Solid form and method for preparing the same

• US 9,084,822 B2
• Filed: 04/26/2013
• Issued: 07/21/2015
• Est. Priority Date: 12/28/2012
• Status: Active Grant

• Current Assignee: Industrial Technology Research Institute
• Original Assignee: Industrial Technology Research Institute
• Inventors: Hsieh, Meng-Yow, Shen, Hsin-Hsin, Liou, Yu-Bing, Chen, Chin-Fu, Lin, Li-Hsin, Huang, Hsiu-Hua, Chao, Ying-Hsueh, Chen, Miao-Tzu, Hung, Chih-Bing
• Primary Examiner(s): Barham, Bethany
• Assistant Examiner(s): Anthopolos, Peter
• Application Number:
  US13/871,491
• Publication Number:
  US 20140187591A1
• Time in Patent Office: 816 Days
• US Class Current: 1/1
• 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

Abstract

The disclosure provides a solid form and a method for preparing the same. The solid form consists essentially of a biodegradable copolymer and an amide-containing compound. The biodegradable copolymer is semi-crystalline due to the dipole-dipole interaction between the biodegradable copolymer and the urea. The method for preparing the above solid form includes: dissolving a biodegradable copolymer and an amide-containing compound in water at a first temperature, obtaining a solution; cooling the solution at a second temperature to form a solid mixture; and the solid mixture is subjected to a freeze-drying process at a third temperature.

Claims

1. A freeze-dried solid form consisting essentially of a biodegradable copolymer and an amide compound, wherein the biodegradable copolymer has a structure represented by Formula (I) or Formula (II):

A-B-BOX-B-A 

 

Formula (I); and

B-A-B-(BOX-B-A-B)_n-BOX-B-A-B 

 

Formula (II)

wherein A comprises a hydrophilic block of polyethylene glycol polymer, B comprises a hydrophobic block of polyester polymer, BOX is a bifunctional group monomer of 2,2′

-Bis(2-oxazoline) and used for coupling the blocks A-B or B-A-B, and n is an integer and the same or more than 0;

wherein the amide compound is selected from the group consisting of;

2. The solid form as claimed in claim 1, wherein the hydrophilic block of polyethylene glycol polymer comprises polyethylene glycol (PEG) or methoxy-poly(ethylene glycol) (mPEG).

3. The solid form as claimed in claim 1, wherein the hydrophobic block of polyester polymer comprises poly(lactide-co-glycolide) (PLGA), poly(propionic-co-lactic (PPLA), poly(valeric-co-lactic) (PVLA), or poly(caproic-co-lactic) (PCLA).

4. The solid form as claimed in claim 1, wherein the weight ratio of the biodegradable copolymer is 52-83 wt %, and the weight ratio of the amide compound is 17-48 wt %, based on the weight of the solid form.

5. The solid form as claimed in claim 1, wherein the solid form is completely dissolved in water within 5 min.

6. The solid form as claimed in claim 1, wherein the solid is prepared by a method comprising:

dissolving the biodegradable copolymer and the amide compound in water at a first temperature, obtaining a solution;

cooling the solution at a second temperature to form a solid mixture; and

freeze-drying the solid mixture at a third temperature.