PT1853254E - Moduladores de citoquina utilizando glicéridos cíclicos de ácidos gordos poliinsaturados essenciais - Google Patents
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| TR201808471T4 (tr) | 2010-07-05 | 2018-07-23 | Beth Israel Deaconess Medical Ct Inc | Sn-2-monoaçilgliseroller ve lipid malabsorpsiyonu. |
Family Cites Families (130)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2077371A (en) | 1937-04-13 | Synthetic drx | ||
| US2617791A (en) | 1949-09-15 | 1952-11-11 | Trojan Powder Co | Recovery of valuable products from pentaerythritol mother liquor |
| US3082228A (en) | 1959-12-18 | 1963-03-19 | Escambia Chem Corp | Method for producing monoesters of polyunsaturated fatty acids |
| US3158541A (en) | 1959-12-18 | 1964-11-24 | Escambia Chem Corp | Product for reduction of blood cholesterol concentration |
| FR2003425A1 (fr) | 1968-03-07 | 1969-11-07 | Unilever Nv | Compositions grasses plastiques comestibles et procede pour les preparer |
| US3558656A (en) | 1968-04-19 | 1971-01-26 | Smith Kline French Lab | Glycerol trichloroethyl carbonate and derivatives |
| US3671563A (en) | 1968-04-19 | 1972-06-20 | Smith Kline French Lab | Glycerol 3-(2,2,2-trichloroethyl) carbonate |
| US3676472A (en) | 1969-07-28 | 1972-07-11 | American Home Prod | Certain linoleic and linolenic acid ester fractions of vegetable oils and derivatives thereof |
| US3748348A (en) | 1970-07-27 | 1973-07-24 | Lever Brothers Ltd | Directed-interesterified glyceridic oils having a high linoleic acid content and process for their production |
| US3671557A (en) | 1970-09-17 | 1972-06-20 | Smith Kline French Lab | 1,2-diacylglycerol 3-(2,2,2-trichloroethyl) carbonates |
| GB1370021A (en) | 1971-03-25 | 1974-10-09 | Unilever Ltd | Process for preparing usaturated carboxylic acids |
| US3855254A (en) | 1972-03-31 | 1974-12-17 | Lever Brothers Ltd | Interesterification process |
| GB1506563A (en) | 1974-04-25 | 1978-04-05 | Williams J | Immunosuppressive agents |
| US4058594A (en) | 1974-04-25 | 1977-11-15 | John Williams | Immuno-suppressive agents |
| US3988446A (en) | 1974-11-07 | 1976-10-26 | Abbott Laboratories | Glycerides with anti-inflammatory properties |
| US3972907A (en) | 1975-03-24 | 1976-08-03 | G. D. Searle & Co. | Anti-hyperlipidemic fatty acids and esters |
| US4048202A (en) | 1975-04-11 | 1977-09-13 | G. D. Searle & Co. | 3-O-Alkanoylglyceric acids |
| US4181670A (en) | 1978-12-11 | 1980-01-01 | G. D. Searle & Co. | Phenyl 5Z,8Z,11Z,14Z-eicosatetraenoate and congeners |
| DE3368377D1 (en) | 1982-04-16 | 1987-01-29 | Nestle Sa | Lipid composition for oral, enteral or parenteral feeding |
| US4701469A (en) | 1983-04-15 | 1987-10-20 | Roussel Uclaf | Triglycerides, process for therapeutical applications and compositions containing them |
| US4701468A (en) | 1983-04-15 | 1987-10-20 | Roussel-Uclaf | Oxidized triglycerides having therapeutic utility |
| US4607052A (en) | 1983-04-15 | 1986-08-19 | Roussel-Uclaf | Triglycerides, dietetic and therapeutical applications and compositions containing them |
| GB8404463D0 (en) | 1984-02-21 | 1984-03-28 | Efamol Ltd | Microbiological production of essential fatty acids |
