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C-glucoside derivative containing fused phenyl ring or pharmaceutically acceptable salt thereof, process for preparing same, and pharmaceutical composition comprising same

一种药物学、化合物的技术，应用在C-葡糖苷衍生物或其药物学可接受的盐领域，能够解决低口服吸收性等问题

Active Publication Date: 2018-10-23
JEIL PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Phlorizin is extracted from the bark of the apple tree and was the first substance evaluated as an SGLT inhibitor in which it has antidiabetic activity but has low oral absorption and is absorbed in the intestinal tract , causing gastrointestinal problems or diarrhea, which has kept it from being developed as a drug

Method used

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  • C-glucoside derivative containing fused phenyl ring or pharmaceutically acceptable salt thereof, process for preparing same, and pharmaceutical composition comprising same
  • C-glucoside derivative containing fused phenyl ring or pharmaceutically acceptable salt thereof, process for preparing same, and pharmaceutical composition comprising same
  • C-glucoside derivative containing fused phenyl ring or pharmaceutically acceptable salt thereof, process for preparing same, and pharmaceutical composition comprising same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0195] Example 1. Preparation of (2R, 3S, 4R, 5R, 6S)-2-(hydroxymethyl)-6-(7-(4-methoxybenzyl)-4-methyl-2, 3-Dihydro-1H-inden-5-yl)tetrahydro-2H-pyran-3,4,5-triol

[0196] Step 1. Synthesis of ethyl 7-methyl-2,3-dihydro-1H-indene-4-carboxylate (1-1)

[0197]

[0198] A mixture of ethyl sorbate (25.0 mL, 170 mmol, TCI reagent) and 1-pyrrolidinyl-1-cyclopentene (24.8 mL, 170 mmol, TCI reagent) in xylene (100 mL) was stirred at reflux overnight. After the reaction was complete, the volatile solvent was evaporated under reduced pressure. EtOAc was added to the resulting mixture. The organic layer was washed with brine, after which the resulting product was dissolved in anhydrous MgSO 4 Dry over, filter and concentrate in vacuo. The crude compound was used in the following step without additional purification. Will S 8 (5.45 g, 170 mmol) was added to the crude compound. The reaction mixture was stirred at 250°C for 2 hours. After the reaction was complete, the resul...

Embodiment 2 and 3

[0225] The target compounds of Examples 2 and 3 were obtained by the method shown in Example 1.

Embodiment 2

[0226] Example 2. Preparation of (2S,3R,4R,5S,6R)-2-(7-(4-ethoxybenzyl)-4-methyl-2,3-dihydro-1H- Inden-5-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

[0227]

[0228] 1 H NMR (400MHz, CD 3 OD); δ7.10(s, 1H), 7.03(d, J=8.4Hz, 2H), 6.76(d, J=8.8Hz, 2H), 4.45(d, J=8.8Hz, 1H), 3.97( q, J=6.8Hz, 2H) 3.88-3.84(m, 3H), 3.67-3.48(m4H), 3.40-3.38(m, 2H), 2.84(t, J=7.6Hz, 2H), 2.73(t, J=7.6Hz, 2H), 2.28(s, 3H), 02.02-1.97(m, 2H), 1.35(t, J=6.8Hz, 3H)

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Abstract

The present invention relates to a C-glucoside derivative containing a fused phenyl ring or a pharmaceutically acceptable salt thereof, a process for preparing the same, a pharmaceutical composition comprising the same, a use thereof, and a double inhibition process of SGLT1 and SGLT2 using the same. A novel compound of the present invention has a double inhibitory activity of SGLT1 and SGLT2, andcan be effectively used as a therapeutic agent for diabetes.

Description

technical field [0001] The present invention relates to C-glucoside derivatives having a fused phenyl ring or pharmaceutically acceptable salts thereof, processes for their preparation, pharmaceutical compositions containing them, their use and their use for dual inhibition of sodium-glucose co-transporter 1 (SGLT1) and sodium-glucose co-transporter 2 (SGLT2) approach. Background technique [0002] Diabetes is a disease in which various complications develop, such as abnormalities of peripheral nerves and autonomic nerves, disease syndromes of eyes, feet, and kidneys, vascular diseases, etc., which are increased blood sugar due to decreased secretion and function of insulin. [0003] It is known that diabetes is generally divided into two types: type I and type II. Type I often occurs in children, mainly due to congenital factors, and these patients need life-long insulin injections because the pancreas cannot secrete insulin, and they also need to maintain blood sugar at a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203A61K31/7034
CPCA61K31/7034C07H15/203A61P3/10C07D309/10A41D13/1107A62B23/02B01D46/0005B01D46/4227C07H7/04Y02P20/55
Inventor 南骏祐金钟烨金经勋李贞美金志玧朴智善J·金朴胤善金政民
Owner JEIL PHARM CO LTD
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