SA92130141B1 - مشتقات رباعي هيدروكربازول teterahydrocarbazole كعوامل مساعدة لمستقبل - Google Patents
مشتقات رباعي هيدروكربازول teterahydrocarbazole كعوامل مساعدة لمستقبل Download PDFInfo
- Publication number
- SA92130141B1 SA92130141B1 SA92130141A SA92130141A SA92130141B1 SA 92130141 B1 SA92130141 B1 SA 92130141B1 SA 92130141 A SA92130141 A SA 92130141A SA 92130141 A SA92130141 A SA 92130141A SA 92130141 B1 SA92130141 B1 SA 92130141B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- compound
- tetrahydrocarbazole
- amino
- oxalate
- hydrochloride
- Prior art date
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- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 229
- 238000000034 method Methods 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 14
- 206010027599 migraine Diseases 0.000 claims abstract description 11
- 206010019233 Headaches Diseases 0.000 claims abstract description 6
- 231100000869 headache Toxicity 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 208000006561 Cluster Headache Diseases 0.000 claims description 3
- 208000018912 cluster headache syndrome Diseases 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 2
- 208000019553 vascular disease Diseases 0.000 claims description 2
- -1 nitro, hydroxy Chemical group 0.000 abstract description 65
- 125000000217 alkyl group Chemical group 0.000 abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 18
- 239000001257 hydrogen Substances 0.000 abstract description 18
- 230000008569 process Effects 0.000 abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
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- 229940079593 drug Drugs 0.000 abstract description 5
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- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 19
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 12
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
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- 239000000706 filtrate Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- PWUJQPNLEZZILN-UHFFFAOYSA-N 2-(4-oxocyclohexyl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)CC1 PWUJQPNLEZZILN-UHFFFAOYSA-N 0.000 description 4
- LMBFUMXVHAJSNJ-UHFFFAOYSA-N 4-(dimethylamino)cyclohexan-1-one Chemical compound CN(C)C1CCC(=O)CC1 LMBFUMXVHAJSNJ-UHFFFAOYSA-N 0.000 description 4
- APSDTEHUYIJMPZ-UHFFFAOYSA-N 9h-carbazole;hydrochloride Chemical compound Cl.C1=CC=C2C3=CC=CC=C3NC2=C1 APSDTEHUYIJMPZ-UHFFFAOYSA-N 0.000 description 4
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
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- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
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- URAVRPANNFWXAZ-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine;pyridine Chemical compound C1=CC=NC=C1.CN(C)C1=CC=CC=N1 URAVRPANNFWXAZ-UHFFFAOYSA-N 0.000 description 1
- YDUKQCJFYLORQF-UHFFFAOYSA-N n-(4-hydrazinylphenyl)acetamide;hydrochloride Chemical compound Cl.CC(=O)NC1=CC=C(NN)C=C1 YDUKQCJFYLORQF-UHFFFAOYSA-N 0.000 description 1
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- 235000011007 phosphoric acid Nutrition 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
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- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
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- 235000010344 sodium nitrate Nutrition 0.000 description 1
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- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
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- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB919113802A GB9113802D0 (en) | 1991-06-26 | 1991-06-26 | Medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SA92130141B1 true SA92130141B1 (ar) | 2005-12-18 |
Family
ID=10697363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SA92130141A SA92130141B1 (ar) | 1991-06-26 | 1992-10-04 | مشتقات رباعي هيدروكربازول teterahydrocarbazole كعوامل مساعدة لمستقبل |
Country Status (34)
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|---|---|
| US (2) | US5464864A (https=) |
| EP (1) | EP0591280B1 (https=) |
| JP (1) | JP3261502B2 (https=) |
| KR (1) | KR100251571B1 (https=) |
| CN (1) | CN1034072C (https=) |
| AP (1) | AP344A (https=) |
| AT (1) | ATE170746T1 (https=) |
| BR (2) | BR9206237A (https=) |
| CA (1) | CA2113726C (https=) |
| CZ (3) | CZ282327B6 (https=) |
| DE (2) | DE69226953T2 (https=) |
| DK (1) | DK0591280T3 (https=) |
