AR057981A1 - Compuesto de pirroloquinolin -4- ona, su uso para la preparacion de un medicamento, composicion farmaceutica que lo comprende y compuestos intermediarios pra su preparacion - Google Patents
Compuesto de pirroloquinolin -4- ona, su uso para la preparacion de un medicamento, composicion farmaceutica que lo comprende y compuestos intermediarios pra su preparacionInfo
- Publication number
- AR057981A1 AR057981A1 ARP060104571A ARP060104571A AR057981A1 AR 057981 A1 AR057981 A1 AR 057981A1 AR P060104571 A ARP060104571 A AR P060104571A AR P060104571 A ARP060104571 A AR P060104571A AR 057981 A1 AR057981 A1 AR 057981A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- cr4r8
- hydrogen
- aromatic ring
- aromatic
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000006574 non-aromatic ring group Chemical group 0.000 abstract 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 5
- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 abstract 4
- 125000004429 atom Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 101150020251 NR13 gene Proteins 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 125000005647 linker group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- -1 pyrroloquinolin-4-one compound Chemical class 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000005157 alkyl carboxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/436—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Un compuesto de pirroloquinolin-4-ona de formula (1). Uso de dicho compuesto para la fabricacion de un medicamento para tratar infecciones bacterianas. Composicion farmacéutica que lo comprende. Compuestos intermediarios para su preparacion. Reivindicacion 1: Un compuesto de pirroloquinolin-4-ona caracterizado porque es de formula (1) o una de sus sales y/o uno de sus solvatos farmacéuticamente aceptables, en donde, R1a y R1b se seleccionan independientemente de hidrogeno; halogeno; ciano; alquilo C1-6; alquil C1-6tio; trifluorometilo; trifluorometoxi; carboxi; hidroxi opcionalmente sustituido con alquilo C1-6 o alcoxi C1-6 substituido alquilo C1-6; alcoxi C1-6 substituido alquilo C1-6; hidroxialquilo C1-6; un grupo amino opcionalmente N-sustituido con uno o dos grupos alquilo C1-6, formilo, alquil C1-6 carbonilo o alquil C1-6sulfonilo; o aminocarbonilo en donde el grupo amino está opcionalmente sustituido por alquilo C1-4; R2 es hidrogeno o alquilo C1-4, o junto con R6 forma Y segun se define a continuacion; A es un grupo de formula (2) o (3);en el que R3 es segun se define para R1a o R1b o es oxo y n es 1 o 2; o A es un grupo de formula (4); W1, W2 y W3 son CR4R8, o W2 y W3 son CR4R8 y W1 representa un enlace entre W3 y N, X es O, CR4R8, o NR6; un R4 es segun se define para R1a y R1b y los restantes y R8 son hidrogeno o un R4 y R8 son conjuntamente oxo y los restantes son hidrogeno; R6 es hidrogeno o alquilo C1-6; o junto con R2 forma Y; R7 es hidrogeno; halogeno; hidroxi opcionalmente sustituido con alquilo C1-6; o alquilo C1-6; Y es CR4R8CH2; CH2CR4R8; (C=O); CR4R8; CR4R8(C=O); o (C=O)CR4R8; o cuando X es CR4R8, R8 y R7 representan juntos un enlace; U se selecciona de CO, y CH2 y R5 es un sistema de anillo bicíclico, carbocíclico o heterocíclico opcionalmente sustituido de formula (5), que contiene hasta cuatro heteroátomos en cada anillo en el que al menos uno de los anillos (a) y (b) es aromático; X1 es C o N cuando forma parte de un anillo aromático, o CR14 cuando forma parte de un anillo no aromático; X2 es N, NR13, O, S(O)x, CO o CR14 cuando es parte de un anillo aromático o no aromático, o puede ser además CR14R15 cuando es parte de un anillo no aromático; X3 y X5 son independientemente N o C; Y1 es un grupo enlazador de 0 a 4 átomos en el que cada átomo está seleccionado de N, NR13, O, S(O)x, CO y CR14 cuando forma parte de un anillo aromático o no aromático o puede ser adicionalmente CR14R15 cuando forma parte de un anillo no aromático; Y2 es un grupo enlazador de 2 a 6 átomos, en el que cada átomo de Y2 se selecciona independientemente de N, NR13, O, S(O)x, CO, CR14 cuando forma parte de un anillo aromático o no aromático o puede ser adicionalmente CR14R15 cuando forma parte de un anillo no aromático; cada uno de R14 y R15 se selecciona independientemente de: H; alquil C1-4tio; halo; alquil C1-4carboxi; alquilo C1-4; alcoxi C1-4carbonilo; alquil C1-4carbonilo; alcoxi C1-4alquilo C1-4; hidroxi; hidroxialquilo C1-4; alcoxi C1-4; nitro; ciano; carboxi ; amina o aminocarbonilo opcionalmente mono o disustituido por alquilo C1-4; o R14 y R15 pueden representar conjuntamente oxo; cada R13 es independientemente H; trifluorometilo; alquilo C1-4 opcionalmente sustituido por hidroxi, alcoxi C1-6, alquil C1-6tio, halo o trifluorometilo; alquenilo C2-4; alcoxi C1-4carbonilo; alquil C1-4 carbonilo; alquil C1-6sulfonilo; aminocarbonilo en el cual el grupo amino está opcionalmente mono o disustituido por alquilo C1-4; cada x es independientemente 0, 1 o 2; y R9 es hidrogeno o hidroxi.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72897505P | 2005-10-21 | 2005-10-21 | |
| US82659006P | 2006-09-22 | 2006-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR057981A1 true AR057981A1 (es) | 2008-01-09 |
Family
ID=38256822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060104571A AR057981A1 (es) | 2005-10-21 | 2006-10-19 | Compuesto de pirroloquinolin -4- ona, su uso para la preparacion de un medicamento, composicion farmaceutica que lo comprende y compuestos intermediarios pra su preparacion |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US20080280892A1 (es) |
| EP (1) | EP1954697B1 (es) |
| JP (1) | JP2009512695A (es) |
| KR (1) | KR20080064173A (es) |
| AR (1) | AR057981A1 (es) |
| AT (1) | ATE458737T1 (es) |
| AU (1) | AU2006335042A1 (es) |
| BR (1) | BRPI0617467A2 (es) |
| CA (1) | CA2626641A1 (es) |
| CR (1) | CR9930A (es) |
| CY (1) | CY1110137T1 (es) |
| DE (1) | DE602006012535D1 (es) |
| DK (1) | DK1954697T3 (es) |
| EA (1) | EA200801128A1 (es) |
| ES (1) | ES2340531T3 (es) |
| HR (1) | HRP20100194T8 (es) |
| IL (1) | IL190803A0 (es) |
| MA (1) | MA29873B1 (es) |
| NO (1) | NO20082191L (es) |
| NZ (1) | NZ567315A (es) |
| PE (1) | PE20070793A1 (es) |
| PL (1) | PL1954697T3 (es) |
| PT (1) | PT1954697E (es) |
| SI (1) | SI1954697T1 (es) |
| TW (1) | TW200736263A (es) |
| WO (1) | WO2007081597A2 (es) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007081597A2 (en) * | 2005-10-21 | 2007-07-19 | Glaxo Group Limited | Peri condensed tricyclic compounds useful as antibacterial agents |
| EP1963324B1 (en) * | 2005-12-22 | 2010-04-21 | Glaxo Group Limited | Heterocyclic compounds, their preparation and their use as antibacterials |
