CA2293324A1 - Maleate de 5-(2-ethyl-2h-tetrazole-5-yl)-1-methyle-1,2,3,6-tetrahydropyridine - Google Patents
Maleate de 5-(2-ethyl-2h-tetrazole-5-yl)-1-methyle-1,2,3,6-tetrahydropyridine Download PDFInfo
- Publication number
- CA2293324A1 CA2293324A1 CA002293324A CA2293324A CA2293324A1 CA 2293324 A1 CA2293324 A1 CA 2293324A1 CA 002293324 A CA002293324 A CA 002293324A CA 2293324 A CA2293324 A CA 2293324A CA 2293324 A1 CA2293324 A1 CA 2293324A1
- Authority
- CA
- Canada
- Prior art keywords
- acid addition
- addition salt
- ethyl
- methyl
- maleic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- YKFYFAAWVQGVTP-BTJKTKAUSA-N (z)-but-2-enedioic acid;5-(2-ethyltetrazol-5-yl)-1-methyl-3,6-dihydro-2h-pyridine Chemical compound OC(=O)\C=C/C(O)=O.CCN1N=NC(C=2CN(C)CCC=2)=N1 YKFYFAAWVQGVTP-BTJKTKAUSA-N 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- RNMOMKCRCIRYCZ-UHFFFAOYSA-N Alvameline Chemical compound CCN1N=NC(C=2CN(C)CCC=2)=N1 RNMOMKCRCIRYCZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 8
- 208000035475 disorder Diseases 0.000 claims abstract description 7
- 230000007257 malfunction Effects 0.000 claims abstract description 5
- 230000003551 muscarinic effect Effects 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims abstract 6
- 229960004373 acetylcholine Drugs 0.000 claims abstract 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 23
- 208000028017 Psychotic disease Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 230000009529 traumatic brain injury Effects 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 7
- 239000003937 drug carrier Substances 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002775 capsule Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 3
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 208000020186 Schizophreniform disease Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000001713 cholinergic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- AUFIRGPROMANKW-UHFFFAOYSA-N 1-methyl-3,6-dihydro-2h-pyridine Chemical compound CN1CCC=CC1 AUFIRGPROMANKW-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010008088 Cerebral artery embolism Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- 206010010254 Concussion Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- 102000007207 Muscarinic M1 Receptor Human genes 0.000 description 1
- 108010008406 Muscarinic M1 Receptor Proteins 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 206010007776 catatonia Diseases 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000009514 concussion Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000003906 hydrocephalus Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 201000010849 intracranial embolism Diseases 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 208000024817 paranoid personality disease Diseases 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003053 piperidines Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 238000001238 wet grinding Methods 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
- A61P25/18—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
La présente invention concerne un sel d'addition d'acide maléique de 5-(2-éthyl-2H-tétrazol-5-yl)-1-méthyl-1,2,3,6-tétrahydropyridine, des compositions pharmaceutiques contenant ledit sel d'addition d'acide ainsi que leur utilisation dans le traitement de troubles provoqués par un dysfonctionnement du système de l'acétylcholine (AcCh) ou du système muscarinique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK78197 | 1997-07-01 | ||
| DK0781/97 | 1997-07-01 | ||
| PCT/DK1998/000294 WO1999001448A1 (fr) | 1997-07-01 | 1998-07-01 | Maleate de 5-(2-ethyl-2h-tetrazole-5-yl)-1-methyle-1,2,3,6-tetrahydropyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2293324A1 true CA2293324A1 (fr) | 1999-01-14 |
Family
