WO2021137837A1 - A novel viscoelastic formulation for osteoarthritis treatment and a production method thereof - Google Patents
A novel viscoelastic formulation for osteoarthritis treatment and a production method thereof Download PDFInfo
- Publication number
- WO2021137837A1 WO2021137837A1 PCT/TR2020/051471 TR2020051471W WO2021137837A1 WO 2021137837 A1 WO2021137837 A1 WO 2021137837A1 TR 2020051471 W TR2020051471 W TR 2020051471W WO 2021137837 A1 WO2021137837 A1 WO 2021137837A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- gel
- viscoelastic
- mixture
- crosslinked
- production method
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 201000008482 osteoarthritis Diseases 0.000 title claims abstract description 35
- 238000009472 formulation Methods 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 238000011282 treatment Methods 0.000 title abstract description 11
- 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 claims abstract description 78
- 229920002674 hyaluronan Polymers 0.000 claims abstract description 78
- 229960003160 hyaluronic acid Drugs 0.000 claims abstract description 78
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229920001287 Chondroitin sulfate Polymers 0.000 claims abstract description 27
- 229940059329 chondroitin sulfate Drugs 0.000 claims abstract description 27
- 208000002193 Pain Diseases 0.000 claims abstract description 15
- 210000001179 synovial fluid Anatomy 0.000 claims abstract description 11
- 230000003902 lesion Effects 0.000 claims abstract description 5
- 230000003247 decreasing effect Effects 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 210000000845 cartilage Anatomy 0.000 claims description 14
- 239000008055 phosphate buffer solution Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 13
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 210000003127 knee Anatomy 0.000 claims description 7
- 238000005461 lubrication Methods 0.000 claims description 7
- 238000004132 cross linking Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000011069 regeneration method Methods 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 5
- 229910021641 deionized water Inorganic materials 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 210000003423 ankle Anatomy 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 238000005429 filling process Methods 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 238000004659 sterilization and disinfection Methods 0.000 claims description 2
- 210000003857 wrist joint Anatomy 0.000 claims description 2
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 229920002385 Sodium hyaluronate Polymers 0.000 description 12
- 229940010747 sodium hyaluronate Drugs 0.000 description 12
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(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- Chemical compound [Na+].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 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 12
- 210000000988 bone and bone Anatomy 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 230000003993 interaction Effects 0.000 description 8
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 7
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 210000001503 joint Anatomy 0.000 description 6
- 230000008569 process Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229960005489 paracetamol Drugs 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 2
- 229920002683 Glycosaminoglycan Polymers 0.000 description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 210000001188 articular cartilage Anatomy 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960004544 cortisone Drugs 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 208000012659 Joint disease Diseases 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- -1 N-acetylamino group Chemical group 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 208000008558 Osteophyte Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 229940013181 advil Drugs 0.000 description 1
- 229940060515 aleve Drugs 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000011882 arthroplasty Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 230000003846 cartilage breakdown Effects 0.000 description 1
- 230000022159 cartilage development Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000001612 chondrocyte Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 229940029644 cymbalta Drugs 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 229960002866 duloxetine Drugs 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 201000010934 exostosis Diseases 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000037219 healthy weight Effects 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 210000000281 joint capsule Anatomy 0.000 description 1
- 230000008407 joint function Effects 0.000 description 1
- 210000000629 knee joint Anatomy 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- 230000003349 osteoarthritic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 238000000554 physical therapy Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940072651 tylenol Drugs 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
- C08L5/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
-
- 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
- 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
- A61K31/737—Sulfated polysaccharides, e.g. chondroitin sulfate, dermatan sulfate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2305/00—Characterised by the use of polysaccharides or of their derivatives not provided for in groups C08J2301/00 or C08J2303/00
- C08J2305/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
Definitions
- the considerable efficacy of the treatment provided by the viscoelastic gel of the present invention can be associated with the stimulation of chondrogenesis synergistically combined with the known benefits of viscoelastic treatment.
- Implantation of matrix of chondroitin sulfate and sodium hyaluronate can increase the continuity of naturally occurring chondrocytes and enable the damaged cartilage to self-regenerate by reconstituting its original state.
