Use of 7-alkoxy fangchinoline compounds in preventing, alleviating and/or treating depression

Patent metadata

Field	Value
Publication number	US-9169268-B2
Application number	US-201414507584-A
Country	US
Kind code	B2
Filing date	Oct 6, 2014
Priority date	Apr 6, 2012
Publication date	Oct 27, 2015
Grant date	Oct 27, 2015

Abstract

The present invention provides a method of preventing, alleviating and/or treating depression, comprising the step of administering to a subject in need thereof a therapeutically effective amount of a 7-alkoxy fangchinoline compound or a pharmaceutically acceptable derivative thereof.

First claim

What is claimed is:

1. A method of alleviating and/or treating depression, comprising the step of administering to a subject in need thereof a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof,

wherein,
R 1 is an alkyl of formula —C n H 2n+1 , wherein n is an integer greater than or equal to 1 and smaller than or equal to 6;
R 2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and acyl;
X 1 , X 2 , X 3 and X 4 may be the same or different, and each independently represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, hydroxyl or methoxy; and
when n is 1, X 1 , X 2 , X 3 and X 4 may not all be hydrogen.

2. The method of claim 1 , wherein R 1 is methyl, and at least one of X 1 , X 2 , X 3 and X 4 represents fluorine, chlorine, bromine, iodine or nitro.

3. The method of claim 1 , wherein R 1 is methyl, and X 1 and X 3 each independently represent chlorine or bromine.

4. The method of claim 1 , wherein R 1 is methyl, and X 1 and X 3 are the same and represent chlorine or bromine.

5. The method of claim 3 , wherein R 2 is methyl.

6. The method of claim 1 , wherein n is 2, 3 or 4.

7. The method of claim 6 , wherein R 2 is methyl.

8. The method of claim 1 , wherein the compound of formula (I) is selected from the group consisting of 5-chloro-7-methoxy fangchinoline (Compound 1), 5,14-dibromo-7-methoxy fangchinoline (Compound 2), 7-ethoxy fangchinoline (Compound 3), 5-bromo-7-ethoxy fangchinoline (Compound 4), 5,14-dibromo-7-ethoxy fangchinoline (Compound 5), 7-propoxy fangchinoline (Compound 6), 7-butoxy fangchinoline (Compound 7), and 7-isopropoxy fangchinoline (Compound 8).

9. A compound of formula (I) or a pharmaceutically acceptable salt thereof,

wherein,
R 1 is ethyl;
R 2 is methyl;
X 1 , X 2 , X 3 and X 4 may be the same or different, each independently represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, hydroxyl or methoxy, and X 1 , X 2 , X 3 and X 4 may not all be hydrogen.

10. The compound or a pharmaceutically acceptable salt thereof of claim 9 , wherein X 1 and X 3 each independently represent fluorine, chlorine, bromine, iodine or nitro.

11. The compound or a pharmaceutically acceptable salt thereof of claim 9 , wherein X 1 and X 3 each independently represent chlorine or bromine.

12. The compound or a pharmaceutically acceptable salt thereof of claim 9 , wherein X 1 and X 3 are the same and represent chlorine or bromine.

13. The compound or a pharmaceutically acceptable salt thereof of claim 9 , wherein the compound of formula (I) is selected from the group consisting of 5-bromo-7-ethoxy fangchinoline (Compound 4) and 5,14-dibromo-7-ethoxy fangchinoline (Compound 5).

14. A method of alleviating and/or treating schizophrenia, comprising the step of administering to a subject in need thereof a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof,

wherein,
R 1 is an alkyl of formula —C n H 2n+1 , wherein n is an integer greater than or equal to 1 and smaller than or equal to 6;
R 2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl and acyl;
X 1 , X 2 , X 3 and X 4 may be the same or different, and each independently represent hydrogen, fluorine, chlorine, bromine, iodine, nitro, hydroxyl or methoxy; and
when n is 1, X 1 , X 2 , X 3 and X 4 may not all be hydrogen.

15. The method of claim 14 , wherein the compound of formula (I) is selected from the group consisting of 5-chloro-7-methoxy fangchinoline (Compound 1), 5,14-dibromo-7-methoxy fangchinoline (Compound 2), 7-ethoxy fangchinoline (Compound 3), 5-bromo-7-ethoxy fangchinoline (Compound 4), 5,14-dibromo-7-ethoxy fangchinoline (Compound 5), 7-propoxy fangchinoline (Compound 6), 7-butoxy fangchinoline (Compound 7), and 7-isopropoxy fangchinoline (Compound 8).

Assignees

• Univ Beijing

Inventors

• Zhang Yonghe
• Zhang Xueqiong
• Sheng Zhaofu

Classifications

• A61K31/4748

  forming part of bridged ring systems (strychnine A61K31/475; morphinan derivatives A61K31/485) · CPC title

• C07D498/16 Primary

  Peri-condensed systems · CPC title

• A61P25/24

  Antidepressants · CPC title