JP2010526129A5 - - Google Patents
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- Publication number
- JP2010526129A5 JP2010526129A5 JP2010507003A JP2010507003A JP2010526129A5 JP 2010526129 A5 JP2010526129 A5 JP 2010526129A5 JP 2010507003 A JP2010507003 A JP 2010507003A JP 2010507003 A JP2010507003 A JP 2010507003A JP 2010526129 A5 JP2010526129 A5 JP 2010526129A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- imidazo
- propyl
- quinolin
- 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.)
- Granted
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 113
- -1 cyano, hydroxyl Chemical group 0.000 claims 47
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 31
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- DZDHFZCICVMMQD-UHFFFAOYSA-N 2-butyl-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(NC(CCCC)=N3)C3=C(N)N=C21 DZDHFZCICVMMQD-UHFFFAOYSA-N 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- YCIZKSICGIPAEO-UHFFFAOYSA-N 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetic acid Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(O)=O)C=C1 YCIZKSICGIPAEO-UHFFFAOYSA-N 0.000 claims 3
- SJSFGOVQBUMHOZ-UHFFFAOYSA-N 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-[2-(methoxymethyl)pyrrolidin-1-yl]acetyl]amino]methyl]phenyl]acetic acid Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1C(CCC1)COC)CC1=CC=C(CC(O)=O)C=C1 SJSFGOVQBUMHOZ-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims 2
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- RHZLHOFJXJVOTC-UHFFFAOYSA-N 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(3-hydroxypyrrolidin-1-yl)acetyl]amino]methyl]phenyl]acetic acid Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CC(O)CC1)CC1=CC=CC(CC(O)=O)=C1 RHZLHOFJXJVOTC-UHFFFAOYSA-N 0.000 claims 2
- WHUUQTCYWBGMKC-UHFFFAOYSA-N 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(3-hydroxypyrrolidin-1-yl)acetyl]amino]methyl]phenyl]acetic acid Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CC(O)CC1)CC1=CC=C(CC(O)=O)C=C1 WHUUQTCYWBGMKC-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- XIQQEASYCSFTBJ-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propylamino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNCC1=CC=C(CC(=O)OC)C=C1 XIQQEASYCSFTBJ-UHFFFAOYSA-N 0.000 claims 2
- NIOHPZFOZHREKH-UHFFFAOYSA-N methyl 2-[4-[[acetyl-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(C)=O)CC1=CC=C(CC(=O)OC)C=C1 NIOHPZFOZHREKH-UHFFFAOYSA-N 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- YBFLUZIAQFUZKL-UHFFFAOYSA-N 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-(2-pyrrolidin-1-ylacetyl)amino]methyl]phenyl]acetic acid Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCCC1)CC1=CC=C(CC(O)=O)C=C1 YBFLUZIAQFUZKL-UHFFFAOYSA-N 0.000 claims 1
- REZHJFVAYCYQRR-UHFFFAOYSA-N 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-[2-hydroxyethyl(methyl)amino]acetyl]amino]methyl]phenyl]acetic acid Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)CCO)CC1=CC=C(CC(O)=O)C=C1 REZHJFVAYCYQRR-UHFFFAOYSA-N 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 208000005176 Hepatitis C Diseases 0.000 claims 1
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 claims 1
- ITATYELQCJRCCK-UHFFFAOYSA-N Mandelic Acid, Methyl Ester Chemical compound COC(=O)C(O)C1=CC=CC=C1 ITATYELQCJRCCK-UHFFFAOYSA-N 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 208000002672 hepatitis B Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91658607P | 2007-05-08 | 2007-05-08 | |
| US60/916,586 | 2007-05-08 | ||
