UA61152C2 - Drug for intraspinal administration comprising 3-(1h-imidazol-4-ylmethyl)-indan-5-ol, method for obtaining analgesia, method for treatment of mammals (variants) - Google Patents
Drug for intraspinal administration comprising 3-(1h-imidazol-4-ylmethyl)-indan-5-ol, method for obtaining analgesia, method for treatment of mammals (variants) Download PDFInfo
- Publication number
- UA61152C2 UA61152C2 UA2001042926A UA2001042926A UA61152C2 UA 61152 C2 UA61152 C2 UA 61152C2 UA 2001042926 A UA2001042926 A UA 2001042926A UA 2001042926 A UA2001042926 A UA 2001042926A UA 61152 C2 UA61152 C2 UA 61152C2
- Authority
- UA
- Ukraine
- Prior art keywords
- indan
- ylmethyl
- imidazol
- analgesia
- drug
- 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 abstract description 37
- 230000036592 analgesia Effects 0.000 title abstract description 24
- 239000003814 drug Substances 0.000 title abstract description 17
- 229940079593 drug Drugs 0.000 title abstract description 16
- 238000000034 method Methods 0.000 title abstract description 14
- 241000124008 Mammalia Species 0.000 title abstract description 13
- 230000000694 effects Effects 0.000 abstract description 20
- 150000003839 salts Chemical class 0.000 abstract description 13
- 150000002148 esters Chemical class 0.000 abstract description 12
- 206010002091 Anaesthesia Diseases 0.000 abstract description 6
- 230000037005 anaesthesia Effects 0.000 abstract description 6
- 206010039897 Sedation Diseases 0.000 abstract description 3
- 230000036280 sedation Effects 0.000 abstract description 3
- 238000001949 anaesthesia Methods 0.000 abstract 1
- 241000700159 Rattus Species 0.000 description 24
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 19
- 229960002896 clonidine Drugs 0.000 description 19
- 230000000202 analgesic effect Effects 0.000 description 13
- 230000001624 sedative effect Effects 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 238000007920 subcutaneous administration Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229940126062 Compound A Drugs 0.000 description 7
- 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 7
- 208000002193 Pain Diseases 0.000 description 7
- 238000005259 measurement Methods 0.000 description 6
- 230000037023 motor activity Effects 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
- 230000036407 pain Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- 230000002631 hypothermal effect Effects 0.000 description 4
- 230000004973 motor coordination Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000004899 motility Effects 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- -1 polyethylene Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 206010058019 Cancer Pain Diseases 0.000 description 2
- 208000000094 Chronic 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
- 208000007914 Labor Pain Diseases 0.000 description 2
- 208000035945 Labour pain Diseases 0.000 description 2
- 206010033892 Paraplegia Diseases 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 208000004550 Postoperative Pain Diseases 0.000 description 2
- 208000032930 Spastic paraplegia Diseases 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
- 230000008499 blood brain barrier function Effects 0.000 description 2
- 210000001218 blood-brain barrier Anatomy 0.000 description 2
- 230000036760 body temperature Effects 0.000 description 2
- 229960002925 clonidine hydrochloride Drugs 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 239000000203 mixture Substances 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
- 230000004044 response Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000003313 weakening effect Effects 0.000 description 2
- 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 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
- QCDFBFJGMNKBDO-UHFFFAOYSA-N Clioquinol Chemical class C1=CN=C2C(O)=C(I)C=C(Cl)C2=C1 QCDFBFJGMNKBDO-UHFFFAOYSA-N 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 241000282326 Felis catus Species 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
