EP0437521A1 - Emulsion et son utilisation comme preparation parenterale - Google Patents

Emulsion et son utilisation comme preparation parenterale

Info

Publication number
EP0437521A1
EP0437521A1 EP89911781A EP89911781A EP0437521A1 EP 0437521 A1 EP0437521 A1 EP 0437521A1 EP 89911781 A EP89911781 A EP 89911781A EP 89911781 A EP89911781 A EP 89911781A EP 0437521 A1 EP0437521 A1 EP 0437521A1
Authority
EP
European Patent Office
Prior art keywords
emulsion
triglycerides
parenteral
triglyceride
glycerol
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Withdrawn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
EP89911781A
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=EP0437521(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 EP0437521A1 publication Critical patent/EP0437521A1/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Withdrawn legal-status Critical Current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, 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, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, 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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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.
  • the triglyceride 2-oleyl-1 , 3-dioctanoy1 glycerol (2[9-cis-octadecenoyl]-l,3-dioctanoyl glycerol) is described in Am. J. Clin. Nutr. 1987; 45:940-5 and the triglyceride 2-oleyl-l, 3-didecanoyl glycerol (2-[9-cis- octadecenoyl]-l,3-didecanoyl glycerol) is described in F. H. Mattson et al. , Journal of lipid research, 5, 374-77 (1964). Also, an emulsion for enteral use of the first mentioned of the above two triglycerides is described.
  • 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-oleyl-l,3-di(octanoyl/decanoyl) 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.
  • 2-oleyl-l,3-di(octanoyl/decanoyl) glycerol encompasses both the pure 1,3-dioctanoyl triglyceride, the pure 1,3-didecanoyl triglyceride, and furthermore the l-octanoyl-3-decanoyl triglyceride and the 1- decanoyl-3-octanoyl triglyceride, the 2-position of course in all cases being occupied by oleic acid.
  • the emulsion according to the invention exhibits a better bioavailability than hitherto known parenteral emulsions used as a source for oleic acid.
  • the above-mentioned triglycerides turn out, surprisingly, to be very efficient sources of energy when applied in parenteral nutrition - the oleic acid moiety of the triglycerides being in an optimal position in the molecule in respect to their cleavage by lipoprotein lipase.
  • the above-mentioned 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 triglycerides reliable, easy and safe.
  • 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 triglycerides of the invention are thus cleared quickly and efficiently thereby providing the essential fatty acid concomitantly with short chain acids useful as energy substrates.
  • 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 triglycerides 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.
  • 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.
  • a preferred embodiment of the emulsion according to the invention is characterized by the fact that the triglycerides have a purity of at least 30%, preferably at least 50%, 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.
  • 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:
  • 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.
  • MHO Microfluidizer Microfluidics Corporation, Newton, Mass.
  • the superiority of the compounds of the invention was illustrated by comparing the rate of their hydrolysis by lipoprotein lipase with the rate of hydrolysis of the non- structured lipid (LLL) and the commercial product Intralipid which contains long chain fatty acids at all positions of the triglyceride molecules. All emulsions were made as described in Example 1. As is apparent from the table below the structured lipid was hydrolyzed at an increased rate thus offering advantages as mentioned above.

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)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Nutrition Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Animal Husbandry (AREA)
  • Mycology (AREA)
  • Hematology (AREA)
  • Microbiology (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'émulsion comporte une phase aqueuse continue et contient à titre de phase discontinue les triglycérides 2-oleyl-1,3-di(octanoyl/décanoyl), formulés pour une utilisation parentérale. Cette émulsion présente une meilleure biodisponibilité que les émulsions parentérales connues à ce jour qui sont utilisées comme source d'acide oléique.
EP89911781A 1988-10-10 1989-10-10 Emulsion et son utilisation comme preparation parenterale Withdrawn EP0437521A1 (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
EP0437521A1 true EP0437521A1 (fr) 1991-07-24

Family

ID=8144235

Family Applications (8)

Application Number Title Priority Date Filing Date
EP89911779A Expired - Lifetime EP0437519B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant
EP89911785A Expired - Lifetime EP0437524B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant.
EP89911782A Withdrawn EP0437522A1 (fr) 1988-10-10 1989-10-10 Emulsion et son utilisation comme preparation parenterale
EP89911778A Expired - Lifetime EP0437518B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition les comprenant
EP89911780A Expired - Lifetime EP0437520B1 (fr) 1988-10-10 1989-10-10 Triglyceride et composition nutritionnelle la comprenant
EP89911783A Expired - Lifetime EP0438483B1 (fr) 1988-10-10 1989-10-10 Triglycerides et composition nutritionnelle les comprenant
EP89911781A Withdrawn EP0437521A1 (fr) 1988-10-10 1989-10-10 Emulsion et son utilisation comme preparation parenterale
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 Before (6)

