A PROCESS FOR THE PREPARATION OF EZETIMIBE VIA A NOVEL INTERMEDIATE
The present invention relates to a process for the preparation of Ezetimibe via a novel intermediate. Trans-3(R)-(3-[2-oxo-4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-azetidinyl]propanoic acid is converted to trans-N-methoxy-N-methyl-3(R)-3-[2-oxo-4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-azetidin...
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| creator | SHRIGADI, NILESH, BALKRISHNA PRABHAVALKAR, TIRTHA, SURESH THORAT, AMOL, NARAYAN RAMAKRISHNAN, ARUL |
| description | The present invention relates to a process for the preparation of Ezetimibe via a novel intermediate. Trans-3(R)-(3-[2-oxo-4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-azetidinyl]propanoic acid is converted to trans-N-methoxy-N-methyl-3(R)-3-[2-oxo-4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-azetidinyl]propanamide and the resultant intermediate is subjected to Grignard reaction to obtain trans-1-(4-fluorophenyl)-3(R)-[3-oxo-3-(4-fluorophenyl)propyl]-4(S)-(4-benzyloxyphenyl)-2-azetidinone. Reduction of trans-1-(4-JGiuorophenyl)-3(R)-[3-oxo-3-(4-fluorophenyl) propyl]-4(S)-(4-benzyloxyphenyl)-2-azetidinone, followed by debenzylation provides Ezetimibe. The invention also relates to the preparation of the intermediate occurring in the above process.
La présente invention concerne un procédé de préparation de l'ézétimibe via un nouvel intermédiaire. L'acide trans-3(R)-(3-[2-oxo-4(S)-(4-benzyloxyphényl)-1-(4-fluorophényl)-azétidinyl]propanoïque est converti en trans-N-méthoxy-N-méthyl-3(R)-3-[2-oxo-4(S)-(4-benzyloxyphényl)-1-(4-fluorophényl)-azétidinyl]propanamide et l'intermédiaire résultant est soumis à une réaction de Grignard de façon à obtenir la trans-1-(4-fluorophényl)-3(R)-[3-oxo-3-(4-fluorophényl)propyl]-4(S)-(4-benzyloxyphényl)-2-azétidinone. La réduction de la trans-1-(4-fluorophényl)-3(R)-[3-oxo-3-(4-fluorophényl)propyl]-4(S)-(4-benzyloxyphényl)-2-azétidinone, suivie de la débenzylation donne l'ézétimibe. L'invention concerne également la préparation de l'intermédiaire rencontré dans le procédé susmentionné. |
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La présente invention concerne un procédé de préparation de l'ézétimibe via un nouvel intermédiaire. L'acide trans-3(R)-(3-[2-oxo-4(S)-(4-benzyloxyphényl)-1-(4-fluorophényl)-azétidinyl]propanoïque est converti en trans-N-méthoxy-N-méthyl-3(R)-3-[2-oxo-4(S)-(4-benzyloxyphényl)-1-(4-fluorophényl)-azétidinyl]propanamide et l'intermédiaire résultant est soumis à une réaction de Grignard de façon à obtenir la trans-1-(4-fluorophényl)-3(R)-[3-oxo-3-(4-fluorophényl)propyl]-4(S)-(4-benzyloxyphényl)-2-azétidinone. La réduction de la trans-1-(4-fluorophényl)-3(R)-[3-oxo-3-(4-fluorophényl)propyl]-4(S)-(4-benzyloxyphényl)-2-azétidinone, suivie de la débenzylation donne l'ézétimibe. L'invention concerne également la préparation de l'intermédiaire rencontré dans le procédé susmentionné.</description><language>eng ; fre</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>2007</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&date=20070927&DB=EPODOC&CC=WO&NR=2007108007A1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25542,76290</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20070927&DB=EPODOC&CC=WO&NR=2007108007A1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>SHRIGADI, NILESH, BALKRISHNA</creatorcontrib><creatorcontrib>PRABHAVALKAR, TIRTHA, SURESH</creatorcontrib><creatorcontrib>THORAT, AMOL, NARAYAN</creatorcontrib><creatorcontrib>RAMAKRISHNAN, ARUL</creatorcontrib><title>A PROCESS FOR THE PREPARATION OF EZETIMIBE VIA A NOVEL INTERMEDIATE</title><description>The present invention relates to a process for the preparation of Ezetimibe via a novel intermediate. Trans-3(R)-(3-[2-oxo-4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-azetidinyl]propanoic acid is converted to trans-N-methoxy-N-methyl-3(R)-3-[2-oxo-4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-azetidinyl]propanamide and the resultant intermediate is subjected to Grignard reaction to obtain trans-1-(4-fluorophenyl)-3(R)-[3-oxo-3-(4-fluorophenyl)propyl]-4(S)-(4-benzyloxyphenyl)-2-azetidinone. Reduction of trans-1-(4-JGiuorophenyl)-3(R)-[3-oxo-3-(4-fluorophenyl) propyl]-4(S)-(4-benzyloxyphenyl)-2-azetidinone, followed by debenzylation provides Ezetimibe. The invention also relates to the preparation of the intermediate occurring in the above process.
