ZA200200437B - Crystals of the sodium salt of pravastatin. - Google Patents
Crystals of the sodium salt of pravastatin. Download PDFInfo
- Publication number
- ZA200200437B ZA200200437B ZA200200437A ZA200200437A ZA200200437B ZA 200200437 B ZA200200437 B ZA 200200437B ZA 200200437 A ZA200200437 A ZA 200200437A ZA 200200437 A ZA200200437 A ZA 200200437A ZA 200200437 B ZA200200437 B ZA 200200437B
- Authority
- ZA
- South Africa
- Prior art keywords
- pravastatin
- sodium salt
- ethyl acetate
- crystals
- process according
- Prior art date
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- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 title claims description 59
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 title claims description 58
- 229960002965 pravastatin Drugs 0.000 title claims description 58
- 159000000000 sodium salts Chemical class 0.000 title claims description 49
- 239000013078 crystal Substances 0.000 title claims description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 238000002425 crystallisation Methods 0.000 claims description 18
- 230000008025 crystallization Effects 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000002441 X-ray diffraction Methods 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 8
- -1 sodium cations Chemical class 0.000 claims description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 5
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- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
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- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 229940127557 pharmaceutical product Drugs 0.000 claims description 2
- OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 claims 1
- VWBQYTRBTXKKOG-IYNICTALSA-M pravastatin sodium Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 VWBQYTRBTXKKOG-IYNICTALSA-M 0.000 description 15
- 229960001495 pravastatin sodium Drugs 0.000 description 15
- 239000000126 substance Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 2
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- SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 description 2
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- 229960003765 fluvastatin Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
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- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229960002855 simvastatin Drugs 0.000 description 2
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- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229940083542 sodium Drugs 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- NOJNFULGOQGBKB-UHFFFAOYSA-M sodium;3-[3-tert-butylsulfanyl-1-[[4-(6-ethoxypyridin-3-yl)phenyl]methyl]-5-[(5-methylpyridin-2-yl)methoxy]indol-2-yl]-2,2-dimethylpropanoate Chemical compound [Na+].C1=NC(OCC)=CC=C1C(C=C1)=CC=C1CN1C2=CC=C(OCC=3N=CC(C)=CC=3)C=C2C(SC(C)(C)C)=C1CC(C)(C)C([O-])=O NOJNFULGOQGBKB-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/33—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with hydroxy compounds having more than three hydroxy groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI9900191A SI20305A (sl) | 1999-08-06 | 1999-08-06 | Kristali natrijeve soli pravastatina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200437B true ZA200200437B (en) | 2003-03-26 |
Family
ID=20432515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200437A ZA200200437B (en) | 1999-08-06 | 2002-01-17 | Crystals of the sodium salt of pravastatin. |
Country Status (24)
| Country | Link |
|---|---|
| US (3) | US7078558B1 (sl) |
| EP (1) | EP1200385B2 (sl) |
