US4957744A
Expired / Lapsed
US
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Cross-linked esters of hyaluronic acid
Assignee: Fidia SpA
•
Filing: 1987-10-13
•
Granted: 1990-09-18
•
Expires: 2007-10-13
Abstract
Abstract Cross-linked esters of hyaluronic acid are provided which result from the esterification of polyhydric alcohols with two or more carboxy groups of the hyaluronic acid polysaccharide. These cross-linked esters are useful in the field of biodegradable plastics for sanitary and surgical articles and in the pharmaceutical and cosmetic fields for the preparation of useful compositions and articles.
Inventors
- 👤 Francesco Della Valle
- 👤 Aurelio Romeo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 15:13
CPC Classifications
C; C08; C08B; C08B37/00; C08B37/0006; C08B37/0024; C08B37/0027; C08B37/003; A; A61; A61K; A61K31/00; A61K31/70; A61K31/715; A61K47/00; A61K47/30; A61K47/36; A61K8/00; A61K8/18; A61K8/72; A61K8/73; A61K8/735; A61L; A61L15/00; A61L15/16; A61L15/22; A61L15/28; A61L17/00; A61L17/06; A61L17/10; A61L27/00; A61L27/14; A61L27/20; A61Q; A61Q19/00; C08B37/006; C08B37/0063; C08B37/0072
Claims Analysis
Total Claims: 92
Claim 1
Independent Claim
46 words
Total or partial cross-linked esters of hyaluronic acid with an aliphatic polyhydric alcohol, and salts of such partial esters with inorganic or organic bases, with the proviso that said cross-linked ester is not the cross-linked ester of hyaluronic acid with an alomethyloxirane or a bisepoxy compound
Claim 2
Dependent Claim
46 words
Total or partial cross-linked esters of hyaluronic acid with an aliphatic polyhydric alcohol, and salts of such partial esters with inorganic or organic bases, with the proviso that said cross-linked ester is not the cross-linked ester of hyaluronic acid with an alomethyloxirane or a bisepoxy compound
Claim 3
Dependent Claim
15 words
Cross-linked esters according to claim 1, wherein said aliphatic polyhydric alcohol is a dihydric alcohol.
Claim 4
Dependent Claim
18 words
Cross-linked esters according to claim 1, wherein said aliphatic polyhydric alcohol has between 2 and 16 carbon atoms.
Claim 5
Dependent Claim
37 words
Cross-linked esters according to claim 2, wherein said dihydric alcohol is a member selected from the group consisting of ethylene glycol, propylene glycol, butylene glycol, glycols derived from pentane, hexane, heptane and octane, and positional isomers thereof.
Claim 6
Dependent Claim
24 words
Cross-linked esters according to claim 1, wherein said aliphatic polyhydric alcohol is a member selected from the group consisting of glycerine, erythrite and pentaer/thrite.
Claim 7
Dependent Claim
122 words
Cross-linked esters according to claim 1, wherein at least one non-cross-linked carboxy group in said hyaluronic acid is esterified with an aliphatic alcohol having a maximum of 34 carbon atoms and wherein said aliphatic alcohol may be unsubstituted or substituted by one or two functional groups selected from the group consisting of amino, hydroxy, mercapto, aldehyde, keto, carboxy, hydrocarbyl and dihydrocarbylamino groups, ether, ester, thioether, thioester, acetal, ketal, carbalkoxy, carbamidic and substituted carbamidic groups substituted by one or two alkyl groups, the hydrocarbyl radicals in these functionally modified groups having a maximum of 6 carbon atoms, and in which such aliphatic alcohols may be interrupted in the carbon atom chain by heteroatoms selected from the group consisting of oxygen, sulphur and nitrogen.
Claim 8
Dependent Claim
25 words
Cross-linked esters according to claim 6, wherein said aliphatic alcohol is ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl alcohols, an amyl, pentyl, hexyl or octyl alcohol.
