Lai ZW, Li C, Liu J, Kong L, Wen X, Sun H. Discovery of highly potent DPP-4 inhibitors by hybrid compound design based on linagliptin and alogliptin. Eur J Med Chem. 2014;83:547–60. https://doi.org/10.1016/j.ejmech.2014.06.044
Article CAS PubMed Google Scholar
Sneha P, Doss CGP. Gliptins in managing diabetes - reviewing computational strategy. Life Sci. 2016;166:108–20. https://doi.org/10.1016/j.lfs.2016.10.009
Article CAS PubMed Google Scholar
Hu N, Zhao G, Zhang Y, Liu X, Li G, Tang W. Synthesis of chiral α-amino tertiary boronic esters by enantioselective hydroboration of α-arylenamides. J Am Chem Soc. 2015;137:6746–9. https://doi.org/10.1021/jacs.5b03760
Article CAS PubMed Google Scholar
Plescia J, Moitessier N. Design and discovery of boronic acid drugs. Eur J Med Chem. 2020;195:112270. https://doi.org/10.1016/j.ejmech.2020.112270
Article CAS PubMed Google Scholar
Kim MK, Chae YN, Kim HD, Yang EK, Cho EJ, Choi SH, et al. DA-1229, a novel and potent DPP-4 inhibitor, improves insulin resistance and delays the onset of diabetes. Life Sci. 2012;90:21–29. https://doi.org/10.1016/j.lfs.2011.10.007
Article CAS PubMed Google Scholar
Choi SH, Park S, Oh CJ, Leem J, Park KG, Lee IK, et al. Dipeptidyl peptidase-4 inhibition by gemigliptin prevents abnormal vascular remodeling via NF-E2-related factor 2 activation. Vasc Pharmacol 2015;73:11–19. https://doi.org/10.1016/j.vph.2015.07.005
Shu C, Ge H, Song M, Chen JH, Zhou H, Qi Q, et al. Discovery of imigliptin, a novel selective DPP-4 inhibitor for the treatment of type 2 diabetes. ACS Med Chem Lett 2014;5:921–6. https://doi.org/10.1021/ml5001905
Article CAS PubMed PubMed Central Google Scholar
Hou A, Deng Z, Ma H, Liu T. Substrate screening of amino transaminase for the synthesis of a sitagliptin intermediate. Tetrahedron. 2016;72:4660–4. https://doi.org/10.1016/j.tet.2016.06.039
Zhou Y, Liu Y, Wang X, He X, Wang Y. Method for preparing an important intermediate of Linagliptn. US patent. 2016;9:522–915 B2.
Łupina M, Talarek S, Kotlińska J, Gibuła-Tarłowska E, Listos P, Listos J, et al. The role of linagliptin, a selective dipeptidyl peptidase-4 inhibitor, in the morphine rewarding effects in rats. Neurochem Int 2020;133:1–9. https://doi.org/10.1016/j.neuint.2019.104616
Sarashina A, Chiba K, Tatami S, Kato Y. Physiologically based pharmacokinetic model of the DPP-4 inhibitor linagliptin to describe its nonlinear pharmacokinetics in humans. J Pharm Sci. 2020;109:2336–44. https://doi.org/10.1016/j.xphs.2020.03.031
Article CAS PubMed Google Scholar
Chung JY, Scott JP, Anderson C, Bishop B, Bremeyer N, Cao Y, et al. Evolution of a manufacturing route to omarigliptin, a long-acting DPP-4 inhibitor for the treatment of type 2 diabetes. Org Process Res Dev 2015;19:1760–8. https://doi.org/10.1021/acs.oprd.5b00267
Barnett A. DPP-4 inhibitors and their potential role in the management of type 2 diabetes. Int J Clin Pr. 2006;60:1454–70. https://doi.org/10.1111/j.1742-1241.2006.01178.x
Peng F, Chen Y, Chen CY, Dormer PG, Kassim A, McLaughlin M, et al. Asymmetric formal synthesis of the long-acting DPP-4 inhibitor omarigliptin. J Org Chem. 2017;82:9023–9. https://doi.org/10.1021/acs.joc.7b01467
Article CAS PubMed PubMed Central Google Scholar
Savage SA, Jones GS, Kolotuchin S, Ramrattan SA, Vu T, Waltermire RE, et al. Preparation of saxagliptin, a novel DPP-IV inhibitor. Org Process Res Dev 2009;13:1169–76. https://doi.org/10.1021/op900226j
Li N, Wang LJ, Jiang B, Guo SJ, Li XQ, Chen XC, et al. Design, synthesis and biological evaluation of novel pyrimidinedione derivatives as DPP-4 inhibitors. Bioorg Med Chem Lett. 2018;28:2131–5. https://doi.org/10.1016/j.bmcl.2018.05.022
