1-((3S,4S)-4-Amino-1-(4-substituted-1,3,5-triazin-2-yl) pyrrolidin-3-yl)-5,5-difluoropiperidin-2-one inhibitors of DPP-4 for the treatment of type 2 diabetes
Kim M. Andrews
1
,
David A Beebe
1
,
John W Benbow
1
,
David A Boyer
1
,
Shawn D. Doran
1
,
Hui Yu
1
,
Shenping Liu
1
,
R Kirk McPherson
1
,
Constantin Neagu
1
,
Janice C. Parker
1
,
David W. Piotrowski
1
,
Steven R. Schneider
1
,
JUDITH L. TREADWAY
1
,
Maria A Vanvolkenberg
1
,
William J Zembrowski
1
1
Pfizer Global Research and Development, Groton Laboratories, 558 Eastern Point Road, Groton, CT 06340, United States
|
Publication type: Journal Article
Publication date: 2011-03-01
scimago Q2
wos Q2
SJR: 0.472
CiteScore: 5.1
Impact factor: 2.2
ISSN: 0960894X, 14643405
PubMed ID:
21324688
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
A 3-amino-4-substituted pyrrolidine series of dipeptidyl peptidase IV (DPP-4) inhibitors was rapidly developed into a candidate series by identification of a polar valerolactam replacement for the lipophilic 2,4,5-trifluorophenyl pharmacophore. The addition of a gem-difluoro substituent to the lactam improved overall DPP-4 inhibition and an efficient asymmetric route to 3,4-diaminopyrrolidines was developed. Advanced profiling of a subset of analogs identified 5o with an acceptable human DPP-4 inhibition profile based on a rat PK/PD model and a projected human dose that was suitable for clinical development.
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Andrews K. M. et al. 1-((3S,4S)-4-Amino-1-(4-substituted-1,3,5-triazin-2-yl) pyrrolidin-3-yl)-5,5-difluoropiperidin-2-one inhibitors of DPP-4 for the treatment of type 2 diabetes // Bioorganic and Medicinal Chemistry Letters. 2011. Vol. 21. No. 6. pp. 1810-1814.
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Andrews K. M., Beebe D. A., Benbow J. W., Boyer D. A., Doran S. D., Yu H., Liu S., McPherson R. K., Neagu C., Parker J. C., Piotrowski D. W., Schneider S. R., TREADWAY J. L., Vanvolkenberg M. A., Zembrowski W. J. 1-((3S,4S)-4-Amino-1-(4-substituted-1,3,5-triazin-2-yl) pyrrolidin-3-yl)-5,5-difluoropiperidin-2-one inhibitors of DPP-4 for the treatment of type 2 diabetes // Bioorganic and Medicinal Chemistry Letters. 2011. Vol. 21. No. 6. pp. 1810-1814.
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RIS
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TY - JOUR
DO - 10.1016/j.bmcl.2011.01.055
UR - https://doi.org/10.1016/j.bmcl.2011.01.055
TI - 1-((3S,4S)-4-Amino-1-(4-substituted-1,3,5-triazin-2-yl) pyrrolidin-3-yl)-5,5-difluoropiperidin-2-one inhibitors of DPP-4 for the treatment of type 2 diabetes
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Andrews, Kim M.
AU - Beebe, David A
AU - Benbow, John W
AU - Boyer, David A
AU - Doran, Shawn D.
AU - Yu, Hui
AU - Liu, Shenping
AU - McPherson, R Kirk
AU - Neagu, Constantin
AU - Parker, Janice C.
AU - Piotrowski, David W.
AU - Schneider, Steven R.
AU - TREADWAY, JUDITH L.
AU - Vanvolkenberg, Maria A
AU - Zembrowski, William J
PY - 2011
DA - 2011/03/01
PB - Elsevier
SP - 1810-1814
IS - 6
VL - 21
PMID - 21324688
SN - 0960-894X
SN - 1464-3405
ER -
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BibTex (up to 50 authors)
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@article{2011_Andrews,
author = {Kim M. Andrews and David A Beebe and John W Benbow and David A Boyer and Shawn D. Doran and Hui Yu and Shenping Liu and R Kirk McPherson and Constantin Neagu and Janice C. Parker and David W. Piotrowski and Steven R. Schneider and JUDITH L. TREADWAY and Maria A Vanvolkenberg and William J Zembrowski},
title = {1-((3S,4S)-4-Amino-1-(4-substituted-1,3,5-triazin-2-yl) pyrrolidin-3-yl)-5,5-difluoropiperidin-2-one inhibitors of DPP-4 for the treatment of type 2 diabetes},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2011},
volume = {21},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/j.bmcl.2011.01.055},
number = {6},
pages = {1810--1814},
doi = {10.1016/j.bmcl.2011.01.055}
}
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MLA
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Andrews, Kim M., et al. “1-((3S,4S)-4-Amino-1-(4-substituted-1,3,5-triazin-2-yl) pyrrolidin-3-yl)-5,5-difluoropiperidin-2-one inhibitors of DPP-4 for the treatment of type 2 diabetes.” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 6, Mar. 2011, pp. 1810-1814. https://doi.org/10.1016/j.bmcl.2011.01.055.