CA1338489C - Pharmaceutical preparation containing 2,6-diamino-3-phenyl-azo-pyridine - Google Patents
Pharmaceutical preparation containing 2,6-diamino-3-phenyl-azo-pyridineInfo
- Publication number
- CA1338489C CA1338489C CA000579070A CA579070A CA1338489C CA 1338489 C CA1338489 C CA 1338489C CA 000579070 A CA000579070 A CA 000579070A CA 579070 A CA579070 A CA 579070A CA 1338489 C CA1338489 C CA 1338489C
- Authority
- CA
- Canada
- Prior art keywords
- diamino
- phenyl
- pyridine
- azo
- preparation
- 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
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 title claims abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 241000700605 Viruses Species 0.000 claims abstract description 10
- 206010039491 Sarcoma Diseases 0.000 claims abstract description 8
- 229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 6
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 4
- 239000002674 ointment Substances 0.000 claims description 4
- QQBPIHBUCMDKFG-GEEYTBSJSA-N phenazopyridine hydrochloride Chemical compound Cl.Nc1ccc(\N=N\c2ccccc2)c(N)n1 QQBPIHBUCMDKFG-GEEYTBSJSA-N 0.000 claims description 4
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 4
- 229960003415 propylparaben Drugs 0.000 claims description 4
- 229920002261 Corn starch Polymers 0.000 claims description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 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 claims description 2
- 235000019759 Maize starch Nutrition 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000008101 lactose Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- 239000007788 liquid Substances 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 229960004063 propylene glycol Drugs 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 13
- 239000002207 metabolite Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010027476 Metastases Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- UBTRQPAMLAFXTO-UHFFFAOYSA-N boric acid;3-phenyl-2-(pyridin-2-yldiazenyl)-1h-pyridine-2,6-diamine Chemical compound OB(O)O.C=1C=CC=NC=1N=NC1(N)NC(N)=CC=C1C1=CC=CC=C1 UBTRQPAMLAFXTO-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- -1 salts borate Chemical class 0.000 description 2
- ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- NTNMPDQKBQRDHQ-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-5-methylpyrazol-3-amine Chemical group N1=C(C)C=C(N)N1C1=NC2=CC=CC=C2N1 NTNMPDQKBQRDHQ-UHFFFAOYSA-N 0.000 description 1
- MEHLIOHTSVBWHS-UHFFFAOYSA-N 2-azido-4-phenylpyridin-3-amine Chemical class C1(=CC=CC=C1)C1=C(C(=NC=C1)N=[N+]=[N-])N MEHLIOHTSVBWHS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 238000011281 clinical therapy Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 208000007475 hemolytic anemia Diseases 0.000 description 1
- 231100000334 hepatotoxic Toxicity 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000771 oncological effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 210000000605 viral structure Anatomy 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/655—Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8702446A NL8702446A (nl) | 1987-10-14 | 1987-10-14 | Werkwijze ter bereiding van een veterinair- en humaanmedisch preparaat met antivirale en antitumorale werking, alsmede het in farmaceutisch toepasbare vorm gebrachte preparaat. |
| NLNL-8702446 | 1987-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1338489C true CA1338489C (en) | 1996-07-30 |
Family
ID=19850759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000579070A Expired - Fee Related CA1338489C (en) | 1987-10-14 | 1988-09-30 | Pharmaceutical preparation containing 2,6-diamino-3-phenyl-azo-pyridine |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0312132B1 (enExample) |
| JP (1) | JPH01132525A (enExample) |
| CN (1) | CN1041695A (enExample) |
| AT (1) | ATE84418T1 (enExample) |
| AU (1) | AU619767B2 (enExample) |
| CA (1) | CA1338489C (enExample) |
| DE (1) | DE3877499T2 (enExample) |
| DK (1) | DK574588A (enExample) |
| ES (1) | ES2042715T3 (enExample) |
| GR (1) | GR3009556T3 (enExample) |
| IE (1) | IE60506B1 (enExample) |
| IL (1) | IL87867A (enExample) |
| NL (1) | NL8702446A (enExample) |
| NZ (1) | NZ226360A (enExample) |
| ZA (1) | ZA887181B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6596777B1 (en) | 1997-05-29 | 2003-07-22 | Mcneil-Ppc, Inc. | Moisture containing compositions that are spreadable onto and adherable to biomembranes |
| JP4871293B2 (ja) | 2005-11-15 | 2012-02-08 | 日鍛バルブ株式会社 | 冷媒入り中空ポペットバルブおよびその製造方法 |
| RU2354384C1 (ru) * | 2007-12-28 | 2009-05-10 | Михаил Владимирович Кутушов | Применение органических красителей в качестве средства для лечения онкологических заболеваний |
-
1987
- 1987-10-14 NL NL8702446A patent/NL8702446A/nl not_active Application Discontinuation
-
1988
- 1988-08-24 ES ES88201797T patent/ES2042715T3/es not_active Expired - Lifetime
- 1988-08-24 EP EP19880201797 patent/EP0312132B1/en not_active Expired - Lifetime
- 1988-08-24 DE DE8888201797T patent/DE3877499T2/de not_active Expired - Fee Related
- 1988-08-24 AT AT88201797T patent/ATE84418T1/de not_active IP Right Cessation
- 1988-09-26 ZA ZA887181A patent/ZA887181B/xx unknown
- 1988-09-28 IL IL87867A patent/IL87867A/xx not_active IP Right Cessation
- 1988-09-28 NZ NZ226360A patent/NZ226360A/xx unknown
- 1988-09-30 CA CA000579070A patent/CA1338489C/en not_active Expired - Fee Related
- 1988-10-12 AU AU23663/88A patent/AU619767B2/en not_active Ceased
- 1988-10-14 CN CN88107207A patent/CN1041695A/zh active Pending
- 1988-10-14 DK DK574588A patent/DK574588A/da not_active Application Discontinuation
- 1988-10-14 IE IE311688A patent/IE60506B1/en not_active IP Right Cessation
- 1988-10-14 JP JP63257448A patent/JPH01132525A/ja active Pending
-
1993
- 1993-03-29 GR GR930400677T patent/GR3009556T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0312132A2 (en) | 1989-04-19 |
| DE3877499D1 (de) | 1993-02-25 |
| DK574588A (da) | 1989-04-15 |
| DE3877499T2 (de) | 1993-06-03 |
| IL87867A (en) | 1992-11-15 |
| GR3009556T3 (enExample) | 1994-02-28 |
| IE883116L (en) | 1989-04-14 |
| AU2366388A (en) | 1989-06-01 |
| DK574588D0 (da) | 1988-10-14 |
| ZA887181B (en) | 1989-05-30 |
| NZ226360A (en) | 1990-08-28 |
| ATE84418T1 (de) | 1993-01-15 |
| ES2042715T3 (es) | 1993-12-16 |
| IE60506B1 (en) | 1994-07-27 |
| EP0312132B1 (en) | 1993-01-13 |
| CN1041695A (zh) | 1990-05-02 |
| NL8702446A (nl) | 1989-05-01 |
| IL87867A0 (en) | 1989-03-31 |
| AU619767B2 (en) | 1992-02-06 |
| EP0312132A3 (en) | 1990-04-25 |
| JPH01132525A (ja) | 1989-05-25 |
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