Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate

The synthesis, stereostructure, and enantiomeric separation by chromatography of a new, chiral anxiolytic agent, deramciclane fumarate (2, (−)‐[1R,2S,4R]‐2‐(2‐dimethylaminoethoxy)‐2‐phenyl‐1,7,7‐trimethylbicyclo[2.2.1]heptane fumarate, EGIS‐3886), is described. The optical antipode and the racemate...

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Veröffentlicht in:	Chirality (New York, N.Y.) N.Y.), 1999, Vol.11 (9), p.689-693
Hauptverfasser:	Ladányi, László, Sztruhár, Ilona, Budai, Zoltán, Lukács, Gyula, Mezei, Tibor, Argay, Gyula, Kálmán, Alajos, Simig, Gyula
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Sprache:	eng
Schlagworte:	Anti-Anxiety Agents - chemistry Anti-Anxiety Agents - isolation & purification anxiolytic agent Bornanes - chemistry Bornanes - isolation & purification chiral HPLC Chromatography, High Pressure Liquid deramciclane fumarate enantiomeric purity stereochemistry Stereoisomerism X-ray analysis X-Ray Diffraction
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container_title	Chirality (New York, N.Y.)
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creator	Ladányi, László Sztruhár, Ilona Budai, Zoltán Lukács, Gyula Mezei, Tibor Argay, Gyula Kálmán, Alajos Simig, Gyula
description	The synthesis, stereostructure, and enantiomeric separation by chromatography of a new, chiral anxiolytic agent, deramciclane fumarate (2, (−)‐[1R,2S,4R]‐2‐(2‐dimethylaminoethoxy)‐2‐phenyl‐1,7,7‐trimethylbicyclo[2.2.1]heptane fumarate, EGIS‐3886), is described. The optical antipode and the racemate of compound 2 were also prepared. The structure was determined by single crystal X‐ray diffraction analysis. The enantiomeric separation was accomplished by HPLC on Chiralcel OD (250 × 4.6 mm; 10 μm) and hexane‐ethanol (99.5:0.5) as mobile phase at room temperature. The enantiomeric purity of the synthesized drug substance proved to be very high (>99.9%). Some statements published earlier on the stereostructure of deramciclane fumarate are critically discussed. Chirality 11:689–693, 1999. © 1999 Wiley‐Liss, Inc.
doi_str_mv	10.1002/(SICI)1520-636X(1999)11:9<689::AID-CHIR4>3.0.CO;2-X
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The optical antipode and the racemate of compound 2 were also prepared. The structure was determined by single crystal X‐ray diffraction analysis. The enantiomeric separation was accomplished by HPLC on Chiralcel OD (250 × 4.6 mm; 10 μm) and hexane‐ethanol (99.5:0.5) as mobile phase at room temperature. The enantiomeric purity of the synthesized drug substance proved to be very high (>99.9%). Some statements published earlier on the stereostructure of deramciclane fumarate are critically discussed. 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The optical antipode and the racemate of compound 2 were also prepared. The structure was determined by single crystal X‐ray diffraction analysis. The enantiomeric separation was accomplished by HPLC on Chiralcel OD (250 × 4.6 mm; 10 μm) and hexane‐ethanol (99.5:0.5) as mobile phase at room temperature. The enantiomeric purity of the synthesized drug substance proved to be very high (>99.9%). Some statements published earlier on the stereostructure of deramciclane fumarate are critically discussed. Chirality 11:689–693, 1999. © 1999 Wiley‐Liss, Inc.</description><subject>Anti-Anxiety Agents - chemistry</subject><subject>Anti-Anxiety Agents - isolation & purification</subject><subject>anxiolytic agent</subject><subject>Bornanes - chemistry</subject><subject>Bornanes - isolation & purification</subject><subject>chiral HPLC</subject><subject>Chromatography, High Pressure Liquid</subject><subject>deramciclane fumarate</subject><subject>enantiomeric purity</subject><subject>stereochemistry</subject><subject>Stereoisomerism</subject><subject>X-ray analysis</subject><subject>X-Ray Diffraction</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kW9r1TAUh4Mo7jr9CtJXsoG9Jk2TJncijKpbYeyKd7KLbw5peq529s81bXX99qZ2DEHxVSB5-P3OeULICaNLRmn06miTpdkxExENJZfbI6a1PmZspV9LpVer0-xtmJ5nH-M3fEmX6fokCrcPyOKef0gWVGkdUhpHB-RJ191QSrXk8WNywKigMo70gnze9OiwtV-xLrvejYFpigAb0_RlW6MrbbAfXNmPQbsLTNC0P7DyyG3ZVmPvH80XbPqXQYHO1La0lWkw2A21cabHp-TRzlQdPrs7D8mn9--u0vPwYn2WpacXoeVaxSEywwvFC0u5zAtrtVUqpjzBnRBGKZFHXLBIGqFkIeKCChsVDBOjeZ6oPGb8kLyYc_eu_T5g14NfxWI1DdMOHSQ0SRLGJ3Azg9a1XedwB3tX-llHYBQm5QCTcpgUwqQQJuXAGGjwygG8cvitHDhQSNcQwdanPr-rH_Iaiz8yZ8ceuJqBn2WF41-d_638V-N84WPDOdb_G97exxr3DWTCEwHXl2eQyg_JtbyUwPgvpMesTg</recordid><startdate>1999</startdate><enddate>1999</enddate><creator>Ladányi, László</creator><creator>Sztruhár, Ilona</creator><creator>Budai, Zoltán</creator><creator>Lukács, Gyula</creator><creator>Mezei, Tibor</creator><creator>Argay, Gyula</creator><creator>Kálmán, Alajos</creator><creator>Simig, Gyula</creator><general>John Wiley & Sons, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>1999</creationdate><title>Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate</title><author>Ladányi, László ; Sztruhár, Ilona ; Budai, Zoltán ; Lukács, Gyula ; Mezei, Tibor ; Argay, Gyula ; Kálmán, Alajos ; Simig, Gyula</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3984-e1a3d83dc036bdcc9c884037ef55a885b235126a586d54d05c2d1e7a93b78b413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Anti-Anxiety Agents - chemistry</topic><topic>Anti-Anxiety Agents - isolation & purification</topic><topic>anxiolytic agent</topic><topic>Bornanes - chemistry</topic><topic>Bornanes - isolation & purification</topic><topic>chiral HPLC</topic><topic>Chromatography, High Pressure Liquid</topic><topic>deramciclane fumarate</topic><topic>enantiomeric purity</topic><topic>stereochemistry</topic><topic>Stereoisomerism</topic><topic>X-ray analysis</topic><topic>X-Ray Diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ladányi, László</creatorcontrib><creatorcontrib>Sztruhár, Ilona</creatorcontrib><creatorcontrib>Budai, Zoltán</creatorcontrib><creatorcontrib>Lukács, Gyula</creatorcontrib><creatorcontrib>Mezei, Tibor</creatorcontrib><creatorcontrib>Argay, Gyula</creatorcontrib><creatorcontrib>Kálmán, Alajos</creatorcontrib><creatorcontrib>Simig, Gyula</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ladányi, László</au><au>Sztruhár, Ilona</au><au>Budai, Zoltán</au><au>Lukács, Gyula</au><au>Mezei, Tibor</au><au>Argay, Gyula</au><au>Kálmán, Alajos</au><au>Simig, Gyula</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>1999</date><risdate>1999</risdate><volume>11</volume><issue>9</issue><spage>689</spage><epage>693</epage><pages>689-693</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>The synthesis, stereostructure, and enantiomeric separation by chromatography of a new, chiral anxiolytic agent, deramciclane fumarate (2, (−)‐[1R,2S,4R]‐2‐(2‐dimethylaminoethoxy)‐2‐phenyl‐1,7,7‐trimethylbicyclo[2.2.1]heptane fumarate, EGIS‐3886), is described. The optical antipode and the racemate of compound 2 were also prepared. The structure was determined by single crystal X‐ray diffraction analysis. The enantiomeric separation was accomplished by HPLC on Chiralcel OD (250 × 4.6 mm; 10 μm) and hexane‐ethanol (99.5:0.5) as mobile phase at room temperature. The enantiomeric purity of the synthesized drug substance proved to be very high (>99.9%). Some statements published earlier on the stereostructure of deramciclane fumarate are critically discussed. Chirality 11:689–693, 1999. © 1999 Wiley‐Liss, Inc.</abstract><cop>New York</cop><pub>John Wiley & Sons, Inc</pub><pmid>10506429</pmid><doi>10.1002/(SICI)1520-636X(1999)11:9<689::AID-CHIR4>3.0.CO;2-X</doi><tpages>5</tpages></addata></record>
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subjects	Anti-Anxiety Agents - chemistry Anti-Anxiety Agents - isolation & purification anxiolytic agent Bornanes - chemistry Bornanes - isolation & purification chiral HPLC Chromatography, High Pressure Liquid deramciclane fumarate enantiomeric purity stereochemistry Stereoisomerism X-ray analysis X-Ray Diffraction
title	Stereochemistry and enantiomeric purity of a novel anxiolytic agent, deramciclane fumarate
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