HU198497B - Process for producing tricyclic oxazolone derivatives and cardiotonic pharmaceutical compositions comprising same as active ingredient - Google Patents
Process for producing tricyclic oxazolone derivatives and cardiotonic pharmaceutical compositions comprising same as active ingredient Download PDFInfo
- Publication number
- HU198497B HU198497B HU882714A HU271488A HU198497B HU 198497 B HU198497 B HU 198497B HU 882714 A HU882714 A HU 882714A HU 271488 A HU271488 A HU 271488A HU 198497 B HU198497 B HU 198497B
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- formula
- active ingredient
- compound
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- mixture
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- 239000004480 active ingredient Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 4
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical class O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 title description 3
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 230000003177 cardiotonic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 18
- 206010019280 Heart failures Diseases 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- -1 polyethylene Polymers 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 230000000747 cardiac effect Effects 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- 239000011541 reaction mixture Substances 0.000 description 8
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 3
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- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- OKJDEBURSPYOAV-UHFFFAOYSA-N 2h-cyclohepta[c]pyridin-5-yl acetate Chemical compound C1=CC=CC(OC(=O)C)=C2C=CNC=C21 OKJDEBURSPYOAV-UHFFFAOYSA-N 0.000 description 2
- CDZCREIHDRCTHZ-UHFFFAOYSA-N 2h-cyclohepta[c]pyridine Chemical compound C1=CC=CC2=CNC=CC2=C1 CDZCREIHDRCTHZ-UHFFFAOYSA-N 0.000 description 2
- HJGKGMOBSNNJQZ-UHFFFAOYSA-N 4,5-dihydro-3h-[1,3]oxazolo[5,4-f]isoquinolin-2-one Chemical compound C1CC2=CN=CC=C2C2=C1NC(=O)O2 HJGKGMOBSNNJQZ-UHFFFAOYSA-N 0.000 description 2
- RXQZQYFJZQINDS-UHFFFAOYSA-N 6-amino-6h-isoquinolin-5-one Chemical compound N1=CC=C2C(=O)C(N)C=CC2=C1 RXQZQYFJZQINDS-UHFFFAOYSA-N 0.000 description 2
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- 210000001198 duodenum Anatomy 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
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- 239000000839 emulsion Substances 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
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- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 description 1
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- 230000003601 intercostal effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
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- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 208000005333 pulmonary edema Diseases 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000001562 sternum Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Laminated Bodies (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5548587A | 1987-05-29 | 1987-05-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT47585A HUT47585A (en) | 1989-03-28 |
| HU198497B true HU198497B (en) | 1989-10-30 |
Family
ID=21998160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU882714A HU198497B (en) | 1987-05-29 | 1988-05-27 | Process for producing tricyclic oxazolone derivatives and cardiotonic pharmaceutical compositions comprising same as active ingredient |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0293777B1 (https=) |
