# US 10,869,856 B2 · Substituted phenylpyrrolecarboxamides with therapeutic activity in HIV

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- Number: US 10,869,856 B2
- Document ID: US10869856B2
- Status: Granted
- Kind: B2
- Application number: 16/777,559
- Filed: 2020-01-30
- Published: 2020-05-28
- Granted: 2020-12-22
- Earliest claimed: 2014-09-19
- Assignees: New York Blood Center, Inc.; The United States of America, as represented by the Secretary, Department of Health and Human Services
- Applicants: New York Blood Center, Inc.; The United States of America, as Represented by the Secretary, Department of Health and Human Services
- Inventors: Asim Kumar Debnath; Francesca Curreli; Peter D. Kwong; Young Do Kwon
- Web page: https://patentgrep.com/patent/US10869856B2

## CPC

- A61K 31/40: having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61P 31/18: for HIV
- C07C 25/00: Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C 233/01: having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07D 207/30: having two double bonds between ring members or between ring members and non-ring members
- C07D 207/34: 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
- C07D 241/04: having no double bonds between ring members or between ring members and non-ring members
- C07D 277/20: having two or three double bonds between ring members or between ring members and non-ring members
- C07D 401/14: containing three or more hetero rings
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 405/14: containing three or more hetero rings
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D 417/14: containing three or more hetero rings
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

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

## Claims

### Claim 1

A compound represented by Formula 1:
wherein R4, R5, R6, R7, R8, R9, R10, R12, R13, and R14 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;
R11, R15, and R15a are independently H, optionally substituted C1-6 alkyl, optionally substituted carbamimidoyl, optionally substituted C1-6 aryl, or optionally substituted C1-6 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;
R16 is H or C1-6 hydrocarbyl; and
Y is a bond or C1-3 alkyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R11, R15, and R15a are independently H, C1-6 alkyl, carbamimidoyl, C1-6 aryl, or C1-6 heteroaryl.

### Claim 3 (depends on 2)

The compound of claim 2, wherein R4, R5, R7, and R8 are H, F, Cl, NH2, CH3, SO2NH2, OCH3, CH2OH, or N(C2H5)2;
wherein R6 is H, F, Cl, CN, CH3, CF3, OH, NH2, C1-6 alkyl or C1-6 alkoxy;
wherein R9, R10, and R11 are independently H or CH3;
wherein R13 and R14 are independently H, F, Cl, NH2, CH3, SO2NH2, OCH3, CH2OH, or N(C2H5)2;
wherein R15 and R15a are independently H, F, Cl, NH2, CH3, SO2NH2, OCH3, CH2OH, or N(C2H5)2;
wherein R16 is H or CH3;
and wherein Y is C1-3 hydrocarbyl.

### Claim 4 (depends on 3)

The compound of claim 3, wherein R9 and R11 are H.

### Claim 5 (depends on 3)

The compound of claim 3, wherein R6 is CF3 or CH3.

### Claim 6 (depends on 3)

The compound of claim 3, wherein R5 and R7 are independently F or H.

### Claim 7 (depends on 3)

The compound of claim 3, wherein R13 and R14 are independently H or CH2OH.

### Claim 8 (depends on 3)

The compound of claim 3, wherein R4 and R8 are H.

### Claim 9 (depends on 3)

The compound of claim 3, having the structure:

### Claim 10 (depends on 9)

The compound of claim 9, consisting of one stereoisomer.

### Claim 11 (depends on 3)

The compound of claim 3, having the structure:

### Claim 12 (depends on 11)

The compound of claim 11, consisting of one stereoisomer.