# US 2024/0199643 A1 · Substituted benzoxazole and benzofuran compounds as pde7 inhibitors

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- Number: US 2024/0199643 A1
- Document ID: US20240199643A1
- Status: Published application
- Kind: A1
- Application number: 18/210,382
- Filed: 2023-06-15
- Published: 2024-06-20
- Earliest claimed: 2017-07-12
- Assignees: Dart NeuroScience, LLC
- Applicants: Dart NeuroScience, LLC
- Inventors: Vincent John Santora; Mi Chen; DeMichael Chung
- Web page: https://patentgrep.com/patent/US20240199643A1

## CPC

- C07D 498/04: Ortho-condensed systems
- C07D 498/10: Spiro-condensed systems
- A61P 25/00: Drugs for disorders of the nervous system
- C07D 491/04: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Substituted benzoxazole and benzofuran chemical entities of Formula (I): wherein, V, W, X, Y, Z, and m have any of the values described herein and compositions comprising such chemical entities; processes for making them; and their use in a wide range of methods, including metabolic and reaction kinetic studies; detection and imaging techniques; radioactive treatments; and the treatment of one or more disorders, including neurological, cognitive, immunological, and inflammatory disorders, as well as other conditions and diseases involving PDE7 or cyclic nucleotide signaling.

## Claims

### Claim at position 1

-78. (canceled)

### Claim 79

A pharmaceutical composition comprising: a pharmaceutically acceptable carrier; and a compound of Formula (I), or a pharmaceutically acceptable salt thereof, selected from the group consisting of:
5-chloro-2-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-ylmethyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one;
5-chloro-2-[(3-methoxy-3-methylazetidin-1-yl)methyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one;
5-chloro-2-{[3-(hydroxymethyl)pyrrolidin-1-yl]methyl}-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one; and
5-chloro-2-({[2-(dimethylamino)ethyl](methyl)amino}methyl)-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one.

### Claim 80 (depends on 79)

The pharmaceutical composition of claim 79, wherein the compound is
5-chloro-2-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-ylmethyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 81 (depends on 79)

The pharmaceutical composition of claim 79, wherein the compound is
5-chloro-2-[(3-methoxy-3-methylazetidin-1-yl)methyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 82 (depends on 79)

The pharmaceutical composition of claim 79, wherein the compound is
5-chloro-2-{[3-(hydroxymethyl)pyrrolidin-1-yl]methyl}-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 83 (depends on 79)

The pharmaceutical composition of claim 79, wherein the compound is
5-chloro-2-({[2-(dimethylamino)ethyl](methyl)amino}methyl)-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 84 (depends on 79)

A method of treating inhibiting or relieving a disorder or ameliorating a symptom of a disorder that includes having an aberrant or dysregulated signaling pathway mediated by PDE7 in a subject, the method comprising administering a pharmaceutical composition of claim 79 to a subject in need thereof.

### Claim 85 (depends on 84)

The method of claim 84, wherein the compound is
5-chloro-2-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-ylmethyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 86 (depends on 84)

The method of claim 84, wherein the compound is
5-chloro-2-[(3-methoxy-3-methylazetidin-1-yl)methyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 87 (depends on 84)

The method of claim 84, wherein the compound is
5-chloro-2-{[3-(hydroxymethyl)pyrrolidin-1-yl]methyl}-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 88 (depends on 84)

The method of claim 84, wherein the compound is
5-chloro-2-({[2-(dimethylamino)ethyl](methyl)amino}methyl)-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 89

A method of treating inhibiting or relieving a disorder or ameliorating a symptom of a disorder that includes having an aberrant or dysregulated signaling pathway mediated by PDE7 in a subject, the method comprising administering a compound of Formula (I), or a pharmaceutically acceptable salt thereof, selected from the group consisting of
5-chloro-2-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-ylmethyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one;
5-chloro-2-[(3-methoxy-3-methylazetidin-1-yl)methyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one;
5-chloro-2-{[3-(hydroxymethyl)pyrrolidin-1-yl]methyl}-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one; and
5-chloro-2-({[2-(dimethylamino)ethyl](methyl)amino}methyl)-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one.

### Claim 90 (depends on 89)

The method of claim 89, wherein the compound is
5-chloro-2-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-ylmethyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 91 (depends on 89)

The method of claim 89, wherein the compound is
5-chloro-2-[(3-methoxy-3-methylazetidin-1-yl)methyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof

### Claim 92 (depends on 89)

The method of claim 89, wherein the compound is
5-chloro-2-{[3-(hydroxymethyl)pyrrolidin-1-yl]methyl}-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof

### Claim 93 (depends on 89)

The method of claim 89, wherein the compound is
5-chloro-2-({[2-(dimethylamino)ethyl](methyl)amino}methyl)-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof

### Claim 94 (depends on 89)

The method of claim 89, wherein the disorder is selected from the group consisting of a cognitive disorder, a neurodegenerative disorder, a cancer or hematological disorder, a dermatological disorder, an inflammatory disorder, an immunological disorder, and an autoimmune disorder.

### Claim 95 (depends on 94)

The method of claim 94, wherein the compound is
5-chloro-2-[(1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-ylmethyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 96 (depends on 94)

The method of claim 94, wherein the compound is
5-chloro-2-[(3-methoxy-3-methylazetidin-1-yl)methyl]-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 97 (depends on 94)

The method of claim 94, wherein the compound is
5-chloro-2-{[3-(hydroxymethyl)pyrrolidin-1-yl]methyl}-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.

### Claim 98 (depends on 94)

The method of claim 94, wherein the compound is
5-chloro-2-({[2-(dimethylamino)ethyl](methyl)amino}methyl)-7,8-dihydro-6H-spiro[[1,3]oxazolo[5,4-f]quinazoline-9,1′-cyclohexane]-7-one, or a pharmaceutically acceptable salt thereof.