TWI293290B - - Google Patents
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- Publication number
- TWI293290B TWI293290B TW090126305A TW90126305A TWI293290B TW I293290 B TWI293290 B TW I293290B TW 090126305 A TW090126305 A TW 090126305A TW 90126305 A TW90126305 A TW 90126305A TW I293290 B TWI293290 B TW I293290B
- Authority
- TW
- Taiwan
- Prior art keywords
- crystal
- solvent
- type crystal
- crystals
- type
- Prior art date
Links
- 239000013078 crystal Substances 0.000 claims abstract description 81
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 238000001035 drying Methods 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 5
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000006166 lysate Substances 0.000 claims description 3
- 230000002079 cooperative effect Effects 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims 1
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 abstract 3
- 229960000698 nateglinide Drugs 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000324375 | 2000-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI293290B true TWI293290B (cg-RX-API-DMAC10.html) | 2008-02-11 |
Family
ID=18801920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090126305A TWI293290B (cg-RX-API-DMAC10.html) | 2000-10-24 | 2001-10-24 |
Country Status (18)
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1283054A4 (en) * | 2000-03-17 | 2006-04-12 | Ajinomoto Kk | MEDICAMENTS FOR TREATING THE COMPLICATIONS OF DIABETES AND NEUROPATHIES AND USE THEREOF |
| CA2425533C (en) * | 2000-10-18 | 2010-04-20 | Ajinomoto Co., Inc. | Methods for producing acylphenylalanine |
| DE60129728T2 (de) * | 2000-10-18 | 2008-04-24 | Ajinomoto Co., Inc. | Verfahren zur herstellung von nateglinid-kristallen |
| DK1334720T3 (da) * | 2000-10-24 | 2009-01-19 | Ajinomoto Kk | Nateglinid-indeholdende fremstillinger |
| ES2321911T3 (es) * | 2000-10-24 | 2009-06-15 | Ajinomoto Kk | Preparaciones farmacologicas hidrofilas que contienen nateglinida. |
| EP1496048A4 (en) * | 2002-04-15 | 2006-08-02 | Ajinomoto Kk | NEW NATEGLINID CRYSTAL |
| US7411089B2 (en) | 2002-04-15 | 2008-08-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
| US6861553B2 (en) | 2002-07-03 | 2005-03-01 | Teva Pharmaceuticals Industries Ltd. | Process for preparing nateglinide and intermediates thereof |
| US7420084B2 (en) * | 2002-07-18 | 2008-09-02 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7148376B2 (en) | 2002-07-18 | 2006-12-12 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| WO2004009532A1 (en) * | 2002-07-18 | 2004-01-29 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7534913B2 (en) * | 2002-07-18 | 2009-05-19 | Teva Pharmaceutica Industries Ltd. | Crystalline form of nateglinide |
| US7358390B2 (en) | 2002-07-18 | 2008-04-15 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| EP1535900B1 (en) * | 2003-11-26 | 2006-12-27 | A.M.S.A. ANONIMA MATERIE SINTETICHE E AFFINI S.p.A. | Process for the preparation of nateglinide, preferably in b-form |
| CA2563793A1 (en) * | 2004-05-07 | 2005-11-24 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US20070231393A1 (en) * | 2004-05-19 | 2007-10-04 | University Of South Carolina | System and Device for Magnetic Drug Targeting with Magnetic Drug Carrier Particles |
| US20080096970A1 (en) * | 2004-05-20 | 2008-04-24 | Sundaram Venkataraman | Stable Nateglinide Form B Compositions |
| US7425648B2 (en) | 2005-01-03 | 2008-09-16 | A.M.S.A. Anonima Materie Sintetiche E. Affini S.P.A. | Process for the preparation of nateglinide, preferably in B-form |
| CN101111266A (zh) * | 2005-01-31 | 2008-01-23 | 味之素株式会社 | 含有降血糖药的用于改善或治疗糖耐量异常、临界性糖尿病、胰岛素抵抗性和高胰岛素血症的药物组合物 |
| WO2007135533A1 (en) * | 2006-05-23 | 2007-11-29 | Aurobindo Pharma Limited | Process for preparing nateglinide b-type crystals |
| KR100837843B1 (ko) * | 2006-12-26 | 2008-06-13 | 씨제이제일제당 (주) | 나테글리나이드 결정형, 그 제조방법, 및 그를 포함하는약제학적 조성물 |
| WO2011157986A1 (en) | 2010-06-14 | 2011-12-22 | Cipla Limited | A process for the preparation of nateglinide |
| US9303038B2 (en) | 2011-09-06 | 2016-04-05 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy and neurological diseases |
| US9642915B2 (en) | 2012-05-07 | 2017-05-09 | Cellix Bio Private Limited | Compositions and methods for the treatment of neuromuscular disorders and neurodegenerative diseases |
| WO2013167990A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of depression |
| CA2872975A1 (en) | 2012-05-07 | 2013-11-14 | Cellixbio Private Limited | Compositions and methods for the treatment of neurological disorders |
| US9434704B2 (en) | 2012-05-08 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological degenerative disorders |
| US9522884B2 (en) | 2012-05-08 | 2016-12-20 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic disorders |
| US9309233B2 (en) | 2012-05-08 | 2016-04-12 | Cellix Bio Private Limited | Compositions and methods for the treatment of blood clotting disorders |
| US9266823B2 (en) | 2012-05-08 | 2016-02-23 | Cellix Bio Private Limited | Compositions and methods for the treatment of parkinson's disease |
| JP2015521174A (ja) * | 2012-05-08 | 2015-07-27 | セリックスビオ プライヴェート リミテッド | 糖尿病の治療のための組成物および方法 |
| WO2013167992A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of inflammatory disorders |
| WO2013168015A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of asthma and allergy |
| US9573927B2 (en) | 2012-05-10 | 2017-02-21 | Cellix Bio Private Limited | Compositions and methods for the treatment of severe pain |
| WO2013168002A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological conditions |
| US9273061B2 (en) | 2012-05-10 | 2016-03-01 | Cellix Bio Private Limited | Compositions and methods for the treatment of chronic pain |
| US9346742B2 (en) | 2012-05-10 | 2016-05-24 | Cellix Bio Private Limited | Compositions and methods for the treatment of fibromyalgia pain |
| US9499527B2 (en) | 2012-05-10 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of familial amyloid polyneuropathy |
| US9403857B2 (en) | 2012-05-10 | 2016-08-02 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| WO2013168001A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| US9499526B2 (en) | 2012-05-10 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurologic diseases |
| WO2013167997A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic syndrome |
| WO2013168012A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of respiratory disorders |
| WO2013167999A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurologic diseases |
| US9339484B2 (en) | 2012-05-10 | 2016-05-17 | Cellix Bio Private Limited | Compositions and methods for the treatment of restless leg syndrome and fibromyalgia |
| EP2852570B1 (en) | 2012-05-23 | 2020-04-22 | Cellixbio Private Limited | Composition for the treatment of inflammatory bowel disease |
