# US 11,078,159 B2 · Compounds and methods for inhibiting EMT pathways to treat cancer, organ fibrosis and metabolic disorders

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- Number: US 11,078,159 B2
- Document ID: US11078159B2
- Status: Granted
- Kind: B2
- Application number: 16/487,770
- Filed: 2018-02-19
- Published: 2019-12-12
- Granted: 2021-08-03
- Earliest claimed: 2017-02-22
- Assignees: University of Pittsburgh—Of the Commonwealth System of Higher Education; Universite Le Havre Normandie
- Applicants: University of Pittsburgh—Of the Commonwealth System of Higher Education; Universite Le Havre Normandie
- Inventors: Abdelhadi Rebbaa; Sebastien Comesse; Adam Daich; Martin Lawson; Catalin Pintiala
- Web page: https://patentgrep.com/patent/US11078159B2

## CPC

- A61P 3/08: for glucose homeostasis (pancreatic hormones A61P5/48)
- C07D 213/02: having three double bonds between ring members or between ring members and non-ring members
- A61K 31/4412: having oxo groups directly attached to the heterocyclic ring
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 213/80: in position 3
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 405/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 409/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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

A compound, or a pharmaceutically acceptable salt or isomer thereof, of Formula I: wherein R is hydrogen, alkyl, substituted alkyl, alkenyl, or substituted alkenyl; R1 is hydrogen, alkoxy, or substituted alkoxy; R2 is hydrogen, alkyl, or substituted alkyl; and R3 is hydrogen, alkyl, or substituted alkyl.

## Claims

### Claim 1

A compound, or a pharmaceutically acceptable salt or stereoisomer thereof, of Formula I:
wherein R is —(CH2)a—Ar, wherein a is 1 to 6 and Ar is an aryl, substituted aryl, heteroaryl or substituted heteroaryl;
R1 is hydrogen, alkoxy, or substituted alkoxy;
R2 is alkyl or substituted alkyl; and
R3 is hydrogen, alkyl, or substituted alkyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Ar is phenyl or substituted phenyl.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R is benzyl or substituted benzyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R is benzyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R1 is hydrogen.

### Claim 6 (depends on 1)

The compound of claim 1, wherein R2 is C1-C6 alkyl.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R3 is C1-C6 alkyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R3 is ethyl.

### Claim 9 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, and a pharmaceutically acceptable excipient.

### Claim 10 (depends on 1)

The compound of claim 1, wherein the compound is:

### Claim 11 (depends on 4)

The compound of claim 4, wherein R2 is C1-C6 alkyl.

### Claim 12 (depends on 11)

The compound of claim 11, wherein R3 is ethyl.

### Claim 13 (depends on 8)

The compound of claim 8, wherein R2 is C1-C6 alkyl.

### Claim 14 (depends on 13)

The compound of claim 13, wherein R3 is ethyl.

### Claim 15 (depends on 1)

The compound of claim 1, wherein R2 is alkyl.

### Claim 16 (depends on 1)

The compound of claim 1, wherein R3 is alkyl or substituted alkyl.

### Claim 17 (depends on 16)

The compound of claim 16, wherein R2 is alkyl or substituted alkyl.

### Claim 18 (depends on 1)

The compound of claim 1, wherein R2 is pentyl.

### Claim 19 (depends on 2)

The compound of claim 2, wherein R2 is pentyl.