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GB2223943A - Oral disage forms of omega-3 polyunsaturated acids - Google Patents

Oral disage forms of omega-3 polyunsaturated acids Download PDF

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Publication number
GB2223943A
GB2223943A GB8824709A GB8824709A GB2223943A GB 2223943 A GB2223943 A GB 2223943A GB 8824709 A GB8824709 A GB 8824709A GB 8824709 A GB8824709 A GB 8824709A GB 2223943 A GB2223943 A GB 2223943A
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Prior art keywords
lt
rti
form
acid
enteric
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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Withdrawn
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GB8824709A
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GB8824709D0 (en )
Inventor
Roger Andre Pluess
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Tillotts Pharma AG
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Tillotts Pharma AG
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/48Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4891Coated capsules; Multilayered drug free capsule shells
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic, hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/20Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids

Abstract

Omega-3 polyunsaturated acids, especially EPA and/or DHA, in free acid form or as pharmaceutically acceptable salts are presented in enteric dosage forms to overcome the problems of belching and the risk of oxidation in the stomach associated with the oral administration of said acids. The acids can be used alone or with other active principles, especially linolenic acid, gamma-linolenic acid, and/or dihomo-gamma-linolenic acid. Preferably, the enteric dosage form is an enterically coated capsule such as a soft or, especially, hard gelatine capsule.

Description

<RTI>CRAWL</RTI> DOSAGE FORMS <RTI>()E</RTI> <RTI>OME(sA-3</RTI> POLYUNSATURATED <RTI>A(:ILS</RTI> The present invention relates to the oral aaministration of omega-3 <RTI>polyunsaturateo</RTI> acias especially, but not exclusively, all-cis-5,8,11,14,17-eicosapentaenoic acid (i.e. all-cis-fatty acia 20:5 omega-3; EPA) and/or 22:6 omega-3-docosahexaenioc <RTI>acia</RTI> <RTI>(LHA).</RTI> In particular, it provides enteric <RTI>dosage</RTI> forms of omeya-3 polyunsaturatea acids.

It has been known for many years that the low occurrence of aetherosclerotic cardiovascular diseases <RTI>amonyst</RTI> Greenland Eskimos ana the low mortality rate of cardiovascular patients in Scandinavia is attributable to the consumption of relatively high amounts of fish oil. The relevant active <RTI>inyredients</RTI> in fish oil have been identified as the omega-3 polyunsaturated acias EPA and DHA, which are present in their <RTI>triglyceride</RTI> and/or other esteritied forms. The use of <RTI>EPA</RTI> in free acid form or as a pharmaceutically acceptable salt, ester or amide is disclosed in <RTI>GB-A-1604554</RTI> and GB-A-2033745.Further, US-A-4097602 disclosed the inhibition of blooa platelet aggregation by administration of EPA in its free acid form or as a salt or lower alkyl ester. <RTI>kore</RTI> recently, US-A-4526902 disclosed the prophlyaxis of thrombo-embolic conditions by simultaneous <RTI>aoministration</RTI> of EPA ana/or <RTI>DhA</RTI> with one or more of linoleic, yamma-linolenic or dihomo-gamma-linolenic acid. The said acids can be present as the free acid or as pharmaceutically acceptable salts, or esters or amides thereof.

Formulations usea or proposea for the administration of EPA and/or <RTI>l)hA</RTI> include oral, rectal, topical, vaginal, intrapulmonary and parenteral formulations. Usually, oral formulations have been employea, especially soft gelatine capsules. However, a problem associated with such oral administration is belching resulting in an unpleasant fishy smell ana taste following disintegration or dissolution of the oral formulation in the stomach. Such a problem previously was well established in the administration of cod liver oil capsules which, because of the vitamin A and D content of the oil, have been used for many decades as a <RTI>dietary'</RTI> supplement.

When EPA and/or DHA are administered in the form of a derivative thereof, usually an alkyl ester or triglyceride, it must be converted into the free fatty acid before beiny absorbea by the boat. The conversion of ester is carried out in the stomach by the pancreatic enzyme Lipase. However, not all patients produce sufficient Lipase to properly convert the derivative into free tatty acid <RTI>form.</RTI> For example, the production of Lipase may be reduced, or even eliminated, as a result of disease or due to alcohol, smoking, stress etc. Accordingly, there is good reason to prefer to use EPA and/or <RTI>LHA</RTI> in the free acid form.

however, because of their <RTI>polyunsaturation</RTI> the free fatty acids are prone to rapid oxidation, which problem is not encountered with the esters. Although antioxidants, e.g. gamma-tocopherol, are used to prevent or at least reduce oxidation, the present Inventor suspects that significant oxidation of the acid takes place in the stomach thereby reducing the availability of the fatty acids.

