Thiazolidinedione derivative and use thereof

Patent metadata

Field	Value
Publication number	US-10787425-B2
Application number	US-201616068518-A
Country	US
Kind code	B2
Filing date	Aug 18, 2016
Priority date	Jan 8, 2016
Publication date	Sep 29, 2020
Grant date	Sep 29, 2020

Abstract

Provided are a novel compound represented by any one of Formulae 1a and 1b and use thereof. Provided are novel thiazolidinedione derivatives represented by any one of Formulae 1a and 1b and pharmaceutical compositions containing the same.

First claim

The invention claimed is:

1. A compound represented by any one of Formulae 1a and 1b or a pharmaceutically acceptable salt thereof:

wherein, in Formulae 1a and 1b,
A and A′ are O;
A 1 is a substituted or unsubstituted C 3 -C 10 cycloalkyl group, or an unsubstituted C 6 -C 20 aryl group;
R 1 is hydrogen or deuterium;
R 2 , R 3 and R 3 ′ are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, and a substituted or unsubstituted C 1 -C 10 alkoxy group;
R 4 and R 5 are each independently hydrogen or deuterium;
n1 is an integer from 1 to 10; and
at least one substituent of the substituted C 1 -C 10 alkoxy group and the substituted C 3 -C 10 cycloalkyl group is selected from deuterium, —F, —Cl, —Br, —I, —OH, a cyano group, a nitro group, an amino group, an amidino group, and a C 1 -C 10 alkyl group.

2. The compound or pharmaceutically acceptable salt thereof of claim 1 , wherein, in Formulae 1a and 1b, n1 is an integer from 1 to 6.

3. The compound or pharmaceutically acceptable salt thereof of claim 1 , wherein the substituted or unsubstituted C 1 -C 10 alkoxy group is an unsubstituted C 1 -C 6 alkoxy group, the substituted or unsubstituted C 3 -C 10 cycloalkyl group is an unsubstituted C 3 -C 10 cycloalkyl group, and the unsubstituted C 6 -C 20 aryl group is an unsubstituted C 6 -C 12 aryl group.

4. The compound or pharmaceutically acceptable salt thereof of claim 2 , wherein A 1 in Formulae 1a and 1b is selected from groups represented by Formulae 2-1 to 2-4, and 2-10:

wherein, in Formulae 2-1 to 2-4, and 2-10, R 11 is selected from hydrogen, deuterium, —F, —Cl, —Br, —I, and a C 1 -C 10 alkyl group, a 11 is an integer from 0 to 2, a 12 is an integer from 0 to 3, a 13 is an integer from 0 to 4, a 14 is an integer from 0 to 5, and * indicates a binding site to a neighboring atom.

5. The compound or pharmaceutically acceptable salt thereof of claim 4 , wherein R 11 in Formulae 2-1 to 2-4 is hydrogen or deuterium.

6. The compound or pharmaceutically acceptable salt thereof of claim 2 , wherein A 1 in Formulae 1a and 1b is selected from groups represented by Formulae 2-6 to 2-10:

wherein * in Formulae 2-6 to 2-10 indicates a binding site to a neighboring atom.

7. The compound or pharmaceutically acceptable salt thereof of a claim 1 , being represented by one of Formulae 3-1 to 3-5:

wherein, in Formulae 3-1 to 3-5, A 1 and n1 are the same as explained in connection with Formulae 1a and 1b, X is —F, —Cl, —Br, or —I, and R 3 is a substituted or unsubstituted C1-C 10 alkoxy group.

8. The compound or pharmaceutically acceptable salt thereof of claim 7 , wherein A 1 in Formulae 3-1 to 3-5 is selected from groups represented by Formulae 2-1 to 2-4, and 2-10:

wherein R 11 in Formulae 2-1 to 2-4, is selected from hydrogen, deuterium, —F, —Cl, —Br, —I, and a C 1 -C 10 alkyl group, a 11 is an integer from 0 to 2, a12 is an integer from 0 to 3, a 13 is an integer from 0 to 4, a14 is an integer from 0 to 5, and * indicates a binding site to a neighboring atom.

9. The compound or pharmaceutically acceptable salt thereof of claim 8 , wherein R 11 in Formulae 2-1 to 2-4, is hydrogen or deuterium.

10. The compound or pharmaceutically acceptable salt thereof of claim 7 , wherein A 1 in Formulae 3-1 to 3-5 is selected from groups represented by Formulae 2-6 to 2-10:

wherein* in Formulae 2-6 to 2-10 indicates a binding site to a neighboring atom.

11. The compound or pharmaceutically acceptable salt thereof of claim 7 , wherein the compounds represented by Formulae 3-1 to 3-4 is any one of compounds represented by 3-6 to 3-11:

wherein A 1 and n1 in Formulae 3-6 to 3-11 are the same as explained in connection with Formulae 1a and 1b.

12. The compound or pharmaceutically acceptable salt thereof of claim 1 , being selected from compounds represented by Formulae 4, 5, 7 to 10, 12 to 15, 19, 20, 22 to 25, 27 to 30, 34, 35, 37 to 40, 42 to 45, 49, 50, 52 to 55, 57 to 60, 64, 65, 67 to 70, 72 to 75, 79, 80, 82 to 85, 87 to 90, 94, 95, 97 to 100, and 102 to 105:

13. A pharmaceutical composition for increasing prostaglandin E 2 , the pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof of claim 1 as an active ingredient.

14. A method of increasing prostaglandin E 2 in a subject, the method including administering the compound or pharmaceutically acceptable salt thereof of claim 1 to the subject.

15. The method of claim 14 , for preventing alopecia or promoting hair growth in a subject, treating cardiovascular diseases, gastrointestinal diseases, kidney diseases, atopy, burns or wounds, or promoting cell regeneration or bone formation.

Assignees

• Univ Chosun Iacf

Inventors

• Cho Hoon
• Yoon Eunjeong

Classifications

• A61P9/12

  Antihypertensives · CPC title

• A61P13/12

  of the kidneys · CPC title

• A61P9/10

  for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis · CPC title

• A61P1/04

  for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants · CPC title

• A61P9/04

  Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure · CPC title