# US 10,501,420 B2 · Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole

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- Number: US 10,501,420 B2
- Document ID: US10501420B2
- Status: Granted
- Kind: B2
- Application number: 16/230,462
- Filed: 2018-12-21
- Published: 2019-05-09
- Granted: 2019-12-10
- Earliest claimed: 2014-08-26
- Assignees: Trustees of Dartmouth College
- Applicants: Trustees of Dartmouth College
- Inventors: Gordon W. Gribble; Michael B. Sporn; Karen T. Liby; Evans O. Onyango; Martine Cao
- Web page: https://patentgrep.com/patent/US10501420B2

## CPC

- C07D 233/60: with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
- A61K 31/4164: 1,3-Diazoles
- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)

## Abstract

Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl) imidazole and pharmaceutical compositions containing the same are provided.

## Claims

### Claim 1

A triterpenoid compound having the structure of Formula I, or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof:
wherein one or more of R1, R2 or R3 is independently a substituted or unsubstituted heteroaryl group and the remaining R groups are hydrogen.

### Claim 2 (depends on 1)

The triterpenoid compound of claim 1 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof, wherein R2 is a substituted or unsubstituted heteroaryl group and R1 and R3 are hydrogen.

### Claim 3 (depends on 1)

The triterpenoid compound of claim 1 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof, wherein the substituted or unsubstituted heteroaryl group is a substituted or unsubstituted pyridyl group.

### Claim 4 (depends on 1)

The triterpenoid compound of claim 1 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof, wherein R2 is a substituted or unsubstituted pyridyl group and R1 and R3 are hydrogen.

### Claim 5 (depends on 1)

The triterpenoid compound of claim 1 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof, wherein R2 is an unsubstituted pyridyl group and R1 and R3 are hydrogen.

### Claim 6 (depends on 1)

The triterpenoid compound of claim 1 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 7 (depends on 5)

A method of treating disorder characterized by overexpression of iNOS or COX-2 genes, the method comprising administering to a subject in need thereof a pharmaceutically effective amount of the triterpenoid compound of claim 5 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 7)

The method of claim 7, wherein the disorder is cancer.

### Claim 9 (depends on 5)

A pharmaceutical composition comprising the compound of claim 5 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable carrier.

### Claim 10

A compound or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof, wherein the compound is:

### Claim 11 (depends on 10)

The triterpenoid compound of claim 10 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 12 (depends on 10)

The triterpenoid compound of claim 10 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof, wherein the compound is

### Claim 13 (depends on 10)

A method of treating disorder characterized by overexpression of iNOS or COX-2 genes, the method comprising administering to a subject in need thereof a pharmaceutically effective amount of the triterpenoid compound of claim 10 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof.

### Claim 14 (depends on 13)

The method of claim 13, wherein the disorder is cancer.

### Claim 15 (depends on 13)

The method of claim 13, wherein the disorder is a leukemic cancer.

### Claim 16 (depends on 13)

The method of claim 13, wherein the disorder is a solid cancer.

### Claim 17 (depends on 10)

A pharmaceutical composition comprising the compound of claim 10 or a hydrate, stereoisomer, or pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable carrier.

### Claim 18

A compound of the formula:
or a pharmaceutically acceptable salt thereof.

### Claim 19 (depends on 18)

A method of treating a cancer characterized by overexpression of iNOS or COX-2 genes, the method comprising administering to a subject in need thereof a pharmaceutically effective amount of the compound of claim 18 or a pharmaceutically acceptable salt thereof.

### Claim 20 (depends on 18)

A pharmaceutical composition comprising the compound of claim 18 or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutically acceptable carrier.