| AT383130B (de) | 1984-05-15 | 1987-05-25 | Chemie Linz Ag | Verfahren zur herstellung von an c1 und c2 verschieden substituierten phosphatidylcholinen und phosphatidylethanolaminen ueber die neuen verbindungen 1-0-tritylglycerophosphocholin beziehungsweise (1-0,n-ditrityl)-glycerophosphoethanolamin |
| US5077312A (en) | 1984-07-08 | 1991-12-31 | Oncogen | Biologically active lipids binding membrane receptors |
| GB2178752B (en) | 1985-07-12 | 1989-10-11 | Unilever Plc | Substitute milk fat |
| GB8524275D0 (en) | 1985-10-02 | 1985-11-06 | Efamol Ltd | Pharmaceutical & dietary compositions |
| US5151291A (en) | 1985-12-27 | 1992-09-29 | Nisshin Flour Milling Co., Ltd. | Glycerides of eicosapentaenoic acid, processes for preparing the same and oil and fat products containing the same |
| US5306730A (en) | 1986-02-03 | 1994-04-26 | Kabushiki Kaisha Yakult Honsha | Botulinum toxin neutralizer |
| US5227403A (en) | 1986-10-01 | 1993-07-13 | The Nisshin Oil Mills, Ltd. | Fats and oils having superior digestibility and absorptivity |
| US4867965A (en) | 1986-10-02 | 1989-09-19 | Revlon, Inc. | Fatty acid diesters |
| US4832975A (en) | 1987-09-29 | 1989-05-23 | The Procter & Gamble Company | Tailored triglycerides having improved autoignition characteristics |
| US5008126A (en) | 1989-06-27 | 1991-04-16 | Nabisco Brands, Inc. | Long chain diol diesters as low calorie fat mimetics |
| GB9026648D0 (en) | 1990-12-07 | 1991-01-23 | Efamol Holdings | Nutrition |
| US5922345A (en) | 1990-12-07 | 1999-07-13 | Scotia Holdings Plc | Nutrition |
| PH11992043811B1 (en) | 1991-01-24 | 2002-08-22 | Martek Corp | Arachidonic acid and methods for the production and use thereof |
| US5658767A (en) | 1991-01-24 | 1997-08-19 | Martek Corporation | Arachidonic acid and methods for the production and use thereof |
| US5674901A (en) | 1995-06-01 | 1997-10-07 | Wisconsin Alumni Research Foundation | Methods of treating animals to maintain or increase CD-4 and CD-8 cell populations |
| US5618955A (en) | 1992-11-30 | 1997-04-08 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Fatty acid derivatives and pharmaceutical compositions containing same |
| ES2136189T3 (es) | 1993-01-15 | 1999-11-16 | Abbott Lab | Lipidos estructurados. |
| GB9301446D0 (en) | 1993-01-26 | 1993-03-17 | Scotia Holdings Plc | Internal radiation damage |
| JPH06279311A (ja) | 1993-03-26 | 1994-10-04 | Sagami Chem Res Center | プロテインキナーゼcアイソザイムの活性化剤 |
| JPH0741421A (ja) | 1993-05-28 | 1995-02-10 | Suntory Ltd | ロイコトリエンb4 (ltb4 )による医学的症状の予防及び改善剤 |
| US20050027004A1 (en) | 1993-06-09 | 2005-02-03 | Martek Biosciences Corporation | Methods of treating senile dementia and Alzheimer's diseases using docosahexaenoic acid and arachidonic acid compositions |
| US5663450A (en) | 1993-08-17 | 1997-09-02 | Cv Therapeutics | Macrophage lipid chemoattractant |
| US5668174A (en) | 1993-12-29 | 1997-09-16 | Kowa Tekuno Sachi Co., Ltd. | Method of treating hyperparathyroidism |
| JPH07309773A (ja) | 1994-05-16 | 1995-11-28 | Sagami Chem Res Center | アセチルコリン放出促進剤 |
| FR2722410B1 (fr) | 1994-07-15 | 1996-10-04 | Grinda Jean Robert | Procede de stabilisation des acides gras poly-insatures et utilisation de ces produits stabilises entherapeutique |
