# US 2019/0375741 A1 · Quinoline oxadiazoles as cytoprotective agents

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- Number: US 2019/0375741 A1
- Document ID: US20190375741A1
- Status: Published application
- Kind: A1
- Application number: 16/436,846
- Filed: 2019-06-10
- Published: 2019-12-12
- Earliest claimed: 2015-11-28
- Inventors: Russell Dahl
- Web page: https://patentgrep.com/patent/US20190375741A1

## CPC

- C07D 413/14: containing three or more hetero rings
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 413/10: linked by a carbon chain containing aromatic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Provided herein are compounds of Formula I, pharmaceutical compositions thereof, and methods of their use for treating, preventing, or ameliorating one or more symptoms of a neurological disease, neurodegenerative disorder, or diabetes.

## Claims

### Claim 1

A compound of Formula I:
or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof; or a pharmaceutically acceptable salt, solvate, or hydrate thereof;
wherein:
R2 is methyl;
R3, R4, R5, R6, and R7 are each independently (a) hydrogen, cyano, or halo or (b) C1-6 alkyl, C3-10 cycloalkyl, or heterocyclyl with the proviso that R3 and R7 are not concurrently C1; and
R1 is aryl or heteroaryl.

### Claim 2 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R3, R4, R5, R6, and R7 are hydrogen.

### Claim 3 (depends on 1)

The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R1 is mono or disubstituted phenyl or 2-thienyl.

### Claim 4 (depends on 1)

The compound according to claim 1 selected from the group consisting of:

### Claim 5

A method for treating a neurological or neurodegenerative disorder in a subject comprising administering to the subject an effective amount of a compound of Formula I:
or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof; or a pharmaceutically acceptable salt, solvate, or hydrate thereof;
wherein:
R2 is methyl;
R3, R4, R5, R6, and R7 are each independently (a) hydrogen, cyano, or halo or (b) C1-6 alkyl, C3-10 cycloalkyl, or heterocyclyl with the proviso that R3 and R7 are not concurrently C1; and
R1 is aryl or heteroaryl.

### Claim 6

A method for treating, preventing, or ameliorating one or more symptoms of diabetes in a subject in need thereof comprising administering to the subject an effective amount of the compound Formula I:
or an enantiomer, a mixture of enantiomers, a mixture of two or more diastereomers, or an isotopic variant thereof; or a pharmaceutically acceptable salt, solvate, or hydrate thereof;
wherein:
R2 is methyl;
R3, R4, R5, R6, and R7 are each independently (a) hydrogen, cyano, or halo or (b) C1-6 alkyl, C3-10 cycloalkyl, or heterocyclyl with the proviso that R3 and R7 are not concurrently Cl; and
R1 is aryl or heteroaryl.

### Claim 7 (depends on 5)

The method of claim 5 wherein the neurological or neurodegenerative disorder is Alzheimer's disease.

### Claim 8 (depends on 5)

The method of claim 5 wherein the neurological or neurodegenerative disorder is Parkinson's disease.

### Claim 9 (depends on 6)

The method of claim 6 wherein the diabetes is type 1.

### Claim 10 (depends on 6)

The method of claim 6 wherein the diabetes is type 2.

### Claim 11 (depends on 5)

The method of claim 5 wherein the compound is selected from the following:

### Claim 12 (depends on 6)

The method of claim 6 wherein the compound is selected from the following: