# US 10,765,629 B2 · Solid complex, preparations and uses thereof

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- Number: US 10,765,629 B2
- Document ID: US10765629B2
- Status: Granted
- Kind: B2
- Application number: 16/634,072
- Filed: 2018-07-24
- Published: 2020-06-04
- Granted: 2020-09-08
- Earliest claimed: 2017-07-25
- Assignees: Allergan, Inc.
- Applicants: Allergan, Inc.
- Inventors: Ke Wu; Evgenyi Shalaev; Prem Swaroop Mohanty; Jinping Wan
- Web page: https://patentgrep.com/patent/US10765629B2

## CPC

- A61K 9/0051: {Ocular inserts or implants}
- A61K 9/0024: {Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue (compositions for intravenous administration, normal injectable solutions or dispersions for, e.g. subcutaneous administration A61K9/0019; brain implants A61K9/0085; (coated) prostheses, catheters or stents A61L)}
- A61K 31/559: having heterocyclic rings containing hetero atoms other than oxygen
- A61K 47/34: 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)
- A61K 47/40: Cyclodextrins; Derivatives thereof
- A61K 47/6951: {using cyclodextrin (cyclodextrins used as simple excipients A61K47/40)}
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## 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.

## Claims

### Claim 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.

### Claim 2 (depends on 1)

The solid complex of claim 1, which is crystalline.

### Claim 3 (depends on 2)

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).

### Claim 4 (depends on 1)

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).

### Claim 5 (depends on 1)

The solid complex of claim 1, which is amorphous.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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

### Claim 8 (depends on 7)

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

### Claim 9 (depends on 8)

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

### Claim 10 (depends on 9)

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.

### Claim 11 (depends on 9)

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

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 12)

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

### Claim 14 (depends on 12)

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

### Claim 15 (depends on 12)

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.

### Claim 16 (depends on 15)

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