Solid complex, preparations and uses thereof

Patent metadata

Field	Value
Publication number	US-10765629-B2
Application number	US-201816634072-A
Country	US
Kind code	B2
Filing date	Jul 24, 2018
Priority date	Jul 25, 2017
Publication date	Sep 8, 2020
Grant date	Sep 8, 2020

Abstract

Described herein is a solid complex comprising (Z)-7-((1R,2R,3R,5S)-2-((S,E)-5-(2,5-dichlorothiophen-3-yl)-3-hydroxypent-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enamide (hereinafter “Compound 1”) and γ-cyclodextrin, and preparations and uses thereof. Also described herein are certain solid forms, preparations and uses thereof.

First claim

What is claimed is:

1. A solid complex of (Z)-7-((1R,2R,3R,5S)-2-((S,E)-5-(2,5-dichlorothiophen-3-yl)-3-hydroxypent-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enamide with γ-cyclodextrin.

2. The solid complex of claim 1 , which is crystalline.

3. The solid complex of claim 2 , which has an XRPD pattern with peaks at 7.58, 10.68, 14.33, 16.82, 23.82, 26.89, 28.51, 30.06, and 35.13, each of the diffraction angles being ±0.2 degrees (2θ).

4. The solid complex of claim 1 , which has an XRPD pattern with peaks at 10.83, 11.72, 12.36, 14.51, 19.42, 20.56, and 26.80, each of the diffraction angles being ±0.2 degrees (2θ).

5. The solid complex of claim 1 , which is amorphous.

6. The solid complex of claim 1 , wherein the molar ratio of (Z)-7-((1R,2R,3R,5S)-2-((S,E)-5-(2,5-dichlorothiophen-3-yl)-3-hydroxypent-1-en-1-yl)-3,5-dihydroxycyclopentyl)hept-5-enamide versus γ-cyclodextrin is about 1:1.

7. A pharmaceutical composition comprising the solid complex of claim 1 and a pharmaceutically acceptable excipient.

8. The pharmaceutical composition of claim 7 , which is in the form of an intraocular implant.

9. The pharmaceutical composition of claim 8 , wherein the intraocular implant comprises a biodegradable polymer.

10. The pharmaceutical composition of claim 9 , wherein the biodegradable polymer is a homo- or copolymer of D-lactic acid, L-lactic acid, racemic lactic acid, glycolic acid, caprolactone, and combinations thereof.

11. The pharmaceutical composition of claim 9 , wherein the biodegradable polymer is a random copolymer of 50/50 PLGA.

12. A method of preparing a pharmaceutical composition comprising combining the solid complex of claim 1 with one or more pharmaceutically acceptable excipients.

13. The method of claim 12 , wherein the pharmaceutical composition is in the form of a solution for ophthalmic application.

14. The method of claim 12 , wherein the pharmaceutical composition is a solid implant.

15. The method of claim 12 , wherein the method further comprises subjecting the combination of the solid complex and one or more pharmaceutically acceptable excipients to hot-melt extrusion.

16. The method of claim 15 , wherein the pharmaceutical composition is a solid implant.

Assignees

• Allergan Inc

Inventors

• Wu Ke
• Shalaev Evgenyi
• Mohanty Prem Swaroop
• Wan Jinping

Classifications

• A61K47/6951

  using cyclodextrin (cyclodextrins used as simple excipients A61K47/40) · CPC title

• A61K31/559 Primary

  having heterocyclic rings containing hetero atoms other than oxygen · CPC title

• A61K47/40

  Cyclodextrins; Derivatives thereof · CPC title

• A61K47/34

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence) · CPC title

• A61K9/0051 Primary

  Ocular inserts or implants · CPC title