| JP2009532423A (ja) | 2006-04-06 | 2009-09-10 | グラクソ グループ リミテッド | 抗菌剤としてのピロロ−キノキサリノン誘導体 |
| GB0608263D0 (en) | 2006-04-26 | 2006-06-07 | Glaxo Group Ltd | Compounds |
| GB0613208D0 (en) * | 2006-07-03 | 2006-08-09 | Glaxo Group Ltd | Compounds |
| GB0705672D0 (en) * | 2007-03-23 | 2007-05-02 | Glaxo Group Ltd | Compounds |
| CL2008001002A1 (es) | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
| JP5389013B2 (ja) * | 2007-04-20 | 2014-01-15 | グラクソ グループ リミテッド | 抗菌剤としての三環式含窒素化合物 |
| GB0707706D0 (en) * | 2007-04-20 | 2007-05-30 | Glaxo Group Ltd | Compounds |
| EP2005995A1 (en) * | 2007-06-22 | 2008-12-24 | Glaxo Group Limited | Heterocyclic compounds for the treatment of tuberculosis |
| EP2080761A1 (en) | 2008-01-18 | 2009-07-22 | Glaxo Group Limited | Compounds |
| ES2411930T3 (es) | 2008-02-20 | 2013-07-09 | Actelion Pharmaceuticals Ltd. | Compuestos antibióticos azatricíclicos |
| CA2720672A1 (en) | 2008-04-15 | 2009-10-22 | Actelion Pharmaceuticals Ltd | Tricyclic antibiotics |
| WO2010015985A1 (en) | 2008-08-04 | 2010-02-11 | Actelion Pharmaceuticals Ltd | Tricyclic alkylaminomethyloxazolidinone derivatives |
| MY158520A (en) | 2008-10-07 | 2016-10-14 | Actelion Pharmaceuticals Ltd | Tricyclic oxazolidinone antibiotic compounds |
| JP2012505866A (ja) * | 2008-10-17 | 2012-03-08 | グラクソ グループ リミテッド | 抗菌剤として使用される三環式窒素化合物 |
| CN102232078B (zh) | 2008-12-12 | 2014-07-16 | 埃科特莱茵药品有限公司 | 5-氨基-2-(1-羟基-乙基)-四氢吡喃衍生物 |
| WO2010081874A1 (en) | 2009-01-15 | 2010-07-22 | Glaxo Group Limited | Naphthyridin-2 (1 h)-one compounds useful as antibacterials |
| WO2013038374A1 (en) | 2011-09-16 | 2013-03-21 | Actelion Pharmaceuticals Ltd | Process for manufacturing a synthetic intermediate |
| CA2854266A1 (en) | 2011-11-30 | 2013-06-06 | Actelion Pharmaceuticals Ltd | 3,7-disubstituted octahydro-2h-pyrido[4,3-e][1,3]oxazin-2-one antibiotics |
| AU2015304847B2 (en) | 2014-08-22 | 2018-10-25 | Glaxosmithkline Intellectual Property Development Limited | Tricyclic nitrogen containing compounds for treating Neisseria gonorrhoea infection |
| WO2018159609A1 (ja) | 2017-02-28 | 2018-09-07 | 三井化学アグロ株式会社 | 植物病害防除組成物およびそれを施用する植物病害の防除方法 |
| CA3063037A1 (en) * | 2017-05-10 | 2018-11-15 | Albajuna Therapeutics, S.L. | Fc-fusion protein derivatives with high dual hiv antiviral and immunomodulatory activity |
| AU2020394867A1 (en) | 2019-12-02 | 2022-05-26 | Storm Therapeutics Limited | Polyheterocyclic compounds as METTL3 inhibitors |
| PH12022551379A1 (en) | 2019-12-06 | 2023-05-03 | Vertex Pharma | Substituted tetrahydrofurans as modulators of sodium channels |
| DK4347031T3 (da) | 2021-06-04 | 2025-12-01 | Vertex Pharma | N-(hydroxyalkyl-(hetero)aryl)-tetrahydrofuran-carboxamider som modulatorer af natriumkanaler |
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| EP1963324B1 (en) * | 2005-12-22 | 2010-04-21 | Glaxo Group Limited | Heterocyclic compounds, their preparation and their use as antibacterials |
| JP2009532423A (ja) * | 2006-04-06 | 2009-09-10 | グラクソ グループ リミテッド | 抗菌剤としてのピロロ−キノキサリノン誘導体 |
| GB0608263D0 (en) * | 2006-04-26 | 2006-06-07 | Glaxo Group Ltd | Compounds |
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| GB0705672D0 (en) * | 2007-03-23 | 2007-05-02 | Glaxo Group Ltd | Compounds |
| EP1980251A1 (en) * | 2007-04-13 | 2008-10-15 | Glaxo Group Limited | Pyrrolo[3,2,1-ij]quinoline-4-one derivatives for treating tuberculosis |
