US5658995A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Copolymers of tyrosine-based polycarbonate and poly(alkylene oxide)
Assignee: Rutgers, The State University of New Jersey
•
Filing: 1995-11-27
•
Granted: 1997-08-19
•
Expires: 2015-11-27
Abstract
Abstract Random block copolymers having the formula: <IMAGE> +TR <IMAGE> wherein R1 is -CH=CH- or (-CH2-)j, in which j is zero or an integer from one to eight; R2 is selected from hydrogen, straight and branched alkyl and alkylaryl groups containing up to 18 carbon atoms and derivatives or biologically and pharmaceutically active compounds covalently bonded to said copolymer; each R3 is independently an alkylene group containing up to 4 carbon atoms; y is an integer between about 5 and about 3000; and f is the percent molar fraction of alkylene oxide in the copolymer and ranges between about 1 and about 99 mole percent. Implantable medical devices and drug delivery implants containing the random block copolymers are also disclosed, along with methods for drug delivery and for preventing the formation of adhesions between injured tissues employing the random block copolymers. Polyarylate random block copolymers are also described.
Inventors
- 👤 Joachim B. Kohn
- 👤 Chun Yu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:34
CPC Classifications
C; C08; C08L; C08L77/00; C08G; C08G64/00; C08G64/18; C08G64/183; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/56; A61K47/59; A61K47/60; A61K47/62; A61K47/64; C08G63/00; C08G63/68; C08G63/685; C08G63/6854; C08G63/6856; C08G64/16; C08G64/1608; C08G64/1625; C08G64/1641
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
111 words
A random block copolymer having the formula: ##STR5## wherein R 1 is --CH═CH-- or (--CH 2 --) j , in which j is zero or an integer from one to eight; R 2 is selected from the group consisting of straight and branched alkyl and alkylaryl groups containing up to 18 carbon atoms, and derivatives of biologically and physiologically active compounds covalently bonded to said copolymer; each R 3 is independently an alkylene group containing up to 4 carbon atoms; y is between about 5 and about 3000; and f is the percent molar fraction of alkylene oxide in said copolymer and ranges between about 1 and about 99 mole percent.
Claim 2
Dependent Claim
111 words
A random block copolymer having the formula: ##STR5## wherein R 1 is --CH═CH-- or (--CH 2 --) j , in which j is zero or an integer from one to eight; R 2 is selected from the group consisting of straight and branched alkyl and alkylaryl groups containing up to 18 carbon atoms, and derivatives of biologically and physiologically active compounds covalently bonded to said copolymer; each R 3 is independently an alkylene group containing up to 4 carbon atoms; y is between about 5 and about 3000; and f is the percent molar fraction of alkylene oxide in said copolymer and ranges between about 1 and about 99 mole percent.
Claim 3
Dependent Claim
16 words
The random block copolymer of claim 1, wherein R 1 is --CH 2 --CH 2 --.
Claim 4
Dependent Claim
27 words
The random block copolymer of claim 1, wherein R 2 is a straight-chained alkyl group selected from the group consisting of ethyl, butyl, hexyl and octyl groups.
Claim 5
Dependent Claim
14 words
The random block copolymer of claim 3, wherein R 2 is a hexyl group.
Claim 6
Dependent Claim
13 words
The random block copolymer of claim 1, wherein each R 3 is ethylene.
Claim 7
Dependent Claim
16 words
The random block copolymer of claim 1, wherein y is between about 20 and about 200.
Claim 8
Dependent Claim
18 words
The random block copolymer of claim 1, wherein f is between about 5 and about 95 mole percent.
Claim 9
Dependent Claim
12 words
An implantable medical device comprising the random block copolymer of claim 1.
Claim 10
Dependent Claim
20 words
The implantable medical device of claim 8, wherein the surface of said device is coated with said random block copolymer.
Claim 11
Dependent Claim
39 words
The implantable medical device of claim 8, comprising a biologically or physiologically active compound in combination with said random block copolymer, wherein said active compound is present in an amount sufficient for therapeutically effective site-specific or systemic drug delivery.