Claim 9
Dependent Claim
95 words
Cross-linked esters according to claim 1, wherein at least one non-cross-linked carboxy group in said hyaluronic acid is esterified with an araliphatic alcohol having only be benzene residue and in which the aliphatic chain has a maximum of 4 carbon atoms and in which the benzene residue may be substituted with between 1 and 3 methyl or hydroxy groups or with halogen atoms, and in which the aliphatic chain may be substituted with one or two functional groups selected from the group consisting of free- or mono- or diethyl amino groups, pyrrolidine and piperidine groups.
Claim 10
Dependent Claim
134 words
Cross-linked esters according to claim 1, wherein at least one non-cross-linked carboxy group in said hyaluronic acid is esterified with a cycloaliphatic alcohol or aliphatic-cycloaliphatic alcohol or heterocyclic alcohol which derives from a mono- or polycyclic carbohydrate with a maximum of 34 carbon atoms and is unsubstituted or substituted by one or more functional groups selected from the group consisting of amino, hydroxy, mercapto, aldehyde, keto, carboxy, hydrocarbyl- and dihydrocarbylamino groups, ether, ester, thioether, thioester, acetal, ketal, carbalkoxy, carbamidic and substituted carbamidic groups, by one or two alkyl groups, the hydrocarbyl radicals in these functionally modified groups having a maximum of 6 carbon atoms, and may be int errupted in the carbon atom chain by heteroatoms chosen from the group formed by oxygen, nitrogen and sulfur, and may have one or more aromatic bonds.
Claim 11
Dependent Claim
45 words
Cross-linked esters according to claim 9, wherein at least one of said non-cross-linked carboxy groups is esterified with an alcohol selected from the group consisting of cortisone, hydrocortisone, prednisone, prednisolone, fluorocortisone, dexamethasone, betamethasone, corticosterone, deoxysicorticosterone, paramethasone, flumethasone, flucinolone and its acetonide, fluprednylidene, clobetasol and beclomethasone.
Claim 12
Dependent Claim
28 words
Salts of partial esters according to claim 1, wherein said salt is a salt of said cross-linked ester with an alkaline or alkaline earth metal, magnesium or aluminum.
Claim 13
Dependent Claim
13 words
A sodium or ammonium salt of a cross-linked ester according to claim 11.
Claim 14
Dependent Claim
30 words
Salts of partial esters according to claim 1, wherein said salt is a salt of said partial cross-linked ester with ammonium, or with an aliphatic, araliphatic, cycloaliphatic or heterocyclic amine.
Claim 15
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 1 together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 16
Dependent Claim
25 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 1 as a vehicle, in admixture with a pharmacologically active agent.
Claim 17
Dependent Claim
29 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 8, wherein said alcohol esterified with said non-cross-linked carboxy group is a pharmacologically active alcohol.
Claim 18
Dependent Claim
23 words
A cosmetic article comprising as an active ingredient an effective amount of a cross-linked ester or a salt thereof according to claim 1.
Claim 19
Dependent Claim
19 words
A cosmetic article comprising as a cosmetic vehicle a cross-linked ester or a salt thereof according to claim 1.
Claim 20
Dependent Claim
18 words
A sanitary, medical or surgical article comprising a cross-linked ester or a salt thereof according to claim 1.
Claim 21
Dependent Claim
27 words
A sanitary, medical or surgical article according to claim 19, comprising a film of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 22
Dependent Claim
26 words
A sanitary, medical or surgical article according to claim 19 comprising threads of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 23
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 1.
Claim 24
Dependent Claim
18 words
A cross-linked ester of hyaluronic acid according to claim 1, wherein said ester is a total cross-linked ester.
Claim 25
Dependent Claim
18 words
A cross-linked ester of hyaluronic acid according to claim 2, wherein said ester is a total cross-linked ester.
Claim 26
Dependent Claim
18 words
A cross-linked ester of hyaluronic acid according to claim 4, wherein said ester is a total cross-linked ester.
Claim 27
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 2, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 28
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 4, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 29
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 5, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 30
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 6, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 31
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 7, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 32
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 8, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 33
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 9, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 34
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 10, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 35
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 11, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 36
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 12, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 37
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 13, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 38
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 23, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 39
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 24, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 40
Dependent Claim
24 words
A pharmaceutical composition comprising an effective amount of a cross-linked ester according to claim 25, together with a pharmaceutically acceptable carrier, excipient or diluent.
