US5100992A
Expired / Lapsed
US
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Polyurethane-based polymeric materials and biomedical articles and pharmaceutical compositions utilizing the same
Assignee: Biomedical Polymers International Ltd
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Filing: 1990-05-03
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Granted: 1992-03-31
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Expires: 2010-05-03
Abstract
Abstract The invention provides a polyurethane amide segmented copolymer selected from: a) a segmented block polyurethane amide (PEUAm) of the following repeating unit [I] ##STR1## b) a segmented block polyurethane amide of the following repeating unit [II] ##STR2##
Inventors
- 👤 Daniel Cohn
- 👤 Shlomo Yitzchaiek
- 👤 Sophie Bilenkis
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 02:39
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/69; C08G18/692; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/56; A61K47/58; A61K47/59; A61K47/595; A61L; A61L15/00; A61L15/16; A61L15/22; A61L15/26; A61L27/00; A61L27/14; A61L27/18; A61L29/00; A61L29/04; A61L29/06; A61L31/00; A61L31/04; A61L31/06; C08G18/08; C08G18/10; C08G18/40; C08G18/48; C08G18/4825; C08G18/4854; C08G18/675; C08G18/6755
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
346 words
A polyurethane amide segmented copolymer selected from: a) a segmented block polyurethane amide (PEUAm) of the following repeating unit [I] ##STR11## wherein R is hexamethylene, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethyl-hexamethylene or p-phenylene, R' is selected from a linear or branched, unsubstituted or substituted hydrocarbyl group, said substituents being selected from halogen or hydroxy, or R' is a bivalent Si--(R 1 R 2 ) group, wherein R 1 and R 2 are identical or different groups selected from hydrogen, alkyl, a double bond-containing hydrocarbyl group, halogen, hydroxy or an aromatic ring-containing group, and m is a positive integer, A is a bivalent saturated or unsaturated, linear or branched, substituted or unsubstituted hydrocarbyl group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups; or A is an unsubstituted or substituted aromatic ring-containing group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, and n is zero or a positive integer: b) a segmented block polyurethane amide of the following repeating unit [II] ##STR12## wherein R is hexamethylene. 4,4'-diphenylmethane, toluene, naphthalen, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethyl-hexamethylene or p-phenylene, R' is selected from a linear or branched, unsubstituted or substituted hydrocarbyl group, said substitutents being selected from halogen or hydroxy, or R' is a bivalent Si--(R 1 R 2 ) group, wherein R 1 and R 2 are identical or different groups selected from hydrogen, alkyl, a double bond-containing hydrocarbyl group, halogen, hydroxy or an aromatic ring-containing group, and m is a positive integer and B and D are each a bivalent, saturated or unsaturated, linear or branched, unsubstituted or substituted hydrocarbyl group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, or B and D are each an unsubstituted or substituted aromatic ring-containing group, said substituents being selected from halogen, cyano, carboxy or amino groups wherein B and D can be the same or different, and a and b are identical or different and are each 0 or 1, and X and Y are identical or different grafted substituents, usually bearing biomedical relevance.
Claim 2
Dependent Claim
346 words
A polyurethane amide segmented copolymer selected from: a) a segmented block polyurethane amide (PEUAm) of the following repeating unit [I] ##STR11## wherein R is hexamethylene, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethyl-hexamethylene or p-phenylene, R' is selected from a linear or branched, unsubstituted or substituted hydrocarbyl group, said substituents being selected from halogen or hydroxy, or R' is a bivalent Si--(R 1 R 2 ) group, wherein R 1 and R 2 are identical or different groups selected from hydrogen, alkyl, a double bond-containing hydrocarbyl group, halogen, hydroxy or an aromatic ring-containing group, and m is a positive integer, A is a bivalent saturated or unsaturated, linear or branched, substituted or unsubstituted hydrocarbyl group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups; or A is an unsubstituted or substituted aromatic ring-containing group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, and n is zero or a positive integer: b) a segmented block polyurethane amide of the following repeating unit [II] ##STR12## wherein R is hexamethylene. 4,4'-diphenylmethane, toluene, naphthalen, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethyl-hexamethylene or p-phenylene, R' is selected from a linear or branched, unsubstituted or substituted hydrocarbyl group, said substitutents being selected from halogen or hydroxy, or R' is a bivalent Si--(R 1 R 2 ) group, wherein R 1 and R 2 are identical or different groups selected from hydrogen, alkyl, a double bond-containing hydrocarbyl group, halogen, hydroxy or an aromatic ring-containing group, and m is a positive integer and B and D are each a bivalent, saturated or unsaturated, linear or branched, unsubstituted or substituted hydrocarbyl group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, or B and D are each an unsubstituted or substituted aromatic ring-containing group, said substituents being selected from halogen, cyano, carboxy or amino groups wherein B and D can be the same or different, and a and b are identical or different and are each 0 or 1, and X and Y are identical or different grafted substituents, usually bearing biomedical relevance.
Claim 3
Dependent Claim
157 words
A polyurethane amide segmented copolymer useful for the manufacture of biomedical articles, having a general repeating unit [I] ##STR13## wherein R is hexamethylene, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethyl-hexamethylene or p-phenylene, R' is selected from a linear or branched, unsubstituted or substituted hydrocarbyl group, said substituents being selected from halogen or hydroxy, or R' is a bivalent Si--(R 1 R 2 ) group, wherein R 1 and R 2 are identical or different groups selected from hydrogen, alkyl, a double bond-containing hydrocarbyl group, halogen, hydroxy or an aromatic ring-containing group, and m is a positive integer, A is a bivalent saturated or unsaturated, linear or branched, substituted or unsubstituted hydrocarbyl group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, or A is an unsubstituted or substituted aromatic ring-containing group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, and n is zero or a positive integer.
Claim 4
Dependent Claim
157 words
A polyurethane amide segmented copolymer useful for the manufacture of biomedical articles, having a general repeating unit [I] ##STR13## wherein R is hexamethylene, 4,4'-diphenylmethane, toluene, naphthalene, 4,4'-dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethyl-hexamethylene or p-phenylene, R' is selected from a linear or branched, unsubstituted or substituted hydrocarbyl group, said substituents being selected from halogen or hydroxy, or R' is a bivalent Si--(R 1 R 2 ) group, wherein R 1 and R 2 are identical or different groups selected from hydrogen, alkyl, a double bond-containing hydrocarbyl group, halogen, hydroxy or an aromatic ring-containing group, and m is a positive integer, A is a bivalent saturated or unsaturated, linear or branched, substituted or unsubstituted hydrocarbyl group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, or A is an unsubstituted or substituted aromatic ring-containing group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, and n is zero or a positive integer.
Claim 5
Dependent Claim
205 words
A polyurethane amide segmented copolymer useful for the manufacture of biomedical articles, having a general repeating unit [II] b) a segmented block polyurethane of the following repeating unit [II] ##STR14## wherein R is hexamethylene, 4,4'-diphenylmethane, toluene, naphthalene, 4,4' dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethyl-hexamethylene or p-phenylene, R is selected from a linear or branched, unsubstituted or substituted hydrocarbyl group, said substitutents being selected from halogen or hydroxy, or R' is a bivalent Si--(R 1 R 2 ) group, wherein R 1 and R 2 are identical or different groups selected from hydrogen, alkyl, a double bond-containing hydrocarbyl group, halogen, hydroxy or an aromatic ring-containing group, and m is a positive integer and B and D are each a bivalent, saturated or unsaturated, linear or branched, unsubstituted or substituted hydrocarbyl group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, or B and D are each an unsubstituted or substituted aromatic ring-containing group, said substituents being selected from halogen, cyano, carboxy or amino groups wherein B and D can be the same or different, and a and b are identical or different and are each 0 or 1, and X and Y are identical or different grafted substituents, usually bearing biomedical relevance.
