ITFI980104A1 - STABILIZED COMPOSITIONS CONTAINING HYALURONIC ACID, THEIR PREPARATION AND USE - Google Patents
STABILIZED COMPOSITIONS CONTAINING HYALURONIC ACID, THEIR PREPARATION AND USE Download PDFInfo
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- ITFI980104A1 ITFI980104A1 IT98FI000104A ITFI980104A ITFI980104A1 IT FI980104 A1 ITFI980104 A1 IT FI980104A1 IT 98FI000104 A IT98FI000104 A IT 98FI000104A IT FI980104 A ITFI980104 A IT FI980104A IT FI980104 A1 ITFI980104 A1 IT FI980104A1
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- Italy
- Prior art keywords
- hyaluronic acid
- composition according
- polymer
- composition
- comprised
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 28
- 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 claims description 21
- 229920002674 hyaluronan Polymers 0.000 title claims description 17
- 229960003160 hyaluronic acid Drugs 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 7
- 238000002316 cosmetic surgery Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229920002125 Sokalan® Polymers 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- -1 amyl isoamyl ester Chemical class 0.000 claims 1
- 239000008223 sterile water Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- KIUKXJAPPMFGSW-YXBJCWEESA-N (2s,4s,5r,6s)-6-[(2s,3r,5s,6r)-3-acetamido-2-[(3s,4r,5r,6r)-6-[(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]1C(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(O[C@@H]3[C@@H]([C@@H](O)C(O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)C(C(O)=O)O1 KIUKXJAPPMFGSW-YXBJCWEESA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- 208000032544 Cicatrix Diseases 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 231100000241 scar Toxicity 0.000 description 2
- 230000037387 scars Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 230000002101 lytic effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/728—Hyaluronic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0023—Polysaccharides
Description
Domanda di brevetto per invenzione industriale dal titolo: Patent application for industrial invention entitled:
Composizioni stabilizzate contenenti acido ialuronico, loro preparazione ed uso Stabilized compositions containing hyaluronic acid, their preparation and use
Campo dell’invenzione Field of the invention
La presente invenzione si riferisce a composizioni stabilizzate contenenti acido ialuronico, o i suoi derivati comunemente usati in chirurgia estetica, ed un carbossivinilpolimero capaci di resistere più a lungo all'azione demolitiva da parte degli enzimi a cui sono sottoposti gli impianti costituiti da tali materiali una volta applicati ai pazienti. The present invention refers to stabilized compositions containing hyaluronic acid, or its derivatives commonly used in cosmetic surgery, and a carboxyvinyl polymer capable of withstanding longer the demolition action by the enzymes to which implants made of such materials are subjected once applied to patients.
Stato dell'arte State of the art
L'acido ialuronico è un polisaccaride presente naturalmente nel tessuto umano dove si forma in continuazione. Viste le sue proprietà viscoelastiche esso è da tempo utilizzato nei trattamenti di chirurgia estetica per l'eliminazione di rughe, solchi, cicatrici e simili. Hyaluronic acid is a polysaccharide naturally present in human tissue where it is formed continuously. Given its viscoelastic properties, it has long been used in cosmetic surgery treatments for the elimination of wrinkles, furrows, scars and the like.
L'acido ialuronico viene iniettato per mezzo di apposite fiale siringhe nella zona sottocutanea in cui è presente l’inestetismo da correggere e va a costituire uno spessore che elimina le pieghe dovute a rughe o cicatrici. Hyaluronic acid is injected by means of special syringe vials into the subcutaneous area where the imperfection to be corrected is present and forms a thickness that eliminates creases due to wrinkles or scars.
Tuttavia l'acido ialuronico subisce l’azione demolitiva degli enzimi naturali che lo attaccano sui gruppi funzionali -COOH ed -OH per cui dopo breve tempo è necessario ripetere l’intervento. However, hyaluronic acid undergoes the destructive action of natural enzymes that attack it on the functional groups -COOH and -OH so after a short time it is necessary to repeat the operation.
Per ovviare a questo inconveniente si è pensato di sostituire l'acido ialuronico con suoi derivati come esteri, sali, derivati cross lineati ma anche queste soluzioni benché allunghino il tempo di persistenza dell'impianto sono risultati insoddisfacenti in quanto la loro durata è sempre troppo limitata. To obviate this drawback, it was decided to replace hyaluronic acid with its derivatives such as esters, salts, cross-lined derivatives but even these solutions, although they lengthen the persistence time of the implant, were unsatisfactory as their duration is always too limited. .
