Patent US5248761A successfully refreshed from Google Patents.
US5248761A
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US
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Amino acid terminated polyesters having predetermined monomeric sequence
Assignee: United States Surgical Corp
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Filing: 1992-08-12
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Granted: 1993-09-28
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Expires: 2012-08-12
Abstract
Abstract Compositions comprising amino acid terminated polyesters having predetermined monomeric sequence are produced by stepwise addition of monomeric hydroxyacids to an amine to form a growing polymeric chain. Included herein are various amino acid terminated polyesters having predetermined monomeric sequence, methods for their production and use as well as articles formed from said compositions.
Inventors
- 👤 Matthew E. Hermes
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:53
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/44; A; A61; A61K; A61K9/00; A61K9/20; A61K9/2004; A61K9/2022; A61K9/2031; A61K9/204; A61L; A61L17/00; A61L17/06; A61L17/10; A61L17/12; A61L27/00; A61L27/14; A61L27/18; A61L31/00; A61L31/04; A61L31/06; C08G63/00; C08G63/68; C08G63/685; C08G63/6852
Claims Analysis
Total Claims: 53
Claim 1
Independent Claim
30 words
An composition comprising an amino acid terminated polyester having a predetermined monomeric sequence comprising at least one amine and at least three monomeric units derived from at least one hydroxyacid.
Claim 2
Dependent Claim
30 words
An composition comprising an amino acid terminated polyester having a predetermined monomeric sequence comprising at least one amine and at least three monomeric units derived from at least one hydroxyacid.
Claim 3
Dependent Claim
39 words
A composition according to claim 1 where said hydroxyacid monomeric units are the same or different and are selected from the group consisting of glycolic acid, lactic acid, hydroxybutyric acid, hydroxyvaleric acid, tartronic acid, malic acid and citric acid.
Claim 4
Dependent Claim
21 words
A composition according to claim 1 wherein said amino acid is selected from the group consisting of glycyl, alanyl and valyl.
Claim 5
Dependent Claim
21 words
A composition according to claim 1 wherein at least one hydroxy polycarboxylic acid is incorporated into said amino acid terminated polyester.
Claim 6
Dependent Claim
16 words
A composition according to claim 4 wherein said amino acid terminated polyester is a dendritic polymer.
Claim 7
Dependent Claim
24 words
A composition comprising a polymer having incorporated therein as a segment of said polymer an amino acid terminated polyester having a predetermined monomeric sequence.
Claim 8
Dependent Claim
24 words
A composition comprising a polymer having incorporated therein as a segment of said polymer an amino acid terminated polyester having a predetermined monomeric sequence.
Claim 9
Dependent Claim
17 words
A composition according to claim 6 wherein said amino acid terminated polyester is copolymerized with a polyester.
Claim 10
Dependent Claim
19 words
A composition according to claim 6 wherein said composition is a block copolymer comprising said amino acid terminated polyester.
Claim 11
Dependent Claim
21 words
A composition according to claim 8 wherein at least one block of said block copolymer comprises said amino acid terminated polyester.
Claim 12
Dependent Claim
29 words
A process for making an amino acid terminated polyester having predetermined monomeric sequence comprising stepwise addition of at least three monomeric hydroxyacid units to an amino acid monomeric unit.
Claim 13
Dependent Claim
29 words
A process for making an amino acid terminated polyester having predetermined monomeric sequence comprising stepwise addition of at least three monomeric hydroxyacid units to an amino acid monomeric unit.
Claim 14
Dependent Claim
90 words
A process for making a polymer comprising: (a) providing an amino acid having an active site thereof protected; (b) forming a polymer chain by the stepwise addition of at least three hydroxyacid units, the step of adding hydroxyacid units comprising: i) forming a reaction product including the protected amino acid, the reaction product having a terminal hydroxyacid, said terminal hydroxyacid having an active site thereof protected by a protecting substituent; ii) removing the protecting substituent from a terminal hydroxyacid of the reaction product; and iii) repeating steps (i) and (ii).
