Unlock instant, AI-driven research and patent intelligence for your innovation.

Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof

a technology of glucopyranosyloxypyrazole and derivatives, which is applied in the field of glucopyranosyloxypyrazole derivatives, can solve the problems of control and continuous performance, and the occasional adverse effects of biguanides and sulfonylureas

Inactive Publication Date: 2005-06-23
KISSEI PHARMA
View PDF3 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to new glucopyranosyloxypyrazole derivatives and pharmaceutical compositions containing them. These compounds have potential hypoglycemic and hypolipidemic effects, which make them useful in the treatment of diabetes and related metabolic disorders. The invention also includes new methods for making these compounds.

Problems solved by technology

Furthermore, when its sufficient control and continuous performance are difficult, drug treatment is simultaneously performed.
However, biguanides and sulfonylureas show occasionally adverse effects such as lactic acidosis and hypoglysemia, respectively.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof
  • Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof
  • Glucopyranosyloxypyrazole derivatives, medicinal compositions containing the same and intermediates in the production thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

1,2-Dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one

[0033] To a solution of 4-isopropoxybenzylalcohol (0.34 g) in tetrahydrofuran (6 mL) were added triethylamine (0.28 mL) and methanesulfonyl chloride (0.16 mL), and the mixture was stirred at room temperature for 30 minutes. The resulting insoluble material was removed by filtration. The obtained solution of 4-isopropoxybenzyl methanesulfonate in tetrahydrofuran was added to a suspension of sodium hydride (60%, 81 mg) and methyl acetoacetate (0.20 mL) in 1,2-dimethoxyethane (10 mL), and the mixture was stirred at 80° C. overnight. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in toluene (5 mL). Anhydrous hydrazine (0.19 mL) was added to the solution, a...

example 2

1,2-Dihydro-5-methyl-4-[(4-propylphenyl)methyl]-3H-pyrazol-3-one

[0036] The title compound was prepared in a similar manner to that described in Example 1 using 4-propylbenzyl alcohol instead of 4-isopropoxybenzyl alcohol.

[0037]1H-NMR (500 MHz, DMSO-d6) δ ppm:

[0038] 0.75-0.95 (3H, m), 1.45-1.65 (2H, m), 1.99 (3H, s), 2.40-2.55 (2H, m), 3.32 (2H, s), 6.95-7.10 (4H, m)

example 3

1,2-Dihydro-4-[(4-isobutylphenyl)methyl]-5-methyl-3H-pyrazol-3-one

[0039] The title compound was prepared in a similar manner to that described in Example 1 using 4-isobutylbenzyl alcohol instead of 4-isopropoxybenzyl alcohol.

[0040]1H-NMR (500 MHz, DMSO-d6) δ ppm:

[0041] 0.83 (6H, d, J=6.6 Hz), 1.70-1.85 (1H, m), 1.99 (3H, s), 2.30-2.45 (2H, m), 3.50 (2H, s), 6.90-7.10 (4H, m)

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
temperatureaaaaaaaaaa
pHaaaaaaaaaa
concentrationaaaaaaaaaa
Login to View More

Abstract

The present invention relates to glucopyranosyloxypyrazole derivatives represented by the general formula: wherein R1 represents a hydrogen atom or a lower alkyl group; one of Q1 and T1 represents a group represented by the general formula: while the other represents a lower alkyl group or a halo(lower alkyl) group; and R2 represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a halo(lower alkyl) group or a halogen atom, or pharmaceutically acceptable salts thereof, which have an inhibitory activity in human SGLT2 and are useful as agents for the prevention or treatment of diabetes, diabetic complications or obesity, and to pharmaceutical compositions comprising the same and intermediates thereof.

Description

TECHNICAL FIELD [0001] The present invention relates to glucopyranosyloxypyrazole derivatives or pharmaceutically acceptable salts thereof, which are useful as medicaments, pharmaceutical compositions comprising the same and intermediates thereof. BACKGROUND ART [0002] Diabetes is one of lifestyle-related diseases with the background of change of eating habit and lack of exercise. Hence, diet and exercise therapies are performed in patients with diabetes. Furthermore, when its sufficient control and continuous performance are difficult, drug treatment is simultaneously performed. Now, biguanides, sulfonylureas and insulin sensitivity enhancers have been employed as antidiabetic agents. However, biguanides and sulfonylureas show occasionally adverse effects such as lactic acidosis and hypoglysemia, respectively. In a case of using insulin sensitivity enhancers, adverse effects such as edema occasionally are observed, and it is also concerned for advancing obesity. Therefore, in order...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/7056A61P3/04A61P3/10C07D231/20C07H17/02
CPCC07D231/20Y10S514/909Y10S514/866C07H17/02A61P3/00A61P3/10A61P3/04A61P43/00A61K31/7056
Inventor FUJIKURA, HIDEKINISHIMURA, TOSHIHIROKATSUNO, KENJIHIRATOCHI, MASAHIROIYOBE, AKIRAFUJIOKA, MINORUISAJI, MASAYUKI
Owner KISSEI PHARMA