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C-indican derivative

A compound and alkyl technology, applied in the field of medicine, can solve problems such as insufficient net energy

Active Publication Date: 2013-01-09
SHANDONG XUANZHU PHARMA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this pathway does not directly contribute to the pathophysiology of type 2 diabetes, lowering blood glucose by increasing renal glucose excretion induces a net energy deficit, promotes weight loss and indirectly improves obesity symptoms

Method used

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Examples

Experimental program
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Effect test

preparation example Construction

[0115] Step 1 Preparation of compound a

[0116] Dissolve the raw material 1 and N-methylmorpholine in THF, cool under the protection of nitrogen, slowly add trimethyl silicon chloride dropwise, keep the temperature, raise the temperature and stir the reaction after completion, then stir the reaction at room temperature, add toluene to dilute and cool. Water was added to maintain the temperature, the organic phase of the reaction mixture was separated, and washed with aqueous sodium dihydrogen phosphate, water, and saturated brine. Rotary evaporation gave a pale yellow oil a.

[0117] Step 2 Preparation of compound b

[0118] The dichloromethane solution of aluminum trichloride was cooled to 0°C, raw material 3 was slowly added, and the mixture was kept at 0°C for 1 h, and then the dichloromethane solution of raw material 2 was slowly added dropwise. The reaction was detected until the end of the reaction, and the reaction mixture was poured into ice water. It was extracted three t...

Embodiment 1

[0163] Example 1 β-1'-deoxy-1'-(4-chloro-3-(1a,2,7,7a-tetrahydro-1H-cyclopropyl[b]naphthalene-4-methylene)benzene) -Glucose acetal (Compound 1) Preparation

[0164]

[0165] Step 1 Preparation of 2,3,4,6-tetra(trimethylsilyl ether)-gluconolactone

[0166]

[0167] Dissolve raw material 1 (239g, 1.34mol) and N-methylmorpholine (1.18L, 10.73mol) in THF (2.4L), cool to -5°C under nitrogen protection, and slowly add trimethyl silicon chloride dropwise (1022mL, 8.05mol), keep the temperature of the dripping process not exceeding 5℃, after completion, raise the temperature to 35℃ and stir for 5h, then stir at room temperature for 15h, add toluene to dilute and cool to 0-5℃, then add water to keep the temperature not exceeding 10 At °C, the organic phase of the reaction mixture was separated and washed with aqueous sodium dihydrogen phosphate, water and saturated brine. By rotary evaporation, 593.2 g of light yellow oily 2,3,4,6-tetrakis(trimethylsilyl ether)-gluconolactone was obtain...

Embodiment 2

[0189] Example 2 β-1'-deoxy-1'-(4-chloro-3-(3,3a,4,9,9a-hexahydronaphthalene[2,3-c]furan-6-methylene)benzene )-Glucose acetal (compound 2) Preparation

[0190]

[0191] Reference Example 1 to obtain the compound β-1'-deoxy-1'-(4-chloro-3-(3,3a,4,9,9a-hexahydronaphthalene[2,3-c]furan-6-methylene Benzene)-glucose acetal. LC-MS(M+H) + :461.

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Abstract

The invention belongs to the technical field of medicine, and particularly relates to C-indican derivative as shown in general formula (I), the pharmaceutically acceptable salt of the C-indican derivative, the easily-hydrolyzed ester of the C-indican derivative, and the stereoisomer and the intermediate of the C-indican derivative. The invention specifically relates to the C-indican derivative taken as sodium-dependent glucose transporters (SGLT) inhibitor, the pharmaceutically acceptable salt of the C-indican derivative, the easily-hydrolyzed ester of the C-indican derivative, and the stereoisomer and the intermediate of the C-indican derivative. The C-indican derivative provided by the invention not only can be used for the diabetes mellitus such as the insulin dependent diabetes mellitus (I type diabetes mellitus), the non-insulin dependent diabetes mellitus (II type diabetes mellitus) and the like, but also can be used for the treatment and the prevention of various mellitus-related diseases such as the insulin-resistant disease and the fatness. R1, R2, R3, R4, R5, R6a, R6b, R6c, W, M, n and A are defined in the specification.

Description

1. Technical field [0001] The invention belongs to the technical field of medicine and relates to C-glycoside derivatives, their pharmaceutically acceptable salts, their easily hydrolyzed esters, their stereoisomers and intermediates. Specifically, it relates to C-glycoside derivatives as sodium-glucose cotransporter (SGLT) inhibitors, their pharmaceutically acceptable salts, their easily hydrolyzed esters, their stereoisomers and intermediates. The C-glycoside derivatives of the present invention can be used in diabetes such as insulin-dependent diabetes (type I diabetes) and non-insulin-dependent diabetes (type II diabetes), as well as various diseases including insulin resistance diseases and obesity. The treatment of various diabetes-related diseases and the prevention of these diseases. 2. Background technology [0002] Approximately 100 million people worldwide suffer from type II diabetes, which is characterized by hyperglycemia due to excessive hepatic glucose production...

Claims

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Application Information

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IPC IPC(8): C07D309/04C07D407/10C07D493/04C07D493/10A61K31/351A61K31/357A61P3/10
Inventor 松山皓治张蕙
Owner SHANDONG XUANZHU PHARMA TECH CO LTD
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