IP Library Granted Patent US 8,053,439
Granted Patent B2
US 8,053,439 · App. 12/441,601 · Granted Nov 8, 2011

Benzophenone derivatives useful for inhibiting formation of microtubule

Assignee: Chong Kun Dang Pharmaceutical Corp.
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Quick Facts
Patent No.
US 8,053,439
App. No.
12/441,601
Granted
Nov 8, 2011
Kind
B2
Abstract

Disclosed herein are novel benzophenone derivatives represented by formula I, a pharmaceutically acceptable salt thereof, a hydrate thereof or a solvate thereof, a pharmacological composition containing the same, and a use of the composition as therapeutic drugs. The benzophenone derivatives have an inhibition activity of microtubule formation and can be used to treat a normal proliferative state of a malignant tumor by killing the actively proliferating cells.

Claims (688)

1. A compound represented by the following formula 1, a pharmaceutically acceptable salt thereof:

wherein,

R 1 , R 2 , R 3 , R 4 , and R 5 may be identical to or different from each other, may form a dioxane or dioxolane ring by connecting with adjacent carbons; wherein,

R 1 , R 3 and R 5 are each independently hydrogen, hydroxyl, hydroxyalkyl, fluoro, bromo, chloro, substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, formyl, [1,3]dioxane, or a functional group represented by the following structural formula 1,

R 2 and R 4 are each independently hydroxyl, hydroxyalkyl, fluoro, bromo, chloro, substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, formyl, [1,3]dioxane, or a functional group represented by the structural formula 1;

wherein, q is 1 or 2, and R 6 and R 7 are each independently hydrogen or C 1-3 alkyl;

Z is O;

X is C or N, provided that when X is C, Rb is hydrogen, C 1-3 alkoxy, substituted or unsubstituted C 1-6 alkyl, or a functional group represented by the structural formula 1, and when X is N, Rb does not exist;

Ra is fluoro, —CONH 2 , —COOH, nitro, —O—R 9 (wherein, R 9 is hydrogen, substituted or unsubstituted C 1-6 alkyl, phenyl, —SO 2 —R 10 , or —CO 2 R 10 , wherein R 10 is substituted or unsubstituted C 1-6 alkyl, or substituted or unsubstituted phenyl), —CO—R 10 or —COO—R 10 (wherein, R 10 is the same as defined above), or a functional group represented by the following structural formula 3,

wherein, R 11 and R 12 are each independently hydrogen, formyl, C 1-3 alkoxy, pyridine, pyrimidine, substituted or unsubstituted C 1-6 alkyl, hydroxyalkyl, —CO—R 10 , —COO—R 10 , or —SO 2 —R 10 , wherein R 10 is the same as defined above,

or a C 5 or C 6 heterocyclic ring containing at least one hetero atom selected from the group consisting of O, S, and N (the ring may not have a substituent, or may be arbitrarily substituted with at least one of substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, thiol, amino, nitro, thiomethyl, carboxylic acid, methylcarboxylate, —CF 3 , or —NR 13 R 14 , wherein R 13 and R 14 are each independently hydrogen, substituted or unsubstituted C 1-6 alkyl, hydroxyalkyl, CO—R 10 , —COO—R 10 , or —SO 2 —R 10 , wherein R 10 is the same as defined above);

Rc and Rd are each independently hydrogen, a C 5 or C 6 heterocyclic ring containing at least one hetero atom selected from the group consisting of O, S, and N (the ring may not have a substituent, or may be arbitrarily substituted with at least one of substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, or —NR 13 R 14 , wherein R 13 and R 14 are the same as defined above, and the ring may not have two oxygen), or a R 15 -substituted phenyl (wherein, R 15 is hydroxyl, nitro, substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, fluoro, nitrile, —NR 11 R 12 , —COO—R 10 , or —SO 2 —R 10 , wherein R 10 , R 11 , and R 12 are the same as defined above), provided that Rc and Rd may not be hydrogen simultaneously; and

Re is hydrogen or halogen.

2. The compound according to claim 1 , which is a compound represented by the following formula 1, a pharmaceutically acceptable salt thereof:

wherein, R 1 , R 2 , R 3 , R 4 , and R 5 may be identical to or different from each other;

R 1 , R 2 , R 4 , and R 5 are each independently hydroxyl, hydroxyalkyl, fluoro, bromo, substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, formyl, or a functional group represented by the following structural formula 1,

R 3 is selected from the group consisting of hydroxyl, hydroxyalkyl, fluoro, bromo, substituted C 1-6 alkyl, C 1-3 alkoxy, formyl, or a functional group represented by the structural formula 1.

wherein, q is 1 or 2, and R 6 and R 7 are each independently hydrogen or C 1-3 alkyl;

Z is O;

X is C or N, provided that when X is C, Rb is hydrogen, C 1-3 alkoxy, substituted or unsubstituted C 1-6 alkyl, or a functional group represented by the structural formula 1, and when X is N, Rb does not exist;

Ra is fluoro, —CONH 2 , —COOH, nitro, —O—R 9 (wherein, R 9 is hydrogen, substituted or unsubstituted C 1-6 alkyl, —SO 2 —R 10 , or —CO 2 R 10 , wherein R 10 is substituted or unsubstituted C 1-6 alkyl, or substituted or unsubstituted phenyl), or a functional group represented by the following structural formula 3,

wherein, R 11 and R 12 are each independently hydrogen, formyl, C 1-3 alkoxy, pyridine, pyrimidine, substituted or unsubstituted C 1-6 alkyl, hydroxyalkyl, —CO—R 10 , —COO—R 10 , or —SO 2 —R 10 , wherein R 10 is the same as defined above,

or a C 5 or C 6 heterocyclic ring containing at least one hetero atom selected from the group consisting of O, S, and N (the ring may not have a substituent, or may be arbitrarily substituted with at least one of substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, amino, nitro, thiomethyl, carboxylic acid, methylcarboxylate, —CF 3 , or —NR 13 R 14 , wherein R 13 and R 14 are each independently hydrogen, substituted or unsubstituted C 1-6 alkyl);

Rc and Rd are each independently hydrogen, a C 5 or C 6 heterocyclic ring containing at least one hetero atom selected from the group consisting of O, S, and N (the ring may not have a substituent, or may be arbitrarily substituted with at least one of substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, or —NR 13 R 14 , wherein R 13 and R 14 are the same as defined above, and the ring may not have two oxygen), or a R 15 —substituted phenyl (wherein, R 15 is hydroxyl, nitro, substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, fluoro, nitrile, —NR 11 R 12 , —COO—R 10 , or —SO 2 —R 10 , wherein R 10 , R 11 , and R 12 are the same as defined above), provided that Rc and Rd may not be hydrogen simultaneously; and

Re is hydrogen.

3. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Rc or Rd is a functional group selected from the group consisting of the following structural formulas,

wherein, R 16 is hydrogen, amino, or C 1-3 alkyl.

4. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Rc or Rd is a functional group selected from the group consisting of the following structural formula,

wherein, R 16 is the same as defined above.

5. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Rc or Rd is a functional group selected from the group consisting of the following structural formulas,

wherein, R 15 is the same as defined above.

6. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Ra is a functional group selected from the group consisting of the following structural formulas,

wherein, R 17 is hydrogen, substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, thiol, amino, nitro, thiomethyl, carboxylic acid, methylcarboxylate, or CF 3 .

7. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Ra is a functional group selected from the group consisting of the following structural formulas,

wherein, R 17 is hydrogen, methyl, amino, nitro, thiomethyl, carboxylic acid, methylcarboxylate, or CF 3 ,

wherein Rc or Rd is a functional group selected from the group consisting of the following structural formulas,

wherein, R 15 is hydrogen, hydroxyl, nitro, substituted or unsubstituted C 1-6 alkyl, C 1-3 alkoxy, fluoro, nitrile, —NR 11 R 12 , —COO—R 10 , or —SO 2 —R 10 , wherein R 11 , and R 12 are each independently the same as defined above; and

R 16 is hydrogen or C 1-3 alkyl.

8. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Ra is a functional group selected from the group consisting of the following structural formula,

wherein, R 11 and R 12 are each independently the same as defined above,

wherein Rc or Rd is a functional group selected from the group consisting of the following structural formulas,

wherein, R 15 and R 16 are each independently the same as defined above.

9. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Ra is a functional group selected from the group consisting of the following structural formula

10. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Ra is NH 2 .

11. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein Ra is C 1-3 alkoxy.

12. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein R 1 , R 2 , R 3 , R 4 and R 5 are each independently fluorine.

13. The compound according to claim 1 , a pharmaceutically acceptable salt thereof, wherein R 2 , R 3 and R 4 are each independently methoxy.

14. The compound according to claim 1 , wherein the compound is selected from the following compounds, a pharmaceutically acceptable salt thereof:

Compound 200

(2-methoxy-5-(pyridin-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 203

(5-(furan-2-yl)-2-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 206

(5-(furan-2-yl)-2,3-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 207

(2,3-dimethoxy-5-(pyridin-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 211

(4-methoxy-5′-nitrobiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 212

(5′-amino-4-methoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 213

(4,4′-dimethoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 214

(4,6′-dimethoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 216

(4-ethoxy-4′-methoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 218

(6′-hydroxy-4-methoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 220

(4-hydroxy-4′-methoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 223

(4′-methoxy-4-nitrobiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 224

(5-(furan 2-yl)-2-nitrophenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 225

(2-amino-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 226

(4-amino-4′-methoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 228

(4-methoxy-3-(3,4,5-trimethoxybenzoyl)phenyl)-1H-pyrrol-1-carboxylic acid tert-butyl ester,

Compound 229

(2-methoxy-5-(1H pyrrol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 231

N-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 232

(2-(benzylamino)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 233

(3-(1,3-dioxan-2-yl)-4,5-dimethoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 234

5-(5-(furan-2-yl)-2-methoxybenzoyl)-2,3-dimethoxybenzaldehyde;

Compound 235

N-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)methanesulfonamide;

Compound 236

4-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenylamino)-4-oxobutanoic acid;

Compound 237

2-amino-N-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 238

(2-(allylamino)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 239

(R)-2-amino-N-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)-3-methylbutanamide;

Compound 240

(5-(furan-2-yl)-2-hydroxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 241

methanesulfonic acid 4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl;

Compound 242

(2-(2-(dimethylamino)ethoxy)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 243

2-(4-furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenoxy)acetic acid methyl ester;

Compound 244

2-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenoxy)acetic acid;

Compound 247

(3,4-dimethoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 249

(5-(furan-2-yl)-2-methoxyphenyl)(3-(hydroxymethyl)-4,5-dimethoxyphenyl)methanone;

Compound 253

(4,5-dimethoxy-3-((methylamino)methyl)phenyl)(5-furan-2-yl)-2-methoxyphenyl)methanone;

Compound 257

(3-((dimethylamino)methyl)-4-hydroxy-5-methoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 262

(5-(furan-2-yl)-2,4-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 263

(3-((dimethylamino)methyl)-4,5-dimethoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 264

(5-(furan-2-yl)-2-methoxyphenyl)(4-methoxy-3,5-dimethylphenyl)methanone;

Compound 265

(5-(furan-2-yl)-2-methoxyphenyl)(4-(methoxymethoxy)-3,5-dimethylphenyl)methanone;

Compound 266

(5-(furan-2-yl)-2-methoxyphenyl)(4-hydroxy-3,5-dimethylphenyl)methanone;

Compound 267

(4-(2-(dimethylamino)ethoxy)-3,5-dimethylphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 268

(4-(allyloxy)-3-methoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 269

(3-allyl-4-hydroxy-5-methoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 271

N-(5-(1H-1,2,4-triazol-1-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 272

(2-amino-4-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 273

2-(4-acetamido-3-(3,4,5-trimethoxybenzoyl)phenyl)-1H-pyrrol-1-carboxylic acid tert-butyl ester;

Compound 274

N-(4-(1H-pyrrol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 275

(3-allyl-4,5-dimethoxyphenyl)((5-furan-2-yl)-2-methoxyphenyl)methanone;

Compound 276

(3-(2,3-dihydroxypropyl)-4,5-dimethoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 277

N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 278

(2-amino-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 279

N-(4-(thiophen-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 281

N-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)-N-methylacetamide;

Compound 282

(5-(furan-2-yl)-2-(methylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 283

(2-amino-5-(thiophen-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 284

(2-amino-5-(oxazol-5-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 285

N-(2-(3-(hydroxymethyl)-4,5-dimethoxybenzoyl)-4-(thiazol-2-yl)phenyl)acetamide;

Compound 286

(2-amino-5-(thiazol-2-yl)phenyl)(3-(hydroxymethyl)-4,5-dimethoxyphenyl)methanone;

Compound 289

(2-amino-5-(oxazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 290

(5-(1H-imidazol-1-yl)-2-nitrophenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 291

(2-nitro-5-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 293

(2-amino-5-(pyridin-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 294

N-(4-(2-aminothiazol-5-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 295

N-(4-(2-methylthiazol-5-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 296

N-(4-(oxazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 297

2-amino-5-(2-aminothiazol-4-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 298

(2-amino-5-(2-methylthiazol-4-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 300

N-(4-(thiophen 3-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 301

(2-amino-5-(thiophen-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 302

N-(4-(6-methoxypyridin-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 303

(2-amino-5-(6-methoxypyridin-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 306

(5-(furan-2-yl)-2-phenoxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 307

N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)propionamide;

Compound 308

N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)methanesulfonamide;

Compound 309

4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenylcarboxylic acid methyl ester;

Compound 311

N-(4-(1-methyl-1H-imidazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 312

(2-amino-5-(1-methyl-1H-imidazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 313

N-(4-(1H-pyrazol-5-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 314

3-chloro-N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)propanamide;

Compound 315

4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenylcarboxylic acid isobutyl ester;

Compound 316

N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)formamide;

Compound 317

(5-(furan-2-yl)-2-(4-methylpiperazin-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 320

4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenylcarboxylic acid hexyl ester;

Compound 321

4-methoxy-N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)benzenesulfonamide;

Compound 322

(5-(furan 2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 323

(5-(furan-2-yl)-2-(2 hydroxyethylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 324

N-(4-(2-formamidethiazol-4-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 326

(2-amino-5-(thiazol-2-yl)phenyl)(4-hydroxy-3,5-diethoxyphenyl)methanone;

Compound 327

(2-fluoro-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 329

(5-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(4-hydroxy-3,5-dimethoxyphenyl)methanone;

Compound 330

(2-(dimethoxyamino)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 331

(2-(difluoromethoxy)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 332

(3-allyl-5-(furan-2-yl)-2-hydroxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 333

(3-allyl-2-(difluoromethoxy)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 334

4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenylcarboxylic acid 2-methoxymethyl ester;

Compound 335

N-(4-(pyridin-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)methanesulfonamide;

Compound 336

(5-(furan-2-yl)-2-(1H pyrazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 337

(4,5′-diaminophenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 338

N-(5′-amino-3-(3,4,5-trimethoxybenzoyl)biphenyl-4-yl)acetamide;

Compound 339

N-(4-(pyrimidin-5-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 340

(2-amino-5-(pyrimidin-5-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 341

(5-(furan-2-yl)-2-(3-hydroxypropylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 342

N-(4-(oxazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)methanesulfonamide;

Compound 346

(5-(pyridin-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 347

(5-(thiazol-2-yl)-2-(1H-1,2,4-thiazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 348

(2-(3-hydroxypropylamino)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 350

N-(4-(pyridin-4-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 352

(2-amino-5-(pyridin-4-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 354

(5-(furan-2-yl)-2-(1H-imidazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 357

(2-fluoro-5-(isoxazol-5-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 359

(5-(oxazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 360

(2-(3 hydroxypropylamino)-5-(oxazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 363

(2-(3-hydroxypropylamino)-5-(1H-pyrrol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 364

(3-(2,3-dihydroxypropyl)-5-(furan-2-yl)-2-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 365

(2-(pyrimidin-5-yl)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 366

(5-(furan-2-yl)-2-(pyrazin-2-ylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 367

(5-(furan-2-yl)-2-(pyridin-2-ylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 368

(2-(2-(1H-imidazol-4-yl)ethylamino)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 369

(5-(furan-2-yl)-2-(3-hydroxypyrrolidin-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 370

(S)-(5-(furan-2-yl)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 371

(5-(furan-2-yl)-2-(4-(2-hydroxyethyl)piperazin-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 372

(2-(1,2-dihydroxyethyl)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 373

4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)benzoic acid;

Compound 374

4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)benzoic acid methyl ester;

Compound 375

(2-(oxazol-5-yl)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 376

(2-(3-amino-1H-1,2,4-triazol-1-yl)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 377

(3-(1,3-dioxan-2-yl)-4,5-dimethoxyphenyl)(5-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)methanone;

Compound 378

(5-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3-(hydroxymethyl)-4,5-dimethoxyphenyl)methanone;

Compound 379

(5-(furan-2-yl)-2-(1H-1,2,3,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 380

(2-(3-hydroxypropylamino)-5-(pyridin-2-yl)phenyl 3,4,5-trimethoxyphenyl)methanone;

Compound 381

(5-(pyridin-2-yl)-2-(1H-1,2,3,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 382

(5-(furan-2-yl)-2-(4-hydroxybutylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 383

(5-(furan-2-yl)-2-(pyridin-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 384

(S)-(2-(3-(dimethylamino)pyrrolidin-1-yl)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 385

(R)-(2-(3-(dimethylamino)pyrrolidin-1-yl)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 386

(S)-N-(1-(4-(furan-2-yl)-2-(3,4,5,-trimethoxybenzoyl)phenyl)pyrrolidin-3-yl)acetamide;

Compound 387

(R)-N-(1-(4-(furan-2-yl)-2-(3,4,5,-trimethoxybenzoyl)phenyl)pyrrolidin-3-yl)acetamide;

Compound 388

(S)-(2-(3-aminopyrrolidin-1-yl)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 389

(R)-(2-(3-aminopyrrolidin-1-yl)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 390

(5-(furan-2-yl)-2-morpholinophenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 391

(5-(thiophen-2-yl)-2-(1H-1,2,4,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 392

(2-(pyridin-4-yl)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 393

(4′-methoxy-4-(thiazol-2-yl)biphenyl-2-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 394

(2-(2-methoxypyridin-3-yl)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 395

(5-(thiazol-2-yl)-2-(thiophen-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 396

4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)benzoic acid methoxymethyl ester;

Compound 397

2-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)benzamido)acetic acid methyl ester;

Compound 400

(5-(1H-imidazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 401

(2-(1H-tetrazol-1-yl)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 402

(2-(3-aminophenoxy)-5-(thiophen-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 403

(2-(3-aminophenoxy)-5-(pyridin-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 408

4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)benzamide;

Compound 409

(5-(1H-pyrrol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 410

(5-(thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 411

(2-methoxy-5-(thiazol-2-yl)pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 420

(2-(4-hydroxyphenylamino)-5-(thiazol-2-yl)pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 421

(2-(3-hydroxypropylamino)-5-(thiazol-2-yl)pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 422

(2-(benzylamino)-5-(thiazol-2-yl)pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 425

(5-(furan-2-yl)-2-methoxyphenyl)(pentafluorophenyl)methanone;

Compound 426

(2-amino-5-(thiazol-2-yl)pyridin-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 427

N-(5-(thiazol-2-yl)-3-(3,4,5-trimethoxybenzoyl)pyridin-2-yl)acetamide;

Compound 429

(2-methoxy-5-(thiazol-2-yl)phenyl)(pentafluorophenyl)methanone;

Compound 434

(3-((dimethylamino)methyl)-5-(furan-2-yl)-2-hydroxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 437

(2-fluoro-4-(furan-2-yl)phenyl)(pentafluorophenyl)methanone;

Compound 443

(4-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 446

(4-(furan-2-yl)-2-(1H-1,2,4,-triazol-1-yl)phenyl)(pentafluorophenyl)methanone;

Compound 455

(4-(pyrimidin-5-yl)-2-(1H-1,2,4,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 456

(2′-hydroxy-3-(1H-1,2,4-triazol-1-yl)biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 457

(2′-hydroxy-3-(fluoro)biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 458

(2-fluoro-4-(thiophen-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 462

(4-(thiophen-3-yl)-2-(1H-1,2,4,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 463

(2-fluoro-4-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 464

(4=(thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 469

(2-(3-hydroxypropylamino)-4-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 474

(4′-methoxy-4-[1,2,4]triazol-1-yl-biphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 475

(4-(3,5-dimethyl-isoxazol-4-yl)-2-[1,2,4]triazol-1-yl-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 476

N-(3′-[1,2,4]triazol-1-yl-4′-(3,4,5-trimethoxybenzoyl)biphenyl-3-yl)methanesulfonamide;

Compound 477

(3′-hydroxy-3-[1,2,4]triazol-1-yl-biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 479

(3′-ethanesulfonyl-3-[1,2,4]triazol-1-yl-biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 480

3′-[1,2,4]triazol-1-yl-4′-(3,4,5-trimethoxybenzoyl)-biphenyl-3-carboxylic acid methyl ester;

Compound 482

(4′-methanesulfonyl-3-[1,2,4]triazol-1-yl-biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 483

N-(3′-[1,2,4]triazol-1-yl-4-(3,4,5-trimethoxybenzoyl)-biphenyl-3-yl)acetamide;

Compound 484

methanesulfonic acid 5-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl ester;

Compound 485

(4-hydroxy-3,5-dimethoxyphenyl)(5-thiazol-2-yl-2-[1,2,4]thiazol-1-yl-phenyl)methanone;

Compound 486

N-[4′-fluoro-3′-(3,4,5-trimethoxybenzoyl)-biphenyl-3-yl]-methanesulfonamide;

Compound 492

(2-amino-4-thiophen-3-yl phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 493

(2-amino-4-furan-2-yl-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 494

N-(3′-amino-4′-(3,4,5-trimethoxybenzoyl)-biphenyl-3-yl)methanesulfonamide;

Compound 495

pentafluorophenyl-(4-thiazol-2-yl-2-[1,2,4]thiazol-1-yl-phenyl)methanone;

Compound 497

(2-amino-4-thiazol-2-yl-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 499

(2-(4-methoxy-benzylamino)-4-(thiazol-2-yl)-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 500

(3,4-dimethoxy-5-((methoxymethoxy)methyl)phenyl)(4-(thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)methanone;

Compound 501

(3-hydroxymethyl-4,5-dimethoxyphenyl)(4-thiazol-2-yl-2-[1,2,4]triazol-1-yl-phenyl)methanone;

Compound 502

(2-(2-hydroxyethylamino)-4-(thiazol-2-yl)phenyl)(3-hydroxymethyl-4,5-dimethoxyphenyl)methanone;

Compound 503

(2-amino-4-thiazol-2-yl-phenyl)(3-hydroxymethyl-4,5-dimethoxyphenyl)methanone;

Compound 505

(4-(2-amino-thiazol-4-yl)-2-fluoro-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 506

3′-[1,2,4]triazol-1-yl-4′-(3,4,5-trimethoxybenzoyl)-biphenyl-3-carbonitrile;

Compound 507

(3′,5′-dimethyl-3-[1,2,4]thiazol-1-yl-biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 508

(3′-nitro-3-[1,2,4]thiazol-1-yl-biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 509

(3-hydroxymethyl-4,5-dimethoxy-phenyl)(5-thiazol-2-yl-2-[1,2,4]thiazol-1-yl-phenyl)methanone;

Compound 510

(4-thiazol-2-yl-2-[1,2,3]thiazol-1-yl-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 511

(4-pyridin-3-yl-2-[1,2,4]thiazol-1-yl-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 512

(4-(4-methoxypyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 513

(3′,5′-difluoro-3-[1,2,4]triazol-1-yl-biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 514

(3-bromo-4,5-dimethoxyphenyl)(2-fluoro-4-(thiazol-2-yl)phenyl)methanone;

Compound 515

(3-bromo-4,5-dimethoxyphenyl)(4-(thiazol-2-yl)-2-(1,2,4-triazol-1-yl)phenyl)methanone;

Compound 516

(4-(2-aminothiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 517

(4-(2-methylthiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 518

(4-(2-aminothiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(pentafluorophenyl)methanone;

Compound 525

(3′-amino-3-(1H-1,2,4-triazol-1-yl)biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 531

N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)-1H-imidazol-2-yl)acetamide;

Compound 534

(4-(thiazol-5-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 538

(4-(difluoromethoxy)-3,5-dimethoxyphenyl)(4-(thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)methanone;

Compound 547

(4-(2-aminothiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(4-(difluoromethoxy)-3,5-dimethoxyphenyl)methanone;

Compound 550

(5′-(1H-1,2,4-triazol-1-yl)-4′-(3,4,5-trimethoxybenzoyl)biphenyl-3-sulfonamide;

Compound 554

((4-(4-hydroxymethyl)thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 560

N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl)acetamide;

Compound 561

methyl 4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl carbamate;

Compound 562

(4-(thiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 563

(4-(2-(2-hydroxypropan-2-yl)thiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 564

(4-(2-(hydroxymethyl)thiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 583

(2-methoxy-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 588

(2-methoxy-5-(thiophen-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 590

(2-methoxy-5-(oxazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 594

(2-methoxy-5-(thiophen-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 595

(2-methoxy-5-(methylthiazol-4-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 596

(5-(2-methylthiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 597

(2-amino-5-(1H-pyrrol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 598

(2-methoxy-5-(1H-pyrazol-5-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 599

(4-(1H-pyrrol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 601

(2-hydroxy-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone; and

Compound 602

(4-(oxazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone.

15. The compound according to claim 1 , wherein the compound is selected from the following compounds, a pharmaceutically acceptable salt thereof:

Compound 200

(2-methoxy-5-(pyridin-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 203

(5-(furan-2-yl)-2-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 206

(5-(furan-2-yl)-2,3-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 213

(4,4′-dimethoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 249

(5-(furan-2-yl)-2-methoxyphenyl)(3-(hydroxymethyl)-4,5-dimethoxyphenyl)methanone;

Compound 264

(5-(furan-2-yl)-2-methoxyphenyl)(4-methoxy-3,5-dimethylphenyl)methanone;

Compound 265

(5-(furan-2-yl)-2-methoxyphenyl)(4-(methoxymethoxy)-3,5-dimethylphenyl)methanone;

Compound 269

(3-allyl-4-hydroxy-5-methoxyphenyl)(5-(furan-2-yl)-2-methoxyphenyl)methanone;

Compound 583

(2-methoxy-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 588

(2-methoxy-5-(thiophen-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 590

(2-methoxy-5-(oxazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 594

(2-methoxy-5-(thiophen-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 595

(2-methoxy-5-(methylthiazol-4-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone; and

Compound 598

(2-methoxy-5-(1H-pyrazol-5-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone.

16. The compound according to claim 1 , wherein the compound is selected from the following compounds, a pharmaceutically acceptable salt thereof:

Compound 224

(5-(furan 2-yl)-2-nitrophenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 225

(2-amino-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 226

(4-amino-4′-methoxybiphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 231

N-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 235

N-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)methanesulfonamide;

Compound 237

2-amino-N-(4-(furan-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 238

(2-(allylamino)-5-(furan-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 272

(2-amino-4-(1H-1,2,4-thiazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 277

N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 278

(2-amino-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 279

N-(4-(thiophen-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 282

(5-(furan-2-yl)-2-(methylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 283

(2-amino-5-(thiophen-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 286

(2-amino-5-(thiazol-2-yl)phenyl)(3-(hydroxymethyl)-4,5-dimethoxyphenyl)methanone;

Compound 289

(2-amino-5-(oxazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 293

(2-amino-5-(pyridin-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 294

N-(4-(2-aminothiazol-5-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 296

N-(4-(oxazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 297

(2-amino-5-(2-aminothiazol-4-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 298

(2-amino-5-(2-methylthiazol-4-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 300

N-(4-(thiophen-3-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)acetamide;

Compound 301

(2-amino-5-(thiophen-3-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 308

N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)methanesulfonamide;

Compound 316

N-(4-(thiazol-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)formamide;

Compound 323

(5-(furan-2-yl)-2-(2-hydroxyethylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 335

N-(4-(pyridin-2-yl)-2-(3,4,5-trimethoxybenzoyl)phenyl)methanesulfonamide;

Compound 337

(4,5′-diaminophenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 341

(5-(furan-2-yl)-2-(3-hydroxypropylamino)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 348

(2-(3-hydroxypropylamino)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 354

(5-(furan-2-yl)-2-(1H-imidazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 363

(2-(3-hydroxypropylamino)-5-(1H-pyrrol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 379

(5-(furan-2-yl)-2-(1H-1,2,3,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 380

(2-(3-hydroxypropylamino)-5-(pyridin-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 401

(2-(1H-tetrazol-1-yl)-5-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 469

(2-(3-hydroxypropylamino)-4-(thiazol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 494

N-(3′-amino-4′-(3,4,5-trimethoxybenzoyl)-biphenyl-3-yl)methanesulfonamide;

Compound 516

(4-(2-aminothiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone; and

Compound 597

(2-amino-5-(1H-pyrrol-2-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone.

17. The compound according to claim 1 , wherein the compound is selected from the following compounds, a pharmaceutically acceptable salt thereof:

Compound 322

(5-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 346

(5-(pyridin-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 347

(5-(thiazol-2-yl)-2-(1H-1,2,4-thiazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 359

(5-(oxazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 391

(5-(thiophen-2-yl)-2-(1H-1,2,4,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 400

(5-(1H-imidazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 409

(5-(1H-pyrrol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 443

(4-(furan-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 446

(4-(furan-2-yl)-2-(1H-1,2,4,-triazol-1-yl)phenyl)(pentafluorophenyl)methanone;

Compound 455

(4-(pyrimidin-5-yl)-2-(1H-1,2,4,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 462

(4-(thiophen-3-yl)-2-(1H-1,2,4,-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 464

(4-(thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 474

(4′-methoxy-4-[1,2,4]triazol-1-yl-biphenyl-3-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 475

(4-(3,5-dimethyl-isoxazol-4-yl)-2-[1,2,4]triazol-1-yl-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 476

N-(3′-[1,2,4]triazol-1-yl-4′-(3,4,5-trimethoxybenzoyl)biphenyl-3-yl)methanesulfonamide;

Compound 479

(3′-ethanesulfonyl-3-[1,2,4]triazol-1-yl-biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 506

3′-[1,2,4]triazol-1-yl-4′-(3,4,5-trimethoxybenzoyl)-biphenyl-3-carbonitrile;

Compound 511

(4-pyridin-3-yl-2-[1,2,4]thiazol-1-yl-phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 516

(4-(2-aminothiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)3,4,5-trimethoxyphenyl)methanone;

Compound 525

(3′-amino-3-(1H-1,2,4-triazol-1-yl)biphenyl-4-yl)(3,4,5-trimethoxyphenyl)methanone;

Compound 531

N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)-1H-imidazol-2-yl)acetamide;

Compound 534

(4-(thiazol-5-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 538

(4-(difluoromethoxy)-3,5-dimethoxyphenyl)(4-(thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)methanone;

Compound 547

(4-(2-aminothiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(4-(difluoromethoxy)-3,5-dimethoxyphenyl)methanone;

Compound 550

(5′-(1H-1,2,4-triazol-1-yl)-4′-(3,4,5-trimethoxybenzoyl)biphenyl-3-sulfonamide;

Compound 554

((4-(4-hydroxymethyl)thiazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 560

N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl)acetamide;

Compound 561

methyl 4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)thiazol-2-yl carbamate;

Compound 562

(4-(thiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 563

(4-(2-(2-hydroxypropan-2-yl)thiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 564

(4-(2-(hydroxymethyl)thiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 596

(5-(2-methylthiazol-4-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone;

Compound 599

(4-(1H-pyrrol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone; and

Compound 602

(4-(oxazol-2-yl)-2-(1H-1,2,4-triazol-1-yl)phenyl)(3,4,5-trimethoxyphenyl)methanone.

18. A pharmacological composition having a function of inhibiting a microtubule formation, comprising the compound according to claim 1 , a pharmaceutically acceptable salt thereof as an effective component, and a pharmaceutically acceptable carrier or excipient.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 27, 2014
From: CHONG KUN DANG HOLDINGS CORP.
To: CHONG KUN DANG PHARMACEUTICAL CORP.
Reel/Frame 033620/0229 →
CHANGE OF NAME Recorded Aug 20, 2014
From: CHONG KUN DANG PHARMACEUTICAL CORP.
To: CHONG KUN DANG HOLDINGS CORP.
Reel/Frame 033577/0682 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 17, 2009
From: CHOI, NAM-SONG; KIM, YOUNG-MI; KIM, YOUNG-HOON; LEE, JAE-KWANG; LIM, IN-TAEK; CHOI, HO-JIN; YANG, HYUN-MO; KONG, SUN-JU; MOON, SEUNG-KEE; KIM, SOO-JIN; YU, HYUN-JUNG; SHIN, JAE-SU; KWON, YOUNG-MIN; LEE, SUNG-SOOK; AHN, SOON-KIL
To: CHONG KUN DANG PHARMACEUTICAL CORP.
Reel/Frame 022407/0588 →
Priority Claims (1)
KR 10-2006-0094019 · Sep 27, 2006 · national
Continuity (1)
Related Publication 20090275575A1 · Nov 5, 2009