CA1124989A - Heteropolyanion compounds containing tungsten combined with antimony - Google Patents
Heteropolyanion compounds containing tungsten combined with antimonyInfo
- Publication number
- CA1124989A CA1124989A CA292,227A CA292227A CA1124989A CA 1124989 A CA1124989 A CA 1124989A CA 292227 A CA292227 A CA 292227A CA 1124989 A CA1124989 A CA 1124989A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- solution
- ammonium
- aqueous solution
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 68
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 title claims description 10
- 229910052787 antimony Inorganic materials 0.000 title description 4
- 229910052721 tungsten Inorganic materials 0.000 title description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 title description 3
- 239000010937 tungsten Substances 0.000 title description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 12
- 239000011734 sodium Substances 0.000 claims abstract description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 10
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- 239000000243 solution Substances 0.000 claims description 42
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 30
- 239000007864 aqueous solution Substances 0.000 claims description 30
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 25
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 16
- 150000002500 ions Chemical class 0.000 claims description 14
- 239000001103 potassium chloride Substances 0.000 claims description 14
- 235000011164 potassium chloride Nutrition 0.000 claims description 14
- 150000003863 ammonium salts Chemical class 0.000 claims description 13
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 claims description 12
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 10
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000012047 saturated solution Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 229910020494 K2WO4 Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910001415 sodium ion Inorganic materials 0.000 claims description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims description 2
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims 3
- YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 claims 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 2
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 1
- 241000700605 Viruses Species 0.000 abstract description 36
- 238000011282 treatment Methods 0.000 abstract description 21
- 208000032839 leukemia Diseases 0.000 abstract description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 11
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 6
- 229910052751 metal Inorganic materials 0.000 abstract description 6
- 239000002184 metal Substances 0.000 abstract description 6
- 239000003513 alkali Substances 0.000 abstract description 5
- 208000037273 Pathologic Processes Diseases 0.000 abstract description 3
- 208000036142 Viral infection Diseases 0.000 abstract description 3
- 230000009054 pathological process Effects 0.000 abstract description 3
- 230000009385 viral infection Effects 0.000 abstract description 3
- 206010039491 Sarcoma Diseases 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- JVUIPFRSLYDCCX-UHFFFAOYSA-O azanium;antimony(3+);oxygen(2-);tungsten Chemical compound [NH4+].[O-2].[O-2].[O-2].[O-2].[O-2].[Sb+3].[W] JVUIPFRSLYDCCX-UHFFFAOYSA-O 0.000 description 45
- 210000000952 spleen Anatomy 0.000 description 21
- 241001465754 Metazoa Species 0.000 description 20
- 230000000694 effects Effects 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- 206010041660 Splenomegaly Diseases 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 241000699666 Mus <mouse, genus> Species 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 229920000447 polyanionic polymer Polymers 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- 229940079322 interferon Drugs 0.000 description 8
- 230000004083 survival effect Effects 0.000 description 7
- 230000003612 virological effect Effects 0.000 description 7
- 102000014150 Interferons Human genes 0.000 description 6
- 108010050904 Interferons Proteins 0.000 description 6
- 238000007912 intraperitoneal administration Methods 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 150000001455 metallic ions Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- 101000874159 Mus musculus Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Proteins 0.000 description 3
- -1 calcium or barium Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229910001414 potassium ion Inorganic materials 0.000 description 3
- 241000710188 Encephalomyocarditis virus Species 0.000 description 2
- 238000001237 Raman spectrum Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 208000008601 Polycythemia Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000009109 curative therapy Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 231100001251 short-term toxicity Toxicity 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G41/00—Compounds of tungsten
- C01G41/006—Compounds containing tungsten, with or without oxygen or hydrogen, and containing two or more other elements
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2002/00—Crystal-structural characteristics
- C01P2002/80—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70
- C01P2002/82—Crystal-structural characteristics defined by measured data other than those specified in group C01P2002/70 by IR- or Raman-data
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/32—Thermal properties
- C01P2006/37—Stability against thermal decomposition
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Inorganic Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7636498A FR2372633A2 (fr) | 1976-12-03 | 1976-12-03 | Compose d'heteropolyanions contenant du tungstene combine a de l'antimoine, leur obtention et leurs applications |
| FR7636.498 | 1976-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1124989A true CA1124989A (en) | 1982-06-08 |
Family
ID=9180628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA292,227A Expired CA1124989A (en) | 1976-12-03 | 1977-12-02 | Heteropolyanion compounds containing tungsten combined with antimony |
Country Status (7)
| Country | Link |
|---|---|
| JP (2) | JPS5392400A (enrdf_load_stackoverflow) |
| BE (1) | BE861233A (enrdf_load_stackoverflow) |
| CA (1) | CA1124989A (enrdf_load_stackoverflow) |
| CH (1) | CH628005A5 (enrdf_load_stackoverflow) |
| DE (2) | DE2753312A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2372633A2 (enrdf_load_stackoverflow) |
| GB (1) | GB1575940A (enrdf_load_stackoverflow) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0629191B2 (ja) * | 1984-09-04 | 1994-04-20 | 株式会社ポリトロニクス | 抗腫瘍剤、抗ウィルス剤 |
| DE3542165A1 (de) * | 1984-12-03 | 1986-07-10 | Centre National De La Recherche Scientifique (C.N.R.S.), Paris | Medikament zur behandlung des syndroms der erworbenen immunschwaeche (aids) und entsprechende pharmazeutische zusammensetzungen |
| FR2587214B1 (fr) * | 1985-09-13 | 1987-12-24 | Pasteur Institut | Anticoagulants constitues d'heteropolyanions tungstiques et utilisation de ces heteropolyanions a la preparation de medicaments anticoagulants |
| JP2707252B2 (ja) * | 1987-08-03 | 1998-01-28 | 利博 山瀬 | 抗ウィルス剤 |
| WO1990006756A1 (en) * | 1988-12-16 | 1990-06-28 | Terumo Kabushiki Kaisha | Antiviral agent |
| US5051414A (en) * | 1989-08-03 | 1991-09-24 | Dupont Merck Pharmaceutical Company | Inhibition of HIV and other retroviruses by polyoxoanions |
| WO1994012192A1 (en) * | 1992-12-01 | 1994-06-09 | Commonwealth Scientific And Industrial Research Organisation | Antiviral agents |
| DE4336642C2 (de) * | 1993-10-22 | 1995-08-10 | Deutsches Rheuma Forschungszen | Verwendung von Vanadiumverbindungen mit antiviraler Wirkung |
| JP2005281299A (ja) * | 2004-03-01 | 2005-10-13 | Paratex Japan:Kk | 抗菌・防カビ剤及びそれを用いた塗料組成物 |
| JP4824536B2 (ja) * | 2006-12-12 | 2011-11-30 | 株式会社サトー | 応募券用シールおよび応募券用シール貼付け方法 |
-
1976
- 1976-12-03 FR FR7636498A patent/FR2372633A2/fr active Granted
-
1977
- 1977-11-25 BE BE182955A patent/BE861233A/xx not_active IP Right Cessation
- 1977-11-30 DE DE19772753312 patent/DE2753312A1/de not_active Ceased
- 1977-11-30 DE DE19772760338 patent/DE2760338A1/de active Pending
- 1977-12-02 GB GB50311/77A patent/GB1575940A/en not_active Expired
- 1977-12-02 CA CA292,227A patent/CA1124989A/en not_active Expired
- 1977-12-02 CH CH1480377A patent/CH628005A5/fr not_active IP Right Cessation
- 1977-12-03 JP JP14562577A patent/JPS5392400A/ja active Granted
-
1985
- 1985-11-08 JP JP60249093A patent/JPS61165336A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61165336A (ja) | 1986-07-26 |
| FR2372633B2 (enrdf_load_stackoverflow) | 1980-06-27 |
| FR2372633A2 (fr) | 1978-06-30 |
| DE2753312A1 (de) | 1978-06-08 |
| GB1575940A (en) | 1980-10-01 |
| JPH0212933B2 (enrdf_load_stackoverflow) | 1990-03-30 |
| JPS5392400A (en) | 1978-08-14 |
| JPS6221732B2 (enrdf_load_stackoverflow) | 1987-05-14 |
| DE2760338A1 (enrdf_load_stackoverflow) | 1986-03-20 |
| CH628005A5 (en) | 1982-02-15 |
| BE861233A (fr) | 1978-05-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |