Phenylcarbamate compound and muscle relaxant containing the same

A carbamate and carbamoyl technology, applied in the field of muscle relaxation compositions, can solve problems such as side effects

Active Publication Date: 2013-05-01
BIO PHARM SOLUTIONS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs act on interneurons of the spinal cord, thereby inhibiting monosynaptic reflexes and polysynaptic reflexes, and thus may cause side effects such as central nervous system depression, muscle weakness, and the like

Method used

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  • Phenylcarbamate compound and muscle relaxant containing the same
  • Phenylcarbamate compound and muscle relaxant containing the same
  • Phenylcarbamate compound and muscle relaxant containing the same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0079] Preparation Example 1: Synthesis of 1-(2-chlorophenyl)-trans-1-propene

[0080]

[0081] In a flask, 48 ml of 2-chlorobenzaldehyde (0.42 mol) and 49.7 ml of 3-pentanone (0.47 mol) were dissolved in 600 mL of hexane, and then stirred as the temperature increased. Add 53.6ml of boron trifluoride etherate (BF 3 OEt 2 , 0.42mol). When the reaction was complete, 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 washed with anhydrous magnesium sulfate (MgSO 4 ) dehydrated and concentrated. The concentrated residue was purified by silica gel column chromatography to give the title compound (38 g, yield 58%).

[0082] 1 H NMR (400MHz, CDCl 3 )δ1.94(d, J=4.8Hz, 3H), 6.24(m, 1H), 6.78(d, J=14Hz, 1H), 7.11~7.51(m, 4H)

preparation Embodiment 2

[0083] Preparation Example 2: Synthesis of 1-(2-chlorophenyl)-trans-1-butene

[0084]

[0085]Except for using 3-heptanone instead of 3-pentanone, substantially the same method as described in Preparation Example 1 was performed to obtain the title compound (2.9 g, yield 83%).

[0086] 1 H NMR (400MHz, CDCl 3 )δ1.14(d, J=7.6Hz, 3H), 2.29~2.33(m, 2H), 6.28(dt, J=16Hz, 6.4Hz, 1H), 6.78(d, J=15.6Hz, 1H), 7.13~7.54(m, 4H)

preparation Embodiment 3

[0087] Preparation Example 3: Synthesis of 1-(2-chlorophenyl)-3-methyl-trans-1-butene

[0088]

[0089] Except for using 2,6-dimethyl-heptan-4-one instead of 3-pentanone, substantially the same method as described in Preparation Example 1 was carried out to obtain the title compound (8.0 g, yield 50-90%) .

[0090] 1 H NMR (400MHz, CDCl 3 )δ1.14(d, J=6.8Hz, 6H), 2.25~2.57(m, 1H), 6.20(dd, J=16Hz, 7.2Hz, 1H), 7.64(d, J=16Hz, 1H), 7.12 ~7.54(m, 4H)

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PUM

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Abstract

A novel phenylcarbamate compound and a pharmaceutical composition containing the same are provided. More specifically, a novel phenylcarbamate compound, a composition for muscle relaxation containing the phenylcarbamate compound as an active ingredient, and a method of muscle relaxation comprising administering a therapeutically effective amount of the phenylcarbamate compound, are provided.

Description

Background of the invention [0001] (a) Field of Invention [0002] The present invention relates to a novel phenyl carbamate compound and a pharmaceutical composition containing the compound. More specifically, the present invention relates to a phenylcarbamate compound and a pharmaceutically acceptable salt thereof (the phenylcarbamate compound has a relatively high muscle-relaxing effect and low toxicity), and compounds containing the compound and / or or a pharmaceutically acceptable salt thereof as an active ingredient for muscle relaxation. [0003] (b) Description of related technologies [0004] Myotonia or spasms are often observed as sequelae of cerebrovascular disorders such as stroke or sequelae of traumatic brain injury and are not amenable to treatment. [0005] Myotonia or spasm is one of skeletal muscle dysfunction diseases due to increased muscle tone, and is caused by damage to the central nervous system due to various causes such as external injury, cerebrov...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/14C07C31/42A61K31/27A61P21/02
CPCC07C271/12C07C33/46A61K31/27C07C2101/02C07C2101/14C07C2102/42C07C271/24A61P9/00A61P19/00A61P21/00A61P21/02A61P25/00C07C2601/02C07C2601/14C07C2602/42C07C271/14
Inventor 崔溶文
Owner BIO PHARM SOLUTIONS
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