JP2012523458A - タンパク質ホスファターゼ２ａ活性化剤 - Google Patents
タンパク質ホスファターゼ２ａ活性化剤 Download PDFInfo
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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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
-
- 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
- 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
- A61K31/355—Tocopherols, e.g. vitamin E
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16875909P | 2009-04-13 | 2009-04-13 | |
| US61/168,759 | 2009-04-13 | ||
| PCT/US2010/030799 WO2010120711A1 (en) | 2009-04-13 | 2010-04-13 | Protein phosphatase 2a-activating agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012523458A true JP2012523458A (ja) | 2012-10-04 |
| JP2012523458A5 JP2012523458A5 (https=) | 2013-03-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012506102A Pending JP2012523458A (ja) | 2009-04-13 | 2010-04-13 | タンパク質ホスファターゼ２ａ活性化剤 |
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| Country | Link |
|---|---|
| US (1) | US8461362B2 (https=) |
| EP (1) | EP2419414A4 (https=) |
| JP (1) | JP2012523458A (https=) |
| AU (1) | AU2010236655A1 (https=) |
| CA (1) | CA2758823A1 (https=) |
| WO (1) | WO2010120711A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012524070A (ja) * | 2009-04-17 | 2012-10-11 | ザ オハイオ ステート ユニバーシティー リサーチ ファウンデーション | 抗接着剤 |
| JP2018508752A (ja) * | 2014-12-31 | 2018-03-29 | フリューダイム カナダ インコーポレイテッド | マスサイトメトリーによる分析用の構造化生体試料 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007143081A2 (en) | 2006-06-02 | 2007-12-13 | The Ohio State University Research Foundation | Therapeutic agents for the treatment of lymphoid malignancies |
| US8461362B2 (en) | 2009-04-13 | 2013-06-11 | The Ohio State University Research Foundation | Protein phosphatase 2A-activating agents |
| US8309768B2 (en) | 2010-11-29 | 2012-11-13 | The Ohio State University Research Foundation | FTY720-derived anticancer agents |
| WO2013181488A2 (en) * | 2012-06-01 | 2013-12-05 | The Ohio State University Research Foundation | Inhibition of leukemic stem cells by pp2a activating agents |
| EP3313819A1 (en) * | 2015-06-23 | 2018-05-02 | Case Western Reserve University | Compositions and methods for treating cancer |
| BR112018002550A2 (en) | 2015-08-10 | 2018-09-18 | Dana-Farber Cancer Institute, Inc. | inhibitor resistance mechanism |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002121132A (ja) * | 2000-08-09 | 2002-04-23 | Showa Denko Kk | 発がん抑制剤および発がん抑制方法 |
| JP2004504268A (ja) * | 2000-02-11 | 2004-02-12 | リサーチ ディベロップメント ファンデーション | トコフェロール、トコトリエノール、その他のクロマン、及びそれらの側鎖誘導体とその利用法 |
| JP2009538823A (ja) * | 2006-02-21 | 2009-11-12 | ザ オハイオ ステート ユニバーシティー リサーチ ファウンデーション | 抗癌剤 |
