EP0695182A1 - Systeme zur kontrollierten abgabe von pilocarpin - Google Patents
Systeme zur kontrollierten abgabe von pilocarpinInfo
- Publication number
- EP0695182A1 EP0695182A1 EP94915110A EP94915110A EP0695182A1 EP 0695182 A1 EP0695182 A1 EP 0695182A1 EP 94915110 A EP94915110 A EP 94915110A EP 94915110 A EP94915110 A EP 94915110A EP 0695182 A1 EP0695182 A1 EP 0695182A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- pilocarpine
- transdermal therapeutic
- therapeutic system
- polymer material
- copolymers
- 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- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
-
- 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Definitions
- the invention relates to a transdermal therapeutic system for the controlled delivery of pilocarpine to the skin with a backing layer and a pressure-sensitive adhesive reservoir layer, a method for its production and the use of a capsule made of a semipermeable membrane for the controlled delivery of pilocarpine ((3S, 4R) - 3 - ethyl-4,5-dihydro - 4 - (1-methyl - 1H-imidazol - 5-ylmethyl) - 2 (3 H) - furanone).
- Pilocarpine is an alkaloid that consists of various species of the genus Pilocarpus (Rutaceae (Rutales)) e.g. by Pilo-carpus jaborandi Holmes u. a. won and used in ophthalmology for over 100 years.
- Patients with glaucoma use pilocarpine drops, which have to be instilled into the conjunctival sac of the eye several times a day. With glaucoma, there is increased internal pressure in the eye, which, if left untreated, can damage the retina and optic nerve.
- Pilocarpine narrows the pupil in the eye, the outflow of the chamber water in the eye is facilitated and thus the intraocular pressure is reduced.
- the effect of one application lasts for 4 to 6 hours, so that several applications per day are required to lower the intraocular pressure throughout the day. Especially early in the morning, the drop in the effect of the dose dropped in the evening and the physiological increase in eye pressure around this time lead to an uncontrolled increase in pressure values.
- the object of the invention is therefore to provide a medicament for the systemic administration of pilocarpine to lower the intraocular pressure while at the same time suppressing the side effects.
- transdermal therapeutic system according to claim 1 and by the se ipermeable capsule according to claim 20.
- the subclaims relate to particularly preferred embodiments of the invention and a method for producing the transdermal therapeutic system.
- the invention relates to a transdermal therapeutic system for controlled drug delivery to the skin with a backing layer and a pressure-sensitive adhesive reservoir layer, which is characterized in that the reservoir layer contains a polymer material, a plasticizer and a pilocarpine base or one of its pharmaceutically acceptable salts.
- the invention further relates to the use of a capsule made of a semipermeable membrane for the controlled release of pilocarpine, in which pilocarpine is encapsulated and which has an opening in the capsule material, for the treatment of glaucoma.
- the pilocarpine may be as such or in the form of pharmaceutically acceptable acid addition salts, e.g. as a hydrohalide, in particular chloride or as a salt of another pharmaceutically acceptable acid, preferably nitric acid.
- agents generally also contain auxiliaries, such as carriers, flow improvers, solvents and oils, the type and amount of which vary depending on the dosage form.
- auxiliaries such as carriers, flow improvers, solvents and oils, the type and amount of which vary depending on the dosage form.
- the active ingredient content is calculated as
- REPLACEMENT SHEET (RULE 26) free pilocarpine base between 0.1-50% by weight, preferably between 2 and 15% by weight.
- the active pharmaceutical ingredient is e.g. encapsulated in a semipermeable membrane, e.g. in cellulose acetate.
- a semipermeable membrane e.g. in cellulose acetate.
- a tiny hole is drilled into the capsule material using a drill or laser.
- the capsule material absorbs water in the patient's body being treated.
- the pharmaceutical active ingredient is forced through the small opening by osmotic pressure in the desired gradual, constant and controlled manner.
- the pharmaceutical active ingredients can be in solid form or absorbed by ion exchange resins.
- the active compounds of the present invention are administered in a suitable and suitable manner by means of appropriate formulations.
- the solid active ingredients can be administered in solution or as a suspension.
- the solution or suspension medium can be aqueous or organic.
- Suitable solution or suspension media for pilocarpine are, for example, water, silicone fluid or mineral oil.
- a flow improver can be added to the system.
- suitable flow improvers for oral formulations include, for example, polyethylene glycol, hydroxypropylmethyl cellulose and sugar.
- TTS transdermal therapeutic system
- a TTS can e.g. consist of a backing layer, a pressure-sensitive adhesive, active substance-containing reservoir layer and a removable protective layer.
- the backing layer is preferably impermeable to active substances.
- the active substance-impermeable backing layer can consist of flexible or non-flexible material.
- Substances which can be used for their production are polymer foils or metal foils, such as aluminum foil, which are used alone or coated with a polymeric substrate. Textile fabrics can also be used if the components of the reservoir cannot pass through them due to their physical nature.
- the backing layer is a composite material made from a foil vapor-coated with aluminum.
- the reservoir layer consists of a polymer material and the active ingredient, the polymer material also ensuring the cohesion of the system. It contains a basic polymer and, if necessary, customary additives.
- the choice of the base polymer depends on the chemical and physical properties of the pilocarpine.
- Exemplary polymers are rubber, rubber-like, synthetic homopolymers, copolymers, block polymers, block copolymers, polyacrylic acid esters and their copolymers, polyurethanes, silicones and polyacrylates. Basically, all polymers come into question that can be used in the production of pressure sensitive adhesives and are physiologically harmless. Particularly preferred are those consisting of block copolymers based on styrene and 1,3-dienes, polyisobutylenes, silicones, polymers based on acrylate and / or methacrylate.
- block copolymers based on styrene and 1,3-dienes very particularly linear styrene-isoprene or styrene-butadiene block copolymers are used.
- the polymer material selected from the group of polyacrylates is a polymerization product of acrylic acid and its esters or methacrylic acid and its esters.
- the esters of acrylic acid preferably comprise alcohols with 2-4 carbons as alcoholic constituents.
- the esters of acrylic acid comprise, as alcoholic constituents, straight-chain or branched alcohols with 4-10 carbons.
- the esters of methacrylic acid include amino alcohols as alcoholic constituents.
- Polymethacrylates and polyvinyls come into consideration as polymers which are added to the base polymer.
- Copolymers based on dimethylaminoethyl methacrylates and neutral methacrylic acid esters are preferred as methacrylates.
- Polyvinylpyrrolidines and polyvinyl alcohols are preferably used as polyvinyls.
- plasticizer depends on the polymer. Higher alcohols such as dodecanol, undecanol, octanol, oleyl alcohol and 2-octyldodecanol and esters of carboxylic acids (for example isopropyl myristate or palmitate, where the alcohol component can also be a polyethoxylated alcohol) are particularly suitable, diesters of dicarboxylic acids, for example di-n -butyl adipate and triglycerides, especially medium-chain triglycerides of caprylic / capric acids of coconut oil). Further examples of a suitable plasticizer are polyhydric alcohols, e.g. Glycerol and propanediol- (1,2) and others, which can also be etherified by polyethylene glycols.
- carboxylic acids for example isopropyl myristate or palmitate, where the alcohol component can also be a polyethoxylated alcohol
- diesters of dicarboxylic acids for example di
- STATEMENT SHEET RULE2b are octanoic acid, levulinic acid, undecenoic acid, oleic acid and stearic acid and their isomers.
- the type of usual additives depends on the polymer used. According to their function, they can be divided into, for example, tackifiers, stabilizers, carriers and fillers.
- tackifiers for example, tackifiers, stabilizers, carriers and fillers.
- the physiologically harmless substances that are capable of this are known to the person skilled in the art.
- the reservoir layer is so sticky that it ensures permanent contact with the skin.
- the removable protective layer which is in contact with the reservoir layer and is removed before use, consists, for example, of the same materials as are used to produce the backing layer, provided that they are made removable, e.g. through a silicone treatment.
- Other removable protective layers are e.g. Polytetrafluoroethylene, treated paper, cellophane, polyvinyl chloride and others If the laminate according to the invention is divided into therapy-appropriate formats (plasters) before the protective layer is applied, the protective layer formats then to be applied can have a protruding end, with the aid of which they can be removed more easily from the plasters.
- the reservoir layer contains 40-85% by weight polymer material, 0-30 Ge plasticizer and 0.1-30% by weight pilocarpine base or one of its pharmaceutically acceptable salts.
- the reservoir layer preferably has 40-80% by weight of polymer material, 0-30% by weight of plasticizer and 0.1-30% by weight of pilocarpine base.
- the process for producing a transdermal therapeutic system comprises dissolving self-crosslinking acrylate copolymer in a mixture of organic solvents, adding a plasticizer and a pilocarpine base, sprinkling polymethacrylates as copolymers and applying the adhesive solution to an aluminized and siliconized polyester film as a backing layer after dissolving the interspersed polymethacrylates.
- the transdermal therapeutic system according to the invention is produced by spreading the active ingredient together with the constituents of the pressure-sensitive adhesive reservoir layer, optionally homogeneously in solution, onto the backing layer impermeable to the active ingredient, whereupon the solvent or the solvents are removed.
- the adhesive layer is then provided with a corresponding protective layer.
- PMA copolymer with a basic character based on dimethylaminoethyl methacrylate and neutral methacrylic acid esters
- IPM isopropyl yristat
- the in vitro release was determined in a shaking water bath at 37 ° C.
- the acceptor medium was 100 ml of physiological saline, which was completely replaced after 2, 4 and 8 hours.
- the concentration was determined after 2, 4, 8 and 24 hours by HPLC.
- the penetration on the mouse skin was measured on Franz's diffusion cells.
- Example 1 In order to clinically test the effectiveness of the Pilocarpine TTS, a first clinical test of the TTS (Example 1) was carried out in comparison with 2% eye drops on 6 healthy volunteers. The test was carried out on healthy people, d on the one hand no data are available on the therapeutic efficacy in existing glaucoma and transdermal application of pilocarpine, but on the other hand it is known that a reduction in pressure on the eye can also be achieved in healthy people with pilocarpine.
- FIGS. 1 and 2 The effect of pilocarpine after intraocular and transdermal administration is shown in FIGS. 1 and 2.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Ophthalmology & Optometry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4313928A DE4313928C2 (de) | 1993-04-28 | 1993-04-28 | Transdermales therapeutisches System zur kontrollierten Abgabe von Pilocarpin an die Haut, Verfahren zu seiner Herstellung und seine Verwendung |
DE4313928 | 1993-04-28 | ||
PCT/EP1994/001281 WO1994025025A2 (de) | 1993-04-28 | 1994-04-25 | Systeme zur kontrollierten abgabe von pilocarpin |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0695182A1 true EP0695182A1 (de) | 1996-02-07 |
Family
ID=6486612
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94915110A Withdrawn EP0695182A1 (de) | 1993-04-28 | 1994-04-25 | Systeme zur kontrollierten abgabe von pilocarpin |
Country Status (19)
Country | Link |
---|---|
US (1) | US5869086A (de) |
EP (1) | EP0695182A1 (de) |
JP (1) | JPH08509716A (de) |
KR (1) | KR960702308A (de) |
AU (1) | AU694115B2 (de) |
CA (1) | CA2161520A1 (de) |
CZ (1) | CZ277995A3 (de) |
DE (1) | DE4313928C2 (de) |
FI (1) | FI955161A (de) |
HR (1) | HRP940270A2 (de) |
HU (1) | HU220045B (de) |
IL (1) | IL109340A (de) |
NO (1) | NO309174B1 (de) |
NZ (1) | NZ265950A (de) |
PL (1) | PL175077B1 (de) |
SK (1) | SK134395A3 (de) |
WO (1) | WO1994025025A2 (de) |
YU (1) | YU22894A (de) |