| FI (1) | FI103967B1 (https=) |
| GB (1) | GB9113802D0 (https=) |
| HU (1) | HU218907B (https=) |
| IE (1) | IE922062A1 (https=) |
| IL (4) | IL117105A (https=) |
| LU (1) | LU90939I2 (https=) |
| MA (1) | MA22563A1 (https=) |
| MX (1) | MX9203444A (https=) |
| NL (1) | NL300103I2 (https=) |
| NO (2) | NO304774B1 (https=) |
| NZ (1) | NZ243288A (https=) |
| PL (3) | PL169392B1 (https=) |
| PT (1) | PT100620B (https=) |
| RU (1) | RU2137474C1 (https=) |
| SA (1) | SA92130141B1 (https=) |
| SG (1) | SG47877A1 (https=) |
| SI (1) | SI9200125B (https=) |
| SK (3) | SK280906B6 (https=) |
| TW (1) | TW214544B (https=) |
| UA (1) | UA41254C2 (https=) |
| WO (1) | WO1993000086A1 (https=) |
| ZA (1) | ZA924658B (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9211277D0 (en) | 1992-05-28 | 1992-07-15 | Glaxo Group Inc | Pharmaceutical compositions |
| GB9226530D0 (en) * | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| US5616603A (en) * | 1995-05-26 | 1997-04-01 | Smithkline Beecham Plc | Enantiomers of carbazole derivatives as 5-HT1 -like agonists |
| GB9226566D0 (en) * | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| US5618948A (en) * | 1995-05-26 | 1997-04-08 | Smithkline Beecham P.L.C. | Process for preparing an enantiomer of a carbazole derivative |
| EP0749962B1 (en) * | 1995-06-23 | 2000-11-02 | Eli Lilly And Company | 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta(7,6-B)indoles |
| US5917054A (en) * | 1995-07-18 | 1999-06-29 | Smithkline Beecham P.L.C. | Process for preparing enantiomers of carbazole derivatives as 5-HT1 -like agonists |
| US5708187A (en) * | 1996-06-27 | 1998-01-13 | Eli Lilly And Company | 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta 7,6-B!indoles: New 5-HT1F agonists |
| US5891885A (en) * | 1996-10-09 | 1999-04-06 | Algos Pharmaceutical Corporation | Method for treating migraine |
| GB9723061D0 (en) * | 1997-10-31 | 1998-01-07 | Vanguard Medica Ltd | Medicaments |
| US6066092A (en) * | 1997-11-06 | 2000-05-23 | Cady; Roger K. | Preemptive prophylaxis of migraine device and method |
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| GB9808069D0 (en) * | 1998-04-16 | 1998-06-17 | Vanguard Medica Ltd | Novel processes |
| GB9817911D0 (en) * | 1998-08-17 | 1998-10-14 | Vanguard Medica Ltd | New use |
| US20030198669A1 (en) * | 2001-07-05 | 2003-10-23 | R.T. Alamo Ventures I, Llc | Compositions and methods for rapid dissolving formulations of dihydroergotamine and caffeine for the treatment of migraine |
| US6685951B2 (en) | 2001-07-05 | 2004-02-03 | R. T. Alamo Ventures I, Inc. | Administration of dihydroergotamine as a sublingual spray or aerosol for the treatment of migraine |
| US20030017175A1 (en) * | 2001-07-05 | 2003-01-23 | R.T. Alamo Ventures I, Inc. | Sublingual administration of dihydroergotamine for the treatment of migraine |
| WO2003029214A1 (en) * | 2001-09-28 | 2003-04-10 | F. Hoffmann-La Roche Ag | Pseudopolymorphic forms of carvedilol |
| BR0312176A (pt) | 2002-06-21 | 2005-04-05 | Suven Life Sciences Ltd | Composto, composição farmaceutica, uso de um composto, método para o tratamento, método para reduzir a morbidez e a mortalidade associadas com o excesso de peso, processo para a preparação de um composto, novo intermediario e processo para a preparação de um novo intermediario |
| AU2003249584B9 (en) | 2002-06-21 | 2008-05-15 | Suven Life Sciences Limited | Arylalkyl indoles having sertonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them |
| BRPI0315959C1 (pt) | 2002-11-28 | 2021-05-25 | Suven Life Sciences Ltd | composto, composição farmacêutica, uso do composto, método para o tratamento, método para reduzir a morbidez e a mortalidade associadas com o excesso de peso e processo para a preparação do composto |
| PT1567492E (pt) | 2002-11-28 | 2013-07-22 | Suven Life Sciences Ltd | N-arilsulfonil-3-aminoalcoxi-indóis |
| DK1581538T3 (da) | 2002-12-18 | 2007-06-25 | Suven Life Sciences Ltd | Tetracykliske 3-substituerede indoler med serotoninreceptoraffinitet |
| RU2430088C2 (ru) * | 2004-07-14 | 2011-09-27 | Центарис Гмбх | Производные тетрагидрокарбазола и фармацевтическая композиция на их основе |
| US7601856B2 (en) | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| BRPI0715179A2 (pt) * | 2006-08-07 | 2013-06-11 | Actelion Pharmaceuticals Ltd | composto, composiÇço farmacÊutica e uso de um composto |
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| US3642816A (en) * | 1967-08-10 | 1972-02-15 | Sterling Drug Inc | 3-acetamido-1 2 3 4-tetrahydrocarbazole |
