EP0437522A1 - Emulsion et son utilisation comme preparation parenterale - Google Patents

Emulsion et son utilisation comme preparation parenterale

Info

Publication number
EP0437522A1
EP0437522A1 EP89911782A EP89911782A EP0437522A1 EP 0437522 A1 EP0437522 A1 EP 0437522A1 EP 89911782 A EP89911782 A EP 89911782A EP 89911782 A EP89911782 A EP 89911782A EP 0437522 A1 EP0437522 A1 EP 0437522A1
Authority
EP
European Patent Office
Prior art keywords
emulsion
triglyceride
parenteral
epa
emulsion according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP89911782A
Other languages
German (de)
English (en)
Inventor
Tomas Tage Hansen
Sven Erik Godtfredsen
Sven Froekjaer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novo Nordisk AS
Original Assignee
Novo Nordisk AS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8144235&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0437522(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Novo Nordisk AS filed Critical Novo Nordisk AS
Publication of EP0437522A1 publication Critical patent/EP0437522A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/003—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K40/00—Shaping or working-up of animal feeding-stuffs
    • A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/30—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with trihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
    • C11C1/002—Sources of fatty acids, e.g. natural glycerides, characterised by the nature, the quantities or the distribution of said acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids

Definitions

  • the invention relates to an emulsion and a use of the emulsion as a parenteral preparation.
  • triglyceride is important as a nutrient, especially " for diseased humans, there is a need for an emulsion of 2-eicosapentaenoyl-l,3-dioctanoyl glycerol, which can be used for parenteral nutrition, and which exhibits a better bioavailability than hitherto known parenteral emulsions used as a source for EPA.
  • a very important clinical aspect in regard to the bioavailability is the slower metabolism in comparison to emulsions containing MCT, which are known to cause metabolic acidosis when infused intravenously.
  • the emulsion according to the invention with an aqueous continuous phase and containing as the discontinous phase the triglyceride 2-eicosapentaenoyl-l,3-dioctanoyl glycerol, is characterized by the fact that it is formulated for parenteral use. Any worker skilled in the art will know in principle how to compose such formulation. Surprisingly it has been found that the emulsion according to the invention exhibits a better bioavailability than hitherto known parenteral emulsions used as a source for EPA.
  • the above-mentioned triglycerides turn out, surprisingly, to be very efficient sources of energy in when applied in parenteral nutrition - the EPA acid moiety of the triglycerides being in an optimal position in the molecule in respect to their cleavage by lipoprotein lipase.
  • the above triglycerides appear to exhibit physical properties which allow facile formulation of the compounds in liquid products as well as in powdered products exhibiting excellent wetability properties.
  • the products of the invention possess excellent stabilities making sterilization of e.g. parenteral products containing the above-mentioned triglycerides reliable, easy and safe.
  • the above-mentioned triglycerides are advantageously applied in such emulsions due to their fast conversion by lipoprotein lipase and endothelial lipase and the consequential avoidance of the discomfort and side effects of lipolipaedemia.
  • Arachidonic acid applied in above triglycerides is thus cleared quickly and efficiently thereby providing the essential fatty acid concomitantly with short chain acids useful as energy substrates.
  • triglycerides in parenteral nutritional products is further particularly advantageous since the relatively high polarity of the triglycerides favour the stability of their emulsions which are subjected to severe heat treatments during their manufacturing. Use of such emulsion is particularly advantageous for nutrition of severely ill patients e.g. post-operatively.
  • Another advantage of the products of the invention has to do with the stability of the EPA towards oxidation and thus the avoidance of problems associated with oxidation of polyunsaturated fatty acids. It thus turns out that products according to the invention allows preparation of EPA containing lipids with an improved quality of EPA as compared to other sources of the essential fatty acid. Detrimental processes of polyunsaturated fats and oils leading to negative nutritional forms are thus commonly associated with gastric and intestinal problems due to oxidation and polymerisation products of the polyunsaturated fatty acid. Such oxidized forms of EPA can interfere with nitrogen uptake by interacting with sensitive amino acids. These highly undesired effects are diminished or even avoided by applying triglycerides according to the invention.
  • a preferred embodiment of the emulsion according to the invention is characterized by the fact that the average diameter of the triglyceride globules is between 5 and 1000 nm, and that less than 5% of the triglyceride globules exhibits a diameter above 5000 nm.
  • This emulsion is well suited as a parenteral emulsion and shows a good bioavailability.
  • a preferred embodiment of the emulsion according to the invention is characterized by the fact that the average diameter of the triglyceride globules is between 5 and 1000 nm, that less than 5% of the triglyceride globules exhibits a diameter above 5000 nm, that the amount of the triglyceride in relation to the amount of the entire emulsion is between 2 and 30% by weight, and that the emulsion contains glycerol to isotonicity and 0.2 - 10% by weight of an emulsifier.
  • This emulsion is very well suited as a parenteral emulsion and shows a superior absorption ability.
  • a preferred emulsifier is a phospholipid.
  • a preferred embodiment of the emulsion according to the invention is characterized by the fact that the triglyceride has a purity of at least 10%, preferably at least 30%, more preferably at least 50%, even more preferably at least 75%, and most preferably at least 90%.
  • the invention comprises a use of the emulsion according to the invention as a parenteral preparation.
  • a parenteral feeding product was prepared according to the following formula:
  • the product was filled in a suitable package and sterilized in an autoclave at 120°C for 20 minutes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Public Health (AREA)
  • Zoology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Animal Husbandry (AREA)
  • Hematology (AREA)
  • Microbiology (AREA)
  • Obesity (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'émulsion comporte une phase aqueuse continue et contient à titre de phase discontinue le triglycéride 2-eicosapentaenoyl-1,3-dioctanoyl glycérol, formulé pour une utilisation parentérale. L'émulsion présente une meilleure biodisponibilité par rapport aux émulsions parentérales connues à ce jour, utilisées comme source d'EPA (acide eicosapentaénoïque).
EP89911782A 1988-10-10 1989-10-10 Emulsion et son utilisation comme preparation parenterale Withdrawn EP0437522A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK5652/88 1988-10-10
DK565288A DK565288D0 (da) 1988-10-11 1988-10-11 Fremgangsmaade til fremstilling af triglycerider, anvendelse af saadanne triglycerider og en emulsion, der indeholder saadanne triglycerider

Publications (1)

Publication Number Publication Date
EP0437522A1 true EP0437522A1 (fr) 1991-07-24

Family

ID=8144235

Family Applications (8)

Application Number Title Priority Date Filing Date
EP89911780A Expired - Lifetime EP0437520B1 (fr) 1988-10-10 1989-10-10 Triglyceride et composition nutritionnelle la comprenant
EP89911778A Expired - Lifetime EP0437518B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition les comprenant
EP89911781A Withdrawn EP0437521A1 (fr) 1988-10-10 1989-10-10 Emulsion et son utilisation comme preparation parenterale
EP89911779A Expired - Lifetime EP0437519B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant
EP89911783A Expired - Lifetime EP0438483B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant
EP89911784A Expired - Lifetime EP0437523B1 (fr) 1988-10-10 1989-10-10 Triglycerides, composition nutritionnelle les comprenant, et utilisation de la composition nutritionnelle pour la nutrition
EP89911782A Withdrawn EP0437522A1 (fr) 1988-10-10 1989-10-10 Emulsion et son utilisation comme preparation parenterale
EP89911785A Expired - Lifetime EP0437524B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant.

Family Applications Before (6)

Application Number Title Priority Date Filing Date
EP89911780A Expired - Lifetime EP0437520B1 (fr) 1988-10-10 1989-10-10 Triglyceride et composition nutritionnelle la comprenant
EP89911778A Expired - Lifetime EP0437518B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition les comprenant
EP89911781A Withdrawn EP0437521A1 (fr) 1988-10-10 1989-10-10 Emulsion et son utilisation comme preparation parenterale
EP89911779A Expired - Lifetime EP0437519B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant
EP89911783A Expired - Lifetime EP0438483B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant
EP89911784A Expired - Lifetime EP0437523B1 (fr) 1988-10-10 1989-10-10 Triglycerides, composition nutritionnelle les comprenant, et utilisation de la composition nutritionnelle pour la nutrition

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP89911785A Expired - Lifetime EP0437524B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant.

Country Status (8)

Country Link
EP (8) EP0437520B1 (fr)
JP (8) JPH04501116A (fr)
AU (8) AU636582B2 (fr)
CA (8) CA2000391A1 (fr)
DE (1) DE68909053T2 (fr)
DK (1) DK565288D0 (fr)
WO (8) WO1990004010A1 (fr)
ZA (2) ZA897693B (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK565288D0 (da) * 1988-10-11 1988-10-11 Novo Industri As Fremgangsmaade til fremstilling af triglycerider, anvendelse af saadanne triglycerider og en emulsion, der indeholder saadanne triglycerider
WO1992015283A1 (fr) * 1991-03-01 1992-09-17 Novo Nordisk A/S Emulsion parenterale
ES2136189T3 (es) * 1993-01-15 1999-11-16 Abbott Lab Lipidos estructurados.
US5574065A (en) * 1994-04-21 1996-11-12 Clintec Nutrition Co. Method and composition for normalizing injury response
US5589468A (en) * 1995-01-13 1996-12-31 Clintec Nutrition Co. Method for providing nutrition to elderly patients
EP0739590B1 (fr) 1995-04-28 2001-06-13 Loders Croklaan B.V. Triglycérides, riches en acides gras polyinsaturés
US5993221A (en) * 1997-05-01 1999-11-30 Beth Israel Deaconess Medical Center, Inc. Dietary formulation comprising arachidonic acid and methods of use
IT1292126B1 (it) * 1997-06-11 1999-01-25 Guido Galliani Esteri cerosi arricchiti in acidi grassi omega-3 insaturi,loro preparazione ed uso
PT893064E (pt) * 1997-07-22 2003-04-30 Nestle Sa Composicao lipidica para formulacao infantil e processo de preparacao
WO2003033632A1 (fr) 2001-10-18 2003-04-24 Council Of Scientific And Industrial Research Lipides structures abaissant le taux de cholesterol avec omega 6 pufa
GB2422373B (en) * 2003-08-18 2008-05-21 Btg Int Ltd Treatment of neurodegenerative conditions
JP6126309B2 (ja) * 2015-01-26 2017-05-10 日清オイリオグループ株式会社 油脂
US11679091B2 (en) 2018-02-09 2023-06-20 Nippon Suisan Kaisha, Ltd. Lymphatic circulation improving agents
CA3114461A1 (fr) * 2018-10-15 2020-04-23 M.A. Med Alliance SA Revetement pour catheter expansible intraluminal permettant un transfert par contact de microreservoirs de medicament
US20240156773A1 (en) * 2021-03-26 2024-05-16 The Nisshin Oillio Group, Ltd. Method for increasing blood decanoic acid concentration, blood-decanoic-acid-concentration-increasing agent, pharmaceutical composition, and food composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2515174A1 (fr) 1981-10-23 1983-04-29 Roussel Uclaf Nouveaux triglycerides, procede de preparation et d'applications en dietetique et en therapeutique
US4701469A (en) * 1983-04-15 1987-10-20 Roussel Uclaf Triglycerides, process for therapeutical applications and compositions containing them
US4607052A (en) * 1983-04-15 1986-08-19 Roussel-Uclaf Triglycerides, dietetic and therapeutical applications and compositions containing them
US4701468A (en) 1983-04-15 1987-10-20 Roussel-Uclaf Oxidized triglycerides having therapeutic utility
US4753963A (en) * 1985-09-26 1988-06-28 The Procter & Gamble Company Nutritional fat suitable for enteral and parenteral products
JPS6387988A (ja) * 1986-10-01 1988-04-19 Nisshin Oil Mills Ltd:The 消化吸収性の良い油脂
JPS63297342A (ja) * 1987-05-28 1988-12-05 Nisshin Oil Mills Ltd:The 合成油脂ならびにこれを含有する脂肪乳剤輸液および経腸栄養剤
DK565288D0 (da) * 1988-10-11 1988-10-11 Novo Industri As Fremgangsmaade til fremstilling af triglycerider, anvendelse af saadanne triglycerider og en emulsion, der indeholder saadanne triglycerider

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9003786A1 *

Also Published As

Publication number Publication date
AU4420489A (en) 1990-05-01
EP0437523A1 (fr) 1991-07-24
CA2000397A1 (fr) 1990-04-10
DE68909053T2 (de) 1994-01-05
EP0437524B1 (fr) 1992-04-15
AU640353B2 (en) 1993-08-26
EP0438483A1 (fr) 1991-07-31
EP0437521A1 (fr) 1991-07-24
WO1990003786A1 (fr) 1990-04-19
JPH04501116A (ja) 1992-02-27
AU631816B2 (en) 1992-12-10
EP0437523B1 (fr) 1993-09-08
WO1990003787A1 (fr) 1990-04-19
AU4421189A (en) 1990-05-01
CA2000392A1 (fr) 1990-04-10
EP0437520A1 (fr) 1991-07-24
EP0437519A1 (fr) 1991-07-24
WO1990004012A1 (fr) 1990-04-19
CA2000394A1 (fr) 1990-04-10
EP0437518A1 (fr) 1991-07-24
WO1990004013A1 (fr) 1990-04-19
JPH04501114A (ja) 1992-02-27
EP0437520B1 (fr) 1992-04-15
AU639675B2 (en) 1993-08-05
CA2000395A1 (fr) 1990-04-10
ZA897693B (en) 1990-06-27
AU4422289A (en) 1990-05-01
DK565288D0 (da) 1988-10-11
JPH04500974A (ja) 1992-02-20
CA2000398A1 (fr) 1990-04-10
WO1990004009A1 (fr) 1990-04-19
AU636582B2 (en) 1993-05-06
EP0437519B1 (fr) 1992-04-15
CA2000393A1 (fr) 1990-04-10
EP0438483B1 (fr) 1992-04-15
AU4421989A (en) 1990-05-01
JPH04500972A (ja) 1992-02-20
CA2000391A1 (fr) 1990-04-10
WO1990004008A1 (fr) 1990-04-19
EP0437524A1 (fr) 1991-07-24
AU4420589A (en) 1990-05-01
CA2000396A1 (fr) 1990-04-10
JPH04500971A (ja) 1992-02-20
ZA897692B (en) 1990-06-27
AU629866B2 (en) 1992-10-15
WO1990004011A1 (fr) 1990-04-19
AU4421089A (en) 1990-05-01
WO1990004010A1 (fr) 1990-04-19
EP0437518B1 (fr) 1992-04-15
JPH04501113A (ja) 1992-02-27
DE68909053D1 (de) 1993-10-14
JPH04500973A (ja) 1992-02-20
AU4422489A (en) 1990-05-01
AU4422089A (en) 1990-05-01
JPH04501115A (ja) 1992-02-27
AU630120B2 (en) 1992-10-22

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