UY25439A1 - Procedimiento para la preparacion de 1,2,3,4,5,6-hexahidro-2,6-metano-3-benzazocin-10-oles sustituidos - Google Patents
Procedimiento para la preparacion de 1,2,3,4,5,6-hexahidro-2,6-metano-3-benzazocin-10-oles sustituidosInfo
- Publication number
- UY25439A1 UY25439A1 UY25439A UY25439A UY25439A1 UY 25439 A1 UY25439 A1 UY 25439A1 UY 25439 A UY25439 A UY 25439A UY 25439 A UY25439 A UY 25439A UY 25439 A1 UY25439 A1 UY 25439A1
- Authority
- UY
- Uruguay
- Prior art keywords
- hydrogen
- methyl
- derivative
- alkylene
- benzazocin
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- ZNMPXGQFIKLPTD-UHFFFAOYSA-N 1-(dichloromethyl)-2-methoxybenzene Chemical compound COC1=CC=CC=C1C(Cl)Cl ZNMPXGQFIKLPTD-UHFFFAOYSA-N 0.000 abstract 1
- SJPVZEOHRLQKQN-UHFFFAOYSA-N 2-benzylpyridine;hydrochloride Chemical compound Cl.C=1C=CC=NC=1CC1=CC=CC=C1 SJPVZEOHRLQKQN-UHFFFAOYSA-N 0.000 abstract 1
- 201000006474 Brain Ischemia Diseases 0.000 abstract 1
- 206010008120 Cerebral ischaemia Diseases 0.000 abstract 1
- 208000007101 Muscle Cramp Diseases 0.000 abstract 1
- 208000005392 Spasm Diseases 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 206010003119 arrhythmia Diseases 0.000 abstract 1
- 230000006793 arrhythmia Effects 0.000 abstract 1
- 208000028683 bipolar I disease Diseases 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000002490 cerebral effect Effects 0.000 abstract 1
- 206010008118 cerebral infarction Diseases 0.000 abstract 1
- -1 chloro, bromo, hydroxy, methyl Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 230000001419 dependent effect Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 208000031225 myocardial ischemia Diseases 0.000 abstract 1
- 230000004770 neurodegeneration Effects 0.000 abstract 1
- 208000015122 neurodegenerative disease Diseases 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000003195 sodium channel blocking agent Substances 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/26—Benzomorphans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- 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
- A61P25/08—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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
La presente invención se refiere a procedimientos para la preparación de nuevos 1,2,3,4,5,6-hexahidro-2,6-metano-3-benzazocin-10-oles sustituidos, de fórmula general (I), en donde: X puede significar un enlace sencillo, O, alquileno, un puente de alquileno con 1 a 8 átomos de carbono que puede estar ramificado o sin ramificar, y puede presentar, en cualquier posición del puente, uno o dos átomos de oxígeno, preferentemente O-alquileno ó O-CH2-CH2-O, O-CH2-CH2-NH; R1 puede ser hidrógeno, metilo, etilo, fenilo; R2 puede ser hidrógeno o metilo; R3 puede ser hidrógeno, fluoro, cloro, bromo, hidroxi, metilo, metoxi; R4, R5 y R6 pueden ser independientemente hidrógeno, metilo, etilo; R7 puede ser t-butilo, ciclohexilo, fenilo eventualmente sustituido; R8 puede ser hidrógeno o alquilo. Por ejemplo: (-)-(1R,2"S)-2-(2"-benciloxi)propil-4'-hidroxi-5,9,9-trimetil-6,7-benzomorfano. Un procedimiento para preparar norbenzomorfanos de fórmula general (5) consiste en: a) se hace reaccionar cloruro de o-metoxiclorobencilo con cloruro de bencilpiridino, para proporcionar la tetrahidropiridina; b) se transforma el derivado de tetrahidropiridina en el derivado de N-bencilbenzomorfano; c) se desbencila el nitrógeno amínico para proporcionar el derivado de metoxibenzomorfano; y d) se aísla el fenol-éter y el derivado de benzomorfano. Los compuestos de esta invención son bloquedores del canal de sodio dependiente del potencial y por lo tanto se utilizan como aniconvulsivantes, pueden ser empleados para la terapia de la ciclofrenia (enfermedad maníacodepresiva) y también en enfermedades cuya causa esté basada en la sobreexcitación como ser arritmias, espamos, isquemias cerebrales y cardíacas, enfermedades neurodegenerativas, etc.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19740110A DE19740110A1 (de) | 1997-09-12 | 1997-09-12 | Substituierte 1,2,3,4,5,6-Hexahydro-2,6-methano-3-benzazocin-10-ole, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| UY25175A UY25175A1 (es) | 1997-09-12 | 1998-09-09 | 1,2,3,4,5,6-hexahidro-2,6-metano-3-benzazocin-10-oles sustituidos, procedimientos para su preparación, y empleo de los mismos como medicamentos. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UY25439A1 true UY25439A1 (es) | 1999-11-17 |
Family
ID=7842134
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UY25175A UY25175A1 (es) | 1997-09-12 | 1998-09-09 | 1,2,3,4,5,6-hexahidro-2,6-metano-3-benzazocin-10-oles sustituidos, procedimientos para su preparación, y empleo de los mismos como medicamentos. |
| UY25439A UY25439A1 (es) | 1997-09-12 | 1999-03-22 | Procedimiento para la preparacion de 1,2,3,4,5,6-hexahidro-2,6-metano-3-benzazocin-10-oles sustituidos |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UY25175A UY25175A1 (es) | 1997-09-12 | 1998-09-09 | 1,2,3,4,5,6-hexahidro-2,6-metano-3-benzazocin-10-oles sustituidos, procedimientos para su preparación, y empleo de los mismos como medicamentos. |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US6455538B1 (es) |
| EP (1) | EP1015433B1 (es) |
| JP (1) | JP3827528B2 (es) |
| KR (1) | KR100601008B1 (es) |
| CN (1) | CN1166640C (es) |
| AR (1) | AR017095A1 (es) |
| AT (1) | ATE267811T1 (es) |
| AU (1) | AU751036B2 (es) |
| BG (1) | BG64418B1 (es) |
| BR (1) | BR9812443A (es) |
| CA (1) | CA2302347C (es) |
| CO (1) | CO5011117A1 (es) |
| CZ (1) | CZ296909B6 (es) |
| DE (2) | DE19740110A1 (es) |
| DK (1) | DK1015433T3 (es) |
| EE (1) | EE04398B1 (es) |
| ES (1) | ES2222612T3 (es) |
| HR (1) | HRP980502B1 (es) |
| HU (1) | HUP0004588A3 (es) |
| ID (1) | ID24173A (es) |
| IL (1) | IL134572A (es) |
| MY (1) | MY120550A (es) |
| NO (1) | NO315650B1 (es) |
| NZ (1) | NZ503710A (es) |
| PE (1) | PE122899A1 (es) |
| PL (1) | PL198486B1 (es) |
| PT (1) | PT1015433E (es) |
| RS (1) | RS49888B (es) |
| RU (1) | RU2218334C2 (es) |
| SA (1) | SA98190765B1 (es) |
| SK (1) | SK284670B6 (es) |
| TR (1) | TR200000697T2 (es) |
| TW (1) | TW505645B (es) |
| UA (1) | UA61973C2 (es) |
| UY (2) | UY25175A1 (es) |
| WO (1) | WO1999014199A1 (es) |
| YU (1) | YU12000A (es) |
| ZA (1) | ZA988285B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19826365A1 (de) * | 1998-06-12 | 1999-12-16 | Gruenenthal Gmbh | Verwendung von Benzomorphanderivaten als Analgetikum |
| US6355652B1 (en) | 1999-11-27 | 2002-03-12 | Boehringer Ingelheim Pharma Kg | Substituted 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines and their use as pharmaceutical compositions |
| DE19957156A1 (de) * | 1999-11-27 | 2001-05-31 | Boehringer Ingelheim Pharma | Substituierte 1,2,3,4,5,6-Hexahydro-2,6-methano-3-benzazocine und ihre Verwendung als Arzneimittel |
| US6683089B2 (en) | 2002-02-02 | 2004-01-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | N-allyoxyethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine-10-ols |
| DE10204276A1 (de) * | 2002-02-02 | 2003-08-07 | Boehringer Ingelheim Pharma | N-Allyloxyethyl-1,2,3,4,5,6-Hexahydro-2,6-methano-3-benzazocine und ihre Verwendung als Arzneimittel |
| US20040019075A1 (en) * | 2002-05-29 | 2004-01-29 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New formulation for the parenteral application of crobenetine |
| DE10223783A1 (de) * | 2002-05-29 | 2003-12-11 | Boehringer Ingelheim Pharma | Neue Formulierung zur parenteralen Applikation eines Na-Kanal-Blockers |
| US6828311B2 (en) | 2002-05-29 | 2004-12-07 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Formulation for the parenteral application of a sodium channel blocker |
| US20030235576A1 (en) * | 2002-06-15 | 2003-12-25 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New drug combinations for the treatment of ischaemic conditions |
| DE10226814A1 (de) * | 2002-06-15 | 2004-01-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkombinationen zur Behandlung ischämischer Zustände |
| RS54522B1 (en) | 2005-12-22 | 2016-06-30 | Newron Pharmaceuticals S.P.A. | 2-Phenylethylamino Derivatives as Modulators of Calcium and (or Sodium) Channels |
| CN101687773B (zh) | 2007-06-15 | 2014-07-30 | 纽朗制药有限公司 | 取代的2-[2-(苯基)乙氨基]烷酰胺衍生物及其作为钠和/或钙通道调节剂的应用 |
