HU209393B - Process for producing new, substituted oxazinoisoquinoline derivates - Google Patents
Process for producing new, substituted oxazinoisoquinoline derivates Download PDFInfo
- Publication number
- HU209393B HU209393B HU913906A HU390691A HU209393B HU 209393 B HU209393 B HU 209393B HU 913906 A HU913906 A HU 913906A HU 390691 A HU390691 A HU 390691A HU 209393 B HU209393 B HU 209393B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- phenyl
- compounds
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- 230000008569 process Effects 0.000 title claims abstract description 7
- RXINFAULMRJDAU-UHFFFAOYSA-N 7h-pyrido[3,4-f][2,1]benzoxazine Chemical class C1=CC2=CC=NC=C2C2=C1NOC=C2 RXINFAULMRJDAU-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 230000003185 calcium uptake Effects 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 210000004958 brain cell Anatomy 0.000 claims abstract 2
- 150000002537 isoquinolines Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical group IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- HLWSLJSWUSSKDL-UHFFFAOYSA-N isoquinoline-1-carbothioamide Chemical class C1=CC=C2C(C(=S)N)=NC=CC2=C1 HLWSLJSWUSSKDL-UHFFFAOYSA-N 0.000 claims description 2
- YZDXFUGIDTUCDA-UHFFFAOYSA-N isoquinoline-1-carboxamide Chemical class C1=CC=C2C(C(=O)N)=NC=CC2=C1 YZDXFUGIDTUCDA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 239000002304 perfume Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
- 206010021143 Hypoxia Diseases 0.000 abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 6
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- 239000012453 solvate Substances 0.000 abstract description 3
- 208000029028 brain injury Diseases 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- -1 1-hydroxymethyl substituent Chemical group 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- 239000000243 solution Substances 0.000 description 7
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- SMANXXCATUTDDT-QPJJXVBHSA-N flunarizine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(C\C=C\C=2C=CC=CC=2)CC1 SMANXXCATUTDDT-QPJJXVBHSA-N 0.000 description 6
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- 239000011780 sodium chloride Substances 0.000 description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 description 5
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- 229960000715 nimodipine Drugs 0.000 description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- UWGBIKPRXRSRNM-UHFFFAOYSA-N cevadine Natural products CC=C(C)/C(=O)OC1CCC2(C)C3CCC4C5(O)CC(O)C6(O)C(CN7CC(C)CCC7C6(C)O)C5(O)CC24OCC13O UWGBIKPRXRSRNM-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
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- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- FXIAKISKQQIKTJ-UHFFFAOYSA-N 2-(3,4-dihydroisoquinolin-1-yl)ethanol Chemical class C1=CC=C2C(CCO)=NCCC2=C1 FXIAKISKQQIKTJ-UHFFFAOYSA-N 0.000 description 3
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
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- CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 3
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- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
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- 239000007924 injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 230000036963 noncompetitive effect Effects 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009822 protein phosphorylation Effects 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229940125794 sodium channel blocker Drugs 0.000 description 1
- 239000003195 sodium channel blocking agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012089 stop solution Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 210000004885 white matter Anatomy 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU913906A HU209393B (en) | 1991-12-12 | 1991-12-12 | Process for producing new, substituted oxazinoisoquinoline derivates |
| US08/244,736 US5494909A (en) | 1991-12-12 | 1992-12-11 | Substituted oxazinoisoquinoline derivatives, pharmaceutical compositions containing them and process for preparing same |
| PCT/HU1992/000053 WO1993012118A1 (en) | 1991-12-12 | 1992-12-11 | Novel substituted oxazinoisoquinoline derivatives, pharmaceutical compositions containing them and process for preparing same |
| AU31705/93A AU3170593A (en) | 1991-12-12 | 1992-12-11 | Novel substituted oxazinoisoquinoline derivatives, pharmaceutical compositions containing them and process for preparing same |
| JP5510763A JPH07501817A (ja) | 1991-12-12 | 1992-12-11 | 新規置換オキサジノイソキノリン誘導体，該誘導体を含有する医薬組成物および該誘導体の製法 |
| EP93900339A EP0620820A1 (en) | 1991-12-12 | 1992-12-11 | Novel substituted oxazinoisoquinoline derivatives, pharmaceutical compositions containing them and process for preparing same |
| TW081110477A TW219364B (https=) | 1991-12-12 | 1992-12-28 | |
| FI942675A FI942675A7 (fi) | 1991-12-12 | 1994-06-07 | Uudet substituoidut oksatsinoisokinoliinijohdannaiset, niitä sisältävät farmaseuttiset koostumukset sekä menetelmä niiden valmistamiseksi |
| NO942181A NO942181D0 (no) | 1991-12-12 | 1994-06-10 | Nye, substituerte oksazinoisokinolinderivater, farmasöytiske preparater inneholdende disse og fremgangsmåte for fremstilling av disse |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU913906A HU209393B (en) | 1991-12-12 | 1991-12-12 | Process for producing new, substituted oxazinoisoquinoline derivates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU913906D0 HU913906D0 (en) | 1992-02-28 |
| HUT63427A HUT63427A (en) | 1993-08-30 |
| HU209393B true HU209393B (en) | 1994-05-30 |
Family
ID=10966001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU913906A HU209393B (en) | 1991-12-12 | 1991-12-12 | Process for producing new, substituted oxazinoisoquinoline derivates |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5494909A (https=) |
| EP (1) | EP0620820A1 (https=) |
| JP (1) | JPH07501817A (https=) |
| AU (1) | AU3170593A (https=) |
| FI (1) | FI942675A7 (https=) |
| HU (1) | HU209393B (https=) |
| NO (1) | NO942181D0 (https=) |
| TW (1) | TW219364B (https=) |
| WO (1) | WO1993012118A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7128759B2 (en) * | 2003-05-19 | 2006-10-31 | Cook Incorporated | Implantable medical device with constrained expansion |
| WO2007022568A1 (en) | 2005-08-25 | 2007-03-01 | Steven Michael Weiss | Reducing myocardial damage and the incidence of arrhythmia arising from loss, reduction or interruption in coronary blood flow |
| CN103651533A (zh) * | 2013-12-30 | 2014-03-26 | 青岛崂乡茶制品有限公司 | 一种新型茶叶种植用农药 |
| CN103651435A (zh) * | 2013-12-30 | 2014-03-26 | 青岛崂乡茶制品有限公司 | 一种环保的茶叶杀虫剂 |
| CN105532682B (zh) * | 2016-02-17 | 2018-03-23 | 陕西先农生物科技有限公司 | 一种含藜芦碱植物源杀虫剂组合物及制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU191301B (en) * | 1984-03-23 | 1987-02-27 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing 1-/hydroxy-methyl/-1,6,7,11b-tetrahydro-2h,4h-/1,3/-oxazino- or -thiazino/4,3-a/isoquinoline -derivatives |
-
1991
- 1991-12-12 HU HU913906A patent/HU209393B/hu not_active IP Right Cessation
-
1992
- 1992-12-11 JP JP5510763A patent/JPH07501817A/ja active Pending
- 1992-12-11 EP EP93900339A patent/EP0620820A1/en not_active Withdrawn
- 1992-12-11 AU AU31705/93A patent/AU3170593A/en not_active Abandoned
- 1992-12-11 US US08/244,736 patent/US5494909A/en not_active Expired - Fee Related
- 1992-12-11 WO PCT/HU1992/000053 patent/WO1993012118A1/en not_active Ceased
- 1992-12-28 TW TW081110477A patent/TW219364B/zh active
-
1994
- 1994-06-07 FI FI942675A patent/FI942675A7/fi not_active Application Discontinuation
- 1994-06-10 NO NO942181A patent/NO942181D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO942181L (https=) | 1994-06-10 |
| NO942181D0 (no) | 1994-06-10 |
| US5494909A (en) | 1996-02-27 |
| HUT63427A (en) | 1993-08-30 |
| HU913906D0 (en) | 1992-02-28 |
| EP0620820A1 (en) | 1994-10-26 |
| AU3170593A (en) | 1993-07-19 |
| FI942675A0 (fi) | 1994-06-07 |
| FI942675A7 (fi) | 1994-06-07 |
| WO1993012118A1 (en) | 1993-06-24 |
| TW219364B (https=) | 1994-01-21 |
| JPH07501817A (ja) | 1995-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |