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US RE46,234 E1Granted
Tissue adhesive and sealant comprising polyglycerol aldehyde
AssigneeActamax Surgical Materials, LLC
InventorHenry Keith Chenault
Life of this patent
Estimating the term…
Abstract
A tissue adhesives and sealant formed by reacting a polyglycerol aldehyde with a water-dispersible, multi-arm amine is described. The tissue adhesive and sealant may be useful for medical and veterinary applications, including, but not limited to, wound closure, supplementing or replacing sutures or staples in internal surgical procedures such as intestinal anastomosis and vascular anastomosis, tissue repair, preventing leakage of fluids such as blood, bile, gastrointestinal fluid and cerebrospinal fluid, ophthalmic procedures, drug delivery, and to prevent post-surgical adhesions.
Claims23
A kit comprising:
- a) at least one polyglycerol aldehyde having aldehyde groups, said polyglycerol aldehyde having a number-average molecular weight of about 400 1,000 to about 20,000 Daltons and the general formula:
- wherein;
- A is either (a) a hydrocarbyl group derived by removing on one or more hydroxyl groups from an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups or (b) an oxahydrocarbyl or polyoxahydrocarbyl group derived by removing or or more hydroxyl groups from the reaction product of (I) an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups and (II) one or more cyclic ethers, wherein the Mn of the reaction product is less than or equal to 5,000 Da;
- R1 is a hydrogen atom, a 1 to 8-carbon hydrocarbyl group, R2—O—[R3—CHO]p R2—[O—R3—CHO]p, or R3—CHO;
- R2 is a polymeric segment comprising 1 to 270 glycerol units connected by ether linkages, wherein each —[O—R3—CHO]p, or —[O—R3—CHO]m group is attached directly to R2 by a carbon-oxygen single bond, and wherein no carbon atom that bears an —[O—R3—CHO]p, or —[O—R3—CHO]m group also bears a hydroxyl group, a second —[O—R3—CHO]p, or —[O—R3—CHO]m group, or a bond to a second oxygen atom;
- R3 is a hydrocarbylene group containing 1 to 8 carbon atoms;
- n=1 to 8;
- m*n=3 to 170;
- and p=1 to 40, wherein n, m and p are intergers;
- and an equivalent weight per aldehyde group of about 100 to about 3,000 Daltons;
- and
- b) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by at least one primary amine group, wherein the multi-arm amine has a number-average molecular weight of about 450 to about 200,000 Daltons.
9 more elements
A dried hydrogel formed by a process comprising the steps of:
- a) combining in a solvent (i) at least one polyglycerol aldehyde having aldehyde groups, said polyglycerol aldehyde having a number-average molecular weight of about 400 1,000 to about 20,000 Daltons and the general formula:
- wherein:
- A is either (a) a hydrocarbyl group derived by removing on one or more hydroxyl groups from an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups or (b) an oxahydrocarbyl or polyoxahydrocarbyl group derived by removing or or more hydroxyl groups from the reaction product of (I) an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups and (II) one or more cyclic ethers, wherein the Mn of the reaction product is less than or equal to 5,000 Da;
- R1 is a hydrogen atom, a 1 to 8-carbon hydrocarbyl group, R2—O—[R3—CHO]p R2—[O—R3—CHO]p, or R3—CHO;
- R2 is a polymeric segment comprising 1 to 270 glycerol units connected by ether linkages, wherein each —[O—R3—CHO]p, or —[O—R3—CHO]m group is attached directly to R2 by a carbon-oxygen single bond, and wherein no carbon atom that bears an —[O—R3—CHO]p, or —[O—R3—CHO]m group also bears a hydroxyl group, a second —[O—R3—CHO]p, or —[O—R3—CHO]m group, or a bond to a second oxygen atom;
- R3 is a hydrocarbylene group containing 1 to 8 carbon atoms;
- n=1 to 8;
- m*n=3 to 170;
- and p=1 to 40, wherein n, m and p are intergers;
- and an equivalent weight per aldehyde group of about 100 to about 3,000 Daltons;
- with (ii) at least one water-dispersible, multi-arm amine, wherein at least three of the arms are terminated by at least one primary amine group, said multi-arm amine having a number-average molecular weight of about 450 to about 200,000 Daltons, to forma hydrogel;
- and
- b) treating said hydrogel to remove at least a portion of said solvent to form the dried hydrogel.
10 more elements
A composition comprising the reaction product of:
- a) at least one polyglycerol aldehyde having aldehyde groups, said polyglycerol aldehyde having a number-average molecular weight of about 400 1,000 to about 20,000 Daltons and the general formula:
- wherein;
- A is either (a) a hydrocarbyl group derived by removing on or more hydroxyl groups from an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups or (b) an oxahydrocarbyl or polyoxahydrocarbyl group derived by removing or or more hydroxyl groups from the reaction product of (I) an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups and (II) one or more cyclic ethers, wherein the Mn of the reaction product is less than or equal to 5,000 Da;
- R1 is a hydrogen atom, a 1 to 8-carbon hydrocarbyl group, R2—O—[R3—CHO]p R2—[O—R3—CHO]p, or R3—CHO;
- R2 is a polymeric segment comprising 1 to 270 glycerol units connected by ether linkages, wherein each —[O—R3—CHO]p, or —[O—R3—CHO]m group is attached directly to R2 by a carbon-oxygen single bond, and wherein no carbon atom that bears an —[O—R3—CHO]p, or —[O—R3—CHO]m group also bears a hydroxyl group, a second —[O—R3—CHO]p, or —[O—R3—CHO]m group, or a bond to a second oxygen atom;
- R3 is a hydrocarbylene group containing 1 to 8 carbon atoms;
- n=1 to 8;
- m*n=3 to 170;
- and p=1 to 40, wherein n, m and p are intergers;
- and an equivalent weight per aldehyde group of about 100 to about 3,000 Daltons;
- and
- b) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by at least one primary amine group, said multi-arm amine having a number-average molecular weight of about 450 to about 200,000 Daltons.
9 more elements
A crosslinked hydrogel composition comprising:
- a) at least one polyglycerol aldehyde having aldehyde groups, said polyglycerol aldehyde having a number-average molecular weight of about 400 1,000 to about 20,000 Daltons and the general formula:
- wherein:
- A is either (a) a hydrocarbyl group derived by removing on or more hydroxyl groups from an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups or (b) an oxahydrocarbyl or polyoxahydrocarbyl group derived by removing or or more hydroxyl groups from the reaction product of (I) an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups and (II) one or more cyclic ethers, wherein the Mn of the reaction product is less than or equal to 5,000 Da;
- R1 is a hydrogen atom, a 1 to 8-carbon hydrocarbyl group, R2—O—[R3—CHO]p R2—[O—R3—CHO]p, or R3—CHO;
- R2 is a polymeric segment comprising 1 to 270 glycerol units connected by ether linkages, wherein each —[O—R3—CHO]p, or —[O—R3—CHO]m group is attached directly to R2 by a carbon-oxygen single bond, and wherein no carbon atom that bears an —[O—R3—CHO]p, or —[O—R3—CHO]m group also bears a hydroxyl group, a second —[O—R3—CHO]p, or —[O—R3—CHO]m group, or a bond to a second oxygen atom;
- R3 is a hydrocarbylene group containing 1 to 8 carbon atoms;
- n=1 to 8;
- m*n=3 to 170;
- and p=1 to 40, wherein n, m and p are intergers;
- and an equivalent weight per aldehyde group of about 100 to about 3,000 Daltons;
- and
- b) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by at least one primary amine group, said multi-arm amine having a number-average molecular weight of about 450 to about 200,000 Daltons;
- wherein said at least one polyglycerol aldehyde and said at least one water-dispersible, multi-arm amine are crosslinked through covalent bonds formed between the aldehyde groups of the polyglycerol aldehyde and the primary amine groups of the water-dispersible, multi-arm amine.
10 more elements
A method for applying a coating to an anatomical site on tissue of a living organism comprising:
- applying to the site a) at least one polyglycerol aldehyde having aldehyde groups, said polyglycerol aldehyde having a number-average molecular weight of about 400 1,000 to about 20,000 Daltons and the general formula:
- wherein:
- A is either (a) a hydrocarbyl group derived by removing on or more hydroxyl groups from an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups or (b) an oxahydrocarbyl or polyoxahydrocarbyl group derived by removing or or more hydroxyl groups from the reaction product of (I) an alcohol or polyol containing 1 to 20 carbon atoms and 1 to 8 hydroxyl groups and (II) one or more cyclic ethers, wherein the Mn of the reaction product is less than or equal to 5,000 Da;
- R1 is a hydrogen atom, a 1 to 8-carbon hydrocarbyl group, R2—O—[R3—CHO]p R2—[O—R3—CHO]p, or R3—CHO;
- R2 is a polymeric segment comprising 1 to 270 glycerol units connected by ether linkages;
- wherein each —[O—R3—CHO]p, or —[O—R3—CHO]m group is attached directly to R2 by a carbon-oxygen single bond, and wherein no carbon atom that bears an —[O—R3—CHO]p, or —[O—R3—CHO]m group also bears a hydroxyl group, a second —[O—R3—CHO]p, or —[O—R3—CHO]m group, or a bond to a second oxygen atom;
- R3 is a hydrocarbylene group containing 1 to 8 carbon atoms;
- n=1 to 8;
- m*n=3 to 170;
- and p=1 to 40, wherein n, m and p are intergers;
- and an equivalent weight per aldehyde group of about 100 to about 3,000 Daltons;
- followed by b) at least one water-dispersible, multi-arm amine wherein at least three of the arms are terminated by a primary amine group, said multi-arm amine having a number-average molecular weight of about 450 to about 200,000 Daltons,
- or (b) followed by (a), or premixing (a) and (b);
- and applying the resulting mixture to the site before the resulting mixture completely cures.
11 more elements
Dependencies are inferred from the claim text.