IL100921A - 9- אמינוטטראהידרואקרידינדיאולים ותרכבות דומות תהליך להכנתם תרכבות ביניים שלהם ותכשירי רוקחות המכילים אותם - Google Patents
9- אמינוטטראהידרואקרידינדיאולים ותרכבות דומות תהליך להכנתם תרכבות ביניים שלהם ותכשירי רוקחות המכילים אותםInfo
- Publication number
- IL100921A IL100921A IL10092192A IL10092192A IL100921A IL 100921 A IL100921 A IL 100921A IL 10092192 A IL10092192 A IL 10092192A IL 10092192 A IL10092192 A IL 10092192A IL 100921 A IL100921 A IL 100921A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen
- compound
- formula
- loweralkyl
- amino
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 230000008569 process Effects 0.000 title claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- OHXAQTABIOETBM-UHFFFAOYSA-N 9-amino-1,2,3,4-tetrahydroacridine-1,2-diol Chemical class C1=CC=C2C(N)=C(C(O)C(O)CC3)C3=NC2=C1 OHXAQTABIOETBM-UHFFFAOYSA-N 0.000 title description 3
- 239000000543 intermediate Substances 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 35
- -1 loweralkyl Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 11
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- 230000003287 optical effect Effects 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 230000007074 memory dysfunction Effects 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 5
- IYHDVHNLLXAHLY-UHFFFAOYSA-N 9-amino-1,2,3,4-tetrahydroacridine-1,4-diol Chemical compound C1=CC=C2C(N)=C(C(O)CCC3O)C3=NC2=C1 IYHDVHNLLXAHLY-UHFFFAOYSA-N 0.000 claims description 4
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- OUZJMSBCLSBRRD-UHFFFAOYSA-N 9-amino-1,2,3,4-tetrahydroacridine-1,3-diol Chemical compound C1=CC=C2C(N)=C(C(O)CC(O)C3)C3=NC2=C1 OUZJMSBCLSBRRD-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims 4
- 230000008018 melting Effects 0.000 claims 4
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- 208000024827 Alzheimer disease Diseases 0.000 abstract description 3
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 241001465754 Metazoa Species 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 14
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- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
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- 238000010992 reflux Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
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- 239000011541 reaction mixture Substances 0.000 description 6
- 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 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- IPFDTWHBEBJTLE-UHFFFAOYSA-N 2h-acridin-1-one Chemical class C1=CC=C2C=C3C(=O)CC=CC3=NC2=C1 IPFDTWHBEBJTLE-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 208000026139 Memory disease Diseases 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 150000007513 acids Chemical class 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL117795A IL117795A (he) | 1991-02-13 | 1992-02-11 | 6,7-דיהדרו-3- )2-ניטרופניל( 1, 2- בנזיסוקסאזול-h) 54(-אונים ומלחים מוספים המקובלים בתכשירים רפואיים |
| IL11779596A IL117795A0 (en) | 1991-02-13 | 1996-04-02 | Dihydrobenzisoxazolines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/654,691 US5210087A (en) | 1991-02-13 | 1991-02-13 | 9-aminotetrahydroacridines and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL100921A true IL100921A (he) | 1998-12-27 |
Family
ID=24625869
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL117795A IL117795A (he) | 1991-02-13 | 1992-02-11 | 6,7-דיהדרו-3- )2-ניטרופניל( 1, 2- בנזיסוקסאזול-h) 54(-אונים ומלחים מוספים המקובלים בתכשירים רפואיים |
| IL10092192A IL100921A (he) | 1991-02-13 | 1992-02-11 | 9- אמינוטטראהידרואקרידינדיאולים ותרכבות דומות תהליך להכנתם תרכבות ביניים שלהם ותכשירי רוקחות המכילים אותם |
| IL11779596A IL117795A0 (en) | 1991-02-13 | 1996-04-02 | Dihydrobenzisoxazolines |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL117795A IL117795A (he) | 1991-02-13 | 1992-02-11 | 6,7-דיהדרו-3- )2-ניטרופניל( 1, 2- בנזיסוקסאזול-h) 54(-אונים ומלחים מוספים המקובלים בתכשירים רפואיים |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11779596A IL117795A0 (en) | 1991-02-13 | 1996-04-02 | Dihydrobenzisoxazolines |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US5210087A (he) |
| EP (1) | EP0499231B1 (he) |
| JP (1) | JPH07121915B2 (he) |
| KR (1) | KR100223132B1 (he) |
| AT (1) | ATE153331T1 (he) |
| AU (1) | AU664165B2 (he) |
| BR (1) | BR9200475A (he) |
| CA (1) | CA2061084A1 (he) |
| CZ (1) | CZ281927B6 (he) |
| DE (1) | DE69219801T2 (he) |
| DK (1) | DK0499231T3 (he) |
| ES (1) | ES2102417T3 (he) |
| FI (2) | FI96308C (he) |
| GR (1) | GR3024310T3 (he) |
| HU (1) | HU219451B (he) |
| IE (1) | IE920459A1 (he) |
| IL (3) | IL117795A (he) |
| MX (1) | MX9200607A (he) |
| NO (1) | NO177933C (he) |
| NZ (3) | NZ241586A (he) |
| PL (6) | PL166939B1 (he) |
| RO (1) | RO112354B1 (he) |
| RU (1) | RU2083564C1 (he) |
| TW (1) | TW221426B (he) |
| ZA (1) | ZA921004B (he) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210087A (en) * | 1991-02-13 | 1993-05-11 | Hoechst-Roussel Pharmaceuticals Inc. | 9-aminotetrahydroacridines and related compounds |
| GB2264707A (en) * | 1991-06-18 | 1993-09-08 | Roger Michael Marchbanks | Acridine derivatives for treating alzheimer's disease |
| ES2059263B1 (es) * | 1992-10-27 | 1995-10-01 | Vita Invest Sa | Procedimiento para la obtencion del (+)-9-amino-1,2,3,4-tetrahidroacridin-1-ol. |
| US5434170A (en) * | 1993-12-23 | 1995-07-18 | Andrulis Pharmaceuticals Corp. | Method for treating neurocognitive disorders |
| ES2144353B1 (es) * | 1997-12-26 | 2001-01-01 | Consejo Superior Investigacion | Nuevos analogos de tacrina: potenciales agentes neuroprotectores para las enfermedades de alzheimer y parkinson. su procedimiento de obtencion. |
| WO2003076419A1 (fr) | 2002-03-08 | 2003-09-18 | Japan Science And Technology Agency | Derives d'isoxazole et procede de fabrication correspondant |
| RU2616247C1 (ru) * | 2016-03-28 | 2017-04-13 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Северо-Осетинский государственный университет имени Коста Левановича Хетагурова" (СОГУ) | Твердая лекарственная форма, обладающая холинопозитивным действием, на основе 9-бутиламино-3,3-диметил-1,2,4-тригидроакридина |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232945A (en) * | 1962-08-13 | 1966-02-01 | S E Massengill Company | 7,8,9,10-tetrahalo-6h-cyclohepta-(b)-quinolines |
| US4695573A (en) * | 1984-10-25 | 1987-09-22 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| US4631286A (en) * | 1984-10-25 | 1986-12-23 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| DE3582995D1 (de) * | 1984-10-25 | 1991-07-04 | Hoechst Roussel Pharma | 9-amino-1,2,3,4-tetrahydroacridin-1-ol und verwandte verbindungen, verfahren zu ihrer herstellung und verwendung als arzneimittel. |
| IL87861A0 (en) * | 1987-10-05 | 1989-03-31 | Pfizer | 4-aminopyridine derivatives |
