EP1144458A1 - Substance for reduction of cholesterol as well as lipids content - Google Patents
Substance for reduction of cholesterol as well as lipids contentInfo
- Publication number
- EP1144458A1 EP1144458A1 EP99954018A EP99954018A EP1144458A1 EP 1144458 A1 EP1144458 A1 EP 1144458A1 EP 99954018 A EP99954018 A EP 99954018A EP 99954018 A EP99954018 A EP 99954018A EP 1144458 A1 EP1144458 A1 EP 1144458A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- substance
- microcrystalline chitosan
- cholesterol
- reduction
- lipids
- 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- Withdrawn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
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 title claims abstract description 61
- 235000012000 cholesterol Nutrition 0.000 title claims abstract description 28
- 150000002632 lipids Chemical class 0.000 title claims abstract description 27
- 239000000126 substance Substances 0.000 title claims abstract description 21
- 229920001661 Chitosan Polymers 0.000 claims abstract description 52
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims abstract description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 12
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 230000002195 synergetic effect Effects 0.000 claims abstract description 9
- 239000006185 dispersion Substances 0.000 claims abstract description 8
- 239000013543 active substance Substances 0.000 claims abstract description 7
- 229910000019 calcium carbonate Inorganic materials 0.000 claims abstract description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims abstract description 6
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims abstract description 6
- 239000001095 magnesium carbonate Substances 0.000 claims abstract description 6
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims abstract description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 6
- 229960005070 ascorbic acid Drugs 0.000 claims abstract description 5
- 235000010323 ascorbic acid Nutrition 0.000 claims abstract description 5
- 239000011668 ascorbic acid Substances 0.000 claims abstract description 5
- 229940093915 gynecological organic acid Drugs 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 235000005985 organic acids Nutrition 0.000 claims abstract description 4
- 239000007787 solid Substances 0.000 claims abstract 2
- 239000002775 capsule Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 239000006187 pill Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000000902 placebo Substances 0.000 description 9
- 229940068196 placebo Drugs 0.000 description 9
- 230000006196 deacetylation Effects 0.000 description 7
- 238000003381 deacetylation reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 235000019155 vitamin A Nutrition 0.000 description 5
- 239000011719 vitamin A Substances 0.000 description 5
- 235000019165 vitamin E Nutrition 0.000 description 5
- 239000011709 vitamin E Substances 0.000 description 5
- 108010007622 LDL Lipoproteins Proteins 0.000 description 4
- 102000007330 LDL Lipoproteins Human genes 0.000 description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000008214 LDL Cholesterol Methods 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000012747 synergistic agent Substances 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 229940045997 vitamin a Drugs 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 101001005200 Drosophila melanogaster Protein limb expression 1 homolog Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- -1 cholesterol triglycerides Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 235000002535 fat free diet Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 235000015263 low fat diet Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/722—Chitin, chitosan
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
- A61K33/10—Carbonates; Bicarbonates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the invention relates to a substance for reduction of serum cholesterol as well as lipids content in mammals, especially humans.
- US-patent 4223023 discloses the use of standard chitosan as a food additive and an orally administrable preparation to reduce the absorption of lipids.
- microcrystalline chitosan in a form of gel-like dispersion and/or powder characterized by average molecular weight higher than 1 ,000 daltons, preferably 10,000 to 300,000 daltons for reducing cholesterol and higher than 10,000 daltons, preferably 50,000 to 700,000 daltons for reducing lipids, and the deacetylation degree higher than 60 % is described in WO 98/34625.
- This publication describes the general activity of microcrystalline chitosan for reduction of content of cholesterol and lipids.
- the object of this invention is to effectively, specially and selectively reduce cholesterol as well as lipids content using microcrystalline chitosan.
- the substance, in a suitable form to be administered orally is mainly characterized by two fractions of microcrystalline chitosan differing in average molecular weights. These fractions are present simultaneously in the same product which has been prepared by blending the two fractions, each having a characteristic molecular weight distribution and average value of its own.
- the fraction with lower average molecular weight is responsible for the reduction of cholesterol level, especially the harmful LDL cholesterol, and the fraction with higher average molecular weight incorporated in the same formulation is responsible for the reduction of lipids. It is also possible that the fractions differ in other properties as well.
- the microcrystalline chitosan in the product is combined with synergistic active substances to increase the cholesterol and lipids reduction.
- microcrystalline chitosan present in at least two fractions is in a form of powder and/or gel-like dispersion and it is combined with synergistic active substances such as organic acids like ascorbic acid and/or carbonates like sodium carbonate, calcium carbonate and/or magnesium carbonate to improve the efficiency of substance in the body and to increase the cholesterol and lipids reduction.
- synergistic active substances such as organic acids like ascorbic acid and/or carbonates like sodium carbonate, calcium carbonate and/or magnesium carbonate to improve the efficiency of substance in the body and to increase the cholesterol and lipids reduction.
- microcrystalline chitosan is combined with synergistic active substances in a weight ratio ranged from 1 :0.001 to 0.001 :1 , preferably 1 :0.01 to 0.01 :1.
- the polydispersity of the blended selected polymer fractions is lower than 4.0.
- the first fraction has average molecular weight below 140 kD, preferably ranging from 20 to 140 kD for reduction of cholesterol content.
- the second fraction has average molecular weight higher than 140 kD, preferably in the range of 160-400 kD and most preferably in the range of 200-400 kD for reduction of lipids content and is thus responsible for slimming effect.
- the weight ratio of the two microcrystalline chitosan fractions ranges from 1 :99999 to 99999:1 , preferably from 1 :4999 to 4999:1.
- the most practical embodiments have the ratios between 1:19 and 19:1 , preferably between 1 :9 and 9:1.
- microcrystalline chitosan is combined with additives characterized by high synergistic action with this natural polymeric material that is able to form complexes with cholesterol and lipids.
- the synergistic additives consisting of organic acids like ascorbic acid and/or suitable carbonates like sodium carbonate, calcium carbonate and/or magnesium carbonate in a presence of microcrystalline chitosan improve the special form of chitosan activity, protect the mammal organism system as well as protect against removal of the fat-soluble vitamins A and E.
- Microcrystalline chitosan has a highly developed intrinsic surface, high positive charge and good ability to create hydrogen and ionic bonds and can form a complex with the synergistic active substances.
- the carbonates contribute to the advantageous behaviour of the administered preparation in the gastrointestinal tract and keep the microcrystalline chitosan well dispersed in the stomach by releasing carbon dioxide upon contact with the acidic environment of the stomach. Further, by suitably choosing the balance between the various carbonates the pH of the preparation can be adjusted.
- the selectivity of the rate of microcrystalline chitosan action for reduction of cholesterol and/or lipids according to the invention is connected with its fractional content as well as polydispersity degree lower than 4.0.
- the first fraction of microcrystalline chitosan defined with viscometric average molecular weight as lying below 140 kD, preferably in a range of 20-140 kD, is subjected to faster enzymatic degradation producing suitable amount of oligoaminosaccharides with assumed structure and ability to combine at high rate with cholesterol, especially its low density fraction LDL (low density lipoprotein).
- the second fraction of microcrystalline chitosan defined with viscometric average molecular weight to lie higher than 140 kD, preferably from 160 to 400 kD and most preferably in a range of 200-400 kD, is responsible for reduction of lipids content. Suitable ratio of above fractions in the microcrystalline chitosan used makes possible the selective, specific action against cholesterol on one hand and lipids on the other hand.
- the substance according to the invention containing microcrystalline chitosan after 4 weeks of patient treatment has reduced the total cholesterol content more than 6 % and the LDL cholesterol more than 15 % in comparison to the initial levels.
- the advantage of substance containing microcrystalline chitosan is connected with its variety of possible forms from powder to gel-like dispersion. It is not necessary to use a special diet together with the substance according to the invention.
- the essential components of the substance can be included in an orally administrable unit together with a pharmaceutically accepetable carrier.
- the substance can thus be in the form of a capsule, tablet or pill.
- microcrystalline chitosan properties viscometric average molecular weight according to the method described in "Chitin”, Pergamon Press, Oxford, 1977 - deacetylation degree according to the method described in the “Cellulose Chemistry and Technology", vol. 11 , p. 633, 1977 polydispersity as well as fraction content according to the Gel Permeation Chromatography method.
- 51 healthy females with body mass index ranging from 28.0 to 34.99 were subjected to in vivo test conducted according to the Declaration of Helsinki and Tokyo with trial plan reviewed by the local ethics committee. The trial was also conducted according to the Good Clinical Practice rules. The patients were asked to maintain their daily living routines including eating habits.
- the identical capsules containing starch as placebo were used for comparison.
- the procedure produced a daily dose of 2.4 g of microcrystalline chitosan to be taken in three capsules twice a day.
- the same system was used for placebo.
- microcrystalline chitosan powder characterized by viscometric average molecular weight of 300 kD, deacetylation degree of 84.7 % and polydispersity degree of 3.42 was blended with 99.9 weight parts of fraction of microcrystalline chitosan characterized by viscometric average molecular weight of 123 kD, deacetylation degree of 84.8. % and polydispersity degree of 3.67.
