# US 2021/0330671 A1 · Phenyloxadiazole derivatives as pgds inhibitors

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- Number: US 2021/0330671 A1
- Document ID: US20210330671A1
- Status: Published application
- Kind: A1
- Application number: 17/226,882
- Filed: 2021-04-09
- Published: 2021-10-28
- Earliest claimed: 2009-10-08
- Assignees: Sanofi
- Applicants: Sanofi
- Inventors: Christopher L. VANDEUSEN; Franz J. WEIBERTH; Harpal S. GILL; George LEE; Andrea HILLEGASS
- Web page: https://patentgrep.com/patent/US20210330671A1

## CPC

- A61K 31/506: not condensed and containing further heterocyclic rings
- C07D 217/06: with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 271/06: 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D 413/14: containing three or more hetero rings
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

This invention is directed to a compound of formula (1): wherein R1, R2 and R3 are as defined herein, a pharmaceutical composition comprising the compound, intermediates and processes for making said compounds, and the use of the compound to treat allergic and/or inflammatory disorders, particularly disorders such as allergic rhinitis, asthma, chronic obstructive pulmonary disease (COPD) and age-related macular degeneration (AMD).

## Claims

### Claim 1

A compound of formula (I):
wherein
R1 is hydrogen or C1-C3alkyl;
R2 is hydrogen, halogen or C1-C3alkyl; and
R3 is hydroxy alkyl;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R1 is hydrogen, R2 is hydrogen and R3 is hydroxy alkyl.

### Claim 3 (depends on 2)

The compound of claim 2 which is 2-Pyridin-2-yl-pyrimidine-5-carboxylic acid 3-5-(1-hydroxy-1 methyl-ethyl)[1,2,4]oxadiazol-3-yl]benzyl amide;

### Claim 4 (depends on 1)

The compound of claim 1 where R1 is C1-C5alkyl, R2 is hydrogen and R3 is hydroxyalkyl.

### Claim 5 (depends on 4)

The compound of claim 4 selected from the group consisting of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid ((S)-1-{3-[5-(1-hydroxy-1-methyl-ethyl)-1,2,4-oxadiazol-3-yl]-phenyl}-ethyl)-amide and 2-pyridin-2-yl-pyrimidine-5-carboxylic acid ((R)-1-{3-[5-(1-hydroxy-1-methyl-ethyl)-1,2,4-oxadiazol-3-yl]-phenyl}-ethyl)-amide.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising the compound according to claim 1 and a pharmaceutically acceptable carrier.

### Claim 7 (depends on 1)

A method for treating an allergic or inflammatory disorder in a patient in need thereof, comprising administering to the patient a pharmaceutically effective amount of the compound according to claim 1.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the allergic or inflammatory disorder is selected from the group consisting of allergic rhinitis, asthma, chronic obstructive pulmonary disease and age-related macular degeneration.

### Claim 9 (depends on 1)

A process for preparing a compound according to claim 1 comprising the steps of reacting a compound of formula X1
wherein R1, R2 and R3 are as defined in formula 1,
with an acid compound of formula
in the presence of a suitable coupling reagent.

### Claim 10 (depends on 1, 9)

The process of claim 9 wherein the compound according to claim 1 is
and the compound of formula XI is

### Claim 11 (depends on 10)

The process of claim 10 wherein the suitable coupling reagent is selected from the consisting of DMTMM, CDI, and TBTU.

### Claim 12 (depends on 1)

A process for preparing a compound according to claim 1 comprising the step of reacting a compound of formula XI
wherein R1, R2 and R3 are as defined in formula I,
with an ester compound of formula
Wherein R4 is C1-C3alkyl
in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD).

### Claim 13 (depends on 12)

The process of claim 12 wherein the compound of formula 1 is
and the compound of formula XI is

### Claim 14 (depends on 13)

The process of claim 13 wherein R4 of the ester compound is CH3.

### Claim 15 (depends on 1)

A process for preparing a compound according to claim 1 comprising the step of reacting a compound of formula XI
wherein R1, R2 and R3 are as defined in claim 1,
with an acid chloride compound of formula

### Claim 16 (depends on 1, 15)

The process of claim 15 wherein tie compound according to claim 1 is
and the compound of formula XI is

### Claim 17

A compound of formula
or an acid addition salt thereof.

### Claim at position 18

-24. (canceled)