CA2013443A1 - Pharmaceutical compositions and their use in the treatment of parasitoses - Google Patents
Pharmaceutical compositions and their use in the treatment of parasitosesInfo
- Publication number
- CA2013443A1 CA2013443A1 CA002013443A CA2013443A CA2013443A1 CA 2013443 A1 CA2013443 A1 CA 2013443A1 CA 002013443 A CA002013443 A CA 002013443A CA 2013443 A CA2013443 A CA 2013443A CA 2013443 A1 CA2013443 A1 CA 2013443A1
- Authority
- CA
- Canada
- Prior art keywords
- ifn
- anthelminthic
- gamma
- mebendazole
- pharmaceutically acceptable
- 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.)
- Abandoned
Links
- 238000011282 treatment Methods 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 230000000507 anthelmentic effect Effects 0.000 claims abstract description 36
- 241000124008 Mammalia Species 0.000 claims abstract description 12
- OPXLLQIJSORQAM-UHFFFAOYSA-N mebendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(=O)C1=CC=CC=C1 OPXLLQIJSORQAM-UHFFFAOYSA-N 0.000 claims description 61
- 229960003439 mebendazole Drugs 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 23
- 208000015181 infectious disease Diseases 0.000 claims description 19
- 238000012270 DNA recombination Methods 0.000 claims description 11
- 241000282414 Homo sapiens Species 0.000 claims description 11
- 241000894007 species Species 0.000 claims description 7
- 241000244163 Echinococcus multilocularis Species 0.000 claims description 6
- 150000001556 benzimidazoles Chemical class 0.000 claims description 6
- 244000079386 endoparasite Species 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 208000030852 Parasitic disease Diseases 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 9
- 239000004480 active ingredient Substances 0.000 claims 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 208000031513 cyst Diseases 0.000 description 34
- 238000012360 testing method Methods 0.000 description 29
- 241001465754 Metazoa Species 0.000 description 28
- 206010028851 Necrosis Diseases 0.000 description 17
- 230000017074 necrotic cell death Effects 0.000 description 17
- 230000007850 degeneration Effects 0.000 description 16
- 206010011732 Cyst Diseases 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 230000035558 fertility Effects 0.000 description 13
- 238000002560 therapeutic procedure Methods 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 230000036512 infertility Effects 0.000 description 10
- 241000699694 Gerbillinae Species 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 241000244160 Echinococcus Species 0.000 description 7
- 101710098398 Probable alanine aminotransferase, mitochondrial Proteins 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 210000002966 serum Anatomy 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 102000004243 Tubulin Human genes 0.000 description 4
- 108090000704 Tubulin Proteins 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000001338 necrotic effect Effects 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 206010014096 Echinococciasis Diseases 0.000 description 3
- 208000009366 Echinococcosis Diseases 0.000 description 3
- 241000215542 Microtus arvalis Species 0.000 description 3
- 241001529936 Murinae Species 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000003745 diagnosis Methods 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 230000002147 killing effect Effects 0.000 description 3
- 230000001418 larval effect Effects 0.000 description 3
- 244000045947 parasite Species 0.000 description 3
- 238000004393 prognosis Methods 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 206010019659 Hepatic echinococciasis Diseases 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 241000699696 Meriones Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- 206010048685 Oral infection Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 210000000683 abdominal cavity Anatomy 0.000 description 2
- 201000003894 alveolar echinococcosis Diseases 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 239000000890 drug combination Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000001524 infective effect Effects 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 230000002101 lytic effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 210000003739 neck Anatomy 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000009097 single-agent therapy Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- 230000002407 ATP formation Effects 0.000 description 1
- 241000244188 Ascaris suum Species 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 235000006696 Catha edulis Nutrition 0.000 description 1
- 240000007681 Catha edulis Species 0.000 description 1
- 241000766026 Coregonus nasus Species 0.000 description 1
- 241000244152 Cyclophyllidea Species 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920002527 Glycogen Polymers 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 102000008070 Interferon-gamma Human genes 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 description 1
- RAOCRURYZCVHMG-UHFFFAOYSA-N N-(6-propoxy-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCOC1=CC=C2N=C(NC(=O)OC)NC2=C1 RAOCRURYZCVHMG-UHFFFAOYSA-N 0.000 description 1
- 241000906034 Orthops Species 0.000 description 1
- 244000302697 Phragmites karka Species 0.000 description 1
- 241000942597 Scolex Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 208000035472 Zoonoses Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 229960002669 albendazole Drugs 0.000 description 1
- HXHWSAZORRCQMX-UHFFFAOYSA-N albendazole Chemical compound CCCSC1=CC=C2NC(NC(=O)OC)=NC2=C1 HXHWSAZORRCQMX-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012984 antibiotic solution Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 208000037887 cell injury Diseases 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229960001020 ciclobendazole Drugs 0.000 description 1
- OXLKOMYHDYVIDM-UHFFFAOYSA-N ciclobendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1CC1 OXLKOMYHDYVIDM-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 210000004292 cytoskeleton Anatomy 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000002354 daily effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 229960005473 fenbendazole Drugs 0.000 description 1
- HDDSHPAODJUKPD-UHFFFAOYSA-N fenbendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1SC1=CC=CC=C1 HDDSHPAODJUKPD-UHFFFAOYSA-N 0.000 description 1
- 229960004500 flubendazole Drugs 0.000 description 1
- CPEUVMUXAHMANV-UHFFFAOYSA-N flubendazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=C(F)C=C1 CPEUVMUXAHMANV-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940096919 glycogen Drugs 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940090044 injection Drugs 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 229960003130 interferon gamma Drugs 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 230000011278 mitosis Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229960004454 oxfendazole Drugs 0.000 description 1
- BEZZFPOZAYTVHN-UHFFFAOYSA-N oxfendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1S(=O)C1=CC=CC=C1 BEZZFPOZAYTVHN-UHFFFAOYSA-N 0.000 description 1
- 229960002762 oxibendazole Drugs 0.000 description 1
- -1 pH 7.5 Chemical compound 0.000 description 1
- 229950007337 parbendazole Drugs 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 210000003281 pleural cavity Anatomy 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 208000037972 tropical disease Diseases 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 206010048282 zoonosis Diseases 0.000 description 1
Classifications
-
- 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
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/21—Interferons [IFN]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Measuring Pulse, Heart Rate, Blood Pressure Or Blood Flow (AREA)
- Measurement Of Force In General (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3910568A DE3910568A1 (de) | 1989-04-01 | 1989-04-01 | Arzneimittelkombinationen und ihre verwendung zur behandlung von parasitosen |
| DEP3910568.7 | 1989-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2013443A1 true CA2013443A1 (en) | 1990-10-01 |
Family
ID=6377615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002013443A Abandoned CA2013443A1 (en) | 1989-04-01 | 1990-03-30 | Pharmaceutical compositions and their use in the treatment of parasitoses |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5178857A (enExample) |
| EP (1) | EP0391224B1 (enExample) |
| AT (1) | ATE96039T1 (enExample) |
| CA (1) | CA2013443A1 (enExample) |
| DD (1) | DD293960A5 (enExample) |
| DE (2) | DE3910568A1 (enExample) |
| DK (1) | DK0391224T3 (enExample) |
| ES (1) | ES2059859T3 (enExample) |
| FI (1) | FI901607A7 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0721780A3 (en) * | 1994-12-16 | 1997-12-17 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Agent for promoting platelet and/or leukocyte production |
| CN110716035B (zh) * | 2018-07-12 | 2023-02-28 | 中国疾病预防控制中心寄生虫病预防控制所 | 基于棘球蚴微管蛋白为靶点的抗棘球蚴病高通量药物筛选方法 |
| CN118976113B (zh) * | 2024-10-12 | 2025-09-02 | 新疆医科大学第一附属医院 | 脂肪酸酰胺水解酶抑制剂pf-3845作为制备治疗泡型包虫病药物的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4510144A (en) * | 1981-08-26 | 1985-04-09 | Newport Pharmaceuticals International | Methods of imparting immunomodulating activity with dihydrothiazolo purine derivatives |
-
1989
- 1989-04-01 DE DE3910568A patent/DE3910568A1/de active Granted
-
1990
- 1990-03-28 ES ES90105871T patent/ES2059859T3/es not_active Expired - Lifetime
- 1990-03-28 DE DE90105871T patent/DE59003111D1/de not_active Expired - Lifetime
- 1990-03-28 EP EP90105871A patent/EP0391224B1/de not_active Expired - Lifetime
- 1990-03-28 AT AT90105871T patent/ATE96039T1/de not_active IP Right Cessation
- 1990-03-28 DK DK90105871.9T patent/DK0391224T3/da active
- 1990-03-30 US US07/501,812 patent/US5178857A/en not_active Expired - Lifetime
- 1990-03-30 FI FI901607A patent/FI901607A7/fi not_active Application Discontinuation
- 1990-03-30 CA CA002013443A patent/CA2013443A1/en not_active Abandoned
- 1990-03-30 DD DD90339252A patent/DD293960A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3910568C2 (enExample) | 1991-03-07 |
| FI901607A0 (fi) | 1990-03-30 |
| EP0391224A2 (de) | 1990-10-10 |
| EP0391224B1 (de) | 1993-10-20 |
| EP0391224A3 (de) | 1991-08-07 |
| ATE96039T1 (de) | 1993-11-15 |
| DE59003111D1 (de) | 1993-11-25 |
| ES2059859T3 (es) | 1994-11-16 |
| DK0391224T3 (da) | 1993-12-06 |
| DE3910568A1 (de) | 1990-10-04 |
| DD293960A5 (de) | 1991-09-19 |
| FI901607A7 (fi) | 1990-10-02 |
| US5178857A (en) | 1993-01-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |