JP5518709B2 - 調節可能架橋ヒアルロン酸組成物 - Google Patents
調節可能架橋ヒアルロン酸組成物 Download PDFInfo
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- JP5518709B2 JP5518709B2 JP2010520076A JP2010520076A JP5518709B2 JP 5518709 B2 JP5518709 B2 JP 5518709B2 JP 2010520076 A JP2010520076 A JP 2010520076A JP 2010520076 A JP2010520076 A JP 2010520076A JP 5518709 B2 JP5518709 B2 JP 5518709B2
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- Prior art keywords
- hyaluronic acid
- crosslinker
- peg
- present
- cross
- 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.)
- Expired - Fee Related
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- 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 99
- 229920002674 hyaluronan Polymers 0.000 title claims description 93
- 229960003160 hyaluronic acid Drugs 0.000 title claims description 93
- 239000000203 mixture Substances 0.000 title claims description 60
- 229920001223 polyethylene glycol Polymers 0.000 claims description 78
- 239000002202 Polyethylene glycol Substances 0.000 claims description 77
- 239000003431 cross linking reagent Substances 0.000 claims description 43
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 210000004872 soft tissue Anatomy 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 239000011248 coating agent Substances 0.000 claims description 7
- 239000004971 Cross linker Substances 0.000 description 68
- 230000001588 bifunctional effect Effects 0.000 description 20
- 150000002118 epoxides Chemical class 0.000 description 19
- 239000000499 gel Substances 0.000 description 17
- 239000002245 particle Substances 0.000 description 17
- 210000003491 skin Anatomy 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000017 hydrogel Substances 0.000 description 8
- 230000003416 augmentation Effects 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 230000007515 enzymatic degradation Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000003190 augmentative effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- 208000032544 Cicatrix Diseases 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 108010003272 Hyaluronate lyase Proteins 0.000 description 1
- 102000001974 Hyaluronidases Human genes 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002385 Sodium hyaluronate Polymers 0.000 description 1
- FZQSLXQPHPOTHG-UHFFFAOYSA-N [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 Chemical compound [K+].[K+].O1B([O-])OB2OB([O-])OB1O2 FZQSLXQPHPOTHG-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 229920000249 biocompatible polymer Polymers 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002773 hyaluronidase Drugs 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 230000037387 scars Effects 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 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 1
- 238000003860 storage Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
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
-
- 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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/20—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/34—Materials or treatment for tissue regeneration for soft tissue reconstruction
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Transplantation (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Materials For Medical Uses (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cosmetics (AREA)
- Epoxy Resins (AREA)
- Medicinal Preparation (AREA)
Description
1gのヒアルロン酸ナトリウムファイバー(NaHA、Mw=0.5〜3MDa)を、5〜10gの0.01〜1%水酸化ナトリウム溶液と混合し、混合物を1〜5時間水和させる。次に、20〜200mgの1,4-ブタンジオールジグリシジルエーテル(BDDE)および0.05〜2gの4-Arm Star PEGエポキシド(Mw=200〜10,000Da)を、NaHAゲルに添加する。混合物を機械的に均質化し、次に、40〜70℃のオーブンに1〜10時間入れる。得られた架橋ヒドロゲルを、等モル量の塩酸で中和し、リン酸塩緩衝液(PBS、pH=7.4)中で膨潤させる。次に、このヒドロゲルを機械的に均質化しうる。
Claims (8)
- 架橋ヒアルロン酸を、ポリエチレングリコール系ペンダントコーティングでコーティングすることをさらに含んで成る請求項1に記載の方法。
- 請求項1または2に記載の方法によって得られる軟組織増大用の組成物。
- ヒアルロン酸が、少なくとも2種類のポリエチレングリコール系架橋剤で架橋される請求項4に記載の組成物。
- ポリエチレングリコール系ペンダントコーティングをさらに含んで成る請求項4または5に記載の組成物。
