# US 8,541,380 B2 · C-aryl glucoside SGLT2 inhibitors and pharmaceutical compositions comprising same

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- Number: US 8,541,380 B2
- Document ID: US8541380B2
- Status: Granted
- Kind: B2
- Application number: 13/379,301
- Filed: 2010-06-18
- Published: 2012-04-26
- Granted: 2013-09-24
- Earliest claimed: 2009-06-19
- Assignees: The Green Cross Corporation
- Applicants: Jinhwa Lee; Suk Ho Lee; Hee Jeong Seo; Min Ju Kim; Suk Youn Kang; Jeongmin Kim; Sung-Han Lee; Myung Eun Jung; Eun Jung Son; Kwang-Seop Song; Mi-Soon Kim
- Inventors: Jinhwa Lee; Suk Ho Lee; Hee Jeong Seo; Min Ju Kim; Suk Youn Kang; Jeongmin Kim; Sung-Han Lee; Myung Eun Jung; Eun Jung Son; Kwang-Seop Song; Mi-Soon Kim
- Web page: https://patentgrep.com/patent/US8541380B2

## CPC

- C07D 417/14: containing three or more hetero rings
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- C07D 405/10: linked by a carbon chain containing aromatic rings
- C07D 405/14: containing three or more hetero rings
- C07D 409/14: containing three or more hetero rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/10: linked by a carbon chain containing aromatic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A novel C-aryl glucoside compound, or a pharmaceutically acceptable salt or a prodrug thereof having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney; and a pharmaceutical composition comprising the same as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly, diabetes, are provided.

## Claims

### Claim 1

A compound of formula (I), or a pharmaceutically acceptable salt or a prodrug thereof:
wherein,
Ring A is selected from the group consisting of benzene ring, substituted benzene ring, naphthalene ring and substituted naphthalene ring;
Ring B is selected from the group consisting of pyridazine ring, substituted pyridazine ring, pyridazinone ring, substituted pyridazinone ring, thiadiazole ring, substituted thiadiazole ring, triazine ring, substituted triazine ring, benzotriazine ring and substituted benzotriazine ring; and
X is —CH2—.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Ring A is
R1a, R2a, R3a, R1b, R2b, R3b, R1c, R2c, and R3c being each independently hydrogen, halogen, hydroxy, C1-4 alkyl, substituted C1-4 alkyl, C2-4 alkenyl, substituted C2-4 alkenyl, C2-4 alkynyl, substituted C2-4 alkynyl, hydroxyl (C1-4 alkyl), (C1-8 alkoxy)(C1-4 alkyl), C1-8 alkoxy, C3-7 cycloalkyl, C3-7 cycloalkenyl, C3-7 cycloalkyloxy, phenyl(C1-8 alkoxy), cyano, nitro, amino, mono- or di-(C1-4 alkyl)amino, alkanoylamino, carboxy, (C1-8 alkoxy)carbonyl, carbamoyl, mono- or di-(C1-4 alkyl)carbamoyl, alkanoyl, (C1-4 alkyl)sulfonylamino, phenylsulfonylamino, (C1-4 alkyl)sulfinyl, (C1-4 alkyl) sulfonyl, phenylsulfonyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl heterocycle, or substituted heterocycle, and
Ring B is
in which, R4 is C1-2 alkoxy, C1-4 alkylthio, C1-7 alkyl, substituted C1-7 alkyl, C2-7 alkenyl, substituted C2-7 alkenyl, C2-7 alkynyl, substituted C2-7 alkynyl, C3-7 cycloalkyl, substituted C3-7 cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl or substituted heterocycloalkyl;
R5 is hydrogen, halogen, cyano, amino, mono- or di-(C1-4 alkyl)amino, C1-8 alkoxy, substituted C1-8 alkoxy, cycloalkyloxy, heterocyclooxy, C1-4 alkylthio, —S-aryl, C1-8 alkoxycarbonyl, C1-7 alkyl, substituted C1-7 alkyl, C2-7 alkenyl, substituted C2-7 alkenyl, C2-7 alkynyl, substituted C2-7 alkynyl, C3-7 cycloalkyl, substituted C3-7 cycloalkyl, C3-7 cycloalkenyl, substituted C3-7 cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocycloalkyl, or substituted heterocycloalkyl;
R6 and R7 are each independently hydrogen or methyl;
R8 is hydrogen, halogen, cyano, amino, mono- or di-(C1-4 alkyl)amino, C1-8 alkoxy, substituted C1-8 alkoxy, cycloalkyloxy, heterocyclooxy, C1-4 alkylthio, —S-aryl, C1-8 alkoxycarbonyl, C1-7alkyl, substituted C1-7 alkyl, C2-7 alkenyl, substituted C2-7 alkenyl, C2-7 alkynyl, substituted C2-7 alkynyl, C3-7 cycloalkyl, substituted C3-7 cycloalkyl, C3-7 cycloalkenyl, substituted C3-7 cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, or substituted heterocyclic;
R9 is hydrogen, C1-7 alkyl, substituted C1-7 alkyl, C2-7 alkenyl, substituted C2-7 alkenyl, C2-7 alkynyl, substituted C2-7 alkynyl, C3-7 cycloalkyl, substituted C3-7 cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, or substituted heterocyclic; and
R10 is hydrogen, halogen, cyano, C1-4 alkoxy, substituted C1-4 alkoxy, C1-4 alkyl, substituted C1-4 alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, or substituted heterocyclic.

### Claim 3 (depends on 2)

The compound of claim 2, which is selected from the group consisting of the compounds of formulae (Ia) to (Id):
wherein,
RA is halogen, C1-4 alkyl or C1-4 alkoxy; and
R4 to R10 have the same meanings as defined in claim 2.

### Claim 4 (depends on 1)

The compound of claim 1, which is selected from the group consisting of:
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(5-methylfuran-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(3-methylfuran-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(furan-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(thiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((5-(Benzo[b] thiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-(3-methylthiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(5-chlorothiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(3-chlorothiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(thiophen-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(1-methyl-1H-pyrrol-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(5-methylisoxazol-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(thiazol-4-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(2-(pyridin-4-yl)thiazol-5-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(pyridin-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(6-methylpyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(quinolin-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(isoquinolin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-cyclopentyl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(3R,4R,5S,6R)-2-(4-Chloro-3-((5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(3R,4R,5S,6R)-2-(4-Chloro-3-((5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(3R,4R,5S,6R)-2-(4-chloro-3-((5-p-tolyl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(3R,4R,5S,6R)-2-(4-Chloro-3-((5-(4-propylphenyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(3R,4R,5S,6R)-2-(4-Chloro-3-((5-cyclohexyl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(3R,4R,5S,6R)-2-(4-Chloro-3-((5-((4-methylcyclohexyl)methyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(3R,4R,5S,6R)-2-(4-Chloro-3-((5-(2-phenylpropyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(3R,4R,5S,6R,E)-2-(4-Chloro-3-((5-styryl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-phenyl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-(4-Chlorophenyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((5-(Benzofuran-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-propyl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((5-Butyl-1,3,4-thiadiazol-2-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-pentyl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-heptyl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3S,4R,5R)-2-(Hydroxymethyl)-6-(3-((5-phenyl-1,3,4-thiadiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3S,4R,5R)-2-(Hydroxymethyl)-6-(3-((5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(5-phenylfuran-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(2,2,2-trifluoroethyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(methylthio)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-methoxy-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(pyrazin-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(pyridazin-4-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(6-methylpyridin-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-(2-methylpyridin-4-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((6-(1,3,4-Thiadiazol-2-yl)pyridazin-3-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(5-methyloxazol-2-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-chloropyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
Methyl 6-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)pyridazine-3-carboxylate;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(phenylethynyl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-ethoxypyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-propoxypyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
(2S,3R,4R,5S,6R)-2-(3-((6-Butoxypyridazin-3-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(pentyloxy)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(hexyloxy)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(octyloxy)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-isopropoxypyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-isobutoxypyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(cyclohexyloxy)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(tetrahydro-2H-pyran-4-yloxy)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-chloro-3-((6-phenylpyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-chloro-3-((6-(furan-2-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(furan-3-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(pyridin-3-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(thiophen-2-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-chloro-3-((6-(thiophen-3-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((6-(Benzo[d][1,3]dioxol-5-yl)pyridazin-3-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(5-methylthiophen-2-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(4-fluorophenyl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(3-methoxyphenyl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-ethylpyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-methylpyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-propylpyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-isopropylpyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-[((6-Butylpyridazin-3-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-isobutylpyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-pentylpyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(methylthio)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(ethylthio)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(phenylthio)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((5-methyl-6-(methylthio)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
6-(2-Chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-4-methylpyridazin-3(2H)-one;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-morpholinopyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(phenylamino)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-(pyrrolidin-1-yl)pyridazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((7-methylbenzo[e][1,2,4]triazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-(Benzo[e][1,2,4] triazin-3-ylmethyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((1,2,4-triazin-3-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-phenyl-1,2,4-triazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-((6-methoxy-1,2,4-triazin-3-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)naphthalene-1-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-methoxynaphthalen-1-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(3-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-hydroxynaphthalen-1-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(4-((5-(Furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)naphthalen-2-yl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol;
(2S,3R,4R,5S,6R)-2-(2,4-Dichloro-5-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol; and
(2S,3R,4R,5S,6R)-2-(4-Chloro-5-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-2-methoxyphenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol.

### Claim 5 (depends on 2)

A method for preparing a compound of formula (Ie) comprising the steps of:
subjecting a compound of formula (II) to a coupling reaction with a hydrazide of formula (III) to obtain an acylhydrazide of formula (IV), or converting the compound of formula (II) to a hydrazide of formula (V) using hydrazine, followed by a coupling reaction of the hydrazide of formula (V) with a carboxylic acid of formula (VI) to obtain an acylhydrazide of formula (IV);
conducting a cyclization of the acylhydrazide of formula (IV) using Lawesson's reagent to obtain a thiadiazole of formula (VII); and
carrying out deprotection of the benzyl groups of the thiadiazole of formula (VII), followed by peracylation and hydrolysis of the resulting compound,
wherein,
Ring A is selected from the group consisting of benzene ring, substituted benzene ring, naphthalene ring and substituted naphthalene ring; and
R4 has the same meaning as defined in claim 2.

### Claim 6 (depends on 2)

A method for preparing a compound of formula (If), comprising the steps of:
subjecting a compound of formula (II) to a coupling reaction and cyclization with thiosemicarbazide using phosphorus(V) oxychloride to obtain an aminothiadiazole;
converting the aminothiadiazole to a thiadiazole of formula (VIII) using sodium nitrite and copper under an acidic condition; and
treating the thiadiazole of formula (VIII) with NaR4 (in which R4 has the same meaning as defined claim 2), followed by deprotection of benzyl groups,
wherein,
Ring A is selected from the group consisting of benzene ring, substituted benzene ring, naphthalene ring and substituted naphthalene ring.

### Claim 7 (depends on 1)

A method for preparing the compound of formula (Ig) comprising the steps of:
subjecting a compound of formula (IX) to a reaction with 3,6-dichloropyridazine or 3-(methylsulfonyl)-5-phenyl-1,2,4-triazine under a basic condition to obtain an ester of formula (X);
conducting a hydrolyzation and decarboxylation of the ester of formula (X) using lithium hydroxide to obtain a compound of formula (XI); and
removing the benzyl groups of the compound of formula (XI),
wherein,
Ring A is selected from the group consisting of benzene ring, substituted benzene ring, naphthalene ring and substituted naphthalene ring, and
in which R8 and R9 have the same meanings as defined claim 1.

### Claim 8

A method for preparing the compound of formula (Ih) comprising the steps of:
subjecting a compound of formula (XII) to a reaction with NaOR11, NaSMe or HNR12R13 (R11, R12R13 are each independently H or C1-4 alkyl); a Fe(III)-mediated alkylation using Grignard reagent; a Sonogashira reaction with ethynylbenzene; a Palladium(0)-catalyzed cyanation under microwave irradiation; or a Suzuki-Miyaura coupling with boronic acid, to obtain a compound of formula (XIII); and
removing the benzyl groups of the compound of formula (XIII),
wherein,
Ring A is selected from the group consisting of benzene ring, substituted benzene ring, naphthalene ring and substituted naphthalene ring, and
R14 is C1-4 alkyl, C1-4 alkoxy, —SCH3, phenylethynyl, cyano, amino or aryl.

### Claim 9 (depends on 2)

A method for preparing the compound of formula (II) comprising the steps of:
subjecting a compound of formula (IX) to a reaction with a chlorobenzotriazine compound to obtaine a triazine oxide;
conducting a reduction of the triazine oxide to obtain a compound of formula (XIV);
hydrolyzing the compound of formula (XIV) using metal hydroxide to obtain a compound of formula (XV); and
removing benzyl groups of the compound of formula (XV),
wherein,
Ring A is selected from the group consisting of benzene ring, substituted benzene ring, naphthalene ring and substituted naphthalene ring, and R10 has the same meaning as defined in claim 2.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1 as an active ingredient, and a pharmaceutically acceptable carrier.

### Claim 11 (depends on 10)

The pharmaceutical composition according to claim 10, which is for treating diabetes.

### Claim 12 (depends on 1)

A method for treating a metabolic disorder, which comprises administering the compound of claim 1 to a mammal in need thereof,
wherein the metabolic disorder is selected from the group consisting of diabetes, hyperglycemia and disorders arising from hyperglycemia.

### Claim 13 (depends on 1)

A method for inhibiting sodium-dependent glucose cotransporter 2 in a mammal, which comprises administering the compound of claim 1 to the mammal.

### Claim 14 (depends on 2)

A pharmaceutical composition comprising the compound of claim 2 as an active ingredient, and a pharmaceutically acceptable carrier.

### Claim 15 (depends on 3)

A pharmaceutical composition comprising the compound of claim 3 as an active ingredient, and a pharmaceutically acceptable carrier.

### Claim 16 (depends on 4)

A pharmaceutical composition comprising the compound of claim 4 as an active ingredient, and a pharmaceutically acceptable carrier.