Teneligliptin

Base Information

• Chemical Name: Teneligliptin
• CAS No.: 760937-92-6
• Molecular Formula: C22H30 N6 O S
• Molecular Weight: 426.586
• UNII: 28ZHI4CF9C
• ChEMBL ID: CHEMBL2147777
• DSSTox Substance ID: DTXSID30997419
• Metabolomics Workbench ID: 153024
• NCI Thesaurus Code: C87623
• Nikkaji Number: J2.689.304F
• Pharos Ligand ID: RPKLVWPN4ZB3
• Wikidata: Q15269678
• Wikipedia: Teneligliptin
• Mol file: 760937-92-6.mol

Synonyms:3-(4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-ylcarbonyl)thiazolidine;teneligliptin

Chemical Property of Teneligliptin

Chemical Property:

• Boiling Point: 663.4±55.0 °C(Predicted)
• PKA: 8.70±0.10(Predicted)
• PSA: 81.94000
• Density: 1.38
• LogP: 1.83570
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 426.22018078
• Heavy Atom Count: 30
• Complexity: 594

Purity/Quality:

≥99% ^*data from raw suppliers

Teneligliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN(C(=C1)N2CCN(CC2)C3CC(NC3)C(=O)N4CCSC4)C5=CC=CC=C5
• Isomeric SMILES: CC1=NN(C(=C1)N2CCN(CC2)[C@H]3C[C@H](NC3)C(=O)N4CCSC4)C5=CC=CC=C5
• Recent ClinicalTrials: Clinical Efficacy and Safety Evaluation of Teneligliptin in Type 2 Diabetes Who Have Inadequate GlycemIc Control With Empaglyflozin 25 mg and Metformin
• Recent EU Clinical Trials: A Phase IIb, double-blind, parallel group, multi-centre, dose-finding study to investigate the efficacy and safety of 4 doses of MP-513 when added to ongoing metformin monotherapy in subjects with Type 2 diabetes mellitus, with an open label extension
• Recent NIPH Clinical Trials: Efficacy and safety of degludec/liraglutide combination injection switching from basal insulin therapy with the DPP-4 inhibitor in Japanese type 2 diabetic patients
• General Description: Teneligliptin is a highly potent, selective, and long-acting dipeptidyl peptidase IV (DPP-4) inhibitor developed for the treatment of type 2 diabetes. It exhibits strong oral activity and enhances plasma concentrations of active glucagon-like peptide-1 (GLP-1), promoting insulin secretion and glucose control without inducing hypoglycemia. Its optimized structure, featuring a thiazolidine moiety and interactions with the S2 subsite of DPP-4, ensures both efficacy and selectivity, making it suitable for once-daily dosing. Teneligliptin has been approved for clinical use, particularly in Japan, as a therapeutic option for managing type 2 diabetes.

Technology Process of Teneligliptin

There total 26 articles about Teneligliptin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

tert-butyl (2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate (401566-80-1) → 3-{(2S,4S)-1-(1,1-dimethylethyloxycarbonyl)-4-[4-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazin-1-yl]pyrrolidine-2-ylcarbonyl}thiazolidine (760937-92-6,1404559-17-6)

Guidance literature:

tert-butyl (2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 19h;

With sodium hydrogencarbonate; In water;

Reference yield:

C37H40N6O3S → 3-{(2S,4S)-1-(1,1-dimethylethyloxycarbonyl)-4-[4-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazin-1-yl]pyrrolidine-2-ylcarbonyl}thiazolidine (760937-92-6,1404559-17-6)

Guidance literature:

With piperidine; In dichloromethane; at 25 - 30 ℃;

Reference yield:

1-1(2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidin-1-yl ethanone → 3-{(2S,4S)-1-(1,1-dimethylethyloxycarbonyl)-4-[4-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazin-1-yl]pyrrolidine-2-ylcarbonyl}thiazolidine (760937-92-6,1404559-17-6)

Guidance literature:

With hydrogen bromide; In water; isopropyl alcohol; at 80 - 85 ℃; for 16h; Time;

upstream raw materials:

tert-butyl (2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate

tert-butyl 4-(3-oxobutanoyl)piperazine-1-carboxylate

1-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazine

1-Phenyl-3-methyl-5-aminopyrazole

Refernces

Discovery and preclinical profile of teneligliptin (3-[(2S,4S)-4-[4-(3- methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl] thiazolidine): A highly potent, selective, long-lasting and orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes

10.1016/j.bmc.2012.08.012

The study focuses on the discovery and preclinical profile of teneligliptin, a potent, selective, long-lasting, and orally active dipeptidyl peptidase IV (DPP-4) inhibitor, developed for the treatment of type 2 diabetes. The research explores the structure-activity relationship of L-prolylthiazolidines and identifies teneligliptin (compound 8g) as a highly effective DPP-4 inhibitor. The study involves the synthesis and evaluation of various chemical derivatives, including bicyclic heteroarylpiperazines and prolylthiazolidine analogs, to optimize their interaction with the S2 subsite of DPP-4, thereby enhancing both potency and selectivity. The chemicals used serve as DPP-4 inhibitors, aiming to increase the plasma concentration of active glucagon-like peptide-1 (GLP-1), which stimulates insulin secretion and helps in glucose control, thereby offering a potential once-daily treatment option for type 2 diabetes without causing hypoglycemia. The study includes in vitro and in vivo evaluations, pharmacokinetic profiling, and X-ray crystal structure determination to understand the molecular interactions of teneligliptin with DPP-4, ultimately leading to its approval for use in Japan.