| EA022973B1 (ru) | 2011-06-27 | 2016-03-31 | Ньюрон Фармасьютикалс С.П.А. | Фторированные арилалкиламинокарбоксамидные производные |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2828039A1 (de) * | 1978-06-26 | 1980-01-10 | Boehringer Sohn Ingelheim | 2-(2-alkoxyethyl)-2'-hydroxy-6,7-benzomorphane deren saeureadditionssalze diese enthaltende arzneimittel und verfahren zu deren herstellung |
| US4208523A (en) | 1978-11-30 | 1980-06-17 | Sterling Drug Inc. | 11-Lower-alkyl-, 11-phenyl-lower-alkyl- and 11-cyclo-lower-alkyl-lower-alkyl-hexahydro-2,6-methano-3-benzazocines |
| DE4121821A1 (de) * | 1991-07-02 | 1993-01-14 | Boehringer Ingelheim Kg | Neue benzomorphane und ihre verwendung als arzneimittel |
| US5607941A (en) * | 1992-06-26 | 1997-03-04 | Boehringer Ingelheim Kg | Useful for treating neurodegenerative diseases |
| DE19528472A1 (de) * | 1995-08-03 | 1997-02-06 | Boehringer Ingelheim Kg | Neues Verfahren zur Herstellung von Norbenzomorphan einer Zwischenstufe bei Herstellung von pharmazeutisch wertvollen Benzomorphanderivaten, insbesondere von (-)-(1R,5S,S"R)-3'-Hydroxy-2-(2-methoxypropyl-)-5,9,9-trimethyl-6,7 benzomorphan |
-
1997
- 1997-09-12 DE DE19740110A patent/DE19740110A1/de not_active Ceased
-
1998
- 1998-09-08 PE PE1998000847A patent/PE122899A1/es not_active Application Discontinuation
- 1998-09-09 DK DK98950009T patent/DK1015433T3/da active
- 1998-09-09 AT AT98950009T patent/ATE267811T1/de not_active IP Right Cessation
- 1998-09-09 CZ CZ20000894A patent/CZ296909B6/cs not_active IP Right Cessation
- 1998-09-09 EE EEP200000129A patent/EE04398B1/xx not_active IP Right Cessation
- 1998-09-09 JP JP2000511750A patent/JP3827528B2/ja not_active Expired - Fee Related
- 1998-09-09 SK SK334-2000A patent/SK284670B6/sk not_active IP Right Cessation
- 1998-09-09 PT PT98950009T patent/PT1015433E/pt unknown
- 1998-09-09 DE DE59811477T patent/DE59811477D1/de not_active Expired - Fee Related
- 1998-09-09 CA CA002302347A patent/CA2302347C/en not_active Expired - Fee Related
- 1998-09-09 PL PL339061A patent/PL198486B1/pl not_active IP Right Cessation
- 1998-09-09 RS YUP-120/00A patent/RS49888B/sr unknown
- 1998-09-09 ES ES98950009T patent/ES2222612T3/es not_active Expired - Lifetime
- 1998-09-09 HU HU0004588A patent/HUP0004588A3/hu unknown
- 1998-09-09 ID IDW20000461A patent/ID24173A/id unknown
- 1998-09-09 IL IL13457298A patent/IL134572A/xx not_active IP Right Cessation
- 1998-09-09 RU RU2000109358/04A patent/RU2218334C2/ru not_active IP Right Cessation
- 1998-09-09 TR TR2000/00697T patent/TR200000697T2/xx unknown
- 1998-09-09 UY UY25175A patent/UY25175A1/es not_active IP Right Cessation
- 1998-09-09 NZ NZ503710A patent/NZ503710A/xx unknown
- 1998-09-09 CN CNB988090155A patent/CN1166640C/zh not_active Expired - Fee Related
- 1998-09-09 BR BR9812443-9A patent/BR9812443A/pt not_active Application Discontinuation
- 1998-09-09 WO PCT/EP1998/005734 patent/WO1999014199A1/de active IP Right Grant
- 1998-09-09 AU AU96242/98A patent/AU751036B2/en not_active Ceased
- 1998-09-09 KR KR1020007002562A patent/KR100601008B1/ko not_active IP Right Cessation
- 1998-09-09 UA UA2000042088A patent/UA61973C2/uk unknown
- 1998-09-09 EP EP98950009A patent/EP1015433B1/de not_active Expired - Lifetime
- 1998-09-10 ZA ZA988285A patent/ZA988285B/xx unknown
- 1998-09-10 TW TW087115042A patent/TW505645B/zh active
- 1998-09-10 CO CO98052134A patent/CO5011117A1/es unknown
- 1998-09-10 MY MYPI98004142A patent/MY120550A/en unknown
- 1998-09-11 AR ARP980104530A patent/AR017095A1/es active Pending
- 1998-09-11 HR HR980502A patent/HRP980502B1/xx not_active IP Right Cessation
- 1998-11-16 SA SA98190765A patent/SA98190765B1/ar unknown
-
1999
- 1999-03-22 UY UY25439A patent/UY25439A1/es not_active IP Right Cessation
-
2000
- 2000-03-02 YU YU12000A patent/YU12000A/sh unknown
- 2000-03-09 BG BG104232A patent/BG64418B1/bg active Active
- 2000-03-10 US US09/523,473 patent/US6455538B1/en not_active Expired - Lifetime
- 2000-03-10 NO NO20001288A patent/NO315650B1/no not_active IP Right Cessation
Also Published As
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Effective date: 20190322 |