DK2035368T3 - Fremgangsmåde til fremstilling af (r)-(-)-3-(carbamoylmethyl)-5- methylhexansyre og af pregabalin- og syntesemellemprodukter - Google Patents
Fremgangsmåde til fremstilling af (r)-(-)-3-(carbamoylmethyl)-5- methylhexansyre og af pregabalin- og syntesemellemprodukter Download PDFInfo
- Publication number
- DK2035368T3 DK2035368T3 DK07766518.0T DK07766518T DK2035368T3 DK 2035368 T3 DK2035368 T3 DK 2035368T3 DK 07766518 T DK07766518 T DK 07766518T DK 2035368 T3 DK2035368 T3 DK 2035368T3
- Authority
- DK
- Denmark
- Prior art keywords
- carbamoylmethyl
- methylhexanoic acid
- acid
- salt
- naphthyl
- Prior art date
Links
- NPDKTSLVWGFPQG-SSDOTTSWSA-N (3r)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid Chemical compound CC(C)C[C@H](CC(N)=O)CC(O)=O NPDKTSLVWGFPQG-SSDOTTSWSA-N 0.000 title claims description 58
- 238000000034 method Methods 0.000 title claims description 26
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 22
- 229960001233 pregabalin Drugs 0.000 title claims description 15
- 239000000543 intermediate Substances 0.000 title claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 35
- 150000001412 amines Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 25
- NPDKTSLVWGFPQG-ZETCQYMHSA-N (3s)-3-(2-amino-2-oxoethyl)-5-methylhexanoic acid Chemical compound CC(C)C[C@@H](CC(N)=O)CC(O)=O NPDKTSLVWGFPQG-ZETCQYMHSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 17
- IJXJGQCXFSSHNL-MRVPVSSYSA-N (2s)-2-amino-2-phenylethanol Chemical compound OC[C@@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-MRVPVSSYSA-N 0.000 claims description 16
- RTCUCQWIICFPOD-SECBINFHSA-N (1r)-1-naphthalen-1-ylethanamine Chemical group C1=CC=C2C([C@H](N)C)=CC=CC2=C1 RTCUCQWIICFPOD-SECBINFHSA-N 0.000 claims description 15
- 239000012452 mother liquor Substances 0.000 claims description 14
- IJXJGQCXFSSHNL-QMMMGPOBSA-N (R)-(-)-2-Phenylglycinol Chemical compound OC[C@H](N)C1=CC=CC=C1 IJXJGQCXFSSHNL-QMMMGPOBSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000002244 precipitate Substances 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- -1 carbamoylmethyl Chemical group 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- RTCUCQWIICFPOD-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(C(N)C)=CC=CC2=C1 RTCUCQWIICFPOD-UHFFFAOYSA-N 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- RTCUCQWIICFPOD-VIFPVBQESA-N (1s)-1-naphthalen-1-ylethanamine Chemical class C1=CC=C2C([C@@H](N)C)=CC=CC2=C1 RTCUCQWIICFPOD-VIFPVBQESA-N 0.000 claims description 6
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- 239000007787 solid Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- NPDKTSLVWGFPQG-UHFFFAOYSA-N 3-(2-amino-2-oxoethyl)-5-methylhexanoic acid Chemical class CC(C)CC(CC(N)=O)CC(O)=O NPDKTSLVWGFPQG-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UATSLDZQNXAKMA-UHFFFAOYSA-N 3-(2-methylpropyl)pentanedioic acid Chemical compound CC(C)CC(CC(O)=O)CC(O)=O UATSLDZQNXAKMA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical class OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102220079670 rs759826252 Human genes 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/20—Preparation of optical isomers by separation of optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
- C07C227/32—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT001297A ITMI20061297A1 (it) | 2006-07-04 | 2006-07-04 | Procedimento per la preparazione della'acido (r)-(-)-3-(carbamoilmetil)-5-metilesanoico e del pregabalin e intermedi di sintesi |
| PCT/IB2007/001514 WO2008004044A1 (en) | 2006-07-04 | 2007-06-06 | Process for the preparation of (r)-(-)-3-(carbamoylmethyl)-5-methylhexanoic acid and of pregabalin and synthesis intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2035368T3 true DK2035368T3 (da) | 2015-08-24 |
Family
ID=38669439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK07766518.0T DK2035368T3 (da) | 2006-07-04 | 2007-06-06 | Fremgangsmåde til fremstilling af (r)-(-)-3-(carbamoylmethyl)-5- methylhexansyre og af pregabalin- og syntesemellemprodukter |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8563775B2 (da) |
| EP (1) | EP2035368B1 (da) |
| JP (1) | JP5202519B2 (da) |
| CN (1) | CN101500985B (da) |
| CA (1) | CA2656122C (da) |
| CY (1) | CY1116498T1 (da) |
| DK (1) | DK2035368T3 (da) |
| ES (1) | ES2542980T3 (da) |
| HR (1) | HRP20150738T1 (da) |
| HU (1) | HUE026917T2 (da) |
| IT (1) | ITMI20061297A1 (da) |
| PL (1) | PL2035368T3 (da) |
| PT (1) | PT2035368E (da) |
| SI (1) | SI2035368T1 (da) |
| WO (1) | WO2008004044A1 (da) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101160281A (zh) | 2005-04-06 | 2008-04-09 | 特瓦制药工业有限公司 | 结晶形态的普瑞巴林 |
| US7488846B2 (en) | 2005-04-11 | 2009-02-10 | Teva Pharmaceuical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
| DE602006017995D1 (de) | 2005-05-10 | 2010-12-16 | Teva Pharma | Verfahren zur herstellung von pregabalin und salzen daraus |
| MX2007000525A (es) | 2005-05-10 | 2007-03-28 | Teva Pharma | Pregabalina libre de acido isobutilglutarico y un proceso para la preparacion de ella. |
| EP1879854B1 (en) | 2005-05-10 | 2011-09-07 | Teva Pharmaceutical Industries Ltd | Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid |
| WO2007035890A1 (en) | 2005-09-19 | 2007-03-29 | Teva Pharmaceutical Industries Ltd. | An asymmetric synthesis of ( s ) - ( + ) -3- (aminomethyl) -5-methylhexanoic acid |
| US7462738B2 (en) | 2006-05-24 | 2008-12-09 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of R-(+)-3-(carbamoyl methyl)-5-methylhexanoic acid and salts thereof |
| MX2008014759A (es) | 2007-03-22 | 2009-03-09 | Teva Pharma | Sintesis del acido (s)-(+)-3-(aminometil)-5-metil hexanoico. |
| WO2009147687A2 (en) * | 2008-06-03 | 2009-12-10 | Shodhana Laboratories Limited | An improved process for the separation of enantiomerically pure compounds |
| WO2014080345A2 (en) * | 2012-11-20 | 2014-05-30 | Shasun Pharmaceuticals Limited | Improved process for the preparation of pregabalin |
| CN103626668B (zh) * | 2013-11-07 | 2015-05-20 | 河北爱弗特精细化工有限责任公司 | 一种s-构型普瑞巴林的化学拆分制备方法 |
| CN104356016B (zh) * | 2014-10-24 | 2019-08-23 | 浙江华海药业股份有限公司 | 一种用回收制备3-异丁基戊二酸单酰胺的方法 |
| CN104710320A (zh) * | 2015-03-30 | 2015-06-17 | 浙江华海药业股份有限公司 | 一种制备普瑞巴林的方法 |
| CN105152954B (zh) * | 2015-07-22 | 2020-12-08 | 浙江华海药业股份有限公司 | 一种无溶剂回收3-异丁基戊二酸单酰胺的方法 |
