MD4467B1 - Procedeu de sinteză enzimatică a acidului (7S)-3,4-dimetoxibiciclo[4.2.0]octa-1,3,5-triene-7-carboxilic sau a esterilor săi şi aplicarea lor în sinteza ivabradinei şi a sărurilor sale - Google Patents
Procedeu de sinteză enzimatică a acidului (7S)-3,4-dimetoxibiciclo[4.2.0]octa-1,3,5-triene-7-carboxilic sau a esterilor săi şi aplicarea lor în sinteza ivabradinei şi a sărurilor saleInfo
- Publication number
- MD4467B1 MD4467B1 MDA20130008A MD20130008A MD4467B1 MD 4467 B1 MD4467 B1 MD 4467B1 MD A20130008 A MDA20130008 A MD A20130008A MD 20130008 A MD20130008 A MD 20130008A MD 4467 B1 MD4467 B1 MD 4467B1
- Authority
- MD
- Moldova
- Prior art keywords
- synthesis
- dimethoxybicyclo
- ivabradine
- triene
- octa
- Prior art date
Links
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
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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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (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)
Abstract
Prezenta invenţie se referă la un procedeu de sinteză enzimatică a compusului cu formula (I):unde R1 reprezintă un atom de hidrogen sau o grupă alchil C1-C6, de preferinţă metil, precum şi la aplicarea acestuia în sinteza ivabradinei (3-{3-[{[(7S)-3,4-dimetoxibiciclo[4.2.0]octa-1,3,5-trien-7-il]metil}(metil)amino]propil}-7,8-dimetoxi-1,3,4,5-tetrahidro-2H-3-benzazepin-2-ona) cu formula (II):a sărurilor sale de adiţie cu acizi farmaceutic acceptabili şi a hidraţilor acestora.Utilizarea lipazelor Pseudomonas fluorescens şi Candida antarctica permite obţinerea compuşilor chirali - principalii intermediari în sinteza ingredientelor farmaceutic active - în excese enantiomerice înalte şi randamente bune.
Applications Claiming Priority (1)
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| MD20130008A2 MD20130008A2 (ro) | 2013-07-31 |
| MD4467B1 true MD4467B1 (ro) | 2017-02-28 |
| MD4467C1 MD4467C1 (ro) | 2017-09-30 |
Family
ID=47631378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20130008A MD4467C1 (ro) | 2012-02-09 | 2013-02-07 | Procedeu de sinteză enzimatică a acidului (7S)-3,4-dimetoxibiciclo[4.2.0]octa-1,3,5-trien-7-carboxilic sau a esterilor săi şi aplicarea lor în sinteza ivabradinei şi a sărurilor sale |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US9506095B2 (ro) |
| EP (1) | EP2626428B1 (ro) |
| JP (1) | JP5764151B2 (ro) |
| KR (1) | KR101463787B1 (ro) |
| CN (1) | CN103243146A (ro) |
| AR (1) | AR089927A1 (ro) |
| AU (2) | AU2013200482A1 (ro) |
| BR (1) | BR102013003214A2 (ro) |
| CA (1) | CA2805831C (ro) |
| CY (1) | CY1116477T1 (ro) |
| DK (1) | DK2626428T3 (ro) |
| EA (1) | EA024316B1 (ro) |
| ES (1) | ES2546102T3 (ro) |
| FR (1) | FR2986804A1 (ro) |
| GE (1) | GEP20156235B (ro) |
| HR (1) | HRP20150872T1 (ro) |
| HU (1) | HUE026805T2 (ro) |
| JO (1) | JO3054B1 (ro) |
| MA (1) | MA34503B1 (ro) |
| MD (1) | MD4467C1 (ro) |
| MX (1) | MX341712B (ro) |
| PL (1) | PL2626428T3 (ro) |
| PT (1) | PT2626428E (ro) |
| RS (1) | RS54076B1 (ro) |
| SA (1) | SA113340275B1 (ro) |
| SG (1) | SG193081A1 (ro) |
| SI (1) | SI2626428T1 (ro) |
| TW (1) | TWI467019B (ro) |
| UA (1) | UA115765C2 (ro) |
| UY (1) | UY34611A (ro) |
| WO (1) | WO2013117869A2 (ro) |
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 |
| PL334293A1 (en) * | 1996-12-27 | 2000-02-14 | Smithkline Beecham Plc | Enzymatic separation of benzodiazepinacetic esters by means of lipase |
| JP2003517266A (ja) * | 1998-02-17 | 2003-05-27 | ジー・ディー・サール・アンド・カンパニー | ラクタムの酵素分割方法 |
| JPWO2004108944A1 (ja) * | 2003-06-04 | 2006-07-20 | 三菱瓦斯化学株式会社 | 光学活性クロマンカルボン酸エステルの製造方法 |
| 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 |
| US20110251407A1 (en) * | 2008-10-29 | 2011-10-13 | Mitsubishi Gas Chemical Company, Inc. | Process for production of optically active organic carboxylic acid |
| 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 AU AU2013200482A patent/AU2013200482A1/en not_active Abandoned
- 2013-01-30 SG SG2013007331A patent/SG193081A1/en unknown
- 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 MX MX2013001458A patent/MX341712B/es active IP Right Grant
- 2013-02-06 UA UAA201301422A patent/UA115765C2/uk unknown
- 2013-02-06 JP JP2013021114A patent/JP5764151B2/ja active Active
- 2013-02-06 SA SA113340275A patent/SA113340275B1/ar unknown
- 2013-02-07 MD MDA20130008A patent/MD4467C1/ro not_active IP Right Cessation
- 2013-02-07 GE GEAP201312992A patent/GEP20156235B/en unknown
- 2013-02-07 CA CA2805831A patent/CA2805831C/fr not_active Expired - Fee Related
- 2013-02-07 AR ARP130100377A patent/AR089927A1/es unknown
- 2013-02-07 AU AU2013200646A patent/AU2013200646B2/en not_active Ceased
- 2013-02-07 CN CN2013100492641A patent/CN103243146A/zh active Pending
- 2013-02-07 KR KR1020130014061A patent/KR101463787B1/ko active IP Right Grant
- 2013-02-08 SI SI201330060T patent/SI2626428T1/sl unknown
- 2013-02-08 EA EA201300100A patent/EA024316B1/ru not_active IP Right Cessation
- 2013-02-08 TW TW102105037A patent/TWI467019B/zh not_active IP Right Cessation
- 2013-02-08 ES ES13154505.5T patent/ES2546102T3/es active Active
- 2013-02-08 RS RS20150434A patent/RS54076B1/en unknown
- 2013-02-08 EP EP13154505.5A patent/EP2626428B1/fr active Active
- 2013-02-08 PT PT131545055T patent/PT2626428E/pt unknown
- 2013-02-08 MA MA35650A patent/MA34503B1/fr unknown
- 2013-02-08 HU HUE13154505A patent/HUE026805T2/en unknown
- 2013-02-08 DK DK13154505.5T patent/DK2626428T3/en active
- 2013-02-08 BR BR102013003214A patent/BR102013003214A2/pt not_active Application Discontinuation
- 2013-02-08 PL PL13154505T patent/PL2626428T3/pl unknown
- 2013-02-08 WO PCT/FR2013/050265 patent/WO2013117869A2/fr active Application Filing
-
2015
- 2015-07-10 CY CY20151100602T patent/CY1116477T1/el unknown
- 2015-08-17 HR HRP20150872TT patent/HRP20150872T1/hr unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |