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Phenyl c-glucoside derivatives containing 3-oxoglucose structure, its preparation method and use

The technology of an alkyl group and compound is applied in the field of type 2 sodium-glucose co-transporter inhibitor and its preparation, and can solve the problems of weight gain and the like

Active Publication Date: 2017-03-15
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The antidiabetic drugs currently in clinical use mainly include metformin, sulfonylureas, insulin, thiazolidinediones, α-glucosidase inhibitors and dipeptidyl peptidase-IV inhibitors. It has a good therapeutic effect, but there are safety problems in long-term treatment, such as: liver toxicity, some drugs still have weight gain and many other problems

Method used

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  • Phenyl c-glucoside derivatives containing 3-oxoglucose structure, its preparation method and use
  • Phenyl c-glucoside derivatives containing 3-oxoglucose structure, its preparation method and use
  • Phenyl c-glucoside derivatives containing 3-oxoglucose structure, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 1-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-1-deoxy-3-oxo-β-D-glucopyranose (I-1)

[0043]

[0044] a.

[0045] In a 250mL round bottom flask, add 20.44g (50mmol) compound II-1, 22.83g (150mmol) benzaldehyde dimethyl acetal, 3g camphorsulfonic acid (CSA) and 120mL dry DMF, then heat up at 60°C After stirring overnight, TLC showed that the reaction was complete.

[0046] After the reaction mixture was cooled to room temperature, it was poured into 400 mL of ice water, stirred, and extracted with 200 mL×3 dichloromethane. The combined organic phases were sequentially washed with saturated NaHCO 3 The solution was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated on a rotary evaporator, and the obtained residue was purified by column chromatography to obtain product III-1. White solid, 182-183°C. Yield 83%. 1 HNMR (DMSO-d 6,400MHz)δ:7.45-7.47(m,2H,Ar-H),7.36-7.40(m,4H,Ar-H),7.28(d,1H,J=1.6Hz,Ar-H),7.21(dd ,1H,J=2.0Hz and8.4Hz,Ar-H),...

Embodiment 2-9

[0063] Referring to the operation steps of Example 1, the following compounds were prepared.

[0064]

Embodiment 10

[0066]

[0067] Sieve the active ingredient, pregelatinized starch and microcrystalline cellulose, mix well, add polyvinylpyrrolidone solution, mix, make soft material, sieve, make wet granules, dry at 50-60°C, and carboxymethyl starch Sodium salt, magnesium stearate and talc are pre-screened and then added to the above granules for tableting.

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Abstract

The present invention relates to the field of diabetes-related drugs, specifically to a class of 3-oxoglucose structure-containing phenyl C-glucoside structure type 2 sodium-glucose cotransporter (SGLT2) inhibitors, a preparation method, a drug composition containing the inhibitor, and applications of the inhibitors in preparation of diabetes drugs. The formula I is defined in the instruction, wherein R1 is selected from H, F, Cl, Br, I, C1-C3 alkyl, OR3 and SR4, R2 is selected from C1-C5 alkyl and OR5, and R3-R5 are selected from C1-C5 alkyl.

Description

technical field [0001] The invention relates to the field of medicine related to diabetes. Specifically, the present invention relates to a type 2 sodium glucose co-transporter (SGLT2) inhibitor containing a phenyl C-glucoside structure with a 3-oxoglucose structure and a preparation method thereof, as well as a preparation method thereof, which has a therapeutic effect on diabetes. pharmaceutical composition. Background technique [0002] There are currently about 170 million diabetics in the world, and the vast majority of them are type II (ie, non-insulin-dependent) diabetics. The antidiabetic drugs currently in clinical use mainly include metformin, sulfonylureas, insulin, thiazolidinediones, α-glucosidase inhibitors and dipeptidyl peptidase-IV inhibitors. It has a good therapeutic effect, but there are safety problems in long-term treatment, such as: liver toxicity, some drugs still have weight gain and many other problems. [0003] Sodium-glucose cotransporter type ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/30A61K31/351A61P3/10
CPCY02P20/55
Inventor 赵桂龙王玉丽刘巍吴疆谢亚非刘钰强徐为人汤立达邹美香
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH