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Derivatives of benzothiazines, preparation thereof and application thereof as drugs

A benzo, thiazine technology, applied in the field of benzothiazine derivatives, can solve problems such as failure to reach the blood sugar target value

Inactive Publication Date: 2012-02-01
PIERRE FABRE MEDICAMENT SAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, despite available treatments, many patients with type 2 diabetes do not achieve recommended blood glucose targets (notably HbA 1c )

Method used

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  • Derivatives of benzothiazines, preparation thereof and application thereof as drugs
  • Derivatives of benzothiazines, preparation thereof and application thereof as drugs
  • Derivatives of benzothiazines, preparation thereof and application thereof as drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] (4-Hydroxy-2-methyl-1,1-dioxide-2H-benzo[e][1,2]thiazin-3-yl)(naphthalene-2-yl)methanone

[0111]

Embodiment 1A

[0112] Example 1A -2-(2-(naphthalene-2-yl)-2-oxoethyl)benzo[d]isothiazol-3(2H)-one-1,1-dioxide

[0113] Add saccharin (25 g, 136 mmol) and DMF (350 mL) into a three-necked flask equipped with a thermometer and a condenser. The medium was inerted by successive exchanges of vacuum / nitrogen (3 times). Sodium hydride (6 g, 150 mmol) was added slowly, followed by 2-bromo-1-(naphthalen-2-yl)ethanone (37.4 g, 150 mmol). The reaction medium is heated to 65° C. for 4 hours and subsequently cooled to room temperature. The resulting precipitate was filtered, rinsed with water and dried to constant weight to obtain the product 1A 37 g of milky white solid (HPLC: RT = 4.97 min, 100%). A second crop of product was obtained by adding water to the filtrate. The resulting precipitate was filtered, rinsed with water and then a minimum amount of ethyl to obtain 10 g of product after drying (HPLC: RT = 4.97 min, 93%). The overall yield of the reaction was 96%.

[0114] 1 H NMR, dmso-d 6...

Embodiment 1B

[0116] Example 1B -(4-Hydroxy-1,1-dioxide-2H-benzo[e][1,2]thiazin-3-yl)(naphthalen-2-yl)methanone

[0117] Under an inert atmosphere, ethanol (165 mL) was added to a two-necked flask fitted with a condenser, followed by slow addition of sodium sliced ​​and rinsed with heptane (8 g, 347 mmol). After the addition is complete, the reaction medium is heated to 70° C. until the sodium has completely reacted. The reaction was then cooled to room temperature and compound was added rapidly 1A (47 g, 131 mmol). Intense vermilion and subsequent blood red coloration occurs in addition to the dense precipitate. The reaction medium is heated briefly to its solidification temperature of 60°C. It was then cooled to room temperature and diluted with 500 mL of ethyl acetate. Then 1N aqueous HCl was added until a pale yellow suspension was obtained. The precipitate was filtered and rinsed with water and a minimum of 50 / 50 water / ethanol mixture. Subsequent vacuum drying to constant weigh...

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PUM

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Abstract

The object of the present invention is benzothiazine derivatives having the capability of inhibiting 11[beta]-HSD1 not only at an enzymatic level but also at a cell level. The compounds of the present invention are of general formula (I). Wherein notably R1 represents a hydrogen or OR1 represents an ester or an ether. R2 represents a naphthyl or a 1, 2, 3, 4-tetrahydro-naphthalene or a biphenyl or phenyl pyridine or a substituted phenyl. R3 represents a methyl or ethyl; R4 and R'4 represent a hydrogen.

Description

technical field [0001] The present invention relates to benzothiazine derivatives, their preparation methods, pharmaceutical compositions containing them and their use as drugs for treating and / or preventing type II diabetes, obesity, dyslipidemia, arterial hypertension and atherosclerosis . The compounds are also useful for the treatment and / or prevention of hyperglycemia, lactose intolerance, insulin resistance, hypertriglyceridemia, hypercholesterolemia, restenosis, pancreatitis, retinopathy, nephropathy, neuropathy ( Reichard et al., N. Engl. J. Med. 1993, 329:304-309), a certain type of cancer (Strickler et al., Diabetes Technology & Therapeutics 2001, 3(2):263-274), or glaucoma (Pascale et al., Ophtalmology 2006, 113(7):1081-86). [0002] The present invention also relates to compositions of said compounds and other medicaments for the treatment of the diseases mentioned above. Indeed, treatment of diseases such as type II diabetes often requires a combination of comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/06A61K31/5415
CPCC07D275/06A61P1/18A61P13/12A61P25/00A61P27/02A61P27/06A61P3/00A61P3/04A61P35/00A61P3/06A61P43/00A61P5/50A61P7/12A61P9/00A61P9/10A61P9/12A61P3/10A61K31/5415C07D279/02
Inventor M·佩雷M·拉莫特D·洪克罗Y·里瓦尔
Owner PIERRE FABRE MEDICAMENT SAS
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