Anti-HIV compound and preparation method and use thereof

Patent metadata

Field	Value
Publication number	US-9402819-B2
Application number	US-201314647159-A
Country	US
Kind code	B2
Filing date	Dec 13, 2013
Priority date	Dec 28, 2011
Publication date	Aug 2, 2016
Grant date	Aug 2, 2016

Abstract

The present invention relates to the technical field of chemically synthesized drugs, in particular to an anti-HIV drug or prodrug and preparation method and uses thereof. The compound or prodrug compound of the present invention has a structural formula as represented by formula I. The compounds have anti-HIV-1 and anti-HIV-2 virus activity, and have a C8166 therapeutic index as high as 2081.59 and an H9 therapeutic index as high as 303.03. Furthermore, the compounds have high solubility up to 1290-2845.5 μg/ml in an aqueous solution, and can be formulated into an oral formulation.

First claim

The invention claimed is:

1. An anti-HIV compound represented by the following formula

wherein:
R 5 is a straight chain or branched C 1-8 alkoxy group;
X is S or SO 2 ; and
R 16 is H or

 where R 20 is at least one amino acid selected from the group consisting of Ala, Arg, Asn, Asp, Cys, Glu, Gln, Gly, His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr and Val, provided that the at least one amino acid that is directly connected to the carbonyl group of R 16 is free of an α-C carboxyl group.

2. The compound according to claim 1 , wherein R 16 is H.

3. The compound according to claim 2 , wherein R 5 is a C 1-4 alkoxy group.

4. The compound according to claim 3 , wherein R 5 is a C 1-2 alkoxy group.

5. The compound according to claim 3 , wherein R 5 is methoxyl.

6. The compound according to claim 1 having a structure selected from the group consisting of:

7. A pharmaceutically acceptable salt of a compound according to claim 1 , wherein the salt is a hydrochloride, sulfate, phosphate or nitrate salt.

8. The pharmaceutically acceptable salt according to claim 7 , which is the hydrochloride salt.

9. A method for treating HIV, said method comprising administering to a patient a compound according to claim 1 .

10. The method of claim 9 , wherein the compound is effective for treating at least one of HIV-1 and HIV-2 infection.

Assignees

• Univ Sichuan

Inventors

• Li Rui
• Wei Yuquan

Classifications

• C07C237/44

  having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring · CPC title

• A61K31/255

  of sulfoxy acids or sulfur analogues thereof · CPC title

• C07C317/48

  the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups · CPC title

• A61K31/167 Primary

  having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol · CPC title

• A61P31/18

  for HIV · CPC title