Hydrophilic Polyurethane Compositions

• US 20090291120A1
• Filed: 06/27/2007
• Published: 11/26/2009
• Est. Priority Date: 07/05/2006
• Status: Active Grant

• Current Assignee: Ferring BV (Ferring Holding SA)
• Original Assignee: Ferring BV (Ferring Holding SA)
• Inventors: Zurutuza, Amaia, Tuominen, Jukka, Livingston, Mark, Halliday, Janet A.
• Granted Patent: US 8,974,813 B2
• Time in Patent Office: Days
• US Class Current: 424/432
• CPC Class Codes: A61K 31/4196 1,2,4-Triazoles
• CPC Class Codes: 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
• CPC Class Codes: 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
• CPC Class Codes: A61K 9/0036 Devices retained in the vagina or cervix for a prolonged period, e.g. intravaginal rings, medicated tampons, medicated diaphragms
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C08G 18/2063 having two nitrogen atoms in the condensed ring system
• CPC Class Codes: C08G 18/4841 containing oxyethylene end groups
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/758 containing two or more cycloaliphatic rings

Abstract

A water-swellable linear polymer is made by reacting together a polyethylene oxide of number average molecular weight less than 4,000, an aliphatic diol, and a difunctional diisocyanate. Controlled release composition comprises the polymer together with an active agent. The polymer is able to take up pharmaceutically active agents of molecular weight 200 to 20,000.

Claims

1. A water-swellable linear polymer obtainable by reacting together:

(a) a polyethylene oxide of number average molecular weight less than 4000;

(b) an aliphatic diol; and

(c) a difunctional isocyanate,

wherein the ratio of components (a) to (b) to (c) is in the range of 0.01-0.1 to 1 to 1.01-1.1 in terms of equivalent weights.

2. A linear polymer according to claim 1, wherein the polyethylene oxide is a diol of equivalent weight 200 to 4000 g/mol.

3. A linear polymer according to claim 1, wherein the aliphatic diol is C₅ to C₂₀ diol.

4. A linear polymer according to claim 3, wherein the aliphatic diol is a C₈ to C₁₅ diol.

5. A linear polymer according to claim 4, wherein the aliphatic diol is 1,6-hexanediol, 1,10-decanediol, 1,12-dodecanediol or 1,16-hexadecanediol.

6. A linear polymer according to claim 1, wherein the difunctional isocyanate is dicyclohexylmethane-4,4-diisocyanate, diphenylmethane-4,4-diisocyanate, or 1,6-hexamethylene diisocyanate.

8. A linear polymer according to claim 1, wherein the amount of polyethylene oxide units is less than 50 wt % of the polymer.

9. A linear polymer according to claim 1, wherein the amount of aliphatic diol exceeds 20 wt % of the polymer.

10. A linear polymer according to claim 1, wherein the amount of diisocyanate is 20-50 wt % of the polymer.

11. A method of producing the water-swellable linear polymer according to claim 1, which comprises melting and drying the polyethylene oxide together with the aliphatic diol at a temperature of 85°

C. to 100°

C. under vacuum; and

then adding the difunctional isocyanate.

12. A controlled release composition, which comprises the linear polymer of claim 1 together with an active agent.

13. A composition according to claim 12 which has been processed into a solid dosage form.

14. A composition according to claim 13 wherein the dosage form is a suppository, vaginal ring or pessary, a bucchal insert, or a transdermal patch.

15. A composition according to claim 13 wherein the dosage form is an implant.

16. A composition according to claim 12, wherein the active agent is a pharmaceutically active agent of molecular weight in the range 200 to 20,000.

7. (canceled)