Process for the preparation of a nitric oxide donating prostaglandin analogue
The present invention relates to a process for preparing hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I). In accordance with the present invention, the compound (I) can b...
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| creator | COUSIN, JONATHAN DIKER, KHALID ALMIRANTE, NICOLETTA RONSIN, GAEL GORINS, GILLES BRUNEAU, AUDREY |
| description | The present invention relates to a process for preparing hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I). In accordance with the present invention, the compound (I) can be efficiently prepared with high purity by coupling bimatoprost in a boronate protected form with 6-(nitrooxy)hexanoyl chloride and removing the boronate protecting group. The invention also relates to a process for the preparation of 6-(nitrooxy) hexanoic acid having a HPLC purity equal to or greater than 99% and containing an amount of 6-{[6-(nitrooxy)hexanoyl]oxy}hexanoic acid (compound(IXa)) equal to or lower than 0.2%. |
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In accordance with the present invention, the compound (I) can be efficiently prepared with high purity by coupling bimatoprost in a boronate protected form with 6-(nitrooxy)hexanoyl chloride and removing the boronate protecting group. The invention also relates to a process for the preparation of 6-(nitrooxy) hexanoic acid having a HPLC purity equal to or greater than 99% and containing an amount of 6-{[6-(nitrooxy)hexanoyl]oxy}hexanoic acid (compound(IXa)) equal to or lower than 0.2%.</description><language>chi ; eng</language><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS ; CHEMISTRY ; HUMAN NECESSITIES ; HYGIENE ; MEDICAL OR VETERINARY SCIENCE ; METALLURGY ; ORGANIC CHEMISTRY ; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES ; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</subject><creationdate>2022</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=20221101&DB=EPODOC&CC=TW&NR=202241390A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25542,76516</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20221101&DB=EPODOC&CC=TW&NR=202241390A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>COUSIN, JONATHAN</creatorcontrib><creatorcontrib>DIKER, KHALID</creatorcontrib><creatorcontrib>ALMIRANTE, NICOLETTA</creatorcontrib><creatorcontrib>RONSIN, GAEL</creatorcontrib><creatorcontrib>GORINS, GILLES</creatorcontrib><creatorcontrib>BRUNEAU, AUDREY</creatorcontrib><title>Process for the preparation of a nitric oxide donating prostaglandin analogue</title><description>The present invention relates to a process for preparing hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I). In accordance with the present invention, the compound (I) can be efficiently prepared with high purity by coupling bimatoprost in a boronate protected form with 6-(nitrooxy)hexanoyl chloride and removing the boronate protecting group. The invention also relates to a process for the preparation of 6-(nitrooxy) hexanoic acid having a HPLC purity equal to or greater than 99% and containing an amount of 6-{[6-(nitrooxy)hexanoyl]oxy}hexanoic acid (compound(IXa)) equal to or lower than 0.2%.</description><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS</subject><subject>CHEMISTRY</subject><subject>HUMAN NECESSITIES</subject><subject>HYGIENE</subject><subject>MEDICAL OR VETERINARY SCIENCE</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><subject>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</subject><subject>SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2022</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNqNyjEKAjEQQNE0FqLeYTyAsGZtLEV2sREsFiyXIZnEQJgJmQge3y08gNUv_lub-6OKI1UIUqG9CEqlghVbEgYJgMCp1eRAPskTeOFlcVyYaMOYkX1iQMYs8U1bswqYlXa_bsx-HKbr7UBFZtKCjpjaPD1tZ-3p2J-7S_-P-QLyGTaQ</recordid><startdate>20221101</startdate><enddate>20221101</enddate><creator>COUSIN, JONATHAN</creator><creator>DIKER, KHALID</creator><creator>ALMIRANTE, NICOLETTA</creator><creator>RONSIN, GAEL</creator><creator>GORINS, GILLES</creator><creator>BRUNEAU, AUDREY</creator><scope>EVB</scope></search><sort><creationdate>20221101</creationdate><title>Process for the preparation of a nitric oxide donating prostaglandin analogue</title><author>COUSIN, JONATHAN ; DIKER, KHALID ; ALMIRANTE, NICOLETTA ; RONSIN, GAEL ; GORINS, GILLES ; BRUNEAU, AUDREY</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_TW202241390A3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>chi ; eng</language><creationdate>2022</creationdate><topic>ACYCLIC OR CARBOCYCLIC COMPOUNDS</topic><topic>CHEMISTRY</topic><topic>HUMAN NECESSITIES</topic><topic>HYGIENE</topic><topic>MEDICAL OR VETERINARY SCIENCE</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><topic>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</topic><topic>SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</topic><toplevel>online_resources</toplevel><creatorcontrib>COUSIN, JONATHAN</creatorcontrib><creatorcontrib>DIKER, KHALID</creatorcontrib><creatorcontrib>ALMIRANTE, NICOLETTA</creatorcontrib><creatorcontrib>RONSIN, GAEL</creatorcontrib><creatorcontrib>GORINS, GILLES</creatorcontrib><creatorcontrib>BRUNEAU, AUDREY</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>COUSIN, JONATHAN</au><au>DIKER, KHALID</au><au>ALMIRANTE, NICOLETTA</au><au>RONSIN, GAEL</au><au>GORINS, GILLES</au><au>BRUNEAU, AUDREY</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Process for the preparation of a nitric oxide donating prostaglandin analogue</title><date>2022-11-01</date><risdate>2022</risdate><abstract>The present invention relates to a process for preparing hexanoic acid, 6-(nitrooxy)-, (1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl ester of formula (I). In accordance with the present invention, the compound (I) can be efficiently prepared with high purity by coupling bimatoprost in a boronate protected form with 6-(nitrooxy)hexanoyl chloride and removing the boronate protecting group. The invention also relates to a process for the preparation of 6-(nitrooxy) hexanoic acid having a HPLC purity equal to or greater than 99% and containing an amount of 6-{[6-(nitrooxy)hexanoyl]oxy}hexanoic acid (compound(IXa)) equal to or lower than 0.2%.</abstract><oa>free_for_read</oa></addata></record> |
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| subjects | ACYCLIC OR CARBOCYCLIC COMPOUNDS CHEMISTRY HUMAN NECESSITIES HYGIENE MEDICAL OR VETERINARY SCIENCE METALLURGY ORGANIC CHEMISTRY PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS |
| title | Process for the preparation of a nitric oxide donating prostaglandin analogue |
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