329045-45-6

Usage

Uses

Used in Pharmaceutical Industry:
ReMogliflozin A is used as an SGLT2 inhibitor for the treatment of type 2 diabetes. It helps in improving glycemic control and reducing the risk of cardiovascular events in patients with diabetes.
Used in Metabolic Disorders Treatment:
ReMogliflozin A is being investigated as a potential treatment for other metabolic disorders due to its effects on glucose regulation and its potential benefits in improving overall metabolic health.
Used in Heart Failure Treatment:
ReMogliflozin A is also being explored for its potential benefits in the treatment of heart failure, as it may help in managing fluid retention and improving cardiovascular function.

Upstream product

• 1338796-70-5 5-methyl-1-(propan-2-yl)-4- [4-(propan-2-yloxy)benzyl]-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 81058-27-7 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide 
• 910054-55-6 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole 
• 329044-14-6 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one 
• 40141-12-6 1-(Chloromethyl)-4-(1-methylethoxy)benzene 
• 1401335-14-5 methyl 2-[(4-isopropoxyphenyl)methyl]-3-oxobutanoate 
• 1028026-83-6 5-methyl-1-(propan-2-yl)-4-[4-(propan-2-yloxy)benzyl]-1,2-dihydro-3H-pyrazol-3-one 
• 1171016-90-2 5-methyl-4-{[4-(propan-2-yloxy)phenyl]methyl}-1H-pyrazol-3-yl methanesulfonate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 82657-71-4 (4-isopropoxyphenyl)methanol 

Downstream Products

• 1253394-47-6 C₂₈H₄₂N₂O₉ 
• 1253394-48-7 5-methyl-1-(1-methylethyl)-4-({4-[(1-methylethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl 6-O-(phenylcarbonyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

AN IMPROVED PROCESS FOR THE PREPARATION REMOGLIFLOZIN ETABONATE OR PHARMACEUTICALLY ACCEPTABLE SALT, SOLVATE, HYDRATE THEREOF

The present invention relates to an improved process for the preparation of Remogliflozin, Remogliflozin etabonate or pharmaceutically acceptable salt, solvate, hydrate thereof. The present invention relates to an improved process for preparation of Remog

An efficient and practical synthesis of remogliflozin etabonate, a potent inhibitor of low-affinity Na+-dependent glucose co-transporter (SGLT2)

A practical process for the preparation of remogliflozin etabonate, a prodrug of the selective low-affinity Na+-dependent glucose co-transporter (SGLT2) inhibitor, remogliflozin, is described. We established a chemoselective synthetic route to 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methyl-3H-pyrazol-3-one and an efficient O-glycosylation of this compound with 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide. This synthetic process provided remogliflozin etabonate in a 39% overall yield from commercially available 4-isopropoxybenzaldehyde.

Fluorine-Directed Glycosylation Enables the Stereocontrolled Synthesis of Selective SGLT2 Inhibitors for Type II Diabetes

Inhibition of the sodium-glucose co-transporters (SGLT1 and SGLT2) is a validated strategy to address the increasing prevalence of type II diabetes mellitus. However, achieving selective inhibition of human SGLT1 or SGLT2 remains challenging. Orally available small molecule drugs based on the d-glucose core of the natural product Gliflozin have proven to be clinically effective in this regard, effectively impeding glucose reabsorption. Herein, we disclose the influence of molecular editing with fluorine at the C2 position of the pyranose ring of Phlorizin analogues Remogliflozin Etabonate and Dapagliflozin (Farxiga) to concurrently direct β-selective glycosylation, as is required for biological efficacy, and enhance aspects of the physicochemical profile. Given the abundance of glycosylated pharmaceuticals in diabetes therapy that contain a β-configured d-glucose nucleus, it is envisaged that this strategy may prove to be expansive.

O-glycosylation of 4-(substituted benzyl)-1,2-dihydro-3H-pyrazol-3-one derivatives with 2,3,4,6-tetra-O-acyl-α-D-glucopyranosyl bromide via N1-acetylation of the pyrazole ring

A practical preparation of 4-(substituted benzyl)-3-(2,3,4,6-tetra-O-acyl-β-D-glucopyranosyloxy)-1H-pyrazole derivative 2 is described. O-Glycosylation of 4-(substituted benzyl)-1,2-dihydro-3H-pyrazol-3-one derivative 3 was facilitated by introduction of

CHEMICAL PROCESS

Disclosed herein are processes for preparing glucopyranosyloxypyrazole derivatives and pyrazole intermediates of the same. In particular, the present invention relates to glucopyranosyloxypyrazole derivatives having SGLT2 inhibitory activity and processes

GLUCOPYRANOSYLOXYPYRAZOLE DERIVATIVES AND USE THEREOF IN MEDICINES

The present invention provides glucopyranosyloxypyrazole derivatives represented by the general formula: wherein R represents a hydrogen atom, a lower alkyl group or a group forming a prodrug; one of Q and T represents a group represented by the general f

GLUCOPYRANOSYLOXYPYRAZOLE DERIVATIVES, MEDICINAL COMPOSITIONS CONTAINING THE SAME AND INTERMEDIATES IN THE PRODUCTION THEREOF

The present invention relates to glucopyranosyloxypyrazole derivatives represented by the general formula: wherein R1 represents a hydrogen atom or a lower alkyl group; one of Q1 and T1 represents a group represented by the general formula: while the other represents a lower alkyl group or a halo(lower alkyl) group; and R2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halo(lower alkyl) group or a halogen atom, or pharmaceutically acceptable salts thereof, which have an inhibitory activity on human SGLT2 and are useful as agents for the prevention or treatment of diabetes, diabetic complications or obesity, and to pharmaceutical compositions comprising the same and intermediates thereof.