E’ ovvio quindi l'interesse a poter disporre di composizioni a base di acido ialuronico o suoi derivati capaci di resistere più a lungo all'azione litica degli enzimi e quindi capaci di allungare i tempi necessari per i successivi interventi correttivi. It is therefore obvious the interest in having compositions based on hyaluronic acid or its derivatives capable of resisting the lytic action of enzymes for longer and therefore capable of extending the time required for subsequent corrective interventions.
Descrizione dettagliata dell’invenzione Detailed description of the invention
La presente invenzione permette di ovviare agli inconvenienti suddetti per mezzo di composizioni costituite da acido ialuronico (o i suoi derivati comunemente impiegati nella chirurgia estetica e quindi farmaceuticamente accettabili) e da un carbossivinilpolimero di formula generale (I) The present invention allows to overcome the aforementioned drawbacks by means of compositions consisting of hyaluronic acid (or its derivatives commonly used in cosmetic surgery and therefore pharmaceutically acceptable) and a carboxyvinylpolymer of general formula (I)
ove n è compreso fra 50 - 55.000 ed avente un peso molecolare compreso fra 10.000 e 10.000:000, preferibilmente 5.000.000 - 6.000.000. where n is comprised between 50 - 55,000 and having a molecular weight comprised between 10,000 and 10,000: 000, preferably 5,000,000 - 6,000,000.
Preferibilmente il carbossivinilpolimero suddetto è presente in concentrazioni comprese fra 0,001 - 5% (quantità espressa in peso sul totale della composizione), più preferibilmente fra 0,01 - 0,2%. Preferably the aforesaid carboxyvinylpolymer is present in concentrations ranging from 0.001 - 5% (quantity expressed by weight on the total composition), more preferably between 0.01 - 0.2%.
Fra i derivati dell’acido ialuronico impiegati nella chirurgia estetica utili secondo l’invenzione possiamo ricordare in particolare gli esteri (come ad esempio metilico, etilico, isopropilico, butilico, amilico, isoamilico), i sali organici od inorganici farmaceuticamente accettabili (ad esempio di sodio o trietilammina), i composti cross lincati (ad esempio con etilen glicole dimetacrilato, aldeide glutarica, divinilsulfone). Among the derivatives of hyaluronic acid used in cosmetic surgery useful according to the invention we can mention in particular the esters (such as for example methyl, ethyl, isopropyl, butyl, amyl, isoamyl), the pharmaceutically acceptable organic or inorganic salts (for example of sodium or triethylamine), cross-linked compounds (for example with ethylene glycol dimethacrylate, glutaric aldehyde, divinylsulfone).
La composizione secondo l’invenzione viene preparata con i metodi tradizionali noti nell’arte. Ad esempio si mescolano in un miscelatore l'acido ialuronico (o il derivato corrispondente) con l’opportuna quantità di polimero. Nel caso in cui il derivato dell’acido ialuronico utilizzato è un estere la miscelazione è condotta in presenza, di un catalizzatore come ad esempio acido paratoluensolfonico o ioduro di etile. Si scioglie la miscela cosi ottenuta in acqua sterile alla concentrazione voluta, la soluzione così ottenuta è filtrata attraverso un filtro di nailon caricato positivamente; la soluzione così ottenuta è liofilizzata ed il solido asciutto è ridisciolto, in concentrazione opportuna, in acqua sterile sotto agitazione fino ad ottenere un gel viscoelastico trasparente. The composition according to the invention is prepared with the traditional methods known in the art. For example, hyaluronic acid (or the corresponding derivative) is mixed with the appropriate amount of polymer in a mixer. If the hyaluronic acid derivative used is an ester, the mixing is carried out in the presence of a catalyst such as paratoluenesulfonic acid or ethyl iodide. The mixture thus obtained is dissolved in sterile water at the desired concentration, the solution thus obtained is filtered through a positively charged nylon filter; the solution thus obtained is lyophilized and the dry solid is redissolved, in a suitable concentration, in sterile water under stirring until a transparent viscoelastic gel is obtained.
Il prodotto così ottenuto è caricato nelle apposite fiale siringhe pronto uso preferibilmente nelle quantità: 0,5; 1; 1,5; 2 mi. The product thus obtained is loaded into the appropriate ready-to-use syringe vials preferably in the quantities: 0.5; 1; 1.5; 2 mi.
