Benzamide compounds

Patent metadata

Field	Value
Publication number	US-11318134-B2
Application number	US-201916957861-A
Country	US
Kind code	B2
Filing date	Jan 8, 2019
Priority date	Jan 10, 2018
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

Compounds of Formula (I) are provided herein. Such compounds, as well as pharmaceutically acceptable salts and compositions thereof, are useful for treating diseases or conditions, including conditions characterized by excessive cellular proliferation, such as cancer and tumors, as well as viral infections such as HIV.

First claim

What is claimed is:

1. A compound of Formula (I), or a pharmaceutically acceptable salt thereof, having the structure:

wherein:
R 1 is selected from the group consisting of hydrogen, halogen, a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl, a substituted or unsubstituted C 3 -C 6 cycloalkyl, a substituted or unsubstituted C 1 -C 6 alkoxy, an unsubstituted mono-C 1 -C 6 alkylamine and an unsubstituted di-C 1 -C 6 alkylamine;
each R 2 is independently selected from the group consisting of halogen, a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl and a substituted or unsubstituted C 3 -C 6 cycloalkyl; or
when m is 2 or 3, each R 2 is independently selected from the group consisting of halogen, a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl and a substituted or unsubstituted C 3 -C 6 cycloalkyl, or two R 2 groups taken together with the atom(s) to which they are attached form a substituted or unsubstituted C 3 -C 6 cycloalkyl or a substituted or unsubstituted 3 to 6 membered heterocyclyl;
R 3 is selected from the group consisting of X—R 3A

R 3A is a substituted or unsubstituted 5 to 10 membered heteroaryl;
R 4 is selected from the group consisting of NO 2 , S(O)R 6 , SO 2 R 6 , halogen, cyano and an unsubstituted C 1 -C 6 haloalkyl;
R 5 is selected from the group consisting of —X 1 -(Alk 1 ) n -R 7 and —X 2 (CHR 8 )-(Alk 2 ) p -X 3 —R 9 ;
Alk 1 and Alk 2 are independently selected from an unsubstituted C 1 -C 4 alkylene and a C 1 -C 4 alkylene substituted with 1, 2 or 3 substituents independently selected from fluoro, chloro, an unsubstituted C 1 -C 3 alkyl and an unsubstituted C 1 -C 3 haloalkyl;
R 6 is selected from the group consisting of a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl and a substituted or unsubstituted C 3 -C 6 cycloalkyl;
R 7 is selected from a substituted or unsubstituted C 1 -C 6 alkoxy, a substituted or unsubstituted C 3 -C 10 cycloalkyl, a substituted or unsubstituted 3 to 10 membered heterocyclyl, hydroxy, amino, a substituted or unsubstituted mono-substituted amine group, a substituted or unsubstituted di-substituted amine group, a substituted or unsubstituted N-carbamyl, a substituted or unsubstituted C-amido and a substituted or unsubstituted N-amido;
R 8 is selected from a substituted or unsubstituted 3 to 10 membered heterocyclyl(C 1 -C 6 alkyl), a substituted or unsubstituted di-C 1 -C 6 alkylamine(C 1 -C 6 alkyl) and a substituted or unsubstituted mono-C 1 -C 6 alkylamine(C 1 -C 6 alkyl);
R 9 is selected from a substituted or unsubstituted 5 to 10 membered heteroaryl and a substituted or unsubstituted C 6 -C 10 aryl;
m is 0, 1, 2 or 3;
n and p are independently selected from 0 and 1;
X 1 and X 2 are —NH—; and
X and X 3 are independently selected from the group consisting of —O—, —S— and —NH—.

2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is —CH 2 F or —CF 3 .

3. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is —CHF 2 .

4. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is not —CH 2 F, —CHF 2 or —CF 3 .

5. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 1.

6. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 2.

7. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 3.

8. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein one R 2 is an unsubstituted C 1 -C 6 alkyl and any other R 2 , if present, is independently selected from the group consisting of halogen, a substituted or unsubstituted C 1 -C 6 alkyl, a substituted or unsubstituted C 1 -C 6 haloalkyl and a substituted or unsubstituted C 3 -C 6 cycloalkyl.

9. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein each R 2 is independently an unsubstituted C 1 -C 6 alkyl.

10. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 2; and each R 2 is an unsubstituted methyl.

11. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein m is 0.

12. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein two R 2 groups taken together with the atom(s) to which they are attached form a substituted or unsubstituted C 3 -C 6 cycloalkyl.

13. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein two R 2 groups taken together with the atom to which they are attached form an unsubstituted cyclopropyl.

14. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein two R 2 groups taken together with the atom(s) to which they are attached form a substituted or unsubstituted 3 to 6 membered heterocyclyl.

15. The compound of claim 1 , that is also a compound of Formula (Ia), Formula (Ib), Formula (Ic) or Formula (Id):

or pharmaceutically acceptable salts of any of the foregoing.

16. The compound of claim 1 , wherein R 3 is X—R 3A .

17. The compound of claim 1 , wherein R 3A is

18. The compound of claim 1 , wherein R 3A is

19. The compound of claim 1 , wherein R 3A is a substituted 5 to 10 membered heteroaryl.

20. The compound of claim 1 , wherein X is —O—.

21. The compound of claim 1 , wherein X is —S—.

22. The compound of claim 1 , wherein X is —NH—.

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

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

25. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is NO 2 .

26. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein R 4 is cyano.

27. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is halogen.

28. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is an unsubstituted C 1 -C 6 haloalkyl.

29. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is —CF 3 .

30. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 4 is S(O)R 6 .

31. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein

Assignees

• Recurium Ip Holdings Llc

Inventors

• Pinchman Joseph Robert
• Huang Peter Qinhua
• Bunker Kevin Duane
• Sit Rakesh Kumar
• Samatar Ahmed Abdi

Classifications

• C07C47/42

  with a six-membered ring · CPC title

• C07C49/517

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61P31/18

  for HIV · CPC title

• C07D295/155

  with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings · CPC title