Structure and property based design of factor Xa inhibitors: Biaryl pyrrolidin-2-ones incorporating basic heterocyclic motifs
Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles. S...
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| Published in: | Bioorganic & medicinal chemistry Vol. 18; no. 1; pp. 28 - 33 |
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| Main Authors: | , , , , , , , , , , , , , , , , , , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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2008
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| Abstract | Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles.
Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles. |
|---|---|
| AbstractList | Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles. Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles. Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles. |
| Author | Zhou, Ping Mason, Andrew M. Young, Robert J. Kelly, Henry A. Kleanthous, Savvas Senger, Stefan Convery, Máire A. Burns-Kurtis, Cynthia L. Diallo, Hawa King, N. Paul Charbaut, Marie Weston, Helen E. Campbell, Matthew Irving, Wendy R. Pollard, Derek R. Toomey, John R. Pinto, Ivan L. Brown, David Pateman, Anthony J. Borthwick, Alan D. Watson, Nigel S. Hortense, Eric Patikis, Angela N. Shah, Gita P. Chan, Chuen |
| Author_xml | – sequence: 1 givenname: Robert J. surname: Young fullname: Young, Robert J. email: Rob.J.Young@gsk.com organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 2 givenname: Alan D. surname: Borthwick fullname: Borthwick, Alan D. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 3 givenname: David surname: Brown fullname: Brown, David organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 4 givenname: Cynthia L. surname: Burns-Kurtis fullname: Burns-Kurtis, Cynthia L. organization: GlaxoSmithKline, 709 Swedeland Road, King of Prussia, PA 19406, USA – sequence: 5 givenname: Matthew surname: Campbell fullname: Campbell, Matthew organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 6 givenname: Chuen surname: Chan fullname: Chan, Chuen organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 7 givenname: Marie surname: Charbaut fullname: Charbaut, Marie organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 8 givenname: Máire A. surname: Convery fullname: Convery, Máire A. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 9 givenname: Hawa surname: Diallo fullname: Diallo, Hawa organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 10 givenname: Eric surname: Hortense fullname: Hortense, Eric organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 11 givenname: Wendy R. surname: Irving fullname: Irving, Wendy R. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 12 givenname: Henry A. surname: Kelly fullname: Kelly, Henry A. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 13 givenname: N. Paul surname: King fullname: King, N. Paul organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 14 givenname: Savvas surname: Kleanthous fullname: Kleanthous, Savvas organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 15 givenname: Andrew M. surname: Mason fullname: Mason, Andrew M. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 16 givenname: Anthony J. surname: Pateman fullname: Pateman, Anthony J. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 17 givenname: Angela N. surname: Patikis fullname: Patikis, Angela N. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 18 givenname: Ivan L. surname: Pinto fullname: Pinto, Ivan L. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 19 givenname: Derek R. surname: Pollard fullname: Pollard, Derek R. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 20 givenname: Stefan surname: Senger fullname: Senger, Stefan organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 21 givenname: Gita P. surname: Shah fullname: Shah, Gita P. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 22 givenname: John R. surname: Toomey fullname: Toomey, John R. organization: GlaxoSmithKline, 709 Swedeland Road, King of Prussia, PA 19406, USA – sequence: 23 givenname: Nigel S. surname: Watson fullname: Watson, Nigel S. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 24 givenname: Helen E. surname: Weston fullname: Weston, Helen E. organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom – sequence: 25 givenname: Ping surname: Zhou fullname: Zhou, Ping organization: GlaxoSmithKline, Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, United Kingdom |
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| Cites_doi | 10.1016/j.bmcl.2006.04.053 10.1016/j.bmcl.2003.12.053 10.1016/j.bmcl.2006.08.027 10.2174/1381612033453901 10.2165/00129784-200505050-00001 10.1016/j.bmcl.2007.03.080 10.1021/jm060870c 10.1016/j.bmcl.2006.09.001 10.1182/blood-2003-12-4195 10.1248/cpb.41.478 10.1246/cl.1988.899 10.2174/0929867013372643 10.1177/0091270005278084 10.1016/j.bmcl.2006.01.010 10.3987/COM-96-7489 10.1021/jm0497949 10.1002/jps.10494 |
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| Keywords | Oral inhibitors Factor Xa Imidazole derivatives Intravenous administration Rat Coagulation Factor Xa Anticoagulant Pyrrolidine derivatives Thiophene derivatives Structure activity relation Chlorine Organic compounds Antithrombotic agent Chemical synthesis Sulfonamide Serine endopeptidases Enzyme Rodentia Oral administration Enzyme inhibitor In vitro Peptidases In vivo Vertebrata Mammalia Animal Tertiary amine Hydrolases Benzenic compound Fluorine Organic compounds Pharmacokinetics |
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| SubjectTerms | Animals Anticoagulants - chemistry Anticoagulants - pharmacokinetics Anticoagulants - pharmacology Biological and medical sciences Blood. Blood coagulation. Reticuloendothelial system Bridged Bicyclo Compounds, Heterocyclic - chemistry Bridged Bicyclo Compounds, Heterocyclic - pharmacokinetics Bridged Bicyclo Compounds, Heterocyclic - pharmacology Factor Xa Factor Xa Inhibitors Hydrophobic and Hydrophilic Interactions Male Medical sciences Models, Molecular Oral inhibitors Pharmacology. Drug treatments Pyrrolidinones - chemistry Pyrrolidinones - pharmacokinetics Pyrrolidinones - pharmacology Rats Rats, Sprague-Dawley Serine Proteinase Inhibitors - chemistry Serine Proteinase Inhibitors - pharmacokinetics Serine Proteinase Inhibitors - pharmacology Stereoisomerism Structure-Activity Relationship |
| Title | Structure and property based design of factor Xa inhibitors: Biaryl pyrrolidin-2-ones incorporating basic heterocyclic motifs |
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