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Hydroswellable, segmented, aliphatic polyurethanes and polyurethane ureas

a polyurethane and urea technology, applied in the field of hydroswellable (or waterswellable) absorbable and nonabsorbable aliphatic, segmented polyurethanes and polyurethanes, can solve the problems of chemical degradation, prior art is virtually silent on self-standing peu and peu liquid solventless compositions, etc., to achieve the function of diseased or defective articulating joints, prolong effective device performance, and increase volume

Inactive Publication Date: 2012-08-16
POLY MED
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to different types of hydroswellable polyurethanes and polyurethane-ureas that can be used as vehicles for controlled release formulations of bioactive agents, as well as for tissue repair and the treatment of inflammation and cancer. These polyurethanes and polyurethane-ureas exhibit an increase in volume when placed in the biological environment, which can be caused by the interlinking of polyoxyalkylene chains with polyalkylene chains and the interlinking of polyoxyalkylene chains with polyalkylene urethane segments. The polyurethanes can also be chemically crosslinked, microporosity can be achieved, and aromatic groups can be added to stabilize the chain against degradation. These polyurethanes and polyurethane-ureas can be used as artificial cartilage for restoring the function of diseased joints.

Problems solved by technology

Of the cited drawbacks are those associated with (1) the generation of aromatic diamines, which are considered to be toxic upon degradation of segmented copolymers made using aromatic diisocyanates for interlinking; (2) chain degradation due to oxidation or radiation degradation of the polyether component of segmented copolymers, and particularly those which encounter frequent mechanical stresses in the biological environment; and (3) chemical degradation in chemically and mechanically hostile biological environments of the urethane links of segmented copolymers and particularly those comprising reactive aromatic urethane linkages.
However, the prior art is virtually silent on self-standing PEU and PEUU liquid solventless compositions for use in pharmaceutical formulations and / or medical devices.
Similarly, the prior art on polyether-urethanes is practically silent on hydroswellable (or water-swellable) systems, in spite of the fact that it covered elastomeric, segmented, hydrophilic polyether-urethane-based, lubricious coating compositions based on aromatic diisocyanate and polyethylene glycol (U.S. Pat. No. 4,990,357)—it did not suggest a self-standing material for medical device applications.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis and Characterization of a Typical Polyether-carbonate-urethane, P-1

[0023]For an initial charge, poly(ethylene glycol) (Mn=400 Da) (0.15 moles) and tin(II) 2-ethyl hexanoate (3.53×10−4 moles) were added to a 500 mL, 3-neck, round-bottom flask equipped with a PTFE coated magnetic stir bar. The contents were heated to 70° C. and allowed to stir for 10 minutes. For a second charge, trimethylene carbonate (0.882 moles) was added and the contents were heated to 135° C. Conditions were maintained until practically complete monomer conversion was achieved. The magnetic stir bar was removed and replaced by a stainless steel mechanical stirrer. The polymer was cooled to room temperature. For a third charge, 1,6-diisocyanatohexane (0.12 moles) was added and the contents were stirred until complete mixing was achieved. The contents were stirred and heated to 100° C. Conditions were maintained for 1.25 hours. The polymer was allowed to cool to room temperature and then dissolved in an...

example 2

Synthesis and Characterization of Liquid Polyether-ester-urethane: General Method

[0024]For an initial charge, poly(ethylene glycol) (Mn=400 Da) and tin(II) 2-ethyl hexanoate were added to a 500 mL, 3-neck, round-bottom flask equipped with a PTFE coated magnetic stir bar. The contents were heated to 70° C. and allowed to stir for 10 minutes. For a second charge, dl-lactide and glycolide were added and the contents were heated to 135° C. Conditions were maintained until practically complete monomer conversion was achieved. The magnetic stir bar was removed and replaced with a stainless steel mechanical stirrer. The polymer was cooled to room temperature. For a third charge, 1,6-diisocyanatohexane was added and the contents were stirred until complete mixing was achieved. The contents were stirred and heated to 100° C. Conditions were maintained for 1.25 hours. The polymer was allowed to cool to room temperature and then dissolved in an equal part of tetrahydrofuran. The polymer soluti...

example 3

Synthesis and Characterization of Typical Polyether-ester-urethanes Using the General Method of Example 2, P-2, P-3, and P-4

[0025]Polyether-ester-urethanes P-2, P-3, and P-4 were prepared using the method of Example 2 with 0.15, 2.225, 0.15 moles of polyethylene glycol (Mn=400 Da), 2.60×10−4, 3.18×10−4, 2.60×10−4 moles of tin(II) 2-ethyl hexanoate, 0.52, 0.64, 0.52 moles of dl-lactide, 0.13, 0.16, 0.13 moles of glycolide, and 0.18, 0.18, 0.12 moles of 1,6-diisocyanatohexane, respectively. Polymers P-2, P-3, and P-4 were characterized for molecular weight by GPC using tetrahydrofuran as the mobile phase which resulted in Mn of 11, 9, and 9 kDa, Mw of 20, 14, and 15 kDa, Mp of 20, 12, 14, kDa, and PDI of 1.9, 1.6, and 1.6, respectively. Identity and composition were confirmed by FT-IR and NMR, respectively.

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PUM

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Abstract

Hydroswellable, absorbable and non-absorbable, aliphatic, segmented polyurethanes and polyurethane-urea capable of swelling in the biological environment with associated increase in volume of at least 3 percent have more than one type of segments, including those derived from polyethylene glycol and the molecular chains are structurally tailored to allow the use of corresponding formulations and medical devices as carriers for bioactive agents, rheological modifiers of cyanoacrylate-based tissue adhesives, as protective devices for repairing defective or diseased components of articulating joints and their cartilage, and scaffolds for cartilage tissue engineering.

Description

CROSS REFERENCE TO RELATED APPLICATION[0001]The present application claims the benefit of prior provisional application, U.S. Ser. No. 61 / 069,046, filed Mar. 12, 2008, and is a continuation of U.S. Ser. No. 12 / 830,391, filed Feb. 26, 2009, both of which are hereby incorporated by reference in their entirety.FIELD OF THE INVENTION[0002]The present invention is directed to hydroswellable (or water-swellable) absorbable and non-absorbable aliphatic, segmented polyurethanes and polyurethane-ureas, which can undergo swelling when placed in the biological environment manifested through an at least 3 percent increase in volume by virtue of having a highly hydrophilic polyalkylene oxide as an inherent part of their segmented chain molecules. By varying the type and fraction of the different segments constituting the copolymers, their pharmaceutical and biomedical applications as non-absorbable and absorbable materials entail their use in carriers for the controlled release of bioactive agen...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/65A61P31/00C08G18/72
CPCA61L24/0021C08G64/0241A61L27/52A61L2430/06C08G18/12C08G18/4244C08G18/428C08G18/4283C08G18/44C08G18/4887C08G18/73C08G2230/00A61L27/18C08L75/04C08G18/3206A61P31/00C08G18/341
Inventor SHALABY, SHALABY W.CORBETT, JOEL T.INGAM, DAVID R.VAUGHN, MICHAEL A.SHALABY, JAMES E.
Owner POLY MED
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