Compound having inhibitory activity against O-glusacase and use thereof

1 . A compound represented by Chemical Formula 1 below or a pharmaceutical salt thereof:

wherein,

D is a ring selected from the group consisting of substitutable C3 to C10 cycloalkyl, substitutable 5-membered unsaturated or aromatic ring, substitutable 6-membered unsaturated or aromatic ring, substitutable 5-membered unsaturated or aromatic heterocyclic ring, and substitutable 6-membered unsaturated or aromatic heterocyclic ring, or a polycyclic ring in which two or more rings selected from the group are fused,

X 1 is C, N, O or S,

X 2 is N or O,

R 1 , R 2 and R 3 are each independently hydrogen or C1 to C5 alkyl,

L is a direct bond or a C1 to C12 alkylene group, and

n is an integer of 0 to 3.

2 . The compound of claim 1 , wherein the compound of Chemical Formula 1 above includes compounds represented by Chemical Formulas 2 to 4 below:

wherein,

A, B, and C are each independently a ring selected from the group consisting of substitutable C3 to C10 cycloalkyl, substitutable 5-membered unsaturated or aromatic ring, substitutable 6-membered unsaturated or aromatic ring, substitutable 5-membered unsaturated or aromatic heterocyclic ring, and substitutable 6-membered unsaturated or aromatic heterocyclic ring, or a polycyclic ring in which two or more rings selected from the group are fused,

R 1 , R 2 , R 3 and n are the same as defined in claim 1 above, and

X is N or O.

3 . The compound of claim 2 , wherein in Chemical Formula 2, A is selected from the following substituents:

4 . The compound of claim 2 , wherein in Chemical Formula 3, B is selected from the following substituents:

5 . The compound of claim 2 , wherein in Chemical Formula 4, C is selected from the following substituents:

6 . The compound of claim 2 , wherein the compound of Chemical Formula 2 above includes compounds A-1 to A-41 below:

Code

Structure

Name

A-1

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-phenylacetamide

A-2

phenyl 2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl) acetate

A-3

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(p-tolyl)acetamide

A-4

2-(4-((2-acctamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(o-tolyl)acetamide

A-5

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-o-tolyl)acetamide

A-6

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(4-isopropylphenyl) acetamide

A-7

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(4-methoxyphenyl) acetamide

A-8

2-(4-((2-acetamidotiazol-3- yl)methyl)piperazin-1-yl)- N-(4-methoxyphenethyl) acetamide

A-9

2-(4-((2-acetamidotiazol-5- yl)methyl)piperazin-1-yl)- N-(3-methoxyphenyl) acetamide

A-10

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(3,4- dimethoxyphenyl)acetamide

A-11

2-(4-((2-acetamidoilsazo]-5- yl)methyl)piperazin-1-yl)- N-(4-fluorophonyl)acetamide

A-12

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(4-chlorophenyl)acetamide

A-13

2-(4-((2-acetainidothiazol-5- yl)methyl)piperazin-1-yl)- N-(2-bromo-4-chlorophenyl) acetamide

A-14

N-(4-acetamidophenyl)-2-(4- ((2-acetamidothiazol-5-yl) methyl)piperazin-1-yl) acetamide

A-15

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(pyridin-2-yl)acetamide

A-16

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(6-methylpyridin-2-yl) acetamide

A-17

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(5-methylpyridin-2-y]) acetamide

A-18

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(4-methylpyridin-2-yl) acetamide

A-19

2-(4-((2-acctamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(pyrazin-2-yl)acetamide

A-20

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-cyclohexylacetamide

A-21

2-(4-((2-acctamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(thiazol-2-yl)acetamide

A-22

2-(4-((2-acetamidothiazol-5- yl)methyl piperazin-1-yl)- N-(quinolin-6-yl)acetamide

A-23

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(quinoxalin-6-yl)acetamide

A-24

2-(4-((2-acetamidothiazol53- yl)methyl)piperazin-1-yl)- N-(naphthalen-1-yl)acetamide

A-25

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(1H-indol-5-yl)acetamide

A-26

2-(4-((2-acetamidothiazol-5- yl)methylpiperazin-1-yl)- N-(IH-benzo[d]imidazol-2- yl)acetamide

A-27

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(benzo[d]thiazol-2-yl) acetamide

A-28

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(6-methoxybenzo[d]thiazol- 2-yl)acetamide

A-29

2-(4-((2-acetanidothiazol-5- yl)methyl)piperazin-1-yl)- N-(6-ethoxybenzo[d]thiazol- 2-yl)acetamide

A-30

2-(4-((2-acetamidothiazol-5 N-(4-chlorobenzo[d]thiazol- 2-yl)acetamide

A-31

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-methyl-N-phenylacetamide

A-32

2-(4-((2-acetamidothiazol-5- yl)methyl)-3-methylpipenzin- 1-yl)-N-phenylacetamide

A-33

2-(4-((2-acetamidothiazol-5- yl)methyl)-3-methylpiperazin- 1-yl)-N-(4-fluorophenyl) acetamide

A-34

2-(4-((2-acetamidothiazol-5- yl)methyl)-3-methylpiperazin- 1-yl)-N-(4-chloropbenyl) acetamide

A-35

2-(4-((2-acetamidothiazol-5- yl)methyl)-3-methylpiperzin- 1-yl)-N-cyclohexylacetamide

A-36

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(4-(4-acetylpiperazin-1-yl) phenyl)acetamide

A-37

2-(4-((2-acetamidothiazol-5- yl)methyl)-3-methylpiperazin- 1-yl)-N-(4-(4-acetylpiperazin- 1-yl)phenylacetamide

A-38

2-(4-((2-acetamidothiazol-5- yl)methyl)piperazin-1-yl)- N-(4-benzylphenyl)acetamide

A-39

2-(4-((2-acetamidothiazol-5- yl)methyl)-3-methylpiperazin- 1-yl)-N-(4-benzylphenyl) acetamide

A-40

N-([1,1′-biphenyl]-4-ylmethyl)- 2-(4-((2-acetamidothiazol- 5-yl)methyl)piperazin-1- yl)acetamide

A-41

N-([1,1′-biphenyl]-4-ylmethyl)- 2-(4-((2-acetamidothiazol- 5-ylmethyl)-3-methylpiperazin- 1-yl)acetamide.

7 . The compound of claim 2 , wherein the compound of Chemical Formula 3 above includes compounds B-1 to B-19 below:

Code

Structure

Name

B-1

1-((2-acetantidothiazol- 5-yl)methyl)-N- phenylpiperidine-4- carboxamide

B-2

1-((2-acetamidothiazol- 5-yl)methyl)-N-(4- chlorophenyl) piperidine-4- carboxamide

B-3

1-((2-acetamidothiazol- 5-ylmethyl)-N-(4- isopropylphenyl) piperidine-4- carboxamide

B-4

1-((2-acetamidothiazol- 5-yl)methyl)-N-(pyrazin- 2-yl)piperidine-4- carboxamide

B-5

1-((2-acetamidothiazol- 5-ylmethyl)-N- cyclohexylpiperidine-4- carboxamide

B-6

1-((2-acciamidothiazol- 5-yl)methyl)-A-(quinolin- 6-ybpiperidine-4- carboxamide

B-7

1-((2-acetamidothiazol- 5-yl)methyl)-A- benzylpiperidine-4- carboxamide

B-8

1-((2-acctamidothiazol- 5-yl)methyl)-N-(4- methoxybenzyl) piperidine-4- carboxamide

B-9

1-((2-acetamidothiazol- 5-yl)methyl-N-(1-(benzo [d][1,3]dioxol-5-yl)ethyl) piperidine-4-carboxamide

B-10

1-((2-acetamidothiazol- 5-yl)methyl)-N-(1- phenylethyl)piperidine- 4-carboxamide

B-11

1-((2-acetamidothiazol- 5-yl)methyl)-N-(1-(p-tol yl)ethyl)piperidine-4- carboxamide

B-12

1-((2-acetamidothiazol- 5-ylmethyl)-N-(1- (naphthalen-2-yl)ethyl) piperidine-4-carboxamide

B-13

1-(benzo[d][1,3]dioxol- 5-yl)ethyl 1-((2- acetamidothiazol-5- yl)methyl) piperidine-4- carboxylate

B-14

1-((2-acetamidothiazol- 5-yl)methyl)-N-(p-tolyl) piperidine-4-carboxamide

B-15

1-((2-acetamidothiazol- 5-yl)methyl)-N- (4-fluorophenyl) piperidine-4-carboxamide

B-16

1-((2-acetamidothiazol- 5-yl)methyl)-N- phenylpiperdine- 3-carboxamide

B-17

1-((2-acetamidothiazol- 5-yl)methyl)-N-(4- fluorophenyl)piperdine- 3-carboxamide

B-18

1-((2-acetamidothiazol- 5-yl)methyl)-N-(4- isopropylphenyl)piperdine- 3-carboxamide

B-19

1-((2-acetamidothiazol- 5-yl)methyl)-N-(4- cyclohexylpiperdine- 3-carboxamide.

8 . The compound of claim 2 , wherein the compound of Chemical Formula 4 above includes compounds C-1 to C-8 below:

Code

Structure

Name

C-1

2-(1-((2-acctamidothiazol- 5-yl)methyl)piperidin- 4-ylidene)-N- phenylacetamide

C-2

2-(1-((2-acetamidothiazol- 5-ylmethyl)piperidin- 4-ylidene)-N-(4-fluoro phenyl)acetamide

C-3

2-(1-((2-acetamidothiazol- 5-ylmethyl)piperidin- 4-ylidene)-N-(4-chloro phenyl)acetamide

C-4

2-(1-((2-acetamidothiazol- 5-yl)methyl)piperidin- 4-ylidene)-N-(4- isopropylphenyl) acetamide

C-5

2-(1-((2-acetamidothiazol- 5-yl)methyl)piperidin- 4-ylidene)-N-(4- methoxyphenyl)acetamide

C-6

2-(1-((2-acetamidothiazol- 5-yl)methyl)piperidin- 4-ylidene)-N-(3,4- dimethoxyphenyl) acetamide

C-7

2-(1-((2-acetamidothiazol)- 5-yl)methylppiperidin- 4-ylidene)-N-(4- methoxybenzyl) acetamide

C-8

2-(1-((2-acetamidothiazol- 5-yl)methyl)piperidin-4- ylidene)-N- cyclohexylacetamide.

9 . The compound of claim 6 , wherein the compound A-34 is a compound A-34S represented by Chemical Formula 5 below as an(S)-form compound of enantiomers:

10 . A pharmaceutical composition for treating diseases caused by hyperphosphorylation of tau, comprising the compound according to claim 1 or a pharmaceutical salt thereof as an active ingredient.

11 . A method for treating a disease caused by hyperphosphorylation of tau, the method comprising

administering the pharmaceutical composition according to claim 10 .

12 . The method of claim 11 , wherein the disease is selected from the group consisting of cerebral stroke, stroke, memory loss, memory impairment, dementia, amnesia, Parkinson's disease, Alzheimer's disease, Pick's disease, Creutzfeld-Jakob disease, Huntington's disease, multiple sclerosis, amyotrophic lateral sclerosis (ALS), frontotemporal dementia (FTD), progressive supranuclear palsy (PSAP), corticobasal degeneration (CBD), and Lou Gehrig's disease.