FI112487B - Imidazobenso- och -tieno[1,4]diazepiner - Google Patents
Imidazobenso- och -tieno[1,4]diazepiner Download PDFInfo
- Publication number
- FI112487B FI112487B FI951251A FI951251A FI112487B FI 112487 B FI112487 B FI 112487B FI 951251 A FI951251 A FI 951251A FI 951251 A FI951251 A FI 951251A FI 112487 B FI112487 B FI 112487B
- Authority
- FI
- Finland
- Prior art keywords
- imidazo
- dihydro
- mmol
- oxadiazol
- methyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Plant Substances (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Claims (8)
1. Imidazobenso- och -tieno[1,4]diazepiner, kännetecknade därav, att de har den allmänna 5 formeln N R1 ®t>3 10 Γ '4 o R väri A tillsammans med de bada med a och β betecknade kolatomerna betecknar en av resterna 5Οί Oi h öj p6 ^ , b och R5 20 (A1) (A2) (A3) , Q betecknar en av resterna Π -ζ^.-ΓΛ -ti- - " och :**· 25 : (q1) (Q2) (Q3) tl# * * * · 1 2 : : : R och R betecknar vardera väte, lägre alkyl, lägre alkenyl, lägre alkinyl, lägre hydroxialkyl, lägre alkoxi-(lägre alkyl), (C3_C6)-cykloalkyl, (C3-C6) -cyklo-,··· 30 alkyl-(lägre alkyl), amino-(lägre alkyl), lägre al- ‘2 kylamino(lägre alkyl), di-(lägre alkyl)amino-(lägre alkyl) ί ’·· eller fenyl-(lägre alkyl) som eventuellt är substituerad :>t,· med halogen, t rif luormetyl, lägre alkyl eller lägre alkoxi, eller R1 och R2 betecknar tillsammans med kvävea-35 tomen 1-pyrrolidinyl, 1-pyrrolinyl, piperidino, 2,6-di-metylpiperidino, 3,3-dimetylpiperidino, hexametylen-imin- 219 11 k. <;: :- 1-yl, heptametylen imin-l-yl, morfolino, 4-metyl-l- piperazinyl eller isoindolin-2-yl; R3 betecknar väte och R4 betecknar lägre alkyl eller R3 och R4 betecknar tillsaramans en di- eller 5 trimetylengrupp; och R5 och R6 betecknar vardera väte, halogen, trifluormetyl, lägre alkoxi eller nitro; varvid den med γ betecknade kolatomen uppvisar S-konfiguration, när R3 har annan betydelse än väte, 10 och farmaceutiskt godtagbara syraadditionssalter av dessa föreningar.
2. Föreningar enligt patentkrav 1, k ä n n e -tecknade därav, att Q betecknar resten Q2 eller resten Q3; R1 och R2 vardera betecknar lägre alkyl, lägre 15 hydroxialkyl eller (C3-C6)-cykloalkyl-(lägre alkyl) eller tillsammans med kväveatomen piperidino eller isoindolin-2-yl; eller A betecknar resten A1 eller resten A2; R5 betecknar väte, klor, fluor, trifluormetyl eller lägre alkoxi och R6 betecknar väte eller fluor. 20 3. Föreningar enligt patentkrav 1 eller 2, kännetecknade därav, att R3 betecknar väte och R4 betecknar metyl eller R3 och R4 tillsammans betecknar dimetylen. 4 . 3-(5-dipropylaminometyl-l, 2,4-oxadiazol-3-yl) -8- 25 fluor-5-metyl-5,6-dihydro-4H-imidazo[1, 5-a]-[1,4]-bensodia-zepin-6-on. 5. (S)-8-klor-l-(5-dipropylaminometyl-l,2,4-oxadia- zol-3-yl)-12,12a-dihydro-9H,HH-azeto[2,1-c]-imidazo-[1,5— ,, , a] [ 1, 4 ] bensodiazepin-9-on. ; 30 6. (S)-1-(5-dipropylaminometyl-l,2,4-oxadiazol-3- 'y ' yl)-11,lla-dihydro-8H,10H-azeto[1,2-a]imidazo-[5,1-c]tieno- [3,2-e] [1,4] diazepin-8-on. 7. 