Claim 41
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 1, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 42
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 2, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 43
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 4, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 44
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 5, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 45
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 6, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 46
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 7, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 47
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 8, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 48
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 9, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 49
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 10, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 50
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 11, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 51
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 12, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 52
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 13, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 53
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 23, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 54
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 24, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 55
Dependent Claim
26 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 25, together with a pharmaceutically acceptable carrier, excipient, or diluent.
Claim 56
Dependent Claim
27 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to claim 1 as a vehicle, in admixture with a pharmacologically active agent.
Claim 57
Dependent Claim
32 words
A pharmaceutical composition which comprises from 10 to 90% of a cross-linked ester according to any one of claim 2, 4-10, 11-13 and 23, 25, in admixture with a pharmacologically active agent.
Claim 58
Dependent Claim
31 words
A pharmaceutical composition which comprises from 10-90% by weight of a cross-linked ester according to claim 8, wherein said alcohol esterified with said non-cross-linked carboxy group is a pharmacologically active alcohol.
Claim 59
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 1.
Claim 60
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 2.
Claim 61
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 4.
Claim 62
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 5.
Claim 63
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 7.
Claim 64
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 10.
Claim 65
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 23.
Claim 66
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 24.
Claim 67
Dependent Claim
25 words
A cosmetic article which comprises as an active ingredient from 5-50% by weight of a cross-linked ester or a salt thereof according to claim 25.
Claim 68
Dependent Claim
19 words
A cosmetic article comprising as a cosmetic vehicle a cross-linked ester or a salt thereof according to claim 2.
Claim 69
Dependent Claim
19 words
A cosmetic article comprising as a cosmetic vehicle a cross-linked ester or a salt thereof according to claim 4.
Claim 70
Dependent Claim
19 words
A cosmetic article comprising as a cosmetic vehicle a cross-linked ester or a salt thereof according to claim 23.
Claim 71
Dependent Claim
19 words
A cosmetic article comprising as a cosmetic vehicle a cross-linked ester or a salt thereof according to claim 24.
Claim 72
Dependent Claim
18 words
A sanitary, medical or surgical article comprising a cross-linked ester or a salt thereof according to claim 2.
Claim 73
Dependent Claim
18 words
A sanitary, medical or surgical article comprising a cross-linked ester or a salt thereof according to claim 4.
Claim 74
Dependent Claim
18 words
A sanitary, medical or surgical article comprising a cross-linked ester or a salt thereof according to claim 23.
Claim 75
Dependent Claim
18 words
A sanitary, medical or surgical article comprising a cross-linked ester or a salt thereof according to claim 24.
Claim 76
Dependent Claim
27 words
A sanitary, medical or surgical article according to claim 2, comprising a film of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 77
Dependent Claim
27 words
A sanitary, medical or surgical article according to claim 4, comprising a film of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 78
Dependent Claim
27 words
A sanitary, medical or surgical article according to claim 23, comprising a film of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 79
Dependent Claim
27 words
A sanitary, medical or surgical article according to claim 24, comprising a film of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 80
Dependent Claim
26 words
A sanitary, medical or surgical article according to claim 2 comprising threads of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 81
Dependent Claim
26 words
A sanitary, medical or surgical article according to claim 4 comprising threads of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 82
Dependent Claim
26 words
A sanitary, medical or surgical article according to claim 23 comprising threads of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 83
Dependent Claim
26 words
A sanitary, medical or surgical article according to claim 24 comprising threads of a cross-linked ester wherein said aliphatic polyhydric alcohol is a therapeutically inert alcohol.
Claim 84
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 2.
Claim 85
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 4.
Claim 86
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 7.
Claim 87
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 8.
Claim 88
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 9.
Claim 89
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 10.
Claim 90
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 23.
Claim 91
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 24.
Claim 92
Dependent Claim
18 words
A capsule or microcapsule for medicaments comprising a cross-linked ester or a salt thereof according to claim 25.
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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) | 1993-09-17 | 1994-03-19 | 1994-09-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-09-17 | 1998-03-19 | 1998-09-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-09-17 | 2002-03-19 | 2002-09-18 | $7700.00 | Window Closed / Lapsed |