AR056868A1 - Nitrooxi derivados de esteroides, composiciones farmaceuticas y su uso para tratar trastornos de la piel o de la membrana mucosa - Google Patents
Nitrooxi derivados de esteroides, composiciones farmaceuticas y su uso para tratar trastornos de la piel o de la membrana mucosaInfo
- Publication number
- AR056868A1 AR056868A1 ARP060103835A ARP060103835A AR056868A1 AR 056868 A1 AR056868 A1 AR 056868A1 AR P060103835 A ARP060103835 A AR P060103835A AR P060103835 A ARP060103835 A AR P060103835A AR 056868 A1 AR056868 A1 AR 056868A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- group
- ono2
- integer
- alkyl
- Prior art date
Links
- 150000003431 steroids Chemical class 0.000 title abstract 2
- 210000004400 mucous membrane Anatomy 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229910004679 ONO2 Inorganic materials 0.000 abstract 11
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003246 corticosteroid Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- -1 nitrooxy steroid Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Chemical group 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
- A61P5/44—Glucocorticosteroids; Drugs increasing or potentiating the activity of glucocorticosteroids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Estos nitrooxi derivados de esteroides poseen una alta actividad farmacologica y una aumentada tolerabilidad local. Reivindicacion 1: Compuestos de formula general (1): R-Z-X-ONO2, donde R representa el residuo de corticosteroide de formula (2), donde R1 significa OC(O)OmRi donde m es 0 o 1, Ri significa alquil C1-10 de cadena ramificada o lineal; R2 significa un átomo de hidrogeno o -CH3; o R1 y R2 cuando se toman conjuntamente significan el grupo de formula (3), donde RA1 y RA2 se seleccionan independientemente entre H, alquil C1-10 de cadena lineal o ramificada; R1 y R2 pueden estar unidos a los átomos de carbono en 16 y 17 de la estructura esteroide en posicion a o b; R3 significa un átomo de hidrogeno o un átomo de fluor; Z significa un grupo capaz de enlazar X seleccionado entre el grupo que consiste en: -C(O)-, -C(O)O- o la estructura de formula (4), donde R' y R'' se seleccionan independientemente entre H o alquil C1-4 de cadena ramificada o lineal; X significa un radical bivalente que tiene los significados siguientes: a) alquileno C1-20 de cadena lineal o ramificada, siendo sustituido opcionalmente por uno o más de los sustituyentes seleccionados entre el grupo que consiste en átomos de halogeno, hidroxi, - ONO2 o T, donde T significa -OC(O)(alquil C1-10)-ONO2 o -O(alquil C1-10)-ONO2; b) un grupo cicloalquileno C5-7 sustituido opcionalmente por un grupo alquil C1-10 de cadena lineal o ramificada; c) es de formula (5); d) es de formula (6), donde n es un numero entero de 0 a 20; n1 es un numero entero de 1 a 20; e) es de formula (7), donde: n1a es un numero entero de 1 a 20; Z1 significa -C(O)O- o OC(O)-; n es como se define anteriormente; n1 es como se define anteriormente; con la condicion de que cuando X se selecciona entre los radicales bivalentes mencionados en c)-e), el grupo -ONO2 de formula (1) está unido al grupo -(CH2)n1; f) es de formula (8), donde: Y1 significa -CH2-CH2-(CH2)n2a-, o -CH=CH(CH2)n2a donde n2a es un numero entero de 0 a 10; Z1a significa -OC(O)- o -C(O)O-; n2 es 0 o 1; R2 significa H o CH3; X1 significa -(CH)n1a- donde n1a es como se define anteriormente, o el radical bivalente de formula (6) donde n y n1 son como se definen anteriormente; con la condicion de que en la formula (8) el grupo -ONO2 de formula (1) esté unido al grupo X1; g) es de formula (9), donde: Y1 significa -CH2-CH2-(CH2)n2a-, o -CH=CH-(CH2)n2a donde n2a es un numero entero de 0 a 10; n3a es 0 o 1; Z1 significa -C(O)O- o -OC(O)-; n2 es 0 o 1; R2 significa H o CH3, X1 significa -(CH)n1a- donde n es como se define anteriormente, o el radical bivalente de formula (6) donde n y n1 son como se definen anteriormente; con la condicion de que en la formula (9) el grupo -ONO2 de formula (1) esté unido al grupo X1; h) -[(CH2)n3b-X2]n3-(CH2)n3c-, donde: X2 significa -O- o -S-; n3 es un numero entero de 1 a 6; n3b es un numero entero de 1 a 