ZA (1) | ZA942874B (de) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU719171B2 (en) * | 1995-01-14 | 2000-05-04 | Abbott Laboratories | A transdermal therapeutic system for the administration of (s)-3-methyl-5-(1-methyl-2-pyrrolidinyl)-isoxazole or one of its pharmaceutically acceptable salts |
DE19501022C1 (de) * | 1995-01-14 | 1996-06-05 | Lohmann Therapie Syst Lts | Transdermales therapeutisches System zur Verabreichung von (s)-3-Methyl-5-(1-methyl-2-pyrrolidenyl)-isoxazol oder einem seiner pharmazeutisch akzeptablen Salze und Verfahren zu seiner Herstellung |
EP1221315A4 (de) * | 1999-10-13 | 2007-12-12 | Senju Pharma Co | Adhäsive ophthalmische zubereitungen zur perkutanen absporption |
DE10246503A1 (de) * | 2002-03-26 | 2003-10-16 | Tesa Ag | Verwendung von Haftklebemassen für medizinische Verklebungen |
KR20130121196A (ko) * | 2003-01-22 | 2013-11-05 | 센주 세이야꾸 가부시키가이샤 | 안질환 치료용 경피 흡수형 제제, 그 사용, 및 안질환 치료약의 눈의 국소 조직으로의 이행 방법 |
US20070053964A1 (en) * | 2004-05-21 | 2007-03-08 | Akiharu Isowaki | Ophthalmic percutaneously absorbed preparation containing muscarinic receptor agonist |
KR20070104912A (ko) * | 2005-02-17 | 2007-10-29 | 센주 세이야꾸 가부시키가이샤 | 안과용 고형 외용약제 |
KR20080031430A (ko) * | 2005-07-26 | 2008-04-08 | 센주 세이야꾸 가부시키가이샤 | 경피적으로 흡수가능한 안과용 제제 |
US20100323978A1 (en) * | 2009-06-22 | 2010-12-23 | Calvin Hanna | Non-aqueous oil delivery system for ophthalmic drugs |
WO2012048455A1 (zh) * | 2010-10-12 | 2012-04-19 | 武汉大学 | 一种抗病毒透皮吸收贴片及其制备方法 |
KR101688061B1 (ko) | 2014-10-06 | 2017-01-02 | 주식회사한국파마 | 필로카르핀 경피 흡수 제제 |
JP6526475B2 (ja) * | 2015-04-30 | 2019-06-05 | サンスター株式会社 | 経皮唾液腺投与用の唾液分泌促進剤 |
Family Cites Families (20)
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US3220960A (en) * | 1960-12-21 | 1965-11-30 | Wichterle Otto | Cross-linked hydrophilic polymers and articles made therefrom |
US3797494A (en) * | 1969-04-01 | 1974-03-19 | Alza Corp | Bandage for the administration of drug by controlled metering through microporous materials |
US3760805A (en) * | 1971-01-13 | 1973-09-25 | Alza Corp | Osmotic dispenser with collapsible supply container |
US4144317A (en) * | 1975-05-30 | 1979-03-13 | Alza Corporation | Device consisting of copolymer having acetoxy groups for delivering drugs |
US3987790A (en) * | 1975-10-01 | 1976-10-26 | Alza Corporation | Osmotically driven fluid dispenser |
US4137300A (en) * | 1976-08-20 | 1979-01-30 | Ciba-Geigy Corporation | Sustained action dosage forms |
IL72684A (en) * | 1984-08-14 | 1989-02-28 | Israel State | Pharmaceutical compositions for controlled transdermal delivery of cholinergic or anticholinergic basic drugs |
US4668506A (en) * | 1985-08-16 | 1987-05-26 | Bausch & Lomb Incorporated | Sustained-release formulation containing and amino acid polymer |
US4931279A (en) * | 1985-08-16 | 1990-06-05 | Bausch & Lomb Incorporated | Sustained release formulation containing an ion-exchange resin |
CA1295941C (en) * | 1985-08-16 | 1992-02-18 | Rajan Bawa | Sustained-release formulation comprising a hydrophobic polymer system |
US4713244A (en) * | 1985-08-16 | 1987-12-15 | Bausch & Lomb Incorporated | Sustained-release formulation containing an amino acid polymer with a lower alkyl (C1 -C4) polar solvent |
US5273757A (en) * | 1987-09-01 | 1993-12-28 | Lts Lohmann Therapie-Systeme Gmbh & Co. Kg | Apparatus for the delivery of substances, processes for the production thereof and use thereof |