Article CAS PubMed Google Scholar
Liao Q, Jiang L, Li C, Shen Y, Wang M, Cao C, et al. An Efficient and practical method for the synthesis of saxagliptin intermediate 2-(3-Hydroxy-1-adamantane)-2-oxoacetic acid and its optimization. J Chem. 2019. https://doi.org/10.1155/2019/5375670
Ceriello A, Sportiello L, Rafaniello C, Rossi F. DPP-4 inhibitors: pharmacological differences and their clinical implications. Expert Opin Drug Saf. 2014;13:57–68. https://doi.org/10.1517/14740338.2014.944862
Subbaiah CS, Haq W. Efficient stereocontrolled synthesis of sitagliptin phosphate. Tetrahedron Asymmetry. 2014;25:1026–30. https://doi.org/10.1016/j.tetasy.2014.06.001
Lombardi A, Concepcion E, Hou H, Arib H, Mezei M, Osman R, et al. Retro-inverso D-peptides as a novel targeted immunotherapy for Type 1 diabetes. J Autoimmun. 2020;115:102543. https://doi.org/10.1016/j.jaut.2020.102543
Article CAS PubMed PubMed Central Google Scholar
Kang SK, Cho GH, Leem HJ, Soh BK, Sim J, Suh YG, et al. A highly stereoselective and efficient synthesis of enantiomerically pure sitagliptin. Tetrahedron Asymmetry. 2017;28:34–40. https://doi.org/10.1016/j.tetasy.2016.10.010
Deng X, Shen J, Zhu H, Xiao J, Sun R, Xie F, et al. Surrogating and redirection of pyrazolo[1,5-a]pyrimidin-7(4H)-one core, a novel class of potent and selective DPP-4 inhibitors. Bioorg Med Chem 2018;26:903–12. https://doi.org/10.1016/j.bmc.2018.01.006
Article CAS PubMed Google Scholar
Xie Y, Shao L, Wang Q, Bai Y, Chen Z, Li N, et al. Synthesis, nitric oxide release, and dipeptidyl peptidase-4 inhibition of sitagliptin derivatives as new multifunctional antidiabetic agents. Bioorg Med Chem Lett. 2018;28:3731–5. https://doi.org/10.1016/j.bmcl.2018.10.019
Article CAS PubMed Google Scholar
Bae HY, Kim MJ, Sim JH, Song CE. Direct catalytic asymmetric mannich reaction with dithiomalonates as excellent mannich donors: organocatalytic Synthesis of (R)-Sitagliptin. Angew Chem Int Ed Engl. 2016;55:10825–9. https://doi.org/10.1002/anie.201605167.
Article CAS PubMed Google Scholar
Kim GH, Jeon H, Khobragade TP, Patil MD, Sung S, Yoon S, et al. Enzymatic synthesis of sitagliptin intermediate using a novel ω-transaminase. Enzym Microb Technol 2019;120:52–60. https://doi.org/10.1016/j.enzmictec.2018.10.003
Kumar N, Devineni SR, Aggile K, Gajjala PR, Kumar P, Dubey SK, et al. Facile new industrial process for synthesis of teneligliptin through new intermediates and its optimization with control of impurities. Res Chem Intermed 2018;44:567–84. https://doi.org/10.1007/s11164-017-3120-3
Xie H, Zeng S, He Y, Zhang G, Yu P, Zhong G, et al. Rapid generation of a novel DPP-4 inhibitor with long-acting properties: SAR study and PK/PD evaluation. Eur J Med Chem. 2017;141:519–29. https://doi.org/10.1016/j.ejmech.2017.10.029
Article CAS PubMed Google Scholar
Hrdina R, Metz FM, Larrosa M, Berndt JP, Zhygadlo YY, Becker S, et al. Intramolecular C-H amination reaction provides direct access to 1,2-disubstituted diamondoids. Eur J Org Chem 2015;2015:6231–6. https://doi.org/10.1002/ejoc.201500691
Castaldi M, Baratella M, Menegotto IG, Castaldi G, Giovenzana GB. A concise and efficient synthesis of vildagliptin. Tetrahedron Lett. 2017;58:3426–8. https://doi.org/10.1016/j.tetlet.2017.07.062
Rommelmann P, Betke T, Gröger H. Synthesis of enantiomerically pure N-Acyl amino nitriles via catalytic dehydration of oximes and application in a de novo synthesis of vildagliptin. Org Process Res Dev 2017;21:1521–7. https://doi.org/10.1021/acs.oprd.7b00169
留言 (0)