# US 8,541,419 B2 · Isotopically enriched pyrimidin-5-yl acetic acid derivatives as CRTH2 antagonists

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- Number: US 8,541,419 B2
- Document ID: US8541419B2
- Status: Granted
- Kind: B2
- Application number: 13/061,921
- Filed: 2009-09-01
- Published: 2011-07-14
- Granted: 2013-09-24
- Earliest claimed: 2008-09-02
- Assignees: Actimis Pharmaceuticals, Inc.
- Applicants: Tai Wei Ly
- Inventors: Tai Wei Ly
- Web page: https://patentgrep.com/patent/US8541419B2

## CPC

- C07D 239/48: Two nitrogen atoms
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/02: Nasal agents, e.g. decongestants
- A61P 11/06: Antiasthmatics
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/04: Antipruritics
- A61P 17/06: Antipsoriatics
- A61P 19/00: Drugs for skeletal disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 27/02: Ophthalmic agents
- A61P 27/14: Decongestants or antiallergics
- A61P 35/02: specific for leukemia
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Provided herein are 2H- and 13C-enriched compounds of formula (I) or (II); wherein R is as defined herein, and wherein at least one hydrogen atom, in certain embodiments, three or more hydrogen atoms, are deuterium atoms or at least one carbon atom is a carbon-13 atom. Also provided are pharmaceutical compositions and methods using the 2H- and 13C-enriched compounds, useful for treating CRTH2-related diseases or disorders such as, for example, asthma, allergic rhinitis, atopic dermatitis, allergic conjuvatitis, Churg-Strauss syndrome, sinusitis, basophilic leukemia, chronic urticaria or basophilic leukocytosis.

## Claims

### Claim 1

An isotopically enriched compound of formula I:
or pharmaceutically acceptable salt thereof,
wherein
R is hydrogen, C1-6 alkyl, C3-8 cycloalkyl optionally substituted by C1-6 alkyl, or phenyl optionally substituted with 1-4 substituents selected from halogen, C1-4 alkyl optionally substituted with mono-, di- or tri- halogen, and C1-4 alkoxy; and wherein
one or more hydrogen atoms are replaced by a deuterium atom or
one or more carbon atoms are replaced by a carbon-13 atom.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R is phenyl.

### Claim 3 (depends on 1)

The compound of claim 1 of the formula III:
wherein
each Y atom is a hydrogen atom or deuterium atom; and
each X atom is a carbon-12 atom or carbon-13 atom,
wherein at least one Y atom is deuterium or at least one X atom is a carbon-13 atom.

### Claim 4 (depends on 1)

The compound of claim 1, wherein at least one Y atom is deuterium atom.

### Claim 5 (depends on 1)

The compound of claim 1, wherein at least three Y atoms are deuterium atoms.

### Claim 6 (depends on 3)

The compound of claim 3, wherein at least one X atom is a carbon-13 atom.

### Claim 7 (depends on 3)

The compound of claim 3, wherein at least two X atoms are carbon-13 atoms.

### Claim 8 (depends on 1)

The compound of claim 1 of the formula V:
wherein each Y atom is a hydrogen or a deuterium and at least one Y atom is a deuterium.

### Claim 9 (depends on 1)

A compound of claim 1 of the formula
or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1)

An amine salt compound comprising an acid compound according to claim 1 and a pharmaceutically acceptable amine.

### Claim 11 (depends on 1, 10)

The amine salt compound of claim 10, wherein the amine salt compound comprises a diamine salt comprising about two molar equivalents of the acid compound according to claim 1 and one molar equivalent of the diamine.

### Claim 12 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.