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C-glucoside derivative containing cyclopropane structure and method and application of C- glucoside derivative

A C1-C3, alkyl technology, applied in the field of C-glucoside type 2 sodium-glucose co-transporter inhibitor and its preparation, can solve the problems of hypoglycemia, weight gain and the like

Inactive Publication Date: 2012-09-19
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, hypoglycemia, weight gain and many other problems

Method used

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  • C-glucoside derivative containing cyclopropane structure and method and application of C- glucoside derivative
  • C-glucoside derivative containing cyclopropane structure and method and application of C- glucoside derivative
  • C-glucoside derivative containing cyclopropane structure and method and application of C- glucoside derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 1-{4-Chloro-3-[1-(4-ethoxyphenyl)cyclopropan-1-yl]phenyl}-1-deoxy-β-D-glucopyranose

[0046]

[0047] A. (5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone

[0048] Add 4.71g (20mmol) of 5-bromo-2-chlorobenzoic acid, 20mL of dry dichloromethane, 3.81g (30mmol) of redistilled oxalyl chloride and a drop of DMF to a 100mL dry round bottom flask to obtain a white cloudy mixture Stir overnight at room temperature until the system no longer gasses and becomes a clear solution. Evaporate excess oxalyl chloride and solvent on a rotary evaporator, dissolve the resulting residue with 15mL of dry dichloromethane, add 2.44g (20mmol) phenetole, stir under ice-water bath cooling, add 4.00g (30mmol) Anhydrous aluminum trichloride. After the addition was complete, the resulting mixture was stirred overnight at room temperature.

[0049] The reaction mixture was carefully poured into 200 mL of ice water, stirred, and extracted with 50 mL×3 of dichloromethane. The extract phases were...

Embodiment 2-13

[0067] 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.

[0068]

[0069]

[0070]

Embodiment 14

[0072]

[0073]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 invention relates to the field of medicines relevant to diabetes mellitus, in particular to a type 2 sodium galactose transporter [SGLT2 (sodium-dependent glucose transporter)] inhibitor of a C-glucoside type containing a cyclopropane structure, a preparation method of the type 2 sodium galactose transporter inhibitor, a medicinal composition containing the type 2 sodium galactose transporter inhibitor and application of the type 2 sodium galactose transporter inhibitor in terms of preparation of medicine for the diabetes mellitus. An R1 is one of H, F, Cl, Br, I, OR3, SR4, OCF3, CF3, CHF2, CH2F, alkyl of C1-C3 and a naphthenic base containing 3-5 carbon atoms, an R3 and an R4 are independently selected from alkyl of C1-C3, an R2 is selected from alkyl of C1-C3, cyclopropyl and OR5, and an R5 is one of alkyl of C1-C3 and cyclopropyl.

Description

technical field [0001] The invention relates to the field of medicine related to diabetes. Specifically, the present invention relates to a C-glucoside type 2 sodium glucose cotransporter (SGLT2) inhibitor containing a cyclopropane structure and a preparation method thereof, as well as a pharmaceutical composition containing them, which have a therapeutic effect on diabetes. 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, hypoglycemia, weight gain and many other problems. [0003] Sodium-glucose cotransporter type 2 (SGLT2) is a new target for the treatment of...

Claims

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Application Information

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IPC IPC(8): C07H7/04C07H1/00A61K31/70A61P3/10
CPCC07D309/06C07D309/04C07H1/00A61K31/70C07H7/04A61P3/10
Inventor 赵桂龙吴疆徐为人汤立达邵华王玉丽刘巍谭初兵龚珉
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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