The teaching and practice in the art to <RTI>aate</RTI> has been that the free acid is administered orally in the same manner as the esters.

The present Inventor has <RTI>appreciatec</RTI> that the long standing problem of belching with the accompanying fishy smell and taste associated with the oral administration of EPA and/or DHA and the risk of oxidation in the stomach can simply and readily be overcome by use of an enteric dosage form (i.e. a dosage form which, when taken orally, will pass through the stomach substantially without release of the active principle but which will release the active principle in the intestine). Although enteric dosage forms are widely used, there was, to the best of our knowledge, no previous proposal that omega-3 polyunsaturated free acias should be presented in enteric dosage form ana it had not been appreciated that there was any reason or advantage arising <RTI>from</RTI> the use of that form.Thus, the present invention resiaes in the enteric presentation of omega-3 polyunsaturatea free acias as aistinct <RTI>front</RTI> enteric dosage forms in general.

The present invention provides an enteric dosage form containing as an active principle an omega-3 polyunsaturated acid in free acid form or as a pharmaceutically acceptable salt thereof. Further, the invention provides the use of said enteric dosage forms in the treatment or prophylaxis of thrombo-embolic conditions. It also provides said enteric dosage forms for the treatment of other conditions for which omega-3 polyunsaturatea acias in their free or precursor form, such as their glyceride or alkyl esters, are indicatea. Such conditions incluae rheumatoid arthritis, diabetes mellitus, migraine, psoriasis, cancer, ana hypercholesterolaemia ana as a dietetic.

As indicated previously, it is preferred that the omega-3 polyunsaturated acid is EPA, DHA or a mixture thereof. It is present in free acid form or as a pharmaceutically acceptable salt thereof and can be present as the sole active principle or with other active principles, especially linoleic acid, gamma-linolenic acid and/or <RTI>dihomo-gamma-linolenic</RTI> acid in free acid or salt form.

<RTI>c)rnega-3</RTI> <RTI>pc,lyunsaturatea</RTI> acias are <RTI>reaaily</RTI> <RTI>oxioised</RTI> and hence an antioxidant usually will be present. The presently preferred antioxidant is gamma-tocopherol but other pharmacoloyically acceptable antioxidants can be used, tor example butylated hydroxy anisole, butylatea hydroxy toluene, propyl gallate or a quinone.

<RTI>lhe</RTI> enteric aosage form may also contain one or more pharmaceutically acceptable excipients depending upon the precise nature of the dosage form.

Suitably, the enteric dosage form can be an enterically coated tablets containing the omega-3 polyunsaturated acid in a microencapsulated form or loaded on a suitable absorbent. However, it is preferred that the enteric dosage form is an enterically coated capsule, especially a soft or, more especially, hard gelatine capsule.

Enteric coatings are widely used in the pharmaceutical industry and are formed of substances which are relatively insoluble in the acid medium of the stomach but disintegrate in the medium of the small intestine. Suitable enteric coatings <RTI>incluae</RTI> cellulose acetate phthalate and polymethacrylate.

Usually, the omega-3 polyunsaturated acid will be administered in a daily dosage of 20 to 50 <RTI>ing/kg,</RTI> especially 30-40 mg/kg. The actual dose will vary depending inter alia on the identity of the omega-3 polyunsaturated acid and the nature and degree of the disorder being treatea. Usually, each unit dose will contain 250 to 1000 mg, especially 400 to 800 mg.

<RTI>Ihe</RTI> following is a description, by way of example only, of a presently preferred embodiment of the invention.