Claim 15
Dependent Claim
90 words
A process for making a polymer comprising: (a) providing an amino acid having an active site thereof protected; (b) forming a polymer chain by the stepwise addition of at least three hydroxyacid units, the step of adding hydroxyacid units comprising: i) forming a reaction product including the protected amino acid, the reaction product having a terminal hydroxyacid, said terminal hydroxyacid having an active site thereof protected by a protecting substituent; ii) removing the protecting substituent from a terminal hydroxyacid of the reaction product; and iii) repeating steps (i) and (ii).
Claim 16
Dependent Claim
91 words
A process for making a polymer comprising: (a) providing an amino acid having the amino group thereof protected; (b) forming a polymer chain by the stepwise addition of at least three hydroxyacid monomeric units, the step of adding of hydroxyacid units comprising: i) forming a reaction product including the protected amino acid, the reaction product having a terminal hydroxyacid, said terminal hydroxyacid having its carboxyl group protected by a carboxyl-protecting substituent; ii) removing the carboxyl-protecting substituent from a terminal hydroxyacid of the reaction product; and iii) repeating steps (i) and (ii).
Claim 17
Dependent Claim
91 words
A process for making a polymer comprising: (a) providing an amino acid having the amino group thereof protected; (b) forming a polymer chain by the stepwise addition of at least three hydroxyacid monomeric units, the step of adding of hydroxyacid units comprising: i) forming a reaction product including the protected amino acid, the reaction product having a terminal hydroxyacid, said terminal hydroxyacid having its carboxyl group protected by a carboxyl-protecting substituent; ii) removing the carboxyl-protecting substituent from a terminal hydroxyacid of the reaction product; and iii) repeating steps (i) and (ii).
Claim 18
Dependent Claim
47 words
A process according to claim 12 wherein said step of forming a reaction product comprises reacting (i) an amino acid having an amino group protected with (ii) a first hydroxyacid having a carboxyl group protected by a carboxyl-protecting substituent whereby said first hydroxyacid becomes a terminal hydroxyacid.
Claim 19
Dependent Claim
32 words
A process according to claim 12 wherein said terminal hydroxyacid is selected from the group consisting of glycolic acid, lactic acid, hydroxybutyric acid, hydroxyvaleric acid, tartronic acid, malic acid and citric acid.
Claim 20
Dependent Claim
15 words
A process according to claim 12 wherein said terminal hydroxyacid is a hydroxy polycarboxylic acid.
Claim 21
Dependent Claim
21 words
A process according to claim 12 wherein said amino acid is selected from the group consisting of glycine, alanine and valine.
Claim 22
Dependent Claim
40 words
A process according to claim 12 wherein a carboxyl group on the terminal hydroxyacid of the reaction product and said carboxyl-protecting substituent form a member selected from the group consisting of methyl esters, ethyl esters, t-butyl esters and benzyl esters.
Claim 23
Dependent Claim
93 words
A process for making a polymer comprising: a) providing an amino acid having the carboxyl group thereof bonded to a resin support; b) forming a polymer chain by the stepwise addition of hydroxyacid monomeric units, the step of adding hydroxyacid units comprising; (i) forming a reaction product including the amino acid, said reaction product having a terminal hydroxy acid, said terminal hydroxyacid having its hydroxyl group protected by a hyroxyl-protecting substituent; the hydroxyl-protecting (ii) removing the hydroxyl-protecting substituent from a terminal hydroxyacid of the reaction product; and (iii) repeating steps (i) and (ii).
Claim 24
Dependent Claim
93 words
A process for making a polymer comprising: a) providing an amino acid having the carboxyl group thereof bonded to a resin support; b) forming a polymer chain by the stepwise addition of hydroxyacid monomeric units, the step of adding hydroxyacid units comprising; (i) forming a reaction product including the amino acid, said reaction product having a terminal hydroxy acid, said terminal hydroxyacid having its hydroxyl group protected by a hyroxyl-protecting substituent; the hydroxyl-protecting (ii) removing the hydroxyl-protecting substituent from a terminal hydroxyacid of the reaction product; and (iii) repeating steps (i) and (ii).
Claim 25
Dependent Claim
35 words
A process according to claim 18 wherein said step of forming a reaction product comprises reacting the amino acid with a first hydroxyacid said first hydroxyacid having its hydroxyl group protected by a hydroxyl-protecting substituent.
