Crystalline forms of bimatoprost acid, methods for preparation, and methods for use thereof

Patent metadata

Field	Value
Publication number	US-9855232-B2
Application number	US-201514802046-A
Country	US
Kind code	B2
Filing date	Jul 17, 2015
Priority date	Dec 28, 2012
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

The invention provides new crystalline forms of 7-[3,5-Dihydroxy-2-(3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-hept-5-enoic acid. This compound is commonly referred to as “bimatoprost acid.” The novel crystalline forms are designated forms I, II, and III. The invention crystalline forms are useful for solid ocular implant formulations, utilized in the treatment of various ocular conditions, such as, for example, ocular hypertension. In addition, invention crystalline forms are useful for solid or semisolid dosage formulations used to treat ocular hypertension.

First claim

What is claimed is:

1. A solid implant formulation, the solid implant formulation comprising a therapeutically effective amount of 7-[3,5-Dihydroxy-2-(3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-hept-5-enoic acid in crystalline form II as characterized by X-ray diffraction pattern of about 12.0, 14.2, 16.0, 18.8, 20.6, 22.6, 24.1, 28.1, 35.9 and 36.5.

2. A solid implant, the solid implant comprising a therapeutically effective amount of 7-[3,5-Dihydroxy-2-(3-hydroxy-5-phenyl-pent-1-enyl)-cyclopentyl]-hept-5-enoic acid in crystalline form III as characterized by X-ray diffraction pattern of about 3.9, 9.8, 13.0, 14.5, 15.4, 18.4, 19.3, 20.8 and 24.6.

3. The solid implant formulation of claim 1 , wherein the solid implant formulation is a solid ocular implant formulation.

4. The solid implant formulation of claim 2 , wherein the solid implant formulation is a solid ocular implant formulation.

5. A method for treating ocular hypertension comprising administering to a subject in need thereof the solid implant formulation of claim 3 .

6. A method for treating ocular hypertension comprising administering to a subject in need thereof the solid implant formulation of claim 4 .

Assignees

• Allergan Inc

Inventors

• Wu Ke
• Feng Shaoxin
• Karami Thomas K
• Smith Scott W

Classifications

• A61P27/06

  Antiglaucoma agents or miotics · CPC title

• C07C59/54 Primary

  containing six-membered aromatic rings and other rings · CPC title

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• A61K9/0051

  Ocular inserts or implants · CPC title

• C07C405/00 Primary

  Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins {; Analogues or derivatives thereof} · CPC title