Substituted phenylpyrrolecarboxamides with therapeutic activity in HIV

Patent metadata

Field	Value
Publication number	US-10137107-B2
Application number	US-201515512493-A
Country	US
Kind code	B2
Filing date	Sep 18, 2015
Priority date	Sep 19, 2014
Publication date	Nov 27, 2018
Grant date	Nov 27, 2018

Abstract

Substituted phenylpyrrolecarboxamide compounds such as those represented by Formula A can be used in the treatment of HIV infection and related conditions.

First claim

What is claimed is:

1. A compound represented by Formula 1:

wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , and R 14 are H, a halide, or a substituent having a molecular weight of 15 Da to 150 Da and consisting of 2 to 5 chemical elements, wherein the chemical elements are independently C, H, O, N, S, P, F, Cl, Br, or I;
R 11 is H, optionally substituted C 1-6 alkyl, the optional substituent having a molecular weight of 15 Da to 150 Da and consisting of 2 to 5 chemical elements, wherein the chemical elements are independently C, H, O, N, S, P, F, Cl, Br, or I;
R 15 , and R 15a are H, optionally substituted C 1-6 alkyl, optionally substituted carbamimidoyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl, the optional substituent having a molecular weight of 15 Da to 150 Da and consisting of 2 to 5 chemical elements, wherein the chemical elements are independently C, H, O, N, S, P, F, Cl, Br, or I;
R 16 is H or C 1-6 hydrocarbyl; and
Y is a bond or C 1-3 alkyl.

2. The compound of claim 1 , wherein Y—N(R 15 , R 15a ) is —CH 2 NH 2 .

3. The compound of claim 1 , wherein Y—N(R 15 , R 15a ) is —CH 2 CH 2 NH 2 .

4. The compound of claim 1 , wherein Y—N(R 15 , R 15a ) is —CH 2 NHCH 3 .

5. The compound of claim 1 , wherein [Y—N(R 15 , R 15a ) is —CH 2 N(CH 3 ) 2 .

6. The compound of claim 1 , wherein Y—N(R 15 , R 15a ) is —CH 2 CH 2 N(CH 3 ) 2 .

7. The compound of claim 1 , wherein Y—N(R 15 , R 15a ) is —CH 2 CH 2 NHCH 3 .

8. A compound represented by a formula:

9. A method of treating HIV infection comprising administering a compound according to claim 1 to a human being infected with HIV virus.

10. The compound of claim 1 , wherein Y—N(R 15 , R 15a ) is:

wherein n is 0, 1, or 3.

11. The compound of claim 1 , wherein R 11 is H.

12. The compound of claim 1 , wherein R 6 is a halide.

13. The compound of claim 1 , wherein R 6 is CH 3 .

14. The compound of claim 1 , wherein R 5 or R 7 is a halide.

15. The compound of claim 14 , wherein R 5 or R 7 is F.

16. The compound of claim 1 , wherein R 13 is —(CH 2 ) n OH, wherein n is 1, 2, or 3.

17. The compound of claim 1 , wherein R 14 is CH 3 or H.

18. The compound of claim 1 , wherein R 15 and R 15a are, independently, H, CH 3 , or carbamimidoyl.

Assignees

• New York Blood Center Inc
• Us Health
• Nat Institutes Of Health

Inventors

• Debnath Asim Kumar
• Curreli Francesca
• Kwong Peter D
• Kwon Young Do

Classifications

• A61P31/18

  for HIV · CPC title

• A61K31/40 Primary

  having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil · CPC title

• C07D207/30

  having two double bonds between ring members or between ring members and non-ring members · CPC title

• C07C233/01

  having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07D403/12

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