Example Transparent hard gelatine capsules (size 0), consisting of 14% water and 86% gelatine were each filled with 500 mg of a fish oil concentrate (EPACHOL <RTI>60U)</RTI> supplied by <RTI>Messes.</RTI> <RTI>E;PA</RTI> Limitea <RTI>(Winosor,</RTI> Ontario, Canada). The concentrate contains about 32% by weight free EPA, about <RTI>28%</RTI> by weight free DhA and <RTI>0.02%</RTI> by weight gamma-tocopherol. It does not contain any cholesterol, cetoleic acid or saturatea fatty acias and is an oily liquid of brown colour having a characteristic odour.It has the following physico-chemical properties: acid value 160 iodine value 340 peroxide value 3 saponification value 190 saponifiable matter 1.25 relative density 0.935 refractive index <RTI> 1.49</RTI> The filled gelatine capsules were placed in a coating tower where they were carriea in a <RTI>heatea</RTI> <RTI>(55"C)</RTI> air stream whilst being sprayed with an enteric coating solution. <RTI>lhe</RTI> coating solution had the following composition by weight: cellulose acetate phthalate BPC 40 mg ethyl phthalate BPC 12 mg methylene chloride 616 <RTI>mgi</RTI> ethyl alcohol <RTI>95%</RTI> <RTI>I.E.</RTI> 128 mg.

Sufficient coating solution was applied to proviae a theoretical coating of 6 mg/2, which is an excess of that theoretically required in order to allow for losses auring the coating process.

Claims (3)

1. An enteric dosage form containing as an active principle an omega-3 polyunsaturated acid in free acid form or as a pharmaceutically acceptable salt thereof.
2. An enteric dosage form as claimed in Claim 1, wherein said acid is EPA, DHA or a mixture thereof.
3. An enteric dosage form as claimed in Claim 1 or Claim 2, wherein said acid is present in free acid form 4 An enteric dosage form as claimed in any one of the preceding claims, wherein said acid or salt is present as the sole active principle.
5 An enteric dosage form as claimed in any one of Claims 1 to 4, wherein said acid or salt is present with another active principle selected from linoleic acid, gamma-linolenic acid, and/or dihomo-gamma-linolenic acid in free acid form or as a pharmaceutically acceptable salt thereof.
6 An enteric dosage form as claimed in any one of the preceding claims containing an antioxidant amount of gamma-tocopherol.
7 An enteric <RTI>aosage</RTI> torm as claimed in any one of the preceding claims which is an enterically coated tablet containing the said acid or salt in a microencapsulated form or <RTI>loaaed</RTI> on an absorbent.
8 An enteric dosage <RTI>form</RTI> as claimea in any one of Claims 1 to 6 which is an enterically coated capsule.
9 An enteric dosage form as claimed in Claim 8, wherein the capsule is a soft gelatine capsule.
10 An enteric <RTI>aosage</RTI> form as claimed in Claim 8, wherein the capsule is a hard gelatine capsule.
11 An enteric <RTI>dosage</RTI> form as claimed in any one of the preceding claims, wherein each unit dose contains 250 to 1000 mg of said omega-3 acid or salt.
12 An enteric dosage form as claimed in Claim 11, wherein each unit dose contains 400 to 800 mg of said omega-3 acid or salt.
13 An enteric dosage form substantially as hereinbefore described in the Example.
14 Ihe use of an enteric dosage form as <RTI>claimed</RTI> in any one of the preceding claims in the treatment or prophylaxis of thrombo-embolic conditions.
15 The use of an enteric dosage form as claimed in any one of Claims 1 to 13 for the treatment of rheumatoid arthritis.
16 The use of an enteric dosage form as claimed in any one of Claims 1 to 13 for the treatment of diabetes mellitus.
17 The use of an enteric dosage form as claimed in any one of Claims 1 to 13 for the treatment of migraine.
18 The use of an enteric dosage form as claimed in any one of Claims 1 to 13 for the treatment of psoriasis.
19 The use of an enteric dosage form as claimed in any one of Claims 1 to 13 for the treatment of cancer.
20 The use of an enteric dosage form as claimed in any one of Claims 1 to 13 for the treatment of hypercholesterolaemia.
21 The use of an enteric dosage form as claimed in any one of Claims 1 to 13 as a dietetic.
GB8824709A 1988-10-21 1988-10-21 Oral dosage forms of omega-3 polyunsaturated acids Withdrawn GB8824709D0 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB8824709A GB8824709D0 (en) 1988-10-21 1988-10-21 Oral dosage forms of omega-3 polyunsaturated acids

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB8824709A GB8824709D0 (en) 1988-10-21 1988-10-21 Oral dosage forms of omega-3 polyunsaturated acids
CA 2000881 CA2000881A1 (en) 1988-10-21 1989-10-17 Oral dosage forms of omega-3 polyunsaturated acids
PCT/GB1989/001251 WO1990004391A1 (en) 1988-10-21 1989-10-20 Oral dosage forms of omega-3 polyunsaturated acids

