Pharmaceutically Acceptable Salts And Prodrug


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.
Figure US09422225-20160823-C00001

This application claims the benefit of priority of U.S. provisional application No. 60/933,214, filed Jun. 4, 2007, the disclosure of which is hereby incorporated by reference as if written herein in its entirety.


The present invention is directed to substituted phenethylamines, pharmaceutically acceptable salts and prodrugs thereof, the chemical synthesis thereof, and medical use of such compounds for the treatment and/or management of nasal congestion, migraine, asthma, chronic obstructive pulmonary diseases, ischemic heart disease, hypotension, and/or any disorder ameliorated by modulating alpha-adrenergic receptors.


Phenylephrine (Neo-Synephrine®), (R)-3-(1-hydroxy-2-methylamino-ethyl)-phenol, is an orally and intravenously administered putative agonist of the alpha adrenergic receptor (α1-selective). Phenylephrine is available over the counter as a nasal decongestant. Phenylephrine can also effectively treat hypotension (Rose et al., Neurocritical Care 2004, 1(3), 287-299), and is used frequently in intensive care units to maintain adequate tension in patients. Phenylephrine is not inotropic or chronotropic, it elevates the blood pressure without increasing the heart rate or contractility. Phenylephrine can also treat migraines (Willems et al., Drug News Perspectives 2002, 15(3), 140-146) and ischemic heart disease (Cohen et al., Annual Review of Medicine 1996, 47, 21-29).

The chemical structure of phenylephrine contains a number of positions that are susceptible to action by metabolic enzymes. For example, the N-methyl group can be oxidized which could then lead to a norepinephrine-like structure, if coupled with an appropriate aromatic hydroxylation. The methylene group alpha to the nitrogen is likely to oxidized, since the hydroxymandelic acid metabolite accounts for more than 50% of the recovered mass balance. Monoamine oxidase (MAO) is responsible for much of the clearance.


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