898538-44-8

Upstream product

• 16331-45-6 p-ethylbenzoyl chloride 
• 13659-23-9 2-Bromo-5-chlorophenol 
• 1036955-11-9 (5-bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone 

Downstream Products

• 1036955-12-0 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-5-(4-ethylbenzyl)-2-methoxyphenyl)tetrahydro-2H-pyran-2-ol 
• 1061314-98-4 2-bromo-5-chloro-4-(4-ethylbenzyl)phenol 
• 1221506-18-8 2,3,4,6-tetra-O-benzyl-1-C-[4-chloro-5-(4-ethylbenzyl)-2-methoxyphenyl]-5-thio-D-glucopyranose 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel C-aryl D-glucofuranosides as sodium-dependent glucose co-transporter 2 inhibitors

Novel C-aryl-d-glucofuranosides were synthesized and evaluated for their capacity to inhibit human sodium-dependent glucose co-transporter 2 (hSGLT2) and hSGLT1. Compound 21q demonstrated the best in vitro inhibitory activity against SGLT2 in this series (EC50 = 0.62 μM).

(1 S)-1,5-anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio- d -glucitol (TS-071) is a potent, selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for type 2 diabetes treatment

Derivatives of a novel scaffold, C-phenyl 1-thio-d-glucitol, were prepared and evaluated for sodium-dependent glucose cotransporter (SGLT) 2 and SGLT1 inhibition activities. Optimization of substituents on the aromatic rings afforded five compounds with potent and selective SGLT2 inhibition activities. The compounds were evaluated for in vitro human metabolic stability, human serum protein binding (SPB), and Caco-2 permeability. Of them, (1S)-1,5-anhydro-1-[5- (4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-d-glucitol (3p) exhibited potent SGLT2 inhibition activity (IC50 = 2.26 nM), with 1650-fold selectivity over SGLT1. Compound 3p showed good metabolic stability toward cryo-preserved human hepatic clearance, lower SPB, and moderate Caco-2 permeability. Since 3p should have acceptable human pharmacokinetics (PK) properties, it could be a clinical candidate for treating type 2 diabetes. We observed that compound 3p exhibits a blood glucose lowering effect, excellent urinary glucose excretion properties, and promising PK profiles in animals. Phase II clinical trials of 3p (TS-071) are currently ongoing.

BENZYLIC GLYCOSIDE 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 which are affected by SGLT inhibition.

SPIROHETEROCYCLIC GLYCOSIDES 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 which are affected by SGLT inhibition.

1-THIO-D-GLUCITOL DERIVATIVES

The present invention provides a 1-thio-D-glucitol compound of the following formula, which shows the action of inhibiting the activity of SGLT2, a pharmaceutically acceptable salt of the compound, or a hydrate of the compound or the salt; and a pharmaceu