JP2003516414A5 - - Google Patents
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- Publication number
- JP2003516414A5 JP2003516414A5 JP2001543569A JP2001543569A JP2003516414A5 JP 2003516414 A5 JP2003516414 A5 JP 2003516414A5 JP 2001543569 A JP2001543569 A JP 2001543569A JP 2001543569 A JP2001543569 A JP 2001543569A JP 2003516414 A5 JP2003516414 A5 JP 2003516414A5
- Authority
- JP
- Japan
- Prior art keywords
- eplerenone
- solvate
- type
- compound
- solvate compound
- 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.)
- Withdrawn
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 description 183
- 229960001208 eplerenone Drugs 0.000 description 183
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 129
- 239000012453 solvate Substances 0.000 description 110
- 150000001875 compounds Chemical class 0.000 description 109
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- 238000000634 powder X-ray diffraction Methods 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 239000013078 crystal Substances 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 37
- 229940088679 drug related substance Drugs 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 239000008186 active pharmaceutical agent Substances 0.000 description 30
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 29
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 27
- 238000000113 differential scanning calorimetry Methods 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000002245 particle Substances 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
- 238000002411 thermogravimetry Methods 0.000 description 20
- 238000002425 crystallisation Methods 0.000 description 19
- 230000008025 crystallization Effects 0.000 description 19
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 13
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 13
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 13
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 13
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 12
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
- 230000003993 interaction Effects 0.000 description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 10
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 229940090181 propyl acetate Drugs 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000004807 desolvation Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 125000000457 gamma-lactone group Chemical group 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000011276 addition treatment Methods 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- 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 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- PHMHDRYYFAYWEG-UHFFFAOYSA-N Rhapontigenin Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(O)=CC(O)=C1 PHMHDRYYFAYWEG-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920003350 Spectratech® Polymers 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16969099P | 1999-12-08 | 1999-12-08 | |
| US16955699P | 1999-12-08 | 1999-12-08 | |
| US16968299P | 1999-12-08 | 1999-12-08 | |
| US16980799P | 1999-12-08 | 1999-12-08 | |
| US16960899P | 1999-12-08 | 1999-12-08 | |
| US16963999P | 1999-12-08 | 1999-12-08 | |
| US60/169,690 | 1999-12-08 | ||
| US60/169,608 | 1999-12-08 | ||
| US60/169,682 | 1999-12-08 | ||
| US60/169,807 | 1999-12-08 | ||
| US60/169,556 | 1999-12-08 | ||
| US60/169,639 | 1999-12-08 | ||
| PCT/US2000/032416 WO2001042272A2 (en) | 1999-12-08 | 2000-12-04 | Eplerenone crystalline form exhibiting enhanced dissolution rate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003516414A JP2003516414A (ja) | 2003-05-13 |
| JP2003516414A5 true JP2003516414A5 (https=) | 2005-12-22 |
Family
ID=27558585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001543569A Withdrawn JP2003516414A (ja) | 1999-12-08 | 2000-12-04 | より高い溶解速度を示すエプレレノン結晶形 |
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) | NZ530028A (https=) |
| PE (1) | PE20010917A1 (https=) |
| WO (1) | WO2001042272A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040072797A1 (en) * | 2002-03-20 | 2004-04-15 | Pornanong Aramwit | 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 |
| ES2566934T3 (es) | 2010-05-10 | 2016-04-18 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Métodos y composiciones para el tratamiento de la acumulación de líquido en y/o bajo la retina |
| US9241944B2 (en) | 2010-06-16 | 2016-01-26 | Institut National De La Santé Et De La Recherche Médicale (Inserm) | Methods and compositions for stimulating reepithelialisation during wound healing |
| WO2017064121A1 (en) | 2015-10-13 | 2017-04-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of choroidal neovascularisation |
| 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 |
| WO2023031277A1 (en) | 2021-08-31 | 2023-03-09 | INSERM (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 |
|---|---|---|---|---|
| FI77669C (fi) * | 1983-04-13 | 1989-04-10 | Ciba Geigy Ag | 20-spiroxaner och analoger, som innehaoller en oeppen ring e, foerfarande foer deras framstaellning samt dessa innehaollande farmaceutiska preparat. |
| PT944644E (pt) * | 1996-12-11 | 2003-02-28 | Searle & Co | Processos para a preparacao de esteroides 9,11-epoxi e intermediarios uteis para esse efeito |
| IL145237A0 (en) * | 1999-03-05 | 2002-06-30 | Searle & Co | Combination therapy of angiotensin converting enzyme inhibitor and epoxy-steroidal aldosterone antagonist for treatment of cardiovascular disease |
-
2000
- 2000-12-04 MX MXPA01008056A patent/MXPA01008056A/es not_active Application Discontinuation
- 2000-12-04 EA EA200100871A patent/EA007934B1/ru not_active IP Right Cessation
- 2000-12-04 WO PCT/US2000/032416 patent/WO2001042272A2/en not_active Ceased
- 2000-12-04 HU HU0203032A patent/HUP0203032A3/hu unknown
- 2000-12-04 CN CNB008057788A patent/CN1152886C/zh not_active Expired - Fee Related
- 2000-12-04 JP JP2001543569A patent/JP2003516414A/ja not_active Withdrawn
- 2000-12-04 BR BR0008057-8A patent/BR0008057A/pt not_active IP Right Cessation
- 2000-12-04 EP EP00983781A patent/EP1177204A2/en not_active Withdrawn
- 2000-12-04 CA CA002362669A patent/CA2362669A1/en not_active Abandoned
- 2000-12-04 NZ NZ530028A patent/NZ530028A/en not_active IP Right Cessation
- 2000-12-04 CN CNA2004100368081A patent/CN1557833A/zh active Pending
- 2000-12-04 NZ NZ513961A patent/NZ513961A/xx not_active IP Right Cessation
- 2000-12-04 KR KR1020017010043A patent/KR100607923B1/ko not_active Expired - Fee Related
- 2000-12-04 IL IL14476400A patent/IL144764A0/xx active IP Right Grant
- 2000-12-04 AU AU20492/01A patent/AU784946B2/en not_active Ceased
- 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
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