ES2727387T3 - Sal de lisina de ácido 15-hidroxi-8(Z),11(Z),13(E)-eicosatrienoico - Google Patents
Sal de lisina de ácido 15-hidroxi-8(Z),11(Z),13(E)-eicosatrienoico Download PDFInfo
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- ES2727387T3 ES2727387T3 ES14843234T ES14843234T ES2727387T3 ES 2727387 T3 ES2727387 T3 ES 2727387T3 ES 14843234 T ES14843234 T ES 14843234T ES 14843234 T ES14843234 T ES 14843234T ES 2727387 T3 ES2727387 T3 ES 2727387T3
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- lysine
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/04—Preparation of hydrazides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361904600P | 2013-11-15 | 2013-11-15 | |
| PCT/IB2014/003027 WO2015071766A1 (en) | 2013-11-15 | 2014-11-17 | Pharmaceutically acceptable salts of polyunsaturated hydroxy fatty acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2727387T3 true ES2727387T3 (es) | 2019-10-15 |
Family
ID=52669635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14843234T Active ES2727387T3 (es) | 2013-11-15 | 2014-11-17 | Sal de lisina de ácido 15-hidroxi-8(Z),11(Z),13(E)-eicosatrienoico |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US10017453B2 (enExample) |
| EP (3) | EP3068757B1 (enExample) |
| JP (3) | JP2016538288A (enExample) |
| CN (2) | CN105899485B (enExample) |
| ES (1) | ES2727387T3 (enExample) |
| WO (1) | WO2015071766A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113230244A (zh) | 2015-12-18 | 2021-08-10 | 艾菲穆恩有限公司 | 包含15-hepe的组合物及其使用方法 |
| EP4364572A3 (en) * | 2017-03-14 | 2024-07-10 | Ibiden Co., Ltd. | Plant activator |
| US20210315851A1 (en) | 2020-04-03 | 2021-10-14 | Afimmune Limited | Compositions comprising 15-hepe and methods of treating or preventing hematologic disorders, and/or related diseases |
| WO2022090482A1 (en) | 2020-10-30 | 2022-05-05 | Ds Biopharma Limited | Pharmaceutical compositions comprising 15-hetre and methods of use thereof |
| FR3148365A1 (fr) * | 2023-05-04 | 2024-11-08 | Pierre Fabre Dermo-Cosmetique | Oxylipines dans le traitement de la séborrhée et/ou de l’acné |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055923A (en) * | 1960-03-25 | 1962-09-25 | Baxter Laboratories Inc | Fatty acid salts |
| IE47777B1 (en) | 1978-01-23 | 1984-06-13 | Efamol Ltd | Pharmaceutical and dietary composition comprising gamma-linolenic acids |
| JPH04507397A (ja) | 1988-01-14 | 1992-12-24 | フリッツ，アンデルス | 湿疹治療用薬剤製造における必須脂肪酸の使用法 |
| GB9111900D0 (en) | 1991-06-03 | 1991-07-24 | Efamol Holdings | Fatty acid compositions |
| JPH05186342A (ja) | 1992-01-10 | 1993-07-27 | Fujirebio Inc | 免疫調節作用を併せもつ抗炎症剤 |
| US5807884A (en) * | 1992-10-30 | 1998-09-15 | Emory University | Treatment for atherosclerosis and other cardiovascular and inflammatory diseases |
| GB9301446D0 (en) | 1993-01-26 | 1993-03-17 | Scotia Holdings Plc | Internal radiation damage |
| AU683027B2 (en) | 1993-01-27 | 1997-10-30 | Scotia Holdings Plc | Triglycerides |
| US5696166A (en) * | 1995-10-31 | 1997-12-09 | Yanni; John M. | Compositions containing hydroxyeicosatetraenoic acid derivatives and methods of use in treating dry eye disorders |
| JP2000500879A (ja) * | 1996-09-20 | 2000-01-25 | アセロジエニクス・インコーポレイテツド | 炎症性疾患の診断及びメディエータ |
| GB9715444D0 (en) | 1997-07-22 | 1997-09-24 | Scotia Holdings Plc | Therapeutic and dietary compositions |
| CA2332272A1 (en) * | 1998-05-15 | 1999-11-25 | University Of Vermont | Novel analogs of 16-hydroxyeicosatetraenoic acid |
