IL130003A - 1 - Phenylalkyl - 6,3,2,1 - Tetrahydropyridines for the treatment of Alzheimer's disease - Google Patents
1 - Phenylalkyl - 6,3,2,1 - Tetrahydropyridines for the treatment of Alzheimer's diseaseInfo
- Publication number
- IL130003A IL130003A IL13000397A IL13000397A IL130003A IL 130003 A IL130003 A IL 130003A IL 13000397 A IL13000397 A IL 13000397A IL 13000397 A IL13000397 A IL 13000397A IL 130003 A IL130003 A IL 130003A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- group
- alkoxy
- ethyl
- salts
- Prior art date
Links
- 208000024827 Alzheimer disease Diseases 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- -1 phenoxy, phenylamino Chemical group 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 12
- 239000012453 solvate Substances 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000005504 styryl group Chemical group 0.000 claims abstract description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 206010039966 Senile dementia Diseases 0.000 claims description 5
- 238000002636 symptomatic treatment Methods 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 40
- 239000000047 product Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
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- 235000011152 sodium sulphate Nutrition 0.000 description 10
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- HAKSOKWVNPZVNM-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine;hydrochloride Chemical compound Cl.C1CNC=CC1 HAKSOKWVNPZVNM-UHFFFAOYSA-N 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
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- 229940079593 drug Drugs 0.000 description 5
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- 238000006243 chemical reaction Methods 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- 235000012222 talc Nutrition 0.000 description 1
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- XVFJONKUSLSKSW-JTQLQIEISA-N talsaclidine Chemical compound C1CC2[C@@H](OCC#C)CN1CC2 XVFJONKUSLSKSW-JTQLQIEISA-N 0.000 description 1
- 229950001645 talsaclidine Drugs 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- UEKQSLXYFDHEJR-UHFFFAOYSA-N tributylstannane;hydrochloride Chemical compound Cl.CCCC[SnH](CCCC)CCCC UEKQSLXYFDHEJR-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229950001843 velnacrine Drugs 0.000 description 1
- JOLJIIDDOBNFHW-UHFFFAOYSA-N xanomeline Chemical compound CCCCCCOC1=NSN=C1C1=CCCN(C)C1 JOLJIIDDOBNFHW-UHFFFAOYSA-N 0.000 description 1
- 229950006755 xanomeline Drugs 0.000 description 1
- 229950004402 zifrosilone Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9615335A FR2757160B1 (fr) | 1996-12-13 | 1996-12-13 | 1-phenylalkyl-1,2,3,6-tetrahydropyridines |
| PCT/FR1997/002286 WO1998025903A1 (fr) | 1996-12-13 | 1997-12-12 | 1-phenylalkyl-1,2,3,6-tetrahydropyridines pour le traitement de la maladie d'alzheimer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL130003A0 IL130003A0 (en) | 2000-02-29 |
| IL130003A true IL130003A (en) | 2004-09-27 |
Family
ID=9498641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13000397A IL130003A (en) | 1996-12-13 | 1997-12-12 | 1 - Phenylalkyl - 6,3,2,1 - Tetrahydropyridines for the treatment of Alzheimer's disease |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6034090A (ko) |
| EP (1) | EP0950048B1 (ko) |
| JP (1) | JP3881384B2 (ko) |
| KR (1) | KR100560358B1 (ko) |
| CN (1) | CN1129579C (ko) |
| AT (1) | ATE202561T1 (ko) |
| AU (1) | AU730143B2 (ko) |
| BR (1) | BR9713916A (ko) |
| CA (1) | CA2275353C (ko) |
| CY (1) | CY2274B1 (ko) |
| CZ (1) | CZ289789B6 (ko) |
| DE (1) | DE69705429T2 (ko) |
| DK (1) | DK0950048T3 (ko) |
| EE (1) | EE03763B1 (ko) |
| ES (1) | ES2160977T3 (ko) |
| FR (1) | FR2757160B1 (ko) |
| GR (1) | GR3036643T3 (ko) |
| HK (1) | HK1023997A1 (ko) |
| HU (1) | HU224347B1 (ko) |
| IL (1) | IL130003A (ko) |
| IS (1) | IS1969B (ko) |
| NO (1) | NO312720B1 (ko) |
| NZ (1) | NZ336033A (ko) |
| PL (1) | PL190789B1 (ko) |
| PT (1) | PT950048E (ko) |
| RS (1) | RS49807B (ko) |
| RU (1) | RU2189975C2 (ko) |
