PE25498A1 - Compuestos de 1-fenil-2-dimetilaminometil-ciclohexan-1-ol, procedimientos para su preparacion y la aplicacion de estos compuestos en medicamentos - Google Patents
Compuestos de 1-fenil-2-dimetilaminometil-ciclohexan-1-ol, procedimientos para su preparacion y la aplicacion de estos compuestos en medicamentosInfo
- Publication number
- PE25498A1 PE25498A1 PE1996000875A PE00087596A PE25498A1 PE 25498 A1 PE25498 A1 PE 25498A1 PE 1996000875 A PE1996000875 A PE 1996000875A PE 00087596 A PE00087596 A PE 00087596A PE 25498 A1 PE25498 A1 PE 25498A1
- Authority
- PE
- Peru
- Prior art keywords
- compounds
- formula
- phenyl
- dimethylaminomethyl
- reacted
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
SE REFIEREN A COMPUESTOS DE FORMULA (I), EN DONDE PREFERIBLEMENTE LA CONFIGURACION ENTRE EL CICLO FENILICO Y EL GRUPO DIMETILAMINOMETILO SE ENCUENTRA EN POSICION TRANS; -Y=Z ES (a) -CH2-CH, (b) -CH=, o (c) -O-CH; "X" ES O o S; R1 ES H, ALQUILO C1-C6 O CICLOALQUILO C5-C7, ENTRE OTROS; R2 ES CICLOPENTILMETILO, FENILO U BENCILO OPCIONALMENTE SUSTITUIDOS, ENTRE OTROS. TAMBIEN SE REFIERE AL PROCEDIMIENTO DE PREPARACION DE (I), QUE COMPRENDE: 1) HACER REACCIONAR LA CETONA DE FORMULA (XV) EN DONDE: "A" ES CnH2n; n ES 2; 3; 4; 5 o 6 CON CLORURO DE DIMETILAMONIOMETILENO; 2) HACER REACCIONAR LA �-DIMETILAMINO CETONA OBTENIDA EN (1) CON UN COMPUESTO ORGANOMETALICO; 3) DESACETILACION POR CATALISIS PROTONICA; 4) REDUCCION HASTA UN 4-HIDROXI-DERIVADO; SI -Y=Z ES (c), ENTONCES: 5) LO OBTENIDO EN (3) SE HACE REACCIONAR CON R2-G, EN DONDE: "G" ES Cl, Br, I o TOLUENO SULFONILOXI; SI -Y=Z ES (b), ENTONCES: 6) LO OBTENIDO EN (3) SE HACE REACCIONAR CON UN COMPUESTO DE FORMULA (XX) EN DONDE: n ES 1; 2 o 3; SI -Y=Z ES (a), ENTONCES: 7) HIDROGENAR LO OBTENIDO EN (6). LOS COMPUESTOS OBTENIDOS SON ANALGESICOS NO OPIOIDES, UTILIZABLES INCLUSO EN ESTADOS DOLOROSOS EXTREMADAMENTE INTENSOS PARA LOS CUALES YA NO ES SUFICIENTE UN EFECTO OPIOIDE DE EFICACIA MEDIA
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19547766A DE19547766A1 (de) | 1995-12-20 | 1995-12-20 | 1-Phenyl-2-dimethylaminomethyl-cyclohexan-1-ol-verbindungen als pharmazeutische Wirkstoffe |
Publications (1)
Publication Number | Publication Date |
---|---|
PE25498A1 true PE25498A1 (es) | 1998-05-23 |
Family
ID=7780779
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PE1996000875A PE25498A1 (es) | 1995-12-20 | 1996-12-05 | Compuestos de 1-fenil-2-dimetilaminometil-ciclohexan-1-ol, procedimientos para su preparacion y la aplicacion de estos compuestos en medicamentos |
Country Status (23)
Country | Link |
---|---|
US (1) | US5801201A (es) |
EP (1) | EP0780369B1 (es) |
JP (1) | JP3987598B2 (es) |
KR (1) | KR100439283B1 (es) |
CN (1) | CN1071309C (es) |
AR (1) | AR004357A1 (es) |
AT (1) | ATE188961T1 (es) |
AU (1) | AU705970B2 (es) |
CA (1) | CA2193337C (es) |
CO (1) | CO4480100A1 (es) |
DE (2) | DE19547766A1 (es) |
DK (1) | DK0780369T3 (es) |
ES (1) | ES2144192T3 (es) |
GR (1) | GR3032486T3 (es) |
HK (1) | HK1001860A1 (es) |
HU (1) | HU223340B1 (es) |
IL (1) | IL119864A (es) |
PE (1) | PE25498A1 (es) |
PL (1) | PL185813B1 (es) |
PT (1) | PT780369E (es) |
RU (1) | RU2167148C2 (es) |
