WO1990003786A1 - Emulsion and use of the emulsion as a parenteral preparation - Google Patents

Emulsion and use of the emulsion as a parenteral preparation Download PDF

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Publication number
WO1990003786A1
WO1990003786A1 PCT/DK1989/000235 DK8900235W WO9003786A1 WO 1990003786 A1 WO1990003786 A1 WO 1990003786A1 DK 8900235 W DK8900235 W DK 8900235W WO 9003786 A1 WO9003786 A1 WO 9003786A1
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WO
WIPO (PCT)
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.)
Ceased
Application number
PCT/DK1989/000235
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French (fr)
Inventor
Tomas Tage Hansen
Sven Erik Godtfredsen
Sven Froekjaer
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Novo Nordisk AS
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Novo Nordisk AS
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Application filed by Novo Nordisk AS filed Critical Novo Nordisk AS
Priority to JP1510969A priority Critical patent/JPH04500974A/en
Publication of WO1990003786A1 publication Critical patent/WO1990003786A1/en
Priority to DK063491A priority patent/DK63491A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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.

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  • 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

The emulsion has an aqueous, continuous phase and contains as the discontinuous phase the triglyceride 2-eicosapentaenoyl-1,3-dioctanoyl glycerol, formulated for parenteral use. This emulsion exhibits a better bioavailability than hitherto known parenteral emulsions used as a source for EPA (eicosapentaenoic acid).

Description

EMULSION AND USE OF THE EMULSION AS A PARENTERAL PREPARATION
The invention relates to an emulsion and a use of the emulsion as a parenteral preparation.
The triglyceride 2-eicosapentaenoyl-l,3-dioctanoyl glycerol is described in US 4,407,052 and S. E. Boustani et al. , Lipids, 22, 711-14 (1987). Also, an emulsion for enteral use of this triglyceride is described. Eicosapentaenoic acid is abbreviated EPA.
As the above 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. Moreover, 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.
Surprisingly, 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. In the liquid form 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.
The use of the above-mentioned 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 higher the purity of the triglyceride, the more efficient the absorption of the triglyceride in the intestines.
Also the invention comprises a use of the emulsion according to the invention as a parenteral preparation.
EXAMPLE 1
A parenteral feeding product was prepared according to the following formula:
Composition for 1000 ml I Lipid 100.0 g
II Egg yolk phospholipids (Lipoid E80) 12.0 g
III Glycerol 22.5 g
IV Water for injection to 1000 ml Production Procedure
II was dispersed in 500 ml of IV by a high shear mixer (Ultra turrax) followed by the addition of I and III. Fianlly water (IV) was added to a total volume of 1000 ml. The whole mixture was further prehomogenized for another 2-3 minutes (ultra turrax) . The pre-emulsion was homogenized in a high pressure homogenizer (MHO Microfluidizer, Microfluidics Corporation, Newton, Mass.). The product was processed 5 times through the Microfluidizer. In order to keep the product temperature below 20°C the product was passed through an ice slurry by each cycle. The oxidation of lipids was prevented by running the process under Argon and by using liquids saturated with Argon.
The product was filled in a suitable package and sterilized in an autoclave at 120°C for 20 minutes.
Analytical data
pH = 6.1
Osmolality = 304 mOsm/kg water Particle size (d2) = 285 nm Limulus test = < 0.5 EU/ml

Claims

1. An emulsion with an aqueous, continuous phase and containing as the discontinuous phase the triglyceride 2- eicosapentaenoyl-1,3-dioctanoyl glycerol, formulated for parenteral use.
2. An emulsion according to Claim 1, wherein the average diameter of the triglyceride globules is between 5 and 1000 nm, and wherein less than 5% of the triglyceride globules exhibits a diameter above 5000 nm.
3. An emulsion according to Claim 2, wherein the amount of the triglyceride in relation to the amount of the entire emulsion is between 2 and 30% by weight, and the emulsion contains glycerol to isotonicity and 0.2 - 10% by weight of an emulsifier.
4. Emulsion according to Claims 1 - 3, wherein the triglycerides have 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%.
5. Use of the emulsion according to Claims 1 - 4, as a parenteral preparation.
PCT/DK1989/000235 1988-10-10 1989-10-10 Emulsion and use of the emulsion as a parenteral preparation Ceased WO1990003786A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP1510969A JPH04500974A (en) 1988-10-10 1989-10-10 Emulsions as emulsions and parenteral preparations
DK063491A DK63491A (en) 1988-10-11 1991-04-10 EMULSION AND USE OF THE EMULSION AS A PARENTERAL PREPARATION

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK5652/88 1988-10-10
DK565288A DK565288D0 (en) 1988-10-11 1988-10-11 PROCEDURE FOR THE PREPARATION OF TRIGLYCERIDES, APPLICATION OF SUCH TRIGLYCERIDES, AND AN EMULSION CONTAINING SUCH TRIGLYCERIDES

Publications (1)

