3-amidobenzamides and uses thereof for increasing cellular levels of A3G and other A3 family members

Patent metadata

Field	Value
Publication number	US-9688637-B2
Application number	US-201514832508-A
Country	US
Kind code	B2
Filing date	Aug 21, 2015
Priority date	Aug 21, 2014
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

Disclosed are novel benzamide compounds and the uses thereof for treating diseases and disorders in a patient in need thereof by increasing cellular levels of A3G and/or other members of the A3 family of proteins in the patient. The disclosed compounds include 3-benzamide compounds that may be administered treat an HIV-1 infection or cancer in a patient.

First claim

We claim:

1. A compound having a formula:

wherein:
n is 0 or 1;
R 1 is hydroxyl, C1-C6-alkoxy, or

 wherein
R 8 is C1-C6-alkyl,

R 9 is H, or C1-C6-alkyl;
R 11 is H, C3-C6-alkyl optionally substituted with C1-C6-alkoxy, hydroxyl, C1-C6-alkylamino, C1-C6-dialkyl amino, phenyl, benzyl, benzo[1,3]diox-8-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, C3-C6-cycloalkyl optionally substituted with methyl, C1-C6-alkoxy, N-piperidinyl, tetrahydrofuran-2-yl, adamantan-7-yl, or

 wherein
R 12 and R 13 are independently selected from 4 C1-C6-alkyl optionally substituted with C1-C6-alkoxy, C1-C6-alkoxy, C1-C6 cycloalkyl, phenyl, C1-C6-alkylamino, C1-C6-dialkyl amino, or R 12 and R 13 together form a C3-C6 homocycle or a C3-C6 heterocycle, which optionally is unsaturated at one or more bonds;
R 14 is H or C1-C6-alkyl;
R 5 is halo; and
R 6 is halo.

2. The compound of claim 1 , wherein n is 0.

3. The compound of claim 1 , wherein R 1 is methoxy.

4. The compound of claim 1 , having a formula:

5. The compound of claim 4 , wherein R 1 is C1-C6-alkoxy.

6. The compound of claim 4 , wherein R 11 is H, C3-C6-alkyl optionally substituted with C1-C6-alkoxy, hydroxyl, C1-C6-alkylamino, C1-C6 dialkylamino, phenyl, benzyl, benzo[1,3]diox-8-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, C3-C6-cycloalkyl optionally substituted with methyl, C1-C6-alkoxy, N-piperidinyl, and tetrahydrofuran-2-yl.

7. The compound of claim 1 , wherein one or both of R 5 and R 6 are chloro.

8. The compound of claim 1 having a formula:

9. A compound having a formula selected from:

10. The compound of claim 9 having a formula:

11. The compound of claim 9 having a formula:

12. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutical carrier.

13. A pharmaceutical composition comprising the compound of claim 9 and a pharmaceutical carrier.

Assignees

• Univ Northwestern
• Northwestern Universtiy

Inventors

• Schiltz Gary E
• Song Chisu
• D'Aquila Richard T
• Roh Meejeon

Classifications

• C07D213/75

  Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates · CPC title

• C07C311/08

  having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• A61P31/18

  for HIV · CPC title

• C07C2601/04

  with a four-membered ring · CPC title