8-fluor-5-metyl-3-[5-(piperidin-1-ylmetyl)- 1,2,4-oxadiazol-3-yl]-5,6-dihydro-4H-imidazo-[1,5-a][1,4]-35 bensodiazepin-6-on. 11.. 220 8 . (S)-1-(5-diallylaminometyl)-1,2,4-oxadiazol-3- yl)-8-klor-7-fluor-12,12a-dihydro-9H,HH-azeto[2,1-c]imi-dazo[l,5-a][1,4]bensodiazepin-9-on. 9. 3-(5-dipropylaminometyl-l, 2,4-oxadiazol-3-yl)-5- 5 metyl-5,6-dihydro-4H-imidazo[1,5-a][1,4]bensodiazepin-6-on. 10 . 3- (5-dipropylaminometyl-l,3,4-oxadiazol-2-yl)- 8-fluor-5-metyl-5,6-dihydro-4H-imidazo[1,5-c]-[1,4]benso-diazepin-6-on. 11. 3-(5-dietylaminometyl-l,2,4-oxadiazol-3-yl)-8- 10 fluor-5-metyl-5,6-dihydro-4H-imidazo[1,5-a]-[1,4]benso-diazepin-6-on. 12 . (S)-8-klor-l-[5-(piperidin-1-yl)metyl-1,2,4- oxadiazol-3-yl]-12,12a-dihydro-9H,HH-azeto[2,1-c]imidazo-[1,5-a] [ 1,4]bensodiazepin-9-on. 15 13. 7-fluor-5-metyl-3-(5-dipropylaminometyl-l,2,4- oxadiazol-3-yl)-5,6-dihydro-4H-imidazo[l,5-a]-[l,4]benso-diazepin-6-on. 14 . 7-klor-3-(5-dietylaminometyl-l,2,4-oxadiazol-3- yl)-5-metyl-5,6-dihydro-4H-imidazo[l,5-a]-[l,4]bensodia- 20 zepin-6-on. 15 . 7-klor-3-(5-dipropylaminometyl-l,3,4-oxadiazol- 2-yl)-5-metyl-5,6-dihydro-4H-imidazo[l,5-a]-[l,4]bensodia-zepin-6-on. 16. (S)-1- (5-dietylaminometyl-l,2,4-oxadiazol-3- 25 yl)-11,lla-dihydro-8H,10H-azeto[1,2-a]imidazo[5,1-c]tieno-: : [3,2-e] [ 1,4]diazepin-8-on. ; 17. (S)-1-(5-dibutylaminometyl-l, 3,4-oxadiazol-2- yl)-11,lla-dihydro-8H,10H-azeto[1,2-a]imidazo-[5, 1-c]tieno-:>_ [ 3,2-e] [ 1,4 ] diazepin-8-on. M. 30 18. 3- (5-di-isopropylaminometyl-1,2,4-oxadiazol-3- yl) -5-metyl-5,6-dihydro-4H-imidazo [ 1,5-a] [ 1,4 ] bensodia-* '·. zepin-6-on. ; ; 19. 3-(5-diisopropylaminometyl-l,2,4-oxadiazol-3- yl)-8-fluor-5-metyl-5, 6-dihydro-4H-imidazo [1,5-a] [1,4]-35 bensodiazepin-6-on. 221 11 ϊ ;: ; 20 . (S)-1-(5-diallylaminometyl-l,2,4-oxadiazol-3- yl)-8-klor-12,12a-dihydro-9H,HH-azeto[2,1-c]-imidazo[1,5-a][1,4]bensodiazepin-9-on; (S)-1-(5-diallylaminometyl-l,2,4-oxadiazol-3-yl)-8-5 trifluormetyl-12,12a-dihydro-9H,llH-azeto[2,1-c]imidazo-[1,5-a][1,4]bensodiazepin-9-on; 3-(5-diallylaminometyl-l,2,4-oxadiazol-3-yl)-8-fluor-5-metyl-5,6-dihydro-4H-imidazo[l,5-a]-[l,4]benso-diazepin-6-on; 10 8-fluor-3-(5-isoindolin-2-ylmetyl-l,2,4-oxadiazol- 3-yl)-5-metyl-5,6-dihydro-4H-imidazo[1,5-a]-[1,4]bensodia-zepin-6-on; och (S)-1-(5-diallylaminometyl-l,2,4-oxadiazol-3-yl) -11,1la-dihydro-8H,10H-azeto[l,2-a]imidazo[5,1-c]-tieno[3,2-15 e][1,4]diazepin-8-on. 21. 3- (5-dipropylaminometyl-l,2,4-oxadiazol-3-yl) - 5-metyl-5,6-dihydro-4H-imidazo[1,5-a]tieno-[2,3-f] [1,4]-diazepin-6-on; 3-(5-dipropylaminometyl-l,2,4-oxadiazol-3-yl)-5-20 metyl-7-trifluormetyl-5,6-dihydro-4H-imidazo[1,5-a] [1,4]-bensodiazepin-6-on; och (S)-8-klor-l-(5-dipropylaminometyl-l,3,4-oxadiazol-2-yl)-12,12a-dihydro-9H,llH-azeto[2,1-c]imidazo[1,5-a] [ 1,4]bensodiazepin-9-on. ! 