ALKALOIDS AND THEIR PREPARATION AND APPLICATION AS ANTI-HSV-1 AGENTS

• US 20180028523A1
• Filed: 10/02/2017
• Published: 02/01/2018
• Est. Priority Date: 09/06/2015
• Status: Active Grant

• Current Assignee: Ocean University of China
• Original Assignee: Ocean University of China
• Inventors: SHAO, Changlun, WANG, Changyun, MU, Xiaofeng, XU, Rufang
• Granted Patent: US 10,639,303 B2
• Time in Patent Office: Days
• CPC Class Codes: A61K 31/341 not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
• CPC Class Codes: A61K 31/4704 2-Quinolinones, e.g. carbostyril
• CPC Class Codes: A61P 31/22 for herpes viruses
• CPC Class Codes: C07D 215/22 attached in position 2 or 4
• CPC Class Codes: C07D 405/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C12N 1/145 Fungal isolates
• CPC Class Codes: C12N 2710/16063 by chemical treatment
• CPC Class Codes: C12P 17/12 containing a six-membered hetero ring
• CPC Class Codes: C12P 17/16 containing two or more hetero rings thiamine open chain analogs C12P17/167, i.e. not condensed among themselves or through a common carbocyclic ring system
• CPC Class Codes: C12R 2001/645 Fungi ; Processes using fungi

Abstract

The present invention provides alkaloids with formula I, II, III, IV, or V and their pharmaceutically acceptable salts, their preparation and their uses as antivirus drugs, for example, for treatment of HSV-1 infection. The alkaloids with formula I were isolated from the fermentation of marine fungus Scopulariopsis sp.(TA01-33) by means of column chromatography, such as positive phase silica gel column chromatography, etc. Alkaloids with formula II, III, IV and V were semisynthesized from compounds with formula I.

Claims

1. A method of treating an infection of Herpes Simplex Virus 1 (HSV-1), comprising administering to a subject in need thereof an effective amount of a compound, or pharmaceutically acceptable salts thereof, having a structure of

2. The method of claim 1, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula I,

3. The method of claim 1, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula II,

4. The method of claim 1, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula III,

5. The method of claim 1, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula IV,

6. The method of claim 1, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula V,

12. The method of claim 1, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula V,

7. A method of inhibiting activities of herpes simplex virus 1 (HSV-1), comprising the step of contacting a cell with a compound, or pharmaceutically acceptable salts thereof, having a structure of

8. The method of claim 7, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula I,

9. The method of claim 7, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula II,

10. The method of claim 7, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula III,

11. The method of claim 7, wherein the compound, or pharmaceutically acceptable salts thereof, has a structure of the following formula IV,