Claim 26
Dependent Claim
50 words
A process according to claim 18 wherein said step of providing an amino acid having the carboxyl group thereof bonded to a resin support comprises: functionalizing an insoluble resin by reacting a functionalizer therewith; reacting a bifunctional spacer with said functionalizer; and reacting an amino acid with said bifunctional spacer.
Claim 27
Dependent Claim
21 words
A process according to claim 18 wherein said amino acid is selected from the group consisting of glycine, alanine and valine.
Claim 28
Dependent Claim
32 words
A process according to claim 18 wherein said terminal hydroxyacid is selected from the group consisting of glycolic acid, lactic acid, hydroxybutyric acid, hydroxyvaleric acid, tartronic acid, malic acid and citric acid.
Claim 29
Dependent Claim
15 words
A process according to claim 18 wherein said terminal hydroxyacid is a hydroxy polycarboxylic acid.
Claim 30
Dependent Claim
67 words
A process according to claim 20 wherein a hydroxyl group on the terminal hydroxyacid of the reaction product and said hydroxyl-protecting substituent form a member selected from the group consisting of methoxymethyl ethers, t-butoxymethyl ethers, methoxyethoxymethyl ethers, bis(2-chloroethoxy)methyl ethers, 2-(trimethylsilyl)-ethoxymethyl ethers, tetrahydropyranyl ethers, 4methoxytetrahydropyranyl ethers, tetrahydrofuranyl 1-ethoxyethylethers, 1-methyl-1-methoxyethyl ethers, 1-(isopropoxy)ethyl ethers, trimethylsilyl ethers, triethylsilyl ethers, t-butyl-dimethylsilyl ethers, formate esters, benzyl formate esters, chloroacetate esters, and dichloroacetate esters.
Claim 31
Dependent Claim
20 words
A process according to claim 18 further comprising the step of cleaving the amino acid terminated polyester from the support.
Claim 32
Dependent Claim
22 words
A process according to claim 18 wherein said steps (i), (ii) and (iii) are performed automatically by an automated liquid handling system.
Claim 33
Dependent Claim
83 words
A process for making a polymer comprising: a) providing an amino acid having the carboxyl group thereof protected; b) forming a polymer chain by the stepwise addition of hydroxyacid monomeric units, the step of adding hydroxyacid units comprising: (i) forming a reaction product including the protected amino acid, said product having a terminal hydroxyacid having its hydroxyl group protected by a hydroxyl-protecting substituent; (ii) removing the hydroxyl-protecting substituent from a terminal hydroxyacid of the reaction product; and (iii) repeating steps (i) and (ii).
Claim 34
Dependent Claim
83 words
A process for making a polymer comprising: a) providing an amino acid having the carboxyl group thereof protected; b) forming a polymer chain by the stepwise addition of hydroxyacid monomeric units, the step of adding hydroxyacid units comprising: (i) forming a reaction product including the protected amino acid, said product having a terminal hydroxyacid having its hydroxyl group protected by a hydroxyl-protecting substituent; (ii) removing the hydroxyl-protecting substituent from a terminal hydroxyacid of the reaction product; and (iii) repeating steps (i) and (ii).
Claim 35
Dependent Claim
40 words
A process according to claim 27 wherein said step of forming a reaction product comprises reacting said amino acid with a first hydroxyacid having a hydroxyl group protected by a hydroxyl-protecting substituent whereby said first hydroxyacid becomes a terminal hydroxyacid.
Claim 36
Dependent Claim
21 words
A process according to claim 27 wherein said amino acid is selected from the group consisting of glycine, alanine and valine.
Claim 37
Dependent Claim
43 words
A process for making an amino acid terminated polyesters having predetermined monomeric sequence according to claim 27 wherein said terminal hydroxyacid is selected from the group consisting of glycolic acid, lactic acid, hydroxybutyric acid, hydroxyvaleric acid, tartronic acid, malic acid and citric acid.