| WO1989002739A1 (en) * | 1987-10-05 | 1989-04-06 | Pfizer Inc. | 4-aminopyridine derivatives |
| GB8827704D0 (en) * | 1988-11-28 | 1988-12-29 | Fujisawa Pharmaceutical Co | New acridine derivatives & processes for their production |
| US5441727A (en) * | 1989-06-21 | 1995-08-15 | The Procter & Gamble Company | Diketone deodorant composition and method of deodorization |
| US5053513A (en) * | 1990-03-29 | 1991-10-01 | Hoechst-Roussel Pharmaceuticals Incorporated | Method of reducing a carbonyl containing acridine |
| US5210087A (en) * | 1991-02-13 | 1993-05-11 | Hoechst-Roussel Pharmaceuticals Inc. | 9-aminotetrahydroacridines and related compounds |
| GB2264707A (en) * | 1991-06-18 | 1993-09-08 | Roger Michael Marchbanks | Acridine derivatives for treating alzheimer's disease |
-
1991
- 1991-02-13 US US07/654,691 patent/US5210087A/en not_active Expired - Fee Related
-
1992
- 1992-01-30 TW TW081100687A patent/TW221426B/zh active
- 1992-02-10 RO RO92-200124A patent/RO112354B1/ro unknown
- 1992-02-11 NZ NZ241586A patent/NZ241586A/en unknown
- 1992-02-11 IL IL117795A patent/IL117795A/he not_active IP Right Cessation
- 1992-02-11 NZ NZ270647A patent/NZ270647A/en unknown
- 1992-02-11 IL IL10092192A patent/IL100921A/he not_active IP Right Cessation
- 1992-02-11 NZ NZ260694A patent/NZ260694A/en unknown
- 1992-02-11 FI FI920566A patent/FI96308C/fi active
- 1992-02-12 CA CA002061084A patent/CA2061084A1/en not_active Abandoned
- 1992-02-12 KR KR1019920002007A patent/KR100223132B1/ko not_active IP Right Cessation
- 1992-02-12 CZ CS92426A patent/CZ281927B6/cs unknown
- 1992-02-12 BR BR929200475A patent/BR9200475A/pt not_active Application Discontinuation
- 1992-02-12 IE IE045992A patent/IE920459A1/en not_active IP Right Cessation
- 1992-02-12 PL PL92296320A patent/PL166939B1/pl unknown
- 1992-02-12 PL PL92296319A patent/PL168153B1/pl unknown
- 1992-02-12 DK DK92102332.1T patent/DK0499231T3/da active
- 1992-02-12 HU HU9200423A patent/HU219451B/hu not_active IP Right Cessation
- 1992-02-12 JP JP4024914A patent/JPH07121915B2/ja not_active Expired - Fee Related
- 1992-02-12 ES ES92102332T patent/ES2102417T3/es not_active Expired - Lifetime
- 1992-02-12 RU SU5010876/04A patent/RU2083564C1/ru not_active IP Right Cessation
- 1992-02-12 MX MX9200607A patent/MX9200607A/es not_active IP Right Cessation
- 1992-02-12 AT AT92102332T patent/ATE153331T1/de not_active IP Right Cessation
- 1992-02-12 PL PL92308050A patent/PL168906B1/pl unknown
- 1992-02-12 PL PL92308049A patent/PL168861B1/pl unknown
- 1992-02-12 AU AU10903/92A patent/AU664165B2/en not_active Ceased
- 1992-02-12 PL PL92293443A patent/PL169095B1/pl unknown
- 1992-02-12 DE DE69219801T patent/DE69219801T2/de not_active Expired - Fee Related
- 1992-02-12 EP EP92102332A patent/EP0499231B1/en not_active Expired - Lifetime
- 1992-02-12 PL PL92308048A patent/PL168862B1/pl unknown
- 1992-02-12 ZA ZA921004A patent/ZA921004B/xx unknown
- 1992-02-12 NO NO920547A patent/NO177933C/no not_active IP Right Cessation
-
1993
- 1993-03-01 US US08/024,037 patent/US5382594A/en not_active Expired - Fee Related
-
1994
- 1994-12-13 FI FI945854A patent/FI97056C/fi active
-
1995
- 1995-05-31 US US08/451,327 patent/US5502203A/en not_active Expired - Fee Related
-
1996
- 1996-04-02 IL IL11779596A patent/IL117795A0/xx unknown
-
1997
- 1997-07-30 GR GR970401959T patent/GR3024310T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |