Substituted phenylpyrrolecarboxamides with therapeutic activity in HIV

Patent metadata

Field	Value
Publication number	US-11059808-B2
Application number	US-201615755009-A
Country	US
Kind code	B2
Filing date	Aug 23, 2016
Priority date	Sep 19, 2014
Publication date	Jul 13, 2021
Grant date	Jul 13, 2021

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:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , and R 11 are H;
R 5 is H or a halide;
R 6 is a halide, CH 3 , or OCH 3 ;
R 7 is hydrogen, halide, or OCH 3 ;
R 9 is hydrogen or OCH 3 ;
R 13 is CH 2 OH;
R 14 is H or CH 3 ;
R 15 , and R 15a are independently H or, C 1-6 alkyl;
R 16 is H; and
Y is C 1-3 alkyl.

2. A compound represented by:
A) Formula 2:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , 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;
R 16 is H or C 1-6 hydrocarbyl; and
Y is a bond, or C 1-3 alkylene; or

B) Formula 3:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 13 , R 14 , R 17 , R 18 , R 19 , R 20 , R 21 , and R 22 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 is H, optionally substituted C 1-6 alkyl, optionally substituted carbamimidoyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and

R 16 H or C 1-6 hydrocarbyl; or

C) Formula 4:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 17 , R 18 , R 19 , R 20 , R 21 , and R 23 are independently H, a halide, or a substituent haying 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, optionally substituted carbamimidoyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and
R 16 is H or C 1-6 hydrocarbyl;

D) Formula 5:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 23 , R 24 , R 25 , R 26 , R 28 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 is H, optionally substituted C 1-6 alkyl, optionally substituted carbamimidoyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and
R 16 is H or C 1-6 hydrocarbyl; or

E) Formula 6:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 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 is H, optionally substituted C 1-6 alkyl, optionally substituted carbamimidoyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and
R 16 is H or C 1-6 hydrocarbyl; or

F) Formula 7:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 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 is H, optionally substituted C 1-6 alkyl, optionally substituted carbamimidoyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and
R 16 is H or C 1-6 hydrocarbyl; or

G) Formula 8:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 23 , and R 26 are independently H, a halide, or a substituent haying 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, optionally substituted carbamimidoyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and
R 16 is H or C 1-6 hydrocarbyl; or

H) Formula 9:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 23 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 is H, optionally substituted C 1-6 alkyl, optionally substituted C 1-6 heteroalkyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and
R 16 is H or C 1-6 hydrocarbyl: or

I) Formula 10:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 23 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 is H, optionally substituted C 1-6 alkyl, optionally substituted C 1-6 heteroalkyl optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and
R 16 is H or C 1-6 hydrocarbyl; or

J) Formula 11:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently H, a halide, or a substituent haying 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;
wherein R 11 is H, optionally substituted C 1-6 alkyl, optionally substituted C 1-6 heteroalkyl, optionally substituted C 1-6 aryl, or optionally substituted C 1-6 heteroaryl; and
R 16 is H or C 1-6 hydrocarbyl; or

K) Formula 12:

or a pharmaceutically acceptable salt thereof,
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 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 chemi

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

• C07D207/34

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title

• A61P31/18

  for HIV · CPC title