Publications (2)

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GB8824709D0 GB8824709D0 (en) 1988-11-30
GB2223943A true true GB2223943A (en) 1990-04-25

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CA (1) CA2000881A1 (en)
GB (1) GB8824709D0 (en)
WO (1) WO1990004391A1 (en)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0462003A1 (en) * 1990-06-13 1991-12-18 Université de Liège Microcapsules containing an oily liquid
GB2229363B (en) * 1989-03-20 1993-06-02 Michael John Tisdale Eicosapentaenoic acid
US5457130A (en) * 1989-03-20 1995-10-10 Cancer Research Campaign Technology Limited Eicosapentaenoic acid used to treat cachexia
GB2300807A (en) * 1995-05-15 1996-11-20 Tillotts Pharma Ag Oral dosage forms of omega-3 polyunsaturated acids for the treatment of inflammatory bowel disease
WO1996036329A1 (en) * 1995-05-15 1996-11-21 Tillotts Pharma Ag Treatment of inflammatory bowel disease using oral dosage forms of omega-3 polyunsaturated acids
WO1997021434A1 (en) * 1995-12-11 1997-06-19 Inholtra, Inc. Dietary regimen of nutritional supplements for relief of symptoms of arthritis
US5840715A (en) * 1995-12-11 1998-11-24 Inholtra Investment Holdings & Trading, N.V. Dietary regimen of nutritional supplements for relief of symptoms of arthritis
US6451771B1 (en) 1999-02-12 2002-09-17 Nutramax Laboratories, Inc. Use of anabolic agents anti-catabolic agents and antioxidant agents for protection treatment and repair of connective tissues in humans and animals
EP1407767A1 (en) * 2001-06-18 2004-04-14 Yamada, Sachico Pparg agonistic medicinal compositions
EP1450787A2 (en) * 2001-11-15 2004-09-01 Galileo Laboratories, Inc. Formulations and methods for treatment or amelioration of inflammatory conditions
WO2004078166A2 (en) * 2003-03-05 2004-09-16 Solvay Pharmaceuticals Gmbh Use of omega-3-fatty acids in the treatment of diabetic patients
US6797289B2 (en) 1998-02-13 2004-09-28 Nutramax Laboratories, Inc. Use of anabolic agents, anti-catabolic agents, antioxidant agents, and analgesics for protection, treatment and repair of connective tissues in humans and animals
EP1551382A2 (en) * 2002-09-27 2005-07-13 Martek Biosciences Corporation Prophylactic docosahexaenoic acid therapy for patients with subclinical inflammation
WO2006067498A1 (en) * 2004-12-24 2006-06-29 S.L.A. Pharma Ag Eicosapentaenoic acid for the treatment of cancer
WO2006122123A2 (en) * 2005-05-09 2006-11-16 Levin Bruce H Methods of alleviating disorders and their associated pain
US7601757B2 (en) 2003-09-05 2009-10-13 Abbott Laboratories Lipid system and methods of use
EP1755565B1 (en) * 2004-02-13 2010-02-17 Tillotts Pharma Ag Soft gelatin capsule comprising omega-3 polyunsaturated fatty acid
US8568803B2 (en) 1998-02-13 2013-10-29 Nutramax Laboratories, Inc. Use of anabolic agents, anti-catabolic agents, antioxidant agents and analgesics for protection, treatment and repair of connective tissues in humans and animals
US20150086625A1 (en) * 2008-12-31 2015-03-26 Nitromega Corp. Nutraceuticals containing nitro fatty acids
US9050309B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US9492545B2 (en) 2012-05-07 2016-11-15 Omthera Pharmaceuticals Inc. Compositions of statins and omega-3 fatty acids
US20170042947A1 (en) * 2014-04-25 2017-02-16 Yamada Bee Company, Inc. Unsaturated fatty acid absorption accelerator

