1564265-93-5

Basic information

• Product Name: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-
• Synonyms: (S,S,S,R)-Saxagliptin;(2'R,2S,cis)-Saxagliptin;Saxagliptin (S,S,S,R)-Isomer;Saxagliptin Impurity 1(S,S,S,R-Isomer);(1S,3S,5S)-2-[(2R)-2-amino-2-(3-hydroxy-1-adamantyl)acetyl]-2-azabicyclo[3.1.0]hexane-3-carbonitrile;(1S,3S,5S)-2-((R)-2-amino-2-((1r,3S,5R,7S)-3-hydroxyadamantan-1-yl)acetyl)-2-azabicyclo[3.1.0]hexane-3-carbonitrile;2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-
• CAS NO: 1564265-93-5
• Molecular Formula: C18H25N3O2
• Molecular Weight: 315.41
• Mol File: 1564265-93-5.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 548.7±35.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• PKA: 15.12±0.40(Predicted)
• CAS DataBase Reference: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-(1564265-93-5)
• EPA Substance Registry System: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2R)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1S,3S,5S)-(1564265-93-5)

Safety Data

• Hazardous Substances Data: 1564265-93-5(Hazardous Substances Data)

Usage

Description

Saxagliptin is a potent and selective reversible inhibitor of dipeptidyl peptidase-4 (DPP-IV), which is an enzyme that plays a crucial role in the regulation of blood glucose levels. It is primarily used in the treatment of type 2 diabetes, helping to improve glycemic control and reduce the risk of complications associated with the disease.

Uses

Used in Pharmaceutical Industry:
Saxagliptin is used as an active pharmaceutical ingredient for the treatment of type 2 diabetes. It works by inhibiting the DPP-IV enzyme, which in turn slows down the degradation of insulin and glucagon-like peptide-1 (GLP-1). This leads to an increased insulin production and a decreased glucagon release, resulting in better blood glucose control.
Additionally, saxagliptin may be used as an impurity in the development and manufacturing process of Saxagliptin (S143500), a medication specifically designed to manage type 2 diabetes. The presence of (2'R,2S,cis)-Saxagliptin as an impurity is important to monitor and control, as it can impact the safety, efficacy, and quality of the final drug product.

Upstream product

• 68766-96-1 ethyl (R)-2-pyrrolidone-5-carboxylate 
• 144978-12-1 1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 361442-00-4 (αS)-α-[[(1,1-dimethylethoxy)carbonyl]-amino]-3-hydroxytricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 361441-97-6 (alpha S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]tricyclo[3.3.1.1^3,7]decane-1-acetic acid 
• 871727-40-1 2-tert-butyl 3-ethyl (1S,3R,5S)-2-azabicyclo[3.1.0]hexane-2,3-dicarboxylate 
• 1091626-35-5 1-tert-butyl 2-ethyl (2R)-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate 
• 932040-48-7 1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate 
• 102502-64-7 (S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride 
• 1564267-10-2 (S)-N-Boc-3-hydroxyadamantylglycine-D-trans-4,5-methanoprolinenitrile 
• 1564267-00-0 (R)-N-Boc-3-hydroxyadamantylglycine-L-trans-4,5-methanoprolinamide 
• 214193-10-9 2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester 
• 178172-26-4 (5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 

Downstream Products

• 841302-24-7 5-hydroxy-saxagliptin 

Relevant articles and documents

Preparation of saxagliptin, a novel DPP-IV inhibitor

The commercial-scale synthesis of the DPP-IV inhibitor, saxagliptin (1), is described from the two unnatural amino acid derivatives 2 and 3. After the deprotection of 3, the core of 1 is formed by the amide coupling of amino acid 2 and methanoprolinamide

Method for preparing saxagliptin

The invention discloses a method for preparing saxagliptin, and belongs to the technical field of drug synthesis. The method comprises the following steps: (a) converting amide on a compound shown ina formula I into cyano and removing Boc groups to obtain a compound shown in a formula II; (b) condensing the compound shown in the formula II and a compound shown in a formula III to obtain a compound shown in a formula IV; and (c) removing Boc groups on the compound shown in the formula IV to obtain a compound shown in a formula V. According to the method, different raw materials and reaction reagents are selected, and a process route is changed, so that four procedures of salifying, condensing, cyanating and de-protecting are shortened into three procedures of cyanating, condensing and de-protecting; meanwhile, cyanating and condensation reaction are realized at the room temperature, the requirements on reaction conditions are reduced, and industrial production can be realized.

Preparation method of medication saxagliptin for treating diabetes

The invention provides a preparation method of saxagliptin with a shorter synthetic route. (S)-3-amino-3-cyano-propionic ether protected by diethyl acetylenedicarboxylate and an amino group is used asa starting material in the presence of an organic phosphine ligand and a palladium catalyst, and is subjected to cyclization, decarboxylation and cyclopropanation to obtain an intermediate product (1S, 3S, 5S)-2-azabicyclo[3.1.0]hexane-3-carbonitrile p-toluenesulfonate, and then the intermediate product is reacted with carboxyl-activated (S)-N-t-butyloxycarboryl-(3-hydroxyadamantane-1-yl)glycineto increase the reaction rate and obtain a saxagliptin product with a high yield and high purity, the reaction route is greatly shortened, the yield in each step is high, the reaction time is short, the production cost is reduced, and industrial production is facilitated.