NOVEL METHOD FOR SYNTHESISING IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS

NOVEL METHOD FOR SYNTHESISING IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS

Preparing 2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propyl]-6,7-dimethoxy-1,4-dihydroisoquinolin-3-one (I) comprises subjecting 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic aci...

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Hauptverfasser: Grandjean, Mathieu, Le Flohic, Alexandre
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ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Le Flohic, Alexandre
description Preparing 2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propyl]-6,7-dimethoxy-1,4-dihydroisoquinolin-3-one (I) comprises subjecting 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II) to a lactamization reaction, in the presence of a coupling agent and a base, in an organic solvent, to yield (I), which is converted into an addition salt with an acid consisting of e.g. hydrochloric acid, hydrobromic acid, sulfuric acid and phosphoric acid and into hydrates of salt. Preparing 2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propyl]-6,7-dimethoxy-1,4-dihydroisoquinolin-3-one (I) comprises subjecting 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II) to a lactamization reaction, in the presence of a coupling agent and a base, in an organic solvent, to yield (I), which is converted into an addition salt with an acid consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, lactic acid, pyruvic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, tartaric acid, maleic acid, citric acid, ascorbic acid, oxalic acid, methanesulfonic acid, benzenesulfonic acid and camphoric acid and into hydrates of salt. Independent claims are included for: (1) the 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II); (2) 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetonitrile (V); (3) 2-[2-[2-(3-chloropropylamino)ethyl]-4,5-dimethoxy-phenyl]acetonitrile (VI); (4) 3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]-1-propanol; (5) N-{2-[2-(cyanomethyl)-4,5-dimethoxyphenyl]ethyl}-beta -alaninate ethyl oxalate; and (6) (2-{2-[(3-hydroxypropyl)amino]ethyl}-4,5-dimethoxyphenyl)acetonitrile. ACTIVITY : Cardiant; Vasotropic; Antianginal. MECHANISM OF ACTION : None given.
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Preparing 2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propyl]-6,7-dimethoxy-1,4-dihydroisoquinolin-3-one (I) comprises subjecting 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II) to a lactamization reaction, in the presence of a coupling agent and a base, in an organic solvent, to yield (I), which is converted into an addition salt with an acid consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, lactic acid, pyruvic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, tartaric acid, maleic acid, citric acid, ascorbic acid, oxalic acid, methanesulfonic acid, benzenesulfonic acid and camphoric acid and into hydrates of salt. Independent claims are included for: (1) the 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II); (2) 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetonitrile (V); (3) 2-[2-[2-(3-chloropropylamino)ethyl]-4,5-dimethoxy-phenyl]acetonitrile (VI); (4) 3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]-1-propanol; (5) N-{2-[2-(cyanomethyl)-4,5-dimethoxyphenyl]ethyl}-beta -alaninate ethyl oxalate; and (6) (2-{2-[(3-hydroxypropyl)amino]ethyl}-4,5-dimethoxyphenyl)acetonitrile. ACTIVITY : Cardiant; Vasotropic; Antianginal. MECHANISM OF ACTION : None given.</description><language>hrv ; eng</language><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS ; CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>2016</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=20160408&amp;DB=EPODOC&amp;CC=HR&amp;NR=P20160262T1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25564,76547</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=20160408&amp;DB=EPODOC&amp;CC=HR&amp;NR=P20160262T1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>Grandjean, Mathieu</creatorcontrib><creatorcontrib>Le Flohic, Alexandre</creatorcontrib><title>NOVEL METHOD FOR SYNTHESISING IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS</title><description>Preparing 2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propyl]-6,7-dimethoxy-1,4-dihydroisoquinolin-3-one (I) comprises subjecting 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II) to a lactamization reaction, in the presence of a coupling agent and a base, in an organic solvent, to yield (I), which is converted into an addition salt with an acid consisting of e.g. hydrochloric acid, hydrobromic acid, sulfuric acid and phosphoric acid and into hydrates of