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WO1992012711A1 (en) * 1991-01-24 1992-08-06 Martek Corporation Microbial oil mixtures and uses thereof
GB9901809D0 (en) 1999-01-27 1999-03-17 Scarista Limited Highly purified ethgyl epa and other epa derivatives for psychiatric and neurological disorderes
DE19930030B4 (en) * 1999-06-30 2004-02-19 Meduna Arzneimittel Gmbh CO-3-unsaturated fatty acids-containing oral dosage form
JP2009523414A (en) 2005-12-21 2009-06-25 ブルーディ、テクノロジー、ソシエダッド、リミターダBrudy Technology,S.L. dha to treat pathologies associated with oxidative cell damage, use of epa from epa or dha
KR20140007973A (en) 2009-02-10 2014-01-20 아마린 파마, 인크. Methods of treating hypertriglyceridemia
EP2424521A4 (en) 2009-04-29 2015-03-04 Amarin Pharmaceuticals Ie Ltd Pharmaceutical compositions comprising epa and a cardiovascular agent and methods of using the same
US20120100208A1 (en) 2009-04-29 2012-04-26 Amarin Pharma, Inc. Stable pharmaceutical composition and methods of using same
WO2010147994A1 (en) 2009-06-15 2010-12-23 Amarin Pharma, Inc. Compositions and methods for lowering triglycerides without raising ldl-c levels in a subject on concomitant statin therapy
US9827219B2 (en) 2012-01-06 2017-11-28 Amarin Pharmaceuticals Ireland Limited Compositions and methods for lowering levels of high-sensitivity C-reactive protein (HS-CRP) in a subject
WO2014005013A3 (en) 2012-06-29 2014-02-20 Amarin Pharmaceuticals Ireland Limited Methods of reducing the risk of a cardiovascular event in a subject on statin therapy
US9814733B2 (en) 2012-12-31 2017-11-14 A,arin Pharmaceuticals Ireland Limited Compositions comprising EPA and obeticholic acid and methods of use thereof
US9452151B2 (en) 2013-02-06 2016-09-27 Amarin Pharmaceuticals Ireland Limited Methods of reducing apolipoprotein C-III
US9624492B2 (en) 2013-02-13 2017-04-18 Amarin Pharmaceuticals Ireland Limited Compositions comprising eicosapentaenoic acid and mipomersen and methods of use thereof
US9662307B2 (en) 2013-02-19 2017-05-30 The Regents Of The University Of Colorado Compositions comprising eicosapentaenoic acid and a hydroxyl compound and methods of use thereof
US9283201B2 (en) 2013-03-14 2016-03-15 Amarin Pharmaceuticals Ireland Limited Compositions and methods for treating or preventing obesity in a subject in need thereof
US9585859B2 (en) 2013-10-10 2017-03-07 Amarin Pharmaceuticals Ireland Limited Compositions and methods for lowering triglycerides without raising LDL-C levels in a subject on concomitant statin therapy

