US4965353A
Expired / Lapsed
US
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Polysaccharide esters and their salts
Assignee: Fidia Farmaceutici SpA
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Filing: 1989-04-19
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Granted: 1990-10-23
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Expires: 2009-04-19
Abstract
Abstract The invention concerns the esters of hyaluronic acid in which all or only a portion of the carboxylic groups of the acid are esterified, and the salts of the partial esters with metals or with pharmacologically acceptable organic bases. The compounds possess interesting and precious bioplastic and pharmaceutical properties and may be used in innumerable fields, including cosmetics, surgery and medicine. The invention also includes pharmaceutical preparations containing, as an active ingredient, one or more hyaluronic acid esters, or a salt thereof as described above, as well as medicaments containing: (1) a pharmacologically active substance or an association of pharmacologically active substances and (2) a carrying vehicle containing a total or partial ester of hyaluronic acid. The invention includes also various uses of the hyaluronic esters or of the above mentioned medicaments, such as in medicine, surgery or cosmetics. The invention also relates to a new procedure for the preparation of polysaccharide esters containing carboxylic groups, such as in particular the above mentioned hayluronic acid esters.
Inventors
- 👤 Francesco Della Valle
- 👤 Aurelio Romeo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 06:41
CPC Classifications
A; A61; A61K; A61K9/00; A61K9/0012; A61K9/0014; C; C07; C07H; C07H9/00; A61K47/00; A61K47/30; A61K47/36; A61K8/00; A61K8/18; A61K8/72; A61K8/73; A61K8/735; A61K9/0019; A61L; A61L15/00; A61L15/16; A61L15/22; A61L15/28; A61L17/00; A61L17/06; A61P; A61P17/00; A61P17/16; A61P29/00; A61Q; A61Q19/00; C08; C08B; C08B37/00; C08B37/006; C08B37/0063; C08B37/0072; C08L; C08L5/00; C08L5/08; A61Q19/08
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
25 words
A total ester of hyaluronic acid selected from the group consisting of the total benzyl ester, the total n-propyl ester and the total ethyl ester.
Claim 2
Dependent Claim
25 words
A total ester of hyaluronic acid selected from the group consisting of the total benzyl ester, the total n-propyl ester and the total ethyl ester.
Claim 3
Dependent Claim
14 words
A compound according to claim 1, wherein said ester is the total benzyl ester.
Claim 4
Dependent Claim
14 words
A compound according to claim 1, wherein said ester is the total n-propyl ester.
Claim 5
Dependent Claim
14 words
A compound according to claim 4, wherein said ester is the total ethyl ester.
Claim 6
Dependent Claim
16 words
A microcapsule for subcutaneous, intramuscular or intravenous injection comprised of an ester according to claim 1.
Claim 7
Dependent Claim
16 words
A microcapsule for subcutaneous, intramuscular or intravenous injection comprised of an ester according to claim 2.
Claim 8
Dependent Claim
16 words
A microcapsule for subcutaneous, intramuscular or intravenous injection comprised of an ester according to claim 3.
Claim 9
Dependent Claim
16 words
A microcapsule, for subcutaneous, intramuscular or intravenous injection comprised of an ester according to claim 4.
Claim 10
Dependent Claim
14 words
Threads for medical or surgical use comprised of an ester according to claim 1.
Claim 11
Dependent Claim
14 words
Threads for medical or surgical use comprised of an ester according to claim 2.
Claim 12
Dependent Claim
14 words
Threads for medical or surgical use comprised of an ester according to claim 3.
Claim 13
Dependent Claim
14 words
Threads for medical or surgical use comprised of an ester according to claim 4.
Claim 14
Dependent Claim
11 words
Gauzes comprised of threads according to any one of claims 9-12.
Claim 15
Dependent Claim
9 words
Sponges comprised of an ester according to claim 1.
Claim 16
Dependent Claim
9 words
Sponges comprised of an ester according to claim 2.
Claim 17
Dependent Claim
9 words
Sponges comprised of an ester according to claim 3.
Claim 18
Dependent Claim
9 words
Sponges comprised of an ester according to claim 4.
Claim 19
Dependent Claim
9 words
Films comprised of an ester according to claim 1.
Claim 20
Dependent Claim
9 words
Films comprised of an ester according to claim 2.
Claim 21
Dependent Claim
9 words
Films comprised of an ester according to claim 3.
Claim 22
Dependent Claim
9 words
Films comprised of an ester according to claim 4.
Claim 23
Dependent Claim
19 words
A partial ethyl ester of hyaluronic acid, wherein 75% of the carboxyl groups are esterified with an ethyl group.
Claim 24
Dependent Claim
19 words
A partial ethyl ester of hyaluronic acid, wherein 75% of the carboxyl groups are esterified with an ethyl group.
Claim 25
Dependent Claim
23 words
A partial ethyl ester according to claim 22, wherein 25% of the carboxyl groups are salified with an alkaline or alkaline earth metal.
Claim 26
Dependent Claim
13 words
A partial ethyl ester according to claim 23, wherein said metal is sodium.
Claim 27
Dependent Claim
19 words
A partial benzyl ester of hyaluronic acid, wherein 75% of the carboxyl groups are esterified with a benzyl group.
Claim 28
Dependent Claim
19 words
A partial benzyl ester of hyaluronic acid, wherein 75% of the carboxyl groups are esterified with a benzyl group.
Claim 29
Dependent Claim
23 words
A partial benzyl ester according to claim 25 wherein 25% of the carboxyl groups are salified with an alkaline of alkaline earth metal.
Claim 30
Dependent Claim
13 words
A partial benzyl ester according to claim 26, wherein said metal is sodium.
Claim 31
Dependent Claim
22 words
A cosmetic article comprised of an ester according to any one of claims 22-27 and one or more other cosmetically acceptable substances.
Claim 32
Dependent Claim
10 words
A microcapsule comprised of an ester according to claim 22.
Claim 33
Dependent Claim
10 words
A microcapsule comprised of an ester according to claim 23.
Claim 34
Dependent Claim
10 words
A microcapsule comprised of an ester according to claim 25.
Claim 35
Dependent Claim
13 words
A microcapsule according to claim 31 useful for subcutaneous intramuscular or intravenous injection.
Claim 36
Dependent Claim
10 words
A microcapsule comprised of an ester according to claim 26.
Claim 37
Dependent Claim
13 words
A microcapsule according to claim 33 useful for subcutaneous intramuscular or intravenous injection.
Claim 38
Dependent Claim
16 words
A microcapsule for subcutaneous intramuscular or intravenous injection comprised of an ester according to claim 27.
Claim 39
Dependent Claim
47 words
A microcapsule comprised of a total or partial ester of hyaluronic acid with an alcohol of the aliphatic araliphatic, cycloaliphatic or heterocyclic series, or a salt of such partial ester with an inorganic or organic base, with the exception of the total methyl ester of hyaluronic acid.
Claim 40
Dependent Claim
47 words
A microcapsule comprised of a total or partial ester of hyaluronic acid with an alcohol of the aliphatic araliphatic, cycloaliphatic or heterocyclic series, or a salt of such partial ester with an inorganic or organic base, with the exception of the total methyl ester of hyaluronic acid.
Claim 41
Dependent Claim
107 words
A microcapsule according to claim 36, wherein said alcohol of the aliphatic series has a maximum of 34 carbon atoms and are unsubstituted or substituted by one or two functional groups selected from the group consisting of amino, hydroxy, mercapto, aldehyde, keto, carboxy, hydrocarbyl, dihyrocarbylamino, ether, ester, thio-ether, thioester, acetal, ketal, carbalkoxy, carbamidic and 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 alcohols of the aliphatic series may be interrupted in the carbon atom chain by heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen.
Claim 42
Dependent Claim
44 words
A microcapsule according to claim 36, wherein said alcohol is a member selected from the group consisting of ethyl alcohol, propyl alcohol, isopropyl alcohol, normal butyl alcohol, isobutyl alcohol, tert-butyl alcohol, amyl alcohol, pentyl alcohol, hexyl alcohol, octyl alcohol, ethyleneglycol, propyleneglycol, butyleneglycol and glycerin.
Claim 43
Dependent Claim
82 words
A microcapsule according to claim 36, wherein said alcohol of the araliphatic series has only one benzene residue and in which the aliphatic chain has a maximum of 4 carbon atoms and in which the benzene residue may be substituted by 1 to 3 methyl by hydroxy groups, by halogen atoms, and in which the aliphatic chain may be substituted by one or two functions selected from the group consisting of free or mono or diethyl amino groups, pyrrolidinyl and piperidinyl groups.
Claim 44
Dependent Claim
25 words
A microcapsule according to claim 36, wherein said alcohol is a member selected from the group consisting of benzyl alcohol, phenethyl alcohol, ephedrine and adrenalin.
Claim 45
Dependent Claim
30 words
A microcapsule according to claim 36, wherein said alcohol is of the cycloaliphatic or aliphatic-cycloaliphatic series and derives from mono- or polycyclic hydrocarbides with a maximum of 34 carbon atoms.
Claim 46
Dependent Claim
28 words
A microcapsule according to any one of claims 29-41, wherein said partial ester of hyaluronic acid is salified with an alkaline or alkaline earth metal, magnesium or aluminum.
Claim 47
Dependent Claim
28 words
A microcapsule according to any one of claims 29-41, wherein said partial ester of hyaluronic acid is salified with a therapeutically acceptable aliphatic, araliphatic, cycloaliphatic or heterocyclic base.
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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) | 1993-10-22 | 1994-04-23 | 1994-10-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-10-22 | 1998-04-23 | 1998-10-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-10-22 | 2002-04-23 | 2002-10-23 | $7700.00 | Window Closed / Lapsed |