用 |
| EP4125870A1 (en) | 2020-03-30 | 2023-02-08 | Noxopharm Limited | Methods for the treatment of inflammation associated with infection |
| WO2021252776A1 (en) * | 2020-06-11 | 2021-12-16 | Mei Pharma, Inc. | Combination therapies |
| WO2023235929A1 (en) * | 2022-06-08 | 2023-12-14 | Noxopharm Limited | Functionalised benzopyran compounds and uses thereof |
| CN118005594B (zh) * | 2023-05-24 | 2024-10-29 | 内蒙古大学 | 3-羟基苯并二氢吡喃衍生物的合成及其抗肿瘤活性 |
Family Cites Families (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3340276A (en) | 1964-04-01 | 1967-09-05 | Ciba Geigy Corp | 3, 4-diphenyl-chromans |
| US3822287A (en) | 1969-04-17 | 1974-07-02 | Rexall Drug Chemical | Process for preparation of substituted 3,4-(diphenyl)chromans |
| 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 |
| BE891562A (fr) | 1981-12-21 | 1982-04-16 | Council Scient Ind Res | Isomeres 1 et d de d1-3, 4-trans-3, 4-diarylchromanes 2, 2-disubstitues et leurs derives, leur preparation et leur utilisation |
| US5280040A (en) | 1993-03-11 | 1994-01-18 | Zymogenetics, Inc. | Methods for reducing bone loss using centchroman derivatives |
| US5451603A (en) | 1993-03-11 | 1995-09-19 | Zymogenetics, Inc. | 3,4-diarylchromans for treatment of dermatitis |
| WO1996021442A1 (en) | 1995-01-13 | 1996-07-18 | Novo Nordisk A/S | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for the treatment of prophylaxis of idiopathic or physiologic gynaecomastia |
| WO1996021443A1 (en) | 1995-01-13 | 1996-07-18 | Novo Nordisk A/S | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of hyperlipoproteinaemia, hypertriglyceridaemia, hyperlipidaemia or hypercholesterolaemia or arteriosclerosis or for anticoagulative treatment |
| HUP9702244A3 (en) | 1995-01-13 | 1999-12-28 | Novo Nordisk As | Use of 3,4-diphenyl chromans for manufacture of a pharmaceutical composition for treatment or prophylaxis of gynaecological disorders |
| CA2208856A1 (en) | 1995-01-20 | 1996-07-25 | Novo Nordisk A/S | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of cerebral degenerative disorders |
| AU4329196A (en) | 1995-01-20 | 1996-08-07 | Novo Nordisk A/S | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for vasodilatory treatment or prophylaxis |
| TW448046B (en) | 1995-01-20 | 2001-08-01 | Novo Nordisk As | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of obesity |
| CN1207038A (zh) | 1996-01-11 | 1999-02-03 | 诺沃挪第克公司 | 3,4－二苯基苯并二氢吡喃在生产预防或治疗绝经症状的药物组合物中的应用 |
| US5726202A (en) | 1996-01-11 | 1998-03-10 | Novo Nordisk A/S | Benign prostatic hypertrophy |
| US5883118A (en) | 1996-01-11 | 1999-03-16 | Nova Nordisk A/S | Prostatic carcinoma |
| HUP9902683A3 (en) | 1996-01-11 | 2001-08-28 | Novo Nordisk As | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of menopausal symptoms |
| US5747059A (en) | 1996-01-11 | 1998-05-05 | Novo Nordisk A/S | Atrophy of skin/mucous membrane |
| US5756539A (en) | 1996-07-11 | 1998-05-26 | Novo Nordis A/S | 3, 4-diphenyl chromans for inhibiting one or more psychiatric disorders |
| US5780502A (en) | 1996-07-12 | 1998-07-14 | Novo Nordisk A/S | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for inhibiting one or more symptoms of premenstrual syndrome |
| US5925771A (en) | 1996-10-28 | 1999-07-20 | Novo Nordisk A/S | Process for the preparation of (-)-3,4-trans-diarylchromans |
| US5919817A (en) | 1996-10-28 | 1999-07-06 | Novo Nordisk A/S | Cis-3, 4-chroman derivatives useful in the prevention or treatment of estrogen related diseases or syndromes |