| JP3770628B2 (ja) | 1994-08-09 | 2006-04-26 | サントリー株式会社 | 遅延型アレルギー反応を介する医学的症状の予防及び改善剤 |
| EP0707850A1 (en) | 1994-09-21 | 1996-04-24 | Scotia Holdings Plc | Use of polyunsaturated fatty acids for the manufacture of a medicament for the treatment of brest pain |
| EP0711503A3 (en) | 1994-11-14 | 1997-11-26 | Scotia Holdings Plc | Milk fortified with GLA and/or DGLA |
| US5990163A (en) | 1995-01-13 | 1999-11-23 | The Salk Institute For Biological Studies | Selective modulation of processes mediated by retinoid X receptors, and compounds useful therefor |
| DE19503993A1 (de) | 1995-02-08 | 1996-08-14 | Johann Friedrich Dr Med Desaga | Verwendung eines Produktes zur enteralen Versorgung mit Lebensmittelinhaltsstoffen oder Arzneimittelinhaltsstoffen |
| US6410078B1 (en) | 1995-04-28 | 2002-06-25 | Loders-Croklaan B.V. | Triglycerides, rich in polyunsaturated fatty acids |
| ES2232839T3 (es) | 1995-08-07 | 2005-06-01 | Suntory Limited | Uso de una composicion para prevenir o tratar enfermedades causadas por anormalidades en tejidos cartilaginosos. |
| GB9519661D0 (en) | 1995-09-27 | 1995-11-29 | Scotia Holdings Plc | Fatty acid treatment |
| US6015798A (en) | 1995-10-10 | 2000-01-18 | Colgate Palmolive Company | Method for reducing the damaging effects of radiation therapy on animal skin and mucosa |
| US5776913A (en) | 1995-10-10 | 1998-07-07 | Colgate Palmolive Company | Therapeutic diet for metabolic abnormalities found in animals with lymphoma |
| JP2000508645A (ja) | 1996-04-12 | 2000-07-11 | ペプテック リミテッド | ポリ不飽和脂肪酸を使用する免疫病の治療方法 |
| US5753702A (en) | 1996-05-22 | 1998-05-19 | University Of Vermont | Arachidonic acid metabolite, 16-hete |
| ES2203806T3 (es) | 1996-06-03 | 2004-04-16 | Croda International Plc | Compuestos y usos de los mismos. |
| US6340485B1 (en) | 1996-06-03 | 2002-01-22 | Croda International Plc | Compositions and uses thereof |
| WO1998000125A1 (en) | 1996-06-29 | 1998-01-08 | The Scottish Agricultural College | Improvement of male fertility with antioxidants and/or polyunsaturated fatty acids |
| GB9617847D0 (en) | 1996-08-27 | 1996-10-09 | Scotia Holdings Plc | Fatty acid treatment |
| PL190181B1 (pl) | 1996-10-11 | 2005-11-30 | Scarista Ltd | Zastosowanie oleju zawierającego kwas eikozapentaenowy (KEP) i/lub kwas stearydonowy (KS) oraz preparat farmaceutyczny zawierający olej |
| SK112399A3 (en) | 1997-02-21 | 2000-12-11 | Abbott Lab | Methods and compositions for reducing the incidence of necrotizing enterocolitis |
| US6080787A (en) | 1997-02-21 | 2000-06-27 | Abbott Laboratories | Methods for reducing the incidence of necrotizing enterocolitis |
| US6201022B1 (en) | 1997-03-27 | 2001-03-13 | Myorx, Inc. | Methods for treating neurotransmitter-mediated pain syndromes by topically administering an omega fatty acid |
| US6432684B1 (en) | 1997-04-11 | 2002-08-13 | Abbott Laboratories | Human desaturase gene and uses thereof |
| US6051754A (en) | 1997-04-11 | 2000-04-18 | Abbott Laboratories | Methods and compositions for synthesis of long chain poly-unsaturated fatty acids in plants |
| US5968809A (en) | 1997-04-11 | 1999-10-19 | Abbot Laboratories | Methods and compositions for synthesis of long chain poly-unsaturated fatty acids |
| US20020037876A1 (en) | 1998-06-25 | 2002-03-28 | Yissum Research Development Company Of Hebrew University Of Jerusalem | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
| FR2765482B1 (fr) | 1997-07-07 | 2000-12-08 | Oreal | Utilisation de l'acide y-linolenique pour prevenir le stress oxydatif |
| GB9715444D0 (en) | 1997-07-22 | 1997-09-24 | Scotia Holdings Plc | Therapeutic and dietary compositions |
| EP0919230A1 (en) | 1997-12-01 | 1999-06-02 | Societe Des Produits Nestle S.A. | NMIFA's as anti-inflammatory agents in superficial mammal tissues |
| US6369252B1 (en) | 1998-02-26 | 2002-04-09 | The University Of Georgia Research Foundation, Inc. | Structured lipids |
| IL138690A0 (en) | 1998-04-03 | 2001-10-31 | Yissum Res Dev Co | Synthetic endogenous cannabinoids, analogues and uses thereof |
| US6696584B2 (en) | 1998-05-04 | 2004-02-24 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
| US6214372B1 (en) | 1998-05-04 | 2001-04-10 | Con Lin Co., Inc. | Method of using isomer enriched conjugated linoleic acid compositions |
| US7101914B2 (en) | 1998-05-04 | 2006-09-05 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
| US7589220B2 (en) * | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| WO1999064389A1 (en) | 1998-06-09 | 1999-12-16 | Alexandros Makriyannis | Inhibitors of the anandamide transporter as analgesic agents |
| ATE375712T1 (de) | 1998-08-04 | 2007-11-15 | Cargill Inc | Promotoren der fettsäure-desaturase aus pflanzen |
| KR100325581B1 (ko) | 1998-08-07 | 2002-08-24 | 오우택 | 아라키토닉산의리폭시게네이즈대사결과물질을함유하는진통제용조성물 |
| AU5561999A (en) | 1998-08-13 | 2000-03-06 | Wistar Institute, The | Methods for reducing atherosclerotic plaques |
| GB9901809D0 (en) | 1999-01-27 | 1999-03-17 | Scarista Limited | Highly purified ethgyl epa and other epa derivatives for psychiatric and neurological disorderes |
| DE10029562A1 (de) | 1999-06-24 | 2001-03-01 | Strathmann Ag & Co | Lipophile Brennesselextrakte, Verfahren zu deren Herstellung und ihre Verwendung |
| DE19930030B4 (de) | 1999-06-30 | 2004-02-19 | Meduna Arzneimittel Gmbh | CO-3-ungesättigte Fettsäuren enthaltende orale Darreichungsform |
| FR2797584B1 (fr) | 1999-08-16 | 2008-07-25 | Stephane Desjonqueres | Utilisation de lipides peroxydes dans le traitement ou la prevention des plaies et inflammations des muqueuses de la cavite buccale |
| JP3779505B2 (ja) | 1999-08-24 | 2006-05-31 | 花王株式会社 | 油脂組成物 |
| US6426367B1 (en) | 1999-09-09 | 2002-07-30 | Efa Sciences Llc | Methods for selectively occluding blood supplies to neoplasias |
| US6340705B1 (en) | 1999-09-10 | 2002-01-22 | Monsanto Technology, Llc | Use of α-linolenic acid metabolites for treatment or prevention of cancer |
| EP1088552B1 (en) | 1999-09-30 | 2006-04-19 | Loders Croklaan B.V. | Compositions containing pinolenic acid and its use a health component |
| GB9923738D0 (en) | 1999-10-07 | 1999-12-08 | Nestle Sa | Nutritional composition |
| US20010047036A1 (en) | 1999-12-17 | 2001-11-29 | Vanderhoof Jon A. | Composition for improving the proliferative response during adaptation of the gastrointestinal tract and use in short bowel syndrome |
| EG22407A (en) | 2000-02-17 | 2003-01-29 | Iams Company | Method for improving bone modeling and chondrocyte functioning in growing canines |
