Balancing potency, metabolic stability and permeability in pyrrolopyrimidine-based EGFR inhibitors.

[1]  K. Nørsett,et al.  Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors. , 2016, European journal of medicinal chemistry.

[2]  L. Olsen,et al.  Enthalpy-Entropy Compensation in the Binding of Modulators at Ionotropic Glutamate Receptor GluA2. , 2016, Biophysical journal.

[3]  B. Hoff,et al.  In vitro baselining of new pyrrolopyrimidine EGFR-TK inhibitors with Erlotinib. , 2015, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[4]  B. Hoff,et al.  Truncated structures used in search for new lead compounds and in a retrospective analysis of thienopyrimidine-based EGFR inhibitors. , 2015, European journal of medicinal chemistry.

[5]  Y. Yosaatmadja,et al.  1.85 angstrom structure of EGFR kinase domain with gefitinib , 2014 .

[6]  H. Kim,et al.  Prognostic and predictive values of EGFR overexpression and EGFR copy number alteration in HER2-positive breast cancer , 2014, British Journal of Cancer.

[7]  Xingrong Liu,et al.  Rational use of plasma protein and tissue binding data in drug design. , 2014, Journal of medicinal chemistry.

[8]  G. Bjørkøy,et al.  Identification of new 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines as highly potent EGFR-TK inhibitors with Src-family activity. , 2014, European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.

[9]  M. Moore,et al.  Assessing the role of the EGF receptor in the development and progression of pancreatic cancer , 2014 .

[10]  U. Nonstad,et al.  Structure-activity study leading to identification of a highly active thienopyrimidine based EGFR inhibitor. , 2014, European journal of medicinal chemistry.

[11]  J. Rubio-Martínez,et al.  Microwave‐Assisted Synthesis of Substituted Pyrrolo[2,3‐d]pyrimidines , 2014 .

[12]  Z. O’Brien,et al.  Small molecule kinase inhibitors approved by the FDA from 2000 to 2011: a systematic review of preclinical ADME data , 2013, Expert opinion on drug metabolism & toxicology.

[13]  W. Pao,et al.  Mechanism for activation of mutated epidermal growth factor receptors in lung cancer , 2013, Proceedings of the National Academy of Sciences.

[14]  E. Sausville,et al.  Phase 1 dose-escalation, pharmacokinetic, and cerebrospinal fluid distribution study of TAK-285, an investigational inhibitor of EGFR and HER2 , 2013, Investigational New Drugs.

[15]  Daisuke Kitagawa,et al.  Activity‐based kinase profiling of approved tyrosine kinase inhibitors , 2013, Genes to cells : devoted to molecular & cellular mechanisms.

[16]  A. Ardizzoni,et al.  Combined use of anti-ErbB monoclonal antibodies and erlotinib enhances antibody-dependent cellular cytotoxicity of wild-type erlotinib-sensitive NSCLC cell lines , 2012, Molecular Cancer.

[17]  Thomas J. Raub,et al.  How hydrogen bonds impact P-glycoprotein transport and permeability. , 2012, Bioorganic & medicinal chemistry letters.

[18]  Toshimasa Tanaka,et al.  Design and synthesis of pyrrolo[3,2-d]pyrimidine HER2/EGFR dual inhibitors: improvement of the physicochemical and pharmacokinetic profiles for potent in vivo anti-tumor efficacy. , 2012, Bioorganic & medicinal chemistry.

[19]  Hongjian Xu,et al.  Novel pyrrolopyrimidine analogues as potent dipeptidyl peptidase IV inhibitors based on pharmacokinetic property-driven optimization. , 2012, European journal of medicinal chemistry.

[20]  C. Fotsch,et al.  Mitigating heterocycle metabolism in drug discovery. , 2012, Journal of medicinal chemistry.

[21]  K. Linton,et al.  Investigational ABC transporter inhibitors , 2012, Expert opinion on investigational drugs.

[22]  A. Ohtsu,et al.  Phase I first-in-human study of TAK-285, a novel investigational dual HER2/EGFR inhibitor, in cancer patients , 2012, British Journal of Cancer.

[23]  G. Bjørkøy,et al.  Synthesis and in vitro EGFR (ErbB1) tyrosine kinase inhibitory activity of 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines. , 2011, European journal of medicinal chemistry.

[24]  Masashi Honma,et al.  Off-Target Serine/Threonine Kinase 10 Inhibition by Erlotinib Enhances Lymphocytic Activity Leading to Severe Skin Disorders , 2011, Molecular Pharmacology.

[25]  N. Meanwell.  Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. , 2011, Chemical research in toxicology.

[26]  S. Rees,et al.  Principles of early drug discovery , 2011, British journal of pharmacology.

[27]  William Pao,et al.  Rational, biologically based treatment of EGFR-mutant non-small-cell lung cancer , 2010, Nature Reviews Cancer.