- 101100136062 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) PE10 gene Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000220317 Rosa Species 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229940124534 adjunct to anesthesia Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000002817 coal dust Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229960005220 fluanisone Drugs 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 230000005176 gastrointestinal motility Effects 0.000 description 1
- 230000026781 habituation 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- PEHSSTUGJUBZBI-UHFFFAOYSA-N indan-5-ol Chemical compound OC1=CC=C2CCCC2=C1 PEHSSTUGJUBZBI-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 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
- 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
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 210000002330 subarachnoid space Anatomy 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 210000000701 subdural space Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 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)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (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 (1)
| Publication Number | Publication Date |
|---|---|
| UA61152C2 true UA61152C2 (en) | 2003-11-17 |
Family
ID=22287519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001042926A UA61152C2 (en) | 1998-09-28 | 1999-09-27 | Drug for intraspinal administration comprising 3-(1h-imidazol-4-ylmethyl)-indan-5-ol, method for obtaining analgesia, method for treatment of mammals (variants) |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6495584B1 (cs) |
| EP (1) | EP1117399B1 (cs) |
| JP (1) | JP4647785B2 (cs) |
| KR (1) | KR100646811B1 (cs) |
| CN (1) | CN1320034A (cs) |
| AT (1) | ATE288753T1 (cs) |
| AU (1) | AU756104B2 (cs) |
| BG (1) | BG105469A (cs) |
| CA (1) | CA2345521C (cs) |
| CZ (1) | CZ299918B6 (cs) |
| DE (1) | DE69923698T2 (cs) |
| DK (1) | DK1117399T3 (cs) |
| EA (1) | EA003216B1 (cs) |
| EE (1) | EE200100193A (cs) |
| ES (1) | ES2237205T3 (cs) |
| HK (1) | HK1039751A1 (cs) |
| HU (1) | HU227634B1 (cs) |
| IL (2) | IL141680A0 (cs) |
| NO (1) | NO330436B1 (cs) |
| NZ (1) | NZ510233A (cs) |
| PL (1) | PL346908A1 (cs) |
| SK (1) | SK3812001A3 (cs) |
| UA (1) | UA61152C2 (cs) |
| WO (1) | WO2000018400A1 (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001000192A2 (en) * | 1999-06-25 | 2001-01-04 | Orion Corporation | Method of administering an imidazole derivative to obtain analgesia |
| FI20022159A0 (fi) * | 2002-12-05 | 2002-12-05 | Orion Corp | Uusia farmaseuttisia yhdisteitä |
| CN116617205A (zh) * | 2023-07-07 | 2023-08-22 | 生物岛实验室 | 乙酰丙酸茚满酯在预防和/或治疗肌肉萎缩相关疾病中的用途 |
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 SK SK381-2001A patent/SK3812001A3/sk unknown
- 1999-09-27 CN CN99811480A patent/CN1320034A/zh active Pending
- 1999-09-27 PL PL99346908A patent/PL346908A1/xx not_active Application Discontinuation
- 1999-09-27 JP JP2000571918A patent/JP4647785B2/ja not_active Expired - Lifetime
- 1999-09-27 WO PCT/FI1999/000793 patent/WO2000018400A1/en active IP Right Grant
- 1999-09-27 DE DE69923698T patent/DE69923698T2/de not_active Expired - Lifetime
- 1999-09-27 KR KR1020017003511A patent/KR100646811B1/ko not_active Expired - Lifetime
- 1999-09-27 EA EA200100405A patent/EA003216B1/ru not_active IP Right Cessation
- 1999-09-27 AT AT99969677T patent/ATE288753T1/de not_active IP Right Cessation
- 1999-09-27 DK DK99969677T patent/DK1117399T3/da active
- 1999-09-27 ES ES99969677T patent/ES2237205T3/es not_active Expired - Lifetime
- 1999-09-27 HU HU0103864A patent/HU227634B1/hu unknown
- 1999-09-27 UA UA2001042926A patent/UA61152C2/uk unknown
- 1999-09-27 IL IL14168099A patent/IL141680A0/xx active IP Right Grant
- 1999-09-27 US US09/787,886 patent/US6495584B1/en not_active Expired - Lifetime
- 1999-09-27 CZ CZ20010933A patent/CZ299918B6/cs not_active IP Right Cessation
- 1999-09-27 EP EP99969677A patent/EP1117399B1/en not_active Expired - Lifetime
- 1999-09-27 AU AU59860/99A patent/AU756104B2/en not_active Expired
- 1999-09-27 NZ NZ510233A patent/NZ510233A/en not_active IP Right Cessation
- 1999-09-27 CA CA002345521A patent/CA2345521C/en not_active Expired - Lifetime
- 1999-09-27 HK HK02101329.8A patent/HK1039751A1/zh unknown
- 1999-09-27 EE EEP200100193A patent/EE200100193A/xx unknown
-
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
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