| US6361806B1 (en) | 2000-02-23 | 2002-03-26 | Michael P. Allen | Composition for and method of topical administration to effect changes in subcutaneous adipose tissue |
| EP1129711B1 (en) | 2000-02-24 | 2004-01-28 | Unilever N.V. | Pinolenic acid against diabetes |
| ATE277608T1 (de) * | 2000-06-23 | 2004-10-15 | Yissum Res Dev Co | 2-arachidonylglycerol, ein hemmer des tumor nekrose faktors -alfa und neuroprotektor des gehirns bei geschlossenen kopfverletzungen |
| GB0016045D0 (en) | 2000-06-29 | 2000-08-23 | Laxdale Limited | Therapeutic combinations of fatty acids |
| JP2002047176A (ja) | 2000-08-04 | 2002-02-12 | Idemitsu Technofine Co Ltd | IgE産生抑制剤 |
| US6664230B1 (en) | 2000-08-24 | 2003-12-16 | The Regents Of The University Of California | Orally administered peptides to ameliorate atherosclerosis |
| FR2815227B1 (fr) | 2000-10-17 | 2003-04-11 | Schwartz Laboratoires Robert | Composition anti-stress destinee a etre incorporee principalement a des vehicules nutritionnels |
| NO310176B1 (no) | 2000-11-13 | 2001-06-05 | Wadlund As | Sammensetning for hud som inneholder kitosan-konjugert CLA og kitosankonjugert vitamin A eller et <beta>-cyklodekstrin-konjugertvitamin A samt fremgangsmåte for fremstilling og anvendelse avdenne |
| US6528040B1 (en) | 2001-01-18 | 2003-03-04 | Maurine Pearson | EMU oil-based formulations for use as an analgesic, anesthetic and antipruritic |
| JP2004527501A (ja) | 2001-03-05 | 2004-09-09 | ピー. アーネスト,スティーヴン | 経腸処方 |
| ES2238568T3 (es) | 2001-05-30 | 2005-09-01 | Laxdale Limited | Uso del coenzima q (ubiquinona) y acido eicosapentaenoico (epa) para el tratamiento del linfoma no hodgkin y trastornos psiquiatricos o neurologicos. |
| JP2003048831A (ja) | 2001-08-02 | 2003-02-21 | Suntory Ltd | 脳機能の低下に起因する症状あるいは疾患の予防又は改善作用を有する組成物 |
| EP1285590A1 (en) | 2001-08-08 | 2003-02-26 | Société des Produits Nestlé S.A. | Lipid blends |
| AU784852B2 (en) | 2001-08-10 | 2006-07-06 | Mars, Incorporated | Canine support diet |
| US20030032674A1 (en) | 2001-08-13 | 2003-02-13 | Hwang Daniel H. | Use of unsaturated fatty acids to treat severe inflammatory diseases |
| NL1019368C2 (nl) | 2001-11-14 | 2003-05-20 | Nutricia Nv | Preparaat voor het verbeteren van receptorwerking. |
| US6677470B2 (en) | 2001-11-20 | 2004-01-13 | Natural Asa | Functional acylglycerides |
| ITMI20012732A1 (it) | 2001-12-20 | 2003-06-20 | Health Pharma S R L | Integratore alimentare per neuropatici |
| AUPS082102A0 (en) | 2002-03-01 | 2002-03-21 | Women's And Children's Hospital | Therapeutic properties of oils |
| BR0308290A (pt) | 2002-03-08 | 2005-01-11 | Monsanto Technology Llc | Tratamento e prevenção de distúrbios inflamatórios |
| US20040048926A1 (en) | 2002-03-15 | 2004-03-11 | Hoffman Dennis Robert | Use of docosahexaenoic acid and arachidonic acid to enhance the visual development of term infants breast-fed up to the age of six months |
| US20060094784A1 (en) | 2002-05-17 | 2006-05-04 | Masataka Kagawa | Tgf-alpha expression inhibitors |
| US7335481B2 (en) | 2002-07-24 | 2008-02-26 | Christer Owman | Methods of identifying compounds that affect a fatty acid cell-surface receptor |