| JP (1) | JP2640671B2 (https=) |
| KR (1) | KR880013942A (https=) |
| CN (1) | CN1019116B (https=) |
| AT (1) | ATE83777T1 (https=) |
| AU (1) | AU600134B2 (https=) |
| CA (1) | CA1329601C (https=) |
| DE (1) | DE3876859T2 (https=) |
| DK (1) | DK290488A (https=) |
| ES (1) | ES2053621T3 (https=) |
| FI (1) | FI87075C (https=) |
| GR (1) | GR3007091T3 (https=) |
| HU (1) | HU198497B (https=) |
| IL (1) | IL86517A (https=) |
| NO (1) | NO882340L (https=) |
| NZ (1) | NZ224745A (https=) |
| PH (1) | PH25792A (https=) |
| PT (1) | PT87598B (https=) |
| ZA (1) | ZA883659B (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762843A (en) * | 1986-09-15 | 1988-08-09 | Warner-Lambert Company | Hetero [f] fused carbocyclic pyridines as dopaminergic agents |
| MY106964A (en) * | 1988-04-28 | 1995-08-30 | Schering Corp | Fused polycyclic compounds, compositions, methods of manufacture, and their use as paf antagonists, antihistamines and/or antiinflammatory agents. |
| CN102696363A (zh) * | 2012-06-27 | 2012-10-03 | 莱恩农业装备有限公司 | 一种防卡刀碎草机构 |
| CN102696364A (zh) * | 2012-06-28 | 2012-10-03 | 莱恩农业装备有限公司 | 一种卡刀自动调整碎草机构 |
-
1988
- 1988-05-23 NZ NZ224745A patent/NZ224745A/xx unknown
- 1988-05-23 ZA ZA883659A patent/ZA883659B/xx unknown
- 1988-05-25 CA CA000567708A patent/CA1329601C/en not_active Expired - Fee Related
- 1988-05-25 AU AU16624/88A patent/AU600134B2/en not_active Ceased
- 1988-05-26 IL IL86517A patent/IL86517A/xx unknown
- 1988-05-27 DE DE8888108496T patent/DE3876859T2/de not_active Expired - Fee Related
- 1988-05-27 ES ES88108496T patent/ES2053621T3/es not_active Expired - Lifetime
- 1988-05-27 DK DK290488A patent/DK290488A/da not_active Application Discontinuation
- 1988-05-27 JP JP63130056A patent/JP2640671B2/ja not_active Expired - Lifetime
- 1988-05-27 AT AT88108496T patent/ATE83777T1/de active
- 1988-05-27 HU HU882714A patent/HU198497B/hu not_active IP Right Cessation
- 1988-05-27 EP EP88108496A patent/EP0293777B1/en not_active Expired - Lifetime
- 1988-05-27 PT PT87598A patent/PT87598B/pt not_active IP Right Cessation
- 1988-05-27 NO NO882340A patent/NO882340L/no unknown
- 1988-05-27 FI FI882504A patent/FI87075C/fi not_active IP Right Cessation
- 1988-05-28 KR KR1019880006306A patent/KR880013942A/ko not_active Withdrawn
- 1988-05-30 CN CN88103236A patent/CN1019116B/zh not_active Expired
- 1988-05-30 PH PH36992A patent/PH25792A/en unknown
-
1993
- 1993-02-17 GR GR930400324T patent/GR3007091T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI882504A0 (fi) | 1988-05-27 |
| DE3876859T2 (de) | 1993-04-29 |
| FI87075B (fi) | 1992-08-14 |
| ATE83777T1 (de) | 1993-01-15 |
| PH25792A (en) | 1991-11-05 |
| FI87075C (fi) | 1992-11-25 |
| PT87598B (pt) | 1995-03-01 |
| AU600134B2 (en) | 1990-08-02 |
| ZA883659B (en) | 1989-01-25 |
| IL86517A (en) | 1991-11-21 |
| EP0293777A1 (en) | 1988-12-07 |
| JP2640671B2 (ja) | 1997-08-13 |
| AU1662488A (en) | 1988-12-01 |
| ES2053621T3 (es) | 1994-08-01 |
| NO882340D0 (no) | 1988-05-27 |
| NO882340L (no) | 1988-11-30 |
| CA1329601C (en) | 1994-05-17 |
| CN1019116B (zh) | 1992-11-18 |
| DK290488A (da) | 1988-11-30 |
| GR3007091T3 (https=) | 1993-07-30 |
| PT87598A (pt) | 1989-05-31 |
| HUT47585A (en) | 1989-03-28 |
| DK290488D0 (da) | 1988-05-27 |
| NZ224745A (en) | 1990-09-26 |
| EP0293777B1 (en) | 1992-12-23 |
| CN88103236A (zh) | 1988-12-21 |
| DE3876859D1 (de) | 1993-02-04 |
| IL86517A0 (en) | 1988-11-15 |
| FI882504L (fi) | 1988-11-30 |
| KR880013942A (ko) | 1988-12-22 |
| JPS6419080A (en) | 1989-01-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |