# US 10,214,517 B2 · LFA-1 inhibitor and methods of preparation and polymorph thereof

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- Number: US 10,214,517 B2
- Document ID: US10214517B2
- Status: Granted
- Kind: B2
- Application number: 15/621,141
- Filed: 2017-06-13
- Published: 2018-05-03
- Granted: 2019-02-26
- Earliest claimed: 2012-07-25
- Assignees: Sarcode Bioscience Inc.
- Applicants: SARcode Bioscience Inc.
- Inventors: James Robert Zeller; Sripathy Venkatraman; Elisabeth C. A. Brot; Subashree Iyer; Michael Hall
- Web page: https://patentgrep.com/patent/US10214517B2

## CPC

- C07D 407/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/02: Immunomodulators
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 405/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07B 63/00: Purification; Separation (separation of optically-active compounds C07B57/00); Stabilisation; Use of additives
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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

Methods of preparation and purification of a compound of Formula I, intermediates thereof, a polymorph thereof, and related compounds are disclosed. Formulations and uses thereof in the treatment of LFA-1 mediated diseases are also disclosed.

## Claims

### Claim 1

A crystalline form of the compound of Formula I:
or a salt thereof,
which is crystalline Form II.

### Claim 2 (depends on 1)

The crystalline form of claim 1, having an X-ray powder diffraction pattern comprising the following peaks, in terms of 2-theta, at about 10.8, 16.4, and 21.8 degrees.

### Claim 3 (depends on 1)

The crystalline form of claim 1, wherein having an X-ray powder diffraction pattern substantially as shown in FIG. 4.

### Claim 4 (depends on 1)

The crystalline form of claim 1, having a differential scanning calorimetry thermogram (DSC) comprising an endothermic peak at about 37.8° C.

### Claim 5 (depends on 1)

The crystalline form of claim 1, the having a differential scanning calorimetry thermogram (DSC) comprising a melting transition at about 155.5° C.

### Claim 6 (depends on 1)

The crystalline form of claim 1, having a differential scanning calorimetry thermogram (DSC) substantially as shown in FIG. 7.

### Claim 7 (depends on 1)

The crystalline form of claim 1, having a thermogravimetric analysis (TGA) substantially as shown in FIG. 8.

### Claim 8 (depends on 1)

The crystalline form of claim 1, having a water content of about 3.2 wt % by Karl Fisher titration.

### Claim 9 (depends on 1)

A composition comprising the crystalline form of claim 1.

### Claim 10 (depends on 9)

The composition of claim 9, wherein said composition comprises at least one pharmaceutically acceptable carrier.

### Claim 11 (depends on 9)

The composition of claim 9, wherein the composition is at least about 50% by weight Form II.

### Claim 12 (depends on 9)

The composition of claim 9, wherein the composition is at least about 5% by weight Form II.

### Claim 13 (depends on 1)

A process for preparing the crystalline form of claim 1, comprising combining the compound of Formula I with acetone and n-heptane.

### Claim 14 (depends on 1)

The crystalline form of claim 1, prepared by a process comprising combining the compound of Formula I with acetone and n-heptane.

### Claim 15 (depends on 1)

The crystalline form of claim 1 which is a monohydrate.