ID=8097489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002293324A Abandoned CA2293324A1 (fr) | 1997-07-01 | 1998-07-01 | Maleate de 5-(2-ethyl-2h-tetrazole-5-yl)-1-methyle-1,2,3,6-tetrahydropyridine |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0994869A1 (fr) |
| JP (1) | JP2002507215A (fr) |
| KR (1) | KR20010014297A (fr) |
| CN (1) | CN1261361A (fr) |
| AR (1) | AR013096A1 (fr) |
| AU (1) | AU735751B2 (fr) |
| BG (1) | BG103933A (fr) |
| BR (1) | BR9810331A (fr) |
| CA (1) | CA2293324A1 (fr) |
| CO (1) | CO4940483A1 (fr) |
| EA (1) | EA200000081A1 (fr) |
| HU (1) | HUP0002876A2 (fr) |
| IL (1) | IL133093A0 (fr) |
| IS (1) | IS5278A (fr) |
| JO (1) | JO2031B1 (fr) |
| MA (1) | MA25138A1 (fr) |
| NO (1) | NO996580D0 (fr) |
| PE (1) | PE116099A1 (fr) |
| PL (1) | PL337184A1 (fr) |
| SK (1) | SK187399A3 (fr) |
| TN (1) | TNSN98120A1 (fr) |
| TR (1) | TR199903283T2 (fr) |
| UY (2) | UY25069A1 (fr) |
| WO (1) | WO1999001448A1 (fr) |
| ZA (1) | ZA985498B (fr) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8714789D0 (en) * | 1987-06-24 | 1987-07-29 | Lundbeck & Co As H | Heterocyclic compounds |
| CZ287441B6 (en) * | 1995-11-06 | 2000-11-15 | Lundbeck & Co As H | Pharmaceutical preparation for treating traumatic lesion of brain |
-
1998
- 1998-06-18 AR ARP980102925A patent/AR013096A1/es not_active Application Discontinuation
- 1998-06-24 ZA ZA985498A patent/ZA985498B/xx unknown
- 1998-06-25 PE PE1998000563A patent/PE116099A1/es not_active Application Discontinuation
- 1998-06-25 JO JO19982031A patent/JO2031B1/en active
- 1998-06-26 CO CO98036576A patent/CO4940483A1/es unknown
- 1998-06-29 UY UY25069A patent/UY25069A1/es not_active Application Discontinuation
- 1998-06-30 TN TNTNSN98120A patent/TNSN98120A1/fr unknown
- 1998-07-01 BR BR9810331-8A patent/BR9810331A/pt not_active Application Discontinuation
- 1998-07-01 MA MA25155A patent/MA25138A1/fr unknown
- 1998-07-01 KR KR1019997012429A patent/KR20010014297A/ko not_active Ceased
- 1998-07-01 IL IL13309398A patent/IL133093A0/xx unknown
- 1998-07-01 EP EP98930655A patent/EP0994869A1/fr not_active Withdrawn
- 1998-07-01 JP JP50616699A patent/JP2002507215A/ja active Pending
- 1998-07-01 CN CN98806497A patent/CN1261361A/zh active Pending
- 1998-07-01 WO PCT/DK1998/000294 patent/WO1999001448A1/fr not_active Ceased
- 1998-07-01 HU HU0002876A patent/HUP0002876A2/hu unknown
- 1998-07-01 CA CA002293324A patent/CA2293324A1/fr not_active Abandoned
- 1998-07-01 SK SK1873-99A patent/SK187399A3/sk unknown
- 1998-07-01 TR TR1999/03283T patent/TR199903283T2/xx unknown
- 1998-07-01 AU AU81020/98A patent/AU735751B2/en not_active Ceased
- 1998-07-01 EA EA200000081A patent/EA200000081A1/ru unknown
- 1998-07-01 PL PL98337184A patent/PL337184A1/xx unknown
- 1998-09-10 UY UY25177A patent/UY25177A1/es not_active Application Discontinuation
-
1999
- 1999-11-30 IS IS5278A patent/IS5278A/is unknown
- 1999-11-30 BG BG103933A patent/BG103933A/xx unknown
- 1999-12-30 NO NO996580A patent/NO996580D0/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BG103933A (en) | 2000-07-31 |
| IS5278A (is) | 1999-11-30 |
| MA25138A1 (fr) | 2001-04-02 |
| JP2002507215A (ja) | 2002-03-05 |
| PL337184A1 (en) | 2000-08-14 |
| AU8102098A (en) | 1999-01-25 |
| JO2031B1 (en) | 1999-05-15 |
| EP0994869A1 (fr) | 2000-04-26 |
| AR013096A1 (es) | 2000-12-13 |
| WO1999001448A1 (fr) | 1999-01-14 |
| BR9810331A (pt) | 2000-09-05 |
| UY25069A1 (es) | 1998-12-21 |
| NO996580L (no) | 1999-12-30 |
| KR20010014297A (ko) | 2001-02-26 |
| SK187399A3 (en) | 2000-06-12 |
| PE116099A1 (es) | 1999-11-23 |
| TNSN98120A1 (fr) | 2005-03-15 |
| TR199903283T2 (xx) | 2000-06-21 |
| IL133093A0 (en) | 2001-03-19 |
| NO996580D0 (no) | 1999-12-30 |
| ZA985498B (en) | 1999-01-20 |
| HUP0002876A2 (hu) | 2001-06-28 |
| EA200000081A1 (ru) | 2000-08-28 |
| CN1261361A (zh) | 2000-07-26 |
| UY25177A1 (es) | 2000-12-29 |
| AU735751B2 (en) | 2001-07-12 |
| CO4940483A1 (es) | 2000-07-24 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |