JPS60130601A - ヒアルロン酸水不溶性組成物の製法 - Google Patents
ヒアルロン酸水不溶性組成物の製法Info
- Publication number
- JPS60130601A JPS60130601A JP59162779A JP16277984A JPS60130601A JP S60130601 A JPS60130601 A JP S60130601A JP 59162779 A JP59162779 A JP 59162779A JP 16277984 A JP16277984 A JP 16277984A JP S60130601 A JPS60130601 A JP S60130601A
- Authority
- JP
- Japan
- Prior art keywords
- hyaluronic acid
- carried out
- crosslinking agent
- treatment
- water
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 29
- 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 28
- 229920002674 hyaluronan Polymers 0.000 title claims description 28
- 229960003160 hyaluronic acid Drugs 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 239000003431 cross linking reagent Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 7
- 229920002873 Polyethylenimine Polymers 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 4
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 claims description 2
- 229950005308 oxymethurea Drugs 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 230000008961 swelling Effects 0.000 description 11
- 239000000499 gel Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 6
- 229920002385 Sodium hyaluronate Polymers 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229940010747 sodium hyaluronate Drugs 0.000 description 5
- 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 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 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 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- -1 polyincyanate Chemical compound 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 229960004072 thrombin Drugs 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 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 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 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 240000008574 Capsicum frutescens Species 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000002011 beta-particle spectroscopy Methods 0.000 description 1
- 239000001390 capsicum minimum Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940014041 hyaluronate Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Materials For Medical Uses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56181883A | 1983-12-15 | 1983-12-15 | |
| US561818 | 1983-12-15 | ||
| US598071 | 1984-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS60130601A true JPS60130601A (ja) | 1985-07-12 |
Family
ID=24243605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59162779A Pending JPS60130601A (ja) | 1983-12-15 | 1984-07-31 | ヒアルロン酸水不溶性組成物の製法 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS60130601A (enrdf_load_stackoverflow) |
| DE (1) | DE3434082A1 (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61164558A (ja) * | 1985-01-17 | 1986-07-25 | 生化学工業株式会社 | 医療用成形物の成形材料 |
| JPS61234864A (ja) * | 1985-03-01 | 1986-10-20 | バイオマトリクス・インコーポレイテツド | 架橋ヒアルロン酸の成形物 |
| JPS62129226A (ja) * | 1985-11-29 | 1987-06-11 | バイオマトリツクス、インコ−ポレ−テツド | 不溶性ヒアルロナン、溶解性ハイラン及びそれらの塩に基づく徐放性製剤とその製造法 |
| JPH0669481B2 (ja) * | 1984-06-08 | 1994-09-07 | カビ・フアーマシア・アー・ベー | 架橋ヒアルロン酸ゲルから成る代用硝子体液 |
| JPH0669490B2 (ja) * | 1984-07-23 | 1994-09-07 | カビ・フアーマシア・アー・ベー | 体組織間の癒着を防止するための、インプラント及びその製造方法 |
| WO1995031223A1 (fr) * | 1994-05-13 | 1995-11-23 | Kuraray Co., Ltd. | Gel polymere a usage medical |
| WO2007015579A1 (ja) | 2005-08-04 | 2007-02-08 | Teijin Limited | セルロース誘導体 |
| WO2009041627A1 (ja) | 2007-09-28 | 2009-04-02 | Shiseido Company Ltd. | 膨潤性架橋ヒアルロン酸粉末及びその製造方法 |
| US8137685B2 (en) | 2003-10-29 | 2012-03-20 | Teijin Limited | Hyaluronic acid compound, hydrogel thereof and joint treating material |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5202431A (en) * | 1985-07-08 | 1993-04-13 | Fidia, S.P.A. | Partial esters of hyaluronic acid |
| US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| IT1198449B (it) * | 1986-10-13 | 1988-12-21 | F I D I Farmaceutici Italiani | Esteri di alcoli polivalenti di acido ialuronico |
| WO2003089476A1 (en) * | 2002-04-17 | 2003-10-30 | Genzyme Corporation | Cross-linked hyaluronate compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4152170A (en) * | 1975-06-18 | 1979-05-01 | Sumitomo Chemical Company, Ltd. | Cross-linked pullulan |
| GB1515963A (en) * | 1975-07-15 | 1978-06-28 | Massachusetts Inst Technology | Crosslinked collagen-mucopolysaccharide composite materials |
-
1984
- 1984-07-31 JP JP59162779A patent/JPS60130601A/ja active Pending
- 1984-09-17 DE DE19843434082 patent/DE3434082A1/de active Granted
Non-Patent Citations (1)
| Title |
|---|
| ACTA CHEM.SCAND=1964 * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0669481B2 (ja) * | 1984-06-08 | 1994-09-07 | カビ・フアーマシア・アー・ベー | 架橋ヒアルロン酸ゲルから成る代用硝子体液 |
| JPH0669490B2 (ja) * | 1984-07-23 | 1994-09-07 | カビ・フアーマシア・アー・ベー | 体組織間の癒着を防止するための、インプラント及びその製造方法 |
| JPS61164558A (ja) * | 1985-01-17 | 1986-07-25 | 生化学工業株式会社 | 医療用成形物の成形材料 |
| JPS61234864A (ja) * | 1985-03-01 | 1986-10-20 | バイオマトリクス・インコーポレイテツド | 架橋ヒアルロン酸の成形物 |
| JPS62129226A (ja) * | 1985-11-29 | 1987-06-11 | バイオマトリツクス、インコ−ポレ−テツド | 不溶性ヒアルロナン、溶解性ハイラン及びそれらの塩に基づく徐放性製剤とその製造法 |
| US5770229A (en) * | 1994-05-13 | 1998-06-23 | Kuraray Co., Ltd. | Medical polymer gel |
| WO1995031223A1 (fr) * | 1994-05-13 | 1995-11-23 | Kuraray Co., Ltd. | Gel polymere a usage medical |
| US8137685B2 (en) | 2003-10-29 | 2012-03-20 | Teijin Limited | Hyaluronic acid compound, hydrogel thereof and joint treating material |
| WO2007015579A1 (ja) | 2005-08-04 | 2007-02-08 | Teijin Limited | セルロース誘導体 |
| US8378091B2 (en) | 2005-08-04 | 2013-02-19 | Teijin Limited | Cellulose derivative |
| WO2009041627A1 (ja) | 2007-09-28 | 2009-04-02 | Shiseido Company Ltd. | 膨潤性架橋ヒアルロン酸粉末及びその製造方法 |
| KR100990301B1 (ko) | 2007-09-28 | 2010-10-26 | 가부시키가이샤 시세이도 | 팽윤성 가교 히알루론산 분말과 그 제조 방법 |
| JPWO2009041627A1 (ja) * | 2007-09-28 | 2011-01-27 | 株式会社資生堂 | 膨潤性架橋ヒアルロン酸粉末及びその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3434082C2 (enrdf_load_stackoverflow) | 1991-02-21 |
| DE3434082A1 (de) | 1985-07-11 |
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