SI (1) | SI0780369T1 (es) |
ZA (1) | ZA9610650B (es) |
Families Citing this family (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19830105C1 (de) * | 1998-07-06 | 2000-02-17 | Gruenenthal Gmbh | Acridinderivate |
DE10000311A1 (de) * | 2000-01-05 | 2001-07-12 | Gruenenthal Gmbh | Aminomethyl-Phonyl-Cyclohexanonderivate |
DE10000312A1 (de) * | 2000-01-05 | 2001-07-12 | Gruenenthal Gmbh | Substituierte Aminomethyl-Phenyl-Cyclohexanderivate |
DE10004926A1 (de) * | 2000-02-04 | 2001-08-09 | Gruenenthal Gmbh | Verfahren zur enzymatischen Racematspaltung von Aminomethyl-Aryl-Cyclohexanol-Derivaten |
DE10049483A1 (de) | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte 1-Aminobutan-3-ol-Derivate |
DE10049481A1 (de) * | 2000-09-29 | 2002-05-02 | Gruenenthal Gmbh | Substituierte C-Cyclohexylmethylamin-Derivate |
US20050176790A1 (en) | 2001-02-28 | 2005-08-11 | Johannes Bartholomaus | Pharmaceutical salts |
US6974839B2 (en) | 2001-03-16 | 2005-12-13 | Dmi Biosciences, Inc. | Method of delaying ejaculation |
US6649783B2 (en) * | 2001-10-03 | 2003-11-18 | Euro-Celtique, S.A. | Synthesis of (+/-)-2-((dimethylamino)methyl)-1-(aryl)cyclohexanols |
DE10161818A1 (de) | 2001-12-14 | 2003-06-26 | Gruenenthal Gmbh | Substituierte 1,5-Diaminopentan-3-ol-Verbindungen |
DE10164581A1 (de) * | 2001-12-14 | 2003-06-26 | Gruenenthal Gmbh | Substituierte Aminoalkohole |
DE10206405A1 (de) * | 2002-02-14 | 2003-08-28 | Gruenenthal Gmbh | Synthese von substituierten Carbamidestern |
DE10206403A1 (de) * | 2002-02-14 | 2003-08-28 | Gruenenthal Gmbh | Synthese von Beta-Aminoketonen |
DE10213051B4 (de) * | 2002-03-23 | 2013-03-07 | Grünenthal GmbH | Substituierte 4-Aminocyclohexanole |
US7776314B2 (en) | 2002-06-17 | 2010-08-17 | Grunenthal Gmbh | Abuse-proofed dosage system |
DE102005005446A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Bruchfeste Darreichungsformen mit retardierter Freisetzung |
DE10361596A1 (de) | 2003-12-24 | 2005-09-29 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
DE10336400A1 (de) | 2003-08-06 | 2005-03-24 | Grünenthal GmbH | Gegen Missbrauch gesicherte Darreichungsform |
US20070048228A1 (en) | 2003-08-06 | 2007-03-01 | Elisabeth Arkenau-Maric | Abuse-proofed dosage form |
US8075872B2 (en) | 2003-08-06 | 2011-12-13 | Gruenenthal Gmbh | Abuse-proofed dosage form |
DE102004032051A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten, festen Darreichungsform |
DE102004019916A1 (de) * | 2004-04-21 | 2005-11-17 | Grünenthal GmbH | Gegen Missbrauch gesichertes wirkstoffhaltiges Pflaster |
DE102004032049A1 (de) | 2004-07-01 | 2006-01-19 | Grünenthal GmbH | Gegen Missbrauch gesicherte, orale Darreichungsform |
DE102005005449A1 (de) | 2005-02-04 | 2006-08-10 | Grünenthal GmbH | Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform |
DE102005033732B4 (de) * | 2005-05-27 | 2014-02-13 | Grünenthal GmbH | Trennung stereoisomerer N,N-Dialkylamino-2-alkyl-3-hydroxy-3-phenyl-alkane |
DE202005014347U1 (de) | 2005-09-09 | 2007-01-18 | Grünenthal GmbH | Applikationssystem für ein wirkstoffhaltiges Pflaster und Wirkstoffabgaberegulierungsmittel |
SA07280459B1 (ar) | 2006-08-25 | 2011-07-20 | بيورديو فارما إل. بي. | أشكال جرعة صيدلانية للتناول عن طريق الفم مقاومة للعبث تشتمل على مسكن شبه أفيوني |
