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Phenylpropyl carbamate derivatives for use in preventing or treating multiple sclerosis

a technology of phenylpropyl carbamate and derivatives, which is applied in the direction of drug compositions, biocide, cardiovascular disorders, etc., can solve the problems of affecting the communication between nerve cells in the brain and spinal cord, and achieve excellent treatment effect on multiple sclerosis and low toxicity

Inactive Publication Date: 2013-07-18
BIO PHARM SOLUTIONS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0006]An embodiment provides an organic compound, i.e., phenyl carbamate compound. More particularly, the embodiment provides a phenyl carbamate compound of the following Chemical Formula 1, an enantiomer or a diastereomer thereof, or a mixture of enantiomers or diastereomers; or a pharmaceutically acceptable salt of organic acid or inorganic acid thereof; which has remarkably excellent treatment effect on multiple sclerosis as well as very low toxicity. Also, the compounds of formula I may be useful as a drug especially for the treatment of multiple sclerosis:
[0018]Continuing its research work in the field of multiple sclerosis, the present inventors, as results of studies on the development of anti-multiple sclerosis drugs, found that a substituted phenyl carbamate compounds of the following Chemical Formula 1 exhibits remarkably excellent anti-multiple sclerosis activity in various emulation models and simultaneously has very low toxicity, and completed the invention.
[0070]As demonstrated in the following experimental examples, the compound of Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or pharmaceutically acceptable salt thereof exhibits an excellent effect on preventing, improving and / or treating multiple sclerosis. Therefore, another embodiment provides a pharmaceutical composition for preventing and / or treating multiple sclerosis containing a phenyl carbamate compound represented by Chemical Formula 1; a racemate, an enantiomer, a diastereomer, a mixture of enantiomers, or a mixture of diastereomers thereof; or a pharmaceutically acceptable salt thereof, as an active ingredient.

Problems solved by technology

As a result of this damage, the ability of nerve cells in the brain and spinal cord to communicate with each other is compromised.

Method used

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  • Phenylpropyl carbamate derivatives for use in preventing or treating multiple sclerosis
  • Phenylpropyl carbamate derivatives for use in preventing or treating multiple sclerosis
  • Phenylpropyl carbamate derivatives for use in preventing or treating multiple sclerosis

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

Synthesis of 1-(2-chlorophenyl)-trans-1-propene

[0101]

[0102]48 ml of 2-chlorobenzenaldehyde (0.42 mol) and 49.7 ml of 3-pentanone

[0103](0.47 mol) were dissolved in 600 mL of hexane in flask, and then stirred with raising the temperature. 53.6 ml of Boron trifluoride etherate (BF3OEt2, 0.42 mol) was added to the resultant under reflux conditions. When the reaction was completed, water was added thereto. After layer separation, the obtained organic layer was washed twice with 1M sodium hydroxide solution (1M NaOH), and then the separated organic layer was washed with water. The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4) and concentrated. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (38 g, yield 58%).

[0104]1H NMR (400 MHz, CDCl3) δ1.94 (d, J=4.8 Hz, 3H), 6.24 (m, 1H), 6.78 (d, J=14 Hz, 1H), 7.11˜7.51 (m, 4H)

preparation example 2

Synthesis of 1-(2-chlorophenyl)-trans-1-butene

[0105]

[0106]The substantially same method as described in Preparation Example 1 was conducted, except that 3-heptanone was used instead of 3-pentanone, to obtain the title compound (2.9 g, yield 83%).

[0107]1H NMR (400 MHz, CDCl3) δ1.14 (d, J=7.6 Hz, 3H), 2.29˜2.33 (m, 2H), 6.28 (dt, J=16 Hz, 6.4 Hz, 1H), 6.78 (d, J=15.6 Hz, 1H), 7.13˜7.54 (m, 4H)

preparation example 3

Synthesis of 1-(2-chlorophenyl)-3-methyl-trans-1-butene

[0108]

[0109]The substantially same method as described in Preparation Example 1 was conducted, except that 2,6-dimethyl-heptan-4-one was used instead of 3-pentanone, to obtain the title compound (8.0 g, yield 50˜90%).

[0110]1H NMR (400 MHz, CDCl3) δ1.14 (d, J=6.8 Hz, 6H), 2.25˜2.57 (m, 1H), 6.20 (dd, J=16 Hz, 7.2 Hz, 1H), 7.64 (d, J=16 Hz, 1H), 7.12˜7.54 (m, 4H)

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Abstract

A phenyl carbamate compound, and a method of treating and / or preventing multiple sclerosis comprising administering a pharmaceutically effective amount of the phenyl carbamate compound to a subject in need of treating and / or preventing multiple sclerosis, are provided.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This application claims priority to and the benefit of U.S. Provisional Application No. 61 / 580,409, filed in the United States Patent and Trademark Office on Dec. 27, 2011, the entire contents of which are incorporated herein by reference.TECHNICAL FIELD[0002]The present invention provides a pharmaceutical composition for treating and / or preventing multiple sclerosis comprising a phenyl carbamate compound as an active ingredient, a use of the phenyl carbamate compound for phenyl carbamate compound, and a method of treating and / or preventing multiple sclerosis comprising administering a pharmaceutically effective amount of the phenyl carbamate compound to a subject in need of treating and / or preventing multiple sclerosis.BACKGROUND ART[0003]Multiple sclerosis (MS) is a chronic disease of the central nervous system (CNS), where the fatty myelin sheaths around the axons of the brain and spinal column are damaged, resulting in the inhibition o...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C271/28C07C271/24C07C271/12
CPCC07C271/28C07C2602/42C07C271/12C07C271/24C07F7/1804C07C271/02C07C271/16A61K31/325C07C33/36A61K31/165A61K31/047A61K31/164C07C2601/02C07C2601/14C07C33/26A61P21/02A61P25/00A61P25/04A61P25/06A61P25/08A61P25/28A61P29/00A61P9/00A61P9/10A61K31/16C07C271/10
Inventor CHOI, YONG MOON
Owner BIO PHARM SOLUTIONS
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