EA201300100A2 - Способ ферментативного синтеза (7s)-3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-карбоновой кислоты или ее сложных эфиров и применение для синтеза ивабрадина и его соли - Google Patents

Способ ферментативного синтеза (7s)-3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-карбоновой кислоты или ее сложных эфиров и применение для синтеза ивабрадина и его соли

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Publication number
EA201300100A2
EA201300100A2 EA201300100A EA201300100A EA201300100A2 EA 201300100 A2 EA201300100 A2 EA 201300100A2 EA 201300100 A EA201300100 A EA 201300100A EA 201300100 A EA201300100 A EA 201300100A EA 201300100 A2 EA201300100 A2 EA 201300100A2
Authority
EA
Eurasian Patent Office
Prior art keywords
synthesis
ivabradine
application
dimetoxybicyclo
trien
Prior art date
Application number
EA201300100A
Other languages
English (en)
Other versions
EA201300100A3 (ru
EA024316B1 (ru
Inventor
Сандрине Педрагоса-Моро
Франсуа Лефулон
Original Assignee
Ле Лаборатуар Сервье
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ле Лаборатуар Сервье filed Critical Ле Лаборатуар Сервье
Publication of EA201300100A2 publication Critical patent/EA201300100A2/ru
Publication of EA201300100A3 publication Critical patent/EA201300100A3/ru
Publication of EA024316B1 publication Critical patent/EA024316B1/ru

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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
    • 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)
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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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    • 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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    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
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    • C07B2200/07—Optical isomers
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    • 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
    • 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)
    • 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

Abstract

Способ ферментативного синтеза соединения формулы (I)где Rпредставляет собой атом водорода или алкильную группу. Применение для синтеза ивабрадина и его солей присоединения с фармацевтически приемлемой кислотой.
EA201300100A 2012-02-09 2013-02-08 Способ ферментативного синтеза (7s)-3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-карбоновой кислоты или ее сложных эфиров и применение для синтеза ивабрадина и его соли EA024316B1 (ru)

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
EA201300100A2 true EA201300100A2 (ru) 2013-08-30
EA201300100A3 EA201300100A3 (ru) 2013-10-30
EA024316B1 EA024316B1 (ru) 2016-09-30

Family

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Application Number Title Priority Date Filing Date
EA201300100A EA024316B1 (ru) 2012-02-09 2013-02-08 Способ ферментативного синтеза (7s)-3,4-диметоксибицикло[4.2.0]окта-1,3,5-триен-7-карбоновой кислоты или ее сложных эфиров и применение для синтеза ивабрадина и его соли

Country Status (31)

Country Link
US (1) US9506095B2 (ru)
EP (1) EP2626428B1 (ru)
JP (1) JP5764151B2 (ru)
KR (1) KR101463787B1 (ru)
CN (1) CN103243146A (ru)
AR (1) AR089927A1 (ru)
AU (2) AU2013200482A1 (ru)
BR (1) BR102013003214A2 (ru)
CA (1) CA2805831C (ru)
CY (1) CY1116477T1 (ru)
DK (1) DK2626428T3 (ru)
EA (1) EA024316B1 (ru)
ES (1) ES2546102T3 (ru)
FR (1) FR2986804A1 (ru)
GE (1) GEP20156235B (ru)
HR (1) HRP20150872T1 (ru)
HU (1) HUE026805T2 (ru)
JO (1) JO3054B1 (ru)
MA (1) MA34503B1 (ru)
MD (1) MD4467C1 (ru)
MX (1) MX341712B (ru)
PL (1) PL2626428T3 (ru)
PT (1) PT2626428E (ru)
RS (1) RS54076B1 (ru)
SA (1) SA113340275B1 (ru)
SG (1) SG193081A1 (ru)
SI (1) SI2626428T1 (ru)
TW (1) TWI467019B (ru)
UA (1) UA115765C2 (ru)
UY (1) UY34611A (ru)
WO (1) WO2013117869A2 (ru)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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

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DE3851942T2 (de) * 1987-12-03 1995-02-23 Sumitomo Chemical Co Verfahren zur Herstellung von optisch aktiver alpha-Isopropyl-p-chlorophenylessigsäure.
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
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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
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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
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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.
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Also Published As

Publication number Publication date
UA115765C2 (uk) 2017-12-26
SI2626428T1 (sl) 2015-10-30
EA201300100A3 (ru) 2013-10-30
TWI467019B (zh) 2015-01-01
SG193081A1 (en) 2013-09-30
AU2013200646B2 (en) 2014-12-18
MX341712B (es) 2016-08-31
MD20130008A2 (en) 2013-07-31
MX2013001458A (es) 2013-08-28
MD4467B1 (ru) 2017-02-28
EP2626428A3 (fr) 2013-10-30
AR089927A1 (es) 2014-10-01
MA34503B1 (fr) 2013-09-02
JP5764151B2 (ja) 2015-08-12
AU2013200646A1 (en) 2013-08-29
PL2626428T3 (pl) 2015-10-30
EP2626428B1 (fr) 2015-05-27
US9506095B2 (en) 2016-11-29
JP2013162788A (ja) 2013-08-22
SA113340275B1 (ar) 2015-08-18
CA2805831C (fr) 2015-11-24
CN103243146A (zh) 2013-08-14
GEP20156235B (en) 2015-01-26
RS54076B1 (en) 2015-10-30
TW201333206A (zh) 2013-08-16
HRP20150872T1 (hr) 2015-09-25
PT2626428E (pt) 2015-08-21
KR101463787B1 (ko) 2014-11-20
MD4467C1 (ru) 2017-09-30
FR2986804A1 (fr) 2013-08-16
WO2013117869A3 (fr) 2013-11-14
CA2805831A1 (fr) 2013-08-09
US20130210091A1 (en) 2013-08-15
JO3054B1 (ar) 2017-03-15
WO2013117869A2 (fr) 2013-08-15
ES2546102T3 (es) 2015-09-18
DK2626428T3 (en) 2015-08-31
EP2626428A2 (fr) 2013-08-14
CY1116477T1 (el) 2017-03-15
EA024316B1 (ru) 2016-09-30
UY34611A (es) 2013-09-30
BR102013003214A2 (pt) 2016-04-19
AU2013200482A1 (en) 2013-08-29
KR20130092483A (ko) 2013-08-20
HUE026805T2 (en) 2016-07-28

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