PL2626428T3 - Sposób syntezy enzymatycznej kwasu (7S)-3,4-dimetoksybicyklo[4.2.0]okta-1,3,5-trien-7-karboksylowego lub jego estrów i zastosowania do syntezy iwabradyny i jej soli - Google Patents
Sposób syntezy enzymatycznej kwasu (7S)-3,4-dimetoksybicyklo[4.2.0]okta-1,3,5-trien-7-karboksylowego lub jego estrów i zastosowania do syntezy iwabradyny i jej soliInfo
- Publication number
- PL2626428T3 PL2626428T3 PL13154505T PL13154505T PL2626428T3 PL 2626428 T3 PL2626428 T3 PL 2626428T3 PL 13154505 T PL13154505 T PL 13154505T PL 13154505 T PL13154505 T PL 13154505T PL 2626428 T3 PL2626428 T3 PL 2626428T3
- Authority
- PL
- Poland
- Prior art keywords
- synthesis
- dimethoxybicyclo
- ivabradine
- triene
- octa
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title 2
- 238000003786 synthesis reaction Methods 0.000 title 2
- IHPWCJZOCLQJPX-QMMMGPOBSA-N (7s)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC2=C1[C@@H](C(O)=O)C2 IHPWCJZOCLQJPX-QMMMGPOBSA-N 0.000 title 1
- 230000002255 enzymatic effect Effects 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- ACRHBAYQBXXRTO-OAQYLSRUSA-N ivabradine Chemical compound C1CC2=CC(OC)=C(OC)C=C2CC(=O)N1CCCN(C)C[C@H]1CC2=C1C=C(OC)C(OC)=C2 ACRHBAYQBXXRTO-OAQYLSRUSA-N 0.000 title 1
- 229960003825 ivabradine Drugs 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 title 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/04—Saturated compounds having a carboxyl group bound to a three or four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P23/00—Preparation of compounds containing a cyclohexene ring having an unsaturated side chain containing at least ten carbon atoms bound by conjugated double bonds, e.g. carotenes
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/06—One of the condensed rings being a six-membered aromatic ring the other ring being four-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1251195A FR2986804A1 (fr) | 2012-02-09 | 2012-02-09 | Procede de synthese enzymatique de l'acide (7s) 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene 7-carboxylique ou de ses esters, et application a la synthese de l'ivabradine et de ses sels |
| EP13154505.5A EP2626428B1 (fr) | 2012-02-09 | 2013-02-08 | Procédé de synthèse enzymatique de l'acide (7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carboxylique ou de ses esters, et application à la synthèse de l'ivabradine et de ses sels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL2626428T3 true PL2626428T3 (pl) | 2015-10-30 |
Family
ID=47631378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL13154505T PL2626428T3 (pl) | 2012-02-09 | 2013-02-08 | Sposób syntezy enzymatycznej kwasu (7S)-3,4-dimetoksybicyklo[4.2.0]okta-1,3,5-trien-7-karboksylowego lub jego estrów i zastosowania do syntezy iwabradyny i jej soli |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US9506095B2 (pl) |
| EP (1) | EP2626428B1 (pl) |
| JP (1) | JP5764151B2 (pl) |
| KR (1) | KR101463787B1 (pl) |
| CN (1) | CN103243146A (pl) |
| AR (1) | AR089927A1 (pl) |
| AU (2) | AU2013200482A1 (pl) |
| BR (1) | BR102013003214A2 (pl) |