10; n3c es un numero entero de 1 a 10; i) es de formula (10), donde: n4 es un numero entero de 0 a 10; n5 es un numero entero de 1 a 10; R4, R5, R6 y R7 son iguales o diferentes y significan H o alquil C1-4 de cadena lineal o ramificada; donde el grupo -ONO2 de formula (1) está unido a l[C]n5, donde n5 es como se define anteriormente; Y2 significa un anillo heterocíclico saturado, no saturado o aromático de 5 o 6 miembros, que contiene uno o más heteroátomos seleccionados entre nitrogeno, oxígeno y azufre, y se selecciona entre las estructuras del grupo de formulas (11); con la condicion de que cuando en la formula (1) Z significa -C(O)- y en la formula (2) R1 y R2 ambos en posicion a se toman conjuntamente y forma el grupo de formula (3) donde RA1 y RA2 significan -CH3, R3 significa un átomo de fluor, entonces X no tiene el siguiente significado: a) alquileno C1-20 de cadena lineal o ramificada sustituido opcionalmente por uno o más de los sustituyentes seleccionados entre el grupo que consiste en: átomos de halogeno, hidroxi, -ONO2 o T, donde T significa - OC(O)(alquil C1-10)-ONO2 o -O(alquil C1-10)-ONO2.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05019155 | 2005-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR056868A1 true AR056868A1 (es) | 2007-10-31 |
Family
ID=37450883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP060103835A AR056868A1 (es) | 2005-09-02 | 2006-09-01 | Nitrooxi derivados de esteroides, composiciones farmaceuticas y su uso para tratar trastornos de la piel o de la membrana mucosa |
Country Status (19)
| Country | Link |
|---|---|
| US (5) | US20080221073A1 (es) |
| EP (1) | EP1940863B1 (es) |
| JP (1) | JP5216589B2 (es) |
| KR (1) | KR20080039442A (es) |
| CN (2) | CN101300265A (es) |
| AR (1) | AR056868A1 (es) |
| AU (1) | AU2006286838C1 (es) |
| BR (1) | BRPI0614967A2 (es) |
| CA (1) | CA2621117A1 (es) |
| ES (1) | ES2393363T3 (es) |
| IL (2) | IL189337A0 (es) |
| NO (1) | NO20081614L (es) |
| NZ (1) | NZ566128A (es) |
| RU (1) | RU2415864C2 (es) |
| SG (1) | SG158916A1 (es) |
| TW (1) | TW200801031A (es) |
| UY (1) | UY29779A1 (es) |
| WO (1) | WO2007025632A2 (es) |
| ZA (1) | ZA200801789B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8802726B2 (en) | 2006-02-03 | 2014-08-12 | Nicox S.A. | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies |
| US8933062B2 (en) * | 2007-02-05 | 2015-01-13 | Nicox S.A. | Nitric oxide releasing steroids |
| EP1964550A1 (en) * | 2007-03-01 | 2008-09-03 | NicOx S.A. | Glucocorticoid-nitrooxyderivative compositions |
| ES2324007A1 (es) * | 2007-10-25 | 2009-07-28 | Ferrer Internacional, S.A. | Una forma amorfa de un compuesto antiinflamatorio. |
| MX2011001119A (es) * | 2008-07-31 | 2011-03-02 | Nicox Sa | Glucocorticoides unidos a esteres de nitrato por medio de un enlazador aromatico en la posicion 21 y su uso en oftalmololgia. |
| EP2321333A1 (en) * | 2008-08-05 | 2011-05-18 | Nicox S.A. | New no-releasing steroids for the treatment of retina and macula lutea diseases |
| WO2010015529A1 (en) * | 2008-08-05 | 2010-02-11 | Nicox S.A. | New no releasing steroids derivatives |
| US8062653B2 (en) | 2009-02-18 | 2011-11-22 | Bezwada Biomedical, Llc | Controlled release of nitric oxide and drugs from functionalized macromers and oligomers |
| WO2010096320A2 (en) * | 2009-02-18 | 2010-08-26 | Bezwada Biomedical, Llc | Controlled release of nitric oxide and drugs from functionalized macromers and oligomers |
| US9022788B2 (en) * | 2009-10-17 | 2015-05-05 | Gregory John Stahler | System and method for cardiac defibrillation response simulation in health training mannequin |
| ES2359708B1 (es) * | 2009-11-16 | 2012-03-30 | Ferrer Internacional S.A. | Procedimiento de preparación de la (11beta,16alfa)-9-fluoro-11-hidroxi-16,17-[1-metil-etilidenebis(oxi)]-21-[1-oxo-[4-(nitrooximetil)benzoxi]]preña-1,4-dien-3,20-diona. |
| ES2362894B1 (es) | 2009-11-16 | 2012-05-21 | Ferrer Internacional S.A. | Procedimiento de preparación del �?cido 4-nitro-oxi-metil-benzoico. |
| JP7146750B2 (ja) * | 2016-10-14 | 2022-10-04 | ヴァン アンデル リサーチ インスティテュート | 非常に強力な糖質コルチコイドの構造およびデザインのための機構 |
