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Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof

A technology of pyrazole derivatives and alkyl, applied in the field of pyrazole derivatives, can solve the problems of insufficient absorption of glucose and galactose

Inactive Publication Date: 2005-10-26
KISSEI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Glucose and galactose underabsorption have also been reported in patients with dysfunction due to congenital abnormalities of human SGLT1 (see 6-8 below)

Method used

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  • Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof
  • Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof
  • Pyrazole derivative, medicinal composition containing the same, medicinal use thereof, and intermediate for production thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0303] 4-({4-[3-(carbamoylmethylcarbamoyl)propyl]phenyl}methyl)-3-(β-D-glucopyranose Oxy)-5-isopropyl-1H-pyrazole

[0304] To 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-ene base]phenyl}methyl)-5-isopropyl-1H-pyrazole (0.34g) in N,N-dimethylformamide (1mL) solution, add glycinamide hydrochloride (0.12g ), 1-hydroxybenzotriazole (0.09g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.15g) and triethylamine (0.27g) , and the mixture was stirred overnight at room temperature. Insoluble material was removed by filtration. To the filtrate, 5 mol / L aqueous sodium hydroxide solution (0.5 mL) was added, and the mixture was stirred at room temperature for 1 hr. The insoluble matter was removed by filtration, and then the filtrate was purified by preparative reverse column chromatography (Shiseido CAPCELL PAK UG120 ODS, 5 μm, 120 Å, 20×50 mm, flow rate 30 mL / min linear gradient, water / acetonitrile=90 / 10-10 / 90), giving 4-({4-[(1E)...

Embodiment 2

[0308] 4-{[4-(3-carbamoylpropyl)phenyl]methyl}-3-(β-D-glucopyranosyloxy)-5-isopropyl- 1H-pyrazole

[0309] The title compound was prepared analogously to Example 1, using ammonium chloride instead of glycinamide hydrochloride.

[0310] 1 H-NMR (CD 3 OD)δppm:

[0311] 1.05-1.2(6H, m), 1.8-1.95(2H, m), 2.19(2H, t, J=7.6Hz), 2.58(2H, t, J=7.5Hz), 2.85-2.95(1H, m) , 3.3-3.45(4H, m), 3.6-3.8(3H, m), 3.8-3.9(1H, m), 5.0-5.1(1H, m), 7.0-7.15(4H, m)

Embodiment 3

[0313] 4-({4-[3-(2-carbamoylethylcarbamoyl)propyl]phenyl}methyl)-3-(β-D-glucopyranose (Sugaroxy)-5-isopropyl-1H-pyrazole

[0314] The title compound was prepared analogously to Example 1, substituting 3-aminopropanamide for glycinamide hydrochloride.

[0315] 1 H-NMR (CD 3 OD)δppm:

[0316] 1.05-1.2(6H, m), 1.8-1.95(2H, m), 2.15(2H, t, J=7.3Hz), 2.4(2H, t, J=6.7Hz), 2.56(2H, t, J= 7.5Hz), 2.85-2.95(1H, m), 3.25-3.45(6H, m), 3.6-3.9(4H, m), 5.0-5.1(1H, m), 7.0-7.15(4H, m)

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Abstract

The present invention provides a pyrromonazole derivant shown in the formula (I). In the formula (I), R<1> is H, optional substituent C1-6 alkyl, etc.; one group in Q and T is a group represented by the formula (a) or a group represented by the formula (b), while another group is optional substituent C1-6 alkyl, etc.; X is a single bond, O or S; Y is a single bond, C1-6 alkylidene, etc.; R<3>, R<6> and R<7> are H, halogen atoms, etc.; the present invention also provides a pharmaceutically acceptable salt or a prodrug thereof. Showing excellent inhibitory activity for human SGLT1, the present invention can be used as drugs to prevent or treat hyperglycemia-related diseases (such as, diabetes, diabetic complications or obesity). The present invention also provides a drug compound of the derivants, a pharmic use thereof and an intermediate used for production.

Description

technical field [0001] The present invention relates to pyrazole derivatives which can be used as medicines, their pharmaceutically acceptable salts or their prodrugs, pharmaceutical compositions containing them, their pharmaceutical use and intermediates for their production. [0002] More specifically, the present invention relates to pyrazole derivatives having inhibitory activity in human SGLT1, pharmaceutically acceptable salts thereof or prodrugs thereof, which can be used as drugs to prevent or treat diseases related to hyperglycemia (such as diabetes, glucose intolerance disorder, fasting hyperglycemia disorder, diabetic complications or obesity), and also pharmaceutical compositions containing them, their pharmaceutical use and intermediates for their production. Background technique [0003] Diabetes is one of the lifestyle-related diseases, whose background is a change in eating habits and lack of exercise. Therefore, diet and exercise therapy are implemented in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/02
Inventor 寺西弘孝伏见信彦米漥滋清水和夫柴崎利英伊佐治正幸
Owner KISSEI PHARMA
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