# US 11,299,492 B2 · JAK kinase inhibitor compounds for treatment of respiratory disease

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- Number: US 11,299,492 B2
- Document ID: US11299492B2
- Status: Granted
- Kind: B2
- Application number: 17/248,015
- Filed: 2021-01-05
- Published: 2021-05-06
- Granted: 2022-04-12
- Earliest claimed: 2015-11-03
- Assignees: Theravance Biopharma R&D IP, LLC
- Applicants: Theravance Biopharma R&D IP, LLC
- Inventors: Paul R. Fatheree; John R. Jacobsen; Gary E. L. Brandt; Melissa Fleury; Lan Jiang; Cameron Smith; Steven D. E. Sullivan; Lori Jean Van Orden; Anne-Marie Beausoleil
- Web page: https://patentgrep.com/patent/US11299492B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61K 31/416: condensed with carbocyclic ring systems, e.g. indazole
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The invention provides compounds of formula (I): wherein X is and the variables are defined in the specification, or a pharmaceutically-acceptable salt thereof, that are useful as JAK kinase inhibitors. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat respiratory diseases, and processes and intermediates useful for preparing such compounds.

## Claims

### Claim 1

A process of preparing a compound of formula (IV):
or a pharmaceutically-acceptable salt thereof,
wherein R8 is selected from hydrogen, methyl, C2-4alkyl, and C3-4cycloalkyl, the process comprising reacting a compound of formula 1:
with a compound of formula 2″:
to provide a compound of formula (IV) or a pharmaceutically-acceptable salt thereof.

### Claim 2 (depends on 1)

The process of claim 1, wherein the reaction between the compound of formula 1 and the compound of formula 2″ occurs in the presence of a reducing agent.

### Claim 3 (depends on 2)

The process of claim 2, wherein the reducing agent is sodium cyanoborohydride.

### Claim 4 (depends on 2)

The process of claim 2, wherein the reducing agent is sodium triacetoxyborohydride.

### Claim 5 (depends on 2)

The process of claim 2, wherein the reaction between the compound of formula 1 and the compound of formula 2″ occurs in the presence of acetic acid.

### Claim 6 (depends on 2)

The process of claim 2, wherein the reaction between the compound of formula 1 and the compound of formula 2″ is conducted at a temperature in the range of about 20° C. to about 40° C.

### Claim 7 (depends on 2)

The process of claim 2, wherein the reaction between the compound of formula 1 and the compound of formula 2″ is conducted in an inert diluent.

### Claim 8 (depends on 7)

The process of claim 7, wherein the inert diluent is dichloromethane, methanol, tetrahydrofuran, or dimethylformamide.

### Claim 9 (depends on 7)

The process of claim 7, wherein the inert diluent is dimethylformamide.

### Claim 10 (depends on 2)

The process of claim 2, wherein R8 is hydrogen.

### Claim 11 (depends on 2)

The process of claim 2, wherein R8 is methyl.

### Claim 12 (depends on 2)

The process of claim 2, wherein R8 is C2-4alkyl.

### Claim 13 (depends on 2)

The process of claim 2, wherein R8 is C3-4cycloalkyl.