NO330436B1 - Anvendelse av 3-(1H-imidazol-4-yl-metyl)-indan-5-ol og lignende til fremstilling av et legemiddel for intraspinal administrering for a oppna analgesi eller som et hjelpemiddel til anestesi - Google Patents
Anvendelse av 3-(1H-imidazol-4-yl-metyl)-indan-5-ol og lignende til fremstilling av et legemiddel for intraspinal administrering for a oppna analgesi eller som et hjelpemiddel til anestesi Download PDFInfo
- Publication number
- NO330436B1 NO330436B1 NO20011545A NO20011545A NO330436B1 NO 330436 B1 NO330436 B1 NO 330436B1 NO 20011545 A NO20011545 A NO 20011545A NO 20011545 A NO20011545 A NO 20011545A NO 330436 B1 NO330436 B1 NO 330436B1
- Authority
- NO
- Norway
- Prior art keywords
- indan
- imidazol
- methyl
- drug
- administered
- Prior art date
Links
- VTZPAJGVRWKMAG-UHFFFAOYSA-N 3-(1h-imidazol-5-ylmethyl)-2,3-dihydro-1h-inden-5-ol Chemical compound C12=CC(O)=CC=C2CCC1CC1=CN=CN1 VTZPAJGVRWKMAG-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 230000036592 analgesia Effects 0.000 title claims abstract description 33
- 239000003814 drug Substances 0.000 title claims abstract description 31
- 229940079593 drug Drugs 0.000 title claims abstract description 26
- 206010002091 Anaesthesia Diseases 0.000 title claims abstract description 11
- 230000037005 anaesthesia Effects 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 150000002148 esters Chemical class 0.000 claims abstract description 19
- 241000124008 Mammalia Species 0.000 claims abstract description 17
- 208000002193 Pain Diseases 0.000 claims description 9
- 230000036407 pain Effects 0.000 claims description 6
- OYKZVKWXOWICFI-UHFFFAOYSA-N 3-(1h-imidazol-1-ium-4-ylmethyl)-2,3-dihydro-1h-inden-5-ol;chloride Chemical compound Cl.C12=CC(O)=CC=C2CCC1CC1=CN=CN1 OYKZVKWXOWICFI-UHFFFAOYSA-N 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 206010033892 Paraplegia Diseases 0.000 claims description 3
- 208000004550 Postoperative Pain Diseases 0.000 claims description 3
- 208000032930 Spastic paraplegia Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 25
- 238000000034 method Methods 0.000 abstract description 10
- 206010039897 Sedation Diseases 0.000 abstract description 8
- 230000036280 sedation Effects 0.000 abstract description 8
- 238000001949 anaesthesia Methods 0.000 abstract description 4
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 24
- 229960002896 clonidine Drugs 0.000 description 23
- 241000700159 Rattus Species 0.000 description 19
- 230000000202 analgesic effect Effects 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 230000001624 sedative effect Effects 0.000 description 8
- 238000007913 intrathecal administration Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 231100000673 dose–response relationship Toxicity 0.000 description 5
- 230000005176 gastrointestinal motility Effects 0.000 description 5
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- 230000002411 adverse Effects 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
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- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- 206010058019 Cancer Pain Diseases 0.000 description 2
- ZNIFSRGNXRYGHF-UHFFFAOYSA-N Clonidine hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1NC1=NCCN1 ZNIFSRGNXRYGHF-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- 208000007914 Labor Pain Diseases 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 230000008499 blood brain barrier function Effects 0.000 description 2
- 210000001218 blood-brain barrier Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960002925 clonidine hydrochloride Drugs 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000036543 hypotension Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 230000006742 locomotor activity Effects 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 208000021722 neuropathic pain Diseases 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000000215 1-octanols Chemical class 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
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- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000023178 Musculoskeletal disease Diseases 0.000 description 1
- 101100136062 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) PE10 gene Proteins 0.000 description 1
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- 206010033799 Paralysis Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038678 Respiratory depression Diseases 0.000 description 1
- 206010040030 Sensory loss Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000001793 Wilcoxon signed-rank test Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 229940073153 duraclon Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 238000003304 gavage Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000004 hemodynamic effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 description 1
- 229960003793 midazolam Drugs 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 210000005166 vasculature Anatomy 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
-
- 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
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10198698P | 1998-09-28 | 1998-09-28 | |
| PCT/FI1999/000793 WO2000018400A1 (en) | 1998-09-28 | 1999-09-27 | Use of 3-(1h-imidazol-4-ylmethyl)-indan-5-ol in the manufacture of a medicament for intraspinal, intrathecal or epidural administration |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20011545D0 NO20011545D0 (no) | 2001-03-26 |
| NO20011545L NO20011545L (no) | 2001-03-26 |
| NO330436B1 true NO330436B1 (no) | 2011-04-11 |
Family
ID=22287519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20011545A NO330436B1 (no) | 1998-09-28 | 2001-03-26 | Anvendelse av 3-(1H-imidazol-4-yl-metyl)-indan-5-ol og lignende til fremstilling av et legemiddel for intraspinal administrering for a oppna analgesi eller som et hjelpemiddel til anestesi |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6495584B1 (de) |
| EP (1) | EP1117399B1 (de) |
| JP (1) | JP4647785B2 (de) |
| KR (1) | KR100646811B1 (de) |
| CN (1) | CN1320034A (de) |
| AT (1) | ATE288753T1 (de) |
| AU (1) | AU756104B2 (de) |
| BG (1) | BG105469A (de) |
| CA (1) | CA2345521C (de) |
| CZ (1) | CZ299918B6 (de) |
| DE (1) | DE69923698T2 (de) |
| DK (1) | DK1117399T3 (de) |
| EA (1) | EA003216B1 (de) |
| EE (1) | EE200100193A (de) |
| ES (1) | ES2237205T3 (de) |
| HK (1) | HK1039751A1 (de) |
| HU (1) | HU227634B1 (de) |
| IL (2) | IL141680A0 (de) |
| NO (1) | NO330436B1 (de) |
| NZ (1) | NZ510233A (de) |
| PL (1) | PL346908A1 (de) |
| SK (1) | SK3812001A3 (de) |
| UA (1) | UA61152C2 (de) |
| WO (1) | WO2000018400A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1196168A2 (de) * | 1999-06-25 | 2002-04-17 | Orion Corporation | Verfahren zur verabreichung eines imidazolderivats um analgesie zu erhalten |
| FI20022159A0 (fi) | 2002-12-05 | 2002-12-05 | Orion Corp | Uusia farmaseuttisia yhdisteitä |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI894911A0 (fi) * | 1989-10-17 | 1989-10-17 | Farmos Oy | En terapeutiskt vaerdefull foerening. |
| GB9520150D0 (en) | 1995-10-03 | 1995-12-06 | Orion Yhtymae Oy | New imidazole derivatives |
| US5801188A (en) * | 1997-01-08 | 1998-09-01 | Medtronic Inc. | Clonidine therapy enhancement |
-
1999
- 1999-09-27 KR KR1020017003511A patent/KR100646811B1/ko active IP Right Grant
- 1999-09-27 PL PL99346908A patent/PL346908A1/xx not_active Application Discontinuation
- 1999-09-27 EA EA200100405A patent/EA003216B1/ru not_active IP Right Cessation
- 1999-09-27 NZ NZ510233A patent/NZ510233A/en not_active IP Right Cessation
- 1999-09-27 US US09/787,886 patent/US6495584B1/en not_active Expired - Lifetime
- 1999-09-27 SK SK381-2001A patent/SK3812001A3/sk unknown
- 1999-09-27 DK DK99969677T patent/DK1117399T3/da active
- 1999-09-27 IL IL14168099A patent/IL141680A0/xx active IP Right Grant
- 1999-09-27 DE DE69923698T patent/DE69923698T2/de not_active Expired - Lifetime
- 1999-09-27 CN CN99811480A patent/CN1320034A/zh active Pending
- 1999-09-27 EE EEP200100193A patent/EE200100193A/xx unknown
- 1999-09-27 HU HU0103864A patent/HU227634B1/hu unknown
- 1999-09-27 AT AT99969677T patent/ATE288753T1/de not_active IP Right Cessation
- 1999-09-27 EP EP99969677A patent/EP1117399B1/de not_active Expired - Lifetime
- 1999-09-27 JP JP2000571918A patent/JP4647785B2/ja not_active Expired - Lifetime
- 1999-09-27 CZ CZ20010933A patent/CZ299918B6/cs not_active IP Right Cessation
- 1999-09-27 AU AU59860/99A patent/AU756104B2/en not_active Expired
- 1999-09-27 WO PCT/FI1999/000793 patent/WO2000018400A1/en active IP Right Grant
- 1999-09-27 CA CA002345521A patent/CA2345521C/en not_active Expired - Lifetime
- 1999-09-27 UA UA2001042926A patent/UA61152C2/uk unknown
- 1999-09-27 ES ES99969677T patent/ES2237205T3/es not_active Expired - Lifetime
-
2001
- 2001-02-27 IL IL141680A patent/IL141680A/en not_active IP Right Cessation
- 2001-03-26 NO NO20011545A patent/NO330436B1/no not_active IP Right Cessation
- 2001-04-25 BG BG105469A patent/BG105469A/xx unknown
-
2002
- 2002-02-22 HK HK02101329.8A patent/HK1039751A1/zh unknown
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| MK1K | Patent expired |