WO1997012608A1 - Agent anti-inflammatoire externe - Google Patents
Agent anti-inflammatoire externe Download PDFInfo
- Publication number
- WO1997012608A1 WO1997012608A1 PCT/JP1996/000849 JP9600849W WO9712608A1 WO 1997012608 A1 WO1997012608 A1 WO 1997012608A1 JP 9600849 W JP9600849 W JP 9600849W WO 9712608 A1 WO9712608 A1 WO 9712608A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- inflammatory agent
- weight
- base
- agent according
- topical anti
- Prior art date
Links
Classifications
-
- 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
- A61K31/63—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Definitions
- Topical anti-inflammatory agent Topical anti-inflammatory agent
- the present invention relates to an anti-inflammatory agent for external use containing dimetholide as an active ingredient, more specifically, a dimetholide as an active ingredient dispersed in a base ingredient.
- the present invention relates to a formulated external anti-inflammatory agent and a method for producing the same.
- Non-steroidal anti-inflammatory drugs may cause gastrointestinal tract disorders when taken orally, but avoid them. For this reason, various studies have been made to develop it as an external preparation, and several products have already been clinically used. However, the non-steroidal topical anti-inflammatory agents used up to now were not effective enough in clinical trials even though they were effective in basic tests.
- Nimesulide Nimesulide: 4-Nitro 1-2-Phenoximine
- This compound was synthesized by Lyca in the United States and later developed by Helsin of Switzerland as an oral formulation in a single mouthpiece. Was done. It is known to selectively inhibit PGE 2 (C0X2), unlike conventional acid anti-inflammatory drugs, and thus these two methods are clinically available. It is a new type of drug that is expected to be effective.
- Nimesulide has a pharmacological effect equal to or better than that of indomethacin, which is considered to be a potent anti-inflammatory agent. It is thought that when topically applied as an external preparation, it has some insurmountable difficulties. Immediately, penimide is very poorly soluble and hardly soluble in water or various organic solvents. 2 In order to dissolve it, it is necessary to mix a solvent with strong dissolving power, but in such a case, it will cause skin irritation, rough skin, itching or redness. There is a problem.
- An object of the present invention is to obtain a topical anti-inflammatory agent for topical use, which is an external preparation with excellent absorbability and which has no problems with coloring, skin safety, etc. is there .
- the present inventors have conducted intensive studies in consideration of the drawbacks of the above-mentioned two-method as a topical drug. As a result, the present inventors have found that two-method can be formulated in a dispersed state in a base component. As a result, they have found that the above problems can be solved at once, and have completed the present invention.
- the two compounds when blended in a dispersed state in the base component, they surprisingly show a pharmacological effect equal to or higher than that of the formulation formulated in a soluble form, and even dissolve Because the formulation of the preparation is reduced, skin safety is improved, and unlike the complete dissolution type preparation, the coloration of the preparation is reduced, making it an external preparation. It was helpful to be able to solve all of the above problems.
- the active ingredient in the base component containing an oily substance, a nonionic surfactant, a basic substance, water and / or an absorption enhancer, the active ingredient, Nimes
- the purpose of the present invention is achieved by compounding the lid in a dispersed state.
- nimesulide which is an active ingredient, in addition to a hydrophilic polymer or white cerin as a base, is added in the form of fine particles. 0.1 to 5% by weight to make an external preparation such as a cream or a softening agent.
- Nimesulide, an active ingredient can be used in any form as long as it exhibits a dispersed state in the base ingredient, but it should be dispersed.
- the average particle size is preferably 0.01 m or more in view of the easiness of pulverization of the particles and the economical efficiency.
- the transdermal absorbability and the tactile sensation (gritty feeling) during application It should be less than 75 ⁇ m and should pass immediately through a 200 mesh hoof, more preferably from 0.5 to 50 im, and more preferably from l ⁇ 30 ⁇ m.
- an oil phase in which an oil component is dissolved by heating and an aqueous phase in which a water-soluble component is dissolved are mixed and stirred.
- the finely divided nimesulide is added, and the mixture is further stirred and cooled to produce.
- Ointments are also manufactured by stirring and cooling the oil component that has been heated and dissolved, adding finely divided two-methride, and further stirring and cooling.
- the pH of the preparation is preferably adjusted to 4 to 8 from the viewpoints of skin irritation and transdermal absorption, and more preferably adjusted to 5 to 7. It is.
- Examples of the base for preparing the topical anti-inflammatory agent of the present invention include a hydrophilic polymer, an oily substance, a nonionic surfactant, a basic substance, and water.
- a hydrophilic polymer Manufactured from so-called gel-like creams, higher alcohols, hydrocarbons, fatty acid esters, polyhydric alcohols, bases, preservatives and water.
- Panishing type cream white petrolatum, surfactant, high-grade alcohol, hydrocarbon, fatty acid ester, polyhydric alcohol, protection Manufactured from preservatives, water, etc.
- the formulation of the cream was 0.2 to 3% by weight of a hydrophilic polymer, 2 to 20% by weight of an oily substance, and 0.5 to 7% by weight of a nonionic surfactant. / 0, basic substance 0.15 to 5% by weight, water 50 to 90% by weight, two so-called gel-like cream bases 0.1 to 5 Formulations containing 0.1% by weight are most suitable from the viewpoint of transdermal absorption.
- the formulation of the ointment is as follows: 35-80% by weight of white-colored serine, 2,20% by weight of an oily substance, and 0.5-7% by weight of a nonionic surfactant.
- the most preferred is a preparation obtained by mixing 0.1% to 5% by weight of two methrides with Nasaru vaseline ointment.
- the base component of the present invention will be described more specifically.
- the hydrophilic polymer there may be used a non-reactive polymer (available from BF Goodrich Co., Ltd., a product available from Wako Pure Chemical Industries, Ltd.). And Ibizo Co., Ltd., 1 ⁇ 4, 105, etc.), hydroxypropyl cellulose (HPC-L, manufactured by Nihon Soda Co., Ltd.) HPC-1M, etc., and polyoxypropylene polyblock block polymers (such as BASF's Noretrol F68). What is it?
- HPC-L hydroxypropyl cellulose
- HPC-1M hydroxypropyl cellulose
- polyoxypropylene polyblock block polymers such as BASF's Noretrol F68. What is it?
- These hydrophilic polymers are used alone or in combination of two or more, and when the viscosity and stickiness of the cream are considered, 0.2 to 3% by weight is used. Preferably, more preferably 0.5 to 2%
- Oils1 Raw materials include diisobromovinylate, diisopropyl benzoate, diisopropyl cenosate, dimethyl sebacate, and medium-chain fats.
- Fatty acid esters such as acid triglycerides, medium-chain fatty acid propylene glycol, isopropyl myristate, etc.
- stearyl Fatty acids such as carboxylic acid, oleic acid, myristinic acid, etc., cetanol, stearyl real alcohol, set stearyl alcohol, etc.
- High-quality alcohols such as Nore, Ole-Nore-A-No-Re, and He-N-No-Re-A-No-Rele are available in white color, serine, liquid paraffin, and silk.
- Hydrocarbons such as lanthanides are plant oils such as olive oil, jojoba oil, castor oil, and other black and white mittens and benzyl alcohol. And the like.
- the amount of these oily substances may be such as cream elongation, transdermal absorbability, stickiness, bracing, or liquid separation.
- the content is 2 to 20% by weight, preferably 5 to 15% by weight.
- 2 to 20% by weight, preferably 3 to 7% by weight is blended.
- surfactant examples include solvitan fatty acid esters such as sonorebitan monostearate, solvita sesquistearate, and the like.
- Glyceryl fatty acid esters polyoxyethylenes such as glyceryl monoester, diglyceryl monoester, etc. (20) Sorbitan monostearate, polyxylene (20) Sorbitan monosoleate, etc.
- Tylensorbitan fatty acid ester polyoxyethylene (10) monostearate, polyoxyethylene (10) monola Polyethylene glycols such as wool, fatty acid esters, polyoxyethylene (9) ⁇ The Shi et Ji Le emissions (23) etc.
- Nonynolephenyl ethers and polyoxyethylene Polyoxyethylene, such as len (10) octyl vinyl ether, polyalkyl ether, and polyoxyethylene (10) Hardened castor oil, polyoxyethylene (60) Polyoxyethylene, such as hardened castor oil, and hardened castor oil. It is. These surfactants may be used alone or in combination of two or more, and may be used in an amount of 0.5 to 7% by weight, preferably 1 to 5% by weight.
- Examples of the basic substance include calcium hydroxide, sodium hydroxide, sodium hydroxide, tria-norenoamine, diisopropanolamine, and molybdenum.
- Inorganic or organic bases such as ethanol, are exemplified, but organic bases are preferred from the viewpoint of transdermal absorption.
- These basic substances are incorporated in an amount of 0.01 to 5% by weight, preferably 0.1 to 2% by weight.
- an absorption enhancer is incorporated into the above-mentioned preparations for the purpose of increasing the transdermal absorption of dimethride according to the type of the preparation.
- examples include organic bases, crotamiton, medium-chain fatty acid esters, 1-menthols, pengino-real alcohols, and the like. It is.
- the organic base forms a salt with the dimethride and becomes water soluble, facilitating release of the dimethride from the base.
- Examples of the organic base include diisopropanolenomine, megnolenin, triethanol monooleamine, and 1.1 (2-hydroxyethyl).
- the amount of the absorption enhancer is from 0.1 to 20% by weight, preferably from 0.2 to 10% by weight, alone or in combination of two or more.
- the above-mentioned basic substance or the organic base as an absorption enhancer also functions as a pH adjuster of the preparation.
- the pH of the preparation is too low (for example, 3 or less), the acidity becomes too strong and the skin irritation increases, and if the pH is too high (for example, 9 or more), As the transdermal absorbability of the drug worsens, the skin irritation increases, and the preparation becomes colored yellow, the amount of the basic substance or absorption enhancer added to the formulation may increase.
- Ru is prepared to cormorants by Ru name to 4 ⁇ 8 c
- animal fats and oils, waxes, hydrocarbons, preservatives or wetting agents can be added and blended.
- Beef tallow, lard, horse oil, etc. as animal fats and fats, and micro-crox evening wax, montanx as waxes.
- Mitsuro, etc. as hydrocarbons such as paraffin and ceresin, and as preservatives, methyl parabens, propynol palates.
- Polyhydric alcohol such as alcohol, dipropylene glycol, etc.
- Example 1 Component Weight%
- Methyl paraben 0.1 Propyl paraben 0.1 (9) 1 1- (2-hydroxypropyl) pyrrolidine 0.5
- Nimesulide particles size: 0.510 ⁇ m
- Carboxy vinyl polymer 1
- Adipic acid diisoproate Pil 5 4
- Isopropyl myristate 10 5
- Ment 9 6
- Polyoxyethylene 20
- Sonorebi Tammonostearate 5 5
- Methinol paraben 0.1 8
- Propinolate paraben 0.1 9
- Example 8 (dispersed creaming agent having an active ingredient particle diameter of 76 to 180 m)
- Test example 1 Rat carrageenin Foot edema suppression test
- test substance was applied to the right foot of a male male male rat weighing 132-150 g, and the animal was fixed with a rubber film.
- animals were given plastic neck shackles and housed in individual gages to prevent ingestion of the drug orally.
- the drug was completely removed with absorbent cotton soaked in warm water.
- a 1% strength lagenin physiological saline solution was injected subcutaneously (0.1 ml) into the foot. After 3 hours, measure the foot volume and The edema rate was determined from the foot volume before the injection of the flammable substance.
- Table 1 The test results are shown in Table 1.
- Test example 2 Coloring test
- the topical anti-inflammatory agent comprising Nimesulide of the present invention in a dispersed state has a pharmacological effect equal to or higher than that of the soluble type, and is safe without irritation to the skin. In addition, it does not stain skin or clothing because it is not colored. Accordingly, the present invention relates to a therapeutic agent for dermatological areas such as eczema, dermatitis, or the like, or chronic rheumatoid arthritis, osteoarthritis, shoulder periarthritis, tenosynovitis, muscle pain, It is very useful as an anti-inflammatory external treatment for orthopedic areas such as swelling after trauma and pain.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RO97-01018A RO116040B1 (ro) | 1995-10-05 | 1996-04-01 | Compozitie antiinflamatoare pentru uz extern |
NZ327092A NZ327092A (en) | 1995-10-05 | 1996-04-01 | Topical medicaments containing nimesulide |
HU9901126A HU224686B1 (hu) | 1995-10-05 | 1996-04-01 | Külsőleg alkalmazható, nimeszulidot tartalmazó gyógyszerkészítmény és eljárás előállítására |
EE9700123A EE03419B1 (et) | 1995-10-05 | 1996-04-01 | Välispidiselt kasutatav põletikuvastane vahend |
SI9620016A SI9620016B (sl) | 1995-10-05 | 1996-04-01 | Antiinflamatorno sredstvo za zunanjo rabo |
PL96320534A PL183588B1 (pl) | 1995-10-05 | 1996-04-01 | Środek przeciwzapalny do użytku zewnętrznego zawierający nimesulid |
SK704-97A SK282637B6 (sk) | 1995-10-05 | 1996-04-01 | Protizápalový prostriedok a spôsob jeho výroby |
UA97052403A UA42795C2 (uk) | 1994-10-05 | 1996-04-01 | Протизапальний засіб для зовнішнього застосування, що містить німесулід, і спосіб його одержання |
BG101526A BG63328B1 (bg) | 1995-10-05 | 1997-05-29 | Противовъзпалително средство за външно приложение |
FI972362A FI118953B (fi) | 1995-10-05 | 1997-06-04 | Ulkoisesti käytettävä, nimesulidia käsittävä tulehdusta torjuva aine |
IS4497A IS2271B (is) | 1995-10-05 | 1997-06-04 | Bólgueyðandi miðill til útvortis notkunar |
NO19972537A NO315732B1 (no) | 1995-10-05 | 1997-06-04 | Antiinflammatorisk middel til utvortes bruk |
LVP-97-108A LV11966B (en) | 1995-10-05 | 1997-06-04 | ANTI-FRAUD MEASURE FOR EXTERNAL USE |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
USPCT/JP95/02045 | 1995-10-05 | ||
PCT/JP1995/002045 WO1996011002A1 (fr) | 1994-10-05 | 1995-10-05 | Agent anti-inflammatoire a usage externe |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997012608A1 true WO1997012608A1 (fr) | 1997-04-10 |
Family
ID=14126349
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1996/000849 WO1997012608A1 (fr) | 1994-10-05 | 1996-04-01 | Agent anti-inflammatoire externe |
Country Status (17)
Country | Link |
---|---|
BG (1) | BG63328B1 (no) |
CZ (1) | CZ288398B6 (no) |
EE (1) | EE03419B1 (no) |
FI (1) | FI118953B (no) |
HU (1) | HU224686B1 (no) |
IS (1) | IS2271B (no) |
LT (1) | LT4329B (no) |
LV (1) | LV11966B (no) |
NO (1) | NO315732B1 (no) |
NZ (1) | NZ327092A (no) |
PL (1) | PL183588B1 (no) |
RO (1) | RO116040B1 (no) |
RU (1) | RU2157683C2 (no) |
SI (1) | SI9620016B (no) |
SK (1) | SK282637B6 (no) |
TR (1) | TR199700409T1 (no) |
WO (1) | WO1997012608A1 (no) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998037879A1 (en) * | 1997-02-25 | 1998-09-03 | Helsinn Healthcare S.A. | Nimesulide gel systems for topical use |
EP0880965A1 (en) * | 1997-05-26 | 1998-12-02 | Dompe' International S.A.M. | Topical pharmaceutical formulations containing nimesulide |
WO2000048588A1 (en) * | 1999-02-16 | 2000-08-24 | Farmaceutici Formenti S.P.A. | Pharmaceutical topical compositions containing a non-steroidal antiinflammatory drug |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
RU2657803C1 (ru) * | 2017-03-21 | 2018-06-15 | федеральное государственное бюджетное образовательное учреждение высшего образования "Алтайский государственный университет" | Средство, обладающее противовоспалительным и анальгезирующим действием |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60209515A (ja) * | 1984-04-03 | 1985-10-22 | Hokuriku Seiyaku Co Ltd | 消炎鎮痛クリ−ム剤 |
JPH01224328A (ja) * | 1988-03-01 | 1989-09-07 | Kao Corp | 鎮痒剤組成物 |
JPH05310508A (ja) * | 1992-05-13 | 1993-11-22 | Kanebo Ltd | 皮膚外用剤組成物 |
WO1995034533A1 (fr) * | 1994-06-16 | 1995-12-21 | Europharmaceuticals S.A. | Sel de nimesulide hydrosoluble et leurs utilisations pour le traitement des affections inflammatoires |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3480597A (en) | 1967-03-01 | 1969-11-25 | Vasily Vladimirovich Korshak | Method for the production of polyarylates |
JPS5835989A (ja) | 1981-08-28 | 1983-03-02 | Sanyo Electric Co Ltd | 非晶質光半導体装置 |
JPS5850984A (ja) | 1981-09-24 | 1983-03-25 | 松下電工株式会社 | 電気カミソリ |
IT1248475B (it) | 1990-05-22 | 1995-01-19 | Angeli Inst Spa | Composti di inclusione di nimesulide con ciclodestrine |
-
1996
- 1996-04-01 RU RU97111164/14A patent/RU2157683C2/ru not_active IP Right Cessation
- 1996-04-01 PL PL96320534A patent/PL183588B1/pl not_active IP Right Cessation
- 1996-04-01 WO PCT/JP1996/000849 patent/WO1997012608A1/ja active IP Right Grant
- 1996-04-01 NZ NZ327092A patent/NZ327092A/en unknown
- 1996-04-01 SI SI9620016A patent/SI9620016B/sl not_active IP Right Cessation
- 1996-04-01 HU HU9901126A patent/HU224686B1/hu not_active IP Right Cessation
- 1996-04-01 RO RO97-01018A patent/RO116040B1/ro unknown
- 1996-04-01 CZ CZ19971703A patent/CZ288398B6/cs not_active IP Right Cessation
- 1996-04-01 SK SK704-97A patent/SK282637B6/sk not_active IP Right Cessation
- 1996-04-01 TR TR97/00409T patent/TR199700409T1/xx unknown
- 1996-04-01 EE EE9700123A patent/EE03419B1/xx not_active IP Right Cessation
-
1997
- 1997-05-29 BG BG101526A patent/BG63328B1/bg unknown
- 1997-06-03 LT LT97-100A patent/LT4329B/lt not_active IP Right Cessation
- 1997-06-04 LV LVP-97-108A patent/LV11966B/en unknown
- 1997-06-04 FI FI972362A patent/FI118953B/fi active IP Right Grant
- 1997-06-04 NO NO19972537A patent/NO315732B1/no unknown
- 1997-06-04 IS IS4497A patent/IS2271B/is unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60209515A (ja) * | 1984-04-03 | 1985-10-22 | Hokuriku Seiyaku Co Ltd | 消炎鎮痛クリ−ム剤 |
JPH01224328A (ja) * | 1988-03-01 | 1989-09-07 | Kao Corp | 鎮痒剤組成物 |
JPH05310508A (ja) * | 1992-05-13 | 1993-11-22 | Kanebo Ltd | 皮膚外用剤組成物 |
WO1995034533A1 (fr) * | 1994-06-16 | 1995-12-21 | Europharmaceuticals S.A. | Sel de nimesulide hydrosoluble et leurs utilisations pour le traitement des affections inflammatoires |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1998037879A1 (en) * | 1997-02-25 | 1998-09-03 | Helsinn Healthcare S.A. | Nimesulide gel systems for topical use |
EP0880965A1 (en) * | 1997-05-26 | 1998-12-02 | Dompe' International S.A.M. | Topical pharmaceutical formulations containing nimesulide |
WO2000048588A1 (en) * | 1999-02-16 | 2000-08-24 | Farmaceutici Formenti S.P.A. | Pharmaceutical topical compositions containing a non-steroidal antiinflammatory drug |
Also Published As
Publication number | Publication date |
---|---|
LT4329B (lt) | 1998-04-27 |
HUP9901126A3 (en) | 2000-08-28 |
IS2271B (is) | 2007-07-15 |
SI9620016A (en) | 1997-12-31 |
SK70497A3 (en) | 1997-10-08 |
PL320534A1 (en) | 1997-10-13 |
HU224686B1 (hu) | 2005-12-28 |
LV11966A (lv) | 1998-02-20 |
NZ327092A (en) | 1999-09-29 |
RO116040B1 (ro) | 2000-10-30 |
EE9700123A (et) | 1997-12-15 |
PL183588B1 (pl) | 2002-06-28 |
CZ288398B6 (en) | 2001-06-13 |
HUP9901126A2 (hu) | 1999-08-30 |
FI972362A (fi) | 1997-07-25 |
SK282637B6 (sk) | 2002-10-08 |
EE03419B1 (et) | 2001-06-15 |
BG101526A (en) | 1998-01-30 |
LV11966B (en) | 1998-04-20 |
NO972537L (no) | 1997-06-04 |
CZ170397A3 (cs) | 1998-01-14 |
NO972537D0 (no) | 1997-06-04 |
NO315732B1 (no) | 2003-10-20 |
IS4497A (is) | 1997-06-04 |
TR199700409T1 (xx) | 1999-08-23 |
FI972362A0 (fi) | 1997-06-04 |
RU2157683C2 (ru) | 2000-10-20 |
SI9620016B (sl) | 1999-06-30 |
FI118953B (fi) | 2008-05-30 |
BG63328B1 (bg) | 2001-10-31 |
LT97100A (en) | 1997-12-29 |
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