Publication Number Publication Date
WO1990003786A1 true WO1990003786A1 (en) 1990-04-19

Family

ID=8144235

Family Applications (8)

Application Number Title Priority Date Filing Date
PCT/DK1989/000234 Ceased WO1990004010A1 (en) 1988-10-10 1989-10-10 Triglyceride, nutritional composition comprising such triglyceride, and use of the nutritional composition for nutrition
PCT/DK1989/000232 Ceased WO1990004008A1 (en) 1988-10-10 1989-10-10 Triglycerides, nutritional composition comprising such triglycerides, and use of the nutritional composition for nutrition
PCT/DK1989/000238 Ceased WO1990004012A1 (en) 1988-10-10 1989-10-10 Triglycerides, nutritional composition comprising such triglycerides, and use of the nutritional composition for nutrition
PCT/DK1989/000233 Ceased WO1990004009A1 (en) 1988-10-10 1989-10-10 Triglycerides, nutritional composition comprising such triglycerides, and use of the nutritional composition for nutrition
PCT/DK1989/000236 Ceased WO1990003787A1 (en) 1988-10-10 1989-10-10 Emulsion and use of the emulsion as a parenteral preparation
PCT/DK1989/000239 Ceased WO1990004013A1 (en) 1988-10-10 1989-10-10 Triglycerides, composition comprising such triglycerides, and use of such composition
PCT/DK1989/000237 Ceased WO1990004011A1 (en) 1988-10-10 1989-10-10 Triglycerides, nutritional composition comprising such triglycerides, and use of the nutritional composition for nutrition
PCT/DK1989/000235 Ceased WO1990003786A1 (en) 1988-10-10 1989-10-10 Emulsion and use of the emulsion as a parenteral preparation

Family Applications Before (7)

Application Number Title Priority Date Filing Date
PCT/DK1989/000234 Ceased WO1990004010A1 (en) 1988-10-10 1989-10-10 Triglyceride, nutritional composition comprising such triglyceride, and use of the nutritional composition for nutrition
PCT/DK1989/000232 Ceased WO1990004008A1 (en) 1988-10-10 1989-10-10 Triglycerides, nutritional composition comprising such triglycerides, and use of the nutritional composition for nutrition
PCT/DK1989/000238 Ceased WO1990004012A1 (en) 1988-10-10 1989-10-10 Triglycerides, nutritional composition comprising such triglycerides, and use of the nutritional composition for nutrition
PCT/DK1989/000233 Ceased WO1990004009A1 (en) 1988-10-10 1989-10-10 Triglycerides, nutritional composition comprising such triglycerides, and use of the nutritional composition for nutrition
PCT/DK1989/000236 Ceased WO1990003787A1 (en) 1988-10-10 1989-10-10 Emulsion and use of the emulsion as a parenteral preparation
PCT/DK1989/000239 Ceased WO1990004013A1 (en) 1988-10-10 1989-10-10 Triglycerides, composition comprising such triglycerides, and use of such composition
PCT/DK1989/000237 Ceased WO1990004011A1 (en) 1988-10-10 1989-10-10 Triglycerides, nutritional composition comprising such triglycerides, and use of the nutritional composition for nutrition

Country Status (8)

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

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WO1992015283A1 (en) * 1991-03-01 1992-09-17 Novo Nordisk A/S Parenteral emulsion
ES2136189T3 (en) * 1993-01-15 1999-11-16 Abbott Lab STRUCTURED LIPIDS.
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 (en) 1995-04-28 2001-06-13 Loders Croklaan B.V. Triglycerides, rich in polyunsaturated fatty acids
US5993221A (en) * 1997-05-01 1999-11-30 Beth Israel Deaconess Medical Center, Inc. Dietary formulation comprising arachidonic acid and methods of use
IT1292126B1 (en) * 1997-06-11 1999-01-25 Guido Galliani WAX ESTERS ENRICHED IN UNSATURATED OMEGA-3 FATTY ACIDS, THEIR PREPARATION AND USE
PT893064E (en) * 1997-07-22 2003-04-30 Nestle Sa LIPIDIC COMPOSITION FOR CHILD FORMULATION AND PREPARATION PROCESS
WO2003033632A1 (en) 2001-10-18 2003-04-24 Council Of Scientific And Industrial Research Cholesterol lowering structured lipids with omega 6 pufa
GB2422373B (en) * 2003-08-18 2008-05-21 Btg Int Ltd Treatment of neurodegenerative conditions
JP6126309B2 (en) * 2015-01-26 2017-05-10 日清オイリオグループ株式会社 Fats and oils
US11679091B2 (en) 2018-02-09 2023-06-20 Nippon Suisan Kaisha, Ltd. Lymphatic circulation improving agents
CA3114461A1 (en) * 2018-10-15 2020-04-23 M.A. Med Alliance SA Coating for intraluminal expandable catheter providing contact transfer of drug micro-reservoirs
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

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