Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 1
326
Views
4
CrossRef citations to date
0
Altmetric
Synthetic Communications Reviews

A short review on synthetic strategies toward glitazone drugs

ORCID Icon, &
Pages 57-80 | Received 17 Jul 2020, Published online: 07 Oct 2020

References

  • Bowen, J. P.; Zhong, H. A. Perspectives in Medicinal Chemistry: The Evolution of Medicinal Chemistry. Curr. Top. Med. Chem. 2016, 16, 897–898. DOI: 10.2174/1568026616999151029114013.
  • American Diabetes Association (ADA), Diabetes Basics. Facts About Type 2; 2020.
  • Aarag, B.; Hussein, W.; Ibrahim, W.; Zahran, M. J. Diabet. Metab. 2017, 8, 1–8.
  • Roberto, M.; Palone, T. J. Diabet. Metab. Market Anal. 2019, 10, 1–2.
  • Aguillón, A. R.; Mascarello, A.; Segretti, N. D.; Z de Azevedo, H. F.; Guimaraes, C. R. W.; Miranda, L. S. M.; De Souza, R. O. M. A. Synthetic Strategies toward SGLT2 Inhibitors. Org. Proc. Res. Dev. 2018, 22, 467–488. DOI: 10.1021/acs.oprd.8b00017.
  • Aguillón, A. R.; Mascarello, A.; Segretti, N. D.; de Azevedo, H. F. Z.; Guimaraes, C. R. W.; Miranda, L. S. M.; de Souza, R. O. M. A. Correction to “Synthetic Strategies toward SGLT2 Inhibitors. Org. Proc. Res. Dev. 2019, 23, 1471–1475. DOI: 10.1021/acs.oprd.9b00145.
  • Goerdeler, J.; Horstmann, H. Über Die Acylierung Von Thiobenzamid, II. Umsetzungen Mit Dicarbonsäure-Dichloriden. Chem. Ber. 1960, 93, 671–678. DOI: 10.1002/cber.19600930321.
  • Lesyk, R. B.; Zimenkovsky, B. S. 4-Thiazolidones: Centenarian History, Current Status and Perspectives for Modern Organic and Medicinal Chemistry. Curr. Organic Chem. 2004, 8, 1547–1577. DOI: 10.2174/1385272043369773.
  • Davidson, M. A.; Mattison, D. R.; Azoulay, L.; Krewski, D. Thiazolidinedione Drugs in the Treatment of Type 2 Diabetes Mellitus: Past, Present and Future. Crit. Rev. Toxicol. 2018, 48, 52–108. DOI: 10.1080/10408444.2017.1351420.
  • Gale, E. A. Lessons from the Glitazones: A Story of Drug Development. Lancet 2001, 357, 1870–1875. DOI: 10.1016/S0140-6736(00)04960-6.
  • Lee, M. A.; Tan, L.; Yang, H.; Im, Y.-G.; Im, Y. J. Yeong-Gwan, I.; Young Jun. Sci. Rep. 2017, 7, 168311–168371. DOI: 10.1038/s41598-017-17082-x.
  • Lee, J. Y.; Cho, Y.; Lee, M.; Lee, Y. H.; Lee, B. W.; Kang, E. S.; Cha, B. S. Clinical Efficacy of the Novel Thiazolidinedione Lobeglitazone in Patients with Type 2 Diabetes. Diabetes Metab. 2018, 44, 452–455. DOI: 10.1016/j.diabet.2017.11.005.
  • Kwon, M. J.; Lee, Y. J.; Jung, H. S.; Shin, H. M.; Kim, T. N.; Lee, S. H.; Rhee, B. D.; Kim, M.; Park, J. H. The Direct Effect of Lobeglitazone, a New Thiazolidinedione, on Pancreatic Beta Cells: A Comparison with Other Thiazolidinediones. Diabetes Res. Clin. Pract. 2019, 151, 209–223. DOI: 10.1016/j.diabres.2019.04.006.
  • Jang, J. Y.; Bae, H.; Lee, Y. J.; Choi, Y.; Kim, H. J.; Park, S. B.; Suh, S. W.; Kim, S. W.; Han, B. W. Structural Basis for the Enhanced anti-Diabetic Efficacy of Lobeglitazone on PPARγ. Sci. Rep. 2018, 8, 11–31. DOI: 10.1038/s41598-017-18274-1.
  • Lee, Y. H.; Kim, J. H.; Kim, S. R.; Jin, H. Y.; Rhee, E. J.; Cho, Y. M.; Lee, B. W. Lobeglitazone, a Novel Thiazolidinedione, Improves Non-Alcoholic Fatty Liver Disease in Type 2 Diabetes: Its Efficacy and Predictive Factors Related to Responsiveness. J. Korean Med. Sci. 2017, 32, 60–69. DOI: 10.3346/jkms.2017.32.1.60.
  • Lee, H. W.; Kim, B. Y.; Ahn, J. B.; Kang, S. K.; Lee, J. H.; Shin, J. S.; Ahn, S. K.; Lee, S. J. S.; Yoon, S. Molecular Design, Synthesis, and Hypoglycemic and Hypolipidemic Activities of Novel Pyrimidine Derivatives Having Thiazolidinedione. Eur. J. Med. Chem. 2005, 40, 862–874. DOI: 10.1016/j.ejmech.2005.03.019.
  • Schimke, K.; Davis, T. M. E. Drug Evaluation: Rivoglitazone, a New Oral Therapy for the Treatment of Type 2 Diabetes. Curr. Opin. Investig. Drugs 2007, 8, 338–344.
  • Kong, A. P. S.; Yamasaki, A.; Ozaki, R.; Saito, H.; Asami, T.; Ohwada, S. G.; Ko, T. C.; Wong, C. K.; Leung, G. T. C.; Lee, K. F.; et al. A Randomized-Controlled Trial to Investigate the Effects of Rivoglitazone, a Novel PPAR Gamma Agonist on Glucose-Lipid Control in Type 2 Diabetes. Diabet. Obesit. Metab. 2011, 13, 806–813. DOI: 10.1111/j.1463-1326.2011.01411.x.
  • Takashi, S.; Katsutoshi, M.; Eiko, I.; Yasuo, S.; Takeshi, F.; Yutaka, K. Chem. Pharm. Bull. 1982, 30, 3580–3600.
  • Kanji, M.; Takeshi, F. European Patent Organization Patent EP0193256A1, 1986.
  • Knoevenagel, E; Faber, W. Berichteder deutschen chemischen Gesellschaft. 1898, 31(3), 2768-2772.
  • March, J. Adv. Organic Chem. React. Mech. Struct. 1968, 693, 697–698.
  • Kraus, G. A.; Krolski, M. E. Synthesis of a Precursor to Quassimarin. J. Org. Chem. 1986, 51, 3347–3350. DOI: 10.1021/jo00367a017.
  • Tietze, L. F. Domino Reactions in Organic Synthesis. Chem. Rev. 1996, 96, 115–136. DOI: 10.1021/cr950027e.
  • Meng, G.; Gao, Y.; Zheng, M.-L. Improved Preparation of 2,4-Thiazolidinedione. Org. Prep. Proced. Int. 2011, 43, 312–313. DOI: 10.1080/00304948.2011.582008.
  • Sawant, R. L.; Gade, S. T. Life Style Disorder Related to Netra. World J. Pharm. Res. 2017, 7, 469–476. DOI: 10.20959/wjpr20177-8725.
  • Lobo, P. L.; Poojary, B.; Manjunatha, K.; Prathibha, A.; Kumari, N. S. Pharm. Chem. 2012, 4, 867–871.
  • Hoon, C.; Ying, W.; Cheol-Hee, C. Patent, US 2011/0269954 Al. 2010.
  • Hoon, C.; Ying, W.; Cheol-Hee, C. European Patent Application, Patent, EP2383263A2. 2011.
  • Sohda, T.; Mizuno, K.; Kawamatsu, Y. Studies on Antidiabetic Agents. VI. Asymmetric Transformation of (+/-)-5-[4-(1-Methylcyclohexylmethoxy)Benzyl]-2,4- Thiazolidinedione(Ciglitazone) with Optically Active 1-Phenylethylamines. Chem. Pharm. Bull. 1984, 32, 4460–4465. DOI: 10.1248/cpb.32.4460.
  • Cossy, J.; Menciu, C.; Rakotoarisoa, H.; Kahn, P. H.; Desmurs, J. R. A Short Synthesis of Troglitazone: An Antidiabetic Drug for Treating Insulin Resistance. Bioorg. Med. Chem. Lett. 1999, 9, 3439–3440. DOI: 10.1016/S0960-894X(99)00630-7.
  • Ortiz, A.; Sansinenea, E. Synthetic Thiazolidinediones: Potential Antidiabetic Compounds. Curr. Organic Chem. 2011, 15, 108–127. DOI: 10.2174/138527211793797774.
  • Yuzuru, S.; Hideya, M.; Makoto, Y. European Patent Application, Patent EP0816340Al. 1998.
  • Mustafa, A.; Didem, G.; Aycu, Y.; Nurten, R. Patent WO 2,00,40,00,810 A l. 2004.
  • Madivada, L. R.; Anumala, R. R.; Gilla, G.; Alla, S.; Charagondla, K.; Kagga, M.; Bhattacharya, A.; Bandichho, R. An Improved Process for Pioglitazone and Its Pharmaceutically Acceptable Salt †. Org. Process Res. Dev. 2009, 13, 1190–1194. DOI: 10.1021/op900131m.
  • Jin Oh, P.; Yong Gil, K.; Han Il, S.; Yun Jeong, L.; Eun, M. K. Patent WO 2009148195 Al. 2009.
