PE20130224A1 - Proceso para la preparacion de calcobutrol - Google Patents
Proceso para la preparacion de calcobutrolInfo
- Publication number
- PE20130224A1 PE20130224A1 PE2012000612A PE2012000612A PE20130224A1 PE 20130224 A1 PE20130224 A1 PE 20130224A1 PE 2012000612 A PE2012000612 A PE 2012000612A PE 2012000612 A PE2012000612 A PE 2012000612A PE 20130224 A1 PE20130224 A1 PE 20130224A1
- Authority
- PE
- Peru
- Prior art keywords
- acid
- calcobutrol
- triacetico
- hydroximethyl
- dihydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- GCLKDXFGQNCFQW-CTHHTMFSSA-L calcium 2-[4,10-bis(carboxylatomethyl)-7-[(2R,3S)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetrazacyclododec-1-yl]acetate hydron Chemical compound [H+].[Ca+2].OC[C@@H](O)[C@@H](CO)N1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 GCLKDXFGQNCFQW-CTHHTMFSSA-L 0.000 title abstract 3
- 229950006450 calcobutrol Drugs 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 abstract 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical class [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 abstract 2
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 abstract 2
- 239000003456 ion exchange resin Substances 0.000 abstract 2
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 2
- ZPDFIIGFYAHNSK-CTHHTMFSSA-K 2-[4,10-bis(carboxylatomethyl)-7-[(2r,3s)-1,3,4-trihydroxybutan-2-yl]-1,4,7,10-tetrazacyclododec-1-yl]acetate;gadolinium(3+) Chemical compound [Gd+3].OC[C@@H](O)[C@@H](CO)N1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 ZPDFIIGFYAHNSK-CTHHTMFSSA-K 0.000 abstract 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- 229910052688 Gadolinium Inorganic materials 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 239000000920 calcium hydroxide Substances 0.000 abstract 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 1
- 229910001424 calcium ion Inorganic materials 0.000 abstract 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000292 calcium oxide Substances 0.000 abstract 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000004108 freeze drying Methods 0.000 abstract 1
- 229960003411 gadobutrol Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/04—Calcium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Radiology & Medical Imaging (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Abstract
SE REFIERE A UN PROCESO PARA LA PREPARACION DEL CALCOBUTROL (ACIDO 10-(2,3-DIHIDROXI-1-(HIDROXIMETIL)PROPIL)-1,4,7,10-TETRAAZACICLODECANO-1,4,7-TRIACETICO) QUE COMPRENDE: A) DESACOMPLEJAR EL COMPLEJO CON GADOLINIO DEL ACIDO 10-(2,3-DIHIDROXI-1-(HIDROXIMETIL)PROPIL)-1,4,7,10TETRAAZACICLODECANO-1,4,7-TRIACETICO (GADOBUTROL).CON UN AGENTE DESCOMPLEJANTE TAL COMO ACIDO OXALICO, DONDE LA REACCION SE LLEVA A CABO EN AGUA A TEMPERATURA ENTRE 75 Y 100C; B) SEPARAR LA SAL DE GADOLINIO QUE PRECIPITA; C) UNIR AL LIGANDO LIBRE EN LA SOLUCION QUE SE OBTIENE COMO RESULTADO DE B) A UNA RESINA DE INTERCAMBIO IONICO ACIDA; D) ELUIR DICHA RESINA CON UNA SOLUCION ALCALINA ACUOSA, SELECCIONADA DE AMONIACO, DIMETILAMINA, METILAMINA, ENTRE OTROS; E) TRATAR EL ELUATO CON RESINA DE INTERCAMBIO IONICO ACIDA, Y AISLAR POR LIOFILIZACION EL PRODUCTO OBTENIDO; F) COMPLEJAR EL LIGANDO CON IONES CA+2 Y CRISTALIZARLO, DONDE LA FUENTE DE ION CALCIO ES CARBONATO, OXIDO O HIDROXIDO DE CALCIO. LAS VENTAJAS DE DICHO PROCESO SE CARACTERIZAN POR SER ALTAMENTE REPRODUCIBLE Y FACTIBLE. DICHO PROCESO ES UTIL EN OBTENER EL CALCOBUTROL DE ALTA CALIDAD
