KR20140034797A - 가교된 히알우론산을 기본으로 하는 양쪽성 재료, 그의 제조 방법, 포획된 활성 제제를 함유하는 재료, 그의 제조 방법, 및 상기 재료의 용도 - Google Patents
가교된 히알우론산을 기본으로 하는 양쪽성 재료, 그의 제조 방법, 포획된 활성 제제를 함유하는 재료, 그의 제조 방법, 및 상기 재료의 용도 Download PDFInfo
- Publication number
- KR20140034797A KR20140034797A KR1020137031065A KR20137031065A KR20140034797A KR 20140034797 A KR20140034797 A KR 20140034797A KR 1020137031065 A KR1020137031065 A KR 1020137031065A KR 20137031065 A KR20137031065 A KR 20137031065A KR 20140034797 A KR20140034797 A KR 20140034797A
- Authority
- KR
- South Korea
- Prior art keywords
- hyaluronan
- derivative
- group
- amine
- hyaluronic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229920002674 hyaluronan Polymers 0.000 title claims abstract description 128
- 238000000034 method Methods 0.000 title claims abstract description 55
- 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 abstract description 52
- 239000000463 material Substances 0.000 title abstract description 86
- 229960003160 hyaluronic acid Drugs 0.000 title abstract description 35
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 239000013543 active substance Substances 0.000 title abstract description 3
- 239000003814 drug Substances 0.000 claims abstract description 49
- 229940079593 drug Drugs 0.000 claims abstract description 48
- 238000013270 controlled release Methods 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 239000003102 growth factor Substances 0.000 claims abstract description 8
- 230000017423 tissue regeneration Effects 0.000 claims abstract description 4
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[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@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-MNSSHETKSA-N 0.000 claims description 106
- 229940099552 hyaluronan Drugs 0.000 claims description 93
- 239000011541 reaction mixture Substances 0.000 claims description 29
- 238000007254 oxidation reaction Methods 0.000 claims description 27
- 230000003647 oxidation Effects 0.000 claims description 20
- 150000003335 secondary amines Chemical group 0.000 claims description 20
- 230000001590 oxidative effect Effects 0.000 claims description 18
- 150000003141 primary amines Chemical class 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 238000006352 cycloaddition reaction Methods 0.000 claims description 13
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 10
- 210000001612 chondrocyte Anatomy 0.000 claims description 9
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims description 9
- 235000010378 sodium ascorbate Nutrition 0.000 claims description 9
- 229960005055 sodium ascorbate Drugs 0.000 claims description 9
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims description 9
- 239000000539 dimer Substances 0.000 claims description 8
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 229920001222 biopolymer Polymers 0.000 claims description 6
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- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 6
- 229920001059 synthetic polymer Polymers 0.000 claims description 6
- OYBOVXXFJYJYPC-UHFFFAOYSA-N 3-azidopropan-1-amine Chemical compound NCCCN=[N+]=[N-] OYBOVXXFJYJYPC-UHFFFAOYSA-N 0.000 claims description 5
- 102000004190 Enzymes Human genes 0.000 claims description 5
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- 206010052428 Wound Diseases 0.000 claims description 5
- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229940088623 biologically active substance Drugs 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- ASTSXCPVVNNSBI-UHFFFAOYSA-N (11-amino-3,6,9-trioxoundecyl)-diazonioazanide Chemical compound NCCC(=O)CCC(=O)CCC(=O)CC[N-][N+]#N ASTSXCPVVNNSBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005335 azido alkyl group Chemical group 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- VMXAIJCDNKFKPO-UHFFFAOYSA-N n-ethynylaniline Chemical compound C#CNC1=CC=CC=C1 VMXAIJCDNKFKPO-UHFFFAOYSA-N 0.000 claims description 3
- 229940035676 analgesics Drugs 0.000 claims description 2
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- 229940088710 antibiotic agent Drugs 0.000 claims description 2
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- 239000003193 general anesthetic agent Substances 0.000 claims description 2
- PVDGXEIFXYECGU-UHFFFAOYSA-N n-azidoaniline Chemical compound [N-]=[N+]=NNC1=CC=CC=C1 PVDGXEIFXYECGU-UHFFFAOYSA-N 0.000 claims description 2
