HRP20100458T1 - Postupak priprave derivata benzimidazola - Google Patents
Postupak priprave derivata benzimidazola Download PDFInfo
- Publication number
- HRP20100458T1 HRP20100458T1 HR20100458T HRP20100458T HRP20100458T1 HR P20100458 T1 HRP20100458 T1 HR P20100458T1 HR 20100458 T HR20100458 T HR 20100458T HR P20100458 T HRP20100458 T HR P20100458T HR P20100458 T1 HRP20100458 T1 HR P20100458T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- acid
- image
- toluenesulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 9
- 238000002360 preparation method Methods 0.000 title claims 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 239000002253 acid Substances 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 150000001409 amidines Chemical class 0.000 claims abstract 3
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 3
- 230000008878 coupling Effects 0.000 claims abstract 3
- 238000010168 coupling process Methods 0.000 claims abstract 3
- 238000005859 coupling reaction Methods 0.000 claims abstract 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 2
- 150000004985 diamines Chemical class 0.000 claims abstract 2
- 238000002955 isolation Methods 0.000 claims abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- VRAVWQUXPCWGSU-UHFFFAOYSA-N bis(1h-1,2,4-triazol-5-yl)methanone Chemical compound N1=CNN=C1C(=O)C=1N=CNN=1 VRAVWQUXPCWGSU-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
Classifications
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- 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
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Postupak priprave spoja formule po izboru u obliku njegovih kiselinskih adicijskih soli, naznačen time, da u prvom koraku diamin formule 2 reagira pomoću karboksilne kiseline 3u prisutnosti prikladnog kupirajućeg reagensa, da bi formirao spoj formule 4koji se bez izoliranja prevede u hidrobromid formule 4-Br, koji se konačno prevede u amidin formule 1. Patent sadrži još 8 patentnih zahtjeva.
Claims (9)
1. Postupak priprave spoja formule
[image]
po izboru u obliku njegovih kiselinskih adicijskih soli, naznačen time, da u prvom koraku diamin formule 2
[image]
reagira pomoću karboksilne kiseline 3
[image]
u prisutnosti prikladnog kupirajućeg reagensa, da bi formirao spoj formule 4
[image]
koji se bez izoliranja prevede u hidrobromid formule 4-Br,
[image]
koji se konačno prevede u amidin formule 1.
2. Postupak u skladu sa zahtjevom 1, naznačen time, da se reakcija 2 sa 3 provodi u otapalu koje je izabrano između metilen klorida, dimetilformamida, benzena, toluena, klorobenzena, tetrahidrofurana, dioksana i njihovih smjesa.
3. Postupak u skladu sa zahtjevom 1 ili 2, naznačen time, da je kupirajući reagens izabran između N,N'-dicikloheksilkarbodiimida, N,N'-karbonildiimidazola i karbonil-di-(1,2,4-triazola).
4. Postupak u skladu s jednim od zahtjeva 1 do 3, naznačen time, da je za pripravu spoja formule 4 dodana octena kiselina.
5. Postupak u skladu s jednim od zahtjeva 1 do 4, naznačen time, da je spoj formule 4-Br dobiven iz spoja formule 4 dodavanjem vodene bromovodične kiseline.
6. Postupak u skladu s jednim od zahtjeva 1 do 5 za pripravu spoja formule 1 u obliku njegove kiselinske adicijske soli s p-toluensulfonskom kiselinom, naznačen time, da je prevođenje spoja formule 4-Br u amidin formule 1, u oblik njegove kiselinske adicijske soli s p-toluensulfonskom kiselinom, provedeno dodavanjem spoja formule 4-Br u alkohol koji sadrži kiselinu uz dodavanje p-toluensulfonske kiseline i neposredno zatim dodavanjem otopine amonijaka.
7. Postupak u skladu sa zahtjevom 6, naznačen time, da je ukupna količina p-toluensulfonske kiseline dodana na početku reakcije spoja formule 4-Br s alkoholom koji sadrži kiselinu.
8. Postupak u skladu s jednim od zahtjeva 6 ili 7, naznačen time, da alkohol koji sadrži kiselinu je etanol koji sadrži klorovodičnu kiselinu.
