# US 11,028,096 B2 · Tricyclic P2-ligand containing potent HIV-protease inhibitors against HIV/AIDS

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- Number: US 11,028,096 B2
- Document ID: US11028096B2
- Status: Granted
- Kind: B2
- Application number: 16/348,558
- Filed: 2017-11-09
- Published: 2019-11-28
- Granted: 2021-06-08
- Earliest claimed: 2016-11-09
- Assignees: Purdue Research Foundation
- Applicants: Purdue Research Foundation
- Inventors: Arun K. Ghosh; Hiroaki Mitsuya; Prasanth Reddy Nyalapatla
- Web page: https://patentgrep.com/patent/US11028096B2

## CPC

- C07D 493/04: Ortho-condensed systems
- C07D 493/06: Peri-condensed systems
- A61P 31/18: for HIV
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 307/77: ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D 311/78: Ring systems having three or more relevant rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Various embodiments relate to a compound of the formula (I) and (II), wherein X, X1, X2, X3, and R1-R4 are defined herein, as well as pharmaceutical compositions comprising compounds of the formula (I) and/or (II) and methods of treating an HIV infection comprising administering a therapeutically effective amount of one or more compounds of formula (I) and/or (II), or a pharmaceutical composition comprising compounds of the formula (I) and/or (II), to a patient in need thereof.

## Claims

### Claim 1

A compound of the formula (I)
or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein: n is an integer from 0 to 3; X is (—CHR5—)m or —O—, wherein m is 1 or 2 and each R5 is, independently H, alkyl or alkoxy;
X1, X2, and X3 are each, independently, (—CHR5—)m;
R1 is alkyl, alkoxy, aryl, heterocycyl, halo, hydroxy or amino;
R2 is alkyl;
R3 is aryl, benzthiazole, benzoxazole, benzofuranyl or indolyl; and
R4 is H, alkyl or alkoxy.

### Claim 2 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein:
X1 is (—CHR5—)m, wherein m is 2;
X2 is (—CHR5—)m, wherein m is 1;
X3 is (—CHR5—)m, wherein m is 1; and
wherein each R5 is independently H, alkyl or alkoxy.

### Claim 3 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein:
X1 is (—CHR5—)m, wherein m is 1;
X2 is (—CHR5—)m, wherein m is 1;
X3 is (—CHR5—)m, wherein m is 2; and
wherein each R5 is independently H, alkyl or alkoxy.

### Claim 4 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein X is O.

### Claim 5 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein X is (—CHR5—)m, wherein m is 1 and R5 is H, alkyl or alkoxy.

### Claim 6 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein R4 can be H or alkoxy.

### Claim 7 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein the compound of the formula (I) is a compound of the formula:
or a pharmaceutically acceptable salt, polymorph, prodrug, solvate or clathrate thereof, wherein n, R1, R2, R3, and R4 are as defined in claim 1.

### Claim 8 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein n is 0.

### Claim 9 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein R2 is unsubstituted alkyl.

### Claim 10 (depends on 1)

The compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein R3 is aryl, benzthiazole or benzoxazole.

### Claim 11 (depends on 10)

The compound of claim 10, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein R3 is phenyl.

### Claim 12 (depends on 10)

The compound of claim 10, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein R3 is:

### Claim 13 (depends on 12)

The compound of claim 12, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein R3 is:

### Claim 14 (depends on 10)

The compound of claim 10, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, wherein R3 is:
wherein R6 is alkyl, alkylamino, cycloalkylamino, cycloalkyl heterocycloamino, heterocyclo cycloalkylamino or heterocycloamino; and
X4 is S, O or NR7, wherein R7 is H, alklyl, cycloalkyl or alkylaryl.

### Claim 15 (depends on 1)

The compound of claim 1, wherein the compound is:
or a pharmaceutically acceptable salt, polymorph, or solvate thereof.

### Claim 16 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, or a pharmaceutically acceptable salt, polymorph, or solvate thereof, and one or more pharmaceutically acceptable excipients.