| JP (1) | JP2003506424A (sl) |
| KR (2) | KR20070086847A (sl) |
| CN (1) | CN1205172C (sl) |
| AT (1) | ATE287389T1 (sl) |
| BG (1) | BG65368B1 (sl) |
| CA (1) | CA2379335A1 (sl) |
| CZ (1) | CZ2002414A3 (sl) |
| DE (1) | DE60017568T2 (sl) |
| DK (1) | DK1200385T3 (sl) |
| ES (1) | ES2235911T5 (sl) |
| HR (1) | HRP20020106A2 (sl) |
| HU (1) | HUP0202536A3 (sl) |
| IL (3) | IL148050A0 (sl) |
| NZ (1) | NZ516685A (sl) |
| PL (1) | PL365850A1 (sl) |
| PT (1) | PT1200385E (sl) |
| RU (1) | RU2247711C2 (sl) |
| SI (2) | SI20305A (sl) |
| SK (1) | SK1742002A3 (sl) |
| WO (1) | WO2001010813A1 (sl) |
| YU (1) | YU5402A (sl) |
| ZA (1) | ZA200200437B (sl) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI20070A (sl) * | 1998-09-18 | 2000-04-30 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Nove soli inhibitorjev HMG-CoA reduktaze |
| SI20305A (sl) * | 1999-08-06 | 2001-02-28 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Kristali natrijeve soli pravastatina |
| WO2001043723A1 (en) * | 1999-12-14 | 2001-06-21 | Biogal Gyogyszergyar Rt. | Novel forms of pravastatin sodium |
| JP2002121172A (ja) * | 2000-10-16 | 2002-04-23 | Sankyo Co Ltd | プラバスタチン又はその薬理上許容される塩の精製方法 |
| JP3236282B1 (ja) * | 2000-10-16 | 2001-12-10 | 三共株式会社 | プラバスタチンを精製する方法 |
| WO2002057229A1 (en) | 2001-01-19 | 2002-07-25 | Biocon India Limited | FORM V CRYSTALLINE [R-(R*,R*)]-2-(4-FLUOROPHENYL)-ß,$G(D)-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-[(PHENYLAMINO)CARBONYL]-1H-PYRROLE-1- HEPTANOIC ACID HEMI CALCIUM SALT. (ATORVASTATIN) |
| US6716615B2 (en) | 2002-02-27 | 2004-04-06 | Yung Shin Pharmaceutical Ind. Co., Ltd. | Strains of saccharaothrix, process for producing pravastatin using the strains and isolation process of (HMG)-CoA reductase |
| CZ2004943A3 (cs) | 2002-03-18 | 2005-02-16 | Biocon Limited | Amorfní HMG-CoA inhibitory obsahující reduktázu s požadovanou velikostí částic |
| JP4622855B2 (ja) * | 2003-06-10 | 2011-02-02 | 大正製薬株式会社 | 放射球状晶析物およびその製造方法並びにこれを利用するドライパウダー製剤 |
| CN1293874C (zh) * | 2003-08-18 | 2007-01-10 | 李朝晖 | 以洛伐他汀盐为主要活性成分的中药红曲及其制剂 |
| CA2546377A1 (en) | 2003-11-24 | 2005-06-09 | Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag | Method of purifying pravastatin |
| WO2005084669A1 (en) * | 2004-03-01 | 2005-09-15 | Lek Pharmaceuticals D.D. | Pharmaceutical composition |
| KR20070038553A (ko) | 2004-08-06 | 2007-04-10 | 트렌스폼 파마수티컬스 인코퍼레이티드 | 신규한 스타틴 약제학적 조성물 및 관련된 치료방법 |
| JP2008516890A (ja) * | 2004-08-06 | 2008-05-22 | トランスフオーム・フアーマシユーチカルズ・インコーポレーテツド | 新規なフェノフィブラート製剤および関連治療方法 |
| US20090042979A1 (en) * | 2004-08-06 | 2009-02-12 | Transform Pharmaceuticals Inc. | Novel Statin Pharmaceutical Compositions and Related Methods of Treatment |
| US20060194984A1 (en) * | 2005-02-09 | 2006-08-31 | Vilmos Keri | Methods of making pravastatin sodium |
| JP4895510B2 (ja) * | 2005-02-23 | 2012-03-14 | 株式会社トクヤマ | バリオールアミンの製造方法 |
| JP4813841B2 (ja) * | 2005-07-25 | 2011-11-09 | キユーピー株式会社 | プラバスタチンナトリウムの製造方法 |
| WO2009148709A1 (en) * | 2008-04-16 | 2009-12-10 | University Of Utah Research Foundation | Pharmacological targeting of vascular malformations |
| CN101348476B (zh) * | 2008-09-05 | 2011-05-11 | 丽珠集团新北江制药股份有限公司 | 一种制备4,5,6,7-四氢普伐他汀及其钠盐的方法和固体结晶形式 |
| CN101648867B (zh) * | 2009-09-04 | 2012-07-11 | 天津大学 | 一种普伐他汀钠晶型及其制备方法和应用 |
| EP2343054A1 (en) | 2010-01-04 | 2011-07-13 | LEK Pharmaceuticals d.d. | Pellets and microparticles of pravastatin sodium and a process of making them |
| CN102533893A (zh) * | 2010-12-09 | 2012-07-04 | 浙江海正药业股份有限公司 | 一种制备莫那可林j的方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS572240A (en) * | 1980-06-06 | 1982-01-07 | Sankyo Co Ltd | Ml-236b derivative |