Esempio 1 Example 1
A 30 g di acido ialuronico sale sodico vengono aggiunti 10 g di CARBOPOOL 940 (polimero di formula (I) prodotto dalia Goodrich avente PM 5.000.Ò00) e la miscela è sciòlta in acqua sterile (10 It) e . filtrata attraverso un filtro in nailon 66 da 0,2 micron alla concentrazione totale dello 0,4%. To 30 g of hyaluronic acid sodium salt are added 10 g of CARBOPOOL 940 (polymer of formula (I) produced by Goodrich having MW 5,000.Ò00) and the mixture is dissolved in sterile water (10 It) e. filtered through a 0.2 micron nylon 66 filter at a total concentration of 0.4%.
La soluzione è liofilizzata fino ad ottenere un solido asciutto che viene ridisciolto in acqua sterile all’1,3% sotto agitazione fino ad ottenere un gel viscoelastico trasparente della consistenza voluta, The solution is freeze-dried until a dry solid is obtained which is redissolved in 1.3% sterile water under stirring until a transparent viscoelastic gel of the desired consistency is obtained,
il prodotto è infine caricato in fiale siringhe pronto uso da:0,5, 1, 1,5 e 2 mi. Procedendo analogamente a come sopra indicato si sono preparate composizioni in cui la concentrazione iniziale di polimero era dello 0,005%, 0,08%, 2%. the product is finally loaded into ready-to-use syringe vials of: 0.5, 1, 1.5 and 2 ml. Proceeding in the same way as indicated above, compositions were prepared in which the initial polymer concentration was 0.005%, 0.08%, 2%.
Esempio 2 Example 2
Si è proceduto come descritto nell'esempio 1 ma utilizzando l’acido ialuronico al posto del sale sodico corrispondente. Si sono preparate le corrispondenti composizioni utilizzando le diverse quantità di polimero come indicato nell’esempio 1. We proceeded as described in example 1 but using hyaluronic acid instead of the corresponding sodium salt. The corresponding compositions were prepared using the different quantities of polymer as indicated in example 1.
Esempio 3 Example 3
Si è proceduto come descritto nell’esempio 1 ma utilizzando al posto dell'acido ialuronico sale sodico il corrispondente sale organico di trietilammina. Si sono preparate le corrispondenti composizioni utilizzando le diverse quantità di polimero come indicato nell’esempio 1. We proceeded as described in example 1 but using the corresponding organic salt of triethylamine instead of the hyaluronic acid sodium salt. The corresponding compositions were prepared using the different quantities of polymer as indicated in example 1.
Esempio 4 Example 4
Si è proceduto come descritto nell’esempio 1 ma utilizzando al posto dell’acido ialuronico sale sodico acido. ialuronico cross lineato con etilen glicole dimetacrilato. Si sono preparate le corrispondenti composizioni utilizzando le diverse quantità di polimero come indicato nell'esempio 1. We proceeded as described in example 1 but using sodium acid salt instead of hyaluronic acid. cross-laced hyaluronic acid with ethylene glycol dimethacrylate. The corresponding compositions were prepared using the different quantities of polymer as indicated in Example 1.
Esempio 5 Example 5
Si è proceduto come descritto nell’esempio 1 ma utilizzando al posto dell’acido ialuronico sale sodico rispettivamente i corrispondenti esteri metilico, etilico, isopropilico, butilico, amilico, isoamilico dell' acido ialuronico in presenza di acido paratoluensolfonico (6%).. Si sono preparate le corrispondenti composizioni utilizzando le diverse quantità di polimero come indicato nell’esempio 1. . We proceeded as described in example 1 but using sodium salt instead of hyaluronic acid, respectively, the corresponding methyl, ethyl, isopropyl, butyl, amyl, isoamyl esters of hyaluronic acid in the presence of paratoluenesulfonic acid (6%). the corresponding compositions are prepared using the different quantities of polymer as indicated in Example 1..
L’uso delle composizioni sopra descritte nelle normali applicazioni di chirurgia 9. Kit costituiti da almeno due fiale siringhe pronto uso contenenti quantità uguali o diverse delle composizioni secondo l'invenzione a concentrazioni uguali o diverse tra loro. The use of the compositions described above in normal surgical applications 9. Kits consisting of at least two ready-to-use syringe vials containing equal or different quantities of the compositions according to the invention at equal or different concentrations.
