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Azetidinone derivatives and methods of use thereof

A technology of action and compound, applied in the field of azetidinone derivatives and its use, can solve problems such as hypoglycemia

Inactive Publication Date: 2009-09-09
SCHERING AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Oral antihyperglycemic agents of the sulfonylurea class stimulate insulin secretion from pancreatic β-islet cells, but have the potential to cause hypoglycemia because their action is independent of the amount of glucose

Method used

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  • Azetidinone derivatives and methods of use thereof
  • Azetidinone derivatives and methods of use thereof
  • Azetidinone derivatives and methods of use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0345] Preparation of intermediate compound IA-1

[0346] The synthesis of compound IA-1, which is useful as an intermediate for the preparation of azetidinone derivatives of formula (IA), is described below:

[0347]

[0348] IA-1

[0349] A first solution of LiHMDS (2.8 mol) in THF (1.0 L) was cooled to -30°C, and benzaldehyde (300 g, 2.8 mol) was added dropwise to the resulting mixture with stirring. In another bottle, a second solution of LDA (2.8 mol in THF) was cooled to -78°C and BOC-ethylisopiperidate (687 g, 2.8 mol) in THF (500 mL) was added dropwise The solution. The first solution was then added dropwise to the second solution with stirring at a rate such that the reaction temperature remained below 0°C throughout the addition. The resulting reaction was then allowed to stir at 0°C for about 3 hours before being carefully quenched with water (1 L). The resulting solution was extracted with ethyl acetate (5 L) and transferred to a separatory funnel. The orga...

Embodiment 2

[0351] Preparation of intermediate compound IB-1

[0352] The synthesis of compound IB-1, which is useful as an intermediate for the preparation of azetidinone derivatives of formula (IB), is described below:

[0353]

[0354] IB-1

[0355] Using the method described in Example 1, substituting 4-chlorobenzaldehyde for benzaldehyde, compound IB-1 was prepared. 1 H NMR (300MHz, CDCl 3 )δ7.4(d, 2H), 7.2(t, 3H), 4.5(s, 1H), 3.8(br, 1H), 3.6(t, 1H), 3.3(br, 2H), 2.1(br, 1H ), 1.9 (br, 1H), 1.4 (s, 9H), 1.2 (br, 1H).

Embodiment 3

[0357] Preparation of intermediate compound IC-1

[0358] The synthesis of compound IC-1, which is useful as an intermediate for the preparation of azetidinone derivatives of formula (IC), is described below:

[0359]

[0360] IC-1

[0361] Using the method described in Example 1, substituting pyridine-3-carbaldehyde for benzaldehyde, compound IC-1 was prepared. 1 H NMR (300MHz, CDCl 3 )δ8.2(d, 2H), 7.3(d, 1H), 7.0(m, 1H), 4.2(s, 1H), 3.3(br, 1H), 3.2(t, 1H), 3.1(br, 1H ), 3.0 (br, 1H), 1.9 (d, 1H), 1.6 (t, 1H), 1.1 (s, 10H), 0.8 (m, 1H).

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Abstract

The present invention relates to methods for treating or preventing a disorder of lipid metabolism, pain, diabetes, a vascular condition, demyelination or nonalcoholic fatty liver disease, comprising administering a compound having the formula (I) or a pharmaceutically acceptable salt, solvate, ester, prodrug or stereoisomer thereof, wherein: R and R are defined in Tables 1-6 herein, and R3 is -phenyl, -4-chlorophenyl, -2-pyridyl, or -3-pyridyl.

Description

[0001] Citing an earlier application [0002] This application claims priority to US Provisional Patent Application No. 60 / 844,808, filed September 15, 2006, which is hereby incorporated by reference in its entirety. field of invention [0003] The present invention relates to a method of treating or preventing lipid metabolism disorders, pain, diabetes, vascular disorders, demyelination or nonalcoholic fatty liver disease, the method comprising administering a compound of the formula: [0004] [0005] (I) [0006] or a pharmaceutically acceptable salt, solvate, ester, prodrug or stereoisomer thereof, wherein [0007] R 1 and R 2 are defined in Tables 1-6 herein, and [0008] R 3 is -phenyl, -4-chlorophenyl, -2-pyridyl or -3-pyridyl. Background technique [0009] The treatment of chronic pain, especially inflammation and neuropathic pain, is an area that does not yet meet medical needs. Neuralgia is a nerve injury that results in excessive activation of neurons i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4427A61P3/06A61P3/10A61P9/10A61P25/28C07D401/04
CPCC07D519/00A61K31/4427C07D471/10A61P1/02A61P1/04A61P1/08A61P1/12A61P1/14A61P1/16A61P3/00A61P3/06A61P3/10A61P9/00A61P9/10A61P11/00A61P11/06A61P11/14A61P13/00A61P13/02A61P13/10A61P15/00A61P17/00A61P17/02A61P17/04A61P17/06A61P17/14A61P21/00A61P25/00A61P25/04A61P25/08A61P25/28A61P27/02A61P29/00A61P29/02A61P31/18A61P43/00
Inventor R·G·亚斯兰安詹亭月J·M·哈里斯B·A·麦基崔克B·R·纽斯塔特A·帕拉尼T·普利斯莱E·M·史密斯A·W·史丹佛H·M·斐卡洛萧彤
Owner SCHERING AG
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