333361-51-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-1-chloro-2-(4-methoxy-benzyl)-benzene is used as a chemical intermediate for the synthesis of Dapagliflozin-D5 (D185372), a labelled analogue of Dapagliflozin (D185370). Dapagliflozin is a selective sodium-glucose cotransporter-2 (SGLT2) inhibitor that reduces renal glucose reabsorption, making it an effective treatment for patients with type 2 diabetes. 4-Bromo-1-chloro-2-(4-methoxy-benzyl)-benzene plays a crucial role in the development of this medication, facilitating its production and enhancing its therapeutic potential.

Upstream product

• 21900-52-7 5-bromo-2-chloro-benzoyl chloride 
• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 333361-49-2 (5-bromo-2-chlorophenyl)(4-methoxyphenyl)methanone 

Downstream Products

• 461432-26-8 dapagliflozin 
• 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 
• 1204220-65-4 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-2-d-6-(hydroxymethyl)tetrahydro-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 
• 1204219-80-6 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(ethoxy-d5)benzyl)-phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1204219-68-0 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(ethoxy-1,1-d2)benzyl)-phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1204219-27-1 (2R,3R,4S,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-2-d-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 333359-90-3 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-methoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1204219-88-4 (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(methoxy-d3)benzyl)-phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 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 
• 912917-83-0 (3R,4S,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 

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.

Synthetic method for empagliflozin related substance IMPD

The invention discloses a synthetic method for empagliflozin related substance IMPD. In a current synthetic method of IMPD, a whole synthetic route is longer and the total yield is lower. The synthetic method provided by the invention comprises the following steps: performing hydroxylation by using (2-chloro-5-iodophenyl)(4-fluorophenyl)methanone as a raw material to obtain (2-chloro-5-iodophenyl)(4-hydroxyphenyl)methanone, performing a reaction by using a carbonyl reducing agent to obtain 4-(5-iodo-2-chlorobenzyl)phenol, protecting phenolic hydroxyl groups by using protecting groups such as TBDMS, performing metallization of aromatic iodide by adopting a relatively stable and safe Grignard reagent i-PrMgCl.LiCl, performing methyl glucoside reduction by using a Lewis acid catalyst, and finally performing quenching to obtain the empagliflozin related substance IMPD. The synthetic method provided by the invention has the advantages of an abundant raw material source, a simple, quick andhigh-efficiency reaction, milder reaction conditions, a higher total yield and low costs.

Processes for the Preparation of SGLT-2 Inhibitors, Intermediates Thereof

The present invention relates to novel, improved processes for the preparation of sodium glucose co-transporter 2 (SGLT-2) inhibitors and novel intermediates thereof. More particularly, the present invention relates to a novel, improved process for the preparation of gliflozin compounds such as empagliflozin and dapagliflozin, intermediates thereof. The product obtained from the processes of present invention may be amorphous or crystalline, or in the form of amorphous/crystalline solid dispersions/solutions with pharmaceutically acceptable polymers and preparation process thereof. Also, the products obtained from the present invention may be used for the preparation of medicaments for the prevention and/or treatment of diseases and conditions associated with SGLT-2 inhibition.

Carbon glucoside sodium glucose transport protein body 2 inhibitor

The invention relates to a carbon glucoside sodium glucose transport protein body 2 inhibitor, a preparation method and an application of the inhibitor. The carbon glucoside sodium glucose transport protein body 2 inhibitor has a structure as shown in general formula (I) as shown in the specification.

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.

OPTICALLY PURE BENZYL-4-CHLOROPHENYL-C-GLUCOSIDE DERIVATIVE

The present invention belongs to the field of pharmaceutical technology, more specifically relates to optically pure benzyl-4-chlorophenyl-C-glucoside derivatives represented by formulae (II) and (III), a process for preparing these compounds and intermediates thereof, a pharmaceutical formulation and a pharmaceutical composition containing these compounds, and the use of the optically pure benzyl-4-chlorophenyl-C-glucoside derivative as a sodium glucose co-transporter (SGLT) inhibitor in manufacture of a medicament for treating and/or preventing diabetes mellitus (including insulin-dependent diabetes mellitus and non-insulin-dependent diabetes mellitus) or diabetes-associated diseases (including insulin resistance disease and obesity)

Optically pure benzyl-4-chlorophenyl-C-glucoside derivatives as SGLT inhibitors (diabetes mellitus)

The present invention belongs to the field of pharmaceutical technology, more specifically relates to optically pure benzyl-4-chlorophenyl-C-glucoside derivatives represented by formulae (II) and (III), a process for preparing these compounds and intermediates thereof, a pharmaceutical formulation and a pharmaceutical composition containing these compounds, and the use of the optically pure benzyl-4-chlorophenyl-C-glucoside derivative as a sodium glucose co-transporter (SGLT) inhibitor in manufacture of a medicament for treating and/or preventing diabetes mellitus (including insulin-dependent diabetes mellitus and non-insulin-dependent diabetes mellitus) or diabetes-associated diseases (including insulin resistance disease and obesity) or

OPTICALLY PURE BENZYL-4-CHLOROPHENYL-C-GLUCOSIDE DERIVATIVE

The present invention relates to a pharmaceutical technology, and more specifically, to optically pure benzyl-4-chloro-phenyl glucoside derivatives represented by the chemical formula II and III or a pharmaceutically acceptable salt thereof. The present invention also relates to a method for preparing the compounds and intermediates thereof, pharmaceutical formulations and pharmaceutical compositions containing the compounds, and the use of the optically pure benzyl-4-chloro-phenyl glucoside derivatives as sodium glucose co-transporter (SGLT) inhibitors for the prevention and treatment of the diabetes including the insulin dependent diabetes mellitus and non-insulin dependent diabetes mellitus and the diabetes-related deseases such as insulin-resistant diseases and obesity.COPYRIGHT KIPO 2015

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.