Anagliptin

Base Information

• Chemical Name: Anagliptin
• CAS No.: 739366-20-2
• Molecular Formula: C₁₉H₂₅N₇O₂
• Molecular Weight: 383.453
• Mol file: 739366-20-2.mol

Synonyms:N-[2-[[2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxo-ethyl]amino]-2-methyl-propyl]-2-methyl-pyrazolo[1,5-a]pyrimidine-6-carboxamide;Anagliptin;

Chemical Property of Anagliptin

Chemical Property:

• Appearance/Colour: Off-White Solid
• Melting Point: 115-119°C
• PKA: 12.40±0.46(Predicted)
• PSA: 118.91000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 1.55388
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Anagliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Anagliptin is a dipeptidyl peptidase-4 (DPP-4) inhibitor that was approved in Japan in November 2012 for the treatment of patients with Type 2 diabetes mellitus (T2DM). Anagliptin (also known asSK-0403) is a treatment for diabetes based on inhibition of DPP-4, an enzyme that is responsible for degradation of glucagon-like peptide 1 (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. Following the introduction of the first DPP-4 inhibitor, sitagliptin, in 2006, several members of the gliptin class have been approved worldwide. Anagliptin was discovered from an effort to replace a metabolically labile isoindoline group from an earlier DPP-4 inhibitor series with a stable bioisostere. Anagliptin is a potent DPP-4 inhibitor, with an IC50=3.8 nM and >10,000-fold selectivity over inhibition of DPP-8 and DPP-9.
• Uses: Anagliptin is a dipeptidyl peptidase-4 (DPP-4) inhibitor that suppresses proliferation of vascular smooth muscles and monocyte inflammatory reaction. It also attenuates atherosclerosis in male apolipoprotein E-deficient mice.
• Clinical Use: Anagliptin, which is marketed as Beskoa or Suiny, is a dipeptidyl peptidase–IV (DPP-4) inhibitor which was approved in September 2012 and launched in November 2012 in Japan for the treatment of Type II diabetes. The drug was co-developed by three Japanese companies; Kowa, Sanwa Kagaku and JW pharmaceutical. Anagliptin, which is more selective against several recombinant human proteases by comparison to sitagliptin and vildagliptin, has more than 10,000-fold selectivity over the structurally homologous DPP-8 and DPP-9 enzymes.

Technology Process of Anagliptin

There total 20 articles about Anagliptin 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: 98.0%

(S)-1-(2-((1-amino-2-methylpropan-2-yl)amino)acetyl)pyrrolidine-2-carbonitrile (794460-89-2) + C12H10N4O4 → (S)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid {2-[(2-cyanopyrrolidin-1-yl)-2-oxoethylamino]-2-methylpropyl}amide (739366-20-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 5h;

Reference yield: 88.0%

2-methylpyrazolo[1,5-a] pyrimidine-6-carboxylic acid (739364-95-5) + (S)-1-[(2-amino-1,1-dimethylethyl)aminoacetyl]pyrrolidine-2-carbonitrile dihydrochloride → (S)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid {2-[(2-cyanopyrrolidin-1-yl)-2-oxoethylamino]-2-methylpropyl}amide (739366-20-2)

Guidance literature:

2-methylpyrazolo[1,5-a] pyrimidine-6-carboxylic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In acetonitrile; for 0.5h;

(S)-1-[(2-amino-1,1-dimethylethyl)aminoacetyl]pyrrolidine-2-carbonitrile dihydrochloride; In acetonitrile; at 20 ℃; for 3h;

Reference yield: 88.0%

(S)-1-(2-((1-amino-2-methylpropan-2-yl)amino)acetyl)pyrrolidine-2-carbonitrile (794460-89-2) + C13H12N6O4 → (S)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid {2-[(2-cyanopyrrolidin-1-yl)-2-oxoethylamino]-2-methylpropyl}amide (739366-20-2)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 5h;

upstream raw materials:

2-methylpyrazolo[1,5-a] pyrimidine-6-carboxylic acid

tert-butyl N-[2-({2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}amino)-2-methylpropyl]carbamate

(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

(S)-1-(2-((1-amino-2-methylpropan-2-yl)amino)acetyl)pyrrolidine-2-carbonitrile