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009053171A DE102009053171B4 (de) | 2009-11-04 | 2009-11-04 | Verfahren zur Herstellung des Calcium-Komplexes von Dihydroxy-hydroxy-methylpropyl-tetraazacyclododecan-triessigsäure (Calcobutrol) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20130224A1 true PE20130224A1 (es) | 2013-03-06 |
Family
ID=43297060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2012000612A PE20130224A1 (es) | 2009-11-04 | 2010-11-02 | Proceso para la preparacion de calcobutrol |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US9447053B2 (es) |
| EP (2) | EP2496562B1 (es) |
| JP (1) | JP5733800B2 (es) |
| KR (3) | KR20120093388A (es) |
| CN (1) | CN102164901B (es) |
| AR (1) | AR078906A1 (es) |
| AU (1) | AU2010317166C1 (es) |
| BR (1) | BR112012010320B1 (es) |
| CA (1) | CA2777314C (es) |
| CL (1) | CL2012001172A1 (es) |
| CO (1) | CO6551758A2 (es) |
| CR (1) | CR20120235A (es) |
| CU (1) | CU24105B1 (es) |
| CY (1) | CY1115051T1 (es) |
| DE (1) | DE102009053171B4 (es) |
| DK (1) | DK2496562T3 (es) |
| DO (1) | DOP2012000126A (es) |
| EA (2) | EA201300789A1 (es) |
| EC (1) | ECSP12011866A (es) |
| ES (1) | ES2462970T3 (es) |
| HR (1) | HRP20140399T1 (es) |
| IL (1) | IL219012A0 (es) |
| MX (1) | MX2012005283A (es) |
| MY (1) | MY158421A (es) |
| NZ (2) | NZ599705A (es) |
| PE (1) | PE20130224A1 (es) |
| PH (1) | PH12012500891A1 (es) |
| PL (1) | PL2496562T3 (es) |
| PT (1) | PT2496562E (es) |
| RS (1) | RS53287B (es) |
| SI (1) | SI2496562T1 (es) |
| TW (1) | TWI473794B (es) |
| UY (1) | UY33002A (es) |
| WO (1) | WO2011054827A1 (es) |
| ZA (1) | ZA201202504B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2780599T3 (es) | 2011-04-21 | 2020-08-26 | Bayer Ip Gmbh | Preparación de gadobutrol de alta pureza |
| EP2786768A1 (en) | 2013-04-04 | 2014-10-08 | Agfa Healthcare | Process for preparing a material comprising a macrocyclic ligand and for producing a pharmaceutical formulation comprising said ligand with a lanthanide |
| KR101693400B1 (ko) | 2014-09-17 | 2017-01-05 | 에스티팜 주식회사 | 칼코부트롤의 제조방법 |
| KR101646211B1 (ko) * | 2014-11-12 | 2016-08-05 | (주)디아이테크 | 자기공명영상용 조영제의 제조방법 |
| EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
| CN105037288B (zh) * | 2015-07-23 | 2017-11-03 | 上海现代制药海门有限公司 | 一种布醇的制备方法 |
| CN106620726B (zh) * | 2015-10-29 | 2020-10-02 | 山东威智百科药业有限公司 | 一种钆布醇注射液及其制备方法 |
| CN106187930B (zh) * | 2016-07-12 | 2018-10-19 | 嘉实（湖南）医药科技有限公司 | 高纯度考布曲钙的制备方法 |
| HUE050553T2 (hu) * | 2016-09-27 | 2020-12-28 | Bayer Pharma AG | Eljárás A módosulatú kalkobutrol kristályos alakjának elõállítására |
| WO2018096082A1 (en) | 2016-11-28 | 2018-05-31 | Bayer Pharma Aktiengesellschaft | High relaxivity gadolinium chelate compounds for use in magnetic resonance imaging |
| CN109384737A (zh) * | 2017-08-04 | 2019-02-26 | 天津科伦药物研究有限公司 | 一种四氮杂环钇络合物及其制备方法和应用 |
| KR101971435B1 (ko) * | 2017-08-29 | 2019-04-24 | 주식회사 엔지켐생명과학 | 가도부트롤 중간체 및 이를 이용한 가도부트롤의 제조 방법 |
