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PPAR-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases

An obesity, alkyl technology for use in the field of treatment and/or prevention of obesity or other metabolic disorders

Inactive Publication Date: 2013-02-06
METABOLIC SOLUTIONS DEVMENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compounds associated with PPARγ activation also trigger sodium reabsorption and other undesirable side effects

Method used

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  • PPAR-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases
  • PPAR-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases
  • PPAR-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0466] Example 1: 5-[4-(2-oxo-2-phenylethoxy)benzyl]-1,3-thiazolidine-2,4-dione

[0467]

[0468] step 1: Preparation of 4-(2-hydroxy-2-phenylethoxy)benzaldehyde

[0469] To 2-(4-fluorophenyl)oxirane (6.50 g, 54.0 mmol) was added toluene (85 mL), 4-hydroxybenzaldehyde (9.89 g, 81.0 mmol), PEG4000 (polyethylene glycol, 1.15 g ) and 1M NaOH (85 mL) and the stirred mixture was heated at 78 °C overnight. After cooling to room temperature, the reaction mixture was extracted with EtOAc and the organic phase was washed with brine, dried (Na 2 SO 4 ), filtered and evaporated in vacuo. The resulting yellow oil was chromatographed on a medium silica gel column (eluting with 0-10% EtOAc / DCM). will mainly contain higher R f Spotted fractions were combined and evaporated in vacuo to give 1.85 g (14%) of the title compound as a yellow oil. will primarily contain lower R f Spotted fractions were combined and evaporated in vacuo to give 0.64 g of the regioisomer as a colorless vis...

Embodiment 2

[0476] Example 2: Preparation of 5-{4-[2-(4-fluorophenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione

[0477]

[0478] step 1: Preparation of 4-[2-(4-fluorophenyl)-2-hydroxyethoxy]benzaldehyde

[0479] To a stirred solution of 2-(4-fluorophenyl)oxirane (5.60 g, 40.0 mmol) in toluene (65 mL) was added 4-hydroxybenzaldehyde (7.40 g, 61.0 mmol), 1M NaOH (65 mL) and PEG4000 (polyethylene glycol, 0.85 g) and the reaction mixture was heated at 78°C overnight. After cooling to room temperature, the reaction mixture was extracted with EtOAc (2 x 150 mL) and the combined extracts were washed with brine, dried (Na 2 SO 4 ), filtered and evaporated in vacuo. The resulting light brown oil was chromatographed on silica gel (eluting with 30-40% EtOAc / hexanes). will contain higher R f Spotted fractions were combined and evaporated in vacuo to give 2.38 g of the regioisomer of the product as a white solid. will contain lower R f Spotted fractions were combined and evaporated i...

Embodiment 3

[0487] Example 3: Preparation of 5-{4-[2-(2-fluorophenyl)-2-oxoethoxy]benzyl}-1,3-thiazolidine-2,4-dione

[0488]

[0489] step 1: Preparation of 2-(2-fluorophenyl)oxirane

[0490] To a solution of o-fluorostyrene (5.0 g, 41.0 mmol) and acetic acid (2.33 mL, 40.9 mmol) in dioxane (33 mL) and water (78 mL) was added N-bromosuccinyl in three portions at 0 °C Amine (8.02 g, 45.0 mol). The reaction mixture was warmed to room temperature and stirred overnight. Sodium carbonate (8.68 g, 81.9 mmol) was added in portions, followed by 1M NaOH (ca. 10 mL) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was partitioned between water and EtOAc and the aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine and dried (Na 2 SO 4 ), filtered and evaporated in vacuo to afford 5.31 g (94%) of the title compound as a light oil which was used without further purification. C 8 h7 MS(ESI+) m / z 138.1(M+H) of FO ...

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Abstract

The present invention relates to thiazolidinedione analogues of formula (I) and pharmaceutical compositions that are useful for treating and / or preventing neurodegenerative disorders.

Description

[0001] Cross-references to related applications [0002] This PCT application claims priority to US application 61 / 286,501, filed December 15, 2009, and US application 61 / 286,765, filed December 15, 2009. The entire content of the above application is incorporated into this application by reference. technical field [0003] The present invention provides thiazolidinedione analogs and pharmaceutical compositions containing thiazolidinedione analogs for use in the treatment and / or prevention of obesity or other metabolic disorders such as diabetes. Background technique [0004] Over the past few decades, scientists have postulated that PPARγ is the generally accepted site of action for insulin-sensitizing thiazolidinedione compounds. [0005] Peroxisome Proliferator Activated Receptors (PPARs), members of the nuclear hormone receptor superfamily, are ligand-activated transcription factors that regulate gene expression. PPARs are involved in autoimmune diseases as well as oth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/4439A61K31/426A61K31/4436A61P3/04
CPCA61K31/4439A61K31/4436A61K31/426A61P3/04A61P43/00
Inventor G.R.科尔卡R.F.克莱特齐恩S.P.塔尼斯S.D.拉森
Owner METABOLIC SOLUTIONS DEVMENT
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