AU641407B2 - Octreotide-pamoate - Google Patents
Octreotide-pamoate Download PDFInfo
- Publication number
- AU641407B2 AU641407B2 AU58746/90A AU5874690A AU641407B2 AU 641407 B2 AU641407 B2 AU 641407B2 AU 58746/90 A AU58746/90 A AU 58746/90A AU 5874690 A AU5874690 A AU 5874690A AU 641407 B2 AU641407 B2 AU 641407B2
- Authority
- AU
- Australia
- Prior art keywords
- octreotide
- pamoate
- preparation
- acid
- spe
- 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.)
- Expired
Links
Classifications
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
- A61K38/095—Oxytocins; Vasopressins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/23—Calcitonins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/31—Somatostatins
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
641407 COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION NAME ADDRESS OF APPLICANT: Sandoz Ltd.
Lichtstrasse CH-4002 Basle Switzerland NAME(S) OF INVENTOR(S): David BODMER Jones Wing FONG Thomas KISSEL Hawkins Valliant MAULDING Oskar NAGELE Jane Edna PEARSON ADDRESS FOR SERVICE: DAVIES COLLISON Patent Attorneys 1 Little Collins Street, Melbourne, 3000.
COMPLETE SPECIFICATION FOR THE INVENTION ENTITLED: Improvements in or relating to organic compound Octreo-de- pomoode The following statement is a full description of this invention, including the best method of performing it known to me/us:-
OCTREOTIDE-PAMOATE
This invention relates to a salt of octreotide.
We have found that a novel salt of octreotide is the pamoate which is very stable in sustained release formulations.
According to the present invention there is provided octreotide pamoate and (ii) a process for the production of octreotide pamoate which comprises reacting octreotide with embonic acid (or a reactive derivative thereof).
The octreotide-pamoate is useful, particularly for implants.
r SO *5*S
-S
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S
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i
S
S
20 The pamoate may be obtained in conventional manner, e.g. by reacting embonic acid (pamoic acid) with octreotide e.g. in free base form. The reaction may be effected in a polar solvent, e.g. at room temperature.
EXAMPLE 1: Octreotide pamoate 10.19 g of octreotide free base (10 mM) and 3.88 embonoic acid (10mM) are dissolved in 1 litre of water/dioxane The reaction mixture is filtered, and lyophilized to give a yellow powder [a]2D 7.5 (C 0.35, in DMF), of 30 octreotide pamoate hydrate. Factor 1.4 wherein the factor weight of lyophilizate/weight of octreotide contained therein.
930708,p:\operedabS8746-9O.SPE,1
Claims (4)
1. Octreotide-pamoate
2. A process for the preparation of octreotide pamoate in which octreotide is reacted 'with embonic acid or a reactive derivative thereof.
3. Octreotide-pamoate or a process for its preparation, substantially as hereinbefore described with reference to the Example. DATED this 8Hi day of July, 1993 SANDOZ LIMITED By Its Patent Attorneys DAVIES COLLISON CAVE S S S S SS S S S S 55 S S S S *5 S S S S S
55.. 930708,p:\oper'idab,58746-90.SPE,2
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37702389A | 1989-07-07 | 1989-07-07 | |
| US377023 | 1989-07-07 | ||
| US41134789A | 1989-09-22 | 1989-09-22 | |
| US411347 | 1989-09-22 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU41985/93A Division AU662825B2 (en) | 1989-07-07 | 1993-07-15 | Process for the production of microparticles |