[28]  P. Marathe,et al.  Preclinical pharmacokinetics and in vitro metabolism of BMS-690514, a potent inhibitor of EGFR and VEGFR2. , 2010, Journal of pharmaceutical sciences.

[29]  M. Hewitt,et al.  The kinetic isotope effect in the search for deuterated drugs. , 2010, Drug news & perspectives.

[30]  G. Mills,et al.  Targeting the Epidermal Growth Factor Receptor in Epithelial Ovarian Cancer: Current Knowledge and Future Challenges , 2009, Journal of oncology.

[31]  Vijay T. Ahuja,et al.  A strategy to minimize reactive metabolite formation: discovery of (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-[6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino]-5-oxo-4,5-dihydropyrazine-2-carbonitrile as a potent, orally bioavailable corticotropin-releasing factor-1 receptor antagonist. , 2009, Journal of medicinal chemistry.

[32]  M. Watson,et al.  Correlating EGFR Expression with Receptor-Binding Properties and Internalization of 64Cu-DOTA-Cetuximab in 5 Cervical Cancer Cell Lines , 2008, Journal of Nuclear Medicine.

[33]  S. Buchwald,et al.  An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane. , 2008, The Journal of organic chemistry.

[34]  P. Cohen,et al.  The selectivity of protein kinase inhibitors: a further update. , 2007, The Biochemical journal.

[35]  P. Graczyk.  Gini coefficient: a new way to express selectivity of kinase inhibitors against a family of kinases. , 2007, Journal of medicinal chemistry.

[36]  M. Verdonk,et al.  A comparison of physicochemical property profiles of marketed oral drugs and orally bioavailable anti-cancer protein kinase inhibitors in clinical development. , 2007, Current topics in medicinal chemistry.

[37]  Joelle M. R. Gola,et al.  Focus on success: using a probabilistic approach to achieve an optimal balance of compound properties in drug discovery , 2006, Expert opinion on drug metabolism & toxicology.

[38]  C. Prakash,et al.  METABOLISM AND EXCRETION OF ERLOTINIB, A SMALL MOLECULE INHIBITOR OF EPIDERMAL GROWTH FACTOR RECEPTOR TYROSINE KINASE, IN HEALTHY MALE VOLUNTEERS , 2006, Drug Metabolism and Disposition.

[39]  R. Friesner,et al.  Novel procedure for modeling ligand/receptor induced fit effects. , 2006, Journal of medicinal chemistry.

[40]  Woody Sherman,et al.  Use of an Induced Fit Receptor Structure in Virtual Screening , 2006, Chemical biology & drug design.

[41]  C. Laggner,et al.  Why drugs fail--a study on side effects in new chemical entities. , 2005, Current pharmaceutical design.

[42]  C. Bucana,et al.  AEE788, a Dual Tyrosine Kinase Receptor Inhibitor, Induces Endothelial Cell Apoptosis in Human Cutaneous Squamous Cell Carcinoma Xenografts in Nude Mice , 2005, Clinical Cancer Research.

[43]  L. Bubendorf,et al.  Expression patterns of potential therapeutic targets in prostate cancer , 2005, International journal of cancer.

[44]  John N Weinstein,et al.  Predicting drug sensitivity and resistance: profiling ABC transporter genes in cancer cells. , 2004, Cancer cell.

[45]  J. Mestan,et al.  AEE788: a dual family epidermal growth factor receptor/ErbB2 and vascular endothelial growth factor receptor tyrosine kinase inhibitor with antitumor and antiangiogenic activity. , 2004, Cancer research.

[46]  P. Traxler.  Tyrosine kinases as targets in cancer therapy – successes and failures , 2003, Expert opinion on therapeutic targets.

[47]  Arun K Mandagere,et al.  Graphical model for estimating oral bioavailability of drugs in humans and other species from their Caco-2 permeability and in vitro liver enzyme metabolic stability rates. , 2002, Journal of medicinal chemistry.

[48]  M. Birrer,et al.  FHIT gene expression in human ovarian, endometrial, and cervical cancer cell lines. , 1997, Cancer research.

[49]  J D Dunitz,et al.  Win some, lose some: enthalpy-entropy compensation in weak intermolecular interactions. , 1995, Chemistry & biology.

[50]  K. Münger,et al.  The state of the p53 and retinoblastoma genes in human cervical carcinoma cell lines. , 1991, Proceedings of the National Academy of Sciences of the United States of America.

[51]  B. Ozanne,et al.  Human squamous cell lung cancers express increased epidermal growth factor receptors. , 1984, The Journal of clinical investigation.

[52]  Mindy I. Davis,et al.  A quantitative analysis of kinase inhibitor selectivity , 2008, Nature Biotechnology.