9. Spoj, naznačen time, da je formule 4-Br
[image]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07101822A EP1956018A1 (de) | 2007-02-06 | 2007-02-06 | Verfahren zur Herstellung eines Benzimidazolderivats |
| PCT/EP2008/051397 WO2008095928A1 (en) | 2007-02-06 | 2008-02-05 | Process for the preparation of a benzimidazole derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100458T1 true HRP20100458T1 (hr) | 2010-09-30 |
Family
ID=38166801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100458T HRP20100458T1 (hr) | 2007-02-06 | 2010-08-17 | Postupak priprave derivata benzimidazola |
Country Status (34)
| Country | Link |
|---|---|
| US (2) | US8119810B2 (hr) |
| EP (2) | EP1956018A1 (hr) |
| JP (1) | JP5247728B2 (hr) |
| KR (1) | KR20090116781A (hr) |
| CN (1) | CN101600709B (hr) |
| AR (1) | AR065196A1 (hr) |
| AT (1) | ATE476430T1 (hr) |
| AU (1) | AU2008212908B2 (hr) |
| BR (1) | BRPI0807197A2 (hr) |
| CA (1) | CA2675624C (hr) |
| CL (1) | CL2008000355A1 (hr) |
| CY (1) | CY1111045T1 (hr) |
| DE (1) | DE602008002057D1 (hr) |
| DK (1) | DK2118090T3 (hr) |
| EA (1) | EA015967B1 (hr) |
| EC (1) | ECSP099509A (hr) |
| ES (1) | ES2349905T3 (hr) |
| HK (1) | HK1136559A1 (hr) |
| HR (1) | HRP20100458T1 (hr) |
| IL (1) | IL199330A (hr) |
| MA (1) | MA31118B1 (hr) |
| MX (1) | MX2009006834A (hr) |
| MY (1) | MY148629A (hr) |
| NZ (1) | NZ579133A (hr) |
| PE (1) | PE20081737A1 (hr) |
| PL (1) | PL2118090T3 (hr) |
| PT (1) | PT2118090E (hr) |
| SI (1) | SI2118090T1 (hr) |
| TN (1) | TN2009000327A1 (hr) |
| TW (1) | TWI417291B (hr) |
| UA (1) | UA94988C2 (hr) |
| UY (1) | UY30888A1 (hr) |
| WO (1) | WO2008095928A1 (hr) |
| ZA (1) | ZA200906050B (hr) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005061623A1 (de) * | 2005-12-21 | 2007-06-28 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verbessertes Verfahren zur Herstellung von 4-(Benzimidazolylmethylamino)-Benzamidinen und deren Salzen |
| CZ305085B6 (cs) * | 2008-03-14 | 2015-04-29 | Zentiva, K.S. | Způsob přípravy dabigatranu |
| NZ586868A (en) * | 2008-03-28 | 2012-02-24 | Boehringer Ingelheim Int | Process for preparing orally administered dabigatran formulations |
| BRPI0914788B1 (pt) * | 2008-06-16 | 2020-04-07 | Boehringer Ingelheim Int | processo para produção de um produto intermediário de etexilato de dabigatran |
| CN102099012A (zh) * | 2008-07-14 | 2011-06-15 | 贝林格尔.英格海姆国际有限公司 | 制备含有达比加群的药物制剂的方法 |
| BRPI0921479A2 (pt) | 2008-11-11 | 2016-01-12 | Boehringer Ingelheim Int | método para tratamento ou prevenção de trombose usando etexilato de dabigatran ou um sal do mesmo com aprimorado perfil de segurança em relação à terapia convencional com varfarina |
| CN102050814B (zh) * | 2009-11-06 | 2014-05-28 | 北京美倍他药物研究有限公司 | 达比加群的酯衍生物 |
| CN102050815B (zh) * | 2009-11-06 | 2014-04-02 | 北京美倍他药物研究有限公司 | 作为前药的达比加群的酯衍生物 |
| US8399678B2 (en) | 2009-11-18 | 2013-03-19 | Boehringer Ingelheim International Gmbh | Process for the manufacture of dabigatran etexilate |
| EP2937343A1 (en) | 2010-07-09 | 2015-10-28 | Esteve Química, S.A. | Process of preparing a thrombin specific inhibitor |
| EP2649060B1 (en) | 2010-12-06 | 2017-04-05 | MSN Laboratories Limited | Process for the preparation of benzimidazole derivatives and its salts |
| CN102838588B (zh) * | 2011-06-24 | 2014-03-19 | 中国药科大学 | 一类可用于口服的凝血酶抑制剂、其制法以及医药用途 |
| CN102633713B (zh) * | 2012-03-22 | 2013-12-11 | 南京工业大学 | 达比加群酯中间体及其制备方法、以及制备达比加群酯的方法 |