| WO2013175376A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of local pain |
| CA2873104A1 (en) | 2012-05-23 | 2013-11-28 | Cellixbio Private Limited | Compositions and methods for the treatment of mucositis |
| WO2013175347A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of respiratory disorders |
| CN104603097A (zh) | 2012-05-23 | 2015-05-06 | 塞利克斯比奥私人有限公司 | 用于治疗多发性硬化症的组合物和方法 |
| US9434729B2 (en) | 2012-05-23 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of periodontitis and rheumatoid arthritis |
| US9108942B1 (en) | 2014-11-05 | 2015-08-18 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| US9187427B2 (en) | 2012-08-03 | 2015-11-17 | Cellix Bio Private Limited | N-substituted nicotinamide compounds and compositions for the treatment migraine and neurologic diseases |
| US9624168B2 (en) | 2012-09-06 | 2017-04-18 | Cellix Bio Private Limited | Compositions and methods for the treatment inflammation and lipid disorders |
| CN104364231A (zh) | 2012-09-08 | 2015-02-18 | 塞利克斯比奥私人有限公司 | 用于治疗炎症和脂质异常的组合物和方法 |
| US9333187B1 (en) | 2013-05-15 | 2016-05-10 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory bowel disease |
| EP3004049B1 (en) | 2013-06-04 | 2018-09-05 | Cellixbio Private Limited | Compositions and methods for the treatment of diabetes and pre-diabetes |
| US9096537B1 (en) | 2014-12-31 | 2015-08-04 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
| EP3240779B1 (en) | 2014-09-26 | 2020-10-28 | Cellixbio Private Limited | Compositions and methods for the treatment of epilepsy and neurological disorders |
| WO2016051420A1 (en) | 2014-09-29 | 2016-04-07 | Cellix Bio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| EP3212626B1 (en) | 2014-10-27 | 2018-11-07 | Cellix Bio Private Limited | Three component salts of fumaric acid monomethyl ester with piperazine or ethylene diamine for the treatment of multiple sclerosis |
| US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
| US10208014B2 (en) | 2014-11-05 | 2019-02-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological disorders |
| US9150557B1 (en) | 2014-11-05 | 2015-10-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of hyperglycemia |
| US9173877B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
| US9284287B1 (en) | 2014-11-05 | 2016-03-15 | Cellix Bio Private Limited | Compositions and methods for the suppression of carbonic anhydrase activity |
| US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| CN104402756B (zh) * | 2014-11-27 | 2016-08-31 | 天方药业有限公司 | 一种高纯度那格列奈的制备方法 |
| US9932294B2 (en) | 2014-12-01 | 2018-04-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| SG11201705524SA (en) | 2015-01-06 | 2017-08-30 | Cellix Bio Private Ltd | Compositions and methods for the treatment of inflammation and pain |
| CN109369443A (zh) * | 2018-11-05 | 2019-02-22 | 扬子江药业集团江苏海慈生物药业有限公司 | 一种新的那格列奈h晶型的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6354321A (ja) * | 1985-03-27 | 1988-03-08 | Ajinomoto Co Inc | 血糖降下剤 |
| AU615966B2 (en) * | 1987-12-04 | 1991-10-17 | Takeda Chemical Industries Ltd. | Crystals of cephem hydrochloride |
| US5463116A (en) * | 1991-07-30 | 1995-10-31 | Ajinomoto Co., Inc. | Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them |
| DK0526171T3 (da) | 1991-07-30 | 1997-08-25 | Ajinomoto Kk | Krystaller af N-(trans-4-isopropylcyclohexylcarbonyl)-Dphenylalanin og fremgangsmåder til fremstilling deraf |
| DE69740161D1 (de) * | 1996-11-15 | 2011-05-12 | Ajinomoto Kk | Nateglinide-Tablettenzubereitungen |
| US6844006B1 (en) * | 1999-07-09 | 2005-01-18 | Pennfield Oil Company | Process and apparatus for the preparation of chlortetracycline-containing animal feed compositions |
| HK1049622A1 (en) * | 1999-12-28 | 2003-05-23 | Ajinomoto Co., Inc. | Oral preparations for diabetes |
| EP1283054A4 (en) * | 2000-03-17 | 2006-04-12 | Ajinomoto Kk | MEDICAMENTS FOR TREATING THE COMPLICATIONS OF DIABETES AND NEUROPATHIES AND USE THEREOF |
| DE60129728T2 (de) * | 2000-10-18 | 2008-04-24 | Ajinomoto Co., Inc. | Verfahren zur herstellung von nateglinid-kristallen |
| CA2425533C (en) * | 2000-10-18 | 2010-04-20 | Ajinomoto Co., Inc. | Methods for producing acylphenylalanine |
| DK1334720T3 (da) * | 2000-10-24 | 2009-01-19 | Ajinomoto Kk | Nateglinid-indeholdende fremstillinger |
| US7411089B2 (en) | 2002-04-15 | 2008-08-12 | Ajinomoto Co., Inc. | Nateglinide crystals |
-
2001
- 2001-10-23 DK DK01976819T patent/DK1334964T3/da active
- 2001-10-23 BR BR0114846-0A patent/BR0114846A/pt not_active IP Right Cessation
- 2001-10-23 PT PT01976819T patent/PT1334964E/pt unknown
- 2001-10-23 JP JP2002537707A patent/JP4225057B2/ja not_active Expired - Fee Related
- 2001-10-23 EP EP01976819A patent/EP1334964B1/en not_active Expired - Lifetime
- 2001-10-23 AU AU2001296001A patent/AU2001296001A1/en not_active Abandoned
- 2001-10-23 MX MXPA03003575A patent/MXPA03003575A/es active IP Right Grant
- 2001-10-23 RU RU2003111948/04A patent/RU2275354C2/ru not_active IP Right Cessation
- 2001-10-23 CN CNB018212999A patent/CN100422143C/zh not_active Expired - Fee Related
- 2001-10-23 AT AT01976819T patent/ATE370115T1/de active
- 2001-10-23 WO PCT/JP2001/009293 patent/WO2002034713A1/ja not_active Ceased
- 2001-10-23 KR KR1020037005671A patent/KR100810930B1/ko not_active Expired - Fee Related
- 2001-10-23 ES ES01976819T patent/ES2288997T3/es not_active Expired - Lifetime
- 2001-10-23 CA CA002426745A patent/CA2426745C/en not_active Expired - Fee Related
- 2001-10-23 DE DE60130014T patent/DE60130014T2/de not_active Expired - Lifetime
- 2001-10-24 TW TW090126305A patent/TWI293290B/zh not_active IP Right Cessation
-
2003
- 2003-04-24 US US10/421,888 patent/US20030229249A1/en not_active Abandoned
-
2007
- 2007-06-04 US US11/757,769 patent/US7544834B2/en not_active Expired - Fee Related
- 2007-08-28 CY CY20071101136T patent/CY1106839T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2002034713A1 (ja) | 2004-03-04 |
| CY1106839T1 (el) | 2012-05-23 |
| EP1334964B1 (en) | 2007-08-15 |
| RU2275354C2 (ru) | 2006-04-27 |
| US7544834B2 (en) | 2009-06-09 |
| ATE370115T1 (de) | 2007-09-15 |
| DK1334964T3 (da) | 2007-09-24 |
| US20030229249A1 (en) | 2003-12-11 |
| EP1334964A1 (en) | 2003-08-13 |
| ES2288997T3 (es) | 2008-02-01 |
| CN100422143C (zh) | 2008-10-01 |
| MXPA03003575A (es) | 2003-07-14 |
| US20070232829A1 (en) | 2007-10-04 |
| CA2426745C (en) | 2009-09-15 |
| KR20030059212A (ko) | 2003-07-07 |
| BR0114846A (pt) | 2004-02-25 |
| JP4225057B2 (ja) | 2009-02-18 |
| CN1483018A (zh) | 2004-03-17 |
| WO2002034713A1 (en) | 2002-05-02 |
| CA2426745A1 (en) | 2003-04-23 |
| AU2001296001A1 (en) | 2002-05-06 |
| PT1334964E (pt) | 2007-09-20 |
| DE60130014D1 (de) | 2007-09-27 |
| DE60130014T2 (de) | 2008-05-08 |
| EP1334964A4 (en) | 2005-09-28 |
| KR100810930B1 (ko) | 2008-03-10 |
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