| CA (1) | CA2805831C (pl) |
| CY (1) | CY1116477T1 (pl) |
| DK (1) | DK2626428T3 (pl) |
| EA (1) | EA024316B1 (pl) |
| ES (1) | ES2546102T3 (pl) |
| FR (1) | FR2986804A1 (pl) |
| GE (1) | GEP20156235B (pl) |
| HR (1) | HRP20150872T1 (pl) |
| HU (1) | HUE026805T2 (pl) |
| JO (1) | JO3054B1 (pl) |
| MA (1) | MA34503B1 (pl) |
| MD (1) | MD4467C1 (pl) |
| MX (1) | MX341712B (pl) |
| PL (1) | PL2626428T3 (pl) |
| PT (1) | PT2626428E (pl) |
| RS (1) | RS54076B1 (pl) |
| SA (1) | SA113340275B1 (pl) |
| SG (1) | SG193081A1 (pl) |
| SI (1) | SI2626428T1 (pl) |
| TW (1) | TWI467019B (pl) |
| UA (1) | UA115765C2 (pl) |
| UY (1) | UY34611A (pl) |
| WO (1) | WO2013117869A2 (pl) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2986804A1 (fr) * | 2012-02-09 | 2013-08-16 | Servier Lab | Procede de synthese enzymatique de l'acide (7s) 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene 7-carboxylique ou de ses esters, et application a la synthese de l'ivabradine et de ses sels |
| EP3101010A1 (en) | 2015-06-03 | 2016-12-07 | Urquima S.A. | New method for the preparation of highly pure ivabradine base and salts thereof |
| CN113387791B (zh) * | 2021-03-05 | 2022-08-02 | 株洲壹诺生物技术有限公司 | 一种盐酸伊伐布雷定关键中间体的合成方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0319024B1 (en) * | 1987-12-03 | 1994-10-26 | Sumitomo Chemical Company, Limited | Process for producing optically active alpha-isopropyl-p-chlorophenylacetic acid |
| US5089637A (en) * | 1990-03-21 | 1992-02-18 | Pfizer Inc. | Process and intermediates for 2r-benzyl-chroman-6-carbaldehyde |
| FR2681862B1 (fr) * | 1991-09-27 | 1993-11-12 | Adir Cie | Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent. |
| CA2132411A1 (en) * | 1994-09-19 | 1996-03-20 | Michael Trani | Enzymatic esterification of long-chain racemic acids and alcohols |
| CN1246157A (zh) * | 1996-12-27 | 2000-03-01 | 史密丝克莱恩比彻姆有限公司 | 用脂酶进行苯并二氮杂䓬－乙酸酯的酶拆分 |
| DE69914458T2 (de) * | 1998-02-17 | 2004-10-28 | G.D. Searle & Co., Chicago | Verfahren zur enzymatischen auflösung von laktamen |
| US20060141591A1 (en) * | 2003-06-04 | 2006-06-29 | Youichi Kyuuko | Method for producing optically active chroman-carboxylate |
| GB0314260D0 (en) * | 2003-06-19 | 2003-07-23 | Astrazeneca Ab | Therapeutic agents |
| FR2868777B1 (fr) * | 2004-04-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| FR2870537A1 (fr) * | 2004-05-19 | 2005-11-25 | Servier Lab | Nouveau procede de synthese du (1s)-4,5-dimethoxy-1-(methyl aminomethyl-)-benzocyclobutane et de ses sels d'addition, et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable |
| GB0607911D0 (en) * | 2006-04-21 | 2006-05-31 | Ineos Fluor Holdings Ltd | Process |
| US20100165918A1 (en) * | 2006-08-23 | 2010-07-01 | Tsukasa Kobayashi | Mobile communication system, radio network controller, cellular and locating cell display method for use therewith |
| CN101434552B (zh) * | 2007-11-16 | 2012-05-23 | 江苏恒瑞医药股份有限公司 | 4,5-二甲氧基-1-(甲基氨基甲基)-苯并环丁烷的拆分 |
| FR2933975B1 (fr) * | 2008-07-17 | 2011-02-18 | Servier Lab | Nouveau procede de preparation de benzocyclobutenes fonctionnalises,et application a la synthese de l'ivabradine et de ses sels d'addition a un acide pharmaceutiquement acceptable. |
| FR2935381B1 (fr) * | 2008-08-29 | 2010-12-17 | Servier Lab | Nouveau procede de resolution des enantiomerees du (3,4-dimethoxy-bicyclo°4.2.0!octa-1,3,5-trien-7-yl)nitrile et application a la synthese de l'ivabradine |
| WO2010050499A1 (ja) * | 2008-10-29 | 2010-05-06 | 三菱瓦斯化学株式会社 | 光学活性有機カルボン酸の製造方法 |
| HUP1000245A2 (en) * | 2010-05-07 | 2011-11-28 | Richter Gedeon Nyrt | Industrial process for the production ivabradin salts |
| FR2986804A1 (fr) * | 2012-02-09 | 2013-08-16 | Servier Lab | Procede de synthese enzymatique de l'acide (7s) 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene 7-carboxylique ou de ses esters, et application a la synthese de l'ivabradine et de ses sels |
-
2012
- 2012-02-09 FR FR1251195A patent/FR2986804A1/fr not_active Withdrawn
-
2013
- 2013-01-27 JO JOP/2013/0030A patent/JO3054B1/ar active
- 2013-01-30 SG SG2013007331A patent/SG193081A1/en unknown
- 2013-01-30 AU AU2013200482A patent/AU2013200482A1/en not_active Abandoned
- 2013-02-01 UY UY0001034611A patent/UY34611A/es unknown
- 2013-02-05 US US13/759,382 patent/US9506095B2/en not_active Expired - Fee Related
- 2013-02-06 UA UAA201301422A patent/UA115765C2/uk unknown
- 2013-02-06 MX MX2013001458A patent/MX341712B/es active IP Right Grant
- 2013-02-06 SA SA113340275A patent/SA113340275B1/ar unknown
- 2013-02-06 JP JP2013021114A patent/JP5764151B2/ja active Active
- 2013-02-07 AR ARP130100377A patent/AR089927A1/es unknown
- 2013-02-07 GE GEAP201312992A patent/GEP20156235B/en unknown
- 2013-02-07 MD MDA20130008A patent/MD4467C1/ro not_active IP Right Cessation
- 2013-02-07 KR KR1020130014061A patent/KR101463787B1/ko not_active Expired - Fee Related
- 2013-02-07 AU AU2013200646A patent/AU2013200646B2/en not_active Ceased
- 2013-02-07 CN CN2013100492641A patent/CN103243146A/zh active Pending
- 2013-02-07 CA CA2805831A patent/CA2805831C/fr not_active Expired - Fee Related
- 2013-02-08 SI SI201330060T patent/SI2626428T1/sl unknown
- 2013-02-08 MA MA35650A patent/MA34503B1/fr unknown
- 2013-02-08 PT PT131545055T patent/PT2626428E/pt unknown
- 2013-02-08 BR BR102013003214A patent/BR102013003214A2/pt not_active Application Discontinuation
- 2013-02-08 WO PCT/FR2013/050265 patent/WO2013117869A2/fr not_active Ceased
- 2013-02-08 TW TW102105037A patent/TWI467019B/zh not_active IP Right Cessation
- 2013-02-08 HU HUE13154505A patent/HUE026805T2/en unknown
- 2013-02-08 EA EA201300100A patent/EA024316B1/ru not_active IP Right Cessation
- 2013-02-08 EP EP13154505.5A patent/EP2626428B1/fr active Active
- 2013-02-08 RS RS20150434A patent/RS54076B1/sr unknown
- 2013-02-08 ES ES13154505.5T patent/ES2546102T3/es active Active
- 2013-02-08 DK DK13154505.5T patent/DK2626428T3/en active
- 2013-02-08 PL PL13154505T patent/PL2626428T3/pl unknown
-
2015
- 2015-07-10 CY CY20151100602T patent/CY1116477T1/el unknown
- 2015-08-17 HR HRP20150872TT patent/HRP20150872T1/hr unknown
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