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C-glucoside derivatives containing saturated six-membered ring as well as preparation method and application thereof

A C1-C3 compound technology, applied in the field of type 2 sodium glucose co-transporter inhibitors and its preparation, can solve problems such as weight gain

Inactive Publication Date: 2011-08-10
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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  • C-glucoside derivatives containing saturated six-membered ring as well as preparation method and application thereof
  • C-glucoside derivatives containing saturated six-membered ring as well as preparation method and application thereof
  • C-glucoside derivatives containing saturated six-membered ring as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] 1-[4-Chloro-3-(cyclohexylmethyl)phenyl]-1-deoxy-β-D-glucopyranose

[0077]

[0078] A. 4-Bromo-1-chloro-2-(cyclohexylmethyl)benzene

[0079] Add 2.19g (10mmol) of 2-chloro-5-bromobenzaldehyde and 10mL of anhydrous tetrahydrofuran into a 100mL round-bottomed flask, cool the solution with an ice-water bath and stir it electromagnetically, and add 11mL (11mmol) dropwise with a constant pressure dropping funnel; 1.0 M) a THF solution of cyclohexylmagnesium bromide. After the dropwise addition, the reaction mixture was stirred at room temperature for one hour and poured carefully into 200 mL of ice water. The pH was adjusted to 3-4 with concentrated hydrochloric acid. The resulting acidic system was extracted twice with 100 mL of dichloromethane, the combined extracts were washed once with saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness on a rotary evaporator to obtain a colorless oily substance (5-bromo- 2-Chlorophenyl)(cyclohexyl)methano...

Embodiment 2-10

[0089] It can be understood that, using the method and process of Example 1, changing R 1 , R 2 The compounds listed in the table below can be obtained.

[0090]

[0091]

[0092]

Embodiment 14

[0094] 1-{4-Chloro-3-[(4-ethylpiperazin-1-yl)methyl]phenyl}-1-deoxy-β-D-glucopyranose

[0095]

[0096] A. 4-Bromo-1-chloro-2-[(4-ethylpiperazin-1-yl)methyl]benzene

[0097]Add 2.84g (10mmol) 5-bromo-2-chlorobenzyl bromide, 1.14g (10mmol) 1-ethylpiperazine, 1.01g (10mmol) triethylamine and 20mL anhydrous tetrahydrofuran to a 100mL round bottom flask , the resulting reaction mixture was stirred overnight at room temperature and then poured into 200 mL of water, extracted twice with 100 mL of dichloromethane, the combined extraction liquid was washed once with saturated brine, dried over anhydrous sodium sulfate, and evaporated to dryness on a rotary evaporator to obtain Off-white solid, 4-bromo-1-chloro-2-[(4-ethylpiperazin-1-yl)methyl]benzene. 3.11g, yield 98%, ESI-MS, m / z=317.2 ([M( 79 Br)+1]), 319.3([M( 81 Br)+1]).

[0098] B. 1-{4-chloro-3-[(4-ethylpiperazin-1-yl)methyl]phenyl}-1-deoxy-β-D-glucopyranose

[0099] In a 100mL round bottom flask, add 3.11g (9.8mmol) of ...

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Abstract

The invention relates to the field of medicines related to diabetes. More specifically, the invention relates to a sodium galactose transporter type 2 (SGLT2) inhibitor having a structure of C-glucoside derivatives containing saturated six-membered ring, a preparation method thereof, a pharmaceutical composition containing the derivatives and application of the derivatives in preparing diabetes medicines, wherein X and Y are defined as the followings: (1) X = Y = carbon atom; (2) X = Y = nitrogen atom; (3) X = nitrogen atom and Y = oxide atom; and (4) X = nitrogen atom and Y = carbon atom. Other groups are defined as specification.

Description

technical field [0001] The invention relates to the field of medicine related to diabetes. Specifically, the present invention relates to a sodium glucose co-transporter type 2 (SGLT2) inhibitor containing a saturated six-membered ring C-glucoside structure that has a therapeutic effect on diabetes, a preparation method thereof, and a pharmaceutical composition containing them. 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 2 (SGLT2) is a new target for the ...

Claims

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Application Information

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IPC IPC(8): C07D309/10C07D405/10A61K31/351A61K31/453A61K31/496A61K31/5377A61P3/10
CPCC07D407/10A61K31/5375A61K31/4433C07D405/10C07D309/10A61K31/351A61K31/496A61P3/10
Inventor 赵桂龙邵华刘巍王玉丽汤立达徐为人龚珉谭初兵张士俊刘冰妮
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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