Method comprising contacting tissue with a cross-linkable polyester prepolymer

• US 10,179,195 B2
• Filed: 02/17/2014
• Issued: 01/15/2019
• Est. Priority Date: 01/12/2006
• Status: Active Grant

• Current Assignee: Massachusetts Institute of Technology
• Original Assignee: Massachusetts Institute of Technology
• Inventors: Bettinger, Christopher J., Bruggeman, Joost P., Ferreira, Lino da Silva, Karp, Jeffrey M., Langer, Robert S., Nijst, Christiaan, Zumbuehl, Andreas, Burdick, Jason, Kim, Sonia J.
• Primary Examiner(s): Choi, Ling Siu
• Assistant Examiner(s): Nguyen, Thuy-Ai N
• Application Number:
  US14/182,095
• Publication Number:
  US 20140186312A1
• Time in Patent Office: 1,793 Days
• Field of Search: 528271
• CPC Class Codes: A61K 35/12 Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells vaccines or medicinal preparations containing antigens or antibodies A61K39/00
• CPC Class Codes: A61K 35/48 Reproductive organs
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/38 containing added animal cells organs or tissue containing native cells A61L27/36
• CPC Class Codes: A61L 27/3804 characterised by specific cells or progenitors thereof, e.g. fibroblasts, connective tissue cells, kidney cells
• CPC Class Codes: A61L 27/58 Materials at least partially resorbable by the body
• CPC Class Codes: A61L 31/06 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds A61L31/041 takes precedence
• CPC Class Codes: A61L 31/148 Materials at least partially resorbable by the body
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: C08G 63/6854 derived from polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08J 2367/00 Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
• CPC Class Codes: C08J 2367/07 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: C08J 3/246 Intercrosslinking of at least two polymers
• CPC Class Codes: C08K 5/0025 Crosslinking or vulcanising agents; including accelerators
• CPC Class Codes: C08L 67/00 Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 67/07 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C12N 11/082 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C12N 11/087 Acrylic polymers
• CPC Class Codes: C12N 11/096 : Polyesters; Polyamides

Abstract

The present inventions in various aspects provide elastic biodegradable polymers. In various embodiments, the polymers are formed by the reaction of a multifunctional alcohol or ether and a difunctional or higher order acid to form a pre-polymer, which is cross-linked to form the elastic biodegradable polymer. In preferred embodiments, the cross-linking is performed by functionalization of one or more OR groups on the pre-polymer backbone with vinyl, followed by photopolymerization to form the elastic biodegradable polymer composition or material. Preferably, acrylate is used to add one or more vinyls to the backbone of the pre-polymer to form an acrylated pre-polymer. In various embodiments, acrylated pre-polymers are co-polymerized with one or more acrylated co-polymers.

Claims

1. A polyester composition comprising a plurality of polyester polymeric backbones of general formula (-A-B—

)_n, comprising A and B components, wherein n is an integer greater than 1, and wherein the polymeric backbones are formed by reaction of;

the A component which is a compound having two or more —

OR groups wherein each R is independently selected from hydrogen or an alkyl group; and

the B component which is a diacid compound;

wherein one or more of the —

OR groups within the polyester polymeric backbones is functionalized with a vinyl-containing moiety prior to crosslinking;

wherein crosslinking the vinyl-containing moieties within the polyester polymeric backbones forms crosslinks between the plurality of the polyester polymeric backbones, the crosslinks containing a dioic acid ester functionality,

wherein the polyester composition when crosslinked is an adhesive elastomeric polymer, and

wherein the polyester composition when crosslinked is non-toxic to humans, biocompatible, and bioabsorbable.

2. The polyester composition of claim 1, wherein the R of the —

OR groups of the compound is hydrogen.

3. The polyester composition of claim 1, wherein the compound is glycerol.

4. The polyester composition of claim 1, wherein the diacid compound is selected from the group consisting of glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid.

5. The polyester composition of claim 1, wherein the vinyl-containing moiety is derived from a molecule selected from the group consisting of

6. The polyester composition of claim 1, wherein the vinyl-containing moiety is derived from acryloyl chloride.

7. The polyester composition of claim 1, wherein the crosslink density of the crosslinked polyester composition is less than 1%.

8. The polyester composition of claim 7, wherein the crosslink density of the crosslinked polyester composition is less than 0.5%.

9. The polyester composition of claim 7, wherein the crosslink density of the crosslinked polyester composition is less than 0.05%.

10. The polyester composition of claim 1, wherein the polyester polymeric backbones of general formula (-A-B—

)_n wherein the one or more of the —

OR groups within the polyester polymeric backbones are functionalized with the vinyl-containing moiety prior to crosslinking have a structure as follows;