US5410016A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Photopolymerizable biodegradable hydrogels as tissue contacting materials and controlled-release carriers
Assignee: The University of Texas System
•
Filing: 1993-03-01
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Granted: 1995-04-25
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Expires: 2013-03-01
Abstract
Abstract Hydrogels of polymerized and crosslinked macromers comprising hydrophilic oligomers having biodegradable monomeric or oligomeric extensions, which biodegradable extensions are terminated on free ends with end cap monomers or oligomers capable of polymerization and cross linking are described. The hydrophilic core itself may be degradable, thus combining the core and extension functions. Macromers are polymerized using free radical initiators under the influence of long wavelength ultraviolet light, visible light excitation or thermal energy. Biodegradation occurs at the linkages within the extension oligomers and results in fragments which are non-toxic and easily removed from the body. Preferred applications for the hydrogels include prevention of adhesion formation after surgical procedures, controlled release of drugs and other bioactive species, temporary protection or separation of tissue surfaces, adhering of sealing tissues together, and preventing the attachment of cells to tissue surfaces.
Inventors
- 👤 Jeffrey A. Hubbell
- 👤 Chandrashekhar P. Pathak
- 👤 Amarpreet S. Sawhney
- 👤 Neil P. Desai
- 👤 Jennifer L. Hill
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 07:58
CPC Classifications
C; C08; C08F; C08F290/00; C08F290/02; C08F290/06; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/62; A61K47/64; A61K47/645; A61K47/69; A61K47/6903; A61K47/6921; A61K47/6927; A61K9/00; A61K9/14; A61K9/16; A61K9/1605; A61K9/1629; A61K9/1635; A61K9/1641; A61K9/1647; A61K9/48; A61K9/50; A61K9/5005; A61K9/5021; A61K9/5031; A61K9/5073; A61L; A61L24/00; A61L24/001; A61L24/0031; A61L24/0042; A61L24/04; A61L24/046; A61L27/00; A61L27/28; A61L27/34; A61L27/36; A61L27/38; A61L27/50; A61L27/52; A61L29/00; A61L29/08; A61L29/085; A61L31/00; A61L31/14; A61L31/145; A61L31/148; C08F291/00; C09; C09D; C09D153/00; C12; C12N; C12N11/00; C12N11/02; C12N11/04; C12N5/00; C12N5/0012; C12N5/06; C12N5/0602; C12N5/0676; C12N5/0677; A61K35/00; A61K35/12; A61K2035/126; A61K2035/128; C12N2533/00; C12N2533/30; C12N2533/32; C12N2533/40; C12N2533/70; C12N2533/74
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
71 words
A biodegradable, polymerizable macromer having a solubility of at least about 1 g/100 ml in an aqueous solution comprising at least one water soluble region, at least one degradable region which is hydrolyzable under in vivo conditions, and free radical polymerizable end groups having the capacity to form additional covalent bonds resulting in macromer interlinking, wherein the polymerizable end groups are separated from each other by at least one degradable region.
Claim 2
Dependent Claim
71 words
A biodegradable, polymerizable macromer having a solubility of at least about 1 g/100 ml in an aqueous solution comprising at least one water soluble region, at least one degradable region which is hydrolyzable under in vivo conditions, and free radical polymerizable end groups having the capacity to form additional covalent bonds resulting in macromer interlinking, wherein the polymerizable end groups are separated from each other by at least one degradable region.
Claim 3
Dependent Claim
42 words
The macromer of claim 1 wherein the water soluble region is attached to a degradable region, at least one polymerizable end group is attached to the water soluble region, and at least one polymerizable end group is attached to the degradable region.
Claim 4
Dependent Claim
35 words
The macromer of claim 1 wherein the water soluble region forms a central core, at least two degradable regions are attached to the core, and the polymerizable end groups are attached to the degradable regions.
Claim 5
Dependent Claim
36 words
The macromer of claim 2 wherein the degradable region is a central core, at least two water soluble regions are attached to the core, and a polymerizable end group is attached to each water soluble region.
Claim 6
Dependent Claim
37 words
The macromer of claim 1 wherein the water soluble region is a macromer backbone, the degradable region is a branch or graft attached to the macromer backbone, and polymerizable end groups are attached to the degradable regions.
Claim 7
Dependent Claim
40 words
The macromer of claim 1 wherein the degradable region is a macromer backbone, the water soluble region is a branch or graft attached to the degradable backbone, and polymerizable end groups are attached to the water soluble branches or grafts.
Claim 8
Dependent Claim
44 words
The macromer of claim 1 wherein the water soluble region is a star backbone, the degradable region is a branch or graft attached to the water soluble star backbone, and at least two polymerizable end groups are attached to a degradable branch or graft.
Claim 9
Dependent Claim
44 words
The macromer of claim 1 wherein the degradable region is a star backbone, the water soluble region is a branch or graft attached to the degradable star backbone, and two or more polymerizable end groups are attached to the water soluble branch or graft.
Claim 10
Dependent Claim
15 words
The macromer of claim 1 wherein the water soluble region is also the degradable region.
Claim 11
Dependent Claim
30 words
The macromer of claim 1 wherein the water soluble region is also the degradable region, one or more additional degradable regions are grafts or branches upon the water soluble region.
Claim 12
Dependent Claim
53 words
The macromer of claim 1 comprising a water soluble core region, at least two degradable extensions on the core, and an end cap on at least two of the degradable extensions, wherein the core comprises poly(ethylene glycol); each extension comprises biodegradable poly(α-hydroxy acid); and each end cap comprises an acrylate oligomer or monomer.
Claim 13
Dependent Claim
22 words
The macromer of claim 11 wherein each extension comprises biodegradable poly(hydroxy acid); and each end cap comprises an acrylate oligomer or monomer.
Claim 14
Dependent Claim
49 words
The macromer of claim 12 wherein the poly(ethylene glycol) has a molecular weight between about 400 and 30,000 Da; the poly(hydroxy acid) oligomers have a molecular weight between about 200 and 1200 Da; and the acrylate oligomer or monomer have a molecular weight between about 50 and 200 Da.
Claim 15
Dependent Claim
21 words
The macromer of claim 1 wherein the polymerizable end groups contain a carbon-carbon double bond capable of cross-linking and polymerizing macromers.
Claim 16
Dependent Claim
33 words
The macromer of claim 1 wherein crosslinking and polymerization of the macromer can be initiated by a light-sensitive free-radical polymerization initiator with or without a cocatalyst, further comprising a free radical polymerization initiator.
Claim 17
Dependent Claim
28 words
The macromer of claim 15 wherein the initiator is selected from the group consisting of xanthine dyes, acridine dyes, thiazine dyes, phenazine dyes, camphorquinone dyes, and acetophenone dyes.
Claim 18
Dependent Claim
25 words
The macromer of claim 16 wherein the initiator is selected from the group consisting of an eosin dye with triethanolamine, 2,2-dimethyl-2-phenyl acetophenone, and 2-methoxy-2-phenyl acetophenone.
Claim 19
Dependent Claim
24 words
The macromer of claim 1 wherein crosslinking or polymerizations can be initiated in situ by light having a wavelength of 320 nm or longer.
Claim 20
Dependent Claim
27 words
The macromer of claim 1 wherein the degradable region is selected from the group consisting of poly (hydroxy acids), poly(lactones), poly(amino acids), poly(anhydrides), poly(orthoesters), poly(phosphazines), and poly(phosphoesters).
Claim 21
Dependent Claim
26 words
The macromer of claim 19 wherein the degradable region is a poly(α-hydroxy acid) selected from the group consisting of poly(glycolic acid), poly(DL-lactic acid) and poly(L-lactic acid).
Claim 22
Dependent Claim
20 words
The macromer of claim 19 wherein the poly(lactone) is selected from the group consisting of poly(ε-caprolactone), poly (δ-valerolactone) or poly(λ-butyrolactone).
Claim 23
Dependent Claim
35 words
The macromer of claim 1 wherein the water soluble region is selected from the group consisting of poly(ethylene glycol), poly(ethylene oxide), poly(vinyl alcohol), poly(vinylpyrrolidone), poly(ethyloxazoline), poly(ethylene oxide)-copoly(propyleneoxide) block copolymers, polysaccharides, carbohydrates, proteins, and combinations thereof.
Claim 24
Dependent Claim
31 words
The macromer of claim 1 further comprising biologically active molecules selected from the group consisting of proteins, carbohydrates, nucleic acids, organic molecules, inorganic biologically active molecules, cells, tissues, and tissue aggregates.
References Cited (Backward Citations)
US3640741A
Cited
DE2232839A1
Cited
US3960150A
Cited
US3981303A
Cited
US3986510A
Cited
US3993071A
Cited
US3925895A
Cited
US4450150A
Cited
US4193845A
Cited
US4080969A
Cited
US4194066A
Cited
US4076800A
Cited
US4226938A
Cited
US4195129A
Cited
US4272617A
Cited
US4118470A
Cited
US4095600A
Cited
JPS5589314A
Cited
US4310397A
Cited
US4295762A
Cited
US4409331A
Cited
US4352883A
Cited
US4391909A
Cited
JPS5611916A
Cited
JPS5622306A
Cited
US4298002A
Cited
US4376839A
Cited
JPS56151701A
Cited
JPS56142038A
Cited
US4434150A
Cited
US4512910A
Cited
US4526938A
Cited
US4942035A
Cited
US4452973A
Cited
JPS59184029A
Cited
JPS59191750A
Cited
US4689293A
Cited
US4806355A
Cited
US4533445A
Cited
JPS6028950A
Cited
US4511478A
Cited
US4605622A
Cited
JPS60127342A
Cited
US4655777A
Cited
US4563489A
Cited
US4663286A
Cited
US4744933A
Cited
US4749620A
Cited
US4744178A
Cited
US4650488A
Cited
US4636552A
Cited
US4745160A
Cited
JPS6132271A
Cited
US4637931A
Cited
EP0195304A2
Cited
US4950596A
Cited
JPS61211372A
Cited
US4741337A
Cited
JPS62115012A
Cited
JPS62129376A
Cited
US4808399A
Cited
US4889722A
Cited
US5061281A
Cited
US4741872A
Cited
US4744365A
Cited
US4716203A
Cited
US4957744A
Cited
US4913903A
Cited
JPS63199208A
Cited
US4933430A
Cited
JPS63260972A
Cited
DE3716544A1
Cited
US4826945A
Cited
US4804691A
Cited
US5129889A
Cited
JPH01145139A
Cited
US4916193A
Cited
US5185408A
Cited
US4891263A
Cited
US5120802A
Cited
US4921934A
Cited
US4888413A
Cited
US4925677A
Cited
US5278201A
Cited
US5278202A
Cited
US4938763A
Cited
US4938763B1
Cited
US5135751A
Cited
DD277454A1
Cited
US5258034A
Cited
US4999417A
Cited
US5108755A
Cited
EP0399441A2
Cited
US4994277A
Cited
US5049138A
Cited
US5219564A
Cited
EP0466648A1
Cited
US5206303A
Cited
US5153002A
Cited
US5318780A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1998-04-24 | 1998-10-24 | 1999-04-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-04-24 | 2002-10-24 | 2003-04-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-04-24 | 2006-10-24 | 2007-04-25 | $7700.00 | Window Closed / Lapsed |