# US 8,772,495 B2 · 5-lipoxygenase-activating protein inhibitor

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- Number: US 8,772,495 B2
- Document ID: US8772495B2
- Status: Granted
- Kind: B2
- Application number: 12/471,106
- Filed: 2009-05-22
- Published: 2009-11-26
- Granted: 2014-07-08
- Earliest claimed: 2008-05-23
- Assignees: Panmira Pharmaceuticals, LLC
- Applicants: Kevin Murray Schaab; Nicholas Simon Stock
- Inventors: Kevin Murray Schaab; Nicholas Simon Stock
- Web page: https://patentgrep.com/patent/US8772495B2

## CPC

- C07D 401/14: containing three or more hetero rings
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 9/00: Drugs for disorders of the cardiovascular system
- 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 25/04: Centrally acting analgesics, e.g. opioids
- A61P 27/02: Ophthalmic agents
- A61P 29/02: without antiinflammatory effect
- 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)
- 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

Described herein is the FLAP inhibitor 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxy-pyridin-3-yl)-benzyl]-5-(5-methyl-pyridin-2-ylmethoxy)-1H-indol-2-yl]-2,2-dimethyl-propionic acid, or a pharmaceutically acceptable salt thereof. Also described are methods of preparing the FLAP inhibitor, or a pharmaceutically acceptable salt thereof, including solvates, and polymorphs thereof. Also described herein are pharmaceutical compositions suitable for administration to a mammal that include the FLAP inhibitor, or a pharmaceutically acceptable salt thereof, and methods of using such pharmaceutical compositions for treating respiratory conditions or diseases, as well as other leukotriene-dependent or leukotriene mediated conditions or diseases.

## Claims

### Claim 1

A crystalline polymorphic Form C of sodium 3-[3-(tert-butylsulfanyl)-1-[4-(6-ethoxy-pyridin-3-yl)benzyl]-5-(5-methyl-pyridin-2-yl-methoxy)-1H-indol-2-yl]-2,2-dimethylpropionate:
having an X-ray powder diffraction spectrum with peaks comprising the 2-theta values listed below, obtained with a diffractometer using copper Kα-radiation;
Angle 2-Theta°
Intensity %
15.6
42.7
16.6
43.3
17.2
69
17.8
42.6
18.4
49.2
19.1
100
19.8
40.5
20.8
91.6
23.1
47.8
23.8
59.2.

### Claim 2 (depends on 1)

The crystalline polymorphic Form C according to claim 1 having a single melting point at about 290° C. to about 295° C. as measured by differential scanning calorimetry (DSC).

### Claim 3 (depends on 1)

The crystalline polymorphic Form C according to claim 1 having a differential scanning calorimetry (DSC) thermogram or a thermo-gravimetric analysis (TGA) thermogram substantially similar to the ones set forth in FIG. 15.

### Claim 4 (depends on 1)

The crystalline polymorphic Form C according to claim 1 having physical and chemical stability (at 5° C., 25° C./60% relative humidity (RH), and/or 40° C./75% RH for at least one month in a humidity chamber).

### Claim 5 (depends on 1)

The crystalline polymorphic Form C according to claim 1 having an infrared (IR) spectrum substantially similar to the one set forth in FIG. 19.

### Claim 6 (depends on 1)

The crystalline polymorphic Form C according to claim 1 having an X-ray powder diffraction (XRPD) pattern substantially similar to an XRPD pattern obtained for crystals of Compound 2 obtained from methyl tert-butyl ether (MTBE) or acetonitrile.

### Claim 7 (depends on 1)

The crystalline polymorphic Form C according to claim 1, wherein the Crystalline Form C is desolvated.