CA1336326C - Microbeads of diltiazem, a process for their manufacture and a sustained-release pharmaceutical composition containing them - Google Patents
Microbeads of diltiazem, a process for their manufacture and a sustained-release pharmaceutical composition containing themInfo
- Publication number
- CA1336326C CA1336326C CA000596597A CA596597A CA1336326C CA 1336326 C CA1336326 C CA 1336326C CA 000596597 A CA000596597 A CA 000596597A CA 596597 A CA596597 A CA 596597A CA 1336326 C CA1336326 C CA 1336326C
- Authority
- CA
- Canada
- Prior art keywords
- microbeads
- diltiazem
- membrane
- microbeads according
- core
- 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 - Fee Related
Links
- 239000011325 microbead Substances 0.000 title claims abstract description 52
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 title claims abstract description 24
- 229960004166 diltiazem Drugs 0.000 title claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 239000012730 sustained-release form Substances 0.000 title claims abstract description 10
- 238000013268 sustained release Methods 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 31
- 239000012528 membrane Substances 0.000 claims abstract description 25
- 239000002775 capsule Substances 0.000 claims abstract description 14
- 238000000338 in vitro Methods 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 7
- 239000012982 microporous membrane Substances 0.000 claims abstract description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000012736 aqueous medium Substances 0.000 claims abstract description 3
- 239000006185 dispersion Substances 0.000 claims abstract description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims abstract description 3
- 238000005507 spraying Methods 0.000 claims description 11
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 9
- 229920001249 ethyl cellulose Polymers 0.000 claims description 9
- 239000001856 Ethyl cellulose Substances 0.000 claims description 8
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 8
- 239000000454 talc Substances 0.000 claims description 8
- 229910052623 talc Inorganic materials 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000004359 castor oil Substances 0.000 claims description 6
- 235000019438 castor oil Nutrition 0.000 claims description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 229910052914 metal silicate Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 abstract description 2
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 abstract description 2
- 230000008020 evaporation Effects 0.000 abstract description 2
- 239000004014 plasticizer Substances 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000000470 constituent Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 10
- 238000009792 diffusion process Methods 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 7
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000036470 plasma concentration Effects 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000012738 dissolution medium Substances 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- -1 polyglycol Chemical compound 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- FEDJGPQLLNQAIY-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)oxy]acetic acid Chemical compound OC(=O)COC=1C=CC(=O)NN=1 FEDJGPQLLNQAIY-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229920013820 alkyl cellulose Polymers 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 229920000249 biocompatible polymer Polymers 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229960005316 diltiazem hydrochloride Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 238000007873 sieving Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229920003134 Eudragit® polymer Polymers 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229920003072 Plasdone™ povidone Polymers 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000000416 hydrocolloid Substances 0.000 description 1
- 210000001630 jejunum Anatomy 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000003232 water-soluble binding agent Substances 0.000 description 1