La présente invention concerne un procédé de préparation de l'ézétimibe via un nouvel intermédiaire. L'acide trans-3(R)-(3-[2-oxo-4(S)-(4-benzyloxyphényl)-1-(4-fluorophényl)-azétidinyl]propanoïque est converti en trans-N-méthoxy-N-méthyl-3(R)-3-[2-oxo-4(S)-(4-benzyloxyphényl)-1-(4-fluorophényl)-azétidinyl]propanamide et l'intermédiaire résultant est soumis à une réaction de Grignard de façon à obtenir la trans-1-(4-fluorophényl)-3(R)-[3-oxo-3-(4-fluorophényl)propyl]-4(S)-(4-benzyloxyphényl)-2-azétidinone. La réduction de la trans-1-(4-fluorophényl)-3(R)-[3-oxo-3-(4-fluorophényl)propyl]-4(S)-(4-benzyloxyphényl)-2-azétidinone, suivie de la débenzylation donne l'ézétimibe. L'invention concerne également la préparation de l'intermédiaire rencontré dans le procédé susmentionné.</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2007</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZHB2VAgI8nd2DQ5WcPMPUgjxcAXyXQMcgxxDPP39FPzdFFyjXEM8fT2dXBXCPB0VHBX8_MNcfRQ8_UJcg3xdXTwdQ1x5GFjTEnOKU3mhNDeDsptriLOHbmpBfnxqcUFicmpeakl8uL-RgYG5oYEFkHQ0NCZOFQCvSSwM</recordid><startdate>20070927</startdate><enddate>20070927</enddate><creator>SHRIGADI, NILESH, BALKRISHNA</creator><creator>PRABHAVALKAR, TIRTHA, SURESH</creator><creator>THORAT, AMOL, NARAYAN</creator><creator>RAMAKRISHNAN, ARUL</creator><scope>EVB</scope></search><sort><creationdate>20070927</creationdate><title>A PROCESS FOR THE PREPARATION OF EZETIMIBE VIA A NOVEL INTERMEDIATE</title><author>SHRIGADI, NILESH, BALKRISHNA ; PRABHAVALKAR, TIRTHA, SURESH ; THORAT, AMOL, NARAYAN ; RAMAKRISHNAN, ARUL</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_WO2007108007A13</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng ; fre</language><creationdate>2007</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>SHRIGADI, NILESH, BALKRISHNA</creatorcontrib><creatorcontrib>PRABHAVALKAR, TIRTHA, SURESH</creatorcontrib><creatorcontrib>THORAT, AMOL, NARAYAN</creatorcontrib><creatorcontrib>RAMAKRISHNAN, ARUL</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>SHRIGADI, NILESH, BALKRISHNA</au><au>PRABHAVALKAR, TIRTHA, SURESH</au><au>THORAT, AMOL, NARAYAN</au><au>RAMAKRISHNAN, ARUL</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>A PROCESS FOR THE PREPARATION OF EZETIMIBE VIA A NOVEL INTERMEDIATE</title><date>2007-09-27</date><risdate>2007</risdate><abstract>The present invention relates to a process for the preparation of Ezetimibe via a novel intermediate. Trans-3(R)-(3-[2-oxo-4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-azetidinyl]propanoic acid is converted to trans-N-methoxy-N-methyl-3(R)-3-[2-oxo-4(S)-(4-benzyloxyphenyl)-1-(4-fluorophenyl)-azetidinyl]propanamide and the resultant intermediate is subjected to Grignard reaction to obtain trans-1-(4-fluorophenyl)-3(R)-[3-oxo-3-(4-fluorophenyl)propyl]-4(S)-(4-benzyloxyphenyl)-2-azetidinone. Reduction of trans-1-(4-JGiuorophenyl)-3(R)-[3-oxo-3-(4-fluorophenyl) propyl]-4(S)-(4-benzyloxyphenyl)-2-azetidinone, followed by debenzylation provides Ezetimibe. The invention also relates to the preparation of the intermediate occurring in the above process.
La présente invention concerne un procédé de préparation de l'ézétimibe via un nouvel intermédiaire. L'acide trans-3(R)-(3-[2-oxo-4(S)-(4-benzyloxyphényl)-1-(4-fluorophényl)-azétidinyl]propanoïque est converti en trans-N-méthoxy-N-méthyl-3(R)-3-[2-oxo-4(S)-(4-benzyloxyphényl)-1-(4-fluorophényl)-azétidinyl]propanamide et l'intermédiaire résultant est soumis à une réaction de Grignard de façon à obtenir la trans-1-(4-fluorophényl)-3(R)-[3-oxo-3-(4-fluorophényl)propyl]-4(S)-(4-benzyloxyphényl)-2-azétidinone. La réduction de la trans-1-(4-fluorophényl)-3(R)-[3-oxo-3-(4-fluorophényl)propyl]-4(S)-(4-benzyloxyphényl)-2-azétidinone, suivie de la débenzylation donne l'ézétimibe. L'invention concerne également la préparation de l'intermédiaire rencontré dans le procédé susmentionné.</abstract><oa>free_for_read</oa></addata></record> |
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| title | A PROCESS FOR THE PREPARATION OF EZETIMIBE VIA A NOVEL INTERMEDIATE |
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