AR103508A2 - PROCESO PARA LA PREPARACIÓN DE OXI-(1H)-QUINOLIN-2-ONAS 5-(a-HALOACETILO)-8-SUSTITUIDAS - Google Patents
PROCESO PARA LA PREPARACIÓN DE OXI-(1H)-QUINOLIN-2-ONAS 5-(a-HALOACETILO)-8-SUSTITUIDASInfo
- Publication number
- AR103508A2 AR103508A2 ARP160100188A ARP160100188A AR103508A2 AR 103508 A2 AR103508 A2 AR 103508A2 AR P160100188 A ARP160100188 A AR P160100188A AR P160100188 A ARP160100188 A AR P160100188A AR 103508 A2 AR103508 A2 AR 103508A2
- Authority
- AR
- Argentina
- Prior art keywords
- quinolin
- hydroxy
- acetyl
- oxy
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- PJVZAXRWCFBQFH-UHFFFAOYSA-N 5-acetyl-8-hydroxy-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2C(=O)C PJVZAXRWCFBQFH-UHFFFAOYSA-N 0.000 abstract 10
- 239000002904 solvent Substances 0.000 abstract 10
- 239000003795 chemical substances by application Substances 0.000 abstract 9
- UTMRKCQYCLEKDL-UHFFFAOYSA-N (2-oxo-1h-quinolin-8-yl) acetate Chemical compound C1=CC(=O)NC2=C1C=CC=C2OC(=O)C UTMRKCQYCLEKDL-UHFFFAOYSA-N 0.000 abstract 7
- 239000002841 Lewis acid Substances 0.000 abstract 7
- 150000007517 lewis acids Chemical class 0.000 abstract 7
- ZXZKYYHTWHJHFT-UHFFFAOYSA-N quinoline-2,8-diol Chemical compound C1=CC(=O)NC2=C1C=CC=C2O ZXZKYYHTWHJHFT-UHFFFAOYSA-N 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 6
- 125000006239 protecting group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 5-acetyl-8-substituted oxy- (1 H) -quinolin-2-one Chemical class 0.000 abstract 3
- 150000001450 anions Chemical class 0.000 abstract 3
- 230000002140 halogenating effect Effects 0.000 abstract 3
- 238000011065 in-situ storage Methods 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- KGVIJLMNQNSQHB-UHFFFAOYSA-N 5,6-diethyl-2,3-dihydro-1h-inden-2-amine Chemical compound C1=C(CC)C(CC)=CC2=C1CC(N)C2 KGVIJLMNQNSQHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- QZZUEBNBZAPZLX-QFIPXVFZSA-N indacaterol Chemical compound N1C(=O)C=CC2=C1C(O)=CC=C2[C@@H](O)CNC1CC(C=C(C(=C2)CC)CC)=C2C1 QZZUEBNBZAPZLX-QFIPXVFZSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pulmonology (AREA)
- Materials Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Quinoline Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
La presente solicitud se refiere un procedimiento para preparar oxi-(1H)-quinolin-2-onas 5-(a-haloacetil)-8-substituidas. El procedimiento involucra, (i) hacer reaccionar, (a) 8-hidroxi-(1H)-quinolin-2-ona con un agente de acilación y un ácido Lewis para formar 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; o (b) 8-hidroxi-(1H)-quinolin-2-ona con un agente de acilación para formar 8-acetoxi-(1H)-quinolin-2-ona, y tratar, in situ, la 8-acetoxi-(1H)-quinolin-2-ona con un ácido Lewis para formar la 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; o (c) 8-acetoxi-(1H)-quinolin-2-ona con ácido Lewis para formar 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; (ii) hacer reaccionar la 5-acetil-8-hidroxi-(1H)-quinolin-2-ona preparada en el paso (i) con un compuesto que tiene la fórmula RL en presencia de una base y un solvente para formar oxi-(1H)-quinolin-2-ona 5-acetil-8-substituida, en donde R es un grupo protector y L es un grupo saliente; y (iii) hacer reaccionar la oxi-(1H)-quinolin-2-ona 5-acetil-8-substituida con un agente de halogenación en presencia de un solvente para formar oxi-(1H)-quinolin-2-ona 5-(a-haloacetil)-8-substituida. Reivindicación 1: Un proceso para la preparación de oxi-(1H)-quinolin-2-onas 5-(a-haloacetilo)-8-sustituidas y caracterizado porque comprende: (a) hacer reaccionar (i) 8-hidroxi-(1H)-quinolin-2-ona con un agente de acilación y un ácido Lewis para formar 5-acetil-8-hidroxi-(1H)quinolin-2-ona; o (ii) 8-hidroxi-(1H)-quinolin-2-ona con un agente de acilación para formar 8-acetoxi-(1H)-quinolin-2-ona, y tratar, in-situ, la 8-acetoxi-(1H)-quinolin-2-ona con un ácido Lewis para formar 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; (b) hacer reaccionar la 5-acetil-8-hidroxi-(1H)-quinolin-2-ona preparada en la Etapa (a) con un compuesto que tiene la fórmula RL en la presencia de una base y un disolvente para formar 5-acetil-8-sustituido oxi-(1H)-quinolin-2-ona, en donde R es un grupo protector y L es un grupo saliente; y (c) hacer reaccionar la 5-acetil-8-sustituida oxi-(1H)-quinolin-2-ona con un agente de halogenación en presencia de un disolvente para formar una 5-(a-haloacetilo)-8-sustituido oxi-(1H)-quinolin-2-ona. Reivindicación 14: Un proceso para la preparación de sales de 5-[(R)-(5,6-2-dietil-indan-2-ilamino)-1-hidroxi-etil]-8-hidroxi-(1H)-quinolinona-2-ona que comprende: (a) hacer reaccionar (i) 8-hidroxi-(1H)-quinolin-2-ona con un agente de acilación y un ácido Lewis para formar 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; o (ii) 8-hidroxi-(1H)-quinolin-2-ona con un agente de acilación para formar 8-acetoxi-(1H)-quinolin-2-ona, y tratar, in-situ, la 8-acetoxi-(1H)quinolin-2-ona con un ácido Lewis para formar 5-acetil-8-hidroxi-(1H)-quinolin-2-ona; o (b) hacer reaccionar la 5-acetil-8-hidroxi-(1H)-quinolin-2-ona preparada en la Etapa (i) con un compuesto que tiene la fórmula RL en la presencia de una base y un disolvente para formar 5-acetil-8-sustituido oxi-(1H)-quinolin-2-ona, en donde R es un grupo protector y L es un grupo saliente; (c) hacer reaccionar la 5-acetil-8-sustituida oxi-(1H)-quinolin-2-ona con un agente de halogenación en presencia de un disolvente para formar un anillo de 5-(a-haloacetilo)-8-sustituido oxi-(1H)-quinolin-2-ona; (d) hacer reaccionar un 5-(a-haloacetilo)-8-sustituido oxi-(1H)-quinolin-2-ona con un agente reductor en presencia de un catalizador quiral para formar 8-(oxi sustituida)-5-((R)-2-halo-1-hidroxi-etil)-(1H)-quinolin-2-ona; e) tratar la 8-(oxi sustituido)-5-((R)-2-halo-1-hidroxi-etil)-(1H)-quinolin-2-ona con una base en presencia de un disolvente para formar 8-(oxi sustituida)-5-(R)-oxiranil-(1H)-quinolin-2-ona; (f) hacer reaccionar la 8-oxi sustituido-5-(R)-oxiranil-(1H)-quinolin-2-ona que tiene la fórmula (1) con 2-amino-(5,6-dietil)-indano para formar una mezcla de reacción que contiene compuestos que tienen las fórmulas (2), (3) y (4) en la que R es un grupo protector; (g) tratar la mezcla de reacción preparada en el paso (f) con un ácido en presencia de un disolvente para formar una sal correspondiente; (h) aislar y cristalizar una sal que tiene la fórmula (5) en la que R es un grupo protector y A⁻ es un anión; (i) eliminar el grupo protector de la sal que tiene la fórmula (5) en presencia de un disolvente para formar una sal que tiene la fórmula (6) en la que A⁻ es un anión; (j) tratar la sal que tiene la fórmula (6) con un ácido en presencia de un disolvente para formar 5-[(R)-2-(5,6-dietil-indan-2-ilamino)-1-hidroxi-etil]-8-hidroxi-(1H)-quinolin-2-ona que tiene la fórmula (7) en la que X⁻ es un anión.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45972403P | 2003-04-02 | 2003-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR103508A2 true AR103508A2 (es) | 2017-05-17 |
Family
ID=33131902
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040101105A AR043825A1 (es) | 2003-04-02 | 2004-04-01 | Procesos de preparacion de 5-(haloacetil)-8-(oxisustituidos)-(1h)-quinolin-2-onas |
| ARP160100188A AR103508A2 (es) | 2003-04-02 | 2016-01-25 | PROCESO PARA LA PREPARACIÓN DE OXI-(1H)-QUINOLIN-2-ONAS 5-(a-HALOACETILO)-8-SUSTITUIDAS |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040101105A AR043825A1 (es) | 2003-04-02 | 2004-04-01 | Procesos de preparacion de 5-(haloacetil)-8-(oxisustituidos)-(1h)-quinolin-2-onas |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US7605267B2 (es) |
| EP (1) | EP1613599B8 (es) |
| JP (1) | JP4726778B2 (es) |
| KR (1) | KR101073740B1 (es) |
| CN (1) | CN1774423A (es) |
| AR (2) | AR043825A1 (es) |
| AT (1) | ATE491690T1 (es) |
| AU (1) | AU2004226212B2 (es) |
| BR (1) | BRPI0409154B1 (es) |
| CA (1) | CA2520990C (es) |
| CL (1) | CL2004000706A1 (es) |
| CO (1) | CO5700779A2 (es) |
| CY (1) | CY1111515T1 (es) |
| DE (1) | DE602004030553D1 (es) |
| DK (1) | DK1613599T3 (es) |
| EC (1) | ECSP056059A (es) |
| ES (1) | ES2358193T3 (es) |
| HR (1) | HRP20110184T1 (es) |
| IL (1) | IL171053A (es) |
| IS (1) | IS2800B (es) |
| MA (1) | MA27761A1 (es) |
| MX (1) | MXPA05010616A (es) |
| MY (1) | MY141871A (es) |
| NO (1) | NO331980B1 (es) |
| NZ (1) | NZ542623A (es) |
| PE (2) | PE20100399A1 (es) |
| PL (1) | PL1613599T3 (es) |
| PT (1) | PT1613599E (es) |
| RU (1) | RU2339621C2 (es) |
| SI (1) | SI1613599T1 (es) |
| TN (1) | TNSN05245A1 (es) |
| TW (1) | TWI324151B (es) |
| WO (1) | WO2004087668A1 (es) |
| ZA (1) | ZA200507603B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| GB0413960D0 (en) * | 2004-06-22 | 2004-07-28 | Novartis Ag | Organic compounds |
| NZ573292A (en) | 2006-06-30 | 2011-03-31 | Novartis Ag | Quinolinone derivatives and their pharmaceutical compositions |
| WO2013132514A2 (en) * | 2012-03-09 | 2013-09-12 | Rao Davuluri Ramamohan | A novel process for the preparation of (r)-5-[2-[(5, 6-diethyl-2, 3-dihydro-1h-inden-2-yl) amino]-1-hydroxyethyl]-8-hydroxy quinolin-2(1h)-one |
| CN102633717B (zh) * | 2012-03-30 | 2013-11-20 | 西南大学 | N-乙酰-喹啉-2(1h)酮类化合物及其制备方法和应用 |
| CN104379566B (zh) * | 2012-07-11 | 2016-08-24 | 上海威智医药科技有限公司 | 茚达特罗中间体及茚达特罗的合成方法 |
| CZ306252B6 (cs) | 2013-03-15 | 2016-10-26 | Zentiva, K.S. | Způsob přípravy 5-[(R)-2-(5,6-diethylindan-2-ylamino)-1-hydroxyethyl]-8-hydroxy-(1H)-chinolin-2-onu (indacaterolu) |
| US9682935B2 (en) | 2014-01-09 | 2017-06-20 | Davuluri Ramamohan Rao | Process for preparation of indacaterol or its pharmaceutically acceptable salts |
| CN105693603B (zh) * | 2014-11-24 | 2019-11-29 | 上海医药工业研究院 | 改良的马来酸茚达特罗制备工艺 |
| WO2016161956A1 (zh) * | 2015-04-09 | 2016-10-13 | 正大天晴药业集团股份有限公司 | 茚达特罗或其盐的制备方法 |
| CN107868045A (zh) * | 2016-09-28 | 2018-04-03 | 四川海思科制药有限公司 | 一种茚达特罗中间体的制备方法 |
| CN108264483A (zh) * | 2016-12-31 | 2018-07-10 | 天津金耀集团有限公司 | 一种马来酸茚达特罗的制备方法 |
| CN109721534B (zh) * | 2018-09-25 | 2022-05-20 | 四川海思科制药有限公司 | 一种马来酸茚达特罗中间体及其制备方法和用途 |
| CN114751857A (zh) * | 2022-04-29 | 2022-07-15 | 梯尔希（南京）药物研发有限公司 | 一种茚达特罗杂质的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS539228B2 (es) * | 1974-01-31 | 1978-04-04 | ||
| CA1164459A (en) | 1980-11-11 | 1984-03-27 | Yung-Hsiung Yang | Process for preparing (imidazo¬1,2-a|pyridine- 2-yl)-carbostyril or -3,4-dihydrocarbostyryl derivatives |
| JPS5896022A (ja) * | 1981-11-30 | 1983-06-07 | Otsuka Pharmaceut Co Ltd | 強心剤 |
| ES8403457A1 (es) * | 1983-01-28 | 1984-03-16 | Espanola Farma Therapeut | Procedimiento para la obtencion de un compuesto derivado de la 2-quinolinona. |