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

Family Applications After (1)

Application Number Title Priority Date Filing Date
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

Country Status (8)

Country Link
EP (8) EP0437519B1 (fr)
JP (8) JPH04500972A (fr)
AU (8) AU631816B2 (fr)
CA (8) CA2000395A1 (fr)
DE (1) DE68909053T2 (fr)
DK (1) DK565288D0 (fr)
WO (8) WO1990003787A1 (fr)
ZA (2) ZA897693B (fr)

Families Citing this family (14)

* 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
CA2151820C (fr) * 1993-01-15 2000-11-28 Stephen Joseph Demichele Lipides structures
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
ATE230935T1 (de) * 1997-07-22 2003-02-15 Nestle Sa Lipidzusammensetzung für säuglingsnährpräparat und herstellungsverfahren
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
DE112004001520B4 (de) * 2003-08-18 2008-04-10 Btg International Ltd. Verwendung eines Lipidglyzerids festgelegter Struktur zur Herstellung eines Medikamentes zur Behandlung der multiplen Sklerose
EP3251518A4 (fr) * 2015-01-26 2018-09-05 The Nisshin OilliO Group, Ltd. Huile ou graisse
JP7295812B2 (ja) 2018-02-09 2023-06-21 株式会社ニッスイ リンパ循環改善剤
WO2020081455A1 (fr) * 2018-10-15 2020-04-23 M.A. Med Alliance SA Revêtement pour cathéter expansible intraluminal permettant un transfert par contact de microréservoirs de médicament

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
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
US4701469A (en) * 1983-04-15 1987-10-20 Roussel Uclaf Triglycerides, process for therapeutical applications and compositions containing them
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 WO9003787A1 *

Also Published As

Publication number Publication date
EP0437518A1 (fr) 1991-07-24
AU4421189A (en) 1990-05-01
JPH04501116A (ja) 1992-02-27
EP0437524B1 (fr) 1992-04-15
EP0437520B1 (fr) 1992-04-15
DK565288D0 (da) 1988-10-11
EP0437522A1 (fr) 1991-07-24
AU4421989A (en) 1990-05-01
EP0437523A1 (fr) 1991-07-24
WO1990003787A1 (fr) 1990-04-19
AU640353B2 (en) 1993-08-26
EP0437519A1 (fr) 1991-07-24
WO1990004008A1 (fr) 1990-04-19
ZA897693B (en) 1990-06-27
EP0437524A1 (fr) 1991-07-24
CA2000396A1 (fr) 1990-04-10
AU639675B2 (en) 1993-08-05
JPH04501113A (ja) 1992-02-27
EP0437523B1 (fr) 1993-09-08
EP0437519B1 (fr) 1992-04-15
WO1990004011A1 (fr) 1990-04-19
EP0437518B1 (fr) 1992-04-15
WO1990003786A1 (fr) 1990-04-19
DE68909053T2 (de) 1994-01-05
WO1990004010A1 (fr) 1990-04-19
ZA897692B (en) 1990-06-27
AU4422089A (en) 1990-05-01
JPH04500973A (ja) 1992-02-20
JPH04500972A (ja) 1992-02-20
JPH04500971A (ja) 1992-02-20
CA2000393A1 (fr) 1990-04-10
CA2000391A1 (fr) 1990-04-10
JPH04500974A (ja) 1992-02-20
DE68909053D1 (de) 1993-10-14
CA2000398A1 (fr) 1990-04-10
WO1990004009A1 (fr) 1990-04-19
AU4422289A (en) 1990-05-01
CA2000392A1 (fr) 1990-04-10
AU630120B2 (en) 1992-10-22
AU636582B2 (en) 1993-05-06
AU629866B2 (en) 1992-10-15
AU4421089A (en) 1990-05-01
WO1990004013A1 (fr) 1990-04-19
JPH04501115A (ja) 1992-02-27
CA2000397A1 (fr) 1990-04-10
AU4420589A (en) 1990-05-01
AU4422489A (en) 1990-05-01
EP0438483A1 (fr) 1991-07-31
EP0438483B1 (fr) 1992-04-15
JPH04501114A (ja) 1992-02-27
WO1990004012A1 (fr) 1990-04-19
CA2000394A1 (fr) 1990-04-10
AU4420489A (en) 1990-05-01
CA2000395A1 (fr) 1990-04-10
AU631816B2 (en) 1992-12-10
EP0437520A1 (fr) 1991-07-24

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