1210344-83-4

Basic information

• Product Name: Ertugliflozin
• Synonyms: Pidolate;ERTUGLIFLOZIN PIDOLATE;Gliadine L- pyroglutamate;PF-04971729 L-pyroglutamic acid;Ertugliflozin L-pyroglutamic Acid (1:1);PF-04971729 ((S)-5-oxopyrrolidine-2-carboxylic acid);(S)-5-Oxopyrrolidine-2-carboxylic acid compound with (1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1);(1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1) compound with (S)-5-oxopyrrolidine-2-carboxylic acid
• CAS NO: 1210344-83-4
• Molecular Formula: C₅H₇NO₃*C₂₂H₂₅ClO₇
• Molecular Weight: 565.99668
• Mol File: 1210344-83-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Ertugliflozin(CAS DataBase Reference)
• NIST Chemistry Reference: Ertugliflozin(1210344-83-4)
• EPA Substance Registry System: Ertugliflozin(1210344-83-4)

Safety Data

• Hazardous Substances Data: 1210344-83-4(Hazardous Substances Data)

Usage

Description

Ertugliflozin is a sodium/glucose cotransporter 2 (SGLT2) inhibitor, which is a pharmaceutical compound used for the treatment of type 2 diabetes. It functions by inhibiting the reabsorption of glucose in the kidneys, leading to increased glucose excretion and reduced blood glucose levels.

Uses

Used in Pharmaceutical Industry:
Ertugliflozin is used as a therapeutic agent for the treatment of type 2 diabetes. It helps manage blood sugar levels by inhibiting the reabsorption of glucose in the kidneys, thereby promoting its excretion and reducing hyperglycemia. This action contributes to better glycemic control and overall diabetes management.

Upstream product

• 1629222-50-9 (2S,3S,4R)-2,3,4-tris(benzyloxy)-1-((benzyloxy)-methyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane 
• 1210344-57-2 Ertugliflozin 
• 98-79-3 L-Pyroglutamic acid 
• 1298086-18-6 (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate 
• 1431329-06-4 (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one oxalate 
• 1431329-05-3 (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one 
• 1528636-33-0 (2S,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-carbaldehyde 
• 1528636-39-6 (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 714269-57-5 (2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol 
• 461432-23-5 4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene 
• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 
• 1528636-29-4 ((2R,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-yl)methanol 

Relevant articles and documents

AN EFFICIENT PROCESS FOR THE PREPARATION OF ERTUGLIFLOZIN L-PYROGLUTAMIC ACID AND INTERMEDIATES THEREOF

The present invention relates to an efficient process for the preparation of Ertugliflozin L-pyroglutamic acid of formula (I) and intermediate thereof, in environment friendly conditions. The present invention further relates to a process for the preparation of substantially pure intermediate of formula (IV).

Preparation method of ertugliflozin and intermediate of ertugliflozin

The invention provides a synthesis method of ertugliflozin. The route relates to a new intermediate compound 3 and a compound 5, an SGLT-2 inhibitor ertugliflozin is prepared by virtue of the new intermediate compound 3 and the compound 5, and the preparation method is simple in process route, low in cost and applicable to industrial production. (The compound 3 and the compound 5 are described in the specification.).

Commercial route research and development for SGLT2 inhibitor candidate ertugliflozin

A practical synthesis of SGLT2 inhibitor candidate ertugliflozin (1) has been developed for potential commercial application. The highly telescoped process involves only three intermediate isolations over a 12-step sequence. The dioxabicyclo[ 3.2.1]octane motif is prepared from commercially available 2,3,4,6-tetra-O-benzyl-D-glucose, with nucleophilic hydroxymethylation of a 5-ketogluconamide intermediate as a key step. The aglycone moiety is introduced via aryl anion addition to a methylpiperazine amide. High chemical purity of the API is assured through isolation of the crystalline penultimate intermediate, tetraacetate 39. A cocrystalline complex of the amorphous solid 1 with L-pyroglutamic acid has been prepared in order to improve the physical properties for manufacture and to ensure robust API quality.