| JP2000191525A (ja) | 1998-12-25 | 2000-07-11 | Nof Corp | 皮膚外用剤組成物 |
| TR200201250T2 (tr) * | 1999-11-09 | 2002-09-23 | Alcon, Inc | Hidroksieikosatetraenoat tuzları, bileşimleri ve bunların göz kuruması bozukluklarının iyileştirilmesinde kullanım yöntemleri. |
| IL151299A0 (en) | 2000-02-16 | 2003-04-10 | Brigham & Womens Hospital | Aspirin-triggered lipid mediators |
| US20020188024A1 (en) | 2000-08-23 | 2002-12-12 | Chilton Floyd H. | Fatty acid-containing emulsion with increased bioavailability |
| DE10121252A1 (de) | 2001-04-30 | 2002-11-07 | Christos C Zouboulis | Behandlung der Akne |
| WO2004072013A1 (ja) * | 2003-02-14 | 2004-08-26 | Taisho Pharmaceutical Co.,Ltd. | ヒドロキシエイコサジエン酸化合物 |
| JP2005179211A (ja) | 2003-12-17 | 2005-07-07 | Idemitsu Kosan Co Ltd | 皮膚外用剤組成物 |
| WO2005063231A2 (en) | 2003-12-31 | 2005-07-14 | Igennus Limited | Formulation containing an eicosapentaenoic acid or an ester thereof and a triterpene or esther thereof |
| US20050239889A1 (en) | 2004-04-26 | 2005-10-27 | Jean Gosselin | In vivo release of endogenous anti-microbial mediators by leukotriene B4 (LTB4) administration |
| US7666447B2 (en) | 2004-10-08 | 2010-02-23 | Pharmanutrients | Compositions including Krill extracts and conjugated linoleic acid and methods of using same |
| US7893106B2 (en) | 2004-11-19 | 2011-02-22 | Martek Biosciences, Corporation | Oxylipins from stearidonic acid and γ-linolenic acid and methods of making and using the same |
| EP1852114B1 (en) | 2005-02-14 | 2019-09-18 | Suntory Holdings Limited | Composition containing dihomo-y-linolenic acid (dgla) as active ingredient |
| TW200711649A (en) | 2005-06-17 | 2007-04-01 | Combinatorx Inc | Combination therapy for the treatment of immunoinflammatory disorders |
| EP3285072B1 (en) | 2006-08-08 | 2020-04-15 | Metabolon, Inc. | Markers of non-alcoholic fatty liver disease (nafld) and non-alcoholic steatohepatitis (nash) and methods of use thereof |
| JP5101894B2 (ja) | 2007-01-15 | 2012-12-19 | サントリーホールディングス株式会社 | 高度不飽和脂肪酸及びこれを含有する脂質の製造方法 |
| GB0802116D0 (en) | 2008-02-05 | 2008-03-12 | Natural Enviromental Res Counc | Treatment |
| JPWO2009154230A1 (ja) | 2008-06-17 | 2011-12-01 | 持田製薬株式会社 | 非アルコール性脂肪肝炎の予防／改善・治療薬 |
| GB0907413D0 (en) | 2009-04-29 | 2009-06-10 | Equateq Ltd | Novel methods |
| GB0907601D0 (en) | 2009-05-01 | 2009-06-10 | Equateq Ltd | Novel methods |
| WO2012135032A2 (en) | 2011-03-25 | 2012-10-04 | The Brigham And Women's Hospital, Inc. | Anti-inflammatory particles |
| US20120264824A1 (en) | 2011-04-15 | 2012-10-18 | Mochida Pharmaceutical Co., Ltd. | Compositions and methods for treating non-alcoholic steatohepatitis |
| MX2014004710A (es) | 2011-10-19 | 2014-12-10 | Dignity Sciences Ltd | Composiciones farmaceuticas que comprenden dgla y/o 15-hetre y metodos para usar los mismos. |
| US8293790B2 (en) | 2011-10-19 | 2012-10-23 | Dignity Sciences Limited | Pharmaceutical compositions comprising DGLA and benzoyl peroxide and methods of use thereof |
| BR112014013098A2 (pt) | 2011-11-29 | 2017-06-13 | Dignity Sciences Ltd | composições compreendendo ácidos graxos que têm 20 carbonos e métodos de produção e uso dos mesmos |
| SG11201403805WA (en) | 2012-01-06 | 2014-08-28 | Omthera Pharmaceuticals Inc | Dpa-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form |