| AU41986/93A Division AU663388B2 (en) | 1989-07-07 | 1993-07-15 | Sustained release formulations |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5874690A AU5874690A (en) | 1991-01-10 |
| AU641407B2 true AU641407B2 (en) | 1993-09-23 |
Family
ID=27007654
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU58746/90A Expired AU641407B2 (en) | 1989-07-07 | 1990-07-05 | Octreotide-pamoate |
| AU23321/95A Expired AU687553B2 (en) | 1989-07-07 | 1995-06-29 | Process for the production of microparticles |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU23321/95A Expired AU687553B2 (en) | 1989-07-07 | 1995-06-29 | Process for the production of microparticles |
Country Status (27)
| Country | Link |
|---|---|
| JP (5) | JPH0832624B2 (en) |
| KR (2) | KR100303681B1 (en) |
| AT (1) | AT406225B (en) |
| AU (2) | AU641407B2 (en) |
| BE (1) | BE1004486A3 (en) |
| CA (1) | CA2020477C (en) |
| CH (1) | CH685230A5 (en) |
| CY (1) | CY1965A (en) |
| DE (2) | DE4021517B4 (en) |
| DK (1) | DK175849B1 (en) |
| FI (3) | FI108611B (en) |
| FR (1) | FR2649319A1 (en) |
| GB (2) | GB2234896B (en) |
| GR (1) | GR1001121B (en) |
| HK (2) | HK97695A (en) |
| HU (2) | HU221294B1 (en) |
| IE (2) | IE64411B1 (en) |
| IL (3) | IL94983A (en) |
| IT (1) | IT1241460B (en) |
| LU (1) | LU87764A1 (en) |
| MY (1) | MY106722A (en) |
| NL (1) | NL195027C (en) |
| NO (2) | NO302928B1 (en) |
| NZ (1) | NZ234384A (en) |
| PT (1) | PT94628B (en) |
| SE (1) | SE512992C2 (en) |
| SG (1) | SG26416G (en) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4990336A (en) * | 1989-02-08 | 1991-02-05 | Biosearch, Inc. | Sustained release dosage form |
| YU48420B (en) * | 1991-03-25 | 1998-07-10 | Hoechst Aktiengesellschaft | PROCEDURE FOR OBTAINING BIOLOGICAL DEGRADABLE MICROPARTICLES WITH LONG TERM ACTION |
| CH683149A5 (en) * | 1991-07-22 | 1994-01-31 | Debio Rech Pharma Sa | Process for the preparation of microspheres of a biodegradable polymeric material. |
| US6013853A (en) * | 1992-02-14 | 2000-01-11 | The University Of Texas System | Continuous release polymeric implant carrier |
| US5876452A (en) * | 1992-02-14 | 1999-03-02 | Board Of Regents, University Of Texas System | Biodegradable implant |
| DE4218510A1 (en) * | 1992-06-02 | 1993-12-09 | Pharmatech Gmbh | Process for the preparation of biodegradable polyesters |
| AU4198793A (en) † | 1992-07-24 | 1994-01-27 | Takeda Chemical Industries Ltd. | Microparticle preparation and production thereof |
| EP0626170A3 (en) * | 1993-05-10 | 1996-03-27 | Sandoz Ltd | Stabilization of pharmacoligically active compounds in controlled release compositions. |
| US5603960A (en) * | 1993-05-25 | 1997-02-18 | O'hagan; Derek T. | Preparation of microparticles and method of immunization |
| GB9310781D0 (en) * | 1993-05-25 | 1993-07-14 | Davis Stanley S | Preparation of microparticles |
| CN1074923C (en) | 1993-11-19 | 2001-11-21 | 詹森药业有限公司 | Microencapsulated 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles |
| US6270795B1 (en) | 1995-11-09 | 2001-08-07 | Microbiological Research Authority | Method of making microencapsulated DNA for vaccination and gene therapy |
| DE69608122T3 (en) | 1995-11-09 | 2011-06-16 | Microbiological Research Authority Camr, Salisbury | MICROCAPPLETED DNA FOR VACCINATION AND GENE THERAPY |
| DE19545257A1 (en) | 1995-11-24 | 1997-06-19 | Schering Ag | Process for the production of morphologically uniform microcapsules and microcapsules produced by this process |
