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| Anagliptin Basic information |
| Product Name: | Anagliptin | | Synonyms: | Anagliptin;N-[2-[[2-[(2S)-2-cyano-1-pyrrolidinyl]-2-oxoethyl]aMino]-2-Methylpropyl]-2-Methyl-6-pyrazolo[1,5-a]pyriMidinecarboxaMide;Anagliptin API;Suiny;(S)-N-(2-(2-(2-cyanopyrrolidin-1-yl)-2-oxoethylaMino)-2-Methylpropyl)-2-Methylpyrazolo[1,5-a]pyriMidine-6-carboxaMide;N-[2-[[2-[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl]amino]-2-methylpropyl]-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide;(R)-N-(2-(2-(2-cyanopyrrolidin-1-yl)-2-oxoethylamino)-2-methylpropyl)-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide;N-[2-[[2-[(2S)-2-Cyano-1-pyrrolidinyl]-2-oxoethyl]amino]-2-methylpropyl]-2-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide | | CAS: | 739366-20-2 | | MF: | C19H25N7O2 | | MW: | 383.45 | | EINECS: | | Product Categories: | | Mol File: | 739366-20-2.mol |
| Anagliptin Chemical Properties |
| Melting point | 115 - 119°C | | density | 1.33±0.1 g/cm3(Predicted) | | storage temp. | Refrigerator | | solubility | Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly) | | form | Solid | | pka | 12.40±0.46(Predicted) | | color | White to Off-White |
| Anagliptin Usage And Synthesis |
| 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. | | Originator | Sanwa Kagaku Kenkyusho (Japan) | | 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. | | Brand name | Suiny | | 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. | | Synthesis | The most likely process-scale synthesis has been published and is depicted in Scheme 3.24
Commercially available (S)-1-(2-chloroacetyl)-pyrrolidine-2-carbonitrile (12) was alkylated with t-butyl
(2-amino-2-methyl-1-propyl)carbamate (13), giving rise to (S)-t-butyl (2-((2-(2-cyanopyrrolidin-1-yl)-2-
oxoethyl)amino)-2-methylpropyl)carbamate (14). This Boc-protected system was subsequently treated
with strong acid to give the ethylene diamine derivative 15 in 96% yield. Activation of 15 with CDI
followed by coupling with commercially available 2-methylpyrazolo[1,5-a] pyrimidine-6-carboxylic
acid (16) gave anagliptin (III) in 90% yield. |
| Anagliptin Preparation Products And Raw materials |
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