WO2001019330A1 - Pharmaceutical and/or cosmetical compositions - Google Patents
Pharmaceutical and/or cosmetical compositions Download PDFInfo
- Publication number
- WO2001019330A1 WO2001019330A1 PCT/EP2000/008741 EP0008741W WO0119330A1 WO 2001019330 A1 WO2001019330 A1 WO 2001019330A1 EP 0008741 W EP0008741 W EP 0008741W WO 0119330 A1 WO0119330 A1 WO 0119330A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pantothenic acid
- derivatives
- pharmaceutical
- glycine
- skin
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/673—Vitamin B group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Definitions
- the present invention relates to pharmaceutical and/or cosmetical compositions and, more precisely, to compositions for blocking the histamine release by the mastocytes.
- the degranulation of the cutaneous mastocytes leads to the release of several mediators, like for instance the histamine which is responsible for the occurrence of different reactions such as pruritus.
- the histamine release can be modulated by several substances which can either amplify or inhibit it, wherein the inhibitors can be used as active compounds in medicaments.
- the stimulus responsible for the degranulation of the mastocytes is due to a modification of the mastocyte membrane structure by a bipolar antigen fixed on two IgE which, on their turn, are unspecifically attached to the cell membrane by their Fc extremities.
- the stimuli maybe in fact of different nature, both chemical and physical, and may involve the presence of a neurotransmitter such as the substance P.
- This substance present naturally in the mammal body, is capable of initiating the degranulation process of the mastocytes.
- a pruritus can be therefore treated in different ways, e.g. by blocking the message transmission from the central nervous system, by blocking the stimulus and/or by inhibiting the degranulation process.
- Pantothenic acid which is also known as D(+) N-(2,4-dihydroxy-3,3-dimethylbutyryl) ⁇ - alanine, is a member of the B complex vitamins and is sometimes referred to as vitamin B 5 .
- Pantothenic acid plays a key role in cellular metabolism, as after incorporation into coenzyme A (CoA), it participates in the synthesis of fatty acids, cholesterol and sterols. Through its participation in the Krebs cycle, coenzyme CoA is also instrumental in the generation of energy by the cells. Pantothenic acid is hence essential for epithelial regeneration and development in the event of damage to the skin when a high rate of lipids and cellular renewal is needed. Dexpanthenol, the alcohol of the pantothenic acid, is well absorbed by the skin. After penetration in the skin it is rapidly transformed into pantothenic acid. Dexpanthenol has therefore been used for many years in topical products such as ointments and creams.
- compositions containing pantothenic acid and/or its derivatives can be used for treating prurigineous conditions. It has been observed that pantothenic acid and/or its derivatives inhibit the degranulation process of the mastocytes, thus diminishing the amount of mediators released into the extra- cellular environment. Pantothenic acid and/or its derivatives can be therefore used for all dermatological disorders which involve the degranulation process of the mastocytes, such as atopic dermatitis, psoriasis, contact eczema, skin allergies, skin inflammation due to insect bites, skin allergies, senile pruritus, etc.
- the pantothenic acid and/or its derivatives are used in a pharmaceutical and/or cosmetical composition in an amount varying between 0,1 and 10% of its total weight and, preferably, in an amount varying between 2 and 5% of the total weight of the pharmaceutical and/or cosmetical composition.
- pantothenic acid any pharmaceutically and/or cosmetically acceptable derivative of pantothenic acid can be used in the compositions of the present invention.
- examples include alcohols, aldehydes, alcohol esters, acid esters and the like.
- the preferred derivative of pantothenic acid is pantothenyl alcohol (panthenol), particularly the D(+) of pantothenyl alcohol which is more commonly known as dexpanthenol.
- pantothenyl triacetate can be chosen.
- the present invention relates also to the use of pantothenic acid and/or its derivatives for the manufacture of topically applicable pharmaceutical and/or cosmetical compositions for treating dermatological disorders which involve the degranulation process of the mastocytes, such as atopic dermatitis, psoriasis, contact eczema, skin allergies, skin inflammation due to insect bites, skin allergies, senile pruritus, etc.
- the pantothenic acid and/or its derivatives are present in an amount varying between 0,1 and 10% of the total weight of the pharmaceutical and/or cosmetical composition and, more preferably, in an amount varying between 2 and 5% of the total weight of the pharmaceutical and/or cosmetical composition.
