# US 9,518,027 B2 · Deuterated momelotinib

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- Number: US 9,518,027 B2
- Document ID: US9518027B2
- Status: Granted
- Kind: B2
- Application number: 14/759,028
- Filed: 2014-01-08
- Published: 2015-12-17
- Granted: 2016-12-13
- Earliest claimed: 2013-01-09
- Assignees: Concert Pharmaceuticals, Inc.
- Applicants: Concert Pharmaceuticals Inc.
- Inventors: Robert Silverman
- Web page: https://patentgrep.com/patent/US9518027B2

## CPC

- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07B 59/002: {Heterocyclic compounds}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention in one embodiment provides a compound of Formula I, or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula I are as defined in the specification.

## Claims

### Claim 1

A compound of Formula I:
or a pharmaceutically acceptable salt thereof, wherein:
Y1, Y2, Y3, Y4, Z1, Z2, Z3, Z4, W1 and W2 are each independently selected from hydrogen and deuterium;
provided that if Y1, Y2, Y3, Y4, Z1, Z2, Z3, Z4, and W1 are each hydrogen, then W2 is deuterium.

### Claim 2 (depends on 1)

The compound of claim 1, wherein Y1, Y2, Y3 and Y4 are each hydrogen.

### Claim 3 (depends on 1)

The compound of claim 1, wherein Y1, Y2, Y3 and Y4 are each deuterium.

### Claim 4 (depends on 1)

The compound of claim 1, wherein Z1, Z2, Z3 and Z4 are each hydrogen.

### Claim 5 (depends on 1)

The compound of claim 1, wherein Z1, Z2, Z3 and Z4 are each deuterium.

### Claim 6 (depends on 1)

The compound of claim 1, wherein W1 and W2 are each hydrogen.

### Claim 7 (depends on 1)

The compound of claim 1, wherein W1 and W2 are each deuterium.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is selected from any one of the compounds (Cmpd) set forth in Table 1 (below):
TABLE 1
Y1 = Y2 =
Z1 = Z2 =
Cmpd #
Y3 = Y4
Z3 = Z4
W1 = W2
101
H
H
D
102
H
D
H
103
H
D
D
104
D
H
H
105
D
H
D
106
D
D
H
107
D
D
D
or a pharmaceutically acceptable salt thereof, wherein any atom not designated as deuterium in Formula I is present at its natural isotopic abundance.

### Claim 9 (depends on 1)

The compound of claim 1, wherein any atom not designated as deuterium is present at its natural isotopic abundance.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1 or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable carrier.

### Claim 11 (depends on 1)

A method of treating a disease selected from chronic myeloproliferative neoplasms (MPNs), primary myelofibrosis (PMF) post-polycythemia vera (PV) or post-essential thrombocythemia (ET), comprising administering to a subject in need of such treatment a compound of claim 1.

### Claim 12 (depends on 1)

A method of inhibiting a member of the MK family of kinases in a cell, comprising contacting the cell with a compound of claim 1.

### Claim 13 (depends on 2)

The compound of claim 2, wherein Z1, Z2, Z3 and Z4 are each hydrogen.

### Claim 14 (depends on 3)

The compound of claim 3, wherein Z1, Z2, Z3 and Z4 are each hydrogen.

### Claim 15 (depends on 2)

The compound of claim 2, wherein Z1, Z2, Z3 and Z4 are each deuterium.

### Claim 16 (depends on 3)

The compound of claim 3, wherein Z1, Z2, Z3 and Z4 are each deuterium.

### Claim 17 (depends on 2)

The compound of claim 2, wherein W1 and W2 are each hydrogen.

### Claim 18 (depends on 3)

The compound of claim 3, wherein W1 and W2 are each hydrogen.

### Claim 19 (depends on 4)

The compound of claim 4, wherein W1 and W2 are each hydrogen.

### Claim 20 (depends on 5)

The compound of claim 5, wherein W1 and W2 are each hydrogen.

### Claim 21 (depends on 1)

The compound of claim 1, wherein the deuterium incorporation at each designated deuterium atom is at least 90%.

### Claim 22 (depends on 1)

The compound of claim 1, wherein the deuterium incorporation at each designated deuterium atom is at least 95%.

### Claim 23 (depends on 1)

The compound of claim 1, wherein the deuterium incorporation at each designated deuterium atom is at least 97%.