Compounds, compositions and associated methods comprising 3-aryl quinolines

Patent metadata

Field	Value
Publication number	US-10023538-B2
Application number	US-201715440458-A
Country	US
Kind code	B2
Filing date	Feb 23, 2017
Priority date	Jan 13, 2012
Publication date	Jul 17, 2018
Grant date	Jul 17, 2018

Abstract

Compounds, compositions and methods useful for treating infectious diseases are provided. In particular, 3-aryl quinoline compounds, their synthesis, pharmaceutical compositions thereof and methods of treating infectious diseases such as malaria, are disclosed.

First claim

The invention claimed is:

1. A compound with the structure of Formula (II)

wherein X 1 , X 2 , X 3 , X 4 , and X 5 are independently selected from of H, halo, alkoxy, ether, alkyl, substituted alkyl, alkyl ether, haloalkyl, haloalkyl ether, aryl, substituted aryl, aryl ether, substituted aryl ether, aryl amine, 5-member heterocycle, 6-member heterocycle, amino, benzylic amide, cyano, morpholinyl, N-ethyl morpholinyl, or carboxyl; and
R 1 is selected from N—N-diethylpropanamino, N-isobutylpropanamino, N-isobutylpropanamino, N—N-diethylpropanamino, and 2-(2-piperidinyl) ethyl; or R 1 is N—N-diethyl-(4-methyl) butanamino and X 3 is OCF 3 .

2. The compound of claim 1 wherein the compound has a structure selected from:

3. A pharmaceutical composition comprising an effective amount of the compound of claim 1 .

4. A method of treating a parasitic infection in a subject, the method comprising: administering a therapeutically effective amount of the pharmaceutical composition of claim 3 to the subject.

5. The method of claim 4 wherein the pharmaceutical composition is administered orally, subcutaneously, intravenously or intramuscularly.

6. The method of claim 4 wherein the parasitic infection is a Plasmodium infection.

7. The method of claim 6 wherein the Plasmodium infection comprises an infection with a plasmodium strain resistant to one or more of the following classes of compounds: quinine, mefloquine, chloroquine, or atovaquone.

8. The method of claim 6 wherein the Plasmodium strain is selected from P. falciparum and P. vivax.

9. The compound of claim 1 , wherein X 1 , X 2 , X 4 , and X 5 are H and X 3 is OCF 3 .

Assignees

• Univ Oregon Health & Science
• Us Veterans Affairs
• Univ Oregon Health & Science

Inventors

• Riscoe Michael K
• Winter Rolf W
• Pou Sovitj
• Hinrichs David J
• Kelly Jane Xu
• Li Yuexin
• Nilsen Aaron

Classifications

• A61P33/06

  Antimalarials · CPC title

• A61K31/47

  Quinolines; Isoquinolines · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D215/46 Primary

  with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms · CPC title

• Y02A50/30

  Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change · CPC title