- Another aspect of the present invention relates to pharmaceutical and/or cosmetical compositions comprising pantothenic acid and/or its derivatives, glycine and pharmaceutically and/or cosmetically acceptable additives.
- Glycine is an amino-acid naturally occurring in most animal species. It inhibits the histamine release by mastocytes.
- the effect of the glycine on the mastocyte degranulation is described, for instance, in M. Paubert-Braquet, G. Lefran ⁇ ois, S. Picquot, D. Rod, Therapeutique, 95, 1992, 2.
- An inhibition effect on the degranulation process of the mastocytes has been observed, wherein a decrease in the amount of mediators released into the extra-cellular environment (e.g. histamine) is observed.
- the synergic effect obtained by mixing the above compounds together lead to several important advantages. For the same effect, it is possible to reduce the concentrations of the active compounds, thus decreasing the risk of intolerance for the patients.
- compositions according to the present invention are therefore more tolerable and more competitive than the conventional ones.
- the ratio between the pantothenic acid and/or its derivatives and the glycine varies between 0.13 and 13.3 wt/wt.
- a further aspect of the present invention is related to the use of a mixture of pantothenic acid and/or its derivatives and glycine for the manufacture of a medicament for treating dermatological disorders which involve the degranulation process of the mastocytes, such as atopic dermatitis, psoriasis, contact eczema, skin allergies, skin inflammation due to insect bites, skin allergies, senile pruritus, etc.
- pantothenic acid and/or its derivatives and the glycine are present in the mixture in a ratio varying between 0.13 and 13.3 wt/wt.
- Pantothenic acid and/or its derivatives and the mixtures of pantothenic acid and/or its derivatives and glycine can be administered orally or be applied topically to the skin of a mammal at the site of the disorder.
- Pantothenic acid and/or its derivatives and the mixtures of pantothenic acid and/or its derivatives and glycine can be administered orally in the form of tablets, coated tablets, dragees, hard and soft gelatine capsules, solutions, emulsions or suspensions.
- the active compounds can be processed with pharmaceutically inert, inorganic or organic excipients, such as lactose, corn starch or derivatives thereof, talc, stearic acid or its salts.
- Suitable excipients for soft gelatine capsules are e.g. vegetable oils, waxes, fats, semi-solid and liquid polyols etc.
- Suitable excipients for the manufacture of solutions and syrups are e.g. water, polyols, saccharose, invert sugar, glucose etc.
- the pharmaceutical and/or cosmetical compositions can contain preservatives, solubilizers, stabilizers, wetting agents, emulsifiers, sweeteners, colorants, flavorants, salts for varying the osmotic pressure, buffers, masking agents or antioxidants. They can also contain still other therapeuticaUy valuable substances, such as further vitamins, minerals, sun filters, phytotherapeutic extracts, etc.
- Topical dosage forms provided by the invention generally contain 0.1 to 10 weight percent of active compound, based on the total weight of the dosage form. However, higher or lower concentrations can also be present depending on the dosage form which is used.
- the topical preparations of the present invention can be applied in an amount and under a time schedule varying with the needs of the patient.
- topical as used in the present specification relates to the use of the above active compounds, which are processed with a suitable carrier material and which is applied to the skin or mucous membrane, so that it can display local activity.
- the topical forms embrace pharmaceutical and/or cosmetical dosage forms which are suitable for external use, so that a direct contact with the skin results.
- the topical dosage forms embrace gels, creams, lotions, salves, powders, aerosols and other conventional forms which are suitable for the direct application of products on the skin or mucous membrane. These dosage forms can be manufactured by mixing the above compounds with known carrier materials which are suitable for topical use.
- Salves and creams contain oily, absorbent, water-soluble and/or emulsifying carrier materials such as vaseline, paraffin oil, propylene glycol, cetylalcohol, glycerine monostearate, alkyl-branched fatty acids and the like.
- Lotions are liquid preparations and can vary from simple solutions to aqueous or aqueous/alcoholic preparations which contain the substances in finely divided form.
- the preparations contain suspended or dispersing substances such as, for example, sodium carboxymethylcellulose which suspend or disperse the active substance in a carrier prepared from water, alcohol, glycerine and the like.
- Gels are semi-solid preparations which are obtained by gelling a solution or suspension of the active substance in a carrier material.
- the carrier materials which can be hydrophilic or hydrophobic, are gelled using a gelling agent in form of polymers of biological, natural or synthetical origin.
- Aerosols are solutions or suspensions of the active substance in a carrier material which are applied using spray generators.
- carrier material are, for example, trichloromonofluoromethane, trichlorodifluoromethane, volatile silicones, nitrogen, etc..
- Spays are solutions suspensions or powders of the active substance in a carrier material which are applied using mechanical pums.
- compositions according to the present invention are used by applying an amount of the active compounds sufficient to provide a therapeutic and/or cosmetic effect to the skin to be treated.
- This application can be effected in the usual manner by rubbing, spraying or by a plaster.
- topical compositions are usually applied in an amount to provide from 0.1 to 5 mg of active ingredient per cm of the skin per day.
- Glycine and calcium pantothenate were provided by ROCHE and they were conserved at 4°C until their use.
- Substance P was provided by SIGMA and the analytic reagents were provided by SIGMA, MERCK, BDH, ALDRICH, FLUKA or CARLO ERBA unless otherwise specified.
- Tests were carried out on peritoneal mastocytes of rat stimulated by the substance P ( lO ⁇ M), or on human skin tissue.
- Peritoneal mastocytes of rat were incubated with the test products and the substance P for 2 minutes at 37°C in the following medium: sodium phosphate buffer 4 mM; potassium phosphate buffer 2.7 mM; NaCl 0.145 M; KC1 2.7 mM; CaCl 2 0.9 mM; BSA (bovine serum albumin) 0.175% (w/v).
- OPT ortho-phthalaldehyde
- Table 2 Inhibition in Peritoneal mastocytes of rat.
- Value 100 refers to the amount of histamine released by the substance P in absence of Ca-pantothenate and/or glycine, while value 0 refers to the release of histamine in normal conditions, i.e. in the absence of histamine release inducing agents. Negative values represent histamine concentrations which are lower than those observable at normal conditions.
- the skin tissue assay system was prepared from normal adult skin collected after an abdominal plastic surgery.
- the subject was a 68 years old woman (subject M1085).
- the skin tissue specimen was rinsed in Krebs bicarbonate solution consisting of: NaCl 118 mM; KC1 5.4 mM; NaH 2 P0 4 1 mM; MgSO 4 1.2 mM, CaCl 2 1.9 mM; NaHC0 3 25 mM and D- glucose 11.1 mM.
- Skin discs of about 8 mm of diameter were performed. Skin discs were cultured in RPMI 1640 medium supplemented with penicillin ( 100 Ul/ml), streptomycin ( 110 ⁇ g/ml) and 2 M glutamine. Skin discs were maintained at 37°C in a humidified incubator under a 5% C0 2 /95% air atmosphere. Test products were incubated with the human skin discs and 100 ⁇ M of substance P for 2 hours at 37°C.
- histamine released by the human skin discs was quantified by ELISA (IMMUNOTECH). The results were expressed as pmoles of histamine released per gram of skin. Data groups (control and treated groups) were compared using a one-way analysis of variance (ANOVA 1, p ⁇ 0.05), following by a Dunnett's test (p ⁇ 0.05).
- Value 100 refers to the amount of histamine released by the substance P in absence of Ca-pantothenate and/or glycine, while value 0 refers to the release of histamine in normal conditions, i.e. in the absence of histamine release inducing agents. Negative values represent histamine concentrations which are lower than those observable at normal conditions.
- Ointment containing dexpanthenol and glycine Ointment containing dexpanthenol and glycine.