| US20120264705A1 (en) | 2012-01-26 | 2012-10-18 | Dignity Sciences Limited | Antimicrobial compositions comprising 15-hetre and methods of use thereof |
| US20130267598A1 (en) | 2012-02-23 | 2013-10-10 | Dignity Sciences Limited | Pharmaceutical compositions comprising dgla, 15-ohepa, and/or 15-hetre and methods of reducing sebum production using same |
| WO2013150386A2 (en) | 2012-04-04 | 2013-10-10 | Pronova Biopharma Norge As | Compositions comprising omega-3 fatty acids and vitamin d for acne vulgaris and/or eczema, and methods and uses thereof |
| CN110478342A (zh) | 2012-05-10 | 2019-11-22 | 索卢泰克斯Na有限责任公司 | 含有天然专门促消退介质及其前体的具有抗炎活性的油 |
| WO2014022816A2 (en) | 2012-08-03 | 2014-02-06 | Dignity Sciences Limited | Pharmaceutical compositions comprising 15-hetre and methods of treating or preventing arthritis using same |
| GB201301626D0 (en) | 2013-01-30 | 2013-03-13 | Dignity Sciences Ltd | Composition comprising 15-OHEPA and methods of using the same |
| MX2016008953A (es) | 2014-01-10 | 2017-02-02 | Dignity Sciences Ltd | Composiciones farmaceuticas que comprenden i5-hidroxi-eicosa- 5,8,11,13,17-pentaenoico ( 15-hepe ) y metodos para tratar el asma y trastornos pulmonares que usan las mismas. |
| WO2015185698A1 (en) | 2014-06-04 | 2015-12-10 | Dignity Sciences Limited | Pharmaceutical compositions comprising dgla and use of same |
| MA41120A (fr) | 2014-12-02 | 2017-10-10 | Afimmune Ltd | Compositions comprenant le 15-hepe et méthodes de traitement ou de prévention de la fibrose à l'aide de celles-ci |
| CN113230244A (zh) | 2015-12-18 | 2021-08-10 | 艾菲穆恩有限公司 | 包含15-hepe的组合物及其使用方法 |
| US20170196825A1 (en) | 2016-01-07 | 2017-07-13 | Dignity Sciences Limited | Pharmaceutical compositions comprising dgla and use of same |
-
2014
- 2014-11-17 EP EP14843234.7A patent/EP3068757B1/en active Active
- 2014-11-17 CN CN201480071412.2A patent/CN105899485B/zh not_active Expired - Fee Related
- 2014-11-17 EP EP19157319.5A patent/EP3546446A1/en not_active Withdrawn
- 2014-11-17 WO PCT/IB2014/003027 patent/WO2015071766A1/en not_active Ceased
- 2014-11-17 CN CN201811061377.2A patent/CN109232278A/zh active Pending
- 2014-11-17 JP JP2016530882A patent/JP2016538288A/ja active Pending
- 2014-11-17 EP EP21159762.0A patent/EP3878835A1/en not_active Withdrawn
- 2014-11-17 ES ES14843234T patent/ES2727387T3/es active Active
- 2014-11-17 US US14/543,638 patent/US10017453B2/en active Active
-
2017
- 2017-12-01 US US15/828,700 patent/US10544088B2/en not_active Expired - Fee Related
-
2019
- 2019-11-26 JP JP2019212877A patent/JP6818851B2/ja not_active Expired - Fee Related
- 2019-12-05 US US16/704,289 patent/US20200181064A1/en not_active Abandoned
-
2020
- 2020-12-28 JP JP2020218615A patent/JP2021073194A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP3878835A1 (en) | 2021-09-15 |
| US20200181064A1 (en) | 2020-06-11 |
| US10017453B2 (en) | 2018-07-10 |
| CN105899485B (zh) | 2018-10-19 |
| JP6818851B2 (ja) | 2021-01-20 |
| JP2021073194A (ja) | 2021-05-13 |
| US10544088B2 (en) | 2020-01-28 |
| CN105899485A (zh) | 2016-08-24 |
| EP3068757A1 (en) | 2016-09-21 |
| US20150152034A1 (en) | 2015-06-04 |
| JP2016538288A (ja) | 2016-12-08 |
| JP2020055825A (ja) | 2020-04-09 |
| CN109232278A (zh) | 2019-01-18 |
| US20180118655A1 (en) | 2018-05-03 |
| EP3546446A1 (en) | 2019-10-02 |
| WO2015071766A1 (en) | 2015-05-21 |
| EP3068757B1 (en) | 2019-02-27 |
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