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Derivatives of tryptamine and analogous compounds, and pharmaceutical formulations containing them

Inactive Publication Date: 2005-01-27
NEURIM PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

In still another aspect, the invention provides a method for treating a medical condition in a mammal (human or non-human) which is susceptible to alleviation by treatment with a medicament which interacts with the m

Problems solved by technology

The presently known subtypes are not sufficient to evaluate the large variety of melatonin effects and additional receptor subtypes await discovery.

Method used

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  • Derivatives of tryptamine and analogous compounds, and pharmaceutical formulations containing them
  • Derivatives of tryptamine and analogous compounds, and pharmaceutical formulations containing them
  • Derivatives of tryptamine and analogous compounds, and pharmaceutical formulations containing them

Examples

Experimental program
Comparison scheme
Effect test

example 1

N-(2,4-dinitrophenyl)tryptamine (ML-25)

1 mMole of tryptamine was dissolved in 100 ml of water and the pH was adjusted to pH 8.3 with 2.5 moles of sodium bicarbonate (NaHCO3), A 1.5% solution of 2,4-dinitrofluorobenzene in 200 liters ethanol was added and the mixture was stirred during 2 hours at room temperature. The desired product precipitates out, it is washed and dried. The product is obtained in 90% yield, and TLC (chloroform, silica-gel plates, reveals one yellow spot (Rf=0.84) which is well resolved from the starting materials under the same conditions.

example 2

N-(2,4-dinitrophenyl)-5-methyltryptamine (ML-28)

1 mMole of 5-metyltryptamine was dissolved in 100 ml of water and the pH was adjusted to pH 8.3 with 2.5 moles of sodium bicarbonate (NaHCO3), A 1.5% solution of 2,4-dinitrofluorobenzene in 200 ml ethanol was added and the mixture was stirred during 2 hours at room temperature. The desired product precipitates out, it is washed and dried. The product is obtained in 85% yield, and TLC (chloroform, silica-gel plates, reveals one yellow spot (Rf=0.8) which is well resolved from the starting materials under the same conditions.

example 3

2,4-dinitro-5-tryptylaminoacetanilide (ML-26)

1 mMole of tryptamine was dissolved in 100 ml of water and the pH was adjusted to pH 8.3 with 2.5 moles of sodium bicarbonate (NaHCO3), A 1.5% solution of 2,4-dinitro-5-fluoroacetanilide in 200 ml ethanol was added and the mixture was stirred during 2 hours at room temperature. The desired product precipitates out, it is washed and dried. The product is obtained in 80% yield, and TLC (chloroform, silica-gel plates, reveals one yellow spot (Rf=0.76) which is well resolved from the starting materials under the same conditions.

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Abstract

This invention relates to the administration of novel substituted tryptamines and related derivatives for the treatment of several types of medical conditions, such as prostate conditions, impotence, cardiovascula disorders, central nervous system and psychiatric disorders (such as sleep disorders, epilepsy and other convulsive disorders, anxiety, neurodegenerative diseases), chronobiological-based disorders (such as jet lag, delayed sleep syndrome, shift-work-associated sleep disorder or seasonal affective disorder), endocrine indications, neoplastic conditions, conditions associated with senescence, ophthalmological diseases, cluster headaches and migraines, and weight gain disorders.

Description

BACKGROUND OF THE INVENTION Melatonin is the principal hormone secreted by the pineal gland in all vertebrates. In all mammals studied to date, including humans, a nocturnal rise in the production of melatonin by the pineal gland is evident; melatonin production by the body is acutely suppressed by light. Melatonin is involved in the coordination of photoperiod dependent and physiological processes. The ability of the animals or humans to respond to the melatonin signal may depend upon melatonin receptors. Melatonin acts on the CNS to affect neural mechanisms through receptors located in the brain. Additionally, a number of studies indicate the existence of direct effects of melatonin in peripheral organs via peripheral melatonin receptors. Melatonin receptors are present in the heart, lungs, prostate gland, gonads, white blood cells, retina, pituitary, thyroid, kidney, gut and blood vessels. Retention patterns of radioactive-melatonin injected to rats demonstrate melatonin accumul...

Claims

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Application Information

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IPC IPC(8): A61K31/4045A61K31/404A61P3/04A61P3/10A61P5/00A61P5/06A61P7/02A61P9/10A61P9/12A61P13/08A61P15/00A61P15/10A61P15/12A61P25/00A61P25/04A61P25/06A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/28A61P27/02A61P35/00A61P37/02A61P39/06C07D209/12C07D209/16
CPCC07D209/16C07D209/12A61P13/00A61P13/08A61P15/00A61P15/10A61P15/12A61P25/00A61P25/04A61P25/06A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/28A61P27/02A61P35/00A61P3/04A61P37/02A61P39/06A61P5/00A61P5/06A61P7/02A61P9/00A61P9/10A61P9/12A61P3/10
Inventor ZISAPEL, NAVALAUDON, MOSHE
Owner NEURIM PHARMA
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