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Substituted aryloxypropylamines with serotoninergic and/or norepinephrinergic activity

An isotope enrichment and compound technology, which can be used in organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., and can solve problems such as increasing compound variability.

Inactive Publication Date: 2009-02-04
AUSPEX PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This phenomenon increases interpatient variability in response to compounding

Method used

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  • Substituted aryloxypropylamines with serotoninergic and/or norepinephrinergic activity
  • Substituted aryloxypropylamines with serotoninergic and/or norepinephrinergic activity
  • Substituted aryloxypropylamines with serotoninergic and/or norepinephrinergic activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0263] As used herein, and unless otherwise indicated, the following abbreviations have the following meanings: Me means methyl (CH 3 -), Et means ethyl (CH 3 CH 2 -), i-Pr refers to isopropyl ((CH 3 ) 2 CH 2 -), t-Bu refers to tert-butyl ((CH 3 ) 3 CH-), Ph refers to phenyl, Bn refers to benzyl (PhCH 2 -), Bz refers to benzoyl (PhCO-), MOM methoxymethyl, Ac refers to acetyl, TMS refers to trimethylsilyl, TBS refers to tert-butyldimethylsilyl, Ms methylsulfonyl (CH 3 SO 2 -), Ts refers to p-toluenesulfonyl (p-CH 3 PhSO 2 -), Tf refers to trifluoromethanesulfonyl (CF 3 SO 2 -), TfO refers to triflate (CF 3 SO 3 -), D 2 O refers to deuterium oxide, DMF refers to N,N-dimethylformamide, DCM refers to dichloromethane (CH 2 Cl 2 ), THF refers to tetrahydrofuran, EtOAc refers to ethyl acetate, Et 2 O refers to diethyl ether, MeCN refers to acetonitrile (CH 3 CN), NMP refers to 1-N-methyl-2-pyrrolidone, DMA refers to N, N-dimethylacetamide, DMSO refers to dimethylsu...

Embodiment 2-d3-3

[0274] Example 2-d 3 -3-Methyl-amino-1-thiophen-2-yl-propan-1-ol

[0275]

[0276]A solution of ethyl (3-hydroxy-3-thiophen-2-yl-propyl)-carbamate (0.367 g, 1.6 mmol) in dry tetrahydrofuran (5 mL) was dissolved at 0 °C under nitrogen atmosphere for 8 min Add dropwise to a stirred suspension of lithium aluminum deuteride (0.202 g, 4.81 mmol) in dry tetrahydrofuran (15 mL). The mixture was refluxed for 2 hours, cooled to 0 °C, treated dropwise with water (0.150 mL) for 10 minutes, stirred for 30 minutes, treated with ethyl acetate (50 mL), stirred for 30 minutes, treated with ethyl acetate (50 mL), room temperature Stir for 30 minutes and vacuum filter. The solid was rinsed with ethyl acetate (5 mL) and the filtrate was concentrated in vacuo to give 280 mg of a slightly cloudy off-white oil which solidified upon storage at -7°C overnight. The solid was taken up in ethyl acetate (5 mL), dried (Na 2 SO 4 ), filtered and concentrated in vacuo to give the desired product, d ...

Embodiment 3-d3

[0278] Example 3-d 3 -Methyl-[3-(naphthyl-1-yloxy)-3-thiophen-2-yl]-propyl]-amine (d 3 -B)

[0279]

[0280] Under nitrogen atmosphere, d 3 -3-Methyl-amino-1-thiophen-2-yl-propan-1-ol (0.133g, 0.760mmol) and sodium hydride (60% in mineral oil) (0.046g, 1.15mmol) in dimethyl ethylene Sulfone (2.0 mL) was stirred at 50°C for 40 minutes. 1-Fluoronaphthalene (0.167 mg, 1.15 mmol) was added and the mixture was stirred at 70 °C under nitrogen for 2 h, cooled to 0 °C, treated with water (5 mL, added over 1 min), stirred for 5 min and treated with acetic acid Ethyl ester (5x4mL) was extracted. The combined organic fractions were dried (Na 2 SO 4 ), filtered and concentrated in vacuo. The crude product was purified by column chromatography (dichloromethane-methanol-NH 4 OH) to give 60.8 mg of a clear light brown oil which was taken up in hexane (3 mL) and washed with concentrated aqueous sodium bicarbonate (2x1 mL), water (2x1 mL), concentrated aqueous sodium chloride (1 mL)...

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PUM

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Abstract

Chemical syntheses and medical uses of novel inhibitors of the uptake of monoamine neurotransmitters and pharmaceutically acceptable salts thereof, for the treatment and / or management of psychotropic disorders, anxiety disorder, generalized anxiety disorder, depression, post-traumatic stress disorder, obsessive-compulsive disorder, panic disorder, hot flashes, senile dementia, migraine, hepatopulmonary syndrome, chronic pain, nociceptive pain, neuropathic pain, painful diabetic retinopathy, bipolar depression, obstructive sleep apnea, psychiatric disorders, premenstrual dysphoric disorder, social phobia, social anxiety disorder, urinary incontinence, anorexia, bulimia nervosa, obesity, ischemia, head injury, calcium overload in brain cells, drug dependence, and / or premature ejaculation are described in Formula (I).

Description

[0001] Cross References to Related Applications [0002] This application claims U.S. Provisional Application 60 / 739,261, filed November 23, 2005, entitled "Substituted Aryloxypropylamines Having Serotonerogenic and / or Noradrenergic Activity," and filed August 11, 2006 Priority was filed to US Provisional Application 60 / 837,830, entitled "Substituted Aryloxypropylamines Having Serotoninogenic and / or Noradrenergic Activity," both of which are incorporated by reference in their entirety. Background of the invention [0003] field of invention [0004] The present invention relates to monoamine neurotransmitter uptake inhibitors and their pharmaceutically acceptable salts and prodrugs, their chemical synthesis and the medical use of such compounds for the treatment of psychotropic disorders, anxiety disorders , generalized anxiety disorder, depression, post-traumatic stress disorder, obsessive-compulsive disorder, panic disorder, hot fl...

Claims

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Application Information

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IPC IPC(8): C07B59/00C07C217/16C07C217/20A61P25/00A61K31/13A61K31/381
Inventor T·G·甘特S·萨沙
Owner AUSPEX PHARMA INC
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