| US6043269A (en) | 1996-10-28 | 2000-03-28 | Novo Nordisk A/S | cis-3,4-chroman derivatives useful in the prevention or treatment of estrogen related diseases or syndromes |
| ZA979642B (en) * | 1996-10-28 | 1998-04-28 | Novo Nordisk As | Heterocyclic compounds, compositions and uses. |
| AU4699897A (en) | 1996-10-28 | 1998-05-22 | Novo Nordisk A/S | Novel (-)-enantiomers of (cis)-3,4-chroman derivatives useful in the preve ntion or treatment of estrogen related diseases or syndromes |
| 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 |
| ZA98681B (en) | 1997-01-29 | 1998-07-29 | Novo Nordisk As | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for inhibition senescense-associated motor impairment |
| US6184005B1 (en) | 1998-04-28 | 2001-02-06 | Novo Nordisk A/S | Enzymatic resolvation for obtaining a (−)-3,4-trans-diarylchroman |
| ATE466850T1 (de) * | 1998-09-23 | 2010-05-15 | Res Dev Foundation | Tocopherole, tocotrienole, sonstige chroman- und seitenkettenderivate, sowie deren verwendungen |
| AU6315300A (en) | 1999-07-26 | 2001-02-13 | Shionogi & Co., Ltd. | Benzene derivatives and immunopotentiating compositions or drug-sensitivity restoring agents containing the same |
| WO2002030407A1 (en) | 2000-10-13 | 2002-04-18 | Astrazeneca Ab | ESTROGEN RECEPTOR-β LIGANDS |
| JP4256679B2 (ja) | 2001-03-16 | 2009-04-22 | ノボゲン リサーチ ピーティーワイ リミテッド | 再狭窄の治療方法 |
| US20050119301A1 (en) | 2001-03-16 | 2005-06-02 | Alan Husband | Treatment of restenosis |
| JP2005524630A (ja) | 2002-01-14 | 2005-08-18 | ノルディック・ビオサイエンス・エー／エス | エストロゲン受容体を介する軟骨破壊の抑制 |
| 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 |
| US20060167037A1 (en) * | 2003-11-19 | 2006-07-27 | Kelly Graham E | Combinational radiotherapy and chemotherapy compositions and methods |
| WO2006032085A1 (en) | 2004-09-21 | 2006-03-30 | Novogen Research Pty Ltd | Substituted chroman derivatives, medicaments and use in therapy |
| JP4976649B2 (ja) * | 2004-09-21 | 2012-07-18 | マーシャル エドワーズ，インク． | 化合物 |
| EP1809618B1 (en) * | 2004-09-21 | 2013-07-17 | Marshall Edwards, Inc. | Chroman derivatives, medicaments and use in therapy |
| US8080675B2 (en) | 2004-09-21 | 2011-12-20 | 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 |
| US7528267B2 (en) | 2005-08-01 | 2009-05-05 | Girindus America, Inc. | Method for enantioselective hydrogenation of chromenes |
| US20090221564A1 (en) | 2006-02-21 | 2009-09-03 | Trigen Limited | Heterocyclic Compounds and Their Use in the Treatment of Cardiovascular Disease |
| EP2084141A4 (en) | 2006-10-30 | 2010-07-21 | Novogen Res 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 |
| CN102215841A (zh) | 2008-08-29 | 2011-10-12 | 诺沃根研究控股有限公司 | 免疫调节活性 |
| AU2008230055A1 (en) | 2008-10-22 | 2010-05-06 | Novogen Research Pty Ltd | Methods for Inducing Programmed Cell Death |
| WO2010045674A1 (en) | 2008-10-22 | 2010-04-29 | Novogen Research Pty Ltd | Methods for inducing programmed cell death |
| EP2548017A2 (en) | 2010-03-15 | 2013-01-23 | 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 |
| US9708283B2 (en) * | 2010-11-01 | 2017-07-18 | Mei Pharma, Inc. | Isoflavonoid compositions 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 |
| CA2875964C (en) | 2012-06-07 | 2018-01-02 | 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 |
| 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 |
| CN103638008B (zh) | 2013-12-02 | 2015-09-16 | 刘艳娇 | Artoxanthochromane在治疗皮肤癌药物中的应用 |
| 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 |
| PT2953938T (pt) * | 2014-02-07 | 2017-10-09 | Novogen ltd | Compostos de benzopirano funcionais e sua utilização |
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