| CN109678737B (zh) * | 2019-02-18 | 2021-12-24 | 常州制药厂有限公司 | 一种普瑞巴林的制备方法 |
| CN112745240A (zh) * | 2021-01-19 | 2021-05-04 | 宁波酶赛生物工程有限公司 | 一种高选择性的普瑞巴林中间体的重结晶方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5829719A (ja) * | 1981-08-14 | 1983-02-22 | Hiroyuki Nohira | 光学活性フエニルグリシノ−ルを用いるキラルカルボン酸の光学分割法 |
| JPS58183669A (ja) * | 1982-04-19 | 1983-10-26 | Teikoku Chem Ind Corp Ltd | 光学活性なプロピオン酸誘導体の製造方法 |
| JPS6013736A (ja) * | 1983-07-01 | 1985-01-24 | Hiroyuki Nohira | （±）−２−クロロプロピオン酸の光学分割法 |
| CA2023954C (en) * | 1989-10-17 | 1999-05-04 | Hiroyuki Nohira | Process for the optical resolution of 2-(3-benzoyl) phenylpropionic acid |
| JPH0753505A (ja) * | 1992-10-01 | 1995-02-28 | Hokuriku Seiyaku Co Ltd | ベンゼンスルホンアミド誘導体及びその用途 |
| US5616793A (en) * | 1995-06-02 | 1997-04-01 | Warner-Lambert Company | Methods of making (S)-3-(aminomethyl)-5-methylhexanoic acid |
| SE9904415D0 (sv) * | 1999-12-03 | 1999-12-03 | Astra Ab | New process |
| CN1203044C (zh) * | 2000-06-28 | 2005-05-25 | 大正制药株式会社 | 中间体及使用该中间体制备含氟羧酸衍生物的方法 |
| JP4319847B2 (ja) * | 2002-02-13 | 2009-08-26 | 第一三共株式会社 | （１ｓ，２ｓ）−２−フルオロシクロプロパンカルボン酸誘導体の製造方法 |
| US7501528B2 (en) * | 2005-03-15 | 2009-03-10 | Hoffmann-La Roche Inc. | Method for preparing enantiomerically pure 4-pyrrolidino phenylbenzyl ether derivatives |
-
2006
- 2006-07-04 IT IT001297A patent/ITMI20061297A1/it unknown
-
2007
- 2007-06-06 SI SI200731676T patent/SI2035368T1/sl unknown
- 2007-06-06 HU HUE07766518A patent/HUE026917T2/en unknown
- 2007-06-06 ES ES07766518.0T patent/ES2542980T3/es active Active
- 2007-06-06 JP JP2009517463A patent/JP5202519B2/ja not_active Expired - Fee Related
- 2007-06-06 EP EP07766518.0A patent/EP2035368B1/en active Active
- 2007-06-06 CA CA2656122A patent/CA2656122C/en not_active Expired - Fee Related
- 2007-06-06 CN CN2007800245632A patent/CN101500985B/zh not_active Expired - Fee Related
- 2007-06-06 US US12/306,980 patent/US8563775B2/en not_active Expired - Fee Related
- 2007-06-06 DK DK07766518.0T patent/DK2035368T3/da active
- 2007-06-06 PT PT77665180T patent/PT2035368E/pt unknown
- 2007-06-06 PL PL07766518T patent/PL2035368T3/pl unknown
- 2007-06-06 WO PCT/IB2007/001514 patent/WO2008004044A1/en active Application Filing
-
2015
- 2015-07-07 HR HRP20150738TT patent/HRP20150738T1/hr unknown
- 2015-07-10 CY CY20151100604T patent/CY1116498T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008004044A1 (en) | 2008-01-10 |
| PT2035368E (pt) | 2015-09-01 |
| SI2035368T1 (sl) | 2015-08-31 |
| CN101500985A (zh) | 2009-08-05 |
| HUE026917T2 (en) | 2016-08-29 |
| CA2656122C (en) | 2015-05-05 |
| CA2656122A1 (en) | 2008-01-10 |
| EP2035368A1 (en) | 2009-03-18 |
| JP5202519B2 (ja) | 2013-06-05 |
| EP2035368B1 (en) | 2015-05-27 |
| ITMI20061297A1 (it) | 2008-01-05 |
| CN101500985B (zh) | 2013-04-03 |
| PL2035368T3 (pl) | 2015-10-30 |
| HRP20150738T1 (hr) | 2015-08-14 |
| US20090192331A1 (en) | 2009-07-30 |
| CY1116498T1 (el) | 2017-03-15 |
| US8563775B2 (en) | 2013-10-22 |
| JP2009542615A (ja) | 2009-12-03 |
| ES2542980T3 (es) | 2015-08-13 |
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