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EGT1442

EGT1442 structure

CAS No:
1118567-05-7
Formula:
C24H29ClO7
Chemical Name:
EGT1442
Synonyms:
(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;bexagliflozin;UNII-EY00JF42FV;EGT-1442;EGT1442;Bexagliflozin [USAN];THR-1442;EGT0001442;EY00JF42FV
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Bexagliflozin is a potent and selective SGLT2 inhibitor with IC50 value of 5.6 μM /2 nM in SGLT1 /SGLT2 respectively.target: SGLT2IC50: 5.6 μM (SGLT1)/ 2 nM (SGLT2)1) In normal rats and dogs a saturable urinary glucose excretion was produced with an ED50 of 0.38 and 0.09 mg/kg, respectively.2) EGT1442 significantly prolonged the median survival of SHRSP rats.3) EGT1442 dose-dependently reduced HbA1c and blood glucose concentration without affecting body mass or insulin level.

Bexagliflozin is under investigation for the treatment of Type 2 Diabetes Mellitus. Bexagliflozin has been investigated for the treatment of Diabetes Mellitus and Type2 Diabetes Mellitus.

EGT1442 Basic Attributes

Molecular Weight：

464.9 g/mol

Exact Mass：

464.160187

UNII：

EY00JF42FV

Characteristics

PSA：

109 Å²

XLogP3：

2.00350

Density：

1.41

Boiling Point：

671.0±55.0 °C(Predicted)

Flash Point：

359.6±31.5 °C

Refractive Index：

1.642

Drug Information

Drug Indication：

Treatment of type II diabetes mellitus

MeSH：

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

MeSH Entry Terms：

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

EGT1442 Use and Manufacturing

Methods of Manufacturing

Preparation of ((2S, 3R, 4R, 5S, 6R)-2-(4-Chloro-3-(4-(2-Cyclopropoxyethoxy)Benzyl)Phenyl)-6-(Hydroxymethyl)Tetrahydro-2H-Pyran-3, 4, 5-triol [0236] This example describes preparation of (2S, 3R, 4R, 5S, 6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3, 4, 5-triol by reduction of the anomeric OMe and/or OH. (3R, 4S, 5S, 6R)-2-(4-Chloro-3-(4-(2-Cyclopropoxyethoxy)Benzyl)Phenyl)-6-(Hydroxymethyl)-2-Methoxytetrahydro-2H-Pyran-3, 4, 5-Triol Solution [0237] A 30 L glass reactor equipped with a thermometer was charged with crude (3R, 4S, 5S, 6R)-2-(4-chloro-3-(4-(2-cyclopropoxyethoxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3, 4, 5-triol (2.7 kg), DCM (5.4 kg) and acetonitrile (3.2 kg), and the mixture was magnetically stirred until all the solids dissolved under nitrogen sparging. [0238] Triethylsilane Solution: [0239] BFGeneral procedure: To a solution of 16b (2.1 g, 4.2 mmol) in dichloromethane (10.5 mL) and acetonitrile (10.5 mL) at –25 °C under argon was added triethylsilane (2.7 mL, 16.8 mmol). Then boron trifluoride etherate (1.6 mL, 12.6 mmol) was added while maintaining the reaction temperature below –20 °C, and the reaction mixture was stirred for another 4 h at –25 to –20 °C. The reaction was quenched by addition of 5percent sodium bicarbonate until a pH of 7.5 was obtained. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (2 × 50 mL). The combined organic phases were washed with water (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate. The sample was concentrated under reduced pressure to give product crude 7b as a light yellow solid (1.82 g, 92percent yield; HPLC purity: 88.3percent).

Use Classification：

Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:464.9
XLogP3:2.4
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:9
Exact Mass:464.1601810
Monoisotopic Mass:464.1601810
Topological Polar Surface Area:109
Heavy Atom Count:32
Complexity:569
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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