HRP20160766T1 - Postupak za proizvodnju ivabradina i intermedijera njegove sinteze - Google Patents

Postupak za proizvodnju ivabradina i intermedijera njegove sinteze Download PDF

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Publication number
HRP20160766T1
HRP20160766T1 HRP20160766TT HRP20160766T HRP20160766T1 HR P20160766 T1 HRP20160766 T1 HR P20160766T1 HR P20160766T T HRP20160766T T HR P20160766TT HR P20160766 T HRP20160766 T HR P20160766T HR P20160766 T1 HRP20160766 T1 HR P20160766T1
Authority
HR
Croatia
Prior art keywords
benzocyclobutane
ibuprofen
aminomethyl
dimethoxy
compound
Prior art date
Application number
HRP20160766TT
Other languages
English (en)
Inventor
Antonio Nardi
Bruno De Angelis
Paolangelo CEREA
Jane Llorenc Rafecas
Nicolas Tesson
Original Assignee
Laboratorio Chimico Internazionale S.P.A.
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 Laboratorio Chimico Internazionale S.P.A. filed Critical Laboratorio Chimico Internazionale S.P.A.
Publication of HRP20160766T1 publication Critical patent/HRP20160766T1/hr

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Classifications

    • 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
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/46—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of carboxylic acids or esters thereof in presence of ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/03—Monoamines
    • C07C211/04—Mono-, di- or tri-methylamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/50—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/132—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings
    • C07C53/134—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
    • 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
    • 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
    • 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
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Claims (7)

1. Postupak za pripremu (1S)-4,5-dimetoksi-1-(aminometil)-benzociklobutana formule (B): [image] naznačen time, da obuhvaća: (i) dovođenje u reakciju racemičnog 4,5-dimetoksi-1-(aminometil)-benzociklobutana s (S)-ibuprofenom u organskom otapalu; (ii) miješanje otopine pri sobnoj temperaturi dok se ne pojavi precipitat; (iii) obrada precipitata oblikovanog u stupnju (ii) s bazom da se oslobodi spoj (B) u svom (S) obliku; i; (iv) izoliranje spoja formule (B) u svom (S) obliku po izboru.
2. Postupak prema patentnom zahtjevu 1, naznačen time, da se (S)-ibuprofen koristi u najmanje dvostrukoj količini s obzirom na racemične polazne spojeve.
3. Postupak prema patentnom zahtjevu 2, naznačen time, da se (S)-ibuprofen koristi u najmanje trostrukoj količini s obzirom na racemične polazne spojeve.
4. Postupak prema bilo kojem od patentnih zahtjeva od 1 do 3, naznačen time, da se navedeno organsko otapalo odabire između acetonitrila i cikloheksana.
5. Postupak prema bilo kojem od patentnih zahtjeva od 1 do 4, naznačen time, da se precipitat oblikovan u stupnju (ii) obrađuje vodenom baznom otopinom i ekstrahira s organskim otapalom koje se ne može miješati s vodom.
6. (S)-ibuprofenat od (1S)-4,5-dimetoksi-1-(aminometil)-benzociklobutan•(S)-ibuprofena, naznačen time, da ima sljedeću formulu (C): [image]
7. Primjena spoja (C) prema patentnom zahtjevu 6, naznačena time, da jest za pripremanje spoja odabranog od (1S)-4,5-dimetoksi-1-(aminometil)-benzociklobutana i ivabradina.
HRP20160766TT 2011-08-01 2016-06-30 Postupak za proizvodnju ivabradina i intermedijera njegove sinteze HRP20160766T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT001467A ITMI20111467A1 (it) 2011-08-01 2011-08-01 Procedimento per la preparazione di ivabradina e di suoi intermedi di sintesi
EP12772396.3A EP2739610B1 (en) 2011-08-01 2012-07-31 Process for the manufacture of ivabradine and of intermediates of synthesis thereof
PCT/IB2012/001477 WO2013017937A1 (en) 2011-08-01 2012-07-31 Process for the manufacture of ivabradine and of intermediates of synthesis thereof

Publications (1)

Publication Number Publication Date
HRP20160766T1 true HRP20160766T1 (hr) 2016-08-12

Family

ID=44720966

Family Applications (1)

Application Number Title Priority Date Filing Date
HRP20160766TT HRP20160766T1 (hr) 2011-08-01 2016-06-30 Postupak za proizvodnju ivabradina i intermedijera njegove sinteze

Country Status (15)

Country Link
US (1) US9006424B2 (hr)
EP (1) EP2739610B1 (hr)
CN (1) CN103781767B (hr)
BR (1) BR112014002522A2 (hr)
CA (1) CA2843553A1 (hr)
CY (1) CY1118121T1 (hr)
EA (1) EA026170B1 (hr)
ES (1) ES2582673T3 (hr)
HR (1) HRP20160766T1 (hr)
HU (1) HUE029760T2 (hr)
IT (1) ITMI20111467A1 (hr)
PL (1) PL2739610T3 (hr)
PT (1) PT2739610T (hr)
SI (1) SI2739610T1 (hr)
WO (1) WO2013017937A1 (hr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3101010A1 (en) 2015-06-03 2016-12-07 Urquima S.A. New method for the preparation of highly pure ivabradine base and salts thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2681862B1 (fr) * 1991-09-27 1993-11-12 Adir Cie Nouvelles (benzocycloalkyl)alkylamines, leur procede de preparation, et les compositions pharmaceutiques qui les contiennent.
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
EP1935872A1 (en) * 2006-12-11 2008-06-25 Stirling Products Limited Process for obtaining the R-enantiomer of salbutamol
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
CN102264689B (zh) * 2008-12-22 2014-12-31 新梅斯托克尔卡公司 制备伊伐布雷定的方法

Also Published As

Publication number Publication date
WO2013017937A1 (en) 2013-02-07
SI2739610T1 (sl) 2016-08-31
EP2739610B1 (en) 2016-04-27
CY1118121T1 (el) 2017-06-28
BR112014002522A2 (pt) 2017-02-21
WO2013017937A8 (en) 2014-02-27
EA201400187A1 (ru) 2014-11-28
ITMI20111467A1 (it) 2013-02-02
CA2843553A1 (en) 2013-02-07
PT2739610T (pt) 2016-07-19
CN103781767A (zh) 2014-05-07
CN103781767B (zh) 2016-02-03
US9006424B2 (en) 2015-04-14
EA026170B1 (ru) 2017-03-31
HUE029760T2 (en) 2017-04-28
US20140357859A1 (en) 2014-12-04
PL2739610T3 (pl) 2016-11-30
ES2582673T3 (es) 2016-09-14
EP2739610A1 (en) 2014-06-11

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