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Therapeutic or prophylactic agent for diabetes, obesity, dyslipidemia or metabolic syndrome comprising benzylamine derivative or pharmaceutically acceptable acid addition salt thereof

An acid addition salt, benzylamine technology, used in diabetes, dyslipidemia or metabolic syndrome therapeutic or preventive agent, obesity field, can solve unknown usefulness and other problems, achieve significant therapeutic effect or prevention effect of effect

Inactive Publication Date: 2013-04-24
TORAY IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the usefulness of these compounds for diabetes, obesity, dyslipidemia or metabolic syndrome is unknown

Method used

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  • Therapeutic or prophylactic agent for diabetes, obesity, dyslipidemia or metabolic syndrome comprising benzylamine derivative or pharmaceutically acceptable acid addition salt thereof
  • Therapeutic or prophylactic agent for diabetes, obesity, dyslipidemia or metabolic syndrome comprising benzylamine derivative or pharmaceutically acceptable acid addition salt thereof
  • Therapeutic or prophylactic agent for diabetes, obesity, dyslipidemia or metabolic syndrome comprising benzylamine derivative or pharmaceutically acceptable acid addition salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0111] Hereinafter, the present invention will be described concretely with reference to examples.

reference example 1

[0113] N-(5-((1R,2S)-2-amino-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide (3):

[0114] [chemical formula 6]

[0115]

[0116] Add 10% palladium / carbon (60mg) to the methanol solution (6mL) of the amine derivative (2) (195mg, 0.556mmol) synthesized according to the method described in WO2005 / 040093 Reference Example 1, under hydrogen atmosphere, at room temperature Stir for 2.5 hours. The reaction mixture was filtered, and the filtrate was concentrated to give the title amine (3) (153 mg) as a brown solid. The target amine (3) was used in the subsequent reaction without purification.

[0117] 1 H NMR (400MHz, CD 3 OD) δ (ppm): 1.15 (d, J = 6.8Hz, 3H), 2.97 (s, 3H), 3.46 (m, 1H), 4.85 (d, J = 3.4Hz, 1H), 6.95 (d, J =8.3Hz, 1H), 7.14(dd, J=2.2, 8.3Hz, 1H), 7.40(d, J=2.2Hz, 1H)

Embodiment 1

[0119] N-(5-((1R,2S)-2-(3,5-dimethoxybenzylamino)-1-hydroxypropyl)-2-hydroxyphenyl)methanesulfonamide (4):

[0120] [chemical formula 7]

[0121]

[0122] In methanol solution (10 mL) of amine (3) (363 mg, 1.39 mmol), 3,5-dimethoxybenzaldehyde (301 mg, 1.81 mmol), borane-pyridine complex (445 μL , 4.18mmol), stirred for 2 hours. The reaction mixture was cooled to room temperature, and after adding water, it was extracted with a mixed solvent (ethyl acetate:methanol=10:1), and the organic layer was washed with saturated brine. After the organic layer was dried and concentrated, the resulting crude product was purified by amine silica gel column chromatography (eluent; chloroform:methanol=7:1) to obtain the target amine (4) (329mg, yield: 57%).

[0123] 1 H NMR (400MHz, CD 3 OD) δ (ppm): 1.11 (d, J = 6.4Hz, 3H), 2.83 (m, 1H), 2.89 (s, 3H), 3.61 (d, J = 13.2Hz, 1H), 3.73 (d, J =13.2Hz, 1H), 3.73(s, 6H), 4.48(d, J=6.0Hz, 1H), 6.34(t, J=2.4Hz, 1H), 6.37(d, J=2.4Hz, 2H), 6...

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Abstract

Disclosed is a therapeutic or prophylactic agent for diabetes, obesity, dyslipidemia or metabolic syndrome, which can exhibit significant efficacy at a low dose and does not produce a heart rate increasing activity or a QT interval extending activity which is an adverse side effect on the circulatory system. Specifically disclosed is a therapeutic or prophylactic agent for diabetes, obesity, dyslipidemia or metabolic syndrome, which comprises a benzylamine derivative represented by formula or a pharmaceutically acceptable acid addition salt thereof.

Description

technical field [0001] The present invention relates to a therapeutic or preventive agent for diabetes, obesity, dyslipidemia or metabolic syndrome comprising a benzylamine derivative or a pharmaceutically acceptable acid addition salt thereof. Background technique [0002] Diabetes is a chronic disease resulting from metabolic abnormality showing a chronic hyperglycemic state due to insufficient insulin action. Diabetes is divided into type 1 diabetes characterized by poor insulin secretion, and type 2 diabetes characterized by decreased insulin secretion and decreased sensitivity (insulin resistance). Among them, type 2 diabetes accounts for 90 to 95% of diagnosed diabetes, and is closely related to lifestyle diseases that afflict modern people such as obesity, hypertension, hyperlipidemia, and metabolic syndrome. [0003] Sulfonylureas, phenylalanine derivatives, α-glucosidase inhibitors, biguanides, thiazolidine derivatives, etc. Side effects such as dysfunction and la...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/18A61P3/04A61P3/06A61P3/10
CPCA61K31/18A61P3/00A61P3/04A61P3/06A61P3/10
Inventor 长谷部光吉川悟小园秀树冈崎诚二
Owner TORAY IND INC