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

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

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).

SOLID FORMS OF ERTUGLIFLOZIN FREE BASE AND SOLID DISPERSIONS COMPRISING ERTUGLIFLOZIN L-PYROGLUTAMIC ACID.

The present invention related to novel crystalline forms of (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 free base of formula (I) and process for their preparation thereof. The present invention also relates to amorphous, solid dispersions of (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 L-pyroglutamic acid of formula (II) and process their preparation thereof.

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.).

ERTUGLIFLOZIN CO-CRYSTALS AND PROCESS FOR THEIR PREPARATION

The present invention relates to processes for the preparation of an ertugliflozin-L- pyroglutamic acid (1:1) and co-crystal ertugliflozin-L-proline (1:1) co-crystal. The present invention further relates to an ertugliflozin-L-proline (1:2) co-crystal, processes for its preparation, and its use for the treatment of type 2 diabetes mellitus.

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.

METHODS FOR PREPARING SGLT2 INHIBITORS

This invention relates to methods for preparing a sodium-glucose transporter 2 (SGLT2) inhibitor, a cocrytalline SGLT2 and (S)-5-oxopyrrolidine-2-carboxylic acid (L-PGA) complex, and intermediates useful in the preparation of the said SGLT2 inhibitor.