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2-pyridone compounds

A compound and pyridone technology, applied in the field of novel 2-pyridone compounds, can solve problems such as reducing GK activity

Inactive Publication Date: 2013-01-16
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mutations in these genes have been shown to reduce GK activity

Method used

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  • 2-pyridone compounds
  • 2-pyridone compounds
  • 2-pyridone compounds

Examples

Experimental program
Comparison scheme
Effect test

reference example 1-2

[0818] (5-Chloro-6-methoxypyridin-2-yl)[4-(cyclopropylsulfanyl)phenyl]methanone

[0819] 1 H NMR (300MHz, CDCl 3 )δppm 0.61-0.83(m, 2H), 1.07-1.22(m, 2H), 2.23(tt, J=7.3, 4.4Hz, 1H), 4.02(s, 3H), 7.43(d, J=8.7Hz, 2H), 7.63(d, J=7.8Hz, 1H), 7.82(d, J=7.9Hz, 1H), 8.09(d, J=8.7Hz, 2H).

[0820] MS(+): 342 [M+Na] + .

reference example 1-3

[0822] (5-Chloro-6-methoxypyridin-2-yl)[4-(cyclopentylsulfanyl)phenyl]methanone

[0823] 1 H NMR (300MHz, CDCl 3 )δppm 1.58-1.74 (m, 4H), 1.75-1.91 (m, 2H), 2.08-2.30 (m, 2H), 3.61-3.85 (m, 1H), 4.02 (s, 3H), 7.34 (d, J =8.7Hz, 2H), 7.63(d, J=7.8Hz, 1H), 7.81(d, J=7.8Hz, 1H), 8.07(d, J=8.7Hz, 2H).

[0824] MS(+): 348[M+H] + .

[0825] Reference example 1-4

[0826] [3-Chloro-4-(ethylsulfanyl)phenyl](5-chloro-6-methoxypyridin-2-yl)methanone

[0827] 1 H NMR (300MHz, CDCl 3 )δppm 1.45(t, J=7.4Hz, 3H), 3.06(q, J=7.3Hz, 2H), 4.04(s, 3H), 7.27(d, J=8.4Hz, 1H), 7.68(d, J =7.8Hz, 1H), 7.83(d, J=7.9Hz, 1H), 8.04(dd, J=8.4, 1.9Hz, 1H), 8.31(d, J=1.9Hz, 1H).

[0828] Reference example 1-5

[0829] (5-Chloro-6-methoxypyridin-2-yl)[3-(cyclopropylsulfanyl)phenyl]methanone

[0830] 1 H NMR (300MHz, CDCl 3 )δppm 0.68-0.75(m, 2H), 1.06-1.14(m, 2H), 2.17-2.27(m, 1H), 4.01(s, 3H), 7.35-7.43(m, 1H), 7.56-7.61(m , 1H), 7.65(d, J=7.8Hz, 1H), 7.82(d, J=7.8Hz, 1H), 7.86(dt, J=7.7, 1.3H...

reference example 1-10

[0849] (5-Chloro-6-methoxypyridin-2-yl){4-[(3-methylbutoxy)methyl]phenyl}methanone

[0850] 1 H NMR (300MHz, CDCl 3 )δppm 0.92(d, J=6.6Hz, 6H), 1.50-1.60(m, 2H), 1.67-1.84(m, 1H), 3.54(t, J=6.7Hz, 2H), 4.00(s, 3H) , 4.58(s, 2H), 7.44(d, J=8.3Hz, 2H), 7.64(d, J=7.7Hz, 1H), 7.81(d, J=7.7Hz, 1H), 8.10(d, J=7.7Hz, 1H), 8.10(d, J=7.7Hz, 1H) 8.0Hz, 2H).

[0851] MS(+): 348[M+H] + .

[0852] Reference example 1-11

[0853] (5-Chloro-6-methoxypyridin-2-yl)[4-(propan-2-yl)phenyl]methanone

[0854] 1 H NMR (300MHz, CDCl 3 )δppm 1.29(s, 3H), 1.31(s, 3H), 2.92-3.06(m, 1H), 4.03(s, 3H), 7.33(d, J=8.4Hz, 2H), 7.61(d, J= 7.8Hz, 1H), 7.80(d, J=7.8Hz, 1H), 8.09(d, J=8.7Hz, 2H).

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Abstract

2-Pyridone compounds represented by general formula [1], tautomers or stereoisomer thereof, pharmaceutically acceptable salts of the same, or solvates thereof have excellent GK-activating activity and therefore are useful as drugs. In general formula [1], A is a benzene ring or a pyridine ring; X is a structure represented by general formula [3]; V is a single bond or lower alkylene; W is a single bond, an ether linkage, or lower alkylene (which may contain an ether linkage).

Description

technical field [0001] The present invention relates to novel 2-pyridone compounds having glucokinase activating effect, and to pharmaceuticals comprising the compounds as active ingredients. Background technique [0002] Glucokinase (hereinafter referred to as GK) belongs to the hexokinase family, and catalyzes the phosphorylation of glucose taken up into cells such as pancreatic β cells or hepatocytes. GK in the liver and GK in pancreatic β cells differ from each other in the sequence of the N-terminal 15 amino acids due to differences in splicing, but are identical enzymatically. GK has a high affinity for glucose, S 0.5 is about 10 mM and is not inhibited by the product, glucose 6-phosphate. Therefore, its reaction rate responds sensitively to physiological changes in blood glucose levels. GK in pancreatic β-cells regulates glucose-dependent insulin secretion, while GK in the liver regulates the glycolytic pathway or glycogenogenesis so that blood glucose levels are m...

Claims

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Application Information

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IPC IPC(8): C07D213/64A61K31/4412A61K31/4427A61K31/443A61K31/4433A61K31/4439A61K31/444A61K31/4545A61K31/496A61K31/5377A61P3/00A61P3/04A61P3/06A61P3/10A61P7/10A61P9/10A61P19/06A61P25/00A61P27/02A61P43/00C07D401/10C07D401/12C07D405/10
CPCC07D401/14C07D417/06C07D401/12C07D417/14C07D405/10C07D401/10C07D213/64C07D413/06A61P13/12A61P19/06A61P25/00A61P27/02A61P3/00A61P3/04A61P31/00A61P3/06A61P43/00A61P7/10A61P9/10A61P3/10C07D213/643
Inventor 河口尚则绵谷宪吾伏木启子坊野匡宏浅沼肇黑田翔一今井佑大长南具通佐藤长明鸨田滋笹子滋正冈田匠林圭史伊藤晋齐藤宪子地曳瑠衣石山圣志太田博史
Owner NISSAN CHEM IND LTD
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