NO175059B - Fremgangsmåte for fremstilling av i det vesentlige rene, partielle eller totale estere av alginsyre - Google Patents
Fremgangsmåte for fremstilling av i det vesentlige rene, partielle eller totale estere av alginsyre Download PDFInfo
- Publication number
- NO175059B NO175059B NO872716A NO872716A NO175059B NO 175059 B NO175059 B NO 175059B NO 872716 A NO872716 A NO 872716A NO 872716 A NO872716 A NO 872716A NO 175059 B NO175059 B NO 175059B
- Authority
- NO
- Norway
- Prior art keywords
- alginic acid
- esters
- salts
- groups
- salt
- Prior art date
Links
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- 239000000783 alginic acid Substances 0.000 title claims description 161
- 229960001126 alginic acid Drugs 0.000 title claims description 161
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- 150000004781 alginic acids Chemical class 0.000 title claims description 145
- 238000000034 method Methods 0.000 title claims description 67
- 238000002360 preparation method Methods 0.000 title claims description 26
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- 150000003839 salts Chemical class 0.000 claims description 78
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
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- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical class O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 6
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- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/733—Alginic acid; Salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/28—Polysaccharides or their derivatives
-
- 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
- A61L17/00—Materials for surgical sutures or for ligaturing blood vessels ; Materials for prostheses or catheters
- A61L17/06—At least partially resorbable materials
- A61L17/10—At least partially resorbable materials containing macromolecular materials
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- C08B37/0084—Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Polymers & Plastics (AREA)
- Surgery (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Birds (AREA)
- Inorganic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Vascular Medicine (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cosmetics (AREA)
- Materials For Medical Uses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Jellies, Jams, And Syrups (AREA)
- Detergent Compositions (AREA)
- General Preparation And Processing Of Foods (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT48201/86A IT1203814B (it) | 1986-06-30 | 1986-06-30 | Esteri dell'acido alginico |
Publications (4)
Publication Number | Publication Date |
---|---|
NO872716D0 NO872716D0 (no) | 1987-06-29 |
NO872716L NO872716L (no) | 1988-01-04 |
NO175059B true NO175059B (no) | 1994-05-16 |
NO175059C NO175059C (hu) | 1994-08-24 |
Family
ID=11265177
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO872716A NO175059B (no) | 1986-06-30 | 1987-06-29 | Fremgangsmåte for fremstilling av i det vesentlige rene, partielle eller totale estere av alginsyre |
Country Status (24)
Country | Link |
---|---|
US (1) | US5336668A (hu) |
EP (2) | EP0609968A3 (hu) |
JP (2) | JP2569054B2 (hu) |
CN (1) | CN1026001C (hu) |
AR (1) | AR242959A1 (hu) |
AT (1) | ATE113610T1 (hu) |
AU (2) | AU602901B2 (hu) |
CA (1) | CA1338235C (hu) |
DE (1) | DE3750710T2 (hu) |
DK (1) | DK333687A (hu) |
EG (1) | EG18197A (hu) |
FI (1) | FI872878A (hu) |
HU (1) | HU202559B (hu) |
IL (1) | IL82943A (hu) |
IN (1) | IN166549B (hu) |
IT (1) | IT1203814B (hu) |
MX (1) | MX7108A (hu) |
NO (1) | NO175059B (hu) |
NZ (1) | NZ220807A (hu) |
PH (1) | PH25729A (hu) |
PL (1) | PL157922B1 (hu) |
PT (1) | PT85200B (hu) |
YU (2) | YU46960B (hu) |
ZA (1) | ZA874520B (hu) |
Families Citing this family (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5264422A (en) * | 1986-06-30 | 1993-11-23 | Fidia S.P.A. | Esters of alginic acid with steroidal alcohols |
DK110188D0 (da) * | 1988-03-02 | 1988-03-02 | Claus Selch Larsen | High molecular weight prodrug derivatives of antiinflammatory drugs |
IT1219942B (it) * | 1988-05-13 | 1990-05-24 | Fidia Farmaceutici | Esteri polisaccaridici |
JP2627344B2 (ja) * | 1990-01-23 | 1997-07-02 | 工業技術院長 | 水溶性アルギン繊維及びその製造方法 |
US5332809A (en) * | 1991-02-11 | 1994-07-26 | Fidia S.P.A. | Partial esters of gellan |
IT1247472B (it) | 1991-05-31 | 1994-12-17 | Fidia Spa | Processo per la preparazione di microsfere contenenti componenti biologicamente attivi. |
IT1263755B (it) * | 1991-09-16 | 1996-08-29 | Fidia Spa | Uso di esteri della colina con polisaccaridi acidi come agenti antiulcera e gastroprotettivi |
EP0610441A4 (en) * | 1991-10-29 | 1996-01-10 | Clover Cons Ltd | CROSSLINKABLE POLYSACCHARIDES, POLYCATIONS AND LIPIDS CAN BE USED TO ENCODE AND DISPENSE MEDICINAL PRODUCTS. |
IT1254170B (it) * | 1991-12-18 | 1995-09-11 | Mini Ricerca Scient Tecnolog | Membrane composite per la rigenerazione guidata di tessuti |
IT1254704B (it) * | 1991-12-18 | 1995-10-09 | Mini Ricerca Scient Tecnolog | Tessuto non tessuto essenzialmente costituito da derivati dell'acido ialuronico |
US5824335A (en) * | 1991-12-18 | 1998-10-20 | Dorigatti; Franco | Non-woven fabric material comprising auto-crosslinked hyaluronic acid derivatives |
FR2699545B1 (fr) * | 1992-12-18 | 1995-01-27 | Oreal | Agent gélifiant résultant de l'association d'un chitosane et d'un alginate d'alkyle ou d'hydroxyalkyle et son utilisation dans la préparation de compositions cosmétiques et pharmaceutiques. |
IT1263394B (it) * | 1993-07-30 | 1996-08-05 | Fidia Advanced Biopolymers Srl | Composizioni farmaceutiche per uso topico a base di acido ialuronico e suoi derivati |
IT1268955B1 (it) * | 1994-03-11 | 1997-03-18 | Fidia Advanced Biopolymers Srl | Esteri attivi di polisaccaridi carbossilici |
IL114193A (en) * | 1994-06-20 | 2000-02-29 | Teva Pharma | Ophthalmic pharmaceutical compositions based on sodium alginate |
CN1141149C (zh) * | 1995-02-07 | 2004-03-10 | 菲迪亚高级生物多聚合物有限公司 | 用透明质酸、其衍生物或其它天然或半合成聚合物涂覆物体表面的方法 |
IT1281886B1 (it) * | 1995-05-22 | 1998-03-03 | Fidia Advanced Biopolymers Srl | Processo per la preparazione di idrogel ottenuti da derivati chimici dell'acido ialuronico mediante irradiazioni ultraviolette e loro |
FR2764505B1 (fr) * | 1997-06-13 | 1999-10-15 | Alain Dogliani | Nouvelles compositions cosmetiques a base de lyophilisats d'alginates alcalins et nouveaux vecteurs de penetration |
IT1294797B1 (it) | 1997-07-28 | 1999-04-15 | Fidia Advanced Biopolymers Srl | Uso dei derivati dell'acido ialuronico nella preparazione di biomateriali aventi attivita' emostatica fisica e tamponante |
FR2778081B1 (fr) * | 1998-04-29 | 2000-08-25 | Fabrice Thevenet | Implants de renfort pour sutures tissulaires |
FR2781677B1 (fr) * | 1998-07-31 | 2000-10-20 | Brothier Lab | Dispositif de traitement de plaies et procede de fabrication de ce dispositif |
AU6419899A (en) * | 1998-10-09 | 2000-05-01 | Regents Of The University Of Michigan, The | Hydrogels and water soluble polymeric carriers for drug delivery |
DE10112825A1 (de) | 2001-03-16 | 2002-10-02 | Fresenius Kabi De Gmbh | HESylierung von Wirkstoffen in wässriger Lösung |
JP3814224B2 (ja) * | 2001-04-25 | 2006-08-23 | エーザイ株式会社 | 外用組成物 |
DE10209822A1 (de) | 2002-03-06 | 2003-09-25 | Biotechnologie Ges Mittelhesse | Kopplung niedermolekularer Substanzen an ein modifiziertes Polysaccharid |
DE10209821A1 (de) | 2002-03-06 | 2003-09-25 | Biotechnologie Ges Mittelhesse | Kopplung von Proteinen an ein modifiziertes Polysaccharid |
AU2003255406B2 (en) | 2002-09-11 | 2009-09-10 | Fresenius Kabi Deutschland Gmbh | Hydroxyalkyl starch derivatives |
US7538092B2 (en) | 2002-10-08 | 2009-05-26 | Fresenius Kabi Deutschland Gmbh | Pharmaceutically active oligosaccharide conjugates |
FR2850281A1 (fr) * | 2003-01-27 | 2004-07-30 | Brothier Lab | Procede de fabrication d'un dispositif de renfort de suture |
US7008476B2 (en) | 2003-06-11 | 2006-03-07 | Az Electronic Materials Usa Corp. | Modified alginic acid of alginic acid derivatives and thermosetting anti-reflective compositions thereof |
WO2005014655A2 (en) | 2003-08-08 | 2005-02-17 | Fresenius Kabi Deutschland Gmbh | Conjugates of hydroxyalkyl starch and a protein |
GB2404920A (en) * | 2003-08-12 | 2005-02-16 | Johnson & Johnson Medical Ltd | Antimicrobial polymer |
JP2007507489A (ja) * | 2003-09-30 | 2007-03-29 | ソルベスト リミテッド | 水可溶性ナノ粒子封入複合体 |
CN1946742A (zh) | 2004-03-11 | 2007-04-11 | 弗雷泽纽斯卡比德国有限公司 | 通过还原氨基化制备的羟烷基淀粉和蛋白质的偶联物 |
AR048709A1 (es) * | 2004-04-26 | 2006-05-17 | Cp Kelco Aps | Composicion dermoprotectora para controlar la alcalinidad y uso de la misma |
DE102004025495A1 (de) | 2004-05-21 | 2005-12-15 | Dr. Suwelack Skin & Health Care Ag | Verfahren zur Herstellung von Alginat-haltigen porösen Formkörpern |
GB0513552D0 (en) | 2005-07-01 | 2005-08-10 | Bristol Myers Squibb Co | Bandage |
DE102005049833A1 (de) * | 2005-10-14 | 2007-04-19 | Beiersdorf Ag | Hydrophob modifizierte Alginate |
EP2070950A1 (en) | 2007-12-14 | 2009-06-17 | Fresenius Kabi Deutschland GmbH | Hydroxyalkyl starch derivatives and process for their preparation |
US8426382B2 (en) | 2008-10-06 | 2013-04-23 | Adocia | Polysaccharides comprising carboxyl functional groups substituted by a hydrophobic alcohol derivative |
FR2936800B1 (fr) * | 2008-10-06 | 2010-12-31 | Adocia | Polysaccharide comportant des groupes fonctionnels carboxyles substitues par un derive d'alcool hydrophobe |
JP2010106068A (ja) * | 2008-10-28 | 2010-05-13 | Mie Prefecture | 多糖類の新規化学修飾法 |
WO2010069519A1 (en) * | 2008-12-18 | 2010-06-24 | Merz Pharma Gmbh & Co. Kgaa | Topical compositions comprising at least one active ingredient poorly soluble in water and biopolymers such as hyaluronic acid with a pka-value between 5-7 |
WO2012085609A1 (en) | 2010-12-20 | 2012-06-28 | Dept. Of Pathobiology | Treatment of osteoarthritis by continuous intra-articular injection of alginate gel |
ES2912545T3 (es) | 2011-06-02 | 2022-05-26 | Massachusetts Inst Technology | Alginatos modificados para la encapsulación de células y terapia celular |
DE102012208321A1 (de) | 2012-05-18 | 2013-11-21 | Robert Bosch Gmbh | Alginate als Binder für Batterie-Kathoden |
WO2015177081A1 (en) | 2014-05-19 | 2015-11-26 | Basf Se | Process for producing porous alginate-based aerogels |
CA2956075C (en) | 2014-08-01 | 2020-03-10 | Massachusetts Institute Of Technology | Modified alginates for anti-fibrotic materials and applications |
MX2018005420A (es) | 2015-11-01 | 2018-06-06 | Massachusetts Inst Technology | Alginatos modificados para materiales anti-fibroticos y aplicaciones. |
CN109563199A (zh) | 2016-06-13 | 2019-04-02 | 麻省理工学院 | 用于减少异物反应和纤维化的生物相容性两性离子聚合物涂层和水凝胶 |
US11318231B2 (en) | 2017-11-06 | 2022-05-03 | Massachusetts Institute Of Technology | Anti-inflammatory coatings to improve biocompatibility of neurological implants |
BR112020020601A2 (pt) | 2018-04-09 | 2021-01-12 | Basf Se | Composição cosmética e/ou dermatológica, e, uso cosmético da composição. |
CN109646705B (zh) * | 2019-01-30 | 2022-06-14 | 深圳齐康医疗器械有限公司 | 复合海绵及其制备方法和负压引流敷料、装置与医疗设备 |
CN110946712B (zh) * | 2019-12-31 | 2021-06-18 | 露乐健康科技股份有限公司 | 具有柔臀健脂护理功能的纸尿裤 |
CN111518226A (zh) * | 2020-03-06 | 2020-08-11 | 沈阳科技学院 | 一种用于活性染料直接印花的印花糊料的制备方法 |
CN113208953A (zh) * | 2021-04-16 | 2021-08-06 | 青岛海之林生物科技开发有限公司 | 一种海藻染发膏及其制备工艺 |
CN115850533B (zh) * | 2022-09-28 | 2023-07-21 | 青岛格诚经纬生物科技有限公司 | 一种海藻酸材料及其制备方法、应用 |
Family Cites Families (68)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA499026A (en) * | 1954-01-05 | B. Steiner Arnold | Alkylene glycol esters of alginic acid | |
US2158487A (en) * | 1935-10-22 | 1939-05-16 | Kelco Co | Triethanolamine alginate product and process |
US2426125A (en) * | 1944-04-03 | 1947-08-19 | Kelco Co | Manufacture of glycol alginates |
US2477861A (en) * | 1945-11-28 | 1949-08-02 | Donald E Clark | Production of fibrous watersoluble alginates |
US2494912A (en) * | 1947-01-20 | 1950-01-17 | Kelco Co | Higher alkylene glycol esters of alginic acid |
US2478988A (en) * | 1947-03-05 | 1949-08-16 | Walierstein Company Inc | Process for improving the foam of fermented malt beverages and product obtained thereby |
US2463824A (en) * | 1947-08-02 | 1949-03-08 | Kelco Co | Substituted alkylene glycol esters of alginic acid |
US2647035A (en) * | 1951-06-30 | 1953-07-28 | Celanese Corp | Dyeing of textile materials using alkylamine alginate thickeners |
US2694058A (en) * | 1951-10-20 | 1954-11-09 | Hoffmann La Roche | Production of polyuronic acid derivatives |
US3108042A (en) * | 1952-04-07 | 1963-10-22 | Lilly Co Eli | Corticotropin reaction complexes |
GB768309A (en) * | 1954-03-27 | 1957-02-13 | Henkel & Cie Gmbh | Process for the production of amides of alginic acid |
US2860130A (en) * | 1954-11-01 | 1958-11-11 | Kelco Co | Methyl alginate |
GB833946A (en) * | 1957-03-08 | 1960-05-04 | Nordson Pharmaceutical Lab Inc | L-amphetamine alginate |
US3115488A (en) * | 1960-02-29 | 1963-12-24 | American Home Prod | Alginic acid methyl ester sulfates, preparation and molecular weight fractionation thereof |
US3115458A (en) * | 1960-05-11 | 1963-12-24 | Michael J Bebech | Apparatus for filtering liquids |
GB976301A (en) * | 1960-10-27 | 1964-11-25 | Calmic Ltd | Preparation and use of alginates |
NL273693A (hu) * | 1961-01-18 | |||
US3787389A (en) * | 1961-04-24 | 1974-01-22 | Purdue Frederick Co | Pyrazolidone derivatives |
US3790558A (en) * | 1961-04-24 | 1974-02-05 | Purdue Frederick Co | Pyrazolidone derivatives substituted on the 4 position with pectin or algin |
US3332933A (en) * | 1964-02-21 | 1967-07-25 | Kelco Co | Diacyl n-alkyl ammonium alginates and their preparation |
US3325472A (en) * | 1964-06-18 | 1967-06-13 | Mortimer D Sackler | Polycyclohexose-polyoxyethyleneglycol suppository bases |
US3450814A (en) * | 1964-07-15 | 1969-06-17 | Chemway Corp | Ophthalmic compositions containing alginic acid salts of pilocarpine,atropine and physostigmine |
US3351581A (en) * | 1966-06-24 | 1967-11-07 | Kelco Co | Acetyl alginates and pectates and process of making the same |
GB1174854A (en) * | 1967-07-07 | 1969-12-17 | Miles Lab | New Biologically Active Conjugates |
US4003792A (en) * | 1967-07-01 | 1977-01-18 | Miles Laboratories, Inc. | Conjugates of acid polysaccharides and complex organic substances |
US3535308A (en) * | 1968-01-15 | 1970-10-20 | American Cyanamid Co | Process for the preparation of partially esterified polyhydroxylic polymers |
US3574641A (en) * | 1968-03-29 | 1971-04-13 | Kelco Co | High neutralized propylene glycol alginate in french dressing |
US3967618A (en) * | 1969-04-01 | 1976-07-06 | Alza Corporation | Drug delivery device |
US3993073A (en) * | 1969-04-01 | 1976-11-23 | Alza Corporation | Novel drug delivery device |
DK125598B (da) * | 1969-09-29 | 1973-03-12 | Grindstedvaerket As | Fremgangsmåde til fremstilling af propylenglykolalginat. |
US3792164A (en) * | 1970-03-31 | 1974-02-12 | Chemway Corp | Ophthalmic composition comprising water-soluble alkaloid salts of polyuronic acids |
DE2148279A1 (de) * | 1970-09-30 | 1972-04-06 | Unilever N V , Rotterdam (Nieder lande) | Geruststoffe fur Detergensmittel |
US3887175A (en) * | 1970-11-19 | 1975-06-03 | G A Cochard Lab | Quinidine alginate and process of preparation thereof |
CA942744A (en) * | 1970-12-11 | 1974-02-26 | David J. Pettitt | Method for preparing propylene glycol esters of alginic acid |
GB1375572A (hu) * | 1971-08-12 | 1974-11-27 | ||
GB1395898A (en) * | 1971-09-28 | 1975-05-29 | Berenguer Beneyto Lab | Dihydroquinidine derivative |
US4024073A (en) * | 1972-01-08 | 1977-05-17 | Toray Industries, Inc. | Hydrogel and production thereof |
US4206301A (en) * | 1972-09-28 | 1980-06-03 | Seymour Yolles | Sustained flavor release composition |
US3772266A (en) * | 1972-10-19 | 1973-11-13 | Kelco Co | Process for the preparation of propylene glycol alginate from partially neutralized alginic acid |
US4178361A (en) * | 1973-09-10 | 1979-12-11 | Union Corporation | Sustained release pharmaceutical composition |
FR2247204A1 (en) * | 1973-10-16 | 1975-05-09 | Girardiere Gf | Veterinary aerosol foams - contg alginic acid derivs as film-formers for injection into cows teats, vagina or uterus |
US3946110A (en) * | 1974-05-30 | 1976-03-23 | Peter, Strong Research And Development Company, Inc. | Medicinal compositions and methods of preparing the same |
US4002731A (en) * | 1974-06-17 | 1977-01-11 | Sterling Drug Inc. | Diagnostic process using sodium tyropanoate |
CA1019326A (en) * | 1974-07-16 | 1977-10-18 | Uniroyal Ltd. | Process for the production of alkylene glycol alginates |
US4013820A (en) * | 1974-11-07 | 1977-03-22 | Abbott Laboratories | Universally useable tableting ingredients |
CA1057746A (en) * | 1975-09-16 | 1979-07-03 | Merck And Co. | Propylene glycol alginic acid esters |
US4104460A (en) * | 1976-09-14 | 1978-08-01 | Nobuyasu Hasebe | Method for treating seaweed with hydrogen peroxide or hydrogen peroxide compound |
AT358147B (de) * | 1976-12-03 | 1980-08-25 | Gergely Gerhard | Reinigungsmaterial |
FR2418821A1 (fr) * | 1978-03-03 | 1979-09-28 | Adeline Andre | Procede de fabrication de fibres d'alginate de calcium |
US4330338A (en) * | 1978-10-02 | 1982-05-18 | Purdue Research Foundation | Pharmaceutical coating composition, and preparation and dosages so coated |
US4364929A (en) * | 1979-04-02 | 1982-12-21 | The Purdue Frederick Company | Germicidal colloidal lubricating gels and method of producing the same |
JPS5953951B2 (ja) * | 1979-04-02 | 1984-12-27 | 住友化学工業株式会社 | 繊維材料の浸染法 |
SE442705B (sv) * | 1979-05-08 | 1986-01-27 | Viktor Kare Larsson | Medel for bildande av ett skyddsskikt pa ett underlag i form av hud eller slemhinna samt forfarande for att bilda ett skyddsskikt pa huden i icke-terapeutiskt syfte med hjelp av detta medel |
FR2482603A1 (fr) * | 1980-05-14 | 1981-11-20 | Pharmindustrie | Nouveaux esters d'heparine utilisables pour la preparation de medicaments, et procedes pour leur preparation |
JPS58206751A (ja) * | 1982-05-26 | 1983-12-02 | 日石三菱株式会社 | 創傷被覆材 |
US4512987A (en) * | 1982-07-15 | 1985-04-23 | Ciba-Geigy Corporation | New pharmaceutical preparations |
US4500676A (en) * | 1983-12-15 | 1985-02-19 | Biomatrix, Inc. | Hyaluronate modified polymeric articles |
JPS60226832A (ja) * | 1984-04-02 | 1985-11-12 | Daicel Chem Ind Ltd | 多糖の脂肪族エステルを含む分離剤 |
JPH0680081B2 (ja) * | 1984-04-11 | 1994-10-12 | ダイセル化学工業株式会社 | 多糖類誘導体 |
JPH0699482B2 (ja) * | 1984-04-16 | 1994-12-07 | ダイセル化学工業株式会社 | 多糖類誘導体 |
JPS6130516A (ja) * | 1984-07-20 | 1986-02-12 | Nichiban Co Ltd | 粘膜付着製剤 |
EP0187703B1 (en) * | 1985-01-11 | 1992-08-05 | Teijin Limited | Sustained release preparation |
US4818751A (en) * | 1985-07-02 | 1989-04-04 | Zeria Shinyaku Kogyo Kabushiki Kaisha | Cosmetics |
US4851521A (en) * | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
GB8519416D0 (en) * | 1985-08-01 | 1985-09-04 | Unilever Plc | Oligosaccharides |
SE452469B (sv) * | 1986-06-18 | 1987-11-30 | Pharmacia Ab | Material bestaende av en tverbunden karboxylgrupphaltig polysackarid och forfarande vid framstellning av detsamma |
US5147861A (en) * | 1986-06-30 | 1992-09-15 | Fidia S.P.A. | Esters of alginic acid |
US4808707A (en) * | 1987-06-08 | 1989-02-28 | University Of Delaware | Chitosan alginate capsules |
-
1986
- 1986-06-30 IT IT48201/86A patent/IT1203814B/it active
-
1987
- 1987-06-22 IL IL8294387A patent/IL82943A/en not_active IP Right Cessation
- 1987-06-22 IN IN485/CAL/87A patent/IN166549B/en unknown
- 1987-06-23 NZ NZ220807A patent/NZ220807A/en unknown
- 1987-06-23 ZA ZA874520A patent/ZA874520B/xx unknown
- 1987-06-24 CA CA000540467A patent/CA1338235C/en not_active Expired - Fee Related
- 1987-06-25 DE DE3750710T patent/DE3750710T2/de not_active Expired - Fee Related
- 1987-06-25 EP EP94201124A patent/EP0609968A3/en not_active Withdrawn
- 1987-06-25 AT AT87401464T patent/ATE113610T1/de not_active IP Right Cessation
- 1987-06-25 EP EP87401464A patent/EP0251905B1/en not_active Expired - Lifetime
- 1987-06-26 PH PH35463A patent/PH25729A/en unknown
- 1987-06-28 EG EG376/87A patent/EG18197A/xx active
- 1987-06-29 AU AU74909/87A patent/AU602901B2/en not_active Ceased
- 1987-06-29 PT PT85200A patent/PT85200B/pt not_active IP Right Cessation
- 1987-06-29 NO NO872716A patent/NO175059B/no unknown
- 1987-06-29 AR AR87307997A patent/AR242959A1/es active
- 1987-06-29 MX MX710887A patent/MX7108A/es unknown
- 1987-06-29 DK DK333687A patent/DK333687A/da not_active Application Discontinuation
- 1987-06-29 CN CN87104499A patent/CN1026001C/zh not_active Expired - Fee Related
- 1987-06-30 YU YU122087A patent/YU46960B/sh unknown
- 1987-06-30 PL PL1987266544A patent/PL157922B1/pl unknown
- 1987-06-30 HU HU872974A patent/HU202559B/hu not_active IP Right Cessation
- 1987-06-30 JP JP62165132A patent/JP2569054B2/ja not_active Expired - Lifetime
- 1987-06-30 FI FI872878A patent/FI872878A/fi not_active Application Discontinuation
-
1988
- 1988-04-26 YU YU84688A patent/YU46980B/sh unknown
-
1991
- 1991-01-30 AU AU70084/91A patent/AU651804B2/en not_active Ceased
- 1991-06-20 US US07/722,398 patent/US5336668A/en not_active Expired - Fee Related
-
1996
- 1996-01-25 JP JP8010859A patent/JPH08311104A/ja active Pending
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