Claim 6
Dependent Claim
205 words
A polyurethane amide segmented copolymer useful for the manufacture of biomedical articles, having a general repeating unit [II] b) a segmented block polyurethane of the following repeating unit [II] ##STR14## wherein R is hexamethylene, 4,4'-diphenylmethane, toluene, naphthalene, 4,4' dicyclohexylmethane, cyclohexyl, 3,3'-dimethylphenyl, 3,3'-dimethyl-diphenylmethane, 4,6'-xylylene, 3,5,5-trimethylcyclohexyl, 2,2,4-trimethyl-hexamethylene or p-phenylene, R is selected from a linear or branched, unsubstituted or substituted hydrocarbyl group, said substitutents being selected from halogen or hydroxy, or R' is a bivalent Si--(R 1 R 2 ) group, wherein R 1 and R 2 are identical or different groups selected from hydrogen, alkyl, a double bond-containing hydrocarbyl group, halogen, hydroxy or an aromatic ring-containing group, and m is a positive integer and B and D are each a bivalent, saturated or unsaturated, linear or branched, unsubstituted or substituted hydrocarbyl group, said substituents being selected from halogen, hydroxy, cyano, carboxy or amino groups, or B and D are each an unsubstituted or substituted aromatic ring-containing group, said substituents being selected from halogen, cyano, carboxy or amino groups wherein B and D can be the same or different, and a and b are identical or different and are each 0 or 1, and X and Y are identical or different grafted substituents, usually bearing biomedical relevance.
Claim 7
Dependent Claim
40 words
A polyurethane amide segmented copolymer as claimed in claim 1 wherein X and Y are the same or different and each is a monomer selected from 2-hydroxyethyl methacrylate, acrylic acid, acrylamide, methyl methacrylate, pentafluorobutyl acrylate, pentamethyl disiloxanylmethyl methacrylate or acrylonitrile.
Claim 8
Dependent Claim
33 words
A polyurethane amide segmented copolymer as claimed in claim 1 wherein X and Y are the same or different and each is a polyethylene glycol chain which prevents irreversible protein adsorption on surfaces.
Claim 9
Dependent Claim
43 words
A polyurethane amide segmented copolymer as claimed in claim 1 wherein X and Y are the same or different and each is a poly(amido-amine) chain which renders the system with enhanced blood compatibility due to its ability to form stable complexes with heparin.
Claim 10
Dependent Claim
39 words
A polyurethane amide segmented copolymer as claimed in claim 1 wherein X and Y are the same or different and each is a C 16 or C 18 alkyl chain, the resulting surface being characterized by selective albumin affinity.
Claim 11
Dependent Claim
19 words
A polyurethane amide segmented copolymer as claimed in claim 2 where R is selected from hexamethylene. 4,4'-diphenylmethane or 4,4'-dicyclohexylmethane.
Claim 12
Dependent Claim
28 words
A polyurethane amide segmented copolymer as claimed in claim 2 where R' is selected from butylene, ethylene, propylene, a Si--(CH 3 ) 2 group, perfluorobutylene, polybutadiene or polyisobutylene.
Claim 13
Dependent Claim
36 words
A polyurethane amide segmented copolymer as claimed in claim 2 where the chain extender is selected from oxalic acid, succinic acid, adipic acid, suberic acid, sebacic acid, maleic acid, fumaric acid, terephthalic acid, or trans-beta-hydromuconic acid.
Claim 14
Dependent Claim
19 words
A polyurethane amide segmented copolymer as claimed in claim 3 where R is selected from hexamethylene, 4,4'-diphenylmethane or 4,4'-dicyclohexylmethane.
Claim 15
Dependent Claim
24 words
A polyurethane amide segmented copolymer as claimed in claim 3 where R' is butylene, ethylene, propylene, Si--(CH 3 ) 2 , perflurobutylene, polybutadiene, polyisobutylene.
Claim 16
Dependent Claim
24 words
A polyurethane amide segmented copolymer as claimed in claim 3 where the chain extender is selected from maleic acid, fumaric acid or trans-beta-hydromuconic acid.
Claim 17
Dependent Claim
68 words
A polyurethane amide segmented copolymer as claimed in claim 3 where X and Y are the same or different and each is selected from poly(2-hydroxyethyl methacrylate) chains, polyacrylamide chains, polymethyl methacrylate chains, polyacrylic acid chains, poly(perfluoroalkyl methacrylate) chains, poly(pentamethyl disiloxanylmethyl methacrylate) chains, amino-terminated polyethylene oxide chains, hexadecane or octadecane chains, poly)amido-amine) chains or from biodegradable chains selected from polyglycolic acid, polyactic acid or polyethylene glycol/polylactic acid block copolymers.
Claim 18
Dependent Claim
38 words
A polyurethane amide segmented copolymer as claimed in claim 14 where the grafted chains perform as spacers for binding biologically active molecules selected from enzymes, antibiotics and anti-thrombogenic agents, onto the surface and/or bulk of the polymeric system.
Claim 19
Dependent Claim
59 words
A polyurethane amide segmented copolymer as claimed in claim 3 wherein X and Y are the same or different and each is a biodegradably polyglycolic acid, polylactic acid or polyethylene glycol/polylactic acid block copolymer, temporarily bound to a biologically active molecule selected from an enzyme, antibiotic, hormone, or anti-thrombogenic agent whereby the system performs as a controlled delivery system.
Claim 20
Dependent Claim
22 words
A polyurethane amide segmented copolymer as claimed in claim 1 wherein said copolymer is in the form of at least one filament.
Claim 21
Dependent Claim
67 words
A biomedical article selected from the group consisting of a suture, ligature, needle and suture combination, surgical prosthesis, film, membrane, textile structure, wound and burn dressing, coupling, tube, catheter, a vascular graft, oesophageal prosthesis, intra-aortic balloon, pacemaker lead, tracheal prosthesis, physical or biological support, screw or pin, where at least one of the components of each of said articles is a polymer as claimed in claim 1.
Claim 22
Dependent Claim
14 words
A compound vascular prosthesis comprising a Polymer or polymers as claimed in claim 1.
Claim 23
Dependent Claim
31 words
A compound vascular prosthesis comprising a component selected from polyethylene terephthalate, polyether esters, polydimethyl siloxane polymers or copolymers, biodegradable polyether esters and a polymer or polymers as claimed in claim 1.
Claim 24
Dependent Claim
26 words
A selectively biodegradable vascular prosthesis comprising an absorbable component in the form of biodegradable polyether esters and a polymer or polymers as claimed in claim 1.
Claim 25
Dependent Claim
18 words
A selectively biodegradable vascular prosthesis manufactured by textile and non-textile techniques, comprising polymers as claimed in claim 1.
Claim 26
Dependent Claim
15 words
A wound or burn dressing comprising a polymer or polymers as claimed in claim 1.
Claim 27
Dependent Claim
26 words
A selectively biodegradable wound or burn dressing comprising an absorbable component selected from biodegradable polyether esters and a polymer or polymers as claimed in claim 1.
Claim 28
Dependent Claim
34 words
A pharmaceutical composition comprising a self-supporting film, hollow fiber, beads or gel, manufactured from a polyurethane amide segmented copolymer or copolymers as claimed in claim 1 and containing a uniformly dispersed drug contained therein.
Claim 29
Dependent Claim
43 words
A pharmaceutical composition comprising a self-supporting film, hollow fiber, beads or gel, manufactured from a polyurethane amide segmented copolymer or copolymers as claimed in claim 1(b) and a drug grafted to the polyurethene amide backbone via a spacer selected among biodegradable polymeric chains.
References Cited (Backward Citations)
US4267299A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-03-31 | 1995-09-30 | 1996-03-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-03-31 | 1999-09-30 | 2000-03-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-03-31 | 2003-09-30 | 2004-03-31 | $7700.00 | Window Closed / Lapsed |