DE102007011485A1 (de) | 2007-03-07 | 2008-09-11 | Grünenthal GmbH | Darreichungsform mit erschwertem Missbrauch |
MY153910A (en) * | 2007-09-28 | 2015-04-15 | Daiichi Sankyo Co Ltd | BICYCLIC y-AMINO ACID DERIVATIVE |
BRPI0906467C1 (pt) | 2008-01-25 | 2021-05-25 | Gruenenthal Gmbh | forma de dosagem farmacêutica com formato exterior modificado resistente à ruptura e com liberação controlada |
ES2366604T3 (es) * | 2008-02-29 | 2011-10-21 | Grünenthal GmbH | Procedimiento para preparar 6-dimetilaminometil-fenil-ciclohexano-1,3-dioles. |
CN102026959A (zh) * | 2008-02-29 | 2011-04-20 | 格吕伦塔尔有限公司 | 制造(1rs,3rs,6rs)-6-二甲基氨基甲基-1-(3-甲氧基苯基)-环己烷-1,3-二醇的方法 |
LT2273983T (lt) | 2008-05-09 | 2016-10-25 | Grünenthal GmbH | Tarpinės miltelių kompozicijos gamybos būdas ir galutinė kieta dozavimo forma naudojant purškalo kietinimo stadija |
EP2456427B1 (en) | 2009-07-22 | 2015-03-04 | Grünenthal GmbH | Hot-melt extruded controlled release dosage form |
AU2010275754B2 (en) | 2009-07-22 | 2014-05-15 | Grünenthal GmbH | Tamper-resistant dosage form for oxidation-sensitive opioids |
WO2011095314A2 (en) | 2010-02-03 | 2011-08-11 | Grünenthal GmbH | Preparation of a powdery pharmaceutical composition by means of an extruder |
MX2013002293A (es) | 2010-09-02 | 2013-05-09 | Gruenenthal Gmbh | Forma de dosificacion resistente a alteracion que comprende un polimero anionico. |
WO2012028319A1 (en) | 2010-09-02 | 2012-03-08 | Grünenthal GmbH | Tamper resistant dosage form comprising inorganic salt |
WO2012100423A1 (en) * | 2011-01-27 | 2012-08-02 | Eli Lilly And Company | Analgesic compounds, methods, and formulations |
LT2736497T (lt) | 2011-07-29 | 2017-11-10 | Grünenthal GmbH | Sugadinimui atspari tabletė, pasižyminti greitu vaisto atpalaidavimu |
BR112014002022A2 (pt) | 2011-07-29 | 2017-02-21 | Gruenenthal Gmbh | comprimido resistente à violação proporcionando liberação de fármaco imediata |
US20130225697A1 (en) | 2012-02-28 | 2013-08-29 | Grunenthal Gmbh | Tamper-resistant dosage form comprising pharmacologically active compound and anionic polymer |
AU2013248351B2 (en) | 2012-04-18 | 2018-04-26 | Grunenthal Gmbh | Tamper resistant and dose-dumping resistant pharmaceutical dosage form |
US10064945B2 (en) | 2012-05-11 | 2018-09-04 | Gruenenthal Gmbh | Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc |
JP6466417B2 (ja) | 2013-05-29 | 2019-02-06 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 二峰性放出プロファイルを有する改変防止(tamper−resistant)剤形 |
CA2907950A1 (en) | 2013-05-29 | 2014-12-04 | Grunenthal Gmbh | Tamper-resistant dosage form containing one or more particles |
EA032465B1 (ru) | 2013-07-12 | 2019-05-31 | Грюненталь Гмбх | Защищенная от применения не по назначению пероральная фармацевтическая лекарственная форма, содержащая этиленвинилацетатный полимер, и способ ее изготовления |
AU2014356581C1 (en) | 2013-11-26 | 2020-05-28 | Grunenthal Gmbh | Preparation of a powdery pharmaceutical composition by means of cryo-milling |
CN106572980A (zh) | 2014-05-12 | 2017-04-19 | 格吕伦塔尔有限公司 | 包含他喷他多的防篡改即释胶囊制剂 |
CN106456550A (zh) | 2014-05-26 | 2017-02-22 | 格吕伦塔尔有限公司 | 避免乙醇剂量倾泻的多颗粒 |