| GB0707706D0 (en) * | 2007-04-20 | 2007-05-30 | Glaxo Group Ltd | Compounds |
| JP5389013B2 (ja) * | 2007-04-20 | 2014-01-15 | グラクソ グループ リミテッド | 抗菌剤としての三環式含窒素化合物 |
| GB0707708D0 (en) * | 2007-04-20 | 2007-05-30 | Glaxo Group Ltd | Compounds |
-
2006
- 2006-10-17 WO PCT/US2006/060023 patent/WO2007081597A2/en not_active Ceased
- 2006-10-17 SI SI200630624T patent/SI1954697T1/sl unknown
- 2006-10-17 HR HR20100194T patent/HRP20100194T8/xx unknown
- 2006-10-17 CA CA002626641A patent/CA2626641A1/en not_active Abandoned
- 2006-10-17 ES ES06849235T patent/ES2340531T3/es active Active
- 2006-10-17 AT AT06849235T patent/ATE458737T1/de active
- 2006-10-17 DE DE602006012535T patent/DE602006012535D1/de active Active
- 2006-10-17 NZ NZ567315A patent/NZ567315A/en unknown
- 2006-10-17 EP EP06849235A patent/EP1954697B1/en active Active
- 2006-10-17 BR BRPI0617467-1A patent/BRPI0617467A2/pt not_active IP Right Cessation
- 2006-10-17 DK DK06849235.4T patent/DK1954697T3/da active
- 2006-10-17 PT PT06849235T patent/PT1954697E/pt unknown
- 2006-10-17 EA EA200801128A patent/EA200801128A1/xx unknown
- 2006-10-17 US US12/090,947 patent/US20080280892A1/en not_active Abandoned
- 2006-10-17 JP JP2008536625A patent/JP2009512695A/ja active Pending
- 2006-10-17 KR KR1020087012082A patent/KR20080064173A/ko not_active Withdrawn
- 2006-10-17 AU AU2006335042A patent/AU2006335042A1/en not_active Abandoned
- 2006-10-17 US US11/550,005 patent/US20080221110A1/en not_active Abandoned
- 2006-10-17 PL PL06849235T patent/PL1954697T3/pl unknown
- 2006-10-19 PE PE2006001266A patent/PE20070793A1/es not_active Application Discontinuation
- 2006-10-19 AR ARP060104571A patent/AR057981A1/es not_active Application Discontinuation
- 2006-10-19 TW TW095138495A patent/TW200736263A/zh unknown
-
2008
- 2008-04-10 IL IL190803A patent/IL190803A0/en unknown
- 2008-04-15 MA MA30851A patent/MA29873B1/fr unknown
- 2008-04-25 CR CR9930A patent/CR9930A/es not_active Application Discontinuation
- 2008-05-13 NO NO20082191A patent/NO20082191L/no not_active Application Discontinuation
-
2010
- 2010-05-10 CY CY20101100405T patent/CY1110137T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007081597A2 (en) | 2007-07-19 |
| US20080221110A1 (en) | 2008-09-11 |
| DE602006012535D1 (de) | 2010-04-08 |
| EP1954697B1 (en) | 2010-02-24 |
| DK1954697T3 (da) | 2010-06-14 |
| WO2007081597A3 (en) | 2008-06-12 |
| TW200736263A (en) | 2007-10-01 |
| IL190803A0 (en) | 2008-12-29 |
| US20080280892A1 (en) | 2008-11-13 |
| HRP20100194T1 (hr) | 2010-05-31 |
| AU2006335042A1 (en) | 2007-07-19 |
| CY1110137T1 (el) | 2015-01-14 |
| ATE458737T1 (de) | 2010-03-15 |
| HK1118546A1 (en) | 2009-02-13 |
| EA200801128A1 (ru) | 2008-10-30 |
| SI1954697T1 (sl) | 2010-05-31 |
| BRPI0617467A2 (pt) | 2011-07-26 |
| PE20070793A1 (es) | 2007-08-23 |
| NO20082191L (no) | 2008-07-16 |
| CR9930A (es) | 2008-07-29 |
| CA2626641A1 (en) | 2007-07-19 |
| EP1954697A2 (en) | 2008-08-13 |
| JP2009512695A (ja) | 2009-03-26 |
| HRP20100194T8 (hr) | 2010-06-30 |
| MA29873B1 (fr) | 2008-10-03 |
| NZ567315A (en) | 2011-01-28 |
| KR20080064173A (ko) | 2008-07-08 |
| ES2340531T3 (es) | 2010-06-04 |
| PL1954697T3 (pl) | 2010-07-30 |
| PT1954697E (pt) | 2010-05-17 |
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| Date | Code | Title | Description |
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| FA | Abandonment or withdrawal |