| KR20190088793A (ko) * | 2018-01-19 | 2019-07-29 | 주식회사 엔지켐생명과학 | 칼코부트롤의 제조방법 |
| EP3820853A4 (en) | 2018-07-10 | 2022-08-17 | Biophore India Pharmaceuticals Pvt. Ltd. | PROCESS FOR THE PREPARATION OF 2,2',2''-(10-((2R,3S)-1,3,4-TRIHYDROXY BUTAN-2-YL)-1,4,7,10-TETRAAZACYCLODODECANE-1 ACID ,4,7-TRIYL) TRIACETIC AND ITS COMPLEXES |
| WO2020084504A1 (en) * | 2018-10-24 | 2020-04-30 | Biophore India Pharmaceuticals Pvt. Ltd | Novel process for the preparation of macrocyclic chelant 2,2',2''-(10-(2-hydroxypropyl)-1,4,7,10-tetra azacyclododecane-1,4,7-triyl) triacetic acid and it's complexes with paramagnetic metal ions |
| AU2019382881B2 (en) * | 2018-11-23 | 2025-06-12 | Bayer Aktiengesellschaft | Formulation of contrast media and process of preparation thereof |
| KR101979836B1 (ko) * | 2019-01-02 | 2019-05-21 | 동국생명과학 주식회사 | 칼코부트롤의 제조방법 |
| CN111039885B (zh) * | 2019-12-06 | 2021-03-05 | 广州康瑞泰药业有限公司 | 一种制备高纯度考布曲钙的方法 |
| US11667601B2 (en) | 2019-12-20 | 2023-06-06 | Bracco Imaging S.P.A. | Calcium BOPTA complex |
| KR20210112910A (ko) | 2020-03-06 | 2021-09-15 | 주식회사 엔지켐생명과학 | 가도부트롤 주사제 제조를 위한 부형제인 칼코부트롤의 제조 방법 |
| KR20210114742A (ko) * | 2020-03-11 | 2021-09-24 | 주식회사 엔지켐생명과학 | 칼테리돌의 제조방법 |
| CN114573522A (zh) * | 2020-11-30 | 2022-06-03 | 江苏恒瑞医药股份有限公司 | 一种考布曲钙的新晶型及其制备方法 |
| CN115779105B (zh) * | 2022-11-17 | 2025-05-27 | 华润双鹤药业股份有限公司 | 一种钆布醇注射液及其制备方法 |
| CN119143689B (zh) * | 2024-11-15 | 2025-05-30 | 苏州美诺医药科技有限公司 | 考布曲钙和其中间体的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3625417C2 (de) | 1986-07-28 | 1998-10-08 | Schering Ag | Tetraazacyclododecan-Derivate |
| DE3640708C2 (de) * | 1986-11-28 | 1995-05-18 | Schering Ag | Verbesserte metallhaltige Pharmazeutika |
| DE4009119A1 (de) | 1990-03-19 | 1991-09-26 | Schering Ag | 1,4,7,10-tetraazacyclododecan-butyltriole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| IE910955A1 (en) | 1990-03-23 | 1991-09-25 | Yamanouchi Europ Bv | Il-6 inhibiting compositions |
| DE4237943C2 (de) * | 1992-11-06 | 1997-10-23 | Schering Ag | Verfahren zur Herstellung von Metallkomplexen der N-beta-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,7,10-tetraazacyclododecan- und N-beta-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,8,11-tetraazacyclotetradecan-Derivate |
| DE4218744C2 (de) * | 1992-06-04 | 1997-11-06 | Schering Ag | Verfahren zur Herstellung von N-ß-Hxdroxyalkyl-tri-N-carboxylalkyl-1,4,7,10-tetraazacyclododecan- und N-ß-Hydroxyalkyl-tri-N-carboxyalkyl-1,4,8,11-tetraazacyclotetradecan-Derivaten und deren Metallkomplexe |
| IT1275426B (it) | 1995-05-16 | 1997-08-07 | Bracco Spa | Recupero del gadolinio e dei suoi agenti complessanti da soluzioni acquose contenenti i loro complessi |
| DE19724186C2 (de) * | 1997-06-02 | 2002-07-18 | Schering Ag | Verfahren zur Mono- und 1,7-Bis-N-ß-Hydroxyalkylierung von Cyclen und die entsprechenden N-ß-Hydroxyalkyl-1,4,7,10-tetraazacyclododecan-Li-Salz-Komplexe |
| IT1292130B1 (it) | 1997-06-11 | 1999-01-25 | Bracco Spa | Processo per la preparazione dell'acido 1,4,7,10-tetraazaciclododecan -1,4,7-triacetico e suoi derivati |
| IT1293778B1 (it) | 1997-07-25 | 1999-03-10 | Bracco Spa | 1,4,7,10-tetraazabiciclo(8.2.2.)tetradecan-2 one, sua preparazione e suo uso per la preparazione di tetraazamacrocicli |