| US3959309A (en) | 1968-01-24 | 1976-05-25 | Sterling Drug Inc. | 3-Amido-1,2,3,4-tetrahydrocarbazoles |
| US4062864A (en) * | 1968-01-24 | 1977-12-13 | Sterling Drug Inc. | 3-Hydroxy carbazole derivatives |
| US3592824A (en) * | 1970-03-12 | 1971-07-13 | Miles Lab | 3-substituted amino-1,2,3,4-tetrahydrocarbazoles |
| BE787537A (fr) * | 1971-08-16 | 1973-02-14 | Sterling Drug Inc | Tetrahydrocarbazoles |
| US4172834A (en) * | 1971-08-16 | 1979-10-30 | Sterling Drug Inc. | 3-Amino-tetrahydrocarbazoles |
| DE2815926A1 (de) * | 1978-04-13 | 1979-10-18 | Boehringer Mannheim Gmbh | Neue carbazolyl-(4)-oxy-propanolamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4257952A (en) * | 1977-06-06 | 1981-03-24 | Sterling Drug Inc. | 3-Amino-tetrahydrocarbazoles |
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| EP0115607A1 (de) * | 1983-01-04 | 1984-08-15 | MERCK PATENT GmbH | Tetrahydrocarbazolderivate |
-
1991
- 1991-06-26 GB GB919113802A patent/GB9113802D0/en active Pending
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1992
- 1992-06-17 EP EP92912379A patent/EP0591280B1/en not_active Expired - Lifetime
- 1992-06-17 CZ CZ961506A patent/CZ282327B6/cs not_active IP Right Cessation
- 1992-06-17 KR KR1019930704055A patent/KR100251571B1/ko not_active Expired - Lifetime
- 1992-06-17 UA UA93002251A patent/UA41254C2/uk unknown
- 1992-06-17 SK SK1054-98A patent/SK280906B6/sk not_active IP Right Cessation
- 1992-06-17 US US08/167,846 patent/US5464864A/en not_active Expired - Lifetime
- 1992-06-17 DE DE69226953T patent/DE69226953T2/de not_active Expired - Lifetime
- 1992-06-17 JP JP51108692A patent/JP3261502B2/ja not_active Expired - Lifetime
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- 1992-06-17 PL PL92301883A patent/PL169392B1/pl unknown
- 1992-06-17 SK SK1685-98A patent/SK280907B6/sk not_active IP Right Cessation
- 1992-06-17 DE DE2002199042 patent/DE10299042I2/de active Active
- 1992-06-17 DK DK92912379T patent/DK0591280T3/da active
- 1992-06-17 PL PL92311304A patent/PL171034B1/pl unknown
- 1992-06-17 HU HU9303731A patent/HU218907B/hu active IP Right Revival
- 1992-06-17 SG SG1996004938A patent/SG47877A1/en unknown
- 1992-06-17 BR BR9206237A patent/BR9206237A/pt not_active Application Discontinuation
- 1992-06-17 PL PL92307118A patent/PL169410B1/pl unknown
- 1992-06-17 RU RU93058534A patent/RU2137474C1/ru active Protection Beyond IP Right Term
- 1992-06-17 CA CA002113726A patent/CA2113726C/en not_active Expired - Lifetime
- 1992-06-17 AT AT92912379T patent/ATE170746T1/de active
- 1992-06-17 WO PCT/GB1992/001082 patent/WO1993000086A1/en not_active Ceased
- 1992-06-17 CZ CZ961505A patent/CZ150596A3/cs not_active IP Right Cessation
- 1992-06-17 SK SK1319-93A patent/SK280905B6/sk not_active IP Right Cessation
- 1992-06-24 PT PT100620A patent/PT100620B/pt not_active IP Right Cessation
- 1992-06-24 MA MA22853A patent/MA22563A1/fr unknown
- 1992-06-24 ZA ZA924658A patent/ZA924658B/xx unknown
- 1992-06-24 NZ NZ243288A patent/NZ243288A/en not_active IP Right Cessation
- 1992-06-25 IL IL117105A patent/IL117105A/en not_active IP Right Cessation
- 1992-06-25 CN CN92108831A patent/CN1034072C/zh not_active Expired - Lifetime
- 1992-06-25 AP APAP/P/1992/000403A patent/AP344A/en active
- 1992-06-25 IL IL11710596A patent/IL117105A0/xx unknown
- 1992-06-25 IL IL117104A patent/IL117104A/xx not_active IP Right Cessation
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- 1992-06-25 TW TW081104991A patent/TW214544B/zh not_active IP Right Cessation
- 1992-06-26 MX MX9203444A patent/MX9203444A/es unknown
- 1992-06-26 SI SI9200125A patent/SI9200125B/sl unknown
- 1992-07-01 IE IE206292A patent/IE922062A1/en not_active IP Right Cessation
- 1992-10-04 SA SA92130141A patent/SA92130141B1/ar unknown
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1993
- 1993-12-23 NO NO934759A patent/NO304774B1/no not_active IP Right Cessation
- 1993-12-23 FI FI935842A patent/FI103967B1/fi not_active IP Right Cessation
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1995
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1997
- 1997-05-06 BR BR1100460-6A patent/BR1100460A/pt active IP Right Grant
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2002
- 2002-07-24 LU LU90939C patent/LU90939I2/fr unknown
- 2002-10-14 NL NL300103C patent/NL300103I2/nl unknown
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2005
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