JP5523338B2 - エマルジョン中の架橋ヒアルロン酸 - Google Patents
エマルジョン中の架橋ヒアルロン酸 Download PDFInfo
- Publication number
- JP5523338B2 JP5523338B2 JP2010538575A JP2010538575A JP5523338B2 JP 5523338 B2 JP5523338 B2 JP 5523338B2 JP 2010538575 A JP2010538575 A JP 2010538575A JP 2010538575 A JP2010538575 A JP 2010538575A JP 5523338 B2 JP5523338 B2 JP 5523338B2
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- Prior art keywords
- acid
- care
- microbeads
- hyaluronic acid
- alcohols
- Prior art date
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- 229920002674 hyaluronan Polymers 0.000 title claims description 121
- 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 113
- 229960003160 hyaluronic acid Drugs 0.000 title claims description 110
- 239000000839 emulsion Substances 0.000 title claims description 31
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- 239000011325 microbead Substances 0.000 claims description 95
- -1 benzoic acid isostearyl ester Chemical class 0.000 claims description 78
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- 239000006185 dispersion Substances 0.000 claims description 45
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- 239000003431 cross linking reagent Substances 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000000194 fatty acid Substances 0.000 claims description 34
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 33
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 25
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
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- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 21
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- 150000004665 fatty acids Chemical class 0.000 claims description 19
- 150000001298 alcohols Chemical class 0.000 claims description 18
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 18
- 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 compound 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 claims description 16
- 229940014041 hyaluronate Drugs 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 14
- 229940008099 dimethicone Drugs 0.000 claims description 13
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 13
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 13
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 229920002385 Sodium hyaluronate Chemical class 0.000 claims description 12
- 239000012670 alkaline solution Substances 0.000 claims description 12
- 229940010747 sodium hyaluronate Drugs 0.000 claims 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 class [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 claims description 12
- 239000000654 additive Substances 0.000 claims description 11
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- 239000002562 thickening agent Substances 0.000 claims description 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
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- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- PXTQQOLKZBLYDY-UHFFFAOYSA-N bis(2-ethylhexyl) carbonate Chemical compound CCCCC(CC)COC(=O)OCC(CC)CCCC PXTQQOLKZBLYDY-UHFFFAOYSA-N 0.000 claims description 7
- 239000000872 buffer Substances 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
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- 239000006071 cream Substances 0.000 claims description 6
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- 150000005690 diesters Chemical class 0.000 claims description 6
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- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229940116351 sebacate Drugs 0.000 claims description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
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- 150000003626 triacylglycerols Chemical class 0.000 claims description 6
- 239000007762 w/o emulsion Substances 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
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- 125000003118 aryl group Chemical group 0.000 claims description 5
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- 239000008041 oiling agent Substances 0.000 claims description 5
- 239000003381 stabilizer Substances 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 5
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229920002545 silicone oil Polymers 0.000 claims description 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 4
- 239000001993 wax Substances 0.000 claims description 4
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
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- 239000010941 cobalt Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- VJVOFLWZDWLHNR-MRCUWXFGSA-N icosan-9-yl (z)-docos-13-enoate Chemical compound CCCCCCCCCCCC(CCCCCCCC)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC VJVOFLWZDWLHNR-MRCUWXFGSA-N 0.000 claims description 3
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- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 claims description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical group CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001934 cyclohexanes Chemical class 0.000 claims description 2
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- 150000001983 dialkylethers Chemical class 0.000 claims description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
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- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
- A61K8/025—Explicitly spheroidal or spherical shape
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
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| US8367117B2 (en) | 2010-05-10 | 2013-02-05 | The Research Foundation Of State University Of New York | Nanocomposite hyaluronic acid-clay based hydrogels |
| JP5911871B2 (ja) * | 2010-08-31 | 2016-04-27 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 架橋多糖ビーズおよびその生物医学的使用 |
| CN102690847A (zh) * | 2012-04-13 | 2012-09-26 | 华熙福瑞达生物医药有限公司 | 酶切法制备寡聚透明质酸盐的方法及所得寡聚透明质酸盐和其应用 |
| JP2016506909A (ja) * | 2013-01-11 | 2016-03-07 | カービラン セラピューティクス, インコーポレイテッド | ヒアルロン酸を含む安定化組成物 |
| KR101272792B1 (ko) | 2013-03-04 | 2013-06-10 | 주식회사 뉴앤뉴 | 보습성이 우수한 수분크림 |
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2008
- 2008-12-10 EP EP08861569.5A patent/EP2222715B1/en active Active
- 2008-12-10 WO PCT/EP2008/067172 patent/WO2009077399A1/en not_active Ceased
- 2008-12-10 CN CN2008801179740A patent/CN101878230B/zh active Active
- 2008-12-10 JP JP2010538575A patent/JP5523338B2/ja active Active
- 2008-12-10 US US12/809,809 patent/US9109051B2/en active Active
- 2008-12-19 CN CN2008801271253A patent/CN101952325A/zh active Pending
- 2008-12-19 TW TW097149645A patent/TW200938208A/zh unknown
- 2008-12-19 EP EP08863221A patent/EP2225281A1/en not_active Withdrawn
- 2008-12-19 JP JP2010538766A patent/JP2011506734A/ja active Pending
- 2008-12-19 CA CA2709824A patent/CA2709824A1/en not_active Abandoned
- 2008-12-19 WO PCT/EP2008/068050 patent/WO2009077620A1/en not_active Ceased
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2009077620A1 (en) | 2009-06-25 |
| US9109051B2 (en) | 2015-08-18 |
| EP2222715B1 (en) | 2019-07-24 |
| CA2709824A1 (en) | 2009-06-25 |
| JP2011506719A (ja) | 2011-03-03 |
| JP2011506734A (ja) | 2011-03-03 |
| TW200938208A (en) | 2009-09-16 |
| AU2008337407B2 (en) | 2013-09-05 |
| CN101952325A (zh) | 2011-01-19 |
| US20120258155A1 (en) | 2012-10-11 |
| AU2008337407A1 (en) | 2009-06-25 |
| US20100266512A1 (en) | 2010-10-21 |
| EP2222715A1 (en) | 2010-09-01 |
| US20100311963A1 (en) | 2010-12-09 |
| EP2225281A1 (en) | 2010-09-08 |
| WO2009077399A1 (en) | 2009-06-25 |
| CN101878230B (zh) | 2012-11-21 |
| CN101878230A (zh) | 2010-11-03 |
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