1359976-62-7

Basic information

• Product Name: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-bromophenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol
• Synonyms: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-bromophenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol
• CAS NO: 1359976-62-7
• Molecular Weight: 649.533
• Mol File: 1359976-62-7.mol

Chemical Properties

• CAS DataBase Reference: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-bromophenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-bromophenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol(1359976-62-7)
• EPA Substance Registry System: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-bromophenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol(1359976-62-7)

Safety Data

• Hazardous Substances Data: 1359976-62-7(Hazardous Substances Data)

Upstream product

• 1359976-25-2 C₁₇H₂₆O₇ 
• 34881-45-3 1-bromo-2-isopropyl-4-methoxy-benzene 
• 853271-15-5 2-(2-bromo-5-methoxyphenyl) propan-2-ol 
• 108-24-7 acetic anhydride 
• 35450-36-3 methyl 2-bromo-5-methoxybenzoate 
• 1122-91-4 4-bromo-benzaldehyde 
• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 
• 1240304-54-4 1,5-dibromo-2-(methoxymethoxy)-4-(propan-2-yl)benzene 
• 74-88-4 methyl iodide 

Downstream Products

• 1369431-11-7 C₄₅H₆₃N₃O₁₂ 
• 1240305-17-2 (E)-N-(1-((2-(dimethylamino)ethyl)amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-isopropyl-4-methoxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-2,2-dimethylbut-3-enamide 
• 1369430-78-3 C₄₁H₅₃NO₁₃ 

Relevant articles and documents

Discovery of potent, low-absorbable sodium-dependent glucose cotransporter 1 (SGLT1) inhibitor SGL5213 for type 2 diabetes treatment

A new series of C-phenyl D-glucitol derivatives was designed and synthesized, and their SGLT1 inhibitory potency and absorbability were evaluated. We also investigated whether kidney drug retention could be avoided by creating molecules with different excretion pathways. To achieve a class of molecules with low absorption and that were excreted in bile, optimized synthesis was performed to bring the ClogP value and the topological polar surface area to within the appropriate ranges. Compounds 34d and 34j were poorly absorbed, but the absorbed compounds were mainly excreted in bile. Thus, smaller amounts of persistent residue in the kidneys were observed. Since 34d exerted a glucose-lowering effect at a dose of 0.3 mg/kg (p.o.) in SD rats, this compound (SGL5213) could be a clinical candidate for the treatment of type 2 diabetes.

METHOD FOR PRODUCING 1,5-ANHYDRO-1-SUBSTITUTED PHENYL-D-GLUCITOL COMPOUNDS

PROBLEM TO BE SOLVED: To provide a novel method for producing 1,5-anhydro-1-substituted phenyl-D-glucitol compounds useful as medicines having the action of inhibiting sodium-dependent glucose cotransporters 1. SOLUTION: The present invention provides a method for producing 1,5-anhydro-1-substituted phenyl-D-glucitol compounds represented by formula (XI), wherein, compounds represented by formula (II) are converted through a plurality of steps to produce the compounds represented by formula (XI). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPO&INPIT

PROPHYLACTIC OR THERAPEUTIC DRUG FOR CONSTIPATION

New drugs useful in the prevention or treatment of constipation are provided, in which SGLT1 inhibiting compounds, in particular, a 4-isopropylphenyl glucitol compound represented by the following formula (I), or pharmaceutically acceptable salts thereof

CRYSTAL FORM OF 4-ISOPROPYLPHENYL GLUCITOL COMPOUND AND PROCESS FOR PRODUCTION THEREOF

A highly stable crystal of (1S)-1,5-anhydro-1-[5-(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}benzyl)-2-methoxy-4-(propan-2-yl)phenyl]-D-glucitol, and a process for producing the crystal are provided. Specifically, an ethanolate having the following physical properties, and a plurality of other crystal forms transformed from the ethanolate are provided: (a) Having peaks at 2θ=5.9 degrees, 17.1 degrees, 17.6 degrees and 21.5 degrees in X-ray powder diffraction (Cu—Kα);(b) Showing characteristic absorption bands at 3538 cm?1, 3357 cm?1, 2964 cm?1, 1673 cm?1, 1634 cm?1 and 1505 cm?1 in an infrared absorption spectrum; and(c) Having a melting point in a vicinity of 111° C.

4 -ISOPROPYLPHENYL GLUCITOL COMPOUNDS AS SGLTL INHIBITORS

The present invention provides 4-isopropylphenyl glucitol compounds which have no tendency to accumulate in the body and which inhibit SGLT1 activity to suppress postprandial hyperglycemia (or impaired glucose tolerance) through suppression of glucose absorption in the small intestine, whereby the compounds, for example, can suppress the onset of diabetes and metabolic syndrome or can treat these diseases. A 4-isopropylphenyl glucitol compound represented by the following formula (I) or a pharmaceutically acceptable salt thereof: [Chem. 1] wherein R1 represents a hydrogen atom, etc., R2 represents a methyl group, etc., R3 represents a C1-4 alkyl group substituted with an amino group(s), etc., and R4 represents a hydrogen atom, etc.