AR046228A1 - Derivados de indol como activadores ppar, un metodo para su preparacion, composiciones farmaceuticas que los contienen y su empleo en la fabricacion de medicamentos. - Google Patents
Derivados de indol como activadores ppar, un metodo para su preparacion, composiciones farmaceuticas que los contienen y su empleo en la fabricacion de medicamentos.Info
- Publication number
- AR046228A1 AR046228A1 ARP040104044A ARP040104044A AR046228A1 AR 046228 A1 AR046228 A1 AR 046228A1 AR P040104044 A ARP040104044 A AR P040104044A AR P040104044 A ARP040104044 A AR P040104044A AR 046228 A1 AR046228 A1 AR 046228A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- hydrogen
- formula
- cycloalkyl
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title 1
- 239000012190 activator Substances 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 25
- 229910052739 hydrogen Inorganic materials 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 8
- 150000002431 hydrogen Chemical class 0.000 abstract 7
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
- 101150014691 PPARA gene Proteins 0.000 abstract 1
- 239000000556 agonist Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Manufacturing & Machinery (AREA)
- Ceramic Engineering (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Inorganic Chemistry (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Composiciones farmacéuticas que contienen dichos compuestos, a un proceso para su obtención y a la utilización de los mismos para el tratamiento y/o prevención de enfermedades moduladas por agonistas de PPARd y/o PPARa. Reivindicación 1: Compuestos de fórmula (1), en la que: R1 es hidrógeno o alquilo C1-7; R2 y R3 independientemente uno de otro son hidrógeno o alquilo C1-7; R4 y R5 independientemente uno de otro son hidrógeno, alquilo C1-7, cicloalquilo C3-7, halógeno, (alcoxi C1-7)-alquilo C1- 7, alquenilo C2-7, alquinilo C2-7 o fluoralquilo C1-7; R4' y R5' juntos forman un doble enlace, o bien R4' y R5' son hidrógeno; R6, R7, R8 y R9 independientemente uno de otro son hidrógeno, alquilo C1-7, cicloalquilo C3-7, halógeno, (alcoxi C1-7)- alquilo C1-7, alquenilo C2-7, alquinilo C2-7, fluoralquilo C1-7, cianoalquilo C1-7 o ciano; y uno de R6, R7 y R8 es un grupo de fórmula (2), en la que X es S, O ó NR10; R10 es hidrógeno, alquilo C1-7, cicloalquilo C3-7 o fluoralquilo C1-7; R11 y R12 independientemente uno de otro son hidrógeno, alquilo C1-7, cicloalquilo C3-7, fluoralquilo C1-7 o flúor; Y1, Y2 Y3 e Y4 son N o C-R13 y 1 ó 2 de Y1, Y2, Y3 e Y4 son N y los demás son C-R13; R13 con independencia de su aparición se selecciona entre hidrógeno, alquilo C1-7, cicloalquilo C3-7, (cicloalquil C3-7)-alquilo C1-7, fluoralquilo C1-7, (alcoxi C1-7)-alquilo C1-7, hidroxialquilo C1-7, (alquiltio C1-7)-alquilo C1-7, carboxi-(alcoxi C1-7)-alquilo C1-7, carboxi, carboxi-alquilo C1-7, mono- o di(alquil C1-7)-amino-alquilo C1-7, (alcanoil C1-7)-alquilo C1-7, alquenilo C2-7 y alquinilo C2-7; R14 es arilo o heteroarilo; n es 0, 1 ó 2; y las sales farmacéuticamente aceptables y/o ésteres de los mismos. Reivindicación 24: Un proceso para la obtención de los compuestos según cualquiera de las reivindicaciones 1 a 23, dicho proceso consiste en: a) la reacción de un compuesto de fórmula (3), en la que de R4 a R9 tienen los significados definidos en la reivindicación 1, con un compuesto de fórmula (4), en la que R1 es alquilo C1-7, R2 y R3 tienen los significados definidos en la reivindicación 1 y R15 es halógeno, triflato u otro grupo saliente, para obtener un compuesto de fórmula (1), en la que R1 es alquilo C1-7 y de R2 a R9 tienen los significados definidos en la reivindicación 1, y opcionalmente por hidrólisis