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Substituted phenethylamines with serotoninergic and/or norepinephrinergic activity

A technology of isotope enrichment and enantiomers, applied in organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., can solve problems such as noncompliance, short half-life, drug withdrawal, etc.

Active Publication Date: 2008-12-31
AUSPEX PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to its pharmacological half-life of 5-11 hours, patients taking venlafaxine are at significant risk for SRI discontinuation symptoms if the drug is stopped abruptly
Furthermore, to overcome its short half-life, the drug must be taken twice (BID) or three times (TID) per day, which increases the likelihood of patient incompliance and discontinuance

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0179] According to the method of known literature (Ouk et al., Green Chemistry, 2002, 4(5), 431-435, which is incorporated herein by reference), by making d 6 -(4-Hydroxyphenyl)-acetic acid (1 equivalent, Cambridge Isotopes Laboratories), K 2 CO 3 (0.04 equiv) and d 6 - Dimethyl carbonate (1.25 equivalents, Cambridge Isotopes Laboratories) was reacted at 160°C until complete to prepare d 9 -(4-Methoxyphenyl)-acetic acid.

Embodiment 2

[0180] The title compound was prepared by the method described by Yardley et al. in Journal of Medicinal Chemistry 1990, 33(10), 2899-2905, which is hereby incorporated by reference in its entirety. will d 9 -(4-Methoxyphenyl)-acetic acid (1 equiv) in dichloromethane was treated with oxalyl chloride (1.22 equiv) and DMF (catalytic amount) and stirred at room temperature until all the acid was converted to acid chloride. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and washed with d 6 - Treatment with dimethylamine hydrochloride (1 equiv, Cambridge Isotopes Laboratories), ethyldiisopropylamine (2.1 equiv) and DMAP (0.2 equiv). The mixture was stirred overnight. The solvent was removed under reduced pressure and the crude residue was purified by silica gel column chromatography.

Embodiment 3

[0181] The title compound was prepared according to the method described by Yardley et al. in Journal of Medicinal Chemistry 1990, 33(10), 2899-2905. d at -78°C 15 - 2-(4-Methoxyphenyl)-N,N-dimethyl-acetamide (1 eq) in THF was treated with n-butyllithium (1 eq). The mixture was stirred at -78 °C for 90 min; d was added 10- Cyclohexanone (1.2 equivalents, Sigma-Aldrich) in THF, maintaining stirring until completion. By joining D 2 O (2 equiv) quenched the reaction, the mixture was warmed to room temperature, the solvent was removed under reduced pressure, and the crude residue was purified by silica gel column chromatography.

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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 and prodrugs 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.

Description

[0001] Cross References to Related Applications [0001] This application claims U.S. Provisional Patent Application No. 60 / 741,315, filed December 1, 2005, entitled "SUBSTITUTED PHENETHYLAMINES WITH SEROTONINERGIC AND / ORNOREPINEPHRINERGIC ACTIVITY," and filed August 30, 2006, entitled "SUBSTITUTED PHENETHYLAMINES WITH SEROTONINERGIC AND / OR NOREPINEPHRINERGIC ACTIVITY," U.S. Provisional Patent Application No. 60 / 841,366, both of which are incorporated by reference in their entirety. technical field [0002] The present invention relates to monoamine neurotransmitter absorption inhibitors and pharmaceutically acceptable salts and prodrugs thereof, their chemical synthesis and the use of such compounds in the treatment and / or treatment of psychotropic disorders, anxiety disorders, general Sexual Anxiety, Depression, Post Traumatic Stress Disorder, OCD, Panic Disorder, Hot Flashes, Alzheimer's, Migraine, Hepatopulmonary Syndrome, Chronic Pain, Nociceptive Pain, Neuropathic Pain, ...

Claims

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Application Information

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IPC IPC(8): C07C217/74A61K31/135A61P25/00
Inventor T·G·甘特S·萨沙
Owner AUSPEX PHARMA INC
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