  • Shen, Z.; Bakhtiar, R.; Komuro, M.; Awano, K.; Taga, F.; Colletti, A.; Hora, D.; Feeney, W.; Franklin, R. B.; Vincent, S.; Iliff, S. Enantiomer Ratio of MK-0767 in Humans and Nonclinical Species. Rapid Commun. Mass Spectrom. 2005, 19, 1125–1129. DOI: 10.1002/rcm.1897.
  • Clark, D. A.; Goldstein, S. W.; Volkmann, R. A.; Eggler, J. F.; Holland, G. F.; Hulin, B.; Stevenson, R. W.; Kreutter, D. K.; Gibbs, EMl.; Krupp, M. N.; et al. Substituted Dihydrobenzopyran and Dihydrobenzofuran Thiazolidine-2,4-Diones as Hypoglycemic Agents. J. Med. Chem. 1991, 34, 319–325. DOI: 10.1021/jm00105a050.
  • Finch, H.; Fox, C.; Sajad, M.; Van Niel, M. B.; Forrest, A. US 2011/0053986Al. 2011.
  • Patent US009078885B2 2015, 7. www.fda.gov/medwatch/SAFETY/2007/Sep_PI/ActoplusMet_PI.pdf
  • Cantello, B. C. C.; Cawthorne, M. A.; Cottam, G. P.; Duff, P. T.; Haigh, D.; Hindley, R. M.; Lister, C. A.; Smith, S. A.; Thurlby, P. L. [[Omega-(Heterocyclylamino)Alkoxy]Benzyl]-2,4-Thiazolidinediones as Potent Antihyperglycemic Agents. J. Med. Chem. 1994, 37, 3977–3985. DOI: 10.1021/jm00049a017.
  • Mark, H. R. European Patent Application, Patent EP0306228A1. 1989.
  • Cantello, B. C. C.; Cawthorne, M. A.; Haigh, D.; Hindley, R. M.; Smith, S. A.; Thurlby, P. L. The Synthesis of BRL 49653 - a Novel and Potent Antihyperglycaemic Agent. Bioorg. Med. Chem. Lett. 1994, 4, 1181–1184. DOI: 10.1016/S0960-894X(01)80325-5.
  • Johannes, L.; Rashid, K.; Rehman, A.; Aniruddha, P. Patent WO2007/017095Al. 2007.
  • Ujire, S.; Sridharan, M.; Sambasivam, G. Patent WO 03/029251 A l. 2003.
  • Zhou, H.; Zhang, R.; Mu, S.; Zhang, H.; Lu, X.-B. Organocatalytic Cyclization of COS and Propargylic Derivatives to Value‐Added Heterocyclic Compounds. ChemCatChem 2019, 11, 5728–5732. DOI: 10.1002/cctc.201900490.
  • Cantello, B. C. C.; Eggleston, D. S.; Haigh, D.; Haltiwanger, R. C.; Heath, C. M.; Hindley, R. M.; Jennings, K. R.; Sime, J. T.; Woroniecki, S. R. Facile Biocatalytic Reduction of the Carbon–Carbon Double Bond of 5-Benzylidenethiazolidine-2,4-Diones. Synthesis of (±)-5-(4-{2-[Methyl(2-Pyridyl)Amino]Ethoxy}Benzyl)Thiazolidine-2,4-Dione (BRL 49653), Its (R)-(+)-Enantiomer and Analogues. J. Chem. Soc. Perkin Trans. 1994, 1, 3319–3324. DOI: 10.1039/P19940003319.
  • Lee, H. W.; Ahn, J. B.; Kang, S. K.; Ahn, S. K.; Ha, D.-C. Process Development and Scale-Up of PPAR α/γ Dual Agonist Lobeglitazone Sulfate (CKD-501). Org. Proc. Res. Dev. 2007, 11, 190–199. DOI: 10.1021/op060087u.
  • Sharma, V. K.; Barde, A.; Rattan, S. An Efficient and Scalable Approach for the Synthesis of Piperazine Based Glitazone and Its Derivatives. Synth. Commun. 2020, 50, 2181–2187. DOI: 10.1080/00397911.2020.1769133.
  • [Kim, J.; Kim, H.; Park, S. B. Privileged Structures: Efficient Chemical “Navigators” Toward Unexplored Biologically Relevant Chemical Spaces. J. Am. Chem. Soc. 2014, 136, 14629–14638. DOI: 10.1021/ja508343a.
  • Zhang, Y.; Miao, Z.; Wang, S.; Yao, J.; Wu, S.; Zhang, W.; Zhu, S.; Sheng, C.; Dong, G.; Wang, W. Facile Construction of Structurally Diverse Thiazolidinedione-Derived Compounds via Divergent Stereoselective Cascade Organocatalysis and Their Biological Exploratory Studies. ACS Comb. Sci. 2013, 15, 298–308. DOI: 10.1021/co400022r.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.