10. Uso delle composizioni secondo la rivendicazione 1 per trattamenti di chirurgia estetica. 10. Use of the compositions according to claim 1 for cosmetic surgery treatments.
estetica ha consentito di ottenere ottimi risultati, decisamente superiori a quelli. di composizioni analoghe prive del polimero. aesthetics has allowed us to obtain excellent results, much higher than those. of analogous compositions devoid of the polymer.
La presente invenzione si riferisce inoltre a kit costituiti da almeno due fiale siringhe pronto uso contenenti quantità uguali o diverse delle composizioni secondo l’invenzione a concentrazioni uguali o diverse in modo da coprire le più diverse esigenze di uso, The present invention also refers to kits consisting of at least two ready-to-use syringe vials containing equal or different quantities of the compositions according to the invention at equal or different concentrations in order to cover the most diverse needs of use,
Claims (8)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98FI000104A ITFI980104A1 (en) | 1998-05-04 | 1998-05-04 | STABILIZED COMPOSITIONS CONTAINING HYALURONIC ACID, THEIR PREPARATION AND USE |
| AU40361/99A AU4036199A (en) | 1998-05-04 | 1999-05-03 | Stabilised compositions containing hyaluronic acid, their preparation and use |
| PCT/EP1999/002987 WO1999056799A1 (en) | 1998-05-04 | 1999-05-03 | Stabilised compositions containing hyaluronic acid, their preparation and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98FI000104A ITFI980104A1 (en) | 1998-05-04 | 1998-05-04 | STABILIZED COMPOSITIONS CONTAINING HYALURONIC ACID, THEIR PREPARATION AND USE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ITFI980104A1 true ITFI980104A1 (en) | 1999-11-04 |
Family
ID=11352531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT98FI000104A ITFI980104A1 (en) | 1998-05-04 | 1998-05-04 | STABILIZED COMPOSITIONS CONTAINING HYALURONIC ACID, THEIR PREPARATION AND USE |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU4036199A (en) |
| IT (1) | ITFI980104A1 (en) |
| WO (1) | WO1999056799A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050288458A1 (en) | 2002-07-29 | 2005-12-29 | Klemarczyk Philip T | Reworkable thermosetting resin composition |
| US7008626B2 (en) * | 2001-11-05 | 2006-03-07 | Seikagaku Corporation | Medical composition for protuberance of epithelium |
| US20060140988A1 (en) * | 2004-12-23 | 2006-06-29 | Guohua Chen | Visco-supplement composition and methods |
| EP2324064B1 (en) | 2008-09-02 | 2017-11-08 | Tautona Group LP | Threads of hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
| FR2954945B1 (en) * | 2010-01-04 | 2012-01-06 | Oreal | COSMETIC OR DERMATOLOGICAL COMPOSITION, COSMETIC PROCESSING METHOD, AND HYALURONIC ACID DERIVATIVE |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4716224A (en) * | 1984-05-04 | 1987-12-29 | Seikagaku Kogyo Co. Ltd. | Crosslinked hyaluronic acid and its use |
| US5143724A (en) * | 1990-07-09 | 1992-09-01 | Biomatrix, Inc. | Biocompatible viscoelastic gel slurries, their preparation and use |
| IT1260154B (en) * | 1992-07-03 | 1996-03-28 | Lanfranco Callegaro | HYALURONIC ACID AND ITS DERIVATIVES IN INTERPENETRATING POLYMERS (IPN) |
| IT1273742B (en) * | 1994-08-01 | 1997-07-09 | Lifegroup Spa | HIGH BIO ADHESIVE AND MUCO ADHESIVE COMPOSITIONS USEFUL FOR THE TREATMENT OF EPITALS AND MUCOSES |
| FR2733426B1 (en) * | 1995-04-25 | 1997-07-18 | Debacker Yves | MEDICAL DEVICE FOR FILLING SKIN VOLUME DEFORMATIONS SUCH AS WRINKLES AND SCARS BY INJECTION OF 2 DIFFERENT PHYSICO-CHEMICAL FORMS OF A BIOLOGICAL POLYMER |
-
1998
- 1998-05-04 IT IT98FI000104A patent/ITFI980104A1/en unknown
-
1999
- 1999-05-03 WO PCT/EP1999/002987 patent/WO1999056799A1/en active Application Filing
- 1999-05-03 AU AU40361/99A patent/AU4036199A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999056799A1 (en) | 1999-11-11 |
| AU4036199A (en) | 1999-11-23 |
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