| US2495708P | 2008-01-31 | 2008-01-31 | |
| US60/024,957 | 2008-01-31 | ||
| PCT/GB2008/050328 WO2008135791A1 (en) | 2007-05-08 | 2008-05-06 | Imidazoquinolines with immuno-modulating properties |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010526129A JP2010526129A (ja) | 2010-07-29 |
| JP2010526129A5 true JP2010526129A5 (esLanguage) | 2011-06-02 |
| JP5400763B2 JP5400763B2 (ja) | 2014-01-29 |
Family
ID=39596464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010507003A Expired - Fee Related JP5400763B2 (ja) | 2007-05-08 | 2008-05-06 | 免疫調節特性を有するイミダゾキノリン類 |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US8436178B2 (esLanguage) |
| EP (1) | EP2155743B1 (esLanguage) |
| JP (1) | JP5400763B2 (esLanguage) |
| KR (1) | KR20100016289A (esLanguage) |
| CN (1) | CN101687867B (esLanguage) |
| AR (1) | AR066492A1 (esLanguage) |
| AU (1) | AU2008247165B2 (esLanguage) |
| BR (1) | BRPI0811125A2 (esLanguage) |
| CA (1) | CA2686163A1 (esLanguage) |
| CL (1) | CL2008001357A1 (esLanguage) |
| CO (1) | CO6251247A2 (esLanguage) |
| CY (1) | CY1113339T1 (esLanguage) |
| DK (1) | DK2155743T3 (esLanguage) |
| EC (1) | ECSP099750A (esLanguage) |
| ES (1) | ES2393037T3 (esLanguage) |
| HR (1) | HRP20120895T1 (esLanguage) |
| IL (1) | IL201572A0 (esLanguage) |
| MX (1) | MX2009011802A (esLanguage) |
| MY (1) | MY150519A (esLanguage) |
| PE (1) | PE20090276A1 (esLanguage) |
| PL (1) | PL2155743T3 (esLanguage) |
| PT (1) | PT2155743E (esLanguage) |
| RU (1) | RU2475487C2 (esLanguage) |
| TW (1) | TW200902529A (esLanguage) |
| UY (1) | UY31069A1 (esLanguage) |
| WO (1) | WO2008135791A1 (esLanguage) |
| ZA (1) | ZA200907547B (esLanguage) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI392678B (zh) | 2004-03-26 | 2013-04-11 | Dainippon Sumitomo Pharma Co | ９-取代-８-氧基腺嘌呤化合物 |
| JP2009542645A (ja) * | 2006-07-05 | 2009-12-03 | アストラゼネカ・アクチエボラーグ | Ｔｌｒ７のモジュレーターとして作用する８−オキソアデニン誘導体 |
| TW200831105A (en) | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| JP5480637B2 (ja) * | 2007-03-19 | 2014-04-23 | アストラゼネカ・アクチエボラーグ | Ｔｏｌｌ様受容体（ｔｌｒ７）モジュレーターとしての９−置換−８−オキソ−アデニン化合物 |
| ATE530549T1 (de) * | 2007-03-19 | 2011-11-15 | Astrazeneca Ab | 9-substituierte 8-oxoadeninverbindungen als modulatoren des toll-like-receptor (tlr7) |
| PE20081887A1 (es) * | 2007-03-20 | 2009-01-16 | Dainippon Sumitomo Pharma Co | Nuevo compuesto de adenina |
| US8044056B2 (en) * | 2007-03-20 | 2011-10-25 | Dainippon Sumitomo Pharma Co., Ltd. | Adenine compound |
| DK2155743T3 (da) * | 2007-05-08 | 2012-11-05 | Astrazeneca Ab | Imidazoquinoliner med immunmodulerende egenskaber |
| MX2009013832A (es) * | 2007-06-29 | 2010-03-10 | Gilead Sciences Inc | Derivados de purina y su uso como moduladores del receptor 7 similar a un puente. |
| PE20091236A1 (es) | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| UY31531A1 (es) | 2007-12-17 | 2009-08-03 | Sales derivadas de 8-oxoadenina composiciones farmacéuticas que las contienen y su uso en terapia como moduladores de receptor tipo toll (tlr) | |
| WO2009091032A1 (ja) * | 2008-01-17 | 2009-07-23 | Dainippon Sumitomo Pharma Co., Ltd. | アデニン化合物の製造方法 |
| WO2009091031A1 (ja) * | 2008-01-17 | 2009-07-23 | Dainippon Sumitomo Pharma Co., Ltd. | アデニン化合物の製造方法 |
| CA2716706C (en) * | 2008-03-03 | 2014-02-18 | Irm Llc | Compounds and compositions as tlr activity modulators |
| MX344330B (es) | 2008-03-24 | 2016-12-13 | 4Sc Ag | Imidazoquinolinas substituidas novedosas. |
| NZ612380A (en) | 2008-12-09 | 2015-01-30 | Gilead Sciences Inc | Modulators of toll-like receptors |
| GB0908772D0 (en) * | 2009-05-21 | 2009-07-01 | Astrazeneca Ab | New salts 756 |
| BR112012004806B8 (pt) | 2009-09-02 | 2022-10-04 | Novartis Ag | composições imunogênicas que incluem moduladores da atividade de tlr, método para aumento da eficácia da referida composição e uso |
| EP2477987B1 (en) | 2009-09-14 | 2018-01-10 | Gilead Sciences, Inc. | Modulators of toll-like receptors |
| WO2011049825A1 (en) | 2009-10-22 | 2011-04-28 | Gilead Sciences, Inc. | Derivatives of purine or deazapurine useful for the treatment of (inter alia) viral infections |
| EP2507237A1 (en) * | 2009-12-03 | 2012-10-10 | Dainippon Sumitomo Pharma Co., Ltd. | Imidazoquinolines which act via toll - like receptors (tlr) |
| WO2011084725A1 (en) * | 2009-12-21 | 2011-07-14 | 3M Innovative Properties Company | 4-AMINO-2-(ETHOXYMETHYL)-1-(2-HYDROXY-2-METHYLPROPYL)-1H-IMIDAZO[4,5-c]QUINOLIN-5-IUM 1-HYDROXYNAPHTHALENE-2-CARBOXYLATE COMPOSITIONS AND METHODS |
| US20110150836A1 (en) * | 2009-12-22 | 2011-06-23 | Gilead Sciences, Inc. | Methods of treating hbv and hcv infection |
| AU2011295853A1 (en) | 2010-09-01 | 2013-04-04 | Irm Llc | Adsorption of immunopotentiators to insoluble metal salts |
| CN103370317B (zh) * | 2010-12-16 | 2015-10-07 | 阿斯利康(瑞典)有限公司 | 可用于治疗的咪唑并[4,5-c]喹啉-1-基衍生物 |
| JP5978226B2 (ja) | 2010-12-17 | 2016-08-24 | 大日本住友製薬株式会社 | プリン誘導体 |
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| CN104519910B (zh) | 2012-03-07 | 2017-05-03 | 诺华股份有限公司 | 肺炎链球菌抗原的含佐剂制剂 |
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| AU2013261267B2 (en) | 2012-05-18 | 2017-06-29 | Sumitomo Pharma Co., Ltd. | Carboxylic acid compounds |
| CA2882619A1 (en) | 2012-09-06 | 2014-03-13 | Novartis Ag | Combination vaccines with serogroup b meningococcus and d/t/p |
| JP2017503803A (ja) | 2014-01-10 | 2017-02-02 | シャンハイ バーディー バイオテック インコーポレイテッド | Ｅｇｆｒ発現腫瘍を処置するための化合物及び組成物 |
| AU2015286043B2 (en) | 2014-07-09 | 2020-08-20 | Birdie Biopharmaceuticals Inc. | Anti-PD-L1 combinations for treating tumors |
| TWI733652B (zh) | 2014-07-11 | 2021-07-21 | 美商基利科學股份有限公司 | 用於治療ＨＩＶ之ｔｏｌｌ樣受體調節劑 |
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| WO2019048036A1 (en) * | 2017-09-06 | 2019-03-14 | Biontech Ag | SUBSTITUTED IMIDAZOQUINOLINES |
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| SG11202100706UA (en) | 2018-07-23 | 2021-03-30 | Japan As Represented By Director General Of Nat Institute Of Infectious Diseases | Composition containing influenza vaccine |
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- 2008-05-06 DK DK08737252.0T patent/DK2155743T3/da active
- 2008-05-06 PL PL08737252T patent/PL2155743T3/pl unknown
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- 2008-05-06 JP JP2010507003A patent/JP5400763B2/ja not_active Expired - Fee Related
- 2008-05-06 ES ES08737252T patent/ES2393037T3/es active Active
- 2008-05-06 KR KR1020097023214A patent/KR20100016289A/ko not_active Withdrawn
- 2008-05-06 RU RU2009140465/04A patent/RU2475487C2/ru not_active IP Right Cessation
- 2008-05-06 PT PT08737252T patent/PT2155743E/pt unknown
- 2008-05-06 MX MX2009011802A patent/MX2009011802A/es active IP Right Grant
- 2008-05-06 EP EP08737252A patent/EP2155743B1/en active Active
- 2008-05-06 HR HRP20120895AT patent/HRP20120895T1/hr unknown
- 2008-05-06 WO PCT/GB2008/050328 patent/WO2008135791A1/en not_active Ceased
- 2008-05-06 BR BRPI0811125A patent/BRPI0811125A2/pt not_active IP Right Cessation
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