25 22. Läkemedel, särskilt anxiolytiska och/eller an- ; tikonvulsiva och/eller muskelrelaxerande och/eller sedativ- hypnotiska medel, kännetecknat därav, att det innehäller en förening enligt nägot av patentkraven 1-21 , och en terapeutiskt inert bärare. *,.] 30 23. Användning av föreningar enligt nägot av *·;·’ patentkraven 1-21 som terapeutiskt aktiva substanser, särskilt som anxiolytisk och/eller antikonvulsiv och/eller muskelrelaxerande och/eller sedativ-hypnotisk aktiva substanser. 35 222 11 p:,:
24. Användning av föreningar enligt nägot av patentkraven 1-21 för framsställning av anxiolytiska och/eller antikonvulsiva och/eller muskelrelaxerande och/eller sedativa-hypnotiska läkemedel.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH78394 | 1994-03-16 | ||
| CH78394 | 1994-03-16 | ||
| CH1095 | 1995-01-03 | ||
| CH1095 | 1995-01-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI951251A0 FI951251A0 (sv) | 1995-03-16 |
| FI951251A FI951251A (sv) | 1995-09-17 |
| FI112487B true FI112487B (sv) | 2003-12-15 |
Family
ID=25683249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI951251A FI112487B (sv) | 1994-03-16 | 1995-03-16 | Imidazobenso- och -tieno[1,4]diazepiner |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5665718A (sv) |
| EP (1) | EP0672666B1 (sv) |
| JP (1) | JP2690282B2 (sv) |
| KR (1) | KR100214800B1 (sv) |
| CN (1) | CN1036995C (sv) |
| AT (1) | ATE203536T1 (sv) |
| AU (1) | AU679608B2 (sv) |
| BG (1) | BG62210B1 (sv) |
| CA (1) | CA2143246C (sv) |
| CZ (1) | CZ288594B6 (sv) |
| DE (1) | DE59509432D1 (sv) |
| DK (1) | DK0672666T3 (sv) |
| ES (1) | ES2160646T3 (sv) |
| FI (1) | FI112487B (sv) |
| GR (1) | GR3037019T3 (sv) |
| HU (1) | HU219987B (sv) |
| IL (1) | IL112955A (sv) |
| IS (1) | IS4273A (sv) |
| LV (1) | LV11327B (sv) |
| MA (1) | MA23479A1 (sv) |
| NO (1) | NO303731B1 (sv) |
| NZ (1) | NZ270685A (sv) |
| PH (1) | PH31443A (sv) |
| PT (1) | PT672666E (sv) |
| RO (1) | RO117698B1 (sv) |
| RU (1) | RU2139873C1 (sv) |
| SK (1) | SK33995A3 (sv) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW349100B (en) * | 1994-11-11 | 1999-01-01 | Hoffmann La Roche | Oxazolyl- and thiazolylimidazo-benzo- and thienodiazepines |
| US5905176A (en) * | 1998-08-28 | 1999-05-18 | Eastman Chemical Company | Process for the production of cyclobutyl halides |
| EP1178990B1 (en) * | 1999-05-12 | 2003-01-29 | F. Hoffmann-La Roche Ag | Imidazodiazepine derivative |
| US7160880B1 (en) * | 1999-05-14 | 2007-01-09 | Cenes Limited | Short-acting benzodiazepines |
| US20060065608A1 (en) * | 2004-09-29 | 2006-03-30 | Choate Chris E | Process and apparatus for generating useful biomass from organic waste streams |