DE3743946A1 (de) * | 1987-09-01 | 1989-03-09 | Lohmann Gmbh & Co Kg | Vorrichtung zur abgabe von nitroglycerin an die haut, verfahren zu ihrer herstellung sowie ihre verwendung |
US5300291A (en) * | 1988-03-04 | 1994-04-05 | Noven Pharmaceuticals, Inc. | Method and device for the release of drugs to the skin |
US5474783A (en) * | 1988-03-04 | 1995-12-12 | Noven Pharmaceuticals, Inc. | Solubility parameter based drug delivery system and method for altering drug saturation concentration |
US5008110A (en) * | 1988-11-10 | 1991-04-16 | The Procter & Gamble Company | Storage-stable transdermal patch |
US5021053A (en) * | 1989-07-14 | 1991-06-04 | Alza Corporation | Oral osmotic device with hydrogel driving member |
DE4002281A1 (de) * | 1990-01-26 | 1991-08-01 | Lohmann Therapie Syst Lts | Transdermales therapeutisches system mit dem wirkstoff tulobuterol |
WO1991015176A1 (en) * | 1990-04-06 | 1991-10-17 | Pharmetrix Corporation | Device and method for enhanced administration of physostigmine |
ATE167800T1 (de) * | 1990-04-27 | 1998-07-15 | Allergan Inc | Polymeres arzneimittelabgabesystem |
-
1993
- 1993-04-28 DE DE4313928A patent/DE4313928C2/de not_active Expired - Fee Related
-
1994
- 1994-04-18 IL IL10934094A patent/IL109340A/en not_active IP Right Cessation
- 1994-04-25 WO PCT/EP1994/001281 patent/WO1994025025A2/de not_active Application Discontinuation
- 1994-04-25 PL PL94311281A patent/PL175077B1/pl unknown
- 1994-04-25 EP EP94915110A patent/EP0695182A1/de not_active Withdrawn
- 1994-04-25 CA CA002161520A patent/CA2161520A1/en not_active Abandoned
- 1994-04-25 US US08/553,346 patent/US5869086A/en not_active Expired - Fee Related
- 1994-04-25 JP JP6523855A patent/JPH08509716A/ja active Pending
- 1994-04-25 HU HU9503087A patent/HU220045B/hu not_active IP Right Cessation
- 1994-04-25 SK SK1343-95A patent/SK134395A3/sk unknown
- 1994-04-25 NZ NZ265950A patent/NZ265950A/xx unknown
- 1994-04-25 CZ CZ952779A patent/CZ277995A3/cs unknown
- 1994-04-25 AU AU66481/94A patent/AU694115B2/en not_active Ceased
- 1994-04-26 ZA ZA942874A patent/ZA942874B/xx unknown
- 1994-04-27 YU YU22894A patent/YU22894A/sh unknown
- 1994-04-27 HR HRP4313928.0A patent/HRP940270A2/xx not_active Application Discontinuation
-
1995
- 1995-10-27 NO NO954325A patent/NO309174B1/no not_active IP Right Cessation
- 1995-10-27 FI FI955161A patent/FI955161A/fi unknown
- 1995-10-27 KR KR1019950704711A patent/KR960702308A/ko not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO9425025A2 * |
Also Published As
Publication number | Publication date |
---|---|
IL109340A0 (en) | 1994-07-31 |
PL311281A1 (en) | 1996-02-05 |
PL175077B1 (pl) | 1998-10-30 |
AU694115B2 (en) | 1998-07-16 |
JPH08509716A (ja) | 1996-10-15 |
DE4313928A1 (de) | 1994-11-03 |
WO1994025025A3 (de) | 1995-03-02 |
HRP940270A2 (en) | 1996-08-31 |
FI955161A0 (fi) | 1995-10-27 |
NZ265950A (en) | 1997-08-22 |
IL109340A (en) | 1998-10-30 |
NO954325D0 (no) | 1995-10-27 |
WO1994025025A2 (de) | 1994-11-10 |
HU9503087D0 (en) | 1995-12-28 |
HUT75029A (en) | 1997-03-28 |
FI955161A (fi) | 1995-11-24 |
ZA942874B (en) | 1995-07-06 |
US5869086A (en) | 1999-02-09 |
CZ277995A3 (en) | 1996-05-15 |
CA2161520A1 (en) | 1994-11-10 |
SK134395A3 (en) | 1997-02-05 |
AU6648194A (en) | 1994-11-21 |
DE4313928C2 (de) | 1996-09-19 |
YU22894A (sh) | 1997-08-22 |
KR960702308A (ko) | 1996-04-27 |
NO954325L (no) | 1995-10-30 |
NO309174B1 (no) | 2000-12-27 |
HU220045B (hu) | 2001-10-28 |
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