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Deuterated aminoglycidyl compounds

A technology for compounds and mixtures, applied in the field of deuterated aminoglycidyl compounds, can solve problems such as exacerbating differences

Inactive Publication Date: 2009-09-09
AUSPEX PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

All of these transformations, in addition to other potential transformations, can occur through polymorphically expressed enzymes, thus exacerbating interpatient variability for such compounds

Method used

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  • Deuterated aminoglycidyl compounds
  • Deuterated aminoglycidyl compounds
  • Deuterated aminoglycidyl compounds

Examples

Experimental program
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preparation example Construction

[0191]Acids suitable for use in the preparation of pharmaceutically acceptable salts include, but are not limited to, acetic acid, 2,2-dichloroacetic acid, acylated amino acids, adipic acid, alginic acid, ascorbic acid, L-aspartic acid, Benzenesulfonic acid, benzoic acid, 4-acetamidobenzoic acid, boric acid, (+)-camphoric acid, camphorsulfonic acid, (+)-(1S)-camphor-10-sulfonic acid, capric acid, caproic acid, octanoic acid , cinnamic acid, citric acid, cyclamic acid, cyclamate, dodecylsulfonic acid, ethane-1,2-disulfonic acid, ethanesulfonic acid, 2-hydroxy-ethanesulfonic acid, Formic acid, fumaric acid, galactaric acid, gentisic acid, glucoheptonic acid, D-gluconic acid, D-glucuronic acid, L-glutamic acid, α-oxo-glutaric acid , glycolic acid, hippuric acid, hydrobromic acid, hydrochloric acid, hydroiodic acid, (+)-L-lactic acid, (±)-DL-lactic acid, lactobionic acid, lauric acid, maleic acid, (-)-L-maleic acid acid, malonic acid, (±)-DL-mandelic acid, methanesulfonic acid, n...

Embodiment 1

[0330] 2-(4-Benzyloxyphenyl)-methyl acetate

[0331]

[0332] To a solution of (4-hydroxy-phenyl)-acetic acid methyl ester (30 mmol) in 25 mL of anhydrous dimethylformamide was added potassium carbonate (34 mmol) and 4 mL of benzyl bromide at 0 °C under nitrogen atmosphere (34mmol). The mixture was heated to 60°C for 3 hours. After cooling to ambient temperature, the reaction mixture was poured into water. The organic phase was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. After removal of the solvent, the residue was purified by flash column chromatography to give the title compound as an oil. Yield: 83%. 1 H-NMR (CDCl 3 ): δ7.35-7.47(m, 5H); 7.23(d, J=8.8Hz, 2H); 6.96(d, J=8.8Hz, 2H); 5.07(s, 2H); 3.63(s, 3H) ; 3.60(s, 2H).

Embodiment 2

[0334] 2-(4-Benzyloxyphenyl)-ethanol

[0335]

[0336] A solution of 2-(4-benzyloxyphenyl)-acetic acid methyl ester (7.8 mmol) in dry ether (5 mL) was added to lithium aluminum hydride (15.8 mmol) in 25 mL of dry ether at 0 °C in the suspension. The reaction mixture was stirred overnight at ambient temperature, quenched with water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure to afford the title compound. Quantitative yield. 1 H-NMR (CDCl 3 ): δ7.28-7.47(m, 5H); 7.17(d, J=8.7Hz, 2H); 6.95(d, J=8.7Hz, 2H); 5.07(s, 2H); 3.85(t, J= 6.6Hz, 2H); 2.84(t, J = 6.6Hz, 2H).

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Abstract

The present invention provides substituted aminoglycidyl compounds of Formula (1), processes of preparation, and pharmaceutical compositions thereof and methods of their use for treating, preventing, or ameliorating one or more symptoms of a social anxiety disorder, an anxiety disorder, hyperthyroidism, tremor, glaucoma, hypertension, coronary artery bypass graft, chronic stable angina, atrial arrhythmia, migraine, bleeding esophageal varices, hypertrophic subaortic stenosis, heart failure, post-myocardial infarction, decreased left ventricular function after recent myocardial infarction, and / or any disorder ameliorated by beta adrenergic receptor modulators.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application No. 60 / 808,771, filed May 26, 2006, and US Provisional Application No. 60 / 840,206, filed August 25, 2006. technical field [0003] Provided herein are substituted aminoglycidyl compounds, methods for their preparation, and pharmaceutical compositions thereof. Also provided are their methods of application for treating, preventing or improving one or more of the following diseases, which include social anxiety disorder, anxiety disorder, hyperthyroidism, tremor, glaucoma, hypertension, coronary artery bypass Transplantation, chronic stable angina, atrial arrhythmia, migraine, hemorrhagic esophageal varices, hypertrophic subvalvular aortic stenosis, heart failure, post myocardial infarction, decreased left ventricular function following recent myocardial infarction, and / or Any condition improved by a beta adrenergic receptor modulator. Background technique ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/30C07C217/34C07B59/00A61K31/138
Inventor T·G·甘特S·萨沙
Owner AUSPEX PHARMA INC
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