| US9016221B2 (en) * | 2004-02-17 | 2015-04-28 | University Of Florida Research Foundation, Inc. | Surface topographies for non-toxic bioadhesion control |
| WO2011054480A1 (de) * | 2009-11-09 | 2011-05-12 | Bayer Schering Pharma Aktiengesellschaft | Gadobutrolherstellung mittels keramischer membran |
-
2009
- 2009-11-04 DE DE102009053171A patent/DE102009053171B4/de active Active
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2010
- 2010-11-02 SI SI201030597T patent/SI2496562T1/sl unknown
- 2010-11-02 CA CA2777314A patent/CA2777314C/en active Active
- 2010-11-02 NZ NZ599705A patent/NZ599705A/en unknown
- 2010-11-02 AU AU2010317166A patent/AU2010317166C1/en active Active
- 2010-11-02 RS RS20140225A patent/RS53287B/sr unknown
- 2010-11-02 JP JP2012537372A patent/JP5733800B2/ja active Active
- 2010-11-02 CU CU2012000072A patent/CU24105B1/es active IP Right Grant
- 2010-11-02 BR BR112012010320-2A patent/BR112012010320B1/pt active IP Right Grant
- 2010-11-02 KR KR1020127015861A patent/KR20120093388A/ko not_active Withdrawn
- 2010-11-02 EP EP10774202.5A patent/EP2496562B1/en active Active
- 2010-11-02 PE PE2012000612A patent/PE20130224A1/es active IP Right Grant
- 2010-11-02 KR KR1020117016891A patent/KR101251210B1/ko not_active Ceased
- 2010-11-02 EA EA201300789A patent/EA201300789A1/ru unknown
- 2010-11-02 ES ES10774202.5T patent/ES2462970T3/es active Active
- 2010-11-02 PL PL10774202T patent/PL2496562T3/pl unknown
- 2010-11-02 PH PH1/2012/500891A patent/PH12012500891A1/en unknown
- 2010-11-02 MY MYPI2012001942A patent/MY158421A/en unknown
- 2010-11-02 DK DK10774202.5T patent/DK2496562T3/da active
- 2010-11-02 PT PT107742025T patent/PT2496562E/pt unknown
- 2010-11-02 EP EP13151283.2A patent/EP2599777A1/en not_active Withdrawn
- 2010-11-02 KR KR1020107029604A patent/KR101057939B1/ko active Active
- 2010-11-02 WO PCT/EP2010/066655 patent/WO2011054827A1/en not_active Ceased
- 2010-11-02 CN CN201080002019.XA patent/CN102164901B/zh active Active
- 2010-11-02 NZ NZ612449A patent/NZ612449A/en unknown
- 2010-11-02 MX MX2012005283A patent/MX2012005283A/es active IP Right Grant
- 2010-11-02 US US13/508,198 patent/US9447053B2/en active Active
- 2010-11-02 EA EA201200652A patent/EA020161B9/ru not_active IP Right Cessation
- 2010-11-02 HR HRP20140399AT patent/HRP20140399T1/hr unknown
- 2010-11-04 TW TW99137984A patent/TWI473794B/zh active
- 2010-11-04 AR ARP100104075A patent/AR078906A1/es active IP Right Grant
- 2010-11-04 UY UY0001033002A patent/UY33002A/es not_active Application Discontinuation
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2012
- 2012-04-03 IL IL219012A patent/IL219012A0/en active IP Right Grant
- 2012-04-05 ZA ZA2012/02504A patent/ZA201202504B/en unknown
- 2012-05-04 CR CR20120235A patent/CR20120235A/es unknown
- 2012-05-04 CL CL2012001172A patent/CL2012001172A1/es unknown
- 2012-05-04 CO CO12073057A patent/CO6551758A2/es not_active Application Discontinuation
- 2012-05-04 DO DO2012000126A patent/DOP2012000126A/es unknown
- 2012-05-04 EC ECSP12011866 patent/ECSP12011866A/es unknown
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2014
- 2014-05-07 CY CY20141100325T patent/CY1115051T1/el unknown
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