333359-90-3

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-methoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol is used as an inhibitor of sodium-dependent glucose cotransporter 2 (SGLT2) for the treatment of type 2 diabetes. It works by blocking the reabsorption of glucose in the kidneys, leading to increased glucose excretion and reduced blood glucose levels.
(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-methoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol may also have potential applications in other industries, such as in the development of new drug delivery systems or as a building block for the synthesis of other bioactive compounds. However, further research and development would be required to explore these possibilities.

Upstream product

• 1210040-47-3 (2S, 3R, 4S, 5S, 6R)-2-(3-(4-methoxybenzyl)-4-chlorophenyl)-tetrahydro-6-(hydroxymethyl)-2-methoxy-2H-pyran-3,4,5-triol 
• 864070-19-9 [4-(5-bromo-2-chloro-benzyl)-phenoxy]-tert-butyl-dimethyl-silane 
• 1204220-63-2 (2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 864070-37-1 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 80-48-8 methyl p-toluene sulfonate 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 
• 333361-49-2 (5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone 
• 333361-51-6 4-bromo-1-chloro-2-(4-methoxybenzyl)benzene 
• 864070-18-8 4-(5-bromo-2-chlorobenzyl)phenol 

Downstream Products

• 872980-39-7 1-chloro-2-(4-methoxy-benzyl)-4-[2,3-O-(2,3-dimethoxy-buta-2,3-diyl)-β-D-glucopyranos-1-yl]-benzene 
• 881636-93-7 C₂₆H₃₃ClO₈ 
• 872980-35-3 1-chloro-2-(4-methoxy-benzyl)-4-(6-desoxy-6-iodo-β-D-glucopyranos-1-yl)-benzene 
• 1225326-91-9 C₃₉H₃₇ClO₆ 
• 1079083-63-8 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 915095-99-7 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate 
• 864070-44-0 empagliflozin 

Relevant academic research and scientific papers

GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS

The present invention is directed to glucopyranose derivatives of formula (I), pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS

The present invention is directed to glucopyranose derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

THE PRESENT INVENTION RELATES TO PROCESS FOR THE PREPARATION OF D-GLUCITOL, 1,5- ANHYDRO-1-C-[4-CHLORO-3-[[4-[[(3S)-TETRAHYDRO-3-FURANYL] OXY]PHENYL] METHYL]PHENYL]-, (1S) AND ITS CRYSTALLINE FORMS THEREOF.

The present invention relates to process for the preparation of D-glucitol, 1,5- anhydro-l-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl] methyl]phenyl]-, (1S) formula- 1 and its crystalline forms thereof.

Design, synthesis, and biological evaluation of deuterated C-aryl glycoside as a potent and long-acting renal sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes

SGLT2 inhibitors deuterated at sites susceptible to oxidative metabolism were found to have a slightly longer tmax and half-life (t 1/2), dose-dependent increase in urinary glucose excretion (UGE) in rats, and slightly superior effects on UGE in dogs while retaining similar in vitro inhibitory activities against hSGLT2. In particular, deuterated compound 41 has the potential to be a robust long-acting antidiabetic agent.

PROCESSES FOR THE PREPARATION OF SGLT2 INHIBITORS

Provided are processes for the preparation of complexes that are useful in purifying compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The processes can reduce the number of steps needed to obtain the target compounds and the complexes formed in the processes are typically provided in a crystalline form.

DEUTERATED BENZYLBENZENE DERIVATIVES AND METHODS OF USE

Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions that are affected by SGLT inhibition.

GLUCOPYRANOSYL-SUBSTITUTED BENZONITRILE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING SUCH COMPOUNDS, THEIR USE AND PROCESS FOR THEIR MANUFACTURE

Glucopyranosyl-substituted benzonitrile derivative of formula (I) are disclosed, wherein R3 denotes hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, iso-butyl, tert-butyl, 3-methyl-but-1-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 2-hydroxyl-ethyl, hydroxymethyl, 3-hydroxy-propyl, 2-hydroxy-2-methyl-prop-1 -yl, 3- hydroxy-3-methyl-but-1-yl, 1-hydroxy-1-methyl-ethyl, 2,2,2-trifluoro-1-hydroxy-1-methyl-ethyl, 2,2,2-trifluoro-1-hydroxy-1 -trifluoromethyl-ethyl, 2-methoxy-ethyl, 2-ethoxy-ethyl, hydroxy, methyloxy, ethyloxy, isopropyloxy, difluoromethyloxy, trifluoromethyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, (S)-tetrahydrofuran-3-yloxy, (R)-tetrahydrofuran-3-yloxy, tetrahydropyran-4-yloxy, 1-acetyl-piperidin-4-yloxy, 2-methyloxy-ethyloxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylsulfinyl, ethylsulfonyl, trimethylsilyl and cyano, or a derivative thereof wherein one or more hydroxyl groups of the β-D-glucopyranosyl group are acylated with groups selected from (C1-18-alkyl)carbonyl, (C1-18-alkyl)oxycarbonyl, phenylcarbonyl and phenyl-(C1-3-alkyl)-carbonyl; including tautomers, stereoisomers thereof or mixtures thereof; and physiologically acceptable salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.

D-xylopyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture

A D-Xylopyranosyl-substituted phenyl compound of general formula I wherein the groups R1 to R5, X, Z and R7a, R7b, R7c are defined as in claim 1, have an inhibiting effect on the sodium-dependent glucose cotransporter SGLT. The present invention also relates to pharmaceutical compositions for the treatment of metabolic disorders.

D-pyranosyl-substituted phenyl derivatives, medicaments containing such compounds, their use and process for their manufacture

D-pyranosyl-substituted phenyls of general formula I [image] wherein the groups R1 to R5, X, Z and R7a, R7b, R7c are defined as in claim 1, have an inhibiting effect on the sodium-dependent glucose cotransporter SGLT. The present invention also relates to pharmaceutical compositions for the treatment of metabolic disorders.