Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles
The discovery and SAR studies of a series of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as novel μ opioid receptor antagonists, analogs of alvimopan, are reported. A series of N-substituted trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2008-03, Vol.18 (6), p.2006-2012 |
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| container_end_page | 2012 |
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| container_issue | 6 |
| container_start_page | 2006 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 18 |
| creator | Le Bourdonnec, Bertrand Barker, William M. Belanger, Serge Wiant, Daniel D. Conway-James, Nathalie C. Cassel, Joel A. O’Neill, Timothy J. Little, Patrick J. DeHaven, Robert N. DeHaven-Hudkins, Diane L. Dolle, Roland E. |
| description | The discovery and SAR studies of a series of
N-substituted
trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as novel μ opioid receptor antagonists, analogs of alvimopan, are reported.
A series of
N-substituted
trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective μ opioid receptor antagonist, which interacts selectively with μ peripheral receptors. |
| doi_str_mv | 10.1016/j.bmcl.2008.01.106 |
| format | Article |
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N-substituted
trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as novel μ opioid receptor antagonists, analogs of alvimopan, are reported.
A series of
N-substituted
trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective μ opioid receptor antagonist, which interacts selectively with μ peripheral receptors.</description><identifier>ISSN: 0960-894X</identifier><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3405</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmcl.2008.01.106</identifier><identifier>PMID: 18313920</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Administration, Oral ; Animals ; Biological and medical sciences ; Cell Membrane - metabolism ; Central Nervous System - drug effects ; Chromatography, High Pressure Liquid ; Diprenorphine - metabolism ; Gastrointestinal Transit - drug effects ; Guanosine 5'-O-(3-Thiotriphosphate) - metabolism ; Humans ; Loperamide - pharmacology ; Medical sciences ; Mice ; Molecular Structure ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Opioid ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Pharmacology. Drug treatments ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Piperidines - pharmacology ; Receptors, Opioid, delta - antagonists & inhibitors ; Receptors, Opioid, delta - metabolism ; Receptors, Opioid, kappa - antagonists & inhibitors ; Receptors, Opioid, kappa - metabolism ; Receptors, Opioid, mu - antagonists & inhibitors ; Receptors, Opioid, mu - metabolism ; Solid phase synthesis ; Structure-Activity Relationship ; μ receptors</subject><ispartof>Bioorganic & medicinal chemistry, 2008-03, Vol.18 (6), p.2006-2012</ispartof><rights>2008 Elsevier Ltd</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-c204daed5177b61ad9e4d216673441a27837108554bab4388ee5e5d94ac97b593</citedby><cites>FETCH-LOGICAL-c415t-c204daed5177b61ad9e4d216673441a27837108554bab4388ee5e5d94ac97b593</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X08001339$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20217239$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18313920$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Le Bourdonnec, Bertrand</creatorcontrib><creatorcontrib>Barker, William M.</creatorcontrib><creatorcontrib>Belanger, Serge</creatorcontrib><creatorcontrib>Wiant, Daniel D.</creatorcontrib><creatorcontrib>Conway-James, Nathalie C.</creatorcontrib><creatorcontrib>Cassel, Joel A.</creatorcontrib><creatorcontrib>O’Neill, Timothy J.</creatorcontrib><creatorcontrib>Little, Patrick J.</creatorcontrib><creatorcontrib>DeHaven, Robert N.</creatorcontrib><creatorcontrib>DeHaven-Hudkins, Diane L.</creatorcontrib><creatorcontrib>Dolle, Roland E.</creatorcontrib><title>Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The discovery and SAR studies of a series of
N-substituted
trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as novel μ opioid receptor antagonists, analogs of alvimopan, are reported.
A series of
N-substituted
trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective μ opioid receptor antagonist, which interacts selectively with μ peripheral receptors.</description><subject>Administration, Oral</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cell Membrane - metabolism</subject><subject>Central Nervous System - drug effects</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Diprenorphine - metabolism</subject><subject>Gastrointestinal Transit - drug effects</subject><subject>Guanosine 5'-O-(3-Thiotriphosphate) - metabolism</subject><subject>Humans</subject><subject>Loperamide - pharmacology</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Opioid</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Receptors, Opioid, delta - antagonists & inhibitors</subject><subject>Receptors, Opioid, delta - metabolism</subject><subject>Receptors, Opioid, kappa - antagonists & inhibitors</subject><subject>Receptors, Opioid, kappa - metabolism</subject><subject>Receptors, Opioid, mu - antagonists & inhibitors</subject><subject>Receptors, Opioid, mu - metabolism</subject><subject>Solid phase synthesis</subject><subject>Structure-Activity Relationship</subject><subject>μ receptors</subject><issn>0960-894X</issn><issn>0968-0896</issn><issn>1464-3405</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcuKFDEUhoMoTjv6Ai6kNoqCaU8qSV3AzTB4g0E3Cu5CKjltp0ldTNLt1Dv4SPMMPpMputHFgK4Chy__n5yPkMcM1gxY9Wq37nrj1yVAswaWZ9UdsmKiEpQLkHfJCtoKaNOKr2fkQYw7ACZAiPvkjDWc8baEFfn5cTygL1LQQ6T8paDW9Zi2s6eCPud0O9swXs_TFofZv5jchMFZN2AsdCx-3RTj5EZni4AGpzSGQg9JfxsHF1Msfri0LVw_hdxgb5ERPZrkDi7NRUY2zmN8SO5ttI_46HSeky9v33y-fE-vPr37cHlxRY1gMlFTgrAarWR13VVM2xaFLVlV1VwIpsu64TWDRkrR6U7wpkGUKG0rtGnrTrb8nDw75ubi73uMSfUuGvReDzjuo6pBAJdQ_RdkLc-VrcxgeQRNGGMMuFFTcL0Os2KgFllqpxZZapGlgOXZkv7klL7verR_r5zsZODpCdDRaL_JkoyLf7gSSlaXfPnP6yOHeWkHh0FF43AwaF3ed1J2dP96x29lgLV0</recordid><startdate>20080315</startdate><enddate>20080315</enddate><creator>Le Bourdonnec, Bertrand</creator><creator>Barker, William M.