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C-aryl glucoside SGLT2 inhibitor

An alkyl and cyano technology, which can be used in medical preparations containing active ingredients, organic chemistry, pharmaceutical formulations, etc., and can solve the problems of low activity and insufficient efficacy.

Inactive Publication Date: 2009-08-12
马萨诸塞州白鹭有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although there are currently compounds aimed at inhibiting SGLT, these compounds still have defects such as low activity and insufficient efficacy, so more effective compounds still need to be developed in this field

Method used

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  • C-aryl glucoside SGLT2 inhibitor
  • C-aryl glucoside SGLT2 inhibitor
  • C-aryl glucoside SGLT2 inhibitor

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0075] Compound preparation

[0076] Those skilled in the art should understand that after knowing the structure of the compound of the present invention, the compound of the present invention can be obtained by various methods well known in the art and using known raw materials, such as chemical synthesis or extraction from plants, These methods are all included in the present invention. Unless otherwise stated or a method of preparation is provided, the starting materials used in the preparation of the compounds of the present invention or their intermediates are known in the art or are commercially available.

[0077] As a preferred mode of the present invention, the compound of the present invention can be prepared through the following reaction scheme and description.

[0078] Process 1

[0079]

[0080] As shown in Scheme 1, at -78°C, the compound of formula V is treated with n-butyllithium or tert-butyllithium in a mixed solvent of tetrahydrofuran / toluene, and then...

Embodiment 1

[0117] The preparation of embodiment 1 intermediate compound

[0118] 1. Preparation of (2-chloro-5-bromo-phenyl)-(phenyl)-methanone

[0119]

[0120] At room temperature, 41 mL (477 mmol) of oxalyl chloride and 0.64 mL of N,N-dimethylformamide were added to a solution of 100 g (425 mmol) of 2-chloro-5-bromobenzoic acid dissolved in 300 mL of dichloromethane. The mixed solution was stirred overnight at room temperature, and then all volatile components were distilled off under reduced pressure. The resulting solid residue was redissolved in 100 mL of dichloromethane, the solution was cooled to -5°C, and 76 mL (850 mmol) of benzene was added. Then 62.4 g (468 mmol) of aluminum trichloride were added in portions. The reaction mixture was stirred at -3°C for 10 minutes, then slowly warmed to room temperature, and stirring was continued at room temperature for 1 hour. The reaction mixture was poured into a beaker filled with ice, the organic phase was separated, and the aque...

Embodiment 2

[0196] The preparation of embodiment 2 final product

[0197] 1. Preparation of 1-chloro-2-(4-cyclopropylbenzyl)-4-(β-D-glucopyranose-1-yl)-benzene (compound A)

[0198]

[0199] 105 mg (0.18 mmol) of 1-chloro-2-(4-cyclopropylbenzyl)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranose A solution of -1-yl)-benzene and 4.7 mg (0.11 mmol) of lithium hydroxide monohydrate in 1 mL of 2:3:1 THF / methanol / water was stirred at room temperature for 2 h, then concentrated, and the resulting residue was analyzed by preparative HPLC purification.

[0200] Obtained product: 38 mg (51% of theoretical yield).

[0201] 1 H NMR (400MHz, CDCl3) δ 7.33(d, J=8.0Hz, 1H), 7.31(d, J=2.0Hz, 1H), 7.26(dd, J=8.4, 2.4Hz, 1H), 7.05(d, J=8.0Hz, 2H), 6.94(d, J=8.0Hz, 2H), 4.08(d, J=9.2Hz, 1H), 4.06(d, J=14.8Hz, 1H), 4.00(d, J= 14.8Hz, 1H), 3.86(dd, J=12.0, 1.6Hz, 1H), 3.68(dd, J=11.6, 5.2Hz, 1H), 3.47-3.37(m, 3H), 3.28(t, J=8.4 Hz, 1H), 1.85-1.80(m, 1H), 0.92-0.87(m, 2H), 0.62-0.58(m, 2H);

[0202] LC-MS(...

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Abstract

The invention relates to a C-aryl glucoside derivative indicated by a general formula I, as well as a usage and a composition thereof. The C-aryl glucoside derivative has a good effect in inhibiting SGLT. The composition can be separately used or used together with other antidiabetic medicine or other therapeutic agent and can be used for preventing or curing diabetes and other relevant diseases.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a class of C-aryl glucoside derivatives or their isomers, racemates, precursors or pharmaceutically acceptable salts, as well as their uses and compositions. Background technique [0002] According to data released by the World Health Organization, approximately 150 million people worldwide suffer from diabetes. Type I diabetes (IDDM) and type II diabetes (NIDDM) are the two most basic types of diabetes. The pathogenesis of the former is characterized by the inability of the pancreas to secrete insulin, while the pathogenesis of the latter is characterized by slow insulin secretion and insulin resistance. Relatively insufficient insulin. Type II diabetes is the most common type, accounting for about 90% of diabetics. Hyperglycemia is considered a major risk factor for the development of diabetic complications. The main complications of diabetes include retinal disease, cardiovascular dis...

Claims

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Application Information

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IPC IPC(8): C07D309/10A61K31/351A61P3/10
Inventor 陈元伟许百华冯焱
Owner 马萨诸塞州白鹭有限责任公司
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