- 238000010899 nucleation Methods 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000001085 cytostatic effect Effects 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- LPJOUIFUDMWNCT-UHFFFAOYSA-N undecane-3,6,9-trione Chemical compound CCC(=O)CCC(=O)CCC(=O)CC LPJOUIFUDMWNCT-UHFFFAOYSA-N 0.000 claims 1
- 239000000017 hydrogel Substances 0.000 description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
- 238000006243 chemical reaction Methods 0.000 description 62
- 239000000243 solution Substances 0.000 description 56
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 37
- 229920000642 polymer Polymers 0.000 description 37
- 230000008961 swelling Effects 0.000 description 31
- 238000009792 diffusion process Methods 0.000 description 26
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- 239000011780 sodium chloride Substances 0.000 description 23
- 210000004027 cell Anatomy 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- 238000006268 reductive amination reaction Methods 0.000 description 19
- 239000000872 buffer Substances 0.000 description 17
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 238000006467 substitution reaction Methods 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
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- 125000005647 linker group Chemical group 0.000 description 13
- 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 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- -1 carbonate ester Chemical class 0.000 description 12
- 239000011243 crosslinked material Substances 0.000 description 12
- 150000002466 imines Chemical class 0.000 description 12
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- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 11
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- 229920002385 Sodium hyaluronate Polymers 0.000 description 10
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- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzydamine Chemical compound C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 10
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- HNNIWKQLJSNAEQ-UHFFFAOYSA-N Benzydamine hydrochloride Chemical compound Cl.C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 HNNIWKQLJSNAEQ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 8
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- 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 description 3
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- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 2
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- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZPV2011-241 | 2011-04-24 | ||
| CZ20110241A CZ304072B6 (cs) | 2011-04-26 | 2011-04-26 | Amfoterní materiál na bázi sítované kyseliny hyaluronové, zpusob jeho prípravy, materiály obsahující aktivní cinidla uzavrené v síti hyaluronanu, zpusob jejich prípravy a jejich pouzití |
| PCT/CZ2012/000035 WO2012146218A1 (en) | 2011-04-24 | 2012-04-19 | Amphoteric materials based on crosslinked hyaluronic acid, method of preparation thereof, materials containing entrapped active agents, method of preparation thereof, and use of said materials |
Publications (1)
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| KR20140034797A true KR20140034797A (ko) | 2014-03-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020137031065A Withdrawn KR20140034797A (ko) | 2011-04-24 | 2012-04-19 | 가교된 히알우론산을 기본으로 하는 양쪽성 재료, 그의 제조 방법, 포획된 활성 제제를 함유하는 재료, 그의 제조 방법, 및 상기 재료의 용도 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20140120069A1 (enExample) |
| EP (1) | EP2702079A1 (enExample) |
| JP (1) | JP5818969B2 (enExample) |
| KR (1) | KR20140034797A (enExample) |
| BR (1) | BR112013027161A2 (enExample) |
| CZ (1) | CZ304072B6 (enExample) |
| RU (1) | RU2013151315A (enExample) |
| WO (1) | WO2012146218A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ302503B6 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
| CZ2009836A3 (cs) | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
| JPWO2012165462A1 (ja) * | 2011-05-31 | 2015-02-23 | 国立大学法人 東京大学 | ハイドロゲル及びその製造方法 |
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| CZ304512B6 (cs) | 2012-08-08 | 2014-06-11 | Contipro Biotech S.R.O. | Derivát kyseliny hyaluronové, způsob jeho přípravy, způsob jeho modifikace a použití |
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| CZ304654B6 (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 |
| US20150306237A1 (en) * | 2012-12-19 | 2015-10-29 | University Of Geneva | Hyaluronic acid-antioxidant conjugates and their uses |
| CZ2013913A3 (cs) * | 2013-11-21 | 2015-06-03 | Contipro Biotech S.R.O. | Objemný nanovlákenný materiál na bázi kyseliny hyaluronové, jejích solí nebo jejich derivátů, způsob jeho přípravy, způsob jeho modifikace, modifikovaný nanovlákenný materiál, nanovlákenný útvar a jejich použití |
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| 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 |
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| CZ2015398A3 (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 |
| CA3055985A1 (en) | 2017-03-22 | 2018-09-27 | Genentech, Inc. | Hydrogel cross-linked hyaluronic acid prodrug compositions and methods |
| JOP20190245A1 (ar) | 2017-04-20 | 2019-10-15 | Novartis Ag | أنظمة توصيل إطلاق مستدام تتضمن روابط بلا أثر لنقطة الربط |
| CN107335093A (zh) * | 2017-08-18 | 2017-11-10 | 四川大学 | 具有表面定向功能修饰涂层的多孔支架及其制备方法 |
| AR116566A1 (es) | 2018-10-03 | 2021-05-19 | Novartis Ag | Administración sostenida de polipéptidos similares a la angiopoyetina 3 |
| CN113667141B (zh) * | 2021-07-09 | 2023-10-03 | 深圳华源再生医学有限公司 | 抗蛋白粘附的海藻酸盐水凝胶及其制备方法和应用 |
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| NO169637C (no) | 1983-10-11 | 1992-07-22 | Fidia Spa | Fremgangsmaate for fremstilling av terapeutisk aktive hyaluronsyre-fraksjoner |
| IT1263393B (it) | 1993-07-30 | 1996-08-05 | Fidia Advanced Biopolymers Srl | Processo per la preparazione e purificazione di acido ialuronico ad alto peso molecolare |
| IT1317359B1 (it) * | 2000-08-31 | 2003-06-16 | Fidia Advanced Biopolymers Srl | Polisaccaridi percarbossilati, quali l'acido ialuronico, processo perla loro preparazione e loro impiego in campo farmaceutico e |
| IT1317358B1 (it) * | 2000-08-31 | 2003-06-16 | Fidia Advanced Biopolymers Srl | Derivati cross-linkati dell'acido ialuronico. |
| EP1934265A4 (en) | 2005-09-15 | 2009-06-24 | Univ Utah Res Found | POLYMER COMPOSITIONS AND METHODS OF MAKING AND USING SAME |
| EP3028677A1 (en) * | 2005-12-14 | 2016-06-08 | Anika Therapeutics Inc. | Treatment of arthritis and other musculoskeletal disorders with crosslinked hyaluronic acid |
| US20080008328A1 (en) | 2006-07-06 | 2008-01-10 | Sony Ericsson Mobile Communications Ab | Audio processing in communication terminals |
| ITMI20061726A1 (it) * | 2006-09-11 | 2008-03-12 | Fidia Farmaceutici | Derivati crosslinkati a base di acido ialuronico reticolato via click chemistry |
| EP2090592A1 (en) | 2007-07-31 | 2009-08-19 | OctoPlus Sciences B.V. | Biodegradable hydrogels based on click chemistry |
| ITRM20080636A1 (it) * | 2008-11-28 | 2010-05-29 | Univ Palermo | Procedimento per la produzione di derivati funzionalizzati dell acido ialuronico e relativi idrogeli. |
| US8790702B2 (en) * | 2009-07-30 | 2014-07-29 | Carbylan Therapeutics, Inc. | Modified hyaluronic acid polymer compositions and related methods |
| CZ302503B6 (cs) * | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Zpusob prípravy derivátu kyseliny hyaluronové oxidovaného v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd a zpusob jeho modifikace |
| CZ2009836A3 (cs) * | 2009-12-11 | 2011-06-22 | Contipro C A.S. | Derivát kyseliny hyaluronové oxidovaný v poloze 6 glukosaminové cásti polysacharidu selektivne na aldehyd, zpusob jeho prípravy a zpusob jeho modifikace |
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2011
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- 2012-04-19 BR BR112013027161A patent/BR112013027161A2/pt not_active IP Right Cessation
- 2012-04-19 WO PCT/CZ2012/000035 patent/WO2012146218A1/en not_active Ceased
- 2012-04-19 RU RU2013151315/05A patent/RU2013151315A/ru not_active Application Discontinuation
- 2012-04-19 US US14/113,527 patent/US20140120069A1/en not_active Abandoned
- 2012-04-19 KR KR1020137031065A patent/KR20140034797A/ko not_active Withdrawn
- 2012-04-19 JP JP2014506754A patent/JP5818969B2/ja not_active Expired - Fee Related
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| CZ2011241A3 (cs) | 2012-11-07 |
| RU2013151315A (ru) | 2015-05-27 |
| EP2702079A1 (en) | 2014-03-05 |
| WO2012146218A1 (en) | 2012-11-01 |
| JP5818969B2 (ja) | 2015-11-18 |
| BR112013027161A2 (pt) | 2017-12-12 |
| US20140120069A1 (en) | 2014-05-01 |
| JP2014512445A (ja) | 2014-05-22 |
| CZ304072B6 (cs) | 2013-09-25 |
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