| US5817343A (en) * | 1996-05-14 | 1998-10-06 | Alkermes, Inc. | Method for fabricating polymer-based controlled-release devices |
| US5968895A (en) * | 1996-12-11 | 1999-10-19 | Praecis Pharmaceuticals, Inc. | Pharmaceutical formulations for sustained drug delivery |
| US6126919A (en) | 1997-02-07 | 2000-10-03 | 3M Innovative Properties Company | Biocompatible compounds for pharmaceutical drug delivery systems |
| GB9810236D0 (en) | 1998-05-13 | 1998-07-08 | Microbiological Res Authority | Improvements relating to encapsulation of bioactive agents |
| US6632457B1 (en) * | 1998-08-14 | 2003-10-14 | Incept Llc | Composite hydrogel drug delivery systems |
| US6226656B1 (en) | 1998-11-12 | 2001-05-01 | Sourcefinder, Inc. | System and method for creating, generating and processing user-defined generic specs |
| US7107268B1 (en) | 1998-11-12 | 2006-09-12 | Printable Technologies, Inc. | Centralized system and method for managing enterprise operations |
| US6204308B1 (en) | 1999-03-01 | 2001-03-20 | Novartis Ag | Organic compounds |
| EP1044683A1 (en) * | 1999-04-15 | 2000-10-18 | Debio Recherche Pharmaceutique S.A. | One-step dispersion method for the microencapsulation of water soluble substances |
| US6461631B1 (en) * | 1999-11-16 | 2002-10-08 | Atrix Laboratories, Inc. | Biodegradable polymer composition |
| KR100392501B1 (en) * | 2000-06-28 | 2003-07-22 | 동국제약 주식회사 | Preparation Method for Sustained Release Microparticles by Multiple Emulsion Method and Micropartic les Thereof |
| US6824822B2 (en) * | 2001-08-31 | 2004-11-30 | Alkermes Controlled Therapeutics Inc. Ii | Residual solvent extraction method and microparticles produced thereby |
| WO2002049620A2 (en) | 2000-12-21 | 2002-06-27 | Inhale Therapeutic Systems, Inc. | Induced phase transition method for the production of microparticles containing hydrophobic active agents |
| US20040097419A1 (en) * | 2002-11-19 | 2004-05-20 | Holger Petersen | Organic compounds |
| AR044852A1 (en) * | 2003-06-24 | 2005-10-05 | Novartis Ag | A PHARMACEUTICAL COMPOSITION FOR PARENTERAL ADMINISTRATION THAT INCLUDES A SOMATOSTATINE ANALOG |
| ES2600554T3 (en) * | 2003-07-18 | 2017-02-09 | Oakwood Laboratories L.L.C. | Prevention of polymer molecular weight reduction, impurity formation and gelation in polymeric compositions |
| MY158342A (en) | 2003-11-14 | 2016-09-30 | Novartis Ag | Pharmaceutical composition |
| US20070259047A1 (en) * | 2004-02-26 | 2007-11-08 | Yasuaki Ogawa | Protein Sustained-Release Microparticle Preparation for Injection and Process for Producing the Same |
| DE102004053373A1 (en) * | 2004-11-02 | 2006-05-04 | Justus-Liebig-Universität Giessen | Invention relating to nano / meso-fiber anisometric particles in the form of nano / meso-fiber tubes, cables and their curved or branched modifications |
| KR100741867B1 (en) * | 2005-07-05 | 2007-07-24 | 전북대학교산학협력단 | Method of Preparation of Double Layered Microspheres Using Oil-in-water and Solvent Evaporation |
| ES2755032T3 (en) * | 2005-12-22 | 2020-04-21 | Novartis Ag | Sustained release formulation comprising octreotide and two or more polylactide-co-glycolide polymers |
| KR100816065B1 (en) * | 2006-11-27 | 2008-03-24 | 동국제약 주식회사 | Method for preparing sustained release microcapsules with excellent initial release control characteristics and microcapsules prepared by the same |
| KR101921800B1 (en) | 2008-01-30 | 2018-11-23 | 노파르티스 아게 | Sustained release formulation comprising octreotide and three linear polylactide-co-glycolide polymers |
| USRE49251E1 (en) | 2010-01-04 | 2022-10-18 | Mapi Pharma Ltd. | Depot systems comprising glatiramer or pharmacologically acceptable salt thereof |
| JP5808413B2 (en) * | 2010-09-30 | 2015-11-10 | エボニック コーポレイションＥｖｏｎｉｋ Ｃｏｒｐｏｒａｔｉｏｎ | Method for removing residual organic solvent from fine particles |
| RU2013119810A (en) * | 2010-09-30 | 2014-11-10 | Эвоник Корпорейшн | EMULSION METHOD FOR PRODUCING MICROPARTICLES WITH LOW CONTENT OF RESIDUAL SOLVENT |
| TW201605488A (en) | 2013-10-15 | 2016-02-16 | 大塚製藥股份有限公司 | Drug for preventing and/or treating polycystic kidney disease |
| KR102464650B1 (en) | 2016-05-03 | 2022-11-10 | 엘에스일렉트릭(주) | Current limiting device of circuit breaker |
| US12097292B2 (en) | 2016-08-28 | 2024-09-24 | Mapi Pharma Ltd. | Process for preparing microparticles containing glatiramer acetate |
| CN109982712A (en) | 2016-08-31 | 2019-07-05 | Mapi医药公司 | Depot system containing glatiramer acetate |
| CN110382052A (en) | 2017-03-26 | 2019-10-25 | Mapi医药公司 | The copaxone store system of multiple sclerosis for therapeutic advance type form |
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| DE3062075D1 (en) * | 1979-11-27 | 1983-03-24 | Sandoz Ag | Polypeptides, processes for their production, pharmaceutical compositions comprising said polypeptides and their use |
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| US4725577A (en) * | 1985-04-25 | 1988-02-16 | Administrators Of The Tulane Educational Fund | Biologically active lysine containing octapeptides |
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| GB2193891B (en) * | 1986-08-18 | 1990-07-25 | Sandoz Ltd | Nasal pharmaceutical composition containing a somatostatin anologue. |
| JPH0725689B2 (en) * | 1986-10-07 | 1995-03-22 | 中外製薬株式会社 | Sustained-release preparation containing granulocyte colony-stimulating factor |
| GB2209937B (en) * | 1987-09-21 | 1991-07-03 | Depiopharm S A | Water insoluble polypeptides |
| CH672887A5 (en) * | 1987-10-14 | 1990-01-15 | Debiopharm Sa | |
| DE3738228A1 (en) * | 1987-11-11 | 1989-05-24 | Hoechst Ag | METHOD FOR PRODUCING BIODEGRADABLE MICRO-CAPSULES OF WATER-SOLUBLE PEPTIDES AND PROTEINS AND MICRO-CAPSULES OBTAINED BY THIS PROCESS |
| JP2653255B2 (en) * | 1990-02-13 | 1997-09-17 | 武田薬品工業株式会社 | Long-term sustained release microcapsules |
-
1990
- 1990-06-25 HU HU974/90A patent/HU221294B1/en unknown
- 1990-07-03 SG SG1995907374A patent/SG26416G/en unknown
- 1990-07-03 GB GB9014704A patent/GB2234896B/en not_active Expired - Lifetime
- 1990-07-05 NZ NZ234384A patent/NZ234384A/en unknown
- 1990-07-05 IE IE43894A patent/IE64411B1/en not_active IP Right Cessation
- 1990-07-05 SE SE9002364A patent/SE512992C2/en not_active IP Right Cessation
- 1990-07-05 NO NO903001A patent/NO302928B1/en not_active IP Right Cessation
- 1990-07-05 NL NL9001537A patent/NL195027C/en not_active IP Right Cessation
- 1990-07-05 GR GR900100513A patent/GR1001121B/en not_active IP Right Cessation
- 1990-07-05 IE IE243590A patent/IE64216B1/en not_active IP Right Cessation
- 1990-07-05 AU AU58746/90A patent/AU641407B2/en not_active Expired
- 1990-07-05 IT IT48113A patent/IT1241460B/en active IP Right Grant
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1993
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1995
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