The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan
The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole imidazole interaction was confirmed by s...
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| Veröffentlicht in: | RSC advances 2019-02, Vol.9 (9), p.5244-525 |
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| creator | Araya-Sibaja, Andrea M Urgellés, Mariola Vásquez-Castro, Felipe Vargas-Huertas, Felipe Vega-Baudrit, José Roberto Guillén-Girón, Teodolito Navarro-Hoyos, Mirtha Cuffini, Silvia L |
| description | The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole imidazole interaction was confirmed by solution-state NMR. The results showed that highly polar and polarisable solvents (higher values of the electrostatic factor (EF)) lead to the crystallisation of IBS form B. Furthermore, the variations of pH in methanol, in turn, determined the crystallisation of desmotropes A and/or B.
The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. |
| doi_str_mv | 10.1039/c8ra10146a |
| format | Article |
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The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c8ra10146a</identifier><identifier>PMID: 35514656</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Chemistry ; Crystallization ; Imidazole ; NMR ; Nuclear magnetic resonance ; Tautomers ; Tetrazoles</subject><ispartof>RSC advances, 2019-02, Vol.9 (9), p.5244-525</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2019</rights><rights>This journal is © The Royal Society of Chemistry 2019 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c428t-239bb8a8406ab0e40c7f9706ba361d92b9f1d97640338e38d9935f4ade8dc0433</citedby><cites>FETCH-LOGICAL-c428t-239bb8a8406ab0e40c7f9706ba361d92b9f1d97640338e38d9935f4ade8dc0433</cites><orcidid>0000-0003-2115-4677 ; 0000-0003-1823-3403 ; 0000-0003-2591-7117 ; 0000-0001-9809-6079</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9060688/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC9060688/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35514656$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Araya-Sibaja, Andrea M</creatorcontrib><creatorcontrib>Urgellés, Mariola</creatorcontrib><creatorcontrib>Vásquez-Castro, Felipe</creatorcontrib><creatorcontrib>Vargas-Huertas, Felipe</creatorcontrib><creatorcontrib>Vega-Baudrit, José Roberto</creatorcontrib><creatorcontrib>Guillén-Girón, Teodolito</creatorcontrib><creatorcontrib>Navarro-Hoyos, Mirtha</creatorcontrib><creatorcontrib>Cuffini, Silvia L</creatorcontrib><title>The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole imidazole interaction was confirmed by solution-state NMR. The results showed that highly polar and polarisable solvents (higher values of the electrostatic factor (EF)) lead to the crystallisation of IBS form B. Furthermore, the variations of pH in methanol, in turn, determined the crystallisation of desmotropes A and/or B.
The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein.</description><subject>Chemistry</subject><subject>Crystallization</subject><subject>Imidazole</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Tautomers</subject><subject>Tetrazoles</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpdkt9LHDEQx0NpqWJ96btloS9SOJ1sdnPJi3Ac9gcIguhzmM0mGtlNrklW8L8369mrmpdJ8v3Ml5lMCPlK4YQCk6daRKRAG44fyH4NDV_UwOXHV_s9cpjSPZTFW1pz-pnssbYtGS3fJ-n6zlTGWqNzFWyVwjBlF3xl_IOLwY_G5wp9X-UZGwoVQ8qYna4s6hxiVdhZ0_Gx3A-DS_icX7x6k8ZQ-I1J89HFziSMGf0X8snikMzhSzwgNz_Pr9e_FxeXv_6sVxcL3dQiL2omu06gaIBjB6YBvbRyCbxDxmkv607aEpa8AcaEYaKXkrW2wd6IXkPD2AE52_pupm40vS69RBzUJroR46MK6NRbxbs7dRselAQOXIhicPxiEMPfyaSsRpe0GQb0JkxJ1ZxTEEyALOj3d-h9mKIv7amaCka5WMJc0Y8tpcszpmjsrhgKah6nWour1fM4VwX-9rr8HfpveAU42gIx6Z36_z-wJ2JLpqI</recordid><startdate>20190211</startdate><enddate>20190211</enddate><creator>Araya-Sibaja, Andrea M</creator><creator>Urgellés, Mariola</creator><creator>Vásquez-Castro, Felipe</creator><creator>Vargas-Huertas, Felipe</creator><creator>Vega-Baudrit, José Roberto</creator><creator>Guillén-Girón, Teodolito</creator><creator>Navarro-Hoyos, Mirtha</creator><creator>Cuffini, Silvia L</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0003-2115-4677</orcidid><orcidid>https://orcid.org/0000-0003-1823-3403</orcidid><orcidid>https://orcid.org/0000-0003-2591-7117</orcidid><orcidid>https://orcid.org/0000-0001-9809-6079</orcidid></search><sort><creationdate>20190211</creationdate><title>The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan</title><author>Araya-Sibaja, Andrea M ; Urgellés, Mariola ; Vásquez-Castro, Felipe ; Vargas-Huertas, Felipe ; Vega-Baudrit, José Roberto ; Guillén-Girón, Teodolito ; Navarro-Hoyos, Mirtha ; Cuffini, Silvia L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-239bb8a8406ab0e40c7f9706ba361d92b9f1d97640338e38d9935f4ade8dc0433</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Chemistry</topic><topic>Crystallization</topic><topic>Imidazole</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Tautomers</topic><topic>Tetrazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Araya-Sibaja, Andrea M</creatorcontrib><creatorcontrib>Urgellés, Mariola</creatorcontrib><creatorcontrib>Vásquez-Castro, Felipe</creatorcontrib><creatorcontrib>Vargas-Huertas, Felipe</creatorcontrib><creatorcontrib>Vega-Baudrit, José Roberto</creatorcontrib><creatorcontrib>Guillén-Girón, Teodolito</creatorcontrib><creatorcontrib>Navarro-Hoyos, Mirtha</creatorcontrib><creatorcontrib>Cuffini, Silvia L</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Araya-Sibaja, Andrea M</au><au>Urgellés, Mariola</au><au>Vásquez-Castro, Felipe</au><au>Vargas-Huertas, Felipe</au><au>Vega-Baudrit, José Roberto</au><au>Guillén-Girón, Teodolito</au><au>Navarro-Hoyos, Mirtha</au><au>Cuffini, Silvia L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2019-02-11</date><risdate>2019</risdate><volume>9</volume><issue>9</issue><spage>5244</spage><epage>525</epage><pages>5244-525</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>The experimental conditions necessary for stabilising irbesartan (IBS) tautomers in solution and selectively obtaining the desmotropic crystal forms are presented herein. 1H and 2H tautomers were stabilized in specific solution conditions and the 2H-tetrazole imidazole interaction was confirmed by solution-state NMR. The results showed that highly polar and polarisable solvents (higher values of the electrostatic factor (EF)) lead to the crystallisation of IBS form B. Furthermore, the variations of pH in methanol, in turn, determined the crystallisation of desmotropes A and/or B.
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| subjects | Chemistry Crystallization Imidazole NMR Nuclear magnetic resonance Tautomers Tetrazoles |
| title | The effect of solution environment and the electrostatic factor on the crystallisation of desmotropes of irbesartan |
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