| WO2006078577A1 (en) * | 2005-01-19 | 2006-07-27 | Merck & Co., Inc. | Tertiary carbinamines having substituted heterocycles, which are active as inhibitors of beta-secretase, for the treatment of alzheimer's disease |
| US7820674B2 (en) * | 2005-01-19 | 2010-10-26 | Merck, Sharp & Dohme Corp. | Aminomethyl beta-secretase inhibitors for the treatment of alzheimer's disease |
| CA2607226A1 (en) * | 2005-05-16 | 2007-02-15 | Wisys Technology Foundation, Inc. | Gabaergic agents to treat memory deficits |
| GB0613693D0 (en) * | 2006-07-10 | 2006-08-16 | Cenes Ltd | Benzodiazepine salts (3) |
| US9193730B2 (en) | 2006-07-10 | 2015-11-24 | Paion Uk Limited | Short-acting benzodiazepine salts and their polymorphic forms |
| WO2009024324A2 (en) * | 2007-08-20 | 2009-02-26 | Evotec Neurosciences Gmbh | Treatment of sleep disorders |
| EP2190435B1 (en) * | 2007-08-20 | 2018-05-30 | Evotec International GmbH | Treatment of sleep disorders |
| US20090054412A1 (en) * | 2007-08-20 | 2009-02-26 | John Alan Kemp | Treatment of Sleep Disorders |
| RU2503681C2 (ru) * | 2008-09-30 | 2014-01-10 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Новое конденсированное производное аминодигидротиазина |
| EP2450039A1 (en) | 2010-11-08 | 2012-05-09 | PAION UK Ltd. | Dosing regimen for sedation with CNS 7056 (Remimazolam) |
| CA2874247C (en) | 2012-05-22 | 2020-07-28 | Paion Uk Limited | Compositions comprising short-acting benzodiazepines |
| AR094963A1 (es) | 2013-03-04 | 2015-09-09 | Ono Pharmaceutical Co | Reacción de oxidación excelente en el índice de conversión |
| SG11201601682RA (en) | 2013-09-06 | 2016-04-28 | Aurigene Discovery Tech Ltd | 1,2,4-oxadiazole derivatives as immunomodulators |
| CN114213356A (zh) | 2015-03-10 | 2022-03-22 | 奥瑞基尼探索技术有限公司 | 作为免疫调节剂的1,2,4-噁二唑和噻二唑化合物 |
| CN107427476A (zh) * | 2015-03-10 | 2017-12-01 | 奥瑞基尼探索技术有限公司 | 作为免疫调节剂的3‑取代的‑1,2,4‑噁二唑和噻二唑化合物 |
| CN109641000A (zh) | 2016-04-14 | 2019-04-16 | Paion英国有限公司 | 经口吸入和经鼻用的苯并二氮杂*类 |
| WO2019061324A1 (en) | 2017-09-29 | 2019-04-04 | Curis Inc. | CRYSTALLINE FORMS OF IMMUNOMODULATORS |
| JP2020536872A (ja) | 2017-10-11 | 2020-12-17 | オーリジーン ディスカバリー テクノロジーズ リミテッドＡｕｒｉｇｅｎｅ Ｄｉｓｃｏｖｅｒｙ Ｔｅｃｈｎｏｌｏｇｉｅｓ Ｌｉｍｉｔｅｄ | ３−置換１，２，４−オキサジアゾールの結晶形態 |
| EA202090746A1 (ru) | 2017-11-03 | 2020-08-17 | Ориджен Дискавери Текнолоджис Лимитед | Двойные ингибиторы путей tim-3 и pd-1 |
| AU2018360389A1 (en) | 2017-11-06 | 2020-05-07 | Aurigene Oncology Limited | Conjoint therapies for immunomodulation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK151808C (da) * | 1982-11-16 | 1988-06-20 | Ferrosan As | Analogifremgangsmaade til fremstilling af oxadiazolylimidazo-oe1,4aa-benzodiazepinderivater |
| ZW985A1 (en) * | 1984-01-19 | 1985-08-28 | Hoffmann La Roche | Imidazodiazepine derivatives |
| AU587802B2 (en) * | 1985-03-08 | 1989-08-31 | Ferrosan A/S | Novel oxadiazolyl imidazobenzodiazepine derivatives and methods of preparing such compounds |
