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Piperidine derivatives useful for treatment of diebetes

A compound, the technology of dihydropyridine, applied in the field of diseases caused by formation and accumulation, can solve problems such as impairment of growth factor activity

Inactive Publication Date: 2012-05-16
TORRENT PHARMA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the activity of several growth factors such as basic fibroblast growth factor is impaired

Method used

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  • Piperidine derivatives useful for treatment of diebetes
  • Piperidine derivatives useful for treatment of diebetes
  • Piperidine derivatives useful for treatment of diebetes

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0457] N'-(methylsulfonyl)-1-[2-oxo-2-(thien-2-yl)ethyl]-1,4-dihydropyridine-3-carbohydrazide (No. 100 compound) preparation

[0458] method 1

[0459] Into pyridine, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl) in batches at -10°C to 0°C under nitrogen atmosphere ) ethyl], to a stirred suspension of chloride (200 gm, 0.53 mol) in pyridine (1000 ml) was added sodium cyanoborohydride (40 gm, 0.64 mol). The resulting reaction mixture was stirred at 25-30°C for 2 hours. The solid that separated was filtered and sucked dry. The solid was dissolved in dichloromethane and washed with water. The organic layer was separated and dried over sodium sulfate and dichloromethane was evaporated. The isolated solid was filtered, washed with dichloromethane and dried under vacuum at 50-55°C to give the desired product (20 gm) as a yellow solid.

[0460] 1 H NMR (400MHz, DMSO-d 6 )

[0461] δ9.36(s, 1H), 9.12(s, 1H), 8.08-8.07(d, 1H), 8.00-7.99(d, 1H), 7.30-7.28(t, ...

example 2

[0473] Preparation of N'-(methylsulfonyl)-1-[2-oxo-2-(thien-2-yl)ethyl]-1,4-dihydropyridine-3-carbohydrazide (No. 100 compound) Alternatives to

[0474] To 1,2-dimethoxyethane (600ml) and pyridine, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo at -10°C to 0°C - To a stirred cold solution of 2-(2-thienyl)ethyl]chloride (120 gm, 0.32 mol) was added sodium cyanoborohydride (30 gm, 0.48 mol) and stirred at ambient temperature for 2-3 hours. The resulting crude product was filtered and washed with water. The crude product was stirred in water:ethanol (1:1) for 1 hour and filtered. The crude product was dried under vacuum at 55°C for 15 hours to give the desired product (61 gm).

[0475] The crude product (3 gm) was further purified by recrystallization in acetonitrile to give the title product (1.6 gm).

example 3

[0477] N'-(methylsulfonyl)-1-[2-oxo-2-(thiophen-2-yl)ethyl]-1,4,5,6-tetrahydropyridine-3-carbohydrazide (No. 183 compound) preparation

[0478] To a mixture of 10% Pd / C (1 g, 20% w / w) in methanol (25 ml) was added triethylamine (0.47 ml, 3.18 mmol) at room temperature under a nitrogen atmosphere. Subsequent partitioning of pyridine, 3-[[2-(methylsulfonyl)hydrazino]carbonyl]-1-[2-oxo-2-(2-thienyl)ethyl]chloride (1 g, 2.65 mmol) Add in batches to the above mixture. A hydrogen atmosphere (50 mbar) was applied and the reaction was continued for 50 hours at room temperature. The reaction mixture was filtered through Hyflow, the filtrate was distilled, and the residue was suspended in water. The solid obtained above was filtered and dried under vacuum. The crude product obtained above was further purified by silica gel column chromatography using ethyl acetate and hexane as eluents to give a yellow solid product (0.18 g).

[0479] 1 H NMR (400MHz, DMSO-d 6 )δ1.78(2H, s), 2.18...

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Abstract

The present invention relates to a new class of heterocyclic compounds and pharmaceutically acceptable salts thereof, process for preparing the same, pharmaceutical composition containing these compounds and to their use in treatment of diseases caused due to formation and accumulation of AGEs (Advanced Glycation endproducts). The compounds of the present invention are useful for the treatment of diabetic and aging-related complications caused by formation and accumulation of AGEs, such as neuropathy, nephropathy, microangiopathy, retinopathy, hypertension, heart failure, atherosclerosis, Alzheimer's disease & dermatological disorders.

Description

technical field [0001] The present invention relates to a new class of heterocyclic compounds and their pharmaceutically acceptable salts, as well as the preparation method of the heterocyclic compounds and their pharmaceutically acceptable salts, as well as pharmaceutical compositions containing these compounds, and their therapeutic effect on Use in diseases caused by the formation and accumulation of advanced glycation endproducts (Advanced Glycation endproducts, AGE). The compounds of the present invention are useful in the treatment of diabetes and aging-related complications caused by the formation and accumulation of AGEs, such as neuropathy, nephropathy, microvascular disease, retinopathy, hypertension, heart failure, atherosclerosis, Alzheimer's disease (Alzheimer's disease) and dermatological disorders. Background technique [0002] Maillard discovered in 1912 that reducing sugars such as glucose and ribose react with proteins to form brown pigment. Other studies...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/56C07D211/60C07D401/04C07D401/14C07D405/14C07D409/06C07D409/14C07D417/04A61K31/4535A61K31/454A61P3/06
CPCC07D401/14C07D211/60C07D417/04C07D405/14C07D211/56C07D409/14C07D409/06C07D401/04A61P13/12A61P17/00A61P25/00A61P25/28A61P27/02A61P29/00A61P3/06A61P9/00A61P9/04A61P9/10A61P9/12
Inventor C·度特V·查赫维尔拉密施·C·古浦塔马尼施·帕特勒J·寇塔切S·拉塔德J·阿布拉哈S·斯里维斯塔米兰德·罗德S·德斯芬德阿尼塔·查德哈瑞阿米特·K·科萨维尼
Owner TORRENT PHARMA LTD
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