Synthesis intermediates useful for preparing zolmitriptan
In particular, this invention relates to the synthesis intermediates (IV), (V), (VI) and (VIII) useful for preparing zolmitriptanzohnitriptan or a pharmaceutically acceptable salt thereof, which includes a) Ppreparation of the diazonium salt of the aniline hydrochloride (II); followed by reduction a...
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creator | Dalmases Barjoan, Pere Armengol Asparo, Montserrat |
description | In particular, this invention relates to the synthesis intermediates (IV), (V), (VI) and (VIII) useful for preparing zolmitriptanzohnitriptan or a pharmaceutically acceptable salt thereof, which includes a) Ppreparation of the diazonium salt of the aniline hydrochloride (II); followed by reduction and acidification to give hydrazine (III); b) In situ Reaction of the hydrazine hydrochloride (III) with α-keto-δ-valerolactone, to give the hydrazone (IV); c) Fischer indole synthesis of the hydrazone (IV), to give the pyranoindolone of formula (V); d) Ttransesterification of the pyranoindolone (V) to provide the compound (VI), in which R means a straight or branched C1-C4 alkyl; e) Conversion of the hydroxyl group of the compound (VI) into dimethylamino to give the indolecarboxylate (VII), in which R means a straight or branched C1-C4 alkyl; f) Ssaponification of the 2-carboalkoxy group of the compound (VII), to provide indolecarboxylic acid (VIII); g) Ddecarboxylation of the indolecarboxylic acid (VIII), to provide zolmitriptan and, eventually, to provide a pharmaceutically acceptable salt thereof. |
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followed by reduction and acidification to give hydrazine (III); b) In situ Reaction of the hydrazine hydrochloride (III) with α-keto-δ-valerolactone, to give the hydrazone (IV); c) Fischer indole synthesis of the hydrazone (IV), to give the pyranoindolone of formula (V); d) Ttransesterification of the pyranoindolone (V) to provide the compound (VI), in which R means a straight or branched C1-C4 alkyl; e) Conversion of the hydroxyl group of the compound (VI) into dimethylamino to give the indolecarboxylate (VII), in which R means a straight or branched C1-C4 alkyl; f) Ssaponification of the 2-carboalkoxy group of the compound (VII), to provide indolecarboxylic acid (VIII); g) Ddecarboxylation of the indolecarboxylic acid (VIII), to provide zolmitriptan and, eventually, to provide a pharmaceutically acceptable salt thereof.</description><language>eng</language><creationdate>2009</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7563904$$EPDF$$P50$$Guspatents$$Hfree_for_read</linktopdf><link.rule.ids>230,309,781,803,886,64041</link.rule.ids><linktorsrc>$$Uhttps://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7563904$$EView_record_in_USPTO$$FView_record_in_$$GUSPTO$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>Dalmases Barjoan, Pere</creatorcontrib><creatorcontrib>Armengol Asparo, Montserrat</creatorcontrib><creatorcontrib>Inke, S.A</creatorcontrib><title>Synthesis intermediates useful for preparing zolmitriptan</title><description>In particular, this invention relates to the synthesis intermediates (IV), (V), (VI) and (VIII) useful for preparing zolmitriptanzohnitriptan or a pharmaceutically acceptable salt thereof, which includes a) Ppreparation of the diazonium salt of the aniline hydrochloride (II); followed by reduction and acidification to give hydrazine (III); b) In situ Reaction of the hydrazine hydrochloride (III) with α-keto-δ-valerolactone, to give the hydrazone (IV); c) Fischer indole synthesis of the hydrazone (IV), to give the pyranoindolone of formula (V); d) Ttransesterification of the pyranoindolone (V) to provide the compound (VI), in which R means a straight or branched C1-C4 alkyl; e) Conversion of the hydroxyl group of the compound (VI) into dimethylamino to give the indolecarboxylate (VII), in which R means a straight or branched C1-C4 alkyl; f) Ssaponification of the 2-carboalkoxy group of the compound (VII), to provide indolecarboxylic acid (VIII); g) Ddecarboxylation of the indolecarboxylic acid (VIII), to provide zolmitriptan and, eventually, to provide a pharmaceutically acceptable salt thereof.</description><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2009</creationdate><recordtype>patent</recordtype><sourceid>EFH</sourceid><recordid>eNrjZLAMrswryUgtzixWyMwrSS3KTU3JTCxJLVYoLU5NK81RSMsvUigoSi1ILMrMS1eoys_JzSwpyiwoSczjYWBNS8wpTuWF0twMCm6uIc4euqXFBUAT8kqK49OLEkGUgbmpmbGlgYkxEUoAkQ0wug</recordid><startdate>20090721</startdate><enddate>20090721</enddate><creator>Dalmases Barjoan, Pere</creator><creator>Armengol Asparo, Montserrat</creator><scope>EFH</scope></search><sort><creationdate>20090721</creationdate><title>Synthesis intermediates useful for preparing zolmitriptan</title><author>Dalmases Barjoan, Pere ; Armengol Asparo, Montserrat</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-uspatents_grants_075639043</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>2009</creationdate><toplevel>online_resources</toplevel><creatorcontrib>Dalmases Barjoan, Pere</creatorcontrib><creatorcontrib>Armengol Asparo, Montserrat</creatorcontrib><creatorcontrib>Inke, S.A</creatorcontrib><collection>USPTO Issued Patents</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Dalmases Barjoan, Pere</au><au>Armengol Asparo, Montserrat</au><aucorp>Inke, S.A</aucorp><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Synthesis intermediates useful for preparing zolmitriptan</title><date>2009-07-21</date><risdate>2009</risdate><abstract>In particular, this invention relates to the synthesis intermediates (IV), (V), (VI) and (VIII) useful for preparing zolmitriptanzohnitriptan or a pharmaceutically acceptable salt thereof, which includes a) Ppreparation of the diazonium salt of the aniline hydrochloride (II); followed by reduction and acidification to give hydrazine (III); b) In situ Reaction of the hydrazine hydrochloride (III) with α-keto-δ-valerolactone, to give the hydrazone (IV); c) Fischer indole synthesis of the hydrazone (IV), to give the pyranoindolone of formula (V); d) Ttransesterification of the pyranoindolone (V) to provide the compound (VI), in which R means a straight or branched C1-C4 alkyl; e) Conversion of the hydroxyl group of the compound (VI) into dimethylamino to give the indolecarboxylate (VII), in which R means a straight or branched C1-C4 alkyl; f) Ssaponification of the 2-carboalkoxy group of the compound (VII), to provide indolecarboxylic acid (VIII); g) Ddecarboxylation of the indolecarboxylic acid (VIII), to provide zolmitriptan and, eventually, to provide a pharmaceutically acceptable salt thereof.</abstract><oa>free_for_read</oa></addata></record> |
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title | Synthesis intermediates useful for preparing zolmitriptan |
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