| ES8605239A1 (es) | 1985-12-04 | 1986-03-16 | Astur Pharma | Un procedimiento para la preparacion de quinolonas sustitui-das |
| US4894219A (en) * | 1988-03-29 | 1990-01-16 | University Of Florida | Beta-agonist carbostyril derivatives, assay method and pharmacological composition |
| GB9405019D0 (en) * | 1994-03-15 | 1994-04-27 | Smithkline Beecham Plc | Novel compounds |
| DE69738949D1 (de) * | 1996-05-20 | 2008-10-09 | Darwin Discovery Ltd | Chinolincarboxamide als tnf-inhibitoren und als pde-iv inhibitoren |
| GB9913083D0 (en) * | 1999-06-04 | 1999-08-04 | Novartis Ag | Organic compounds |
| GB0029562D0 (en) * | 2000-12-04 | 2001-01-17 | Novartis Ag | Organic compounds |
| WO2003042160A1 (en) * | 2001-11-13 | 2003-05-22 | Theravance, Inc. | Aryl aniline beta-2 adrenergic receptor agonists |
| TWI324150B (en) * | 2003-02-28 | 2010-05-01 | Novartis Ag | Process for preparing 5-[(r)-2-(5,6-diethyl-indan-2-ylamino)-1-hydroxy-ethyl]-8-hydroxy-(1h)-quinolin-2-one salt |
-
2004
- 2004-03-31 TW TW093108942A patent/TWI324151B/zh not_active IP Right Cessation
- 2004-03-31 PE PE2010000225A patent/PE20100399A1/es not_active Application Discontinuation
- 2004-03-31 PE PE2004000341A patent/PE20050211A1/es not_active Application Discontinuation
- 2004-04-01 AU AU2004226212A patent/AU2004226212B2/en not_active Expired
- 2004-04-01 ES ES04725035T patent/ES2358193T3/es not_active Expired - Lifetime
- 2004-04-01 WO PCT/EP2004/003479 patent/WO2004087668A1/en not_active Ceased
- 2004-04-01 EP EP04725035A patent/EP1613599B8/en not_active Expired - Lifetime
- 2004-04-01 AT AT04725035T patent/ATE491690T1/de active
- 2004-04-01 JP JP2006504953A patent/JP4726778B2/ja not_active Expired - Lifetime
- 2004-04-01 CA CA2520990A patent/CA2520990C/en not_active Expired - Lifetime
- 2004-04-01 PL PL04725035T patent/PL1613599T3/pl unknown
- 2004-04-01 MY MYPI20041213A patent/MY141871A/en unknown
- 2004-04-01 SI SI200431618T patent/SI1613599T1/sl unknown
- 2004-04-01 HR HR20110184T patent/HRP20110184T1/hr unknown
- 2004-04-01 CL CL200400706A patent/CL2004000706A1/es unknown
- 2004-04-01 BR BRPI0409154-0B1A patent/BRPI0409154B1/pt not_active IP Right Cessation
- 2004-04-01 RU RU2005133664/04A patent/RU2339621C2/ru active
- 2004-04-01 AR ARP040101105A patent/AR043825A1/es not_active Application Discontinuation
- 2004-04-01 DK DK04725035.2T patent/DK1613599T3/da active
- 2004-04-01 NZ NZ542623A patent/NZ542623A/en not_active IP Right Cessation
- 2004-04-01 CN CNA2004800089560A patent/CN1774423A/zh active Pending
- 2004-04-01 DE DE602004030553T patent/DE602004030553D1/de not_active Expired - Lifetime
- 2004-04-01 PT PT04725035T patent/PT1613599E/pt unknown
- 2004-04-01 US US10/550,621 patent/US7605267B2/en active Active
- 2004-04-01 MX MXPA05010616A patent/MXPA05010616A/es active IP Right Grant
-
2005
- 2005-09-20 ZA ZA200507603A patent/ZA200507603B/en unknown
- 2005-09-22 IL IL171053A patent/IL171053A/en active IP Right Grant
- 2005-09-29 EC EC2005006059A patent/ECSP056059A/es unknown
- 2005-09-30 KR KR1020057018750A patent/KR101073740B1/ko not_active Expired - Lifetime
- 2005-09-30 TN TNP2005000245A patent/TNSN05245A1/en unknown
- 2005-10-11 MA MA28545A patent/MA27761A1/fr unknown
- 2005-10-12 CO CO05104250A patent/CO5700779A2/es active IP Right Grant
- 2005-10-27 IS IS8095A patent/IS2800B/is unknown
- 2005-11-01 NO NO20055099A patent/NO331980B1/no unknown
-
2011
- 2011-03-14 CY CY20111100284T patent/CY1111515T1/el unknown
-
2016
- 2016-01-25 AR ARP160100188A patent/AR103508A2/es unknown
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