Oligo-benzamide compounds and their use in treating cancers

Patent metadata

Field	Value
Publication number	US-9458095-B2
Application number	US-201514792072-A
Country	US
Kind code	B2
Filing date	Jul 6, 2015
Priority date	Nov 23, 2011
Publication date	Oct 4, 2016
Grant date	Oct 4, 2016

Abstract

The present invention includes bis- and tris-benzamide compounds that block AR signaling and have activity against prostate cancer. Uses for these compounds, and pharmaceutical compositions containing the same, also are provided.

First claim

What is claimed:

1. A compound of formula (I or II):

wherein:
R 1 , R 2 and R 3 are each independently optionally substituted C 1 -C 10 alkyl or C 1 -C 15 arylalkyl;
X is —NO 2 or —NRCOR′, wherein R′ is C1-C15 arylalkyl;
Y is —COOR 4 or —CONR 4 R 5 ;
R 4 and R 5 are independently selected from —H or C 1 -C 10 alkyl; and
A, A′ and A″ are independently —O—, —S—, —NR—, —(CH 2 )n-, —CO— wherein n may be any number between 1-6.

2. The compound of claim 1 , wherein X is —NO 2 .

3. The compound of claim 2 , wherein A, A′ and A″ are each O.

4. The compound of claim 1 , wherein R 1 is C 1-10 hydroxyalkyl.

5. The compound of claim 1 , wherein R 1 is C 1 -C 15 arylalkyl.

6. The compound of claim 1 , wherein R 2 is C 1-10 alkyl.

7. The compound of claim 1 , wherein R 3 is C 1-10 alkyl.

8. A pharmaceutical composition comprising a compound as shown in claim 1 , dispersed in a pharmaceutically acceptable carrier, buffer or diluent.

9. The compound of claim 4 , wherein R 1 is 2-hydroxyethyl.

10. The compound of claim 5 , wherein R 1 is 2-quinolylethyl.

11. The compound of claim 6 , wherein R 2 is butyl.

12. The compound of claim 6 , wherein R 2 is isobutyl.

13. The compound of claim 7 , wherein R 3 is isobutyl.

14. The compound of claim 1 , wherein X is —NHCOR′ wherein: R′ is C 1 -C 15 arylalkyl.

15. The compound of claim 1 , wherein Y is —COOH.

16. The compound of claim 1 , wherein Y is —CONHR 5 , wherein: R 5 is —H or C 1 -C 10 alkyl.

17. The compound of claim 1 , wherein the compound is further defined as:

18. The compound of claim 1 , wherein the compound is further defined as:

19. The pharmaceutical composition of claim 8 , wherein the compound is further defined as:

20. The pharmaceutical composition of claim 8 , wherein the compound is further defined as:

Assignees

• Univ Texas
• Univ Texas

Inventors

• Ahn Jung-Mo
• Raj Ganesh

Classifications

• C07C237/44 Primary

  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

• A61K31/365

  Lactones · CPC title

• A61K31/167

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

• A61N5/10

  X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy (A61N5/01 takes precedence) · CPC title

• C07C235/56

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