del grupo éster para obtener un compuesto de fórmula (1), en la que R1 es hidrógeno; o, como alternativa, b) la reacción de un compuesto equivalente al de la fórmula (1), en la que R1 es alquilo C1-7, de R2 a R5' tienen los significados definidos en la reivindicación 1 y R6, R7, R8 y R9 se seleccionan independientemente uno de otro entre hidrógeno, alquilo C1-7, cicloalquilo C3-7, halógeno, (alcoxi C1-7)- alquilo C1-7, alquenilo C2-7, alquinilo C2-7, fluoralquilo C1-7, ciano-alquilo C1-7 y ciano, y uno de R6, R7 o R8 es -OH, -SH o -NHR10, siendo R10 hidrógeno, alquilo C1-7, cicloalquilo C3-7 o fluoralquilo -C1-7, con un compuesto de fórmula (5), en la que: Y1, Y2, Y3, Y4, R11, R12, R14 y n tienen los significados definidos en la reivindicación 1 y R16 es -OH, -Cl, -Br, -I u otro grupo saliente, para obtener un compuesto de fórmula (1), en la que R1 es alquilo C1-7 y de R2 a R9 tienen los significados definidos en la reivindicación 1, y opcionalmente la hidrólisis del grupo éster para obtener un compuesto de fórmula (1), en la que R1 es hidrógeno.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03104083 | 2003-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR046228A1 true AR046228A1 (es) | 2005-11-30 |
Family
ID=34530792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040104044A AR046228A1 (es) | 2003-11-05 | 2004-11-03 | Derivados de indol como activadores ppar, un metodo para su preparacion, composiciones farmaceuticas que los contienen y su empleo en la fabricacion de medicamentos. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6995263B2 (es) |
| EP (1) | EP1682535A1 (es) |
| JP (1) | JP2007509996A (es) |
| KR (1) | KR100761615B1 (es) |
| CN (1) | CN100509802C (es) |
| AR (1) | AR046228A1 (es) |
| AU (1) | AU2004291259A1 (es) |
| BR (1) | BRPI0416238A (es) |
| CA (1) | CA2543239A1 (es) |
| MX (1) | MXPA06004642A (es) |
| RU (1) | RU2367659C2 (es) |
| TW (1) | TW200530223A (es) |
| WO (1) | WO2005049606A1 (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2530452C (en) * | 2003-07-02 | 2011-07-26 | F. Hoffmann-La Roche Ag | Indolyl derivatives substituted with a thiazole ring and their use as ppar modulators |
| TW200608976A (en) | 2004-05-08 | 2006-03-16 | Neurogen Corp | 4,5-disubstituted-2-aryl pyrimidines |
| US7405236B2 (en) * | 2004-08-16 | 2008-07-29 | Hoffman-La Roche Inc. | Indole derivatives comprising an acetylene group |
| CN101166725A (zh) * | 2005-02-25 | 2008-04-23 | 武田药品工业株式会社 | 吡啶基乙酸化合物 |
| US7897763B2 (en) | 2005-12-29 | 2011-03-01 | Lexicon Pharmaceuticals, Inc. | Process for the preparation of substituted phenylalanines |
| CN103265495B (zh) * | 2005-12-29 | 2016-11-16 | 莱西肯医药有限公司 | 多环氨基酸衍生物及其使用方法 |
| US7855291B2 (en) | 2005-12-29 | 2010-12-21 | Lexicon Pharmaceuticals, Inc. | Process for the preparation of substituted phenylalanines |
| US20080202239A1 (en) * | 2007-02-28 | 2008-08-28 | Fazzio R Shane | Piezoelectric acceleration sensor |
| EP2529740A1 (en) * | 2007-08-24 | 2012-12-05 | Lexicon Pharmaceuticals, Inc. | Methods of preparing 4-Phenyl-6(2,2,2-Trifluoro-1-Phenylethoxy) Pyrimidine-based compounds. |
| DE102007042754A1 (de) | 2007-09-07 | 2009-03-12 | Bayer Healthcare Ag | Substituierte 6-Phenylnikotinsäuren und ihre Verwendung |
| DE102007061757A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | Substituierte 2-Phenylpyrimidin-5-carbonsäuren und ihre Verwendung |
| US7750027B2 (en) | 2008-01-18 | 2010-07-06 | Oxagen Limited | Compounds having CRTH2 antagonist activity |
| CN103044310B (zh) * | 2013-01-18 | 2015-02-04 | 贵阳医学院 | 二氢吲哚-3-乙酸衍生物、其制备方法以及在药物中的应用 |
| GB201407807D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| GB201407820D0 (en) | 2014-05-02 | 2014-06-18 | Atopix Therapeutics Ltd | Polymorphic form |
| CN106310173A (zh) * | 2016-08-24 | 2017-01-11 | 厦门三川利生物科技有限公司 | 含过氧化物酶体增殖物激活受体多维果酸醇及其制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2163150B (en) * | 1984-07-19 | 1988-05-25 | Sandoz Ltd | 3-aminopropoxyaryl derivatives |
| CA2305808A1 (en) * | 1997-10-02 | 1999-04-15 | Sankyo Company Limited | Amidocarboxylic acid derivatives |
| US6369067B1 (en) * | 1997-10-27 | 2002-04-09 | Dr. Reddy's Research Foundation | Monocyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them |
| AU2001277056B2 (en) * | 2000-07-25 | 2005-09-29 | Merck & Co., Inc. | N-substituted indoles useful in the treatment of diabetes |
| EA200400011A1 (ru) * | 2001-06-07 | 2004-06-24 | Эли Лилли Энд Компани | Модуляторы рецепторов, активируемых пролифераторами пероксисом (prar) |
| EE200400075A (et) * | 2001-08-29 | 2004-08-16 | Warner-Lambert Company Llc | Peroraalsed antidiabeetilised ained |
| TWI231757B (en) | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| EP1432679A1 (en) | 2001-09-24 | 2004-06-30 | Bayer Pharmaceuticals Corporation | Preparation and use of pyrrole derivatives for treating obesity |
| PE20030547A1 (es) | 2001-09-24 | 2003-08-18 | Bayer Corp | Derivados de imidazol para el tratamiento de la obesidad |
| US6867224B2 (en) * | 2002-03-07 | 2005-03-15 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods of preparation |
| US6875780B2 (en) * | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
| US7528160B2 (en) * | 2003-01-06 | 2009-05-05 | Eli Lilly And Company | Fused heterocyclic derivatives as PPAR modulators |
| BRPI0407180A (pt) * | 2003-02-14 | 2006-02-07 | Lilly Co Eli | Composto, composição farmacêutica, métodos para modular um receptor ativado pelo proliferador de peroxissoma, para tratar ou prevenir uma doença ou condição, para diminuir a glicose no sangue em um mamìfero, para tratar ou prevenir diabetes mellitus, doença cardiovascular e sìndrome x em um mamìfero, e, uso de um composto |
| US7244763B2 (en) * | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
-
2004
- 2004-10-28 JP JP2006538705A patent/JP2007509996A/ja active Pending
- 2004-10-28 RU RU2006119503/04A patent/RU2367659C2/ru not_active IP Right Cessation
- 2004-10-28 WO PCT/EP2004/012197 patent/WO2005049606A1/en not_active Ceased
- 2004-10-28 CN CNB2004800328716A patent/CN100509802C/zh not_active Expired - Fee Related
- 2004-10-28 MX MXPA06004642A patent/MXPA06004642A/es active IP Right Grant
- 2004-10-28 AU AU2004291259A patent/AU2004291259A1/en not_active Abandoned
- 2004-10-28 CA CA002543239A patent/CA2543239A1/en not_active Abandoned
- 2004-10-28 KR KR1020067008796A patent/KR100761615B1/ko not_active Expired - Fee Related
- 2004-10-28 BR BRPI0416238-2A patent/BRPI0416238A/pt not_active IP Right Cessation
- 2004-10-28 EP EP04790967A patent/EP1682535A1/en not_active Withdrawn
- 2004-10-29 US US10/978,144 patent/US6995263B2/en not_active Expired - Fee Related
- 2004-11-03 AR ARP040104044A patent/AR046228A1/es unknown
- 2004-11-04 TW TW093133672A patent/TW200530223A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA06004642A (es) | 2006-06-27 |
| EP1682535A1 (en) | 2006-07-26 |
| KR100761615B1 (ko) | 2007-10-04 |
| US6995263B2 (en) | 2006-02-07 |
| KR20060086384A (ko) | 2006-07-31 |
| CN1878768A (zh) | 2006-12-13 |
| TW200530223A (en) | 2005-09-16 |
| WO2005049606A1 (en) | 2005-06-02 |
| BRPI0416238A (pt) | 2007-01-02 |
| CA2543239A1 (en) | 2005-06-02 |
| AU2004291259A1 (en) | 2005-06-02 |
| JP2007509996A (ja) | 2007-04-19 |
| RU2367659C2 (ru) | 2009-09-20 |
| US20050096353A1 (en) | 2005-05-05 |
| RU2006119503A (ru) | 2007-12-27 |
| CN100509802C (zh) | 2009-07-08 |
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