| SI (1) | SI0950048T1 (ko) |
| SK (1) | SK283331B6 (ko) |
| TR (1) | TR199901291T2 (ko) |
| UA (1) | UA52707C2 (ko) |
| WO (1) | WO1998025903A1 (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2763847B1 (fr) * | 1997-05-28 | 2003-06-06 | Sanofi Sa | Utilisation de tetrahydropyridines 4-substituees pour fabriquer des medicaments agissant sur le tgf-beta-1 |
| UA81749C2 (uk) * | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| FR2832405B1 (fr) * | 2001-11-19 | 2004-12-10 | Sanofi Synthelabo | Tetrahydropyridyl-alkyl-heterocycles azotes, procede pour leur preparation et compositions pharmaceutiques les contenant |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1321701A (en) * | 1969-10-01 | 1973-06-27 | Continental Pharma | Amino-alcohols their salts and process for prepairing the same |
| IE34545B1 (en) * | 1969-10-01 | 1975-06-11 | Continental Pharma | Amino-alcohols,their salts and process for preparing the same |
| FR2650505B1 (fr) * | 1989-08-07 | 1994-06-03 | Midy Spa | Utilisation de trifluoromethylphenyltetrahydropyridines pour la preparation de medicaments destines a combattre les troubles de la motricite intestinale |
| FR2662355B1 (fr) * | 1990-05-22 | 1994-11-10 | Sanofi Sa | Utilisation de la 1-[2-(2-naphtyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine pour la preparation de medicaments destines au traitement de troubles cerebraux et neuronaux. |
| HU211019B (en) * | 1991-12-02 | 1995-09-28 | Richter Gedeon Vegyeszet | Process for producing new 1,2,3,6-tetrahydropyridine and piperidine derivatives substituted with n-(hydroxylalkyl) group and compositions comprising such compounds |
-
1996
- 1996-12-13 FR FR9615335A patent/FR2757160B1/fr not_active Expired - Fee Related
-
1997
- 1997-12-12 IL IL13000397A patent/IL130003A/en not_active IP Right Cessation
- 1997-12-12 BR BR9713916-5A patent/BR9713916A/pt not_active Application Discontinuation
- 1997-12-12 ES ES97951323T patent/ES2160977T3/es not_active Expired - Lifetime
- 1997-12-12 EP EP97951323A patent/EP0950048B1/fr not_active Expired - Lifetime
- 1997-12-12 NZ NZ336033A patent/NZ336033A/xx unknown
- 1997-12-12 SK SK786-99A patent/SK283331B6/sk unknown
- 1997-12-12 TR TR1999/01291T patent/TR199901291T2/xx unknown
- 1997-12-12 JP JP52632098A patent/JP3881384B2/ja not_active Expired - Fee Related
- 1997-12-12 UA UA99063286A patent/UA52707C2/uk unknown
- 1997-12-12 KR KR1019997005203A patent/KR100560358B1/ko not_active IP Right Cessation
- 1997-12-12 SI SI9730187T patent/SI0950048T1/xx unknown
- 1997-12-12 US US09/331,006 patent/US6034090A/en not_active Expired - Fee Related
- 1997-12-12 RU RU99115083/04A patent/RU2189975C2/ru not_active IP Right Cessation
- 1997-12-12 CZ CZ19992113A patent/CZ289789B6/cs not_active IP Right Cessation
- 1997-12-12 AU AU54893/98A patent/AU730143B2/en not_active Ceased
- 1997-12-12 CN CN97180581A patent/CN1129579C/zh not_active Expired - Fee Related
- 1997-12-12 DK DK97951323T patent/DK0950048T3/da active
- 1997-12-12 PL PL334071A patent/PL190789B1/pl unknown
- 1997-12-12 AT AT97951323T patent/ATE202561T1/de not_active IP Right Cessation
- 1997-12-12 PT PT97951323T patent/PT950048E/pt unknown
- 1997-12-12 CA CA002275353A patent/CA2275353C/en not_active Expired - Fee Related
- 1997-12-12 EE EEP199900237A patent/EE03763B1/xx not_active IP Right Cessation
- 1997-12-12 HU HU0001185A patent/HU224347B1/hu not_active IP Right Cessation
- 1997-12-12 DE DE69705429T patent/DE69705429T2/de not_active Expired - Fee Related
- 1997-12-12 RS YUP-243/99A patent/RS49807B/sr unknown
- 1997-12-12 WO PCT/FR1997/002286 patent/WO1998025903A1/fr not_active Application Discontinuation
-
1999
- 1999-06-10 IS IS5075A patent/IS1969B/is unknown
- 1999-06-11 NO NO19992869A patent/NO312720B1/no unknown
-
2000
- 2000-05-30 HK HK00103181A patent/HK1023997A1/xx not_active IP Right Cessation
-
2001
- 2001-09-18 GR GR20010401501T patent/GR3036643T3/el not_active IP Right Cessation
-
2002
- 2002-05-15 CY CY0200027A patent/CY2274B1/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |