WO2005092929A8 - Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and use - Google Patents
Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and useInfo
- 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
The invention relates to hyaluronic acid butyric esters in which the hydroxyl groups of hyaluronic acid are partially esterified with butyric residues, characterised by a degree of substitution with butyric residues (ratio of number of butyric acid residues to disaccharide units GIcNAc-GIcUA of hyaluronic acid) being equal or below 0.1. These esters with low degree of substitution are obtained by means of a process carried out in the homogeneous phase under anhydrous conditions, wherein hyaluronic acid is used in the form of a quaternary nitrogen salt. The esters of the invention have a greater antiproliferative activity than corresponding esters with higher degree of substitution, and are particularly active against primary and metastatic tumours, where said tumours are primary of hepatic origin, or are hepatic metastases. A further aspect of the invention is represented by pharmaceutical compositions, containing as active principle at least one of the esters described.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05718276A EP1781707A1 (en) | 2004-03-29 | 2005-03-25 | Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and use |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2004A000605 | 2004-03-29 | ||
| ITMI20040605 ITMI20040605A1 (en) | 2004-03-29 | 2004-03-29 | BUTYRICAL ESTERS OF HYALURONIC ACID WITH LOW DEGREE OF SUBSTITUTION PROCEDURE FOR THEIR PREPARATION AND USE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2005092929A1 WO2005092929A1 (en) | 2005-10-06 |
| WO2005092929A8 true WO2005092929A8 (en) | 2006-03-02 |
Family
ID=34967092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB2005/000780 WO2005092929A1 (en) | 2004-03-29 | 2005-03-25 | Hyaluronic acid butyric esters with a low degree of substitution, procedure for their preparation and use |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1781707A1 (en) |
| IT (1) | ITMI20040605A1 (en) |
| WO (1) | WO2005092929A1 (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1942117A1 (en) * | 2006-12-29 | 2008-07-09 | Sigea S.R.L. | Derivatives of acid polysaccharides |
| ITMI20072237A1 (en) * | 2007-11-27 | 2009-05-28 | Sigea Srl | MIXED BUTIRRIC-FORMAL ESTERS OF ACID POLYSACCHARIDES, THEIR PREPARATION AND USE AS DERMOCOSMETICS |
| KR101078302B1 (en) * | 2008-05-29 | 2011-10-31 | (주)프로넥스 | Drug Delivery System |
| ITTO20110428A1 (en) | 2011-05-13 | 2012-11-14 | Rottapharm Spa | ESTERS OF HYALURONIC ACID, THEIR PREPARATION AND USE IN DERMATOLOGY |
| CZ2012842A3 (en) | 2012-11-27 | 2014-08-20 | Contipro Biotech S.R.O. | C6-C18-acylated hyaluronate-based nanomicellar composition, process for preparing C6-C18-acylated hyaluronate, process for preparing nanomicellar composition and stabilized nanomicellar composition as well as use thereof |
| CZ304977B6 (en) | 2013-11-21 | 2015-02-25 | Contipro Biotech S.R.O. | Nanofibers comprising photocurable ester derivative of hyaluronic acid or a salt thereof, photocured nanofibers, method of their synthesis, composition comprising photocured nanofibers and use thereof |
| CN103724455B (en) * | 2013-12-11 | 2016-07-06 | 四川大学 | A kind of preparation method of derivatives of hyaluronic acids and hydrogel thereof |
| CZ305153B6 (en) | 2014-03-11 | 2015-05-20 | Contipro Biotech S.R.O. | Conjugates of hyaluronic acid oligomer or a salt thereof, process for their preparation and use |
| CZ2014451A3 (en) | 2014-06-30 | 2016-01-13 | Contipro Pharma A.S. | Antitumor composition based on hyaluronic acid and inorganic nanoparticles, process of its preparation and use |
| CN107106694B (en) * | 2015-01-13 | 2020-09-22 | 西格亚有限公司 | Process for the preparation of butyric esters of hyaluronic acid sodium salt in water |
| CZ309295B6 (en) | 2015-03-09 | 2022-08-10 | Contipro A.S. | Self-supporting, biodegradable film based on hydrophobized hyaluronic acid, method of its preparation and use |
| CZ306479B6 (en) | 2015-06-15 | 2017-02-08 | Contipro A.S. | A method of crosslinking polysaccharides by using photolabile protecting groups |
| CZ306662B6 (en) | 2015-06-26 | 2017-04-26 | Contipro A.S. | Sulphated polysaccharides derivatives, the method of their preparation, the method of their modification and the use |
| CZ308106B6 (en) | 2016-06-27 | 2020-01-08 | Contipro A.S. | Unsaturated derivatives of polysaccharides, preparing and using them |
| CN116444695B (en) * | 2022-12-27 | 2024-09-06 | 山东丰金美业科技有限公司 | Preparation method of low-cost low-molecular-weight acetylated sodium hyaluronate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1286510B1 (en) * | 1996-11-29 | 1998-07-15 | Cooperativa Centro Ricerche Po | BUTYRIC ESTERS WITH ANTI-PROLIFERATIVE ACTIVITY AND PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM |
-
2004
- 2004-03-29 IT ITMI20040605 patent/ITMI20040605A1/en unknown
-
2005
- 2005-03-25 WO PCT/IB2005/000780 patent/WO2005092929A1/en not_active Application Discontinuation
- 2005-03-25 EP EP05718276A patent/EP1781707A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI20040605A1 (en) | 2004-06-29 |
| WO2005092929A1 (en) | 2005-10-06 |
| EP1781707A1 (en) | 2007-05-09 |
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Free format text: IN PCT GAZETTE 40/2005 UNDER (71) ADD "PERBELLINI, GIULIA (HEIRESS OF THE DECEASED INVENTOR) [IT/IT]; VIA IV NOVEMBRE, 14, I-37126 VERONA (IT)." |
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