Substituted phenylpyrrolecarboxamides with therapeutic activity in HIV

Patent metadata

Field	Value
Publication number	US-10869856-B2
Application number	US-202016777559-A
Country	US
Kind code	B2
Filing date	Jan 30, 2020
Priority date	Sep 19, 2014
Publication date	Dec 22, 2020
Grant date	Dec 22, 2020

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

The invention 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 independently 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 , R 15 , and R 15a are independently 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 R 11 , R 15 , and R 15a are independently H, C 1-6 alkyl, carbamimidoyl, C 1-6 aryl, or C 1-6 heteroaryl.

3. The compound of claim 2 , wherein R 4 , R 5 , R 7 , and R 8 are H, F, Cl, NH 2 , CH 3 , SO 2 NH 2 , OCH 3 , CH 2 OH, or N(C 2 H 5 ) 2 ;
wherein R 6 is H, F, Cl, CN, CH 3 , CF 3 , OH, NH 2 , C 1-6 alkyl or C 1-6 alkoxy;
wherein R 9 , R 10 , and R 11 are independently H or CH 3 ;
wherein R 13 and R 14 are independently H, F, Cl, NH 2 , CH 3 , SO 2 NH 2 , OCH 3 , CH 2 OH, or N(C 2 H 5 ) 2 ;
wherein R 15 and R 15a are independently H, F, Cl, NH 2 , CH 3 , SO 2 NH 2 , OCH 3 , CH 2 OH, or N(C 2 H 5 ) 2 ;
wherein R 16 is H or CH 3 ;
and wherein Y is C 1-3 hydrocarbyl.

4. The compound of claim 3 , wherein R 9 and R 11 are H.

5. The compound of claim 3 , wherein R 6 is CF 3 or CH 3 .

6. The compound of claim 3 , wherein R 5 and R 7 are independently F or H.

7. The compound of claim 3 , wherein R 13 and R 14 are independently H or CH 2 OH.

8. The compound of claim 3 , wherein R 4 and R 8 are H.

9. The compound of claim 3 , having the structure:

10. The compound of claim 9 , consisting of one stereoisomer.

11. The compound of claim 3 , having the structure:

12. The compound of claim 11 , consisting of one stereoisomer.

Assignees

• New York Blood Center Inc
• Us Health

Inventors

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

Classifications

• C07D413/12

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

• C07D401/14

  containing three or more hetero rings · CPC title

• C07D241/04

  having no double bonds between ring members or between ring members and non-ring members · CPC title

• C07D277/20

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

• C07D403/12

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