| JP2012524070A (ja) * | 2009-04-17 | 2012-10-11 | ザ オハイオ ステート ユニバーシティー リサーチ ファウンデーション | 抗接着剤 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2680749A (en) | 1951-12-01 | 1954-06-08 | Eastman Kodak Co | Water-soluble tocopherol derivatives |
| DE2822324C3 (de) | 1978-05-22 | 1981-02-26 | Basf Ag, 6700 Ludwigshafen | Herstellung von Vitamin-E-Trockenpulver |
| JPS59222415A (ja) | 1983-05-31 | 1984-12-14 | Kuraray Co Ltd | 免疫調節剤 |
| US4751224A (en) | 1983-07-21 | 1988-06-14 | Brown University Research Foundation | Treatment of metastasis |
| WO1997024112A1 (en) | 1995-12-28 | 1997-07-10 | Yoshitomi Pharmaceutical Industries, Ltd. | External preparation |
| US6476004B1 (en) | 1996-07-18 | 2002-11-05 | Mitsubishi Pharma Corporation | Pharmaceutical composition |
| JPH1180026A (ja) | 1997-09-02 | 1999-03-23 | Yoshitomi Pharmaceut Ind Ltd | 新規免疫抑制剤、その使用方法およびその同定方法 |
| DK1115398T3 (da) | 1998-09-23 | 2010-08-16 | Res Dev Foundation | Tocopheroler, tocotrienoler, andre chroman- og sidekædederivater og anvendelser deraf |
| US6703384B2 (en) | 1998-09-23 | 2004-03-09 | Research Development Foundation | Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof |
| US6770672B1 (en) | 1998-09-23 | 2004-08-03 | Research Development Foundation | Tocopherols, tocotrienols, other chroman and side chain derivatives and uses thereof |
| JP2004538304A (ja) | 2001-07-27 | 2004-12-24 | ユニバーシティー オブ ロチェスター | アンドロゲンレセプターのビタミンｅ阻害および前立腺癌細胞中の前立腺特異的抗原の発現 |
| US6858227B1 (en) | 2001-11-21 | 2005-02-22 | Sonus Pharmaceuticals, Inc. | Vitamin E conjugates |
| US20050215531A1 (en) | 2002-05-16 | 2005-09-29 | Thomas Baumruker | Use of edg receptor binding agents in cancer |
| AU2004271804B2 (en) | 2003-09-12 | 2011-01-06 | Newron Sweden Ab | Treatment of disorders of the nervous system |
| WO2005033093A1 (en) | 2003-09-19 | 2005-04-14 | Galileo Pharmaceuticals, Inc. | 7,8-bicycloalkyl-chroman derivatives |
| BRPI0619894B8 (pt) | 2005-12-15 | 2021-05-25 | Mitsubishi Tanabe Pharma Corp | composto de amina e composição farmacêutica |
| WO2007143081A2 (en) | 2006-06-02 | 2007-12-13 | The Ohio State University Research Foundation | Therapeutic agents for the treatment of lymphoid malignancies |
| HRP20121034T1 (hr) | 2006-08-17 | 2013-01-31 | University Of Chicago | Lijeäśenje upalnih bolesti |
| CA2663474C (en) * | 2006-09-15 | 2017-06-27 | Griffith University | Pro-oxidant anti-cancer compounds |
| JP4481316B2 (ja) * | 2007-01-09 | 2010-06-16 | 株式会社エヌ・ティ・ティ・ドコモ | ユーザ装置および送信方法 |
| JP5341754B2 (ja) | 2007-06-14 | 2013-11-13 | 田辺三菱製薬株式会社 | アミン化合物及びその医薬用途 |
| AU2009304596A1 (en) | 2008-10-17 | 2010-04-22 | Akaal Pharma Pty Ltd | S1P receptors modulators |
| US8461362B2 (en) | 2009-04-13 | 2013-06-11 | The Ohio State University Research Foundation | Protein phosphatase 2A-activating agents |
-
2010
- 2010-04-13 US US12/758,858 patent/US8461362B2/en not_active Expired - Fee Related