- chondroitin sulfate perfectly absorbs the positively charged tissue with the negatively charged sulfate groups inherent therein and the residence time is prolonged and therefore patient comfort is prolonged.
- combining cross-linked HA with chondroitin sulfate provides a longer duration of effectiveness compared to combinations comprising linear HA.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20910352.2A EP4084801A4 (en) | 2019-12-31 | 2020-12-31 | NOVEL VISCOELASTIC FORMULATION FOR THE TREATMENT OF OSTEOARTHRITIS AND METHOD FOR ITS PRODUCTION |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TR2019/22907 | 2019-12-31 | ||
| TR2019/22907A TR201922907A2 (tr) | 2019-12-31 | 2019-12-31 | Osteoartri̇t tedavi̇si̇ i̇çi̇n yeni̇ bi̇r vi̇skoelasti̇k formülasyonu ve bunun üreti̇m yöntemi̇ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2021137837A1 true WO2021137837A1 (en) | 2021-07-08 |
Family
ID=76687210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/TR2020/051471 WO2021137837A1 (en) | 2019-12-31 | 2020-12-31 | A novel viscoelastic formulation for osteoarthritis treatment and a production method thereof |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP4084801A4 (tr) |
| TR (2) | TR201922945A2 (tr) |
| WO (1) | WO2021137837A1 (tr) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997004012A1 (en) * | 1995-07-17 | 1997-02-06 | Q Med Ab | Polysaccharide gel composition |
| US20090143331A1 (en) * | 2007-11-30 | 2009-06-04 | Dimitrios Stroumpoulis | Polysaccharide gel formulation having increased longevity |
| WO2013144867A1 (en) * | 2012-03-30 | 2013-10-03 | Fidia Farmaceutici S.P.A. | Pharmaceutical formulations comprising chondroitin sulfate and hyaluronic acid derivatives |
| EP3081232A1 (en) * | 2013-12-09 | 2016-10-19 | New Medic Co., Ltd. | Hyaluronic acid gel composition having sustained release property |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090143348A1 (en) * | 2007-11-30 | 2009-06-04 | Ahmet Tezel | Polysaccharide gel compositions and methods for sustained delivery of drugs |
| CN107207784B (zh) * | 2015-02-13 | 2022-08-23 | (株)安道德玛 | 利用交联透明质酸水凝胶的微结构体及其的制造方法 |
| US11013670B2 (en) * | 2016-06-16 | 2021-05-25 | Endoderma Co., Ltd. | Hyaluronic acid microstructure having excellent solubility characteristics |
| KR20180035032A (ko) * | 2016-09-28 | 2018-04-05 | 주식회사 파마리서치프로덕트 | 가교 히알루론산을 포함하는 주사용 조성물 |
-
2019
- 2019-12-31 TR TR2019/22945A patent/TR201922945A2/tr unknown
- 2019-12-31 TR TR2019/22907A patent/TR201922907A2/tr unknown
-
2020
- 2020-12-31 WO PCT/TR2020/051471 patent/WO2021137837A1/en unknown
- 2020-12-31 EP EP20910352.2A patent/EP4084801A4/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997004012A1 (en) * | 1995-07-17 | 1997-02-06 | Q Med Ab | Polysaccharide gel composition |
| US20090143331A1 (en) * | 2007-11-30 | 2009-06-04 | Dimitrios Stroumpoulis | Polysaccharide gel formulation having increased longevity |
| WO2013144867A1 (en) * | 2012-03-30 | 2013-10-03 | Fidia Farmaceutici S.P.A. | Pharmaceutical formulations comprising chondroitin sulfate and hyaluronic acid derivatives |
| EP3081232A1 (en) * | 2013-12-09 | 2016-10-19 | New Medic Co., Ltd. | Hyaluronic acid gel composition having sustained release property |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP4084801A4 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP4084801A4 (en) | 2024-04-17 |
| TR201922907A2 (tr) | 2021-07-26 |
| EP4084801A1 (en) | 2022-11-09 |
| TR201922945A2 (tr) | 2021-07-26 |
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