IP Library Granted Patent US 9,708,303
Granted Patent B2
US 9,708,303 · App. 14/747,745 · Granted Jul 18, 2017

LFA-1 inhibitor and methods of preparation and polymorph thereof

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Quick Facts
Patent No.
US 9,708,303
App. No.
14/747,745
Granted
Jul 18, 2017
Kind
B2
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 (12)

1. A method of purifying a compound of Formula I:

or a salt thereof, comprising the steps:

a) obtaining crude compound of Formula I or a salt thereof and recrystallizing said crude compound with aqueous acetone; and

b) isolating said compound of Formula I or a salt thereof by removal of aqueous acetone.

2. The method of claim 1 , wherein said aqueous acetone is used in an amount of about 7 volumes.

3. The method of claim 1 , wherein said aqueous acetone is about 30% aqueous acetone.

4. The method of claim 1 , further comprising addition of a pH modifier to produce a pH of less than about 5.

5. The method of claim 4 , wherein said method produces a pH between about 1 and about 5.

6. The method of claim 4 , wherein said pH modifier is selected from an organic or mineral acid.

7. The method of claim 4 , wherein said pH modifier is hydrochloric acid.

8. The method of claim 1 , wherein said removal of aqueous acetone is by filtration.

9. The method of claim 1 , wherein said method is performed for a period of time ranging from about 1 hour to about 48 hours.

Assignments (6)
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 23, 2025
From: BAUSCH + LOMB IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 074050/0573 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 23, 2025
From: BAUSCH + LOMB IRELAND LIMITED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 074050/0682 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 23, 2025
From: BAUSCH + LOMB IRELAND LIMITED
To: CITIBANK, N.A., AS NOTES COLLATERAL AGENT
Reel/Frame 074050/0709 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 6, 2023
From: NOVARTIS PHARMACEUTICALS CORPORATION
To: BAUSCH + LOMB IRELAND LIMITED
Reel/Frame 065789/0853 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 22, 2020
From: NOVARTIS AG
To: NOVARTIS PHARMACEUTICALS CORPORATION
Reel/Frame 054134/0708 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 31, 2019
From: SARCODE BIOSCIENCE INC.
To: NOVARTIS AG
Reel/Frame 050900/0268 →