# US 9,890,141 B2 · Crystalline pharmaceutical and methods of preparation and use thereof

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- Number: US 9,890,141 B2
- Document ID: US9890141B2
- Status: Granted
- Kind: B2
- Application number: 15/144,892
- Filed: 2016-05-03
- Published: 2017-02-02
- Granted: 2018-02-13
- Earliest claimed: 2009-10-21
- Assignees: Sarcode Bioscience Inc.
- Applicants: SARcode Bioscience Inc.
- Inventors: John Burnier
- Web page: https://patentgrep.com/patent/US9890141B2

## CPC

- C07D 405/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07D 405/10: linked by a carbon chain containing aromatic rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Novel crystalline polymorphic forms, Forms A, B, C, D, and E of a compound of Formula I, which has been found to be a potent inhibitor of LFA-1, are disclosed. Methods of preparation and uses thereof in the treatment of LFA-1 mediated diseases are also disclosed in this invention.

## Claims

### Claim 1

A composition comprising an isolated compound of Formula I:
wherein said compound is synthesized according to a method comprising the steps:
performing hydrolysis of Formula AA with a base:
wherein R is a carbon containing moiety; and
isolating the compound of Formula I,
wherein the hydrolysis is performed in a solution comprising acetone, the composition is essentially free of a chemical catalyst, and the compound of Formula I is isolated by way of recrystallization from a solution comprising acetone.

### Claim 2 (depends on 1)

The composition of claim 1, wherein R is a substituted or unsubstituted group selected from lower alkyl, lower alkenyl, lower alkynyl, cyclo(lower)alkyl, cyclo(lower)alkenyl, aryl, aralkyl, heterocyclyl, and heteroaryl groups.

### Claim 3 (depends on 1)

The composition of claim 1, wherein R is benzyl.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the base is sodium hydroxide.