Phenylacetate derivatives or pharmaceutically acceptable salts thereof, preparation method thereof and composition for prevention or treatment of diseases induced by activation of T-type calcium ion channel containing the same as an active ingredient

1. A phenylacetate derivative represented by the following Chemical Formula 1, or pharmaceutically acceptable salt thereof:

wherein,

X is independently or selectively one or more substituents selected from the group consisting of H, halogen, and a C 1-4 alkoxy;

R 1 is a C 1-4 linear or branched alkyl; and

R 2 is

wherein R 3 and R 4 are independently or selectively H, a C 1-4 linear or branched alkyl, or a C 1-4 alkoxy.

2. The phenylacetate derivative or pharmaceutically acceptable salt thereof as set forth in claim 1 , wherein

X is independently or selectively one or more substituents selected from the group consisting of H, fluoride, chloride, bromide, methoxy and ethoxy;

R 1 is methyl, ethyl, propyl, and isopropyl; and

R 2 is

wherein R 3 and R 4 are independently or selectively H, methyl, ethyl, methoxy or ethoxy.

3. The phenylacetate derivative or pharmaceutically acceptable salt thereof as set forth in claim 1 , wherein

X is one or more substituents selected from the group consisting of H, fluoride, bromide and ethoxy;

R 1 is methyl or ethyl; and

R 2 is

wherein R 3 and R 4 are independently or selectively H, methyl or methoxy.

4. The phenylacetate derivative or pharmaceutically acceptable salt thereof as set forth in claim 1 , wherein the phenylacetate derivative is selected from the group consisting of:

(1) 5-{[3-(1H-benzimidazole-2-yl)propyl]methylamino}-2-(4-bromophenyl)-2-isopropylpentanoic acid methyl ester;

(2) methyl 5-((3-(1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-isopropyl-2-(4-methoxyphenyl)pentanoate;

(3) methyl 2-isopropyl-5-((3-(5-methoxy-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-(4-methoxyphenyl)pentanoate;

(4) methyl 5-((3-(5,6-dimethyl-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-isopropyl-2-(4-methoxyphenyl)pentanoate;

(5) methyl 5-((3-(1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-(3,4-dimethoxyphenyl)-2-isopropylpentanoate;

(6) methyl 2-(3,4-dimethoxyphenyl)-2-isopropyl-5-((3-(5-methoxy-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)pentanoate;

(7) methyl 2-(3,4-dimethoxyphenyl)-5-((3-(5,6-dimethyl-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-isopropylpentanoate;

(8) ethyl 5-((3-(1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-isopropyl-2-phenylpentanoate;

(9) ethyl 5-((3-(5,6-dimethyl-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-isopropyl-2-phenylpentanoate;

(10) methyl 2-(4-bromophenyl)-5-((3-(5,6-dimethyl-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-isopropylpentanoate;

(11) methyl 2-(4-bromophenyl)-2-isopropyl-5-((3-(5-methoxy-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)pentanoate;

(12) methyl 5-((3-(1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-(3-bromophenyl)-2-isopropylpentanoate;

(13) methyl 2-(3-bromophenyl)-2-isopropyl-5-((3-(5-methoxy-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)pentanoate;

(14) methyl 2-(3-bromophenyl)-5-((3-(5,6-dimethyl-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-isopropylpentanoate;

(15) methyl 5-((3-(1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-(4-fluorophenyl)-2-isopropylpentanoate;

(16) methyl 2-(4-fluorophenyl)-2-isopropyl-5-((3-(5-methoxy-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)pentanoate; and

(17) methyl 5-((3-(5,6-dimethyl-1H-benzo[d]imidazole-2-yl)propyl)(methyl))amino)-2-(4-fluorophenyl)-2-isopropylpentanoate.

5. A method for preparing the phenylacetate derivative of claim 1 as represented by the following Chemical Formula 1, comprising:

preparing an ester compound of Chemical Formula 3 by esterification reaction of a carboxyl acid compound of Chemical Formula 2 as a starting material in the presence of an acid catalyst (Step 1);

preparing a compound of Chemical Formula 4 by reacting the compound of Chemical Formula 3 obtained from step 1 with t-butoxide and isopropyl bromide (Step 2);

preparing a compound of Chemical Formula 5 by reacting the compound of Chemical Formula 4 obtained from step 2 with 1,3-dibromopropane (Step 3); and

preparing a compound of Chemical Formula 1 by reacting the compound of Chemical Formula 5 obtained from step 3 with a compound of Chemical Formula 6 (Step 4),

wherein, R 1 , R 2 , R 3 , R 4 , and X are as defined in claim 1 .

6. The method as set forth in claim 5 , wherein, in Step 1, after the carboxyl acid compound of Chemical Formula 2 is dissolved in methanol, the compound of Chemical Formula 3 is obtained by heating or refluxing the mixture at 85-95° C. in the presence of sulfuric acid for 2-4 hours.

7. The method as set forth in claim 5 , wherein, in Step 2, after the compound of Chemical Formula 3 and t-butoxide is dissolved in anhydrous dimethylformamide, the compound of Chemical Formula 4 is obtained by adding isopropyl bromide into the mixture and stirring the mixture at room temperature for 2-4 hours.

8. The method as set forth in claim 5 , wherein, in Step 3, after a solution of n-butyllithium in hexane is added to a solution of diisopropylamine in anhydrous tetrahydrofuran at −75-−80° C., the compound of Chemical Formula 5 is obtained by adding the compound of Chemical Formula 4 to the tetrahydrofuran solution with stirring, adding 1,3-dibromopropane dropwise to the tetrahydrofuran solution, and stirring the solution at room temperature overnight.

9. The method as set forth in claim 5 , wherein, in Step 4 when the compound of Chemical Formula 5 is reacted with the compound of Chemical Formula 6, the compound of Chemical Formula 1 is obtained by dissolving the compound of Chemical Formula 5 into methanol, adding the compound of Chemical Formula 6 and potassium carbonate, and heating or refluxing the mixture at 85-95° C. for 2-4 hours.

10. A phenylacetate derivative intermediate represented by the following Chemical Formula 3, Chemical Formula 4, or Chemical Formula 5:

wherein

X is independently or selectively one or more substituents selected from the group consisting of H, halogen, and a C 1-4 alkoxy;

R 1 is a C 1-4 linear or branched alkyl; and

R 2 is

wherein R 3 and R 4 are independently or selectively H, a C 1-4 linear or branched alkyl, or a C 1-4 alkoxy.