| AU2003304108B2 (en) | 2002-10-30 | 2007-03-22 | Spherics, Inc. | Nanoparticulate bioactive agents |
| US7074418B2 (en) | 2002-11-18 | 2006-07-11 | Changaris David G | Conjugated fatty acid based emulsion and methods for preparing and using same |
| AU2003293020A1 (en) | 2002-11-26 | 2004-06-18 | George Washington University | Method and composition with conjugated linoleic acid esters |
| US6841573B2 (en) | 2002-11-27 | 2005-01-11 | Molecular Nutrition | Use of arachidonic acid as a method of increasing skeletal muscle mass |
| US20040209953A1 (en) | 2002-12-06 | 2004-10-21 | Wai Lee Theresa Siu-Ling | Glyceride compositions and methods of making and using same |
| US20040208939A1 (en) | 2003-04-18 | 2004-10-21 | Barry Sears | Novel dietary compositions to reduce inflammation |
| GB0311081D0 (en) * | 2003-05-14 | 2003-06-18 | Btg Internat Limted | Treatment of neurodegenerative conditions |
| CA2534711A1 (en) | 2003-08-01 | 2005-02-10 | Medarex, Inc. | Combination therapies for multiple sclerosis |
| ES2304094B2 (es) * | 2003-08-18 | 2010-10-14 | Btg International Limited | Tratamiento de dolencias neurodegenerativas. |
| GB2409644B (en) | 2003-12-31 | 2005-12-21 | Igennus Ltd | Formulation comprising eicosapentaenoic acid or an ester thereof and a triterpene or an ester thereof |
| GB0504362D0 (en) | 2005-03-02 | 2005-04-06 | Btg Int Ltd | Cytokine modulators |
-
2005
- 2005-03-02 GB GBGB0504362.5A patent/GB0504362D0/en not_active Ceased
-
2006
- 2006-03-02 PL PL06710000T patent/PL1853254T3/pl unknown
- 2006-03-02 JP JP2007557595A patent/JP2008531675A/ja active Pending
- 2006-03-02 WO PCT/GB2006/000779 patent/WO2006092623A1/en not_active Ceased
- 2006-03-02 AU AU2006219733A patent/AU2006219733A1/en not_active Abandoned
- 2006-03-02 KR KR1020077022547A patent/KR20070114307A/ko not_active Ceased
- 2006-03-02 AT AT06710000T patent/ATE490768T1/de active
- 2006-03-02 EP EP06710000A patent/EP1853254B1/en not_active Not-in-force
- 2006-03-02 PT PT06710000T patent/PT1853254E/pt unknown
- 2006-03-02 CA CA002598785A patent/CA2598785A1/en not_active Abandoned
- 2006-03-02 ES ES06710000T patent/ES2356925T3/es active Active
- 2006-03-02 CN CNA2006800149575A patent/CN101171003A/zh active Pending
- 2006-03-02 DK DK06710000.8T patent/DK1853254T3/da active
- 2006-03-02 US US11/885,254 patent/US20090137660A1/en not_active Abandoned
- 2006-03-02 DE DE602006018710T patent/DE602006018710D1/de active Active
-
2010
- 2010-07-02 US US12/801,937 patent/US8114903B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB0504362D0 (en) | 2005-04-06 |
| JP2008531675A (ja) | 2008-08-14 |
| PL1853254T3 (pl) | 2011-07-29 |
| HK1110227A1 (en) | 2008-07-11 |
| KR20070114307A (ko) | 2007-11-30 |
| EP1853254B1 (en) | 2010-12-08 |
| CA2598785A1 (en) | 2006-09-08 |
| AU2006219733A1 (en) | 2006-09-08 |
| ATE490768T1 (de) | 2010-12-15 |
| US20090137660A1 (en) | 2009-05-28 |
| US20100297196A1 (en) | 2010-11-25 |
| DK1853254T3 (da) | 2011-03-28 |
| WO2006092623A1 (en) | 2006-09-08 |
| ES2356925T3 (es) | 2011-04-14 |
| EP1853254A1 (en) | 2007-11-14 |
| DE602006018710D1 (de) | 2011-01-20 |
| CN101171003A (zh) | 2008-04-30 |
| US8114903B2 (en) | 2012-02-14 |
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