Amine compounds having anti-inflammatory, antifungal, antiparasitic, and anticancer activity

1. A compound represented by Formula IA1a or a pharmaceutically acceptable salt thereof

wherein n is 2, 3, 4, 5, 6, 7, or 8;

p is 1;

q is 0 or 1;

R 1 is hydrogen and R 2 is hydrogen;

R 4 is hydrogen; and

R 5 is selected from the group consisting of halo; alkoxy having from 1 to 10 carbon atoms unsubstituted or substituted by phenyl or phenoxy, provided that when substituted by phenoxy the alkoxy must have more than one carbon atom; phenyl; phenoxy; C(O)OR 6 ; C(O)NHR 6 ; or NHC(O)R 6 , wherein R 6 is alkyl having from 1 to 6 carbon atoms.

2. The compound or salt of claim 1 , wherein q is 0, and R 5 is alkoxy having from 1 to 6 carbon atoms unsubstituted or substituted by phenyl.

3. The compound or salt of claim 2 , wherein R 5 is in the ortho position.

4. The compound or salt of claim 3 , wherein the compound is selected from the group consisting of:

N-{2-[2-(Hexyloxy)phenoxy]ethyl}quinolin-4-amine,

N-{3-[2-(Hexyloxy)phenoxy]propyl}quinolin-4-amine,

N-{4-[2-(Hexyloxy)phenoxy]butyl}quinolin-4-amine,

N-[3-(2-Ethoxyphenoxy)propyl]quinolin-4-amine,

N-[3-(2-Methoxyphenoxy)propyl]quinolin-4-amine, and

N-{3-[2-(Benyloxy)phenoxy]propyl}quinolin-4-amine.

5. The compound or salt of claim 2 , wherein R 5 is in the meta position.

6. The compound or salt of claim 5 , wherein the compound is selected from the group consisting of:

N-[8-(3-Methoxyphenoxy)octyl]quinolin-4-amine,

N-{4-[3-(Hexyloxy)phenoxy]butyl}quinolin-4-amine,

N-{3-[3-(Hexyloxy)phenoxy]propyl}quinolin-4-amine, and

N-{2-[3-(Hexyloxy)phenoxy]ethyl}quinolin-4-amine.

7. The compound or salt of claim 2 , wherein R 5 is in the para position.

8. The compound or salt of claim 7 , wherein the compound is selected from the group consisting of:

N-[8-(4-Methoxyphenoxy)octyl]quinolin-4-amine,

N-[6-(4-Methoxyphenoxy)hexyl]quinolin-4-amine,

N-{2-[4-(Hexyloxy)phenoxy]ethyl}quinolin-4-amine,

N-{3-[4-(Hexyloxy)phenoxy]propyl}quinolin-4-amine, and

N-{4-[4-(Hexyloxy)phenoxy]butyl}quinolin-4-amine.

9. The compound or salt of claim 1 , wherein R 5 is fluoro.

10. The compound or salt of claim 9 , wherein the compound is selected from the group consisting of:

N-[8-(4-Fluorophenoxy)octyl]quinolin-4-amine,

N-[8-(3-Fluorophenoxy)octyl]quinolin-4-amine, and

N-[8-(2-Fluorophenoxy)octyl]quinolin-4-amine.

11. A compound represented by Formula IA1a or a pharmaceutically acceptable salt thereof

wherein n is 0;

p is 0;

q is 1;

R 1 is hydrogen and R 2 is hydrogen;

R 4 is hydrogen or halo; and

R 5 is alkoxy having from 1 to 10 carbon atoms, phenoxy, or alkoxy having from 1 to 10 carbon atoms substituted by phenyl.

12. The compound of claim 11 , wherein R 5 is alkoxy having from 1 to 10 carbon atoms.

13. The compound or salt of claim 12 , wherein the compound is selected from the group consisting of:

N-[4-(Hexyloxy)benzyl]quinolin-4-amine,

N-[2-(Hexyloxy)benzyl]quinolin-4-amine,

N-[3-Fluoro-4-(hexyloxy)benzyl]quinolin-4-amine,

N-[4-(Decyloxy)benzyl]quinolin-4-amine, and

N-[3-(Decyloxy)benzyl]quinolin-4-amine.

14. The compound of claim 11 , wherein R 5 is phenoxy, or alkoxy having from 1 to 10 carbon atoms substituted by phenyl.

15. The compound or salt of claim 14 , wherein the compound is selected from the group consisting of:

N-[3-(Benzyloxy)benzyl]quinolin-4-amine, and

N-(3-Phenethoxybenzyl)quinolin-4-amine.

16. N-[3-(Hexyloxy)benzyl]quinolin-4-amine or a pharmaceutically acceptable salt thereof.

17. N-(3-Phenoxybenzyl)quinolin-4-amine or a pharmaceutically acceptable salt thereof.