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

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

CN102884047AInactive Publication Date: 2013-01-16NISSAN CHEM IND LTD
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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

Patent Timeline
16 Jan 2013
Publication
CN102884047A
IPC
C07D213/64; A61K31/4412; A61K31/4427; A61K31/443; A61K31/4433; A61K31/4439; A61K31/444; A61K31/4545; A61K31/496; A61K31/5377; A61P3/00; A61P3/04; A61P3/06; A61P3/10; A61P7/10; A61P9/10; A61P19/06; A61P25/00; A61P27/02; A61P43/00; C07D401/10; C07D401/12; C07D405/10
CPC
C07D401/14; C07D417/06; C07D401/12; C07D417/14; C07D405/10; C07D401/10; C07D213/64; C07D413/06
Inventors
河口尚则; 绵谷宪吾