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Carbazole derivative, solvate thereof, or pharmaceutically acceptable salt thereof

A technology of carbazole derivatives and solvates, which can be used in drug combinations, antipyretics, anti-inflammatory agents, etc., can solve the problems of reduced expression levels and promotion of obesity, and achieve excellent PPARγ inhibitory activity

Inactive Publication Date: 2007-10-03
ZERIA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, TZD derivatives are useful as therapeutic agents for diabetes, but there is a risk that they may promote obesity
In addition, it has also been reported that leptin (leptin) is a known anti-obesity factor, and if TZD derivatives are given, the expression level of leptin is reduced (J.Biol, Chem., (1996), 271, 9455-9459 (non- Patent Document 5))

Method used

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  • Carbazole derivative, solvate thereof, or pharmaceutically acceptable salt thereof
  • Carbazole derivative, solvate thereof, or pharmaceutically acceptable salt thereof
  • Carbazole derivative, solvate thereof, or pharmaceutically acceptable salt thereof

Examples

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preparation example Construction

[0347] (2. The preparation method of the compound of the present invention)

[0348] The compound of the present invention represented by the general formula (I) can be produced, for example, according to the following A method and B method.

[0349] (2.1. The preparation method of the compound of the present invention-A method-)

[0350] An example of the method (Method A) for producing the compound of the present invention represented by the general formula (I) is described below. Method A is a method including the steps shown in the following process chart.

[0351]

[0352] In the above formula, A, V, W, X, Y, Z, a, b, R 1 , R 2 and R 3 means the same meaning as defined above. E represents a leaving group. Examples of E include hydroxyl, halogen, -OSO 2 R 7 (R 7 Methyl, trifluoromethyl, phenyl, tolyl or nitrophenyl may be mentioned. More specific examples of E include a chlorine atom or a bromine atom.

[0353] As described above, method A is a method for syn...

reference example 1

[0467] Synthesis of 4-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-5-methyl-2-phenyloxazole

[0468]

[0469] Reference example 1(a)

[0470] Synthesis of 4,5-Dimethyl-2-phenyloxazole N-oxide

[0471]

[0472] 500 g of benzaldehyde and 476 g of diacetyl-methoxyme were suspended in 1 L of acetic acid, and ice-cooled. Hydrogen chloride gas was slowly bubbled in at an internal temperature of 7°C to make it saturated. Stir overnight at room temperature. The reaction solution was poured into 1.5 kg of ice, and neutralized with a 25% aqueous sodium hydroxide solution. The precipitated crystals were filtered off, and washed successively with 1 L of water and 1 L of diisopropyl ether. The obtained substance was dissolved in 3 L of chloroform, and the insoluble matter was filtered off. The filtrate was dried over 200 g of anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. 3 L of IPE was added to the residue to crystallize it, and th...

reference example 2

[0490] Synthesis of 4-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-2-(furan-2-yl)-5-methyloxazole

[0491]

[0492] Using furfural instead of benzaldehyde used in Reference Example 1(a), the same operations as in Reference Examples 1(a) to 1(d) were carried out to obtain the title compound.

[0493] 1 H-NMR (400MHz, DMSO-d 6 )δppm: 2.41 (3H, s) 3.76 (3H, s) 4.72 (2H, d) 4.97 (2H, s) 6.71 (1H, dd) 6.98 (1H, dd) 6.71 (1H, dd) 6.98 (1H, dd )7.06(1H,d)7.08(1H,d)7.11(1H,dd)7.91(1H,dd)

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Abstract

A novel carbazole derivative which has the excellent functions of reducing the weight of fat tissues and lowering the blood sugar level and the blood lipid level. It is useful as a preventive / therapeutic agent for fatty liver, obesity, lipid metabolism abnormality, visceral fat, diabetes, hyperlipemia, impaired glucose tolerance, hypertension, non-alcoholic fatty liver, or non-alcoholic steatohepatitis. It is a carbazole derivative represented by the following general formula (I). (In the formula (I), ring A represents phenyl, etc.; X represents -O-, etc.; Y represents =N-, etc.; a and b each represents methylene, etc.; V and Z each represents -O-, etc.; W represents C1-10 alkylene in which one or two hydrogen atoms may be replaced with phenyl or C1-5 alkyl, or represents 1,2-phenylene, 1,3-cyclohexyl, etc.; R<1> represents methyl, etc.; R<2> represents methoxy, etc.; and R<3> represents carboxy, etc.

Description

technical field [0001] The present invention relates to carbazole derivatives, their solvates or pharmaceutically acceptable salts thereof, pharmaceutical compositions and medicines containing the above-mentioned compounds, and the like. More specifically, the present invention relates to a novel carbazole derivative, its solvate or pharmaceutically acceptable salt, etc., which have excellent effects of reducing adipose tissue weight, hypoglycemic effect and hypolipidemic effect. , obesity, dyslipidemia, visceral fat, diabetes, hyperlipidemia, impaired glucose tolerance, hypertension, nonalcoholic fatty liver and nonalcoholic steatohepatitis, etc. . Background technique [0002] In recent years, lifestyle-related diseases such as obesity and diabetes have gradually become problems. Therefore, attention has been paid to transcription factors involved in induction of expression of adipocyte differentiation marker genes. Peroxisome Proliferator Activated Receptor (hereinafte...

Claims

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Application Information

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IPC IPC(8): C07D413/12C07D413/14C07D417/12A61K31/422A61K31/427A61K31/4439A61P1/16A61P3/04A61P3/06A61P3/10A61P9/12A61P43/00
CPCC07D413/12C07D413/14C07D417/12A61P1/00A61P1/16A61P29/00A61P3/00A61P3/10A61P3/04A61P3/06A61P43/00A61P9/00A61P9/12A61K31/422A61K31/427
Inventor 村田正和丝数义彦中尾龙
Owner ZERIA PHARMA
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