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Pyrazole compounds and antidiabetes agents containing the same

A diabetes and compound technology, applied in the field of new pyrazole compounds, can solve problems such as unsatisfactory oral absorption and metabolic stability, and unsatisfactory activity

Inactive Publication Date: 2008-06-25
JAPAN TOBACCO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the requirements have not been met in terms of activity
In addition, it is not satisfactory in terms of oral absorption and metabolic stability

Method used

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  • Pyrazole compounds and antidiabetes agents containing the same
  • Pyrazole compounds and antidiabetes agents containing the same
  • Pyrazole compounds and antidiabetes agents containing the same

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[2607] The production process scheme below is an example of a typical production method, but the production method of the present invention is not particularly limited to the following method. The compounds obtained in each step can be isolated and purified by conventional methods, but sometimes the next step can be carried out without isolation and purification.

[2608] Preparation method A (preparation methods A-1 to A-3):

[2609] Preparation method A is shown below. Each symbol in the reaction formula has the same meaning as above. The following are the same.

[2610]

[2611] Step 1; Preparation of Compound (A2)

[2612] The compound (A2) can be obtained by reducing the nitro group of the compound (A1) to an amino group with hydrogen in a solvent in the presence of a catalyst.

[2613]

[2614] As the solvent used in the reaction, for example, alcohol solvents such as methanol and ethanol; ether solvents such as dioxane and tetrahydrofuran; ester solvents su...

Embodiment

[2723] Hereinafter, the present invention will be described in detail by citing examples, but the present invention is not limited by these examples.

reference example 1

[2724] Reference Example 1: 5-(2-chloro-4,5-difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid imidazolide and 5-(2-chloro-4,5-difluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid (benzene Preparation of triazol-1-yl)-ester;

[2725] (operation 1) preparation of 2-chloro-4,5-difluorobenzoyl chloride;

[2726]

[2727]In 2-chloro-4,5-difluorobenzoic acid (508.20g) in toluene (250ml) solution, add N,N-dimethylformamide (0.2ml), after heating to 65°C, add sulfite dropwise Acid chloride (230ml). After stirring at 120°C for 3 hours, the reaction solution was concentrated under reduced pressure, and the resulting residue was distilled under reduced pressure (bp 51-64°C (130-140Pa)) to obtain the title compound (534.45 g) as an oil.

[2728] (operation 2) preparation of ethyl 5-nitro-3-pyrazolecarboxylate;

[2729]

[2730] Methanesulfonic acid (143 ml) was added to a solution of 5-nitro-3-pyrazolecarboxylic acid (310.24 g) in ethanol (3 L), followed by stirring a...

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PUM

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Abstract

A pyrazole compound represented by the general formula (I) or a salt thereof which has a hepatic glycogen phosphorylase inhibitory activity and therefore is useful as a therapeutic or prophylactic agent for diabetes or a pharmacologically salt thereof : wherein the ring Q represents an aryl group or an aromatic heterocyclic group; R<1> represents a hydrogen atom, a halogen atom, a C1-6 alkyl group or a C1-6 alkoxy group; R<2> represents a halogen atom, a C1-6 alkyl group, a C1-6 alkoxy group or an azide group; R<3> represents a halogen atom, a hydroxyl group, a C1-6 alkyl group, a halo-C1-6 alkyl group, a C1-6 alkoxy group, an azide group, an amino group, an acylamino group or a C1-6 alkylsulfonylamino group; R<4> and R<5> independently represent a hydrogen atom, a C1-6 alkyl group which may be substituted, a a C3-8 cycloalkyl group, a saturated heterocyclic group which may be substituted, an aryl group which may be substituted, a C7-14 aralkyl group, an aromatic heterocyclic group or the like.

Description

technical field [0001] The present invention relates to a pharmaceutical composition for treating or preventing diabetes comprising a pyrazole compound having liver glycogen phosphorylase inhibitory activity and a pharmaceutically acceptable carrier, and a novel pyrazole compound having liver glycogen phosphorylase inhibitory activity Azole compounds, and pharmaceutical compositions for the treatment or prevention of diabetes and other medicaments (for example, therapeutic agents for hyperlipidemia, therapeutic or preventive agents for obesity, therapeutic agents for diabetes, therapeutic agents for diabetic complications, hypertension, etc.) Therapeutic agents) are combined to form a pharmaceutical composition. Background technique [0002] Diabetes is a chronic disease caused by abnormal metabolism of sugar (glucose), lipids, and amino acids due to lack of insulin action. Hyperglycemia and glycosuria will appear in the case of continuous untreatment. [0003] Diabetes is...

Claims

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Application Information

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IPC IPC(8): C07D231/40A61K31/41A61K31/415A61K31/4155A61K31/4184A61K31/4192A61K31/4196A61K31/422A61K31/4245A61K31/427A61K31/428A61K31/433A61K31/4439A61K31/444A61K31/4453A61K31/454A61K31/455A61K31/47A61K31/4709A61K31/4725
Inventor 高木正树中村健松田勇福田贤治小泽浩一上田顺久坂田薰野村幸广
Owner JAPAN TOBACCO INC
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