US4755379A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polymers substituted by groups conferring anti-coagulant properties on them, process for their preparation, articles and compositions made therefrom and uses thereof
Assignee: Individual
•
Filing: 1985-09-27
•
Granted: 1988-07-05
•
Expires: 2005-09-27
Abstract
Abstract Anticoagulant products are constituted by polymers (homopolymers or copolymers) including in their chain substitutable groups on which are fixed statistically, groups X and/or Y and/or V, where X denotes the group --SO 3 R 1 or --R 3 --SO 3 R 1 , R 1 being a hydrogen atom or a physiologically compatible metal, R 3 being a --CH 2 --CO--NH--R 4 group in which R 4 represensts an alkyl aryl or alkylaryl radical, which may or may not be substituted, or substituted or unsubstituted --CH 2 --; Y denotes the group --SO 2 --R 2 or --R 3 --SO 2 --R 2 , R 2 being the residue of an amino acid connected to the --SO 2 bridge through its amine function and V denotes the group --CH 2 --CO--NH--CHR--COOH, R being the side chain of an amino acid it being understood that: (a) if X is --SO 3 R 1 it is necessarily accompanied by Y and/or by V, and (b) V is always accompanied by X and/by Y.
Inventors
- 👤 Marcel Jozefonvicz
- 👤 Jacqueline Jozefonvicz
- 👤 Christine Fougnot
- 👤 Monique Mauzac
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 15:37
CPC Classifications
C; C08; C08J; C08J7/00; C08J7/12; C08J7/14; A; A61; A61K; A61K31/00; A61K31/74; A61K31/795; A61L; A61L33/00; A61L33/0005; A61L33/0011; A61L33/0041; A61L33/06; A61L33/064; A61L33/08; C08F; C08F8/00; C08F8/30
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
198 words
A substituted synthetic water soluble or water insoluble polymer that has blood anticoagulating properties of natural heparin, said polymer comprising a polymer selected from the group consisting of polystyrene, dextran, and styrene-divinylbenzene copolymer on which there is fixed groups X, V and Y, wherein: X is H, --SO 3 R 1 or --R 3 SO 3 R 1 , Y is H, --SO 2 R 2 or --R 3 SO 2 --R 2 V is H, or --CH 2 --CO--NH--CHR--COOH, with the provision that at least one of X, Y and V is other than H, R is the side chain of an amino acid, R 1 is a hydrogen atom or a pharmaceutically acceptable metal salt, R 2 is a single amino acid connected to the --SO 2 bridge through its amine function, R 3 is --CH 2 --CO--NH--R 4 , R 4 is alkyl, phenyl or, benzyl and further when X is --SO 3 R 1 , then at least one of Y or V is other than H and where V is --CH 2 --CO--NH--CHR--COOH, at least one of X or Y is other than H; and X, Y, and V are as defined above.
Claim 2
Dependent Claim
198 words
A substituted synthetic water soluble or water insoluble polymer that has blood anticoagulating properties of natural heparin, said polymer comprising a polymer selected from the group consisting of polystyrene, dextran, and styrene-divinylbenzene copolymer on which there is fixed groups X, V and Y, wherein: X is H, --SO 3 R 1 or --R 3 SO 3 R 1 , Y is H, --SO 2 R 2 or --R 3 SO 2 --R 2 V is H, or --CH 2 --CO--NH--CHR--COOH, with the provision that at least one of X, Y and V is other than H, R is the side chain of an amino acid, R 1 is a hydrogen atom or a pharmaceutically acceptable metal salt, R 2 is a single amino acid connected to the --SO 2 bridge through its amine function, R 3 is --CH 2 --CO--NH--R 4 , R 4 is alkyl, phenyl or, benzyl and further when X is --SO 3 R 1 , then at least one of Y or V is other than H and where V is --CH 2 --CO--NH--CHR--COOH, at least one of X or Y is other than H; and X, Y, and V are as defined above.
Claim 3
Dependent Claim
9 words
The polymers of claim 1 which is a copolymer.
Claim 4
Dependent Claim
33 words
The polymer of claim 1 wherein when X is --SO 3 R 1 or --R 3 SO 3 R 1 , then at least one of Y or V is other than H.
Claim 5
Dependent Claim
22 words
The polymer of claim 1 wherein when X is --R 3 SO 3 R 1 , then Y and V are H.
Claim 6
Dependent Claim
16 words
The polymer of claim 1 wherein the amino acids have at least one free carboxylic function.
Claim 7
Dependent Claim
13 words
The polymer of claim 5 wherein the amino acid is a dicarboxylic acid.
Claim 8
Dependent Claim
44 words
The polymer of claim 1 wherein the amino acids are selected from the group which consists of: glutamic acid, aspartic acid, methionine, cysteine, cysteic acid, proline, hydroxyproline, threonine, serine, tyrosine, alanine, phenylalanine, valine, leucine, benzyloxycarbonyl-lysine, tertiobutyloxycarbonyl-lysine, 6-aminocaproic acid, beta-alanine 4-amino-n-butyric acid and 5-amino-n-valeric acid.
Claim 9
Dependent Claim
12 words
The polymer of claim 1 wherein the amino acid is not substituted.
Claim 10
Dependent Claim
26 words
The polymer of claim 1 wherein the amino acid has more than one amino function, all except one being blocked by a physiologically acceptable blocking group.
Claim 11
Dependent Claim
22 words
The polymer of claim 9 wherein the blocking group is selected from the group consisting of a benzyloxy-carbonyl or a tertiobutyloxycarbonyl group.
Claim 12
Dependent Claim
11 words
The polymer of claim 1 wherein the backbone polymer is polystyrene.
Claim 13
Dependent Claim
30 words
The polymer of claim 1 wherein the functional groups on the backbone comprises about 1.37 meq per gram of hydroxyproline and about 2.16 meq of sulfonate per gram of polymer.
Claim 14
Dependent Claim
33 words
The polymer of claim 1 wherein the polymer is polystyrene which is not cross-linked and X is --SO 3 R 1 , Y is --SO 2 R 2 , and V is H.
Claim 15
Dependent Claim
7 words
The polymer of claim 1 wherein ##STR12##
Claim 16
Dependent Claim
29 words
A pharmaceutical composition having anticoagulant properties comprising a biologically acceptable carrier and a biologically effective amount of a polymer soluble in water or biological fluids defined in claim 1.
Claim 17
Dependent Claim
13 words
The pharmaceutical composition according to claim 15 wherein the polymer is a polystrene.
Claim 18
Dependent Claim
194 words
A substituted synthetic water soluble polysaccharide that has the blood anticoagulant properties of natural heparin, which polysaccharide comprises a dextran on which there is fixed the groups X, V and Y, wherein: X is H, --SO 3 R 1 or --R 3 SO 3 R 1 , Y is H, --SO 2 R 2 or --R 3 SO 2 --R 2 V is H, or --CH 2 --CO--NH--CHR--COOH, with the provision that at least one of X, Y and V is other than H, R is the side chain of an amino acid having at least one free carboxylic acid group, R 1 is a hydrogen atom or a pharmaceutically acceptable metal salt, R 2 is a single amino acid connected to the --SO 2 bridge through its amine function, R 3 is --CH 2 --CO--NH--R 4 , R 4 is alkyl, phenyl or benzyl, and further when X is --SO 3 R 1 , then at least one of Y or V is other than H and where V is --CH 2 --CO--NH--CHR--COOH, at least one of X or Y is other than H; and X, Y, and V are as defined above.
Claim 19
Dependent Claim
194 words
A substituted synthetic water soluble polysaccharide that has the blood anticoagulant properties of natural heparin, which polysaccharide comprises a dextran on which there is fixed the groups X, V and Y, wherein: X is H, --SO 3 R 1 or --R 3 SO 3 R 1 , Y is H, --SO 2 R 2 or --R 3 SO 2 --R 2 V is H, or --CH 2 --CO--NH--CHR--COOH, with the provision that at least one of X, Y and V is other than H, R is the side chain of an amino acid having at least one free carboxylic acid group, R 1 is a hydrogen atom or a pharmaceutically acceptable metal salt, R 2 is a single amino acid connected to the --SO 2 bridge through its amine function, R 3 is --CH 2 --CO--NH--R 4 , R 4 is alkyl, phenyl or benzyl, and further when X is --SO 3 R 1 , then at least one of Y or V is other than H and where V is --CH 2 --CO--NH--CHR--COOH, at least one of X or Y is other than H; and X, Y, and V are as defined above.
Claim 20
Dependent Claim
12 words
The polysaccharide of claim 17 wherein the amino acid is glutamic acid.
Claim 21
Dependent Claim
24 words
The polysaccharide of claim 17 wherein X is R 3 SO 3 R 1 , V is --CH 2 --CO--NH--CHR--COOH, and Y is H.
Claim 22
Dependent Claim
7 words
The polysaccharide of claim 19 wherein ##STR13##
Claim 23
Dependent Claim
20 words
The polysaccharide of claim 17 wherein X is --SO 3 R 1 , V is CH--CO--NH--CHR--COOH, and Y is H.
Claim 24
Dependent Claim
7 words
The polymer of claim 21 wherein ##STR14##
Claim 25
Dependent Claim
29 words
A pharmaceutical composition having anticoagulating properties comprising a biologically acceptable carrier and a biologically effective amount of a polymer soluble in water or biological fluids defined in claim 17.
Claim 26
Dependent Claim
76 words
A substitute synthetic water-insoluble polystyrene having the blood anticoagulant properties of natural heparin, which comprises a polystyrene on which there is fixed the groups X and Y, wherein: X is --SO 3 R 1 , and Y is --SO 2 R 2 , wherein: R 1 is a hydrogen atom or a pharmaceutically acceptable metal salt, and R 2 is a single amino acid which is connected to the --SO 2 bridge through its amine function.
Claim 27
Dependent Claim
76 words
A substitute synthetic water-insoluble polystyrene having the blood anticoagulant properties of natural heparin, which comprises a polystyrene on which there is fixed the groups X and Y, wherein: X is --SO 3 R 1 , and Y is --SO 2 R 2 , wherein: R 1 is a hydrogen atom or a pharmaceutically acceptable metal salt, and R 2 is a single amino acid which is connected to the --SO 2 bridge through its amine function.
Claim 28
Dependent Claim
12 words
The polystyrene of claim 24 wherein the amino acid is glutamic acid.
Claim 29
Dependent Claim
73 words
A substituted water-insoluble polystyrene having the blood anticoagulant properties of natural heparin, which comprises a polystyrene on which there is fixed the groups X and Y, wherein X is --SO 3 R 1 , and Y is --SO 2 R 2 , wherein: R 1 is a hydrogen atom or a pharmaceutically acceptable metal salt, and R 2 is a hydroxyproline which is connected to the --SO 2 bridge through its amine function.
Claim 30
Dependent Claim
73 words
A substituted water-insoluble polystyrene having the blood anticoagulant properties of natural heparin, which comprises a polystyrene on which there is fixed the groups X and Y, wherein X is --SO 3 R 1 , and Y is --SO 2 R 2 , wherein: R 1 is a hydrogen atom or a pharmaceutically acceptable metal salt, and R 2 is a hydroxyproline which is connected to the --SO 2 bridge through its amine function.
Claim 31
Dependent Claim
182 words
A substituted synthetic water-insoluble polysaccharide that has the blood anticoagulant properties of natural heparin, which polysaccharide comprises a dextran on which there is fixed the groups X, V and Y, wherein: X is H, --SO 3 R 1 or --R 3 SO 3 R 1 , Y is H, --SO 2 R 2 or --R 3 SO 2 --R 2 V is H, or --CH 2 --CO--NH--CHR--COOH, with the provision that at least one of X, Y and V is other than H, R is the side chain of an amino acid, R 1 is a hydrogen atom or pharmaceutically acceptable metal salt, R 2 is a single amino acid connected to the --SO 2 bridge through its amine function, R 3 is --CH 2 --CO--NH--R 4 , R 4 is alkyl, phenyl or benzyl, and further when X is --SO 3 R 1 , then at least one of Y or V is other than H, and where V is present, at least one of X or Y is other than H; and X, Y, and V are as defined above.
Claim 32
Dependent Claim
182 words
A substituted synthetic water-insoluble polysaccharide that has the blood anticoagulant properties of natural heparin, which polysaccharide comprises a dextran on which there is fixed the groups X, V and Y, wherein: X is H, --SO 3 R 1 or --R 3 SO 3 R 1 , Y is H, --SO 2 R 2 or --R 3 SO 2 --R 2 V is H, or --CH 2 --CO--NH--CHR--COOH, with the provision that at least one of X, Y and V is other than H, R is the side chain of an amino acid, R 1 is a hydrogen atom or pharmaceutically acceptable metal salt, R 2 is a single amino acid connected to the --SO 2 bridge through its amine function, R 3 is --CH 2 --CO--NH--R 4 , R 4 is alkyl, phenyl or benzyl, and further when X is --SO 3 R 1 , then at least one of Y or V is other than H, and where V is present, at least one of X or Y is other than H; and X, Y, and V are as defined above.
Claim 33
Dependent Claim
10 words
The polysaccharide of claim 27 wherein the polyglucoside is crosslinked.
Claim 34
Dependent Claim
30 words
The polymer of claim 27 wherein the polymer is a dextran and X is --R 3 SO 3 R 1 , V is --CH 2 --CO--NH--CHR--COOH, and Y is H.
Claim 35
Dependent Claim
22 words
The polymer of claim 27 wherein X is --SO 3 R 1 , V is --CH 2 --CO--NH--CHR--COOH, and Y is H.
References Cited (Backward Citations)
US3211617A
Cited
US3475358A
Cited
FR2066460A5
Cited
FR2078435A5
Cited
US3766104A
Cited
US3697498A
Cited
US3862309A
Cited
US3907755A
Cited
US3998796A
Cited
US3987163A
Cited
US3893890A
Cited
US3961045A
Cited
US4119616A
Cited
US4095000A
Cited
US4271151A
Cited
US4116898A
Cited
DE2728718A1
Cited
US4303786A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-07-05 | 1992-01-04 | 1992-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-07-05 | 1996-01-04 | 1996-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-07-05 | 2000-01-04 | 2000-07-05 | $7700.00 | Window Closed / Lapsed |