- 皮膚フィラーとして使用される請求項4〜6のいずれかに記載の組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US95277007P | 2007-07-30 | 2007-07-30 | |
US60/952,770 | 2007-07-30 | ||
PCT/US2008/070985 WO2009018076A1 (en) | 2007-07-30 | 2008-07-24 | Tunably crosslinked hyaluronic acid compositions |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014075988A Division JP2014194018A (ja) | 2007-07-30 | 2014-04-02 | 調節可能架橋ヒアルロン酸組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010535277A JP2010535277A (ja) | 2010-11-18 |
JP5518709B2 true JP5518709B2 (ja) | 2014-06-11 |
Family
ID=39769477
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010520076A Expired - Fee Related JP5518709B2 (ja) | 2007-07-30 | 2008-07-24 | 調節可能架橋ヒアルロン酸組成物 |
JP2014075988A Pending JP2014194018A (ja) | 2007-07-30 | 2014-04-02 | 調節可能架橋ヒアルロン酸組成物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014075988A Pending JP2014194018A (ja) | 2007-07-30 | 2014-04-02 | 調節可能架橋ヒアルロン酸組成物 |
Country Status (12)
Country | Link |
---|---|
US (2) | US8318695B2 (ja) |
EP (1) | EP2178923A1 (ja) |
JP (2) | JP5518709B2 (ja) |
KR (1) | KR20100046038A (ja) |
CN (2) | CN101790542B (ja) |
AU (1) | AU2008282541B2 (ja) |
BR (1) | BRPI0815045A2 (ja) |
CA (1) | CA2695179A1 (ja) |
HK (1) | HK1142917A1 (ja) |
MX (1) | MX2010001219A (ja) |
NZ (2) | NZ583031A (ja) |
WO (1) | WO2009018076A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014194018A (ja) * | 2007-07-30 | 2014-10-09 | Allergan Inc | 調節可能架橋ヒアルロン酸組成物 |
Families Citing this family (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2861734B1 (fr) | 2003-04-10 | 2006-04-14 | Corneal Ind | Reticulation de polysaccharides de faible et forte masse moleculaire; preparation d'hydrogels monophasiques injectables; polysaccharides et hydrogels obtenus |
US20060073208A1 (en) * | 2004-10-01 | 2006-04-06 | Allergan, Inc. | Cosmetic neurotoxin compositions and methods |
US20080293637A1 (en) * | 2007-05-23 | 2008-11-27 | Allergan, Inc. | Cross-linked collagen and uses thereof |
US20110077737A1 (en) * | 2007-07-30 | 2011-03-31 | Allergan, Inc. | Tunably Crosslinked Polysaccharide Compositions |
US20120071437A1 (en) * | 2007-07-30 | 2012-03-22 | Allergan, Inc. | Tunable crosslinked polysaccharide compositions |
US8697044B2 (en) * | 2007-10-09 | 2014-04-15 | Allergan, Inc. | Crossed-linked hyaluronic acid and collagen and uses thereof |
US8114898B2 (en) | 2007-11-16 | 2012-02-14 | Allergan, Inc. | Compositions and methods for treating purpura |
US8394784B2 (en) | 2007-11-30 | 2013-03-12 | Allergan, Inc. | Polysaccharide gel formulation having multi-stage bioactive agent delivery |
US8394782B2 (en) * | 2007-11-30 | 2013-03-12 | Allergan, Inc. | Polysaccharide gel formulation having increased longevity |
US20090143348A1 (en) * | 2007-11-30 | 2009-06-04 | Ahmet Tezel | Polysaccharide gel compositions and methods for sustained delivery of drugs |
US8450475B2 (en) | 2008-08-04 | 2013-05-28 | Allergan, Inc. | Hyaluronic acid-based gels including lidocaine |
US9228027B2 (en) | 2008-09-02 | 2016-01-05 | Allergan Holdings France S.A.S. | Threads of Hyaluronic acid and/or derivatives thereof, methods of making thereof and uses thereof |
US20100098772A1 (en) * | 2008-10-21 | 2010-04-22 | Allergan, Inc. | Drug delivery systems and methods for treating neovascularization |
JP4885245B2 (ja) * | 2009-01-15 | 2012-02-29 | 日本航空電子工業株式会社 | Rdコンバータ及び角度検出装置 |
EP2459239A1 (en) | 2009-07-30 | 2012-06-06 | Carbylan Biosurgery, Inc. | Modified hyaluronic acid polymer compositions and related methods |
NZ599583A (en) | 2009-10-29 | 2013-09-27 | Ascendis Pharma As | Sterilization of biodegradable hydrogels |
US20110171310A1 (en) * | 2010-01-13 | 2011-07-14 | Allergan Industrie, Sas | Hydrogel compositions comprising vasoconstricting and anti-hemorrhagic agents for dermatological use |
US9114188B2 (en) | 2010-01-13 | 2015-08-25 | Allergan, Industrie, S.A.S. | Stable hydrogel compositions including additives |
US20110171286A1 (en) * | 2010-01-13 | 2011-07-14 | Allergan, Inc. | Hyaluronic acid compositions for dermatological use |
US20110171311A1 (en) * | 2010-01-13 | 2011-07-14 | Allergan Industrie, Sas | Stable hydrogel compositions including additives |
US20110172180A1 (en) | 2010-01-13 | 2011-07-14 | Allergan Industrie. Sas | Heat stable hyaluronic acid compositions for dermatological use |
CA2792729C (en) * | 2010-03-12 | 2016-06-28 | Allergan Industrie, Sas | Fluid compositions for improving skin conditions |
DK3078388T3 (da) | 2010-03-22 | 2019-05-20 | Allergan Inc | Tværbundne hydrogeler til blødvævsforøgelse |
US8889123B2 (en) | 2010-08-19 | 2014-11-18 | Allergan, Inc. | Compositions and soft tissue replacement methods |
US8883139B2 (en) | 2010-08-19 | 2014-11-11 | Allergan Inc. | Compositions and soft tissue replacement methods |
US9005605B2 (en) | 2010-08-19 | 2015-04-14 | Allergan, Inc. | Compositions and soft tissue replacement methods |
US8697057B2 (en) | 2010-08-19 | 2014-04-15 | Allergan, Inc. | Compositions and soft tissue replacement methods |
CN107412002A (zh) * | 2011-06-03 | 2017-12-01 | 阿勒根公司 | 包括抗氧化剂的皮肤填充剂组合物 |
US9393263B2 (en) | 2011-06-03 | 2016-07-19 | Allergan, Inc. | Dermal filler compositions including antioxidants |
US20130096081A1 (en) | 2011-06-03 | 2013-04-18 | Allergan, Inc. | Dermal filler compositions |
US9408797B2 (en) | 2011-06-03 | 2016-08-09 | Allergan, Inc. | Dermal filler compositions for fine line treatment |
CN102226009B (zh) * | 2011-06-09 | 2013-04-10 | 西安力邦制药有限公司 | 一种交联透明质酸凝胶的制备方法 |
US9662422B2 (en) | 2011-09-06 | 2017-05-30 | Allergan, Inc. | Crosslinked hyaluronic acid-collagen gels for improving tissue graft viability and soft tissue augmentation |
US20130244943A1 (en) | 2011-09-06 | 2013-09-19 | Allergan, Inc. | Hyaluronic acid-collagen matrices for dermal filling and volumizing applications |
TWI561535B (en) * | 2011-10-06 | 2016-12-11 | Bvw Holding Ag | Copolymers of hydrophobic and hydrophilic segments that reduce protein adsorption |
MX354947B (es) | 2012-06-15 | 2018-03-27 | Merz Pharma Gmbh & Co Kgaa | Metodo para preparar una composicion a base de acido hialuronico. |
CN102784414B (zh) * | 2012-08-02 | 2014-07-23 | 东华大学 | 一种可用于组织工程的可注射性双交联水凝胶的制备方法 |
WO2014055895A1 (en) * | 2012-10-05 | 2014-04-10 | Allergan, Inc. | Injectable device and method for sculpting, augmenting or correcting facial features such as the chin |
AU2013374192B2 (en) * | 2013-01-17 | 2018-11-08 | Damian NAQVI | Increasing muscular volume in a human using hyaluronic acid |
US20140275340A1 (en) * | 2013-03-15 | 2014-09-18 | Lake Region Manufacturing, Inc. d/b/a Lake Region Medical | Modified hyaluronate hydrophilic compositions, coatings and methods |
US20140315828A1 (en) | 2013-04-22 | 2014-10-23 | Allergan, Inc. | Cross-linked silk-hyaluronic acid compositions |
JP6056111B2 (ja) * | 2013-05-22 | 2017-01-11 | 国立研究開発法人産業技術総合研究所 | 光分解性架橋剤、光分解性ゲル、細胞培養器具、細胞配列・分別装置、細胞配列方法、細胞分別方法、組織体形成方法および組織体 |
CN109734825B (zh) * | 2013-06-28 | 2022-01-28 | 盖尔德玛公司 | 用于制造成形的交联的透明质酸产物的方法 |
CN103920182B (zh) * | 2014-04-16 | 2015-10-21 | 华熙福瑞达生物医药有限公司 | 一种生物可吸收止血膜 |
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2008
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2014194018A (ja) * | 2007-07-30 | 2014-10-09 | Allergan Inc | 調節可能架橋ヒアルロン酸組成物 |
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HK1142917A1 (en) | 2010-12-17 |
JP2010535277A (ja) | 2010-11-18 |
MX2010001219A (es) | 2010-03-01 |
NZ599888A (en) | 2013-08-30 |
EP2178923A1 (en) | 2010-04-28 |
CN102850468A (zh) | 2013-01-02 |
CA2695179A1 (en) | 2009-02-05 |
US20090036403A1 (en) | 2009-02-05 |
CN101790542A (zh) | 2010-07-28 |
JP2014194018A (ja) | 2014-10-09 |
AU2008282541B2 (en) | 2013-09-26 |
US8318695B2 (en) | 2012-11-27 |
KR20100046038A (ko) | 2010-05-04 |
WO2009018076A1 (en) | 2009-02-05 |
AU2008282541A1 (en) | 2009-02-05 |
NZ583031A (en) | 2012-05-25 |
BRPI0815045A2 (pt) | 2015-02-10 |
CN101790542B (zh) | 2014-03-12 |
US20130023658A1 (en) | 2013-01-24 |
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