| Identification | Back Directory | [Name]
Teneligliptin | [CAS]
760937-92-6 | [Synonyms]
Teliglietin
teneligliptin
Teneligptin WS
Teneligliptin (MP-513)
API (Teneligliptin free base)
3-[[(2S,4R)-4-[4-(3-Methyl-1-phenyl-1H-pyrazol-5-yl)-1-piperazinyl]-2-pyrrolidinyl]carbonyl]thiazolidine
3-[[(2S,4S)-4-[4-(3-Methyl-1-phenyl-1H-pyrazol-5-yl)-1-piperazinyl]-2-pyrrolidinyl]carbonyl]thiazolidine
Methanone,[(2S,4S)-4-[4-(3-Methyl-1-phenyl-1H-pyrazol-5-yl)-1-piperazinyl]-2-pyrrolidinyl]-3-thiazolidinyl-
[(2S,4S)-4-[4-(5-methyl-2-phenylpyrazol-3-yl)piperazin-1-yl]pyrrolidin-2-yl]-(1,3-thiazolidin-3-yl)methanone | [Molecular Formula]
C22H30N6OS | [MDL Number]
MFCD13195565 | [MOL File]
760937-92-6.mol | [Molecular Weight]
426.58 |
| Questions And Answer | Back Directory | [Preparation]
Teneligliptin was synthesized from N-Boc piperazine and diketene via condensation, cyclization, and deprotection to obtain intermediate 1-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazine; then, using trans-4-hydroxy-L-proline as a starting material, it underwent Fmoc protection, oxidation, and condensation to obtain intermediate 3-[(2S)-1-(9H-fluorene-9-ylmethoxycarbonyl)-4-oxopyrrolidine-2-ylcarbonyl]thiazolidin; finally, these two intermediates were reductively aminationed and deprotected to obtain the antidiabetic drug Teneligliptin, with an overall yield of 47.2% (based on trans-4-hydroxy-L-proline) and a purity of 99.1% (HPLC). The structure of Teneligliptin was confirmed by MS, IR, 1H-NMR, and 13C-NMR spectra. This synthetic route utilizes inexpensive and readily available raw materials, mild reaction conditions, simple post-processing, and high yield, laying the foundation for pilot-scale production. |
| Chemical Properties | Back Directory | [Melting point ]
>100°C (dec.) | [Boiling point ]
663.4±55.0 °C(Predicted) | [density ]
1.38 | [storage temp. ]
Refrigerator | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
8.70±0.10(Predicted) | [color ]
Off-White | [InChIKey]
WGRQANOPCQRCME-PMACEKPBSA-N | [SMILES]
C([C@@H]1C[C@H](N2CCN(C3N(C4=CC=CC=C4)N=C(C)C=3)CC2)CN1)(N1CCSC1)=O |
| Hazard Information | Back Directory | [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). | [Originator]
Mitsubishi Tanabe Pharma (Japan) | [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. | [Definition]
ChEBI: Teneligliptin is an amino acid amide. | [Brand name]
Tenelia | [storage]
Store at -20°C |
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
T&W GROUP
|
| Telephone: |
021-61551611 13296011611 |
| Website: |
www.trustwe.com/ |
| Company Name: |
LETOPHARM LIMITED
|
| Telephone: |
+86-21-5821 5861 |
| Website: |
www.letopharm.com |
|