Claim 38
Dependent Claim
67 words
A process according to claim 27 wherein a hydroxyl group on the terminal hydroxyacid of the reaction product and said hydroxyl-protecting substituent form a member selected from the group consisting of methoxymethyl ethers, t-butoxymethyl ethers, methoxyethoxymethyl ethers, bis(2-chloroethoxy)methyl ethers, 2-(trimethylsilyl)ethoxymethyl ethers, tetrahydropyranyl ethers, 4-methoxytetrahydropyranyl ethers, tetrahydrofuranyl 1-ethoxyethylethers, 1-methyl-1-methoxyethyl ethers, 1-(isopropoxy)ethyl ethers, trimethylsilyl ethers, triethylsilyl ethers, t-butyl-dimethylsilyl ethers, formate esters, benzyl formate esters, chloroacetate esters, and dichloroacetate esters.
Claim 39
Dependent Claim
46 words
A process according to claim 27 wherein said step of providing an amino acid comprises reacting a carboxyl-protecting group with a carboxyl group on an amino acid to form a member selected from the group consisting of methyl esters, ethyl esters, t-butyl esters, and benzyl esters.
Claim 40
Dependent Claim
36 words
A process according to claim 27 wherein said step of forming a reaction product is conducted in the presence of a dehydrating agent selected from the group consisting of dicyclohexylcarbodiimide (DCDI), trifluoroacetic acid, and N,N'-carbonyldiimidazole (CDI).
Claim 41
Dependent Claim
72 words
A process for making a polymer comprising: a) providing an amino acid having an amino group thereof protected; b) forming a polymer chain by the stepwise addition of hydroxyacid monomeric units, the step of adding hydroxyacid units comprising: (i) forming a reaction product including the amino acid said reaction product having a terminal hydroxyacid; (ii) reacting the reaction product with dicyclohexylcarbodiimide to form an isolate; and (iii) repeating steps (i) and (ii).
Claim 42
Dependent Claim
72 words
A process for making a polymer comprising: a) providing an amino acid having an amino group thereof protected; b) forming a polymer chain by the stepwise addition of hydroxyacid monomeric units, the step of adding hydroxyacid units comprising: (i) forming a reaction product including the amino acid said reaction product having a terminal hydroxyacid; (ii) reacting the reaction product with dicyclohexylcarbodiimide to form an isolate; and (iii) repeating steps (i) and (ii).
Claim 43
Dependent Claim
41 words
A process as in claim 34 wherein said step of forming a reaction product comprises: reacting said amino acid with dicyclohexylcarbodiimide to form an isolate; and reacting said isolate with a first hydroxyacid whereby said first hydroxyacid becomes a terminal hydroxyacid.
Claim 44
Dependent Claim
21 words
A process according to claim 34 wherein said amino acid is selected from the group consisting of glycine, alanine and valine.
Claim 45
Dependent Claim
32 words
A process according to claim 34 wherein said terminal hydroxyacid is selected from the group consisting of glycolic acid, lactic acid, hydroxybutyric acid, hydroxyvaleric acid, tartronic acid, malic acid and citric acid.
Claim 46
Dependent Claim
16 words
An amino acid terminated polyester having predetermined monomeric sequence manufactured by a process of claim 10.
Claim 47
Dependent Claim
16 words
An amino acid terminated polyester having predetermined monomeric sequence manufactured by a process of claim 12.
Claim 48
Dependent Claim
16 words
An amino acid terminated polyester having predetermined monomeric sequence manufactured by a process of claim 18.
Claim 49
Dependent Claim
16 words
An amino acid terminated polyester having predetermined monomeric sequence manufactured by a process of claim 27.
Claim 50
Dependent Claim
16 words
An amino acid terminated polyester having predetermined monomeric sequence manufactured by a process of claim 34.
Claim 51
Dependent Claim
19 words
A medical device made in whole or in part of an amino acid terminated polyester having predetermined monomeric sequence.
Claim 52
Dependent Claim
19 words
A medical device made in whole or in part of an amino acid terminated polyester having predetermined monomeric sequence.
Claim 53
Dependent Claim
36 words
A medical device according to claim 43 wherein said medical device is selected from the group consisting of sutures, prosthetic ligaments, prosthetic tendons, staples, clips, pins, screws, mesh, felt, growth supporting matrices and drug delivery devices.
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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) | 1996-09-27 | 1997-03-29 | 1997-09-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-09-27 | 2001-03-29 | 2001-09-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-09-27 | 2005-03-29 | 2005-09-28 | $7700.00 | Window Closed / Lapsed |