Claim 12
Dependent Claim
20 words
The implantable medical device of claim 10, wherein said biologically or physiologically active compound is covalently bonded to said copolymer.
Claim 13
Dependent Claim
29 words
An implantable medical device in the form of a sheet consisting essentially of the random block copolymer of claim 1 for use as a barrier for surgical adhesion prevention.
Claim 14
Dependent Claim
46 words
A method for site-specific or systemic drug delivery comprising implanting in the body of a patient in need thereof an implantable drug delivery device comprising a therapeutically effective amount of a biologically or physiologically active compound in combination with the random block copolymer of claim 1.
Claim 15
Dependent Claim
18 words
The method of claim 13, wherein said biologically or physiologically active compound is covalently bonded to said copolymer.
Claim 16
Dependent Claim
32 words
A method for preventing the formation of adhesions between injured tissues comprising inserting as a barrier between said injured tissues a sheet consisting essentially of the random block copolymer of claim 1.
Claim 17
Dependent Claim
194 words
A polyarylate, polymerized as a random block copolymer of a dicarboxylic acid with both a tyrosine-derived diphenol and a poly(alkylene oxide), wherein an equimolar combined quantity of said diphenol and said poly(alkylene oxide) is reacted with said dicarboxylic acid in a molar ratio of said diphenol to said poly(alkylene oxide) between about 1:99 and about 99:1; and wherein said dicarboxylic acid has the structure: ##STR6## in which R is selected from the group consisting of saturated and unsaturated, substituted and unsubstituted alkyl, aryl and alkylaryl groups containing up to 18 carbon atoms; said tyrosine-derived diphenol has the structure: ##STR7## in which R 1 is --CH═CH-- or (--CH 2 --) j , wherein j is zero or an integer from one to eight, and R 2 is selected from the group consisting of straight and branched alkyl and alkylaryl groups containing up to 18 carbon atoms and derivatives of biologically and pharmaceutically active compounds covalently bonded to said diphenol; and said poly(alkylene oxide) has the structure: (--O--R.sub.3 --).sub.y in which each R 3 is independently an alkylene group containing up to 4 carbon atoms and y is an integer between about 5 and about 3000.
Claim 18
Dependent Claim
194 words
A polyarylate, polymerized as a random block copolymer of a dicarboxylic acid with both a tyrosine-derived diphenol and a poly(alkylene oxide), wherein an equimolar combined quantity of said diphenol and said poly(alkylene oxide) is reacted with said dicarboxylic acid in a molar ratio of said diphenol to said poly(alkylene oxide) between about 1:99 and about 99:1; and wherein said dicarboxylic acid has the structure: ##STR6## in which R is selected from the group consisting of saturated and unsaturated, substituted and unsubstituted alkyl, aryl and alkylaryl groups containing up to 18 carbon atoms; said tyrosine-derived diphenol has the structure: ##STR7## in which R 1 is --CH═CH-- or (--CH 2 --) j , wherein j is zero or an integer from one to eight, and R 2 is selected from the group consisting of straight and branched alkyl and alkylaryl groups containing up to 18 carbon atoms and derivatives of biologically and pharmaceutically active compounds covalently bonded to said diphenol; and said poly(alkylene oxide) has the structure: (--O--R.sub.3 --).sub.y in which each R 3 is independently an alkylene group containing up to 4 carbon atoms and y is an integer between about 5 and about 3000.
References Cited (Backward Citations)
US4308145A
Cited
US4069151A
Cited
US4436839A
Cited
US4686044A
Cited
EP0046817A1
Cited
US5084173A
Cited
US5099060A
Cited
US5198507A
Cited
US5216115A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2000-08-18 | 2001-02-17 | 2001-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-08-18 | 2005-02-17 | 2005-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-08-18 | 2009-02-17 | 2009-08-19 | $7700.00 | Window Closed / Lapsed |