# US 10,946,031 B2 · PDE4 inhibitor (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-ol

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- Number: US 10,946,031 B2
- Document ID: US10946031B2
- Status: Granted
- Kind: B2
- Application number: 16/593,171
- Filed: 2019-10-04
- Published: 2020-04-09
- Granted: 2021-03-16
- Earliest claimed: 2018-10-05
- Assignees: Pfizer Inc.
- Applicants: Pfizer Inc.
- Inventors: Joseph Walter Strohbach; David Clive Blakemore; Peter Jones; Matthew Alexander Perry
- Web page: https://patentgrep.com/patent/US10946031B2

## CPC

- A61K 31/69: Boron compounds
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61K 31/519: ortho- or peri-condensed with heterocyclic rings
- C07F 5/025: {Boronic and borinic acid compounds}
- C07F 7/1804: {Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896)}
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention relates to PDE4 inhibitor (R)-4-(5-(4-methoxy-3-propoxyphenyl)pyridin-3-yl)-1,2-oxaborolan-2-ol including the crystalline monohydrate thereof.

## Claims

### Claim 1

A compound of the structure
or a pharmaceutically acceptable salt thereof.

### Claim 2

A compound of the structure

### Claim 3

A compound of the structure
wherein the compound is characterized by a powder X-ray diffraction pattern comprising diffraction peaks at angles (2θ) of 11.0° 0 0.2°, 22.9°±0.2°, and 25.1°±0.2°.

### Claim 4 (depends on 3)

The compound of claim 3, wherein the compound is further characterized by a powder X-ray diffraction pattern comprising additional diffraction peaks at angles (2θ) of 11.4°±0.2°, 18.8°±0.2°, and 26.4°±0.2°.

### Claim 5 (depends on 3)

The compound of claim 3, wherein the compound is further characterized by a powder X-ray diffraction pattern comprising additional diffraction peaks at angles (2θ) of 11.4±0.2°, 13.2°±0.2°, 18.8°±0.2, 19.7°±0.2°, 21.3±0.2°, 2 and 26.4±0.2°.

### Claim 6 (depends on 3)

The compound of claim 3, wherein the compound is further characterized by a powder X-ray diffraction pattern comprising additional diffraction peaks at angles (2θ) of 11.4°±0.2, 13.2°±0.2°, 14.5°±0.2°, 15.1°±0.2°, 15.6°±0.2°, 18.8°±0.2°, 19.7°±0.2°, 21.3°±0.2°, and 26.4°±0.2°.

### Claim 7 (depends on 3)

The compound of claim 3, wherein the compound is further characterized by a powder X-ray diffraction pattern comprising additional diffraction peaks at angles (2θ) of 11.4°±0.2, 13.2°±0.2°, 14.5°±0.2°, 15.1°±0.2°, 15.6°±0.2°, 18.8°±0.2°, 19.4°±0.2°, 19.7°±0.2°, 21.3°±0.2°, 25.9°±0.2°, 26.4°±0.2°, and 27.5°±0.2°.

### Claim 8 (depends on 3)

The compound of claim 3, wherein the compound is further characterized by a powder X-ray diffraction pattern comprising additional diffraction peaks at angles (2θ) of 11.4°±0.2, 13.2°±0.2°, 14.5°±0.2°, 15.1°±0.2°, 15.6°±0.2°, 15.9°±0.2°, 17.7°±0.2°, 18.8°±0.2°, 19.4°±0.2°, 19.7°±0.2°, 20.5°±0.2°, 21.3°±0.2°, 25.9°±0.2°, 26.4°±0.2°, and 27.5°±0.2°.

### Claim 9 (depends on 3)

The compound of claim 3, wherein the compound is further characterized by a powder X-ray diffraction pattern comprising additional diffraction peaks at angles (2θ) of 11.4°±0.2°, 13.2°±0.2°, 14.5°±0.2°, 15.1°±0.2°, 15.6°±0.2°, 15.9°±0.2°, 17.7°±0.2°, 18.8°±0.2°, 19.4°±0.2°, 19.7°±0.2°, 20.5°±0.2°, 21.3°±0.2°, 22.0°±0.2°, 24.5°±0.2°, 25.9°±0.2°, 26.4°±0.2°, 27.5°±0.2°, and 28.4°±0.2°.

### Claim 10 (depends on 3)

The compound of claim 3, wherein the compound is further characterized by a powder X-ray diffraction pattern comprising additional diffraction peaks at angles (2θ) of 11.4°±0.2°, 13.2°±0.2°, 14.5°±0.2°, 15.1°±0.2°, 15.6°±0.2°, 15.9°±0.2°, 17.7°±0.2°, 18.8°±0.2°, 19.4°±0.2°, 19.7°±0.2°, 2.5°±0.2°, 21.3°±0.2°, 22.0°±0.2°, 23.8°±0.2°, 24.5°±0.2°, 25.6°±0.2°, 25.9°±0.2°, 26.4°±0.2°, 27.5°±0.2°, 28.4°±0.2°, 28.8°±0.2°, and 30.4°±0.2°.