Supporting Information
Supporting Information File 1: 1H and 13C NMR spectra of compound 6 in CDCl3. | ||
Format: DOC | Size: 87.0 KB | Download |
Cite the Following Article
Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors
Santosh K. Singh, Narendra Manne and Manojit Pal
Beilstein J. Org. Chem. 2008, 4, No. 20.
https://doi.org/10.3762/bjoc.4.20
How to Cite
Singh, S. K.; Manne, N.; Pal, M. Beilstein J. Org. Chem. 2008, 4, No. 20. doi:10.3762/bjoc.4.20
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Smolobochkin, A.; Gazizov, A.; Appazov, N.; Sinyashin, O.; Burilov, A. Progress in the Stereoselective Synthesis Methods of Pyrrolidine-Containing Drugs and Their Precursors. International journal of molecular sciences 2024, 25, 11158. doi:10.3390/ijms252011158
- Mathur, V.; Alam, O.; Siddiqui, N.; Jha, M.; Manaithiya, A.; Bawa, S.; Sharma, N.; Alshehri, S.; Alam, P.; Shakeel, F. Insight into Structure Activity Relationship of DPP-4 Inhibitors for Development of Antidiabetic Agents. Molecules (Basel, Switzerland) 2023, 28, 5860. doi:10.3390/molecules28155860
- Lioe, T. S.; Xie, Z.; Wu, J.; Li, W.; Sun, L.; Feng, Q.; Sekar, R.; Tefsen, B.; Ruiz-Carrillo, D. The Mycobacterium tuberculosis prolyl dipeptidyl peptidase cleaves the N-terminal peptide of the immunoprotein CXCL-10. Biological chemistry 2023, 404, 633–643. doi:10.1515/hsz-2022-0265
- Maslov, I. O.; Zinevich, T. V.; Kirichenko, O. G.; Trukhan, M. V.; Shorshnev, S. V.; Tuaeva, N. O.; Gureev, M. A.; Dahlén, A. D.; Porozov, Y. B.; Schiöth, H. B.; Trukhan, V. M. Design, Synthesis and Biological Evaluation of Neogliptin, a Novel 2-Azabicyclo[2.2.1]heptane-Based Inhibitor of Dipeptidyl Peptidase-4 (DPP-4). Pharmaceuticals (Basel, Switzerland) 2022, 15, 273. doi:10.3390/ph15030273
- Taşdemir, V. Synthesis of imidazo-1,4-oxazinone derivatives and investigation of reaction mechanism. Turkish journal of chemistry 2021, 45, 1639–1649. doi:10.3906/kim-2106-28
- Reddy, B. K. K.; Sekhar, K. B. C.; Mohan, C. K. Bioanalytical Method Development and Validation for the Simultaneous Determination of Vildagliptin and Telmisartan in Rabbit Plasma Using RP-HPLC. Journal of Pharmaceutical Research International 2021, 76–86. doi:10.9734/jpri/2021/v33i131141
- Pal, S.; Pal, M. Anti-diabetes Research in India: Contributions from Industrial Organizations. Drug Discovery and Drug Development; Springer Singapore, 2021; pp 179–212. doi:10.1007/978-981-15-8002-4_8
- Arar, S.; Al-Qudah, E.; Al-Zweiri, M.; Sweidan, K. New forced degradation products of vildagliptin: Identification and structural elucidation using LC-MS, with proposed formation mechanisms. Journal of Liquid Chromatography & Related Technologies 2020, 1–12.
- Arar, S.; Al-Qudah, E.; Alzweiri, M.; Sweidan, K. New forced degradation products of vildagliptin: Identification and structural elucidation using LC-MS, with proposed formation mechanisms. Journal of Liquid Chromatography & Related Technologies 2020, 43, 633–644. doi:10.1080/10826076.2020.1779084
- Wakaki, T.; Sakai, K.; Enomoto, T.; Kondo, M.; Masaoka, S.; Oisaki, K.; Kanai, M. C(sp3 )-H Cyanation Promoted by Visible-Light Photoredox/Phosphate Hybrid Catalysis. Chemistry (Weinheim an der Bergstrasse, Germany) 2018, 24, 8051–8055. doi:10.1002/chem.201801746
- Biftu, T.; SinhaRoy, R. DPP-4 Inhibitors. Comprehensive Medicinal Chemistry III; Elsevier, 2017; Vol. 7, pp 512–555. doi:10.1016/b978-0-12-409547-2.12443-6
- Stockdale, T. P.; Williams, C. M. Pharmaceuticals that contain polycyclic hydrocarbon scaffolds. Chemical Society reviews 2015, 44, 7737–7763. doi:10.1039/c4cs00477a
- Jansen, K.; Heirbaut, L.; Verkerk, R.; Cheng, J. D.; Joossens, J.; Cos, P.; Maes, L.; Lambeir, A.-M.; De Meester, I.; Augustyns, K.; Van der Veken, P. Extended Structure–Activity Relationship and Pharmacokinetic Investigation of (4-Quinolinoyl)glycyl-2-cyanopyrrolidine Inhibitors of Fibroblast Activation Protein (FAP). Journal of medicinal chemistry 2014, 57, 3053–3074. doi:10.1021/jm500031w
- Mohammad, M. A.-A.; Elkady, E. F.; Fouad, M. A. Development and validation of a reversed-phase column liquid chromatographic method for simultaneous determination of two novel gliptins in their binary mixtures with Metformin. European Journal of Chemistry 2012, 3, 152–155. doi:10.5155/eurjchem.3.2.152-155.570
- El-Bagary, R. I.; Elkady, E. F.; Ayoub, B. M. Liquid Chromatographic Methods for the Determination of Vildagliptin in the Presence of its Synthetic Intermediate and the Simultaneous Determination of Pioglitazone Hydrochloride and Metformin Hydrochloride. International journal of biomedical science : IJBS 2011, 7, 201–208.
- Jain, S. K.; Vishwakarma, S.; Nayak, P.
- Tahrani, A. A.; Piya, M. K.; Barnett, A. H. Drug evaluation: vildagliptin-metformin single-tablet combination. Advances in therapy 2009, 26, 138–154. doi:10.1007/s12325-009-0010-0
Patents
- HU DEXING; WANG LIHONG; WANG YANJUAN; WU JIAO; CAI YIFAN; ZHU QINGGUO; QIN XINRONG; YAO LIGAO; QIU JIAJUN. Detection method of (S)-pyrrolidine-2-formonitrile hydrochloride. CN 114646700 A, June 21, 2022.
- LU WEISHEN; ZHOU ZHENYU; ZU JINXIANG; ZHANG XIN. Preparation method of vildagliptin cyclic amidine impurity. CN 108329322 A, July 27, 2018.
- KOVI RAVISHANKER; RAPOLE KESHAVRAO; NAIK ASHISH; KANNAPAN JAYARAMAN; MADALA MURALIKRISHNA; THAKOR SANJAY. Process for preparing saxagliptin and its novel intermediates useful in the synthesis thereof. US 9150511 B2, Oct 6, 2015.
- MATHAD VIJAYAVITTHAL THIPPANNACHAR VIJAYAVITTHAL; PATIL NILESH SUDHIR NILESH; SOLANKI PAVANKUMAR VRAJLAL PAVANKUMAR; IPPAR SHARAD SUBHASH SHARAD; BODAKE MAHENDRA BHAGIRATH MAHENDRA; TALLA RAJESH RAJESH; MALI ANIL CHATURLAL ANIL. A PROCESS FOR THE PREPARATION OF VILDAGLIPTIN AND ITS INTERMEDIATE THEREOF. WO 2013179300 A3, Aug 28, 2014.
- ZHI YONGGANG; ZHAO YUYAN; ZHANG ZHEN; WU DEZHI; LI TAOTAO. Method for preparing midbody (2S)-N-chloracetyl-2-cyano tetrahydropyrrole of vildagliptin. CN 103848770 A, June 11, 2014.
- KOVI RAVISHANKER; RAPOLE KESHAVRAO; NAIK ASHISH; KANNAPAN JAYARAMAN; MADALA MURALI KRISHNA; THAKOR SANJAY F. Process for preparing saxagliptin and its novel intermediates useful in the synthesis thereof. US 8748631 B2, June 10, 2014.
- KOVI RAVISHANKER; RAPOLE KESHAVRAO; NAIK ASHISH; KANNAPAN JAYARAMAN; MADALA MURALIKRISHNA; THAKOR SANJAY F. PROCESS FOR PREPARING SAXAGLIPTIN AND ITS NOVEL INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF. WO 2012162507 A1, Nov 29, 2012.
- BARATELLA MARCO. PROCESS AND INTERMEDIATES FOR PREPARATION OF AN ACTIVE INGREDIENT. WO 2012004210 A1, Jan 12, 2012.
- BARATELLA MARCO. PROCESSO ED INTERMEDI PER LA PREPARAZIONE DI UN PRINCIPIO ATTIVO. IT MI20101239 A1, Jan 7, 2012.