CA2362669A1 - Eplerenone crystalline form exhibiting enhanced dissolution rate - Google Patents
Eplerenone crystalline form exhibiting enhanced dissolution rate Download PDFInfo
- Publication number
- CA2362669A1 CA2362669A1 CA002362669A CA2362669A CA2362669A1 CA 2362669 A1 CA2362669 A1 CA 2362669A1 CA 002362669 A CA002362669 A CA 002362669A CA 2362669 A CA2362669 A CA 2362669A CA 2362669 A1 CA2362669 A1 CA 2362669A1
- Authority
- CA
- Canada
- Prior art keywords
- eplerenone
- solvent
- solvate
- crystalline
- ethyl ketone
- 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
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 title claims abstract description 561
- 229960001208 eplerenone Drugs 0.000 title claims abstract description 556
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- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims abstract description 6
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940037627 magnesium lauryl sulfate Drugs 0.000 description 1
- HBNDBUATLJAUQM-UHFFFAOYSA-L magnesium;dodecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O HBNDBUATLJAUQM-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 231100000544 menstrual irregularity Toxicity 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 229940073555 nonoxynol-10 Drugs 0.000 description 1
- 229920004918 nonoxynol-9 Polymers 0.000 description 1
- 229940087419 nonoxynol-9 Drugs 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 229940098514 octoxynol-9 Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940061037 optivar Drugs 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 235000011185 polyoxyethylene (40) stearate Nutrition 0.000 description 1
- 239000001194 polyoxyethylene (40) stearate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000002398 sedimentation field-flow fractionation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229940005573 sodium fumarate Drugs 0.000 description 1
- 235000019294 sodium fumarate Nutrition 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000000547 structure data Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 229960004224 tyloxapol Drugs 0.000 description 1
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
- 229920001664 tyloxapol Polymers 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
- C07J71/0015—Oxiranes at position 9(11)
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- 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
- A61P25/24—Antidepressants
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurology (AREA)
- Gastroenterology & Hepatology (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16963999P | 1999-12-08 | 1999-12-08 | |
| US16968299P | 1999-12-08 | 1999-12-08 | |
| US16960899P | 1999-12-08 | 1999-12-08 | |
| US16955699P | 1999-12-08 | 1999-12-08 | |
| US16969099P | 1999-12-08 | 1999-12-08 | |
| US16980799P | 1999-12-08 | 1999-12-08 | |
| US60/169,556 | 1999-12-08 | ||
| US60/169,608 | 1999-12-08 | ||
| US60/169,639 | 1999-12-08 | ||
| US60/169,682 | 1999-12-08 | ||
| US60/169,690 | 1999-12-08 | ||
| US60/169,807 | 1999-12-08 | ||
| PCT/US2000/032416 WO2001042272A2 (en) | 1999-12-08 | 2000-12-04 | Eplerenone crystalline form exhibiting enhanced dissolution rate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2362669A1 true CA2362669A1 (en) | 2001-06-14 |
Family
ID=27558585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002362669A Abandoned CA2362669A1 (en) | 1999-12-08 | 2000-12-04 | Eplerenone crystalline form exhibiting enhanced dissolution rate |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1177204A2 (https=) |
| JP (1) | JP2003516414A (https=) |
| KR (1) | KR100607923B1 (https=) |
| CN (2) | CN1152886C (https=) |
| AU (1) | AU784946B2 (https=) |
| BR (1) | BR0008057A (https=) |
| CA (1) | CA2362669A1 (https=) |
| CO (1) | CO5280211A1 (https=) |
| EA (1) | EA007934B1 (https=) |
| HU (1) | HUP0203032A3 (https=) |
| IL (3) | IL144764A0 (https=) |
| MX (1) | MXPA01008056A (https=) |
| MY (1) | MY131878A (https=) |
| NO (1) | NO20013856L (https=) |
| NZ (2) | NZ513961A (https=) |
| PE (1) | PE20010917A1 (https=) |
| WO (1) | WO2001042272A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1487540A2 (en) * | 2002-03-20 | 2004-12-22 | Pharmacia Corporation | Storage stable eplerenone formulation |
| US7235655B2 (en) | 2002-03-22 | 2007-06-26 | Pharmacia & Upjohn Company | Processes to prepare eplerenone |
| CA2582496A1 (en) | 2007-03-20 | 2008-09-20 | Apotex Pharmachem Inc. | Improved process for the preparation and purification of eplerenone |
| EP2977084B1 (en) | 2010-05-10 | 2017-07-05 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and compositions for the treatment of fluid accumulation in and/ or under the retina |
| JP6180930B2 (ja) | 2010-06-16 | 2017-08-16 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 創傷治癒過程における再上皮化を刺激するための方法及び組成物 |
| JP6835836B2 (ja) | 2015-10-13 | 2021-02-24 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 脈絡膜血管新生の処置のための方法及び医薬組成物 |
| GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| EP3490606B8 (en) | 2016-07-26 | 2024-04-10 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Antagonist of mineralocorticoid receptor for the treatment of osteoarthritis |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| CN108059648A (zh) * | 2017-12-30 | 2018-05-22 | 合肥久诺医药科技有限公司 | 一种依普利酮溶剂合物及其制备方法 |
| US20240366632A1 (en) | 2021-08-31 | 2024-11-07 | Institut National de la Santé et de la Recherche Médicale | Methods for the treatment of ocular rosacea |
| WO2023204729A1 (ru) * | 2022-04-19 | 2023-10-26 | Общество с ограниченной ответственностью "Гелеспон" | Фармацевтические композиции на основе новой субстанции 4-[2-(1н-имидазол-4-ил)-этилкарбамоил]-бутановой кислоты и способ получения субстанции |
| CN120754115A (zh) * | 2025-05-23 | 2025-10-10 | 远大医药（中国）有限公司 | 一种含依普利酮组合物及其药物制剂、制备方法和用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559332A (en) * | 1983-04-13 | 1985-12-17 | Ciba Geigy Corporation | 20-Spiroxanes and analogues having an open ring E, processes for their manufacture, and pharmaceutical preparations thereof |
| WO1998025948A2 (en) * | 1996-12-11 | 1998-06-18 | G.D. Searle & Co. | Processes for preparation of 9,11-epoxy steroids and intermediates useful therein |
| DE60005159T2 (de) * | 1999-03-05 | 2004-07-22 | G.D. Searle Llc, Chicago | Kombinationstherapie von angiotensin-konvertierendem enzym hemmer und epoxy-steroidalem aldosteron antagonist zur behandlung von kardiovaskulären erkrankungen |
-
2000
- 2000-12-04 WO PCT/US2000/032416 patent/WO2001042272A2/en not_active Ceased
- 2000-12-04 MX MXPA01008056A patent/MXPA01008056A/es not_active Application Discontinuation
- 2000-12-04 BR BR0008057-8A patent/BR0008057A/pt not_active IP Right Cessation
- 2000-12-04 JP JP2001543569A patent/JP2003516414A/ja not_active Withdrawn
- 2000-12-04 CA CA002362669A patent/CA2362669A1/en not_active Abandoned
- 2000-12-04 HU HU0203032A patent/HUP0203032A3/hu unknown
- 2000-12-04 NZ NZ513961A patent/NZ513961A/xx not_active IP Right Cessation
- 2000-12-04 IL IL14476400A patent/IL144764A0/xx active IP Right Grant
- 2000-12-04 CN CNB008057788A patent/CN1152886C/zh not_active Expired - Fee Related
- 2000-12-04 CN CNA2004100368081A patent/CN1557833A/zh active Pending
- 2000-12-04 AU AU20492/01A patent/AU784946B2/en not_active Ceased
- 2000-12-04 EP EP00983781A patent/EP1177204A2/en not_active Withdrawn
- 2000-12-04 EA EA200100871A patent/EA007934B1/ru not_active IP Right Cessation
- 2000-12-04 NZ NZ530028A patent/NZ530028A/en not_active IP Right Cessation
- 2000-12-04 KR KR1020017010043A patent/KR100607923B1/ko not_active Expired - Fee Related
- 2000-12-06 MY MYPI20005734A patent/MY131878A/en unknown
- 2000-12-06 PE PE2000001300A patent/PE20010917A1/es not_active Application Discontinuation
- 2000-12-11 CO CO00094075A patent/CO5280211A1/es not_active Application Discontinuation
-
2001
- 2001-08-06 IL IL144764A patent/IL144764A/en not_active IP Right Cessation
- 2001-08-08 NO NO20013856A patent/NO20013856L/no not_active Application Discontinuation
-
2006
- 2006-06-22 IL IL176511A patent/IL176511A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0203032A2 (hu) | 2002-12-28 |
| EA007934B1 (ru) | 2007-02-27 |
| CN1557833A (zh) | 2004-12-29 |
| CN1377365A (zh) | 2002-10-30 |
| MXPA01008056A (es) | 2003-07-21 |
| EP1177204A2 (en) | 2002-02-06 |
| AU784946B2 (en) | 2006-08-03 |
| HUP0203032A3 (en) | 2003-04-28 |
| PE20010917A1 (es) | 2001-09-10 |
| CN1152886C (zh) | 2004-06-09 |
| MY131878A (en) | 2007-09-28 |
| NZ513961A (en) | 2004-02-27 |
| EA200100871A1 (ru) | 2002-04-25 |
| NO20013856L (no) | 2001-10-08 |
| WO2001042272A2 (en) | 2001-06-14 |
| WO2001042272A3 (en) | 2001-11-29 |
| WO2001042272A9 (en) | 2002-12-12 |
| CO5280211A1 (es) | 2003-05-30 |
| NO20013856D0 (no) | 2001-08-08 |
| IL144764A (en) | 2007-08-19 |
| BR0008057A (pt) | 2002-04-23 |
| NZ530028A (en) | 2005-08-26 |
| IL144764A0 (en) | 2002-06-30 |
| IL176511A (en) | 2007-08-19 |
| KR100607923B1 (ko) | 2006-08-04 |
| JP2003516414A (ja) | 2003-05-13 |
| KR20010112261A (ko) | 2001-12-20 |
| AU2049201A (en) | 2001-06-18 |
| HK1050536A1 (en) | 2003-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |