# US 10,370,373 B2 · Antitumor derivatives for differentiation therapy

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- Number: US 10,370,373 B2
- Document ID: US10370373B2
- Status: Granted
- Kind: B2
- Application number: 15/915,444
- Filed: 2018-03-08
- Published: 2018-07-12
- Granted: 2019-08-06
- Earliest claimed: 2016-03-03
- Assignees: The Cleveland Clinic Foundation
- Applicants: The Cleveland Clinic Foundation
- Inventors: Yogenthiran Saunthararajah; Kwok Peng Ng; James G. Phillips; Babal Kant Jha; Anand Dev Tiwari
- Web page: https://patentgrep.com/patent/US10370373B2

## CPC

- C07D 471/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Imidazopyridine derivatives according to formula I are described wherein X is selected from CH, N, S, and O, Y is selected from S, CO, and O, R1 and optional R2 are independently selected from H, OH, substituted or unsubstituted C1-C6 alkyl, and substituted or unsubstituted C4-C6 cycloalkyl or cycloheteroalkyl, R3 is selected from H, OH, substituted or unsubstituted C1-C6 alkyl, and optional Z is selected from OH, NH2, NH(CO)R4, NH(SO2)R4, guanidine, alkylguanidine, and fluoroguanidine, R4 is polyethylene glycol or substituted or unsubstituted C1-C6 alkyl, and pharmaceutically acceptable salt thereof. The imidazopyridine derivatives can be used for treatment of cancer in a subject.

## Claims

### Claim 1

A compound of formula I
wherein X is selected from CH, N, S, and O, Y is selected from S, CO, NH, NO, and O,
R1 and optional R2 are independently selected from unsubstituted C4-C6 alkyl, unsubstituted C4-C6 cycloalkyl or cycloheteroalkyl, and aryl;
R3 is selected from H, OH, substituted or unsubstituted C1-C6 alkyl, and optional Z is selected from OH, NH2, NH(CO)R4, NH(SO2)R4, guanidine, alkylguanidine, and fluoroguanidine, R4 is polyethylene glycol or substituted or unsubstituted C1-C6 alkyl, and pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Y is O, R3 is C1-C6 alkyl, and Z is NH2.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the combined groups Y—R3—Z are CO2H, OH, or CHO.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Y is O, R3 is C1-C6 alkyl, and Z is NH2.

### Claim 5

A method of treating cancer in a subject in need thereof by administering a therapeutically effective amount of a compound of Formula I:
wherein X is selected from CH, N, S, and O, Y is selected from S, CO, NH, NO, and O,
R1 and optional R2 are independently selected from unsubstituted C4-C6 alkyl, unsubstituted C4-C6 cycloalkyl or cycloheteroalkyl, and aryl;
R3 is selected from H, OH, substituted or unsubstituted C1-C6 alkyl, and optional Z is selected from OH, NH2, NH(CO)R4, NH(SO2)R4, guanidine, alkylguanidine, and fluoroguanidine, R4 is polyethylene glycol or substituted or unsubstituted C1-C6 alkyl, and pharmaceutically acceptable salt thereof, and wherein the cancer is bladder cancer, prostate cancer, liver cancer, breast cancer, colon cancer, or leukemia.

### Claim 6 (depends on 5)

The method of claim 5, wherein Y is O, R3 is C1-C6 alkyl, and Z is NH2.

### Claim 7 (depends on 5)

The method of claim 5, wherein the combined groups Y—R3—Z are CO2H, OH, or CHO.

### Claim 8 (depends on 5)

The method of claim 5, wherein Y is O, R3 is C1-C6 alkyl, and Z is NH(CO)R4, NH(SO2)R4.

### Claim 9 (depends on 5)

The method of claim 5, wherein the compound of Formula I is administered together with a pharmaceutically acceptable carrier.

### Claim 10 (depends on 5)

The method of claim 5, wherein the cancer is acute myeloid leukemia.

### Claim 11 (depends on 5)

The method of claim 5, wherein the subject is human.

### Claim 12 (depends on 1)

The compound of claim 1, wherein R2 is unsubstituted C4-C6 alkyl, unsubstituted C4-C6 cycloalkyl or cycloheteroalkyl, or aryl.

### Claim 13 (depends on 1)

The compound of claim 1, wherein R2 is —H.