| US9273030B2 (en) | 2012-04-02 | 2016-03-01 | Msn Laboratories Private Limited | Process for the preparation of benzimidazole derivatives and salts thereof |
| CN102911160B (zh) * | 2012-06-29 | 2014-10-22 | 上海奥博生物医药技术有限公司 | 一种制备和纯化达比加群酯中间体的方法 |
| JP2015522596A (ja) * | 2012-07-16 | 2015-08-06 | インテルキム、ソシエダッド アノニマ | ダビガトランエテキシラートの合成のための中間体を調製する方法及び該中間体の結晶形 |
| US10077251B2 (en) | 2012-10-29 | 2018-09-18 | Biophore India Pharmaceuticals Pvt. Ltd. | Process for the synthesis of Dabigatran Etexilate and its intermediates |
| US9533971B2 (en) | 2012-10-29 | 2017-01-03 | Biophore India Pharmaceuticals Pvt. Ltd | Process for the synthesis of dabigatran and its intermediates |
| CN102977077A (zh) * | 2012-11-28 | 2013-03-20 | 浙江燎原药业有限公司 | 一种达比加群酯中间体的制备方法 |
| CN103224469A (zh) * | 2013-05-16 | 2013-07-31 | 上海应用技术学院 | 一种以含氟基团修饰的苯环为中心的达比加群酯类似物及其合成方法 |
| CN103288744A (zh) * | 2013-06-04 | 2013-09-11 | 上海应用技术学院 | 一种含氟基团修饰的达比加群酯类似物及其合成方法 |
| CN104418839B (zh) * | 2013-08-26 | 2019-02-01 | 深圳翰宇药业股份有限公司 | 达比加群酯的合成方法 |
| CN103710406B (zh) * | 2013-12-05 | 2017-08-11 | 蚌埠丰原医药科技发展有限公司 | 一种酶促反应制备达比加群酯主要中间体的方法 |
| CN103772358A (zh) * | 2014-01-07 | 2014-05-07 | 万特制药(海南)有限公司 | 一种制备达比加群酯的合成方法 |
| CN104003977B (zh) * | 2014-06-05 | 2016-04-13 | 雅本化学股份有限公司 | N-(2-氯甲基-1-甲基-1h-苯并咪唑-5-酰基)-n-(吡啶-2-基) -3-氨基丙酸乙酯的制备方法 |
| CN104045628B (zh) * | 2014-06-13 | 2019-04-09 | 深圳翰宇药业股份有限公司 | 苯并咪唑衍生物的纯化方法 |
| CN105315257A (zh) * | 2014-06-24 | 2016-02-10 | 华仁药业股份有限公司 | 一种达比加群酯的合成及纯化方法 |
| JP6403865B2 (ja) | 2014-07-03 | 2018-10-10 | シャンハイ インスティテュート オブ ファーマシューティカル インダストリー | ダビガトランエテキシラート中間体の製造方法及び中間体化合物 |
| WO2016027077A1 (en) * | 2014-08-18 | 2016-02-25 | Cipla Limited | Processes for the preparation of dabigatran etexilate and intermediates thereof |
| CN104744438A (zh) * | 2014-12-17 | 2015-07-01 | 烟台东诚药业集团股份有限公司 | 一种用于合成制备达比加群酯苯并咪唑中间体的方法 |
| WO2016132296A1 (en) * | 2015-02-18 | 2016-08-25 | Piramal Enterprises Limited | A process for the preparation of an intermediate of dabigatran etexilate |
| CN105601615A (zh) * | 2015-11-17 | 2016-05-25 | 烟台东诚药业集团股份有限公司 | 一种用于纯化公斤级达比加群酯游离碱的方法 |
| CN105330645B (zh) * | 2015-11-30 | 2020-06-02 | 常州市阳光药业有限公司 | 达比加群酯中间体的制备方法 |
| CN106866626A (zh) * | 2015-12-14 | 2017-06-20 | 天津药物研究院有限公司 | 一种达比加群酯中间体的制备方法 |
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| US4632993A (en) * | 1984-10-11 | 1986-12-30 | Pfizer Inc. | Process for making 2-guanidino-4-(2-methyl-4-imidazolyl) thiazole dihydrobromide |
| JPH02283860A (ja) * | 1989-04-24 | 1990-11-21 | Nissan Motor Co Ltd | エンジンの点火時期制御装置 |
| US5233944A (en) * | 1989-08-08 | 1993-08-10 | Fuji Jukogyo Kabushiki Kaisha | Control apparatus for alcohol engine |
| GB9417310D0 (en) * | 1994-08-27 | 1994-10-19 | Pfizer Ltd | Therapeutic agents |
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| US6414008B1 (en) * | 1997-04-29 | 2002-07-02 | Boehringer Ingelheim Pharma Kg | Disubstituted bicyclic heterocycles, the preparation thereof, and their use as pharmaceutical compositions |
| GB0014006D0 (en) * | 2000-06-08 | 2000-08-02 | Smithkline Beecham Plc | Novel pharmaceutical |
| DE10230012A1 (de) * | 2002-07-04 | 2004-01-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue 5,6-Dihydro-4H-imidazo[4,5,1-ij]chinoline,ihre Herstellung und ihre Verwendung als Arzneimittel |
| DE10235639A1 (de) * | 2002-08-02 | 2004-02-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Prodrugs von 1-Methyl-2-(4-amidinophenylaminomethyl)-benzimidazol-5-yl-carbonsäure-(N-2-pyridyl-N-2-hydroxycarbonylethyl)-amid, ihre Herstellung und ihre Verwendung als Arzneimittel |
| EP1609784A1 (de) * | 2004-06-25 | 2005-12-28 | Boehringer Ingelheim Pharma GmbH & Co.KG | Verfahren zur Herstellung von 4-(Benzimidazolylmethylamino)-Benzamidinen |
| US7314033B2 (en) * | 2004-11-18 | 2008-01-01 | Massachusetts Institute Of Technology | Fuel management system for variable ethanol octane enhancement of gasoline engines |
| CN100509799C (zh) * | 2005-12-16 | 2009-07-08 | 复旦大学 | 一种合成非手性，非肽类的抗凝血酶抑制剂的方法 |
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2007
- 2007-02-06 EP EP07101822A patent/EP1956018A1/de not_active Ceased
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2008
- 2008-02-01 UY UY30888A patent/UY30888A1/es not_active Application Discontinuation
- 2008-02-04 PE PE2008000244A patent/PE20081737A1/es not_active Application Discontinuation
- 2008-02-05 PL PL08708696T patent/PL2118090T3/pl unknown
- 2008-02-05 JP JP2009547712A patent/JP5247728B2/ja active Active
- 2008-02-05 UA UAA200908939A patent/UA94988C2/ru unknown
- 2008-02-05 DE DE602008002057T patent/DE602008002057D1/de active Active
- 2008-02-05 ES ES08708696T patent/ES2349905T3/es active Active
- 2008-02-05 AR ARP080100495A patent/AR065196A1/es unknown
- 2008-02-05 MY MYPI20093227A patent/MY148629A/en unknown
- 2008-02-05 DK DK08708696.3T patent/DK2118090T3/da active
- 2008-02-05 AT AT08708696T patent/ATE476430T1/de active
- 2008-02-05 WO PCT/EP2008/051397 patent/WO2008095928A1/en active Application Filing
- 2008-02-05 AU AU2008212908A patent/AU2008212908B2/en not_active Ceased
- 2008-02-05 EP EP08708696A patent/EP2118090B1/en active Active
- 2008-02-05 SI SI200830078T patent/SI2118090T1/sl unknown
- 2008-02-05 PT PT08708696T patent/PT2118090E/pt unknown
- 2008-02-05 CA CA2675624A patent/CA2675624C/en not_active Expired - Fee Related
- 2008-02-05 EA EA200901039A patent/EA015967B1/ru not_active IP Right Cessation
- 2008-02-05 TW TW097104663A patent/TWI417291B/zh not_active IP Right Cessation
- 2008-02-05 NZ NZ579133A patent/NZ579133A/en not_active IP Right Cessation
- 2008-02-05 MX MX2009006834A patent/MX2009006834A/es active IP Right Grant
- 2008-02-05 CN CN2008800039517A patent/CN101600709B/zh not_active Expired - Fee Related
- 2008-02-05 CL CL200800355A patent/CL2008000355A1/es unknown
- 2008-02-05 US US12/525,867 patent/US8119810B2/en active Active
- 2008-02-05 BR BRPI0807197-7A patent/BRPI0807197A2/pt not_active IP Right Cessation
- 2008-02-05 KR KR1020097018468A patent/KR20090116781A/ko active IP Right Grant
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2009
- 2009-06-11 IL IL199330A patent/IL199330A/en not_active IP Right Cessation
- 2009-07-10 EC EC2009009509A patent/ECSP099509A/es unknown
- 2009-07-31 MA MA32129A patent/MA31118B1/fr unknown
- 2009-07-31 TN TNP2009000327A patent/TN2009000327A1/fr unknown
- 2009-09-01 ZA ZA200906050A patent/ZA200906050B/xx unknown
-
2010
- 2010-03-30 HK HK10103270.3A patent/HK1136559A1/xx not_active IP Right Cessation
- 2010-08-17 HR HR20100458T patent/HRP20100458T1/hr unknown
- 2010-10-25 CY CY20101100957T patent/CY1111045T1/el unknown
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2012
- 2012-01-17 US US13/351,621 patent/US8455650B2/en active Active
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