- 2010-04-13 JP JP2012506102A patent/JP2012523458A/ja active Pending
- 2010-04-13 EP EP10764981.6A patent/EP2419414A4/en not_active Withdrawn
- 2010-04-13 AU AU2010236655A patent/AU2010236655A1/en not_active Abandoned
- 2010-04-13 CA CA2758823A patent/CA2758823A1/en not_active Abandoned
- 2010-04-13 WO PCT/US2010/030799 patent/WO2010120711A1/en not_active Ceased
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004504268A (ja) * | 2000-02-11 | 2004-02-12 | リサーチ ディベロップメント ファンデーション | トコフェロール、トコトリエノール、その他のクロマン、及びそれらの側鎖誘導体とその利用法 |
| JP2002121132A (ja) * | 2000-08-09 | 2002-04-23 | Showa Denko Kk | 発がん抑制剤および発がん抑制方法 |
| JP2009538823A (ja) * | 2006-02-21 | 2009-11-12 | ザ オハイオ ステート ユニバーシティー リサーチ ファウンデーション | 抗癌剤 |
| JP2012524070A (ja) * | 2009-04-17 | 2012-10-11 | ザ オハイオ ステート ユニバーシティー リサーチ ファウンデーション | 抗接着剤 |
Non-Patent Citations (4)
| Title |
|---|
| JPN6014025157; Ｃｈｕｎｇ-Ｗａｉ Ｓｈｉａｕ， Ｊｕｉ-Ｗｅｎ Ｈｕａｎｇ， Ｄａ-Ｓｈｅｎｇ Ｗａｎｇ， Ｊｉｎｇ-Ｒｕ Ｗｅｎｇ， Ｃｈｉｈ-Ｃｈｅｎｇ Ｙａｎｇ， Ｃｈｉａ-Ｈｕｉ Ｌｉｎ， Ｃｈｅｎｇｌｏｎ: 'alpha-Ｔｏｃｏｐｈｅｒｙｌ Ｓｕｃｃｉｎａｔｅ Ｉｎｄｕｃｅｓ Ａｐｏｐｔｏｓｉｓ ｉｎ Ｐｒｏｓｔａｔｅ Ｃａｎｃｅｒ Ｃｅｌｌｓ ｉｎ Ｐａｒｔ ｔｈｒｏｕｇｈ Ｉｎｈｉｂｉｔｉｏｎ ｏｆ Ｂｃｌ' Ｔｈｅ Ｊｏｕｒｎａｌ ｏｆ Ｂｉｏｌｏｇｉｃａｌ Ｃｈｅｍｉｓｔｒｙ ｖｏｌ．２８１， Ｎｏ．１７, 20060428, ｐ&#x * |
| JPN6014025158; Ｐａｕｌ Ｌ． Ｃｒｉｓｐｅｎ， Ｒｏｂｅｒｔ Ｇ． Ｕｚｚｏ， Ｋｏｎｓｔａｎｔｉｎ Ｇｏｌｏｖｉｎｅ， Ｐｅｔｅｒ Ｍａｋｈｏｖ， Ａｌａｎ Ｐｏｌｌａｃｋ， Ｅｒｉｃ Ｍ． Ｈｏｒｗｉｔｚ， Ｒ: 'Ｖｉｔａｍｉｎ Ｅ Ｓｕｃｃｉｎａｔｅ Ｉｎｈｉｂｉｔｓ ＮＦ-ｋＢ ａｎｄ Ｐｒｅｖｅｎｔｓ ｔｈｅ Ｄｅｖｅｌｏｐｍｅｎｔ ｏｆ ａ Ｍｅｔａｓｔａｔｉｃ Ｐｈｅｎｏｔｙｐｅ ｉｎ Ｐｒｏｓｔａｔ' Ｔｈｅ Ｐｒｏｓｔａｔｅ ｖｏｌ．６７， Ｎｏ．６, 20070501, ｐ．５８２-５９０, Ｊｏｈｎ Ｗｉｌｅｙ ＆ Ｓｏ&#x * |
| JPN6014025159; Ｊｉｒｉ Ｎｅｕｚｉｌ， Ｔｏｂｉａｓ Ｗｅｂｅｒ， Ａｎｄｒｅａｓ Ｓｃｈｒｏｄｅｒ， Ｍｉｎ Ｌｕ， Ｇｅｏｒｇ Ｏｓｔｅｒｍａｎｎ， Ｎｉｎａ Ｇｅｌｌｅｒｔ， Ｇｅｏｒｇｅ Ｃ． Ｍａｙｎｅ，: 'Ｉｎｄｕｃｔｉｏｎ ｏｆ ｃａｎｃｅｒ ｃｅｌｌ ａｐｏｐｔｏｓｉｓ ｂｙ alpha-ｔｏｃｏｐｈｅｒｙｌ ｓｕｃｃｉｎａｔｅ： ｍｏｌｅｃｕｌａｒ ｐａｔｈｗａｙｓ ａｎｄ ｓｔｒｕｃｔｕｒａｌ ｒｅｑ' Ｔｈｅ ＦＡＳＥＢ Ｊｏｕｒｎａｌ ｖｏｌ．１５， Ｎｏ．２, 20010201, ｐ．４０３-４１５, Ｔｈｅ Ｆｅｄｅｒａｔ * |
| JPN6014025160; Ｐｏ-Ｈｓｉｅｎ Ｈｕａｎｇ， Ｄａｓｈｅｎｇ Ｗａｎｇ， Ｈｓｉａｏ-Ｃｈｉｎｇ Ｃｈｕａｎｇ， Ｓｈｕｏ Ｗｅｉ， Ｓａｍｕｅｌ Ｋ．Ｋｕｌｐ， Ｃｈｉｎｇ-Ｓｈｉｈ Ｃｈｅｎ: 'alpha-Ｔｏｃｏｐｈｅｒｙｌ Ｓｕｃｃｉｎａｔｅ ａｎｄ ｄｅｒｉｖａｔｉｖｅｓ ｍｅｄｉａｔｅ ｔｈｅ ｔｒａｎｓｃｒｉｐｔｉｏｎａｌ ｒｅｐｒｅｓｓｉｏｎ ｏｆ ａｎｄｒｏｇｅｎ ｒｅｃｅｐｔｏｒ' Ｃａｒｃｉｎｏｇｅｎｅｓｉｓ ｖｏｌ．３０， Ｎｏ．７, 200907, ｐ．１１２５-１１３１, Ｏｘｆｏｒｄ Ｕｎｉｖｅｒｓｉｔｙ Ｐｒｅｓｓ * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012524070A (ja) * | 2009-04-17 | 2012-10-11 | ザ オハイオ ステート ユニバーシティー リサーチ ファウンデーション | 抗接着剤 |
| JP2018508752A (ja) * | 2014-12-31 | 2018-03-29 | フリューダイム カナダ インコーポレイテッド | マスサイトメトリーによる分析用の構造化生体試料 |
| US10847357B2 (en) | 2014-12-31 | 2020-11-24 | Fluidigm Canada Inc. | Structured biological samples for analysis by mass cytometry |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010120711A1 (en) | 2010-10-21 |
| US20100267673A1 (en) | 2010-10-21 |
| US8461362B2 (en) | 2013-06-11 |
| EP2419414A1 (en) | 2012-02-22 |
| AU2010236655A1 (en) | 2011-11-17 |
| CA2758823A1 (en) | 2010-10-21 |
| EP2419414A4 (en) | 2013-12-04 |
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