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
- A61K9/5073—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 having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—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 having two or more different coatings optionally including drug-containing subcoatings with drug-free core
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8805629A FR2630647B1 (fr) | 1988-04-27 | 1988-04-27 | Microbilles de diltiazem, leur procede de fabrication et compositions pharmaceutiques a liberation prolongee les contenant |
| FR8805629 | 1988-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1336326C true CA1336326C (en) | 1995-07-18 |
Family
ID=9365751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000596597A Expired - Fee Related CA1336326C (en) | 1988-04-27 | 1989-04-13 | Microbeads of diltiazem, a process for their manufacture and a sustained-release pharmaceutical composition containing them |
Country Status (12)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5288505A (en) * | 1991-06-26 | 1994-02-22 | Galephar P.R., Inc., Ltd. | Extended release form of diltiazem |
| KR100221695B1 (ko) * | 1991-08-12 | 1999-09-15 | 그린 마틴, 브라이언 쥐 테슬리 | 약학적 구상 제형 |
| GB2258613B (en) * | 1991-08-12 | 1996-01-10 | Euro Celtique Sa | Pharmaceutical diltiazem formulation |
| JPH08143450A (ja) * | 1994-11-14 | 1996-06-04 | Taiyo Yakuhin Kogyo Kk | 徐放化製剤 |
| FR2742660B1 (fr) * | 1995-12-22 | 1998-04-03 | Ethypharm Lab Prod Ethiques | Nouvelles formes de microgranules a liberation prolongee contenant du diltiazem comme principe actif |
| US7108866B1 (en) | 1999-12-10 | 2006-09-19 | Biovall Laboratories International Srl | Chronotherapeutic diltiazem formulations and the administration thereof |
| ES2530450T3 (es) | 2008-10-02 | 2015-03-03 | Eyesense Ag | Elemento sensor implantable |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57120518A (en) * | 1981-01-19 | 1982-07-27 | Tanabe Seiyaku Co Ltd | Preparation of microcapsule |
| JPS58116414A (ja) * | 1981-12-23 | 1983-07-11 | Yamanouchi Pharmaceut Co Ltd | ニカルジピン持続性製剤用球形顆粒およびその製造法 |
| JPS5916821A (ja) * | 1982-07-16 | 1984-01-28 | Tanabe Seiyaku Co Ltd | 非凝集性マイクロカプセルの製法 |
| IE56999B1 (en) * | 1983-12-22 | 1992-03-11 | Elan Corp Plc | Pharmaceutical formulation |
| LU85943A1 (fr) * | 1985-06-12 | 1987-01-13 | Galephar | Comprimes pharmaceutiques permettant l'administration aisee de pellets, leur preparation et leur utilisation |
| JPS6232166A (ja) * | 1985-08-06 | 1987-02-12 | Mitsui Toatsu Chem Inc | 発泡体加工用粘着剤 |
| LU86077A1 (fr) * | 1985-09-18 | 1987-04-02 | Pharlyse Sa | Nouvelles formes galeniques du verapamil,leur fabrication et medicaments contenant ces nouvelles formes galeniques |
-
1988
- 1988-04-27 FR FR8805629A patent/FR2630647B1/fr not_active Expired - Fee Related
-
1989
- 1989-04-13 CA CA000596597A patent/CA1336326C/en not_active Expired - Fee Related
- 1989-04-19 ZA ZA892871A patent/ZA892871B/xx unknown
- 1989-04-21 NZ NZ228846A patent/NZ228846A/en unknown
- 1989-04-24 AU AU33363/89A patent/AU614056B2/en not_active Ceased
- 1989-04-25 AT AT89401180T patent/ATE72974T1/de active
- 1989-04-25 EP EP89401180A patent/EP0340105B1/fr not_active Expired - Lifetime
- 1989-04-25 ES ES198989401180T patent/ES2032125T3/es not_active Expired - Lifetime
- 1989-04-25 DE DE8989401180T patent/DE68900903D1/de not_active Expired - Fee Related
- 1989-04-26 JP JP1107115A patent/JPH01313431A/ja active Pending
-
1992
- 1992-03-05 GR GR920400339T patent/GR3003988T3/el unknown
- 1992-06-19 MX MX9203020A patent/MX9203020A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU3336389A (en) | 1989-11-02 |
| ZA892871B (en) | 1990-12-28 |
| MX9203020A (es) | 1992-07-01 |
| FR2630647A1 (fr) | 1989-11-03 |
| ATE72974T1 (de) | 1992-03-15 |
| FR2630647B1 (fr) | 1991-08-16 |
| GR3003988T3 (enrdf_load_stackoverflow) | 1993-03-16 |
| ES2032125T3 (es) | 1993-01-01 |
| JPH01313431A (ja) | 1989-12-18 |
| DE68900903D1 (de) | 1992-04-09 |
| NZ228846A (en) | 1991-06-25 |
| AU614056B2 (en) | 1991-08-15 |
| EP0340105A1 (fr) | 1989-11-02 |
| EP0340105B1 (fr) | 1992-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |