IP Library › Granted Patent US 9,296,690
Granted Patent B2
US 9,296,690 · App. 14/293,879 · Granted Mar 29, 2016

Method for inhibiting differentiation of osteoclast and pharmaceutical composition comprising thereof

Inventors: Bae Keun Park (Wonju-si, KR); Sung-Hwa Yoon (Suwon-si, KR); Ju-Young Park (Suwon-si, KR); Sung Hoon Park (Gunpo-si, KR)
Assignee: METACINE, INC.
C07D207/448A61K31/4015C07D207/20C07D207/38C07D207/408C07D207/444C07D207/452C07D207/456C07D409/04
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Quick Facts
Patent No.
US 9,296,690
App. No.
14/293,879
Granted
Mar 29, 2016
Kind
B2
Abstract

The present invention is for method of treating metabolic bone disease, new compounds and pharmaceutical compositions comprising the active ingredients having inhibition effects on osteoclast differentiation. The pharmaceutical composition comprising new compounds according to the present invention can be used as medicines for treating metabolic bone diseases such as bone metastatic cancer, solid cancer bone metastasis, musculoskeletal complication by solid cancer bone metastasis, hypercalcemia by malignant tumor, multiple myeloma, primary bone tumor, osteoporosis, rheumatoid arthritis, osteoarthritis, periodontal disease, inflammatory resorption of alveolar bone, inflammatory resorption of bone, and Paget's disease.

Claims (60)

1. A method of treating metabolic bone disease, the method comprising: single or multiple administration of a pharmaceutical composition comprising the compound selected from the group consisting of:

1-(2,6-diisopropylphenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1,3,4-triphenyl-1H-pyrrole-2,5-dione;

1-(2-chlorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(3-chlorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(4-chlorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

3,4-diphenyl-1-(2-(trifluoromethyl)phenyl)-1H-pyrrole-2,5-dione;

1-cyclohexyl-3,4-diphenyl-1H-pyrrole-2,5-dione;

4-(2,5-dioxo-3,4-diphenyl-2,5-dihydro-1H-pyrrol-1-yl)-2-hydroxybenzoic acid;

5-(2,5-dioxo-3,4-diphenyl-2,5-dihydro-1H-pyrrol-1-yl)-2-hydroxybenzoic acid;

3-chloro-1,4-diphenyl-1H-pyrrole-2,5-dione;

3-chloro-1-(2-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

3-chloro-1-(3-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

3-chloro-1-(4-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

1-(2-fluorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(3-fluorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(4-fluorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-benzyl-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(2-fluorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(3-fluorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(4-fluorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-phenethyl-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(2-fluorophenethyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(3-fluorophenethyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(4-fluorophenethyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

3-(2-chlorophenyl)-1-(4-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

3-(3-chlorophenyl)-1-(4-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

1,3-bis(4-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

1-(4-chlorophenyl)-3-(2,6-dichlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

1-(4-chlorophenyl)-5-hydroxy-3,4-diphenyl-1H-pyrrol-2(5H)-one;

1-(4-chlorophenyl)-3,4-diphenyl-1H-pyrrol-2(5H)-one;

1-(4-chlorophenyl)-3-((dimethylamino)methyl)-3,4-diphenylpyrrolidin-2-one;

3-hydroxy-1,4-diphenyl-1H-pyrrole-2,5-dione;

1-(4-chlorophenyl)-3-phenyl-4-(thiophen-2-yl)-1H-pyrrole-2,5-dione;

4-chloro-5-hydroxy-1,3-diphenyl-1H-pyrrol-2(5H)-one; and

1-(4-chlorophenyl)-3,4-diphenyl-2,5-dihydro-1H-pyrrole;

or pharmaceutically acceptable salts thereof,

wherein the metabolic bone disease is selected from the group consisting of bone metastatic cancer, solid cancer bone metastasis, musculoskeletal complication by solid cancer bone metastasis, hypercalcemia by malignant tumor, multiple myeloma, primary bone tumor, osteoporosis, Rheumatoid Arthritis, Osteoarthritis, Periodontal Disease, inflammatory resorption of alveolar bone, inflammatory resorption of bone and Paget's disease.

2. The method of treating metabolic bone disease according to claim 1 , the pharmaceutical composition comprising the compound selected from the group consisting of

1-(4-chlorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

4-(2,5-dioxo-3,4-diphenyl-2,5-dihydro-1H-pyrrol-1-yl)-2-hydroxybenzoic acid;

5-(2,5-dioxo-3,4-diphenyl-2,5-dihydro-1H-pyrrol-1-yl)-2-hydroxybenzoic acid;

3-chloro-1-(2-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

3-chloro-1-(3-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

1-(2-fluorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(3-fluorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(2-fluorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(3-fluorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(4-fluorobenzyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(2-fluorophenethyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(3-fluorophenethyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

1-(4-fluorophenethyl)-3,4-diphenyl-1H-pyrrole-2,5-dione;

3-(2-chlorophenyl)-1-(4-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

3-(3-chlorophenyl)-1-(4-chlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

1-(4-chlorophenyl)-3-(2,6-dichlorophenyl)-4-phenyl-1H-pyrrole-2,5-dione;

1-(4-chlorophenyl)-5-hydroxy-3,4-diphenyl-1H-pyrrol-2(5H)-one;

1-(4-chlorophenyl)-3-((dimethylamino)methyl)-3,4-diphenylpyrrolidin-2-one;

1-(4-chlorophenyl)-3-phenyl-4-(thiophen-2-yl)-1H-pyrrole-2,5-dione; and

4-chloro-5-hydroxy-1,3-diphenyl-1H-pyrrol-2(5H)-one, or pharmaceutically acceptable salts thereof.

3. The method of treating metabolic bone disease according to claim 1 , the pharmaceutical composition comprising 1-(4-chlorophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dione as an active ingredient.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 18, 2014
From: PARK, BAE KEUN; YOON, SUNG-HWA; PARK, JU-YOUNG; PARK, SUNG HOON
To: METACINE, INC.
Reel/Frame 033339/0821 →
Priority Claims (1)
KR 10-2012-0082248 · Jul 27, 2012 · national
Continuity (2)
Continuation In Part 13664173 · Oct 30, 2012
Related Publication 20140275203A1 · Sep 18, 2014