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Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2229363B (en) * 1989-03-20 1993-06-02 Michael John Tisdale Eicosapentaenoic acid
US5457130A (en) * 1989-03-20 1995-10-10 Cancer Research Campaign Technology Limited Eicosapentaenoic acid used to treat cachexia
EP0462003A1 (en) * 1990-06-13 1991-12-18 Université de Liège Microcapsules containing an oily liquid
FR2663222A1 (en) * 1990-06-13 1991-12-20 Medgenix Group Sa Microcapsule oily liquid.
US5456985A (en) * 1990-06-13 1995-10-10 Zgoulli; Slim Microcapsules of oily liquid
WO1996036329A1 (en) * 1995-05-15 1996-11-21 Tillotts Pharma Ag Treatment of inflammatory bowel disease using oral dosage forms of omega-3 polyunsaturated acids
GB2300807A (en) * 1995-05-15 1996-11-20 Tillotts Pharma Ag Oral dosage forms of omega-3 polyunsaturated acids for the treatment of inflammatory bowel disease
US5948818A (en) * 1995-05-15 1999-09-07 Tillotts Pharma Ag Treatment of inflammatory bowel disease using oral dosage forms of omega-3 polyunsaturated acids
US5792795A (en) * 1995-05-15 1998-08-11 Tillotts Pharma Ag Treatment of inflammatory bowel disease using oral dosage forms of omega-3 polyunsaturated acids
GB2300807B (en) * 1995-05-15 1999-08-18 Tillotts Pharma Ag Oral dosage forms of omega-3 polynunsaturated acids for the treatment of inflammatory bowel disease
US5840715A (en) * 1995-12-11 1998-11-24 Inholtra Investment Holdings & Trading, N.V. Dietary regimen of nutritional supplements for relief of symptoms of arthritis
WO1997021434A1 (en) * 1995-12-11 1997-06-19 Inholtra, Inc. Dietary regimen of nutritional supplements for relief of symptoms of arthritis
US6797289B2 (en) 1998-02-13 2004-09-28 Nutramax Laboratories, Inc. Use of anabolic agents, anti-catabolic agents, antioxidant agents, and analgesics for protection, treatment and repair of connective tissues in humans and animals
US8568803B2 (en) 1998-02-13 2013-10-29 Nutramax Laboratories, Inc. Use of anabolic agents, anti-catabolic agents, antioxidant agents and analgesics for protection, treatment and repair of connective tissues in humans and animals
US6451771B1 (en) 1999-02-12 2002-09-17 Nutramax Laboratories, Inc. Use of anabolic agents anti-catabolic agents and antioxidant agents for protection treatment and repair of connective tissues in humans and animals
EP1407767A1 (en) * 2001-06-18 2004-04-14 Yamada, Sachico Pparg agonistic medicinal compositions
EP1407767A4 (en) * 2001-06-18 2007-01-24 Yamada Sachiko Pparg agonistic medicinal compositions
EP1450787A2 (en) * 2001-11-15 2004-09-01 Galileo Laboratories, Inc. Formulations and methods for treatment or amelioration of inflammatory conditions
EP1450787A4 (en) * 2001-11-15 2006-01-25 Galileo Pharmaceuticals Inc Formulations and methods for treatment or amelioration of inflammatory conditions
EP1551382A2 (en) * 2002-09-27 2005-07-13 Martek Biosciences Corporation Prophylactic docosahexaenoic acid therapy for patients with subclinical inflammation
EP1551382A4 (en) * 2002-09-27 2007-01-24 Martek Biosciences Corp Prophylactic docosahexaenoic acid therapy for patients with subclinical inflammation
WO2004078166A3 (en) * 2003-03-05 2004-10-28 Rainer Oelze Use of omega-3-fatty acids in the treatment of diabetic patients
WO2004078166A2 (en) * 2003-03-05 2004-09-16 Solvay Pharmaceuticals Gmbh Use of omega-3-fatty acids in the treatment of diabetic patients
US7759507B2 (en) 2003-09-05 2010-07-20 Abbott Laboratories Lipid system and methods of use
US7601757B2 (en) 2003-09-05 2009-10-13 Abbott Laboratories Lipid system and methods of use
US9012501B2 (en) 2004-02-13 2015-04-21 Chrysalis Pharma Ag Type A gelatin capsule containing PUFA in free acid form
EP1755565B1 (en) * 2004-02-13 2010-02-17 Tillotts Pharma Ag Soft gelatin capsule comprising omega-3 polyunsaturated fatty acid
US9132112B2 (en) 2004-02-13 2015-09-15 Chysalis Pharma Ag Type A gelatin capsule containing PUFA in free acid form
CN1929824B (en) 2004-02-13 2011-03-23 狄洛特医药有限公司 Soft gelatin capsule comprising omega-3-polyunsaturated fatty acid
US7960370B2 (en) 2004-02-13 2011-06-14 Jean-Pierre Sachetto Type A gelatin capsule containing PUFA in free acid form
JP2012149073A (en) * 2004-02-13 2012-08-09 Tillotts Pharma Ag Pharmaceutical composition
US8383678B2 (en) 2004-02-13 2013-02-26 Chrysalis Pharma Ag Type a gelatin capsule containing PUFA in free acid form
WO2006067498A1 (en) * 2004-12-24 2006-06-29 S.L.A. Pharma Ag Eicosapentaenoic acid for the treatment of cancer
WO2006122123A3 (en) * 2005-05-09 2007-06-07 Bruce H Levin Methods of alleviating disorders and their associated pain
WO2006122123A2 (en) * 2005-05-09 2006-11-16 Levin Bruce H Methods of alleviating disorders and their associated pain
US20150086625A1 (en) * 2008-12-31 2015-03-26 Nitromega Corp. Nutraceuticals containing nitro fatty acids
US9050309B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US9050308B2 (en) 2012-01-06 2015-06-09 Omthera Pharmaceuticals, Inc. DPA-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form
US9492545B2 (en) 2012-05-07 2016-11-15 Omthera Pharmaceuticals Inc. Compositions of statins and omega-3 fatty acids
US20170042947A1 (en) * 2014-04-25 2017-02-16 Yamada Bee Company, Inc. Unsaturated fatty acid absorption accelerator

Also Published As

Publication number Publication date Type
CA2000881A1 (en) 1990-04-21 application
GB8824709D0 (en) 1988-11-30 grant
WO1990004391A1 (en) 1990-05-03 application

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