AU2016251854A1 (en) | 2015-04-24 | 2017-10-19 | Grunenthal Gmbh | Tamper-resistant dosage form with immediate release and resistance against solvent extraction |
JP2018526414A (ja) | 2015-09-10 | 2018-09-13 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 乱用抑止性の即放性製剤を用いた経口過剰摂取に対する保護 |
WO2019053494A1 (en) | 2017-09-18 | 2019-03-21 | R L Fine Chem Private Limited | PROCESS FOR THE PREPARATION OF O-DESMETHYLTRAMADOL AND SALTS THEREOF |
WO2021088758A1 (zh) * | 2019-11-06 | 2021-05-14 | 复旦大学 | 一类阿片受体激动剂及其制备方法和药物用途 |
CN112759587B (zh) * | 2019-11-06 | 2022-12-30 | 复旦大学 | 3-(二甲氨基甲基)哌啶-4-醇类衍生物及其制备方法和药物用途 |
CN112759544B (zh) * | 2019-11-06 | 2022-08-26 | 复旦大学 | 3-(二甲氨基甲基)哌啶-4-醇衍生物制备方法和药物用途 |
CN112759545B (zh) * | 2019-11-06 | 2022-12-13 | 复旦大学 | 3-(二甲氨基甲基)哌啶-4-醇类衍生物及其制备方法和药物用途 |
CN112759538B (zh) * | 2019-11-06 | 2022-01-18 | 复旦大学 | 3-(二甲氨基甲基)环己-4-醇衍生物及其制备方法和药物用途 |
CN112759546B (zh) * | 2019-11-06 | 2022-08-26 | 复旦大学 | 3-(二甲氨基甲基)哌啶-4-醇衍生物及其制备方法和药物用途 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE616646A (es) | ||||
DE1199764B (de) * | 1963-04-02 | 1965-09-02 | Gruenenthal Chemie | Verfahren zur Herstellung von basisch substituierten Phenolaethern |
US3652589A (en) * | 1967-07-27 | 1972-03-28 | Gruenenthal Chemie | 1-(m-substituted phenyl)-2-aminomethyl cyclohexanols |
JPS51143650A (en) * | 1975-06-06 | 1976-12-10 | Takeda Chem Ind Ltd | A process for preparing cyclohexanol derivatives |
-
1995
- 1995-12-20 DE DE19547766A patent/DE19547766A1/de not_active Withdrawn
-
1996
- 1996-12-02 AT AT96119283T patent/ATE188961T1/de active
- 1996-12-02 DE DE59604226T patent/DE59604226D1/de not_active Expired - Lifetime
- 1996-12-02 SI SI9630138T patent/SI0780369T1/xx unknown
- 1996-12-02 DK DK96119283T patent/DK0780369T3/da active
- 1996-12-02 AR ARP960105450A patent/AR004357A1/es unknown
- 1996-12-02 ES ES96119283T patent/ES2144192T3/es not_active Expired - Lifetime
- 1996-12-02 PT PT96119283T patent/PT780369E/pt unknown
- 1996-12-02 EP EP96119283A patent/EP0780369B1/de not_active Expired - Lifetime
- 1996-12-05 PE PE1996000875A patent/PE25498A1/es not_active Application Discontinuation
- 1996-12-18 ZA ZA9610650A patent/ZA9610650B/xx unknown
- 1996-12-18 HU HU9603495A patent/HU223340B1/hu not_active IP Right Cessation
- 1996-12-18 CO CO96066475A patent/CO4480100A1/es unknown
- 1996-12-18 CA CA002193337A patent/CA2193337C/en not_active Expired - Fee Related
- 1996-12-19 AU AU75471/96A patent/AU705970B2/en not_active Ceased
- 1996-12-19 JP JP34002996A patent/JP3987598B2/ja not_active Expired - Lifetime
- 1996-12-19 CN CN96123243A patent/CN1071309C/zh not_active Expired - Fee Related
- 1996-12-19 US US08/769,744 patent/US5801201A/en not_active Expired - Lifetime
- 1996-12-19 PL PL96317595A patent/PL185813B1/pl not_active IP Right Cessation
- 1996-12-19 IL IL11986496A patent/IL119864A/en not_active IP Right Cessation
- 1996-12-19 RU RU96123973/04A patent/RU2167148C2/ru not_active IP Right Cessation
- 1996-12-20 KR KR1019960068479A patent/KR100439283B1/ko not_active IP Right Cessation
-
1998
- 1998-02-06 HK HK98100931A patent/HK1001860A1/xx not_active IP Right Cessation
-
2000
- 2000-01-26 GR GR20000400182T patent/GR3032486T3/el unknown
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