- the topical composition is prepared by combining the following components utilizing conventional techniques:
- the topical composition is prepared by combining the following components utilizing conventional techniques:
- the oral composition is prepared by combining the following components utilizing conventional mixing techniques:
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT00965936T ATE289799T1 (en) | 1999-09-15 | 2000-09-07 | PHARMACEUTICAL AND/OR COSMETIC COMPOSITIONS |
ES00965936T ES2237457T3 (en) | 1999-09-15 | 2000-09-07 | PHARMACEUTICAL AND / OR COSMETIC COMPOSITIONS. |
AU76510/00A AU7651000A (en) | 1999-09-15 | 2000-09-07 | Pharmaceutical and/or cosmetical compositions |
EP00965936A EP1216021B1 (en) | 1999-09-15 | 2000-09-07 | Pharmaceutical and/or cosmetical compositions |
PL356157A PL200231B1 (en) | 1999-09-15 | 2000-09-07 | Pharmaceutical and/or cosmetical compositions |
SI200030664T SI1216021T1 (en) | 1999-09-15 | 2000-09-07 | |
DK00965936T DK1216021T3 (en) | 1999-09-15 | 2000-09-07 | Pharmaceutical and / or cosmetic preparations |
DE60018438T DE60018438T2 (en) | 1999-09-15 | 2000-09-07 | PHARMACEUTICAL AND / OR COSMETIC COMPOSITIONS |
NO20021241A NO20021241D0 (en) | 1999-09-15 | 2002-03-13 | Pharmaceutical and / or cosmetic mixtures |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP99118285 | 1999-09-15 | ||
EP99118285.8 | 1999-09-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001019330A1 true WO2001019330A1 (en) | 2001-03-22 |
Family
ID=8239005
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2000/008741 WO2001019330A1 (en) | 1999-09-15 | 2000-09-07 | Pharmaceutical and/or cosmetical compositions |
Country Status (15)
Country | Link |
---|---|
US (1) | US6410037B1 (en) |
EP (1) | EP1216021B1 (en) |
AR (1) | AR025602A1 (en) |
AT (1) | ATE289799T1 (en) |
AU (1) | AU7651000A (en) |
CZ (1) | CZ20021279A3 (en) |
DE (1) | DE60018438T2 (en) |
DK (1) | DK1216021T3 (en) |
ES (1) | ES2237457T3 (en) |
NO (1) | NO20021241D0 (en) |
PL (1) | PL200231B1 (en) |
PT (1) | PT1216021E (en) |
SI (1) | SI1216021T1 (en) |
TR (1) | TR200200666T2 (en) |
WO (1) | WO2001019330A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004026295A2 (en) * | 2002-09-17 | 2004-04-01 | Phenion Gmbh & Co. Kg | Use of skin-protecting substances |
WO2008148573A2 (en) * | 2007-06-08 | 2008-12-11 | Bayer Consumer Care Ag | Medicament comprising an active substance combination containing pantothenic acid or the derivatives thereof for the treatment of allergy symptoms |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005060342A2 (en) * | 2003-12-19 | 2005-07-07 | Omega Bio-Pharma International Ltd. | Cysteamine compounds for treating allergy |
JP4301224B2 (en) * | 2005-02-16 | 2009-07-22 | トヨタ自動車株式会社 | Automobile and control method thereof |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4721705A (en) * | 1983-09-26 | 1988-01-26 | Chemish Adviesbureau Drs. J.C.P. Schreuder B.V. | Skin treatment compositions |
WO1993021899A1 (en) * | 1992-05-05 | 1993-11-11 | The Procter & Gamble Company | Acne treating composition |
US5304574A (en) * | 1991-02-11 | 1994-04-19 | Leung Lit Hung | Methods of treatment of clinical conditions using pantothenic acid |
EP0687467A2 (en) * | 1994-06-14 | 1995-12-20 | Beiersdorf Aktiengesellschaft | Cosmetic and dermatological combinations containing glycerylalkylethers as active ingredients |
DE19531893A1 (en) * | 1995-08-30 | 1997-03-06 | Bayer Ag | Itching, cosmetic and / or pharmaceutical compositions |
DE19537509A1 (en) * | 1995-09-27 | 1997-04-10 | Egsto Pharm Pharmazeutische Pr | Prods. for treating irritated skin |
US5827523A (en) * | 1997-04-29 | 1998-10-27 | Holland; Dennis A. | Universal topical antiseptic first aid spray |
DE19800982A1 (en) * | 1998-01-14 | 1999-07-15 | Foerster Karl Heinz | Ointment containing ethereal oil, liposomes and vitamins, for treating neurodermatitis, psoriasis and eczema |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5425954A (en) * | 1993-09-30 | 1995-06-20 | Curafas Incorporated | Topical amino acid - vitamin complex compositions for pharmaceutical and cosmetic use |
DE19520237A1 (en) * | 1995-06-02 | 1996-12-05 | Beiersdorf Ag | Cosmetic or dermatological preparations containing oligomers or polymers of alpha-hydroxycarboxylic acids |
DE19618809C1 (en) * | 1996-05-10 | 1997-12-11 | Goldwell Gmbh | Skin or hair cosmetic used in skin moisturisers |
DE19739447A1 (en) * | 1997-09-02 | 1999-03-04 | Coty Bv | Emulsifier-free, clear sunscreen gel |
-
2000
- 2000-09-07 TR TR2002/00666T patent/TR200200666T2/en unknown
- 2000-09-07 SI SI200030664T patent/SI1216021T1/xx unknown
- 2000-09-07 PT PT00965936T patent/PT1216021E/en unknown
- 2000-09-07 AT AT00965936T patent/ATE289799T1/en not_active IP Right Cessation
- 2000-09-07 PL PL356157A patent/PL200231B1/en not_active IP Right Cessation
- 2000-09-07 AU AU76510/00A patent/AU7651000A/en not_active Abandoned
- 2000-09-07 CZ CZ20021279A patent/CZ20021279A3/en unknown
- 2000-09-07 DK DK00965936T patent/DK1216021T3/en active
- 2000-09-07 DE DE60018438T patent/DE60018438T2/en not_active Expired - Lifetime
- 2000-09-07 ES ES00965936T patent/ES2237457T3/en not_active Expired - Lifetime
- 2000-09-07 WO PCT/EP2000/008741 patent/WO2001019330A1/en active IP Right Grant
- 2000-09-07 EP EP00965936A patent/EP1216021B1/en not_active Expired - Lifetime
- 2000-09-08 AR ARP000104710A patent/AR025602A1/en unknown
- 2000-09-11 US US09/658,896 patent/US6410037B1/en not_active Expired - Lifetime
-
2002
- 2002-03-13 NO NO20021241A patent/NO20021241D0/en not_active Application Discontinuation
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4721705A (en) * | 1983-09-26 | 1988-01-26 | Chemish Adviesbureau Drs. J.C.P. Schreuder B.V. | Skin treatment compositions |
US5304574A (en) * | 1991-02-11 | 1994-04-19 | Leung Lit Hung | Methods of treatment of clinical conditions using pantothenic acid |
WO1993021899A1 (en) * | 1992-05-05 | 1993-11-11 | The Procter & Gamble Company | Acne treating composition |
EP0687467A2 (en) * | 1994-06-14 | 1995-12-20 | Beiersdorf Aktiengesellschaft | Cosmetic and dermatological combinations containing glycerylalkylethers as active ingredients |
DE19531893A1 (en) * | 1995-08-30 | 1997-03-06 | Bayer Ag | Itching, cosmetic and / or pharmaceutical compositions |
DE19537509A1 (en) * | 1995-09-27 | 1997-04-10 | Egsto Pharm Pharmazeutische Pr | Prods. for treating irritated skin |
US5827523A (en) * | 1997-04-29 | 1998-10-27 | Holland; Dennis A. | Universal topical antiseptic first aid spray |
DE19800982A1 (en) * | 1998-01-14 | 1999-07-15 | Foerster Karl Heinz | Ointment containing ethereal oil, liposomes and vitamins, for treating neurodermatitis, psoriasis and eczema |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004026295A2 (en) * | 2002-09-17 | 2004-04-01 | Phenion Gmbh & Co. Kg | Use of skin-protecting substances |
WO2004026295A3 (en) * | 2002-09-17 | 2004-11-11 | Phenion Gmbh & Co Kg | Use of skin-protecting substances |
WO2008148573A2 (en) * | 2007-06-08 | 2008-12-11 | Bayer Consumer Care Ag | Medicament comprising an active substance combination containing pantothenic acid or the derivatives thereof for the treatment of allergy symptoms |
WO2008148573A3 (en) * | 2007-06-08 | 2009-05-07 | Bayer Consumer Care Ag | Medicament comprising an active substance combination containing pantothenic acid or the derivatives thereof for the treatment of allergy symptoms |
Also Published As
Publication number | Publication date |
---|---|
EP1216021A1 (en) | 2002-06-26 |
PL356157A1 (en) | 2004-06-14 |
PT1216021E (en) | 2005-07-29 |
CZ20021279A3 (en) | 2003-05-14 |
NO20021241L (en) | 2002-03-13 |
DK1216021T3 (en) | 2005-05-23 |
AU7651000A (en) | 2001-04-17 |
NO20021241D0 (en) | 2002-03-13 |
US6410037B1 (en) | 2002-06-25 |
SI1216021T1 (en) | 2005-08-31 |
ES2237457T3 (en) | 2005-08-01 |
PL200231B1 (en) | 2008-12-31 |
EP1216021B1 (en) | 2005-03-02 |
AR025602A1 (en) | 2002-12-04 |
ATE289799T1 (en) | 2005-03-15 |
DE60018438T2 (en) | 2006-03-16 |
DE60018438D1 (en) | 2005-04-07 |
TR200200666T2 (en) | 2002-06-21 |
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