</creator><creator>Belanger, Serge</creator><creator>Wiant, Daniel D.</creator><creator>Conway-James, Nathalie C.</creator><creator>Cassel, Joel A.</creator><creator>O’Neill, Timothy J.</creator><creator>Little, Patrick J.</creator><creator>DeHaven, Robert N.</creator><creator>DeHaven-Hudkins, Diane L.</creator><creator>Dolle, Roland E.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20080315</creationdate><title>Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles</title><author>Le Bourdonnec, Bertrand ; Barker, William M. ; Belanger, Serge ; Wiant, Daniel D. ; Conway-James, Nathalie C. ; Cassel, Joel A. ; O’Neill, Timothy J. ; Little, Patrick J. ; DeHaven, Robert N. ; DeHaven-Hudkins, Diane L. ; Dolle, Roland E.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-c204daed5177b61ad9e4d216673441a27837108554bab4388ee5e5d94ac97b593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Administration, Oral</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cell Membrane - metabolism</topic><topic>Central Nervous System - drug effects</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Diprenorphine - metabolism</topic><topic>Gastrointestinal Transit - drug effects</topic><topic>Guanosine 5'-O-(3-Thiotriphosphate) - metabolism</topic><topic>Humans</topic><topic>Loperamide - pharmacology</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Opioid</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Piperidines - pharmacology</topic><topic>Receptors, Opioid, delta - antagonists & inhibitors</topic><topic>Receptors, Opioid, delta - metabolism</topic><topic>Receptors, Opioid, kappa - antagonists & inhibitors</topic><topic>Receptors, Opioid, kappa - metabolism</topic><topic>Receptors, Opioid, mu - antagonists & inhibitors</topic><topic>Receptors, Opioid, mu - metabolism</topic><topic>Solid phase synthesis</topic><topic>Structure-Activity Relationship</topic><topic>μ receptors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Le Bourdonnec, Bertrand</creatorcontrib><creatorcontrib>Barker, William M.</creatorcontrib><creatorcontrib>Belanger, Serge</creatorcontrib><creatorcontrib>Wiant, Daniel D.</creatorcontrib><creatorcontrib>Conway-James, Nathalie C.</creatorcontrib><creatorcontrib>Cassel, Joel A.</creatorcontrib><creatorcontrib>O’Neill, Timothy J.</creatorcontrib><creatorcontrib>Little, Patrick J.</creatorcontrib><creatorcontrib>DeHaven, Robert N.</creatorcontrib><creatorcontrib>DeHaven-Hudkins, Diane L.</creatorcontrib><creatorcontrib>Dolle, Roland E.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Le Bourdonnec, Bertrand</au><au>Barker, William M.</au><au>Belanger, Serge</au><au>Wiant, Daniel D.</au><au>Conway-James, Nathalie C.</au><au>Cassel, Joel A.</au><au>O’Neill, Timothy J.</au><au>Little, Patrick J.</au><au>DeHaven, Robert N.</au><au>DeHaven-Hudkins, Diane L.</au><au>Dolle, Roland E.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2008-03-15</date><risdate>2008</risdate><volume>18</volume><issue>6</issue><spage>2006</spage><epage>2012</epage><pages>2006-2012</pages><issn>0960-894X</issn><issn>0968-0896</issn><eissn>1464-3405</eissn><eissn>1464-3391</eissn><abstract>The discovery and SAR studies of a series of
N-substituted
trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as novel μ opioid receptor antagonists, analogs of alvimopan, are reported.
A series of
N-substituted
trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines, μ opioid receptor antagonists, analogs of alvimopan, were prepared using solid phase methodology. This study led to the identification of a highly selective μ opioid receptor antagonist, which interacts selectively with μ peripheral receptors.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>18313920</pmid><doi>10.1016/j.bmcl.2008.01.106</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry, 2008-03, Vol.18 (6), p.2006-2012 |
| issn | 0960-894X 0968-0896 1464-3405 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Administration, Oral Animals Biological and medical sciences Cell Membrane - metabolism Central Nervous System - drug effects Chromatography, High Pressure Liquid Diprenorphine - metabolism Gastrointestinal Transit - drug effects Guanosine 5'-O-(3-Thiotriphosphate) - metabolism Humans Loperamide - pharmacology Medical sciences Mice Molecular Structure Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Opioid Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Receptors, Opioid, delta - antagonists & inhibitors Receptors, Opioid, delta - metabolism Receptors, Opioid, kappa - antagonists & inhibitors Receptors, Opioid, kappa - metabolism Receptors, Opioid, mu - antagonists & inhibitors Receptors, Opioid, mu - metabolism Solid phase synthesis Structure-Activity Relationship μ receptors |
| title | Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles |
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