CA2485430C - Process for the preparation of a hydrate of an anthranilic acid derivative - Google Patents
Process for the preparation of a hydrate of an anthranilic acid derivative Download PDFInfo
- Publication number
- CA2485430C CA2485430C CA2485430A CA2485430A CA2485430C CA 2485430 C CA2485430 C CA 2485430C CA 2485430 A CA2485430 A CA 2485430A CA 2485430 A CA2485430 A CA 2485430A CA 2485430 C CA2485430 C CA 2485430C
- Authority
- CA
- Canada
- Prior art keywords
- hydrate
- acid
- dihydro
- dimethoxy
- pharmaceutically acceptable
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 44
- 230000008569 process Effects 0.000 title claims abstract description 30
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 title description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 31
- 239000000706 filtrate Substances 0.000 claims abstract description 14
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000010792 warming Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 56
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 38
- -1 methylenedioxy substituent Chemical group 0.000 claims description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
- 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 claims description 24
- 101001017818 Homo sapiens ATP-dependent translocase ABCB1 Proteins 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000004687 hexahydrates Chemical class 0.000 claims description 12
- 230000036457 multidrug resistance Effects 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 239000012296 anti-solvent Substances 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 230000001717 pathogenic effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000003389 potentiating effect Effects 0.000 claims description 4
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- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000004060 metabolic process Effects 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- HTMGQIXFZMZZKD-UHFFFAOYSA-N 5,6,7,8-tetrahydroisoquinoline Chemical compound N1=CC=C2CCCCC2=C1 HTMGQIXFZMZZKD-UHFFFAOYSA-N 0.000 claims description 2
- YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 claims description 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 230000035515 penetration Effects 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910009112 xH2O Inorganic materials 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 108091006086 inhibitor proteins Proteins 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 abstract description 9
- 238000003860 storage Methods 0.000 abstract description 6
- 238000002425 crystallisation Methods 0.000 abstract description 5
- 238000004090 dissolution Methods 0.000 abstract description 4
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- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 150000004682 monohydrates Chemical class 0.000 description 5
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- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
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- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 4
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
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- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 3
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- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
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| US60/379,759 | 2002-05-14 | ||
| PCT/GB2003/002060 WO2003095447A1 (en) | 2002-05-14 | 2003-05-13 | Process for the preparation of a hydrate of an anthranilic acid derivative |
Publications (2)
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| CA2485430A1 CA2485430A1 (en) | 2003-11-20 |
| CA2485430C true CA2485430C (en) | 2011-12-06 |
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| CA2485430A Expired - Fee Related CA2485430C (en) | 2002-05-14 | 2003-05-13 | Process for the preparation of a hydrate of an anthranilic acid derivative |
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| US (1) | US7524861B2 (https=) |
| EP (1) | EP1506188B1 (https=) |
| JP (1) | JP4464814B2 (https=) |
| KR (1) | KR101060971B1 (https=) |
| CN (1) | CN100349888C (https=) |
| AT (1) | ATE423778T1 (https=) |
| AU (1) | AU2003233899B2 (https=) |
| BR (1) | BR0309990A (https=) |
| CA (1) | CA2485430C (https=) |
| DE (1) | DE60326341D1 (https=) |
| WO (1) | WO2003095447A1 (https=) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100557093B1 (ko) | 2003-10-07 | 2006-03-03 | 한미약품 주식회사 | 다약제 내성 저해 활성을 갖는 테트라졸 유도체 및 그의제조방법 |
| RS56037B1 (sr) | 2004-06-24 | 2017-09-29 | Vertex Pharma | Modulatori atp-vezujućih kasetnih transportera |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| FR2873585B1 (fr) * | 2004-07-27 | 2006-11-17 | Aventis Pharma Sa | Nouvelles formulations galeniques de principes actifs |
| EP1979367A2 (en) * | 2005-12-24 | 2008-10-15 | Vertex Pharmaceuticals Incorporated | Quinolin-4-one derivatives as modulators of abc transporters |
| EP3219705B1 (en) | 2005-12-28 | 2020-03-11 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of the amorphous form of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| GB0706072D0 (en) | 2007-03-28 | 2007-05-09 | Sterix Ltd | Compound |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| PL2408750T3 (pl) | 2009-03-20 | 2016-02-29 | Vertex Pharma | Sposób otrzymywania modulatorów błonowego regulatora przewodnictwa swoistego dla mukowiscydozy |
| US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| JP2015511583A (ja) | 2012-02-27 | 2015-04-20 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | 薬学的組成物およびその投与 |
| CA2919522C (en) | 2013-07-30 | 2019-02-26 | Gilead Connecticut, Inc. | Formulation of syk inhibitors |
| EA029281B1 (ru) | 2013-07-30 | 2018-03-30 | Джилид Коннектикут, Инк. | Полиморф ингибиторов syk |
| TWI662037B (zh) | 2013-12-23 | 2019-06-11 | 美商基利科學股份有限公司 | 脾酪胺酸激酶抑制劑 |
| CN103804352B (zh) * | 2014-01-23 | 2017-06-13 | 中国药科大学 | 三氮唑苯乙基四氢异喹啉类化合物及其制备方法和应用 |
| CN107250113B (zh) | 2014-10-07 | 2019-03-29 | 弗特克斯药品有限公司 | 囊性纤维化跨膜传导调节蛋白的调节剂的共晶 |
| CN104327046B (zh) * | 2014-10-14 | 2017-11-17 | 中国药科大学 | 三氮唑‑n‑乙基四氢异喹啉类化合物及其制备方法和应用 |
| CN104434947B (zh) * | 2014-11-07 | 2016-11-09 | 滨州医学院附属医院 | 一种抗胆管癌的药物组合物及其应用 |
| EP3378858A1 (en) * | 2017-03-21 | 2018-09-26 | Bioprojet | Tetrahydrate of h3 ligand, its process of preparation and pharmaceutical compositions comprising the same |
| CA3073871A1 (en) | 2017-08-25 | 2019-02-28 | Gilead Sciences, Inc. | Polymorphs of syk inhibitors |
| CN113950479A (zh) | 2019-02-22 | 2022-01-18 | 克洛诺斯生物股份有限公司 | 作为syk抑制剂的缩合吡嗪的固体形式 |
| WO2022076662A1 (en) * | 2020-10-07 | 2022-04-14 | Athenex, Inc. | Acetamido-phenylbenzamide derivatives and methods of using the same |
| CN112724124A (zh) * | 2021-01-18 | 2021-04-30 | 林剑雄 | 4-羟基喹啉类衍生物及其制备方法和在抗肿瘤药物中的应用 |
| CN117304105A (zh) * | 2023-08-18 | 2023-12-29 | 中国科学院基础医学与肿瘤研究所(筹) | 一种靶向抑制ABCB1(P-gp)的化合物及制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK280864B6 (en) * | 1991-01-11 | 2000-08-14 | Laboratoires Glaxo Sa | Acridine derivatives, process for their preparation, and pharmaceutical compositions based thereon |
| GB9717576D0 (en) | 1997-08-19 | 1997-10-22 | Xenova Ltd | Pharmaceutical compounds |
| HUP0001531A3 (en) * | 1996-10-18 | 2000-09-28 | Xenova Ltd Slough | Anthranilic acid derivatives as multi drug resistance modulators |
-
2003
- 2003-05-13 US US10/513,986 patent/US7524861B2/en not_active Expired - Fee Related
- 2003-05-13 BR BR0309990-3A patent/BR0309990A/pt not_active IP Right Cessation
- 2003-05-13 AT AT03727661T patent/ATE423778T1/de not_active IP Right Cessation
- 2003-05-13 CN CNB038159295A patent/CN100349888C/zh not_active Expired - Fee Related
- 2003-05-13 KR KR1020047018344A patent/KR101060971B1/ko not_active Expired - Fee Related
- 2003-05-13 JP JP2004503463A patent/JP4464814B2/ja not_active Expired - Fee Related
- 2003-05-13 EP EP03727661A patent/EP1506188B1/en not_active Expired - Lifetime
- 2003-05-13 AU AU2003233899A patent/AU2003233899B2/en not_active Ceased
- 2003-05-13 DE DE60326341T patent/DE60326341D1/de not_active Expired - Lifetime
- 2003-05-13 WO PCT/GB2003/002060 patent/WO2003095447A1/en not_active Ceased
- 2003-05-13 CA CA2485430A patent/CA2485430C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003095447A1 (en) | 2003-11-20 |
| US20050222199A1 (en) | 2005-10-06 |
| EP1506188A1 (en) | 2005-02-16 |
| US7524861B2 (en) | 2009-04-28 |
| AU2003233899B2 (en) | 2009-03-12 |
| JP4464814B2 (ja) | 2010-05-19 |
| CN1665806A (zh) | 2005-09-07 |
| DE60326341D1 (de) | 2009-04-09 |
| EP1506188B1 (en) | 2009-02-25 |
| JP2005538051A (ja) | 2005-12-15 |
| AU2003233899A1 (en) | 2003-11-11 |
| KR20050009706A (ko) | 2005-01-25 |
| KR101060971B1 (ko) | 2011-09-01 |
| BR0309990A (pt) | 2005-02-22 |
| CA2485430A1 (en) | 2003-11-20 |
| CN100349888C (zh) | 2007-11-21 |
| ATE423778T1 (de) | 2009-03-15 |
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