MX2013001458A - Procedimiento de sintesis enzimatica del acido (7,s)-3,4-dimetoxibiociclo [4.2.0] octa-1,3,5-trien-7-carboxilico o de sus esteres, y aplicación a la sintesis de la ivabradina y de sus sales. - Google Patents
Procedimiento de sintesis enzimatica del acido (7,s)-3,4-dimetoxibiociclo [4.2.0] octa-1,3,5-trien-7-carboxilico o de sus esteres, y aplicación a la sintesis de la ivabradina y de sus sales.Info
- Publication number
- MX2013001458A MX2013001458A MX2013001458A MX2013001458A MX2013001458A MX 2013001458 A MX2013001458 A MX 2013001458A MX 2013001458 A MX2013001458 A MX 2013001458A MX 2013001458 A MX2013001458 A MX 2013001458A MX 2013001458 A MX2013001458 A MX 2013001458A
- Authority
- MX
- Mexico
- Prior art keywords
- synthesis
- ivabradine
- dimethoxybicyclo
- triene
- octa
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 4
- 238000003786 synthesis reaction Methods 0.000 title abstract 4
- 230000002255 enzymatic effect Effects 0.000 title abstract 2
- 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 abstract 2
- 229960003825 ivabradine Drugs 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 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
- 150000002148 esters Chemical class 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- 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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- C07—ORGANIC CHEMISTRY
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- 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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- 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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- 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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- 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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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- 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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- 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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- 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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- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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- C07B2200/07—Optical isomers
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- 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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- 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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- 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
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- 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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (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
Procedimiento de síntesis enzimática del compuesto de fórmula (I): (ver Fórmula) en la que R1 representa un átomo de hidrógeno o un grupo alquilo. Aplicación a la síntesis de la ivabradina y de sus sales de adición a un ácido farmacéuticamente aceptable.
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 (2)
| Publication Number | Publication Date |
|---|---|
| MX2013001458A true MX2013001458A (es) | 2013-08-28 |
| MX341712B MX341712B (es) | 2016-08-31 |
Family
ID=47631378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2013001458A MX341712B (es) | 2012-02-09 | 2013-02-06 | Procedimiento de síntesis enzimática del ácido (7,s)-3,4-dimetoxibiciclo [4.2.0] octa-1,3,5-trien-7-carboxílico o de sus ésteres, y aplicación a la síntesis de la ivabradina y de sus sales. |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US9506095B2 (es) |
| EP (1) | EP2626428B1 (es) |
| JP (1) | JP5764151B2 (es) |
| KR (1) | KR101463787B1 (es) |
| CN (1) | CN103243146A (es) |
| AR (1) | AR089927A1 (es) |
| AU (2) | AU2013200482A1 (es) |
| BR (1) | BR102013003214A2 (es) |
| CA (1) | CA2805831C (es) |
| CY (1) | CY1116477T1 (es) |
| DK (1) | DK2626428T3 (es) |
| EA (1) | EA024316B1 (es) |
| ES (1) | ES2546102T3 (es) |
| FR (1) | FR2986804A1 (es) |
| GE (1) | GEP20156235B (es) |
| HR (1) | HRP20150872T1 (es) |
| HU (1) | HUE026805T2 (es) |
| JO (1) | JO3054B1 (es) |
| MA (1) | MA34503B1 (es) |
| MD (1) | MD4467C1 (es) |
| MX (1) | MX341712B (es) |
| PL (1) | PL2626428T3 (es) |
| PT (1) | PT2626428E (es) |
| RS (1) | RS54076B1 (es) |
| SA (1) | SA113340275B1 (es) |
| SG (1) | SG193081A1 (es) |
| SI (1) | SI2626428T1 (es) |
| TW (1) | TWI467019B (es) |
| UA (1) | UA115765C2 (es) |
| UY (1) | UY34611A (es) |
| WO (1) | WO2013117869A2 (es) |
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 |
| AU730064B2 (en) * | 1996-12-27 | 2001-02-22 | Smithkline Beecham Plc | Enzymatic resolution of benzodiazepine-acetic acids from esters with a lipase |
| DK1054996T3 (da) * | 1998-02-17 | 2004-05-24 | Searle & Co | Fremgangsmåde til den enzymatiske adskillelse af lactamer |
| 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 |
| EP2059061B1 (en) * | 2006-08-23 | 2014-07-23 | NEC Corporation | Mobile communication system, radio network control device, mobile telephone, and cell display method |
| 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 |
| EP2351729B1 (en) * | 2008-10-29 | 2014-01-22 | 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 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 JP JP2013021114A patent/JP5764151B2/ja active Active
- 2013-02-06 MX MX2013001458A patent/MX341712B/es active IP Right Grant
- 2013-02-06 UA UAA201301422A patent/UA115765C2/uk unknown
- 2013-02-06 SA SA113340275A patent/SA113340275B1/ar 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 KR KR1020130014061A patent/KR101463787B1/ko not_active Expired - Fee Related
- 2013-02-07 MD MDA20130008A patent/MD4467C1/ro not_active IP Right Cessation
- 2013-02-07 CN CN2013100492641A patent/CN103243146A/zh active Pending
- 2013-02-07 AU AU2013200646A patent/AU2013200646B2/en not_active Ceased
- 2013-02-07 GE GEAP201312992A patent/GEP20156235B/en unknown
- 2013-02-08 EA EA201300100A patent/EA024316B1/ru not_active IP Right Cessation
- 2013-02-08 SI SI201330060T patent/SI2626428T1/sl unknown
- 2013-02-08 WO PCT/FR2013/050265 patent/WO2013117869A2/fr not_active Ceased
- 2013-02-08 EP EP13154505.5A patent/EP2626428B1/fr active Active
- 2013-02-08 HU HUE13154505A patent/HUE026805T2/en unknown
- 2013-02-08 DK DK13154505.5T patent/DK2626428T3/en active
- 2013-02-08 PL PL13154505T patent/PL2626428T3/pl unknown
- 2013-02-08 RS RS20150434A patent/RS54076B1/sr unknown
- 2013-02-08 MA MA35650A patent/MA34503B1/fr unknown
- 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 BR BR102013003214A patent/BR102013003214A2/pt not_active Application Discontinuation
- 2013-02-08 PT PT131545055T patent/PT2626428E/pt unknown
-
2015
- 2015-07-10 CY CY20151100602T patent/CY1116477T1/el unknown
- 2015-08-17 HR HRP20150872TT patent/HRP20150872T1/hr unknown
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