| AU2021241591A1 (en) | 2020-03-24 | 2022-10-20 | Michael W. BURNET | Anti-infective and anti-viral compounds and compositions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56138200A (en) | 1980-02-15 | 1981-10-28 | Glaxo Group Ltd | Androstane carbothioate compound |
| GR1001529B (el) * | 1990-09-07 | 1994-03-31 | Elmuquimica Farm Sl | Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης. |
| US5824669A (en) * | 1996-03-22 | 1998-10-20 | Nitromed, Inc. | Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders |
| US5837698A (en) * | 1996-05-02 | 1998-11-17 | G. D. Searle & Co. | Steroid nitrite and nitrate ester derivatives useful as anti-inflammatory drugs |
| US5985862A (en) * | 1996-05-02 | 1999-11-16 | G.D. Searle & Co. | Pharmaceutical compositions having steroid nitrate ester derivatives useful as anti-inflammatory drugs |
| IT1285770B1 (it) * | 1996-10-04 | 1998-06-18 | Nicox Sa | Composti corticoidei |
| IT1311922B1 (it) | 1999-04-13 | 2002-03-20 | Nicox Sa | Composti farmaceutici. |
| ITMI20020148A1 (it) * | 2002-01-29 | 2003-07-29 | Nicox Sa | Nuovi corticosteroidi |
| EP1336602A1 (en) * | 2002-02-13 | 2003-08-20 | Giovanni Scaramuzzino | Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases |
-
2006
- 2006-08-04 US US12/065,561 patent/US20080221073A1/en not_active Abandoned
- 2006-08-04 AU AU2006286838A patent/AU2006286838C1/en not_active Ceased
- 2006-08-04 SG SG201000520-5A patent/SG158916A1/en unknown
- 2006-08-04 NZ NZ566128A patent/NZ566128A/en not_active IP Right Cessation
- 2006-08-04 RU RU2008111076/04A patent/RU2415864C2/ru not_active IP Right Cessation
- 2006-08-04 WO PCT/EP2006/007746 patent/WO2007025632A2/en not_active Ceased
- 2006-08-04 JP JP2008528372A patent/JP5216589B2/ja not_active Expired - Fee Related
- 2006-08-04 EP EP06776617A patent/EP1940863B1/en active Active
- 2006-08-04 ES ES06776617T patent/ES2393363T3/es active Active
- 2006-08-04 KR KR1020087004591A patent/KR20080039442A/ko not_active Ceased
- 2006-08-04 CN CNA2006800405622A patent/CN101300265A/zh active Pending
- 2006-08-04 CA CA002621117A patent/CA2621117A1/en not_active Abandoned
- 2006-08-04 BR BRPI0614967-7A patent/BRPI0614967A2/pt not_active IP Right Cessation
- 2006-08-04 CN CN2011100265155A patent/CN102134269A/zh active Pending
- 2006-09-01 UY UY29779A patent/UY29779A1/es unknown
- 2006-09-01 AR ARP060103835A patent/AR056868A1/es not_active Application Discontinuation
- 2006-09-01 TW TW095132322A patent/TW200801031A/zh unknown
-
2008
- 2008-02-07 IL IL189337A patent/IL189337A0/en unknown
- 2008-02-25 ZA ZA200801789A patent/ZA200801789B/xx unknown
- 2008-04-01 NO NO20081614A patent/NO20081614L/no not_active Application Discontinuation
-
2009
- 2009-06-26 US US12/492,404 patent/US20090264394A1/en not_active Abandoned
- 2009-06-26 US US12/492,337 patent/US20090264393A1/en not_active Abandoned
- 2009-06-26 US US12/492,359 patent/US20090258849A1/en not_active Abandoned
-
2011
- 2011-08-10 US US13/207,231 patent/US20110294769A1/en not_active Abandoned
- 2011-11-22 IL IL216516A patent/IL216516A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20081614L (no) | 2008-05-28 |
| SG158916A1 (en) | 2010-02-26 |
| KR20080039442A (ko) | 2008-05-07 |
| RU2415864C2 (ru) | 2011-04-10 |
| AU2006286838C1 (en) | 2013-05-02 |
| US20110294769A1 (en) | 2011-12-01 |
| IL216516A0 (en) | 2011-12-29 |
| UY29779A1 (es) | 2006-12-29 |
| US20090258849A1 (en) | 2009-10-15 |
| JP5216589B2 (ja) | 2013-06-19 |
| WO2007025632A3 (en) | 2007-04-19 |
| US20090264394A1 (en) | 2009-10-22 |
| BRPI0614967A2 (pt) | 2013-01-01 |
| AU2006286838A1 (en) | 2007-03-08 |
| ES2393363T3 (es) | 2012-12-20 |
| CA2621117A1 (en) | 2007-03-08 |
| WO2007025632A2 (en) | 2007-03-08 |
| JP2009506994A (ja) | 2009-02-19 |
| EP1940863A2 (en) | 2008-07-09 |
| US20080221073A1 (en) | 2008-09-11 |
| CN102134269A (zh) | 2011-07-27 |
| RU2008111076A (ru) | 2009-10-10 |
| TW200801031A (en) | 2008-01-01 |
| NZ566128A (en) | 2011-03-31 |
| AU2006286838B2 (en) | 2012-03-29 |
| EP1940863B1 (en) | 2012-09-05 |
| CN101300265A (zh) | 2008-11-05 |
| US20090264393A1 (en) | 2009-10-22 |
| IL189337A0 (en) | 2008-06-05 |
| ZA200801789B (en) | 2008-12-31 |
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