US4916209A
Expired / Lapsed
US
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Bioabsorbable polydepsipeptide, preparation and use thereof
Assignee: Pfizer Inc
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Filing: 1987-12-23
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Granted: 1990-04-10
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Expires: 2007-12-23
Abstract
Abstract Novel, semi-crystalline depsipeptide polymers and copolymers particularly suitable for use in fabricating bioabsorbable medical implant devices such as sutures or clips and obtained through ring-opening polymerization of certain 3-substituted-2,5-morpholinediones prepared by reacting a naturally occurring alpha-amino acid with an alpha-halo acid chloride in inert solvent in the presence of an acid acceptor.
Inventors
- 👤 Fu-Ning Fung
- 👤 Raymond C. Glowaky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 12:11
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/28; C07D265/30; C07D265/32; A; A61; A61L; A61L17/00; A61L17/06; A61L17/10; A61L17/12; A61L27/00; A61L27/14; A61L27/18; A61L31/00; A61L31/04; A61L31/043; A61L31/047; A61L31/06; A61L31/14; A61L31/148
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
146 words
An optically-active, hydrolyzable, semi-crystalline polydepsipeptide having a number average molecular weight of from about 5,000 to 200,000 and the structural formula V: ##STR23## wherein R is C 1 -C 12 alkyl, C 1-C 6 alkoxy (C 1 -C 6 alkyl), aryl, aryl(C 1 -C 12 alkyl), C 1 -C 12 alkylaryl, C 1 -C 6 alkylaryl(C 1 -C 6 alkyl), C 1 -C 6 alkylthio(C 1 -C 6 alkyl), C 1 -C 6 alkylsulfinyl(C 1 -C 6 alkyl), C 1 -C 6 alkylsulfonyl(C 1 -C 6 alkyl), cyano(C 1 -C 12 alkyl) or aminocarbonyl(C 1 -C 12 alkyl), with each aryl group having up to 10 carbons in the nuclear ring, p1 x,y are relative amounts of (D) and (L) optical isomers, respectively, wherein the asterisk indicates the stated optical activity, and the ratio x/(x+y) is either less than about 0.45 or greater than about 0.55.
Claim 2
Dependent Claim
146 words
An optically-active, hydrolyzable, semi-crystalline polydepsipeptide having a number average molecular weight of from about 5,000 to 200,000 and the structural formula V: ##STR23## wherein R is C 1 -C 12 alkyl, C 1-C 6 alkoxy (C 1 -C 6 alkyl), aryl, aryl(C 1 -C 12 alkyl), C 1 -C 12 alkylaryl, C 1 -C 6 alkylaryl(C 1 -C 6 alkyl), C 1 -C 6 alkylthio(C 1 -C 6 alkyl), C 1 -C 6 alkylsulfinyl(C 1 -C 6 alkyl), C 1 -C 6 alkylsulfonyl(C 1 -C 6 alkyl), cyano(C 1 -C 12 alkyl) or aminocarbonyl(C 1 -C 12 alkyl), with each aryl group having up to 10 carbons in the nuclear ring, p1 x,y are relative amounts of (D) and (L) optical isomers, respectively, wherein the asterisk indicates the stated optical activity, and the ratio x/(x+y) is either less than about 0.45 or greater than about 0.55.
Claim 3
Dependent Claim
18 words
The polydepsipeptide of claim 1 wherein R is alkyl of from 1 to 4 carbons, benzyl or 2-methylthioethyl.
Claim 4
Dependent Claim
33 words
The polydepsipeptide of claim 2 wherein the molecular weight is from about 10,000 to 50,000, R is CH 3 and x/(x+y) is from about 0.2 to 0.4 or from about 0.6 to 0.8.
Claim 5
Dependent Claim
11 words
A bioabsorbable surgical device fabricated from the polydepsipeptide of claim 1.
Claim 6
Dependent Claim
14 words
The surgical device of claim 4 in the form of a suture or clip.
Claim 7
Dependent Claim
43 words
A process for the preparation of an optically-active, hydrolyzable, semi-crystalline polydepsipeptide according to claim 1, which comprises polymerizing an optically active 3-substituted-2,5-morpholinedione having the structural formula I ##STR24## wherein R is as defined in claim 4, in the presence of an organometallic catalyst.
Claim 8
Dependent Claim
21 words
The process of claim 6 wherein the polymerization is conducted neat at a temperature of from about 100° to 250° C.
Claim 9
Dependent Claim
13 words
A process according to claim 6, wherein the organometallic catalyst is stannous octoate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-04-09 | 1993-10-09 | 1994-04-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-04-09 | 1997-10-09 | 1998-04-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-04-09 | 2001-10-09 | 2002-04-10 | $7700.00 | Window Closed / Lapsed |