Teneligliptin

Base Information

• Chemical Name: Teneligliptin
• CAS No.: 760937-92-6
• Molecular Formula: C22H30 N6 O S
• Molecular Weight: 426.586
• Mol file: 760937-92-6.mol

Synonyms:Thiazolidine,3-[[(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)-1-piperazinyl]-2-pyrrolidinyl]carbonyl]-(9CI); 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)

Purity/Quality:

99.0% Min., ^*data from raw suppliers

Teneligliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Teneligliptin was approved in September 2012 in Japan for the treatment of patients with Type 2 diabetes mellitus (T2DM). Teneligliptin is a member of the dipeptidyl peptidase 4 (DPP-4) inhibitor class of antidiabetes agents. DPP-4 is an enzyme that degrades GLP-1, a 30-amino acid peptide that is secreted in response to food intake. GLP-1 stimulates insulin secretion and inhibits glucagon secretion, which leads to lower levels of plasma glucose. Teneligliptin is one of a growing numbers of DPP-4 inhibitors to be approved worldwide. The discovery of teneligliptin was guided by structure-based design, with a key element being binding of the phenyl group in the S2 pocket, which not only increases potency for DPP-4, but also improves selectivity versus DPP-8 and DPP- 9. Teneligliptin is a potent inhibitor of DPP-4 in the enzyme inhibition assay (IC50=0.37 nM).
• Uses: Teneligliptin, is a dipeptidyl peptidase-4 (DPP-4) inhibitor that is used to treat type 2 diabetes. It is eliminated via excretion, and has a half-life of 24.2 hours in the human body.

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

• 1、 -. "Method for preparing hydrobromic acid teneligliptin". Paragraph 0043; 0044; 0059. . Retrieved 2017/07/01.
• 2、 Yoshida, Tomohiro,Akahoshi, Fumihiko,Sakashita, Hiroshi,Kitajima, Hiroshi,Nakamura, Mitsuharu,Sonda, Shuji,Takeuchi, Masahiro,Tanaka, Yoshihito,Ueda, Naoko,Sekiguchi, Sumie,Ishige, Takayuki,Shima, Kyoko,Nabeno, Mika,Abe, Yuji,Anabuki, Jun,Soejima, Aki,Yoshida, Kumiko,Takashina, Yoko,Ishii, Shinichi,Kiuchi, Satoko,Fukuda, Sayaka,Tsutsumiuchi, Reiko,Kosaka, Keigo,Murozono, Takahiro,Nakamaru, Yoshinobu,Utsumi, Hiroyuki,Masutomi, Naoya,Kishida, Hiroyuki,Miyaguchi, Ikuko,Hayashi, Yoshiharu. "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". . p. 5705 - 5719. Retrieved 2012/10/30.