| US4622320A (en) * | 1985-05-17 | 1986-11-11 | As Ferrosan | Oxadiazolylimidazobenzodiazepine, compositions, and method |
| DK476885D0 (da) * | 1985-10-17 | 1985-10-17 | Ferrosan As | Heterocycliske forbindelser og fremgangsmaader til fremstilling heraf |
| DK174086D0 (da) * | 1986-04-16 | 1986-04-16 | Ferrosan As | Nye benzodiazepinderivater samt fremgangsmaade til fremstilling af samme |
| US4939139A (en) * | 1989-07-26 | 1990-07-03 | Merck & Co., Inc. | 7-chloro-5,6-dihydro-3-(5-(1,2-dihydroxy-isopropyl)-1,2,4-oxadiazol-3-yl)-5-methyl-6-oxo-4H-imidazo[1,5A][1,4]benzodiazepine |
| US4904654A (en) * | 1989-07-26 | 1990-02-27 | Merck & Co., Inc. | 7-chloro-5,6-dihydro-3-(5-(2-hydroxy-isopropyl)-1,2,4-oxadiazol-3-yl)-5-methyl-6-oxo-4H-imidazo[1,5a][1,4]benzodiazepine |
-
1995
- 1995-02-23 CA CA002143246A patent/CA2143246C/en not_active Expired - Lifetime
- 1995-03-03 DE DE59509432T patent/DE59509432D1/de not_active Expired - Lifetime
- 1995-03-03 ES ES95103028T patent/ES2160646T3/es not_active Expired - Lifetime
- 1995-03-03 EP EP95103028A patent/EP0672666B1/de not_active Expired - Lifetime
- 1995-03-03 AT AT95103028T patent/ATE203536T1/de active
- 1995-03-03 PT PT95103028T patent/PT672666E/pt unknown
- 1995-03-03 DK DK95103028T patent/DK0672666T3/da active
- 1995-03-10 AU AU14760/95A patent/AU679608B2/en not_active Expired
- 1995-03-10 NZ NZ270685A patent/NZ270685A/en not_active IP Right Cessation
- 1995-03-10 PH PH50110A patent/PH31443A/en unknown
- 1995-03-10 IL IL112955A patent/IL112955A/en not_active IP Right Cessation
- 1995-03-13 HU HU9500743A patent/HU219987B/hu not_active IP Right Cessation
- 1995-03-14 RU RU95103921A patent/RU2139873C1/ru active
- 1995-03-15 SK SK339-95A patent/SK33995A3/sk unknown
- 1995-03-15 RO RO95-00534A patent/RO117698B1/ro unknown
- 1995-03-15 CZ CZ1995663A patent/CZ288594B6/cs not_active IP Right Cessation
- 1995-03-15 LV LVP-95-59A patent/LV11327B/lv unknown
- 1995-03-15 CN CN95102481A patent/CN1036995C/zh not_active Expired - Lifetime
- 1995-03-15 NO NO950999A patent/NO303731B1/no not_active IP Right Cessation
- 1995-03-15 MA MA23807A patent/MA23479A1/fr unknown
- 1995-03-15 IS IS4273A patent/IS4273A/is unknown
- 1995-03-16 FI FI951251A patent/FI112487B/sv not_active IP Right Cessation
- 1995-03-16 JP JP7057227A patent/JP2690282B2/ja not_active Expired - Lifetime
- 1995-03-16 BG BG99505A patent/BG62210B1/bg unknown
- 1995-03-16 KR KR1019950005414A patent/KR100214800B1/ko not_active IP Right Cessation
-
1996
- 1996-01-16 US US08/586,439 patent/US5665718A/en not_active Expired - Lifetime
-
2001
- 2001-10-25 GR GR20010401890T patent/GR3037019T3/el unknown
Also Published As
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| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |