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Amide derivatives as GK activators

A compound and substituent technology, applied in the field of amide derivatives as GK activators, can solve the problem that weight loss is not a therapeutic target

Inactive Publication Date: 2009-07-01
NOVO NORDISK AS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, initial weight loss is not a preferred treatment goal

Method used

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  • Amide derivatives as GK activators

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0523] 2-(3,4-Dichlorophenoxy)-hexanoic acid thiazol-2-ylamide

[0524]

[0525] 2-(3,4-Dichlorophenoxy)hexyl was prepared from ethyl 2-hydroxyhexanoate (0.32 g, 2.0 mmol) and 3,4-dichlorophenol (0.39 g, 2.4 mmol) according to general procedure A Acid (0.3 g, 55%). A solution of this acid (69 mg, 0.25 mmol) in THF (3 ml) was reacted with 2-aminothiazole (60 mg, 0.6 mmol) according to general procedure E to give 2-(3,4-dichlorophenoxy)-hexyl Acid thiazol-2-ylamide (64 mg, 72%).

[0526] LCMS(m / z): 360(M+H) +

[0527] 1 H NMR (400MHz, CDCl 3 ): δ 0.89(t, 3H), 1.30-1.51(m, 4H), 2.02(m, 2H), 4.73(t, 1H), 6.76(dd, 1H), 7.03(dd, 2H), 7.33(d , 1H), 7.49(d, 1H), 9.98(br, 1H).

Embodiment 2

[0529] 2-(4-fluorophenoxy)-N-1,3-thiazol-2-ylhexanamide

[0530]

[0531] 2-(4-Fluorophenoxy)hexanoic acid (0.23 g, 52 %). A solution of this acid (56 mg, 0.25 mmol) in THF (3 ml) was reacted with 2-aminothiazole (60 mg, 0.6 mmol) following general procedure E to afford 2-(4-fluorophenoxy)-N-1, 3-Thiazol-2-ylhexanamide (58 mg, 76%).

[0532] LCMS (m / z): 309 (M+H) +

[0533] 1 H NMR (400MHz, CDCl 3): δ 0.89(t, 3H), 1.32-1.50(m, 4H), 1.99(m, 2H), 4.69(t, 1H), 6.81-6.84(m, 2H), 6.94-7.02(m, 3H) , 7.50(d, 1H), 10.24(br, 1H).

Embodiment 3

[0535] 2-(4-Methoxyphenoxy)-N-1,3-thiazol-2-ylhexanamide

[0536]

[0537] 2-(4-Methoxyphenoxy)hexanoic acid ( 0.23 g, 48%). A solution of this acid (60 mg, 0.25) in THF (3 ml) was reacted with 2-aminothiazole (60 mg, 0.6 mmol) via Method E to afford 2-(4-methoxyphenoxy)-N-1 , 3-thiazol-2-ylhexanamide (130 mg, 82%).

[0538] LCMS (m / z): 321 (M+H) +

[0539] 1 H NMR (400MHz, CDCl 3 ): δ0.89(t, 3H), 1.31-1.52(m, 4H), 1.98(m, 2H), 3.74(s, 3H), 4.67(t, 1H), 6.82(m, 4H), 7.01( d, 1H), 7.52 (d, 1H), 10.33 (br, 1H).

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Abstract

The present invention relates to compounds of general formula (I), which are activators of glucokinase (GK), and which may be suitable for the treatment, treatment, control and auxiliary treatment of such diseases: wherein increasing the activity of glucokinase is Beneficial, such as IGT, syndrome X, type 2 diabetes, type 1 diabetes, dyslipidemia, hyperlipidemia, hypertension and obesity.

Description

field of invention [0001] The present invention relates to compounds, which are activators of glucokinase (GK), which may be suitable for the treatment, management, management or adjunctive treatment of such diseases, in which case glucose Kinase activity is beneficial. Background of the invention [0002] Diabetes is characterized in that impaired glucose metabolism in diabetic patients proves itself to be caused by elevated blood glucose levels. The underlying defect causes diabetes to fall into two main categories: type 1 diabetes, or insulin-dependent diabetes mellitus (IDDM), which results when a patient lacks the insulin-producing beta cells in their pancreas; and type 2 diabetes, or non-insulin-dependent diabetes (NIDDM), which occurs in patients when impaired beta cell function occurs in addition to a cluster of other abnormalities. [0003] Patients with type 1 diabetes are currently treated with insulin, while most patients with type 2 diabetes are treated with s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/46A61K31/4402A61K31/505A61P3/04A61P3/10C07D417/12C07D213/75C07D409/12C07D239/42C07D405/12A61K31/426A61K31/16A61K31/18A61K31/427A61K31/433A61K45/00A61K45/06A61P3/06A61P5/50A61P9/12A61P43/00C07D277/20C07D277/44C07D277/48C07D285/135
CPCA61K31/16A61K31/18C07D277/46C07D213/75A61K45/06A61P1/00A61P1/18A61P3/00A61P3/10A61P3/04A61P3/06A61P43/00A61P5/50A61P9/00A61P9/10A61P9/12A61K31/426A61K31/4402
Inventor J·劳J·T·科德拉M·古泽尔K·C·桑托什A·M·M·米加里R·C·安德鲁斯D·R·波里塞蒂
Owner NOVO NORDISK AS
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