WO2005092929A8 - Esters butyriques d'acide hyaluronique faiblement substitues, procede d'elaboration et utilisation - Google Patents
Esters butyriques d'acide hyaluronique faiblement substitues, procede d'elaboration et utilisationInfo
- Publication number
- WO2005092929A8 WO2005092929A8 PCT/IB2005/000780 IB2005000780W WO2005092929A8 WO 2005092929 A8 WO2005092929 A8 WO 2005092929A8 IB 2005000780 W IB2005000780 W IB 2005000780W WO 2005092929 A8 WO2005092929 A8 WO 2005092929A8
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hyaluronic acid
- esters
- substitution
- butyric
- residues
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title abstract 6
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title abstract 5
- 229920002674 hyaluronan Polymers 0.000 title abstract 5
- 229960003160 hyaluronic acid Drugs 0.000 title abstract 5
- 238000006467 substitution reaction Methods 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 1
- 206010027457 Metastases to liver Diseases 0.000 abstract 1
- 230000001028 anti-proliverative effect Effects 0.000 abstract 1
- 125000000600 disaccharide group Chemical group 0.000 abstract 1
- 230000002440 hepatic effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000001394 metastastic effect Effects 0.000 abstract 1
- 206010061289 metastatic neoplasm Diseases 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne des esters butyriques d'acide hyaluronique dans lesquels les groupes hydroxyle de l'acide hyaluronique sont partiellement estérifiés par des groupes fonctionnels butyriques, caractérisés par un taux de substitution par les groupes fonctionnels butyriques inférieur à 0,1 (nombre de groupes fonctionnels butyriques rapporté au nombre d'unités disaccharide GIcNAc-GIcUA de l'acide hyaluronique). Ces esters faiblement substitués résultent d'un traitement mené en phase homogène dans des conditions anhydres, l'acide hyaluronique étant utilisé sous forme d'un sel d'azote quaternaire. Les esters de l'invention présentent un pouvoir antiproliférant supérieur à celui des esters correspondants plus fortement substitués. Ils sont particulièrement actifs contre les tumeurs primaires et métastatiques, notamment dans le cas de tumeurs primaires d'origine hépatique, ou de métastases hépatiques. Un autre aspect de l'invention concerne des compositions pharmaceutiques dont le principe actif est l'un au moins des esters de l'invention.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05718276A EP1781707A1 (fr) | 2004-03-29 | 2005-03-25 | Esters butyriques d'acide hyaluronique faiblement substitues, procede d'elaboration et utilisation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2004A000605 | 2004-03-29 | ||
| ITMI20040605 ITMI20040605A1 (it) | 2004-03-29 | 2004-03-29 | Esteri butirrici dell'acido ialuronico a basso grado di sostituzione procedimento per la loro preparazione ed uso |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2005092929A1 WO2005092929A1 (fr) | 2005-10-06 |
| WO2005092929A8 true WO2005092929A8 (fr) | 2006-03-02 |
Family
ID=34967092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2005/000780 WO2005092929A1 (fr) | 2004-03-29 | 2005-03-25 | Esters butyriques d'acide hyaluronique faiblement substitues, procede d'elaboration et utilisation |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1781707A1 (fr) |
| IT (1) | ITMI20040605A1 (fr) |
| WO (1) | WO2005092929A1 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1942117A1 (fr) * | 2006-12-29 | 2008-07-09 | Sigea S.R.L. | Dérivés de polysaccharides acides |
| ITMI20072237A1 (it) * | 2007-11-27 | 2009-05-28 | Sigea Srl | Esteri misti butirrico-formico di polisaccaridi acidi, loro preparazione ed uso come dermocosmetici |
| KR101078302B1 (ko) * | 2008-05-29 | 2011-10-31 | (주)프로넥스 | 약물전달체 |
| ITTO20110428A1 (it) | 2011-05-13 | 2012-11-14 | Rottapharm Spa | Esteri dell'acido ialuronico, loro preparazione ed uso in dermatologia |
| CZ2012842A3 (cs) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | Nanomicelární kompozice na bázi C6-C18-acylovaného hyaluronanu, způsob přípravy C6-C18-acylovaného hyaluronanu, způsob přípravy nanomicelární kompozice a stabilizované nanomicelární kompozice a použití |
| CZ304977B6 (cs) | 2013-11-21 | 2015-02-25 | Contipro Biotech S.R.O. | Nanovlákna obsahující fototvrditelný esterový derivát kyseliny hyaluronové nebo její soli, fototvrzená nanovlákna, způsob jejich syntézy, přípravek obsahující fototvrzená nanovlákna a jejich použití |
| CN103724455B (zh) * | 2013-12-11 | 2016-07-06 | 四川大学 | 一种透明质酸衍生物及其水凝胶的制备方法 |
| CZ305153B6 (cs) | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Konjugáty oligomeru kyseliny hyaluronové nebo její soli, způsob jejich přípravy a použití |
| CZ2014451A3 (cs) | 2014-06-30 | 2016-01-13 | Contipro Pharma A.S. | Protinádorová kompozice na bázi kyseliny hyaluronové a anorganických nanočástic, způsob její přípravy a použití |
| CN107106694B (zh) * | 2015-01-13 | 2020-09-22 | 西格亚有限公司 | 在水中用于制备透明质酸钠盐的丁酸酯类的方法 |
| CZ309295B6 (cs) | 2015-03-09 | 2022-08-10 | Contipro A.S. | Samonosný, biodegradabilní film na bázi hydrofobizované kyseliny hyaluronové, způsob jeho přípravy a použití |
| CZ306479B6 (cs) | 2015-06-15 | 2017-02-08 | Contipro A.S. | Způsob síťování polysacharidů s využitím fotolabilních chránicích skupin |
| CZ306662B6 (cs) | 2015-06-26 | 2017-04-26 | Contipro A.S. | Deriváty sulfatovaných polysacharidů, způsob jejich přípravy, způsob jejich modifikace a použití |
| CZ308106B6 (cs) | 2016-06-27 | 2020-01-08 | Contipro A.S. | Nenasycené deriváty polysacharidů, způsob jejich přípravy a jejich použití |
| CN116444695B (zh) * | 2022-12-27 | 2024-09-06 | 山东丰金美业科技有限公司 | 一种低成本、低分子量乙酰化透明质酸钠的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1286510B1 (it) * | 1996-11-29 | 1998-07-15 | Cooperativa Centro Ricerche Po | Esteri butirrici ad attivita' antiproliferativa e composizioni farmaceutiche che li contengono |
-
2004
- 2004-03-29 IT ITMI20040605 patent/ITMI20040605A1/it unknown
-
2005
- 2005-03-25 WO PCT/IB2005/000780 patent/WO2005092929A1/fr not_active Application Discontinuation
- 2005-03-25 EP EP05718276A patent/EP1781707A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI20040605A1 (it) | 2004-06-29 |
| WO2005092929A1 (fr) | 2005-10-06 |
| EP1781707A1 (fr) | 2007-05-09 |
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