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Agent for regeneration and/or protection of nerves

A technology of nerve regeneration and protective agents, applied in the field of nerve regeneration and/or protective agents, capable of solving problems such as undisplayed and unrecorded EP2 agonists

Inactive Publication Date: 2008-08-06
ONO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] However, EP2 agonists, which may have EP3 agonistic effects, have neither been shown nor documented to have regenerative or protective effects on peripheral nerves

Method used

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  • Agent for regeneration and/or protection of nerves
  • Agent for regeneration and/or protection of nerves
  • Agent for regeneration and/or protection of nerves

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0296] Example 1: 4-cyclohexyl-3-hydroxyl-3-methylbutanoic acid ethyl ester (compound 1)

[0297] Add ethyl bromoacetate (11 mL), zinc (9.1 g) and iodine (1.7 g) to a solution of 1-cyclohexylacetone (10 g) in 1,4-dioxane (70 mL) at room temperature, and the mixture passes through Sonicate for 2 hours. 1N Hydrochloric acid was added dropwise to the reaction solution, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1) to obtain the title compound (15.8 g) having the following physical parameters.

[0298] TLC: Rf 0.15 (n-hexane:ethyl acetate=10:1);

[0299] NMR (CDCl 3 ): δ0.84-1.92, 2.37-2.58, 4.18.

Embodiment 2

[0300] Example 2: 4-cyclohexyl-3-methyl-1,3-butanediol (compound 2)

[0301] To a suspension of lithium aluminum hydride (3.68 g) in tetrahydrofuran (70 mL) was added dropwise a solution of compound 1 (15.8 g) in tetrahydrofuran (30 mL) at 0°C, and the mixture was stirred for 35 minutes. Ethyl acetate was added to the reaction solution at 0°C until the foam disappeared, and 5N hydrochloric acid (10 mL) was added dropwise. The reaction solution was allowed to warm to room temperature and stirred overnight. The reaction solution was dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (9.0 g) having the following physical parameters.

[0302] TLC: Rf 0.24 (n-hexane: ethyl acetate = 2: 1);

[0303] NMR (CDCl 3 ): δ0.84-2.13, 3.77-3.98.

Embodiment 3

[0304] Example 3: 1-cyclohexyl-2-methyl-4-[(1-phenyl-1H-tetrazol-5-yl)thio]-2-butanol (compound 3)

[0305] At 0°C, tetrabutylammonium bromide (1.1 g) and 5N sodium hydroxide (27 mL) were added to a solution of compound 2 (5.95 g) in toluene (60 mL), and a solution of tosyl chloride (6.7 g) was added dropwise. Suspension in toluene (20 mL). The reaction solution was stirred at room temperature for 1 hour. 1-Phenyl-1H-tetrazole-5-thiol (6.8 g) was added to the reaction solution, and the reaction solution was stirred at 60° C. for 3.5 hours. The reaction solution was extracted with tert-butoxymethyl ether. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=17:3) to obtain the title compound (9.56 g) having the following physical parameters.

[0306] TLC: Rf 0.45 (toluene: ethyl acetate = 4: 1);

[0307] NMR (CDCl 3 ): δ0.84-1.87, 1.9...

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Abstract

An EP2 agonist which may have an EP3 agonistic effect has an effect of regenerating and / or protecting nerves, and is therefore useful as a therapeutic agent for a disease of the peripheral nervous system, such as a lower or upper motor neuron disease, a nerve root disease, plexopathy, thoracic outlet compression syndrome, peripheral neuropathy, neurofibromatosis and neuromuscular transmission disease. An EP2 agonist which has an EP3 agonistic effect is a safe and effective agent for the regeneration and / or protection of nerves which has little influence on the circulatory system.

Description

technical field [0001] The present invention relates to agents for nerve regeneration and / or protection. More specifically, it relates to nerve regeneration and / or protection agents containing EP2 agonists which may have EP3 agonistic effects. Background of the invention [0002] The nervous system is broadly divided into the central nervous system and the peripheral nervous system, and particularly the peripheral nervous system is responsible for nerve transmission by connecting the brain and the spinal cord with the extremities of the body. The peripheral nervous system can be divided into the somatic nervous system (cerebrospinal nervous system) and the autonomic nervous system. In addition, the somatic nervous system is divided into cranial nerves and spinal nerves. Likewise, when classifying the somatic nervous system by function, the somatic nervous system that transmits nerve signals (stimuli) generated by sensory receptors to the central nervous system is divided i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K45/00A61K31/426A61K31/427A61K47/40A61P9/00A61P19/08A61P25/00A61P43/00C07D277/20C07D277/56C07D417/12
CPCA61K47/48969A61K31/426B82Y5/00A61K45/06C07D277/56C07D277/20C07D417/12A61K9/0019A61K31/427A61K47/6951A61P19/00A61P19/08A61P25/00A61P25/02A61P25/24A61P43/00A61P9/00A61K47/40
Inventor 大元和之木下晶博松屋秀和
Owner ONO PHARMA CO LTD
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