| MX7065E (es) * | 1980-06-06 | 1987-04-10 | Sankyo Co | Un procedimiento microbiologico para preparar derivados de ml-236b |
| JPS5889191A (ja) * | 1981-11-20 | 1983-05-27 | Sankyo Co Ltd | ３−ヒドロキシ−ｍｌ−２３６ｂ誘導体の製造法 |
| CA2040865C (en) | 1990-05-15 | 2002-07-23 | James L. Bergey | Method for preventing, stabilizing or causing regression of atherosclerosis employing a combination of a cholesterol lowering drug and an ace inhibitor |
| KR100210482B1 (ko) * | 1997-04-10 | 1999-07-15 | 김종인 | 스트렙토마이세스엑스포리아투스(streptomycesexfoliatus)yj-118과이를이용한프라바스타틴나트륨의제조방법 |
| US6098031A (en) | 1998-03-05 | 2000-08-01 | Gsi Lumonics, Inc. | Versatile method and system for high speed, 3D imaging of microscopic targets |
| SI20072A (sl) * | 1998-09-18 | 2000-04-30 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Postopek za pridobivanje inhibitorjev HMG-CoA reduktaze |
| SI20305A (sl) * | 1999-08-06 | 2001-02-28 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Kristali natrijeve soli pravastatina |
| SI20070A (sl) * | 1998-09-18 | 2000-04-30 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Nove soli inhibitorjev HMG-CoA reduktaze |
| US6682913B1 (en) * | 1999-02-03 | 2004-01-27 | Institute For Drug Research Ltd. | Microbial process for preparing pravastatin |
| CN1260344C (zh) * | 1999-02-03 | 2006-06-21 | 药物研究所有限公司 | 培养物 |
-
1999
- 1999-08-06 SI SI9900191A patent/SI20305A/sl not_active IP Right Cessation
-
2000
- 2000-08-04 CZ CZ2002414A patent/CZ2002414A3/cs unknown
- 2000-08-04 SI SI200030653T patent/SI1200385T2/sl unknown
- 2000-08-04 US US10/049,093 patent/US7078558B1/en not_active Expired - Fee Related
- 2000-08-04 IL IL14805000A patent/IL148050A0/xx unknown
- 2000-08-04 WO PCT/IB2000/001103 patent/WO2001010813A1/en active Application Filing
- 2000-08-04 DE DE60017568T patent/DE60017568T2/de not_active Expired - Lifetime
- 2000-08-04 HU HU0202536A patent/HUP0202536A3/hu unknown
- 2000-08-04 RU RU2002102862/04A patent/RU2247711C2/ru not_active IP Right Cessation
- 2000-08-04 YU YU5402A patent/YU5402A/sh unknown
- 2000-08-04 EP EP00946239A patent/EP1200385B2/en not_active Expired - Lifetime
- 2000-08-04 SK SK174-2002A patent/SK1742002A3/sk not_active Application Discontinuation
- 2000-08-04 CA CA002379335A patent/CA2379335A1/en not_active Abandoned
- 2000-08-04 DK DK00946239T patent/DK1200385T3/da active
- 2000-08-04 JP JP2001515281A patent/JP2003506424A/ja active Pending
- 2000-08-04 NZ NZ516685A patent/NZ516685A/en not_active IP Right Cessation
- 2000-08-04 KR KR1020077015051A patent/KR20070086847A/ko not_active Application Discontinuation
- 2000-08-04 AT AT00946239T patent/ATE287389T1/de not_active IP Right Cessation
- 2000-08-04 PT PT00946239T patent/PT1200385E/pt unknown
- 2000-08-04 KR KR1020027001231A patent/KR100766928B1/ko not_active IP Right Cessation
- 2000-08-04 ES ES00946239T patent/ES2235911T5/es not_active Expired - Lifetime
- 2000-08-04 PL PL00365850A patent/PL365850A1/xx not_active Application Discontinuation
- 2000-08-04 CN CNB008113653A patent/CN1205172C/zh not_active Expired - Fee Related
-
2002
- 2002-01-17 ZA ZA200200437A patent/ZA200200437B/en unknown
- 2002-02-04 HR HR20020106A patent/HRP20020106A2/hr not_active Application Discontinuation
- 2002-02-05 BG BG106389A patent/BG65368B1/bg unknown
- 2002-02-06 IL IL148050A patent/IL148050A/en not_active IP Right Cessation
-
2003
- 2003-04-04 US US10/408,012 patent/US6740775B1/en not_active Expired - Fee Related
-
2006
- 2006-04-10 US US11/400,872 patent/US20060183929A1/en not_active Abandoned
-
2007
- 2007-11-08 IL IL187261A patent/IL187261A0/en unknown
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