salt. Preparing 2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propyl]-6,7-dimethoxy-1,4-dihydroisoquinolin-3-one (I) comprises subjecting 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II) to a lactamization reaction, in the presence of a coupling agent and a base, in an organic solvent, to yield (I), which is converted into an addition salt with an acid consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, lactic acid, pyruvic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, tartaric acid, maleic acid, citric acid, ascorbic acid, oxalic acid, methanesulfonic acid, benzenesulfonic acid and camphoric acid and into hydrates of salt. Independent claims are included for: (1) the 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II); (2) 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetonitrile (V); (3) 2-[2-[2-(3-chloropropylamino)ethyl]-4,5-dimethoxy-phenyl]acetonitrile (VI); (4) 3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]-1-propanol; (5) N-{2-[2-(cyanomethyl)-4,5-dimethoxyphenyl]ethyl}-beta -alaninate ethyl oxalate; and (6) (2-{2-[(3-hydroxypropyl)amino]ethyl}-4,5-dimethoxyphenyl)acetonitrile. ACTIVITY : Cardiant; Vasotropic; Antianginal. MECHANISM OF ACTION : None given.</description><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS</subject><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2016</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNqNyrEKwjAQANAuDqL-w4Gz0Fbofk2u5iBNSnItdKpF4iRaqP-PDn6A01veNrs6P5CFlsR4DY0PEEcnhiJHdhfgAeuAmh0BOg0sETqDoUVFvbBCa0dApagTrO33KNaAWrOwdxDRStxnm_v8WNPh5y47NiTKnNLymtK6zLf0TO_JhK7Miyovq1KkOP-3Pl7-NM8</recordid><startdate>20160408</startdate><enddate>20160408</enddate><creator>Grandjean, Mathieu</creator><creator>Le Flohic, Alexandre</creator><scope>EVB</scope></search><sort><creationdate>20160408</creationdate><title>NOVEL METHOD FOR SYNTHESISING IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS</title><author>Grandjean, Mathieu ; Le Flohic, Alexandre</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_HRP20160262TT13</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>hrv ; eng</language><creationdate>2016</creationdate><topic>ACYCLIC OR CARBOCYCLIC COMPOUNDS</topic><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>Grandjean, Mathieu</creatorcontrib><creatorcontrib>Le Flohic, Alexandre</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Grandjean, Mathieu</au><au>Le Flohic, Alexandre</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>NOVEL METHOD FOR SYNTHESISING IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS</title><date>2016-04-08</date><risdate>2016</risdate><abstract>Preparing 2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propyl]-6,7-dimethoxy-1,4-dihydroisoquinolin-3-one (I) comprises subjecting 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II) to a lactamization reaction, in the presence of a coupling agent and a base, in an organic solvent, to yield (I), which is converted into an addition salt with an acid consisting of e.g. hydrochloric acid, hydrobromic acid, sulfuric acid and phosphoric acid and into hydrates of salt. Preparing 2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propyl]-6,7-dimethoxy-1,4-dihydroisoquinolin-3-one (I) comprises subjecting 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II) to a lactamization reaction, in the presence of a coupling agent and a base, in an organic solvent, to yield (I), which is converted into an addition salt with an acid consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, lactic acid, pyruvic acid, malonic acid, succinic acid, glutaric acid, fumaric acid, tartaric acid, maleic acid, citric acid, ascorbic acid, oxalic acid, methanesulfonic acid, benzenesulfonic acid and camphoric acid and into hydrates of salt. Independent claims are included for: (1) the 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetic acid (II); (2) 2-[2-[2-[3-[(3,4-dimethoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl-methyl-amino]propylamino]ethyl]-4,5-dimethoxy-phenyl]acetonitrile (V); (3) 2-[2-[2-(3-chloropropylamino)ethyl]-4,5-dimethoxy-phenyl]acetonitrile (VI); (4) 3-[{[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino]-1-propanol; (5) N-{2-[2-(cyanomethyl)-4,5-dimethoxyphenyl]ethyl}-beta -alaninate ethyl oxalate; and (6) (2-{2-[(3-hydroxypropyl)amino]ethyl}-4,5-dimethoxyphenyl)acetonitrile. ACTIVITY : Cardiant; Vasotropic; Antianginal. MECHANISM OF ACTION : None given.</abstract><oa>free_for_read</oa></addata></record>
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subjects ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
title NOVEL METHOD FOR SYNTHESISING IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE ACID ADDITION SALTS
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