- the blended microcrystalline chitosan powder was characterized by viscometric average molecular weight of 122 kD, deacetylation degree of 84,8 % and polydispersity degree of 3.65.
- Example 3 400 mg of above blend with addition of 70 mg of active synergistic agents as in Example 1 were used in a form of capsules for reduction of cholesterol and lipids content. The procedure was as in Example 1. The patient characteristics as well as results of treatment after 8 weeks are presented in Table 3.
- Vitamin A ( ⁇ M/l) before 2.44 ⁇ 0.4 2.31 ⁇ 0.3 after 2.41 ⁇ 0.3 2.29 ⁇ 0.3
- Vitamin E ( ⁇ M/l) before 24.80 ⁇ 5.4 24.00 ⁇ 3.8 after 24.60 ⁇ 5.4 24.91 ⁇ 4.1
- Raising the average molecular weight will result in still more lipids being absorbed, in the range 75 to 87 %, and the optimal range of Mw is between 200 and 400 kD.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Inorganic Chemistry (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI982291 | 1998-10-23 | ||
FI982291A FI982291A (fi) | 1998-10-23 | 1998-10-23 | Aine kolesterolin sekä lipidien pitoisuuden alentamiseksi |
PCT/FI1999/000885 WO2000024785A1 (en) | 1998-10-23 | 1999-10-25 | Substance for reduction of cholesterol as well as lipids content |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1144458A1 true EP1144458A1 (en) | 2001-10-17 |
Family
ID=8552763
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP99954018A Withdrawn EP1144458A1 (en) | 1998-10-23 | 1999-10-25 | Substance for reduction of cholesterol as well as lipids content |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP1144458A1 (fi) |
JP (1) | JP2002528571A (fi) |
CN (1) | CN1331703A (fi) |
AU (1) | AU1048600A (fi) |
CA (1) | CA2347967A1 (fi) |
FI (1) | FI982291A (fi) |
WO (1) | WO2000024785A1 (fi) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002083104A1 (en) * | 2001-04-12 | 2002-10-24 | Medicarb Ab | An effervescent solid composition of matter |
SE522529C2 (sv) * | 2001-04-12 | 2004-02-17 | Medicarb Ab | Effervescent fastämneskomposition innefattande som aktiv komponent kitosan, dess derivat och salter därav, användning samt framställning därav |
KR100473445B1 (ko) * | 2001-05-10 | 2005-03-08 | 씨제이 주식회사 | 저분자 키토산과 ε-폴리라이신을 주원료로 하는 콜레스테롤 저하제 및 건강 보조 식품 |
ES2209632B1 (es) * | 2002-08-30 | 2005-08-01 | Romildo Holding, N.V. | Complemento dietetico, soluble, efervescente y alimenticio. |
US20060058261A1 (en) * | 2004-09-15 | 2006-03-16 | Andre Aube | Chitin derivatives for hyperlipidemia |
EP1960436A1 (en) * | 2005-12-16 | 2008-08-27 | Dnp Canada Inc. | Chitin derivatives for hyperlipidemia |
EP2089037A2 (en) * | 2006-12-07 | 2009-08-19 | BEN-BAR Technology 2006 Ltd. | Mixture and method for reducing cholesterol using hydrophobic microparticles |
EP2016946B1 (en) * | 2007-07-18 | 2013-02-27 | The Jordanian Pharmaceutical Manufacturing Co. | Chitosan silicon dioxide coprecipitate composition for use as a therapeutically active agent |
CN102469782A (zh) | 2010-06-18 | 2012-05-23 | 哈洛资源公司 | 包含壳聚糖的固态共混物的制剂及方法 |
CN102504291B (zh) * | 2011-10-28 | 2014-01-01 | 北京联合大学生物化学工程学院 | pH敏感型壳聚糖交联聚维酮凝胶及其制备方法和应用 |
CN115568321B (zh) * | 2022-09-16 | 2024-04-02 | 江苏省农业科学院 | 一种延长苏翠1号梨叶片生理功能期的方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4223023A (en) * | 1978-10-12 | 1980-09-16 | Ivan Furda | Nonabsorbable lipid binder |
FI83426C (fi) * | 1989-06-30 | 1991-07-10 | Firextra Oy | Foerfarande foer kontinuerlig framstaellning av mikrokristallin kitosan. |
JPH07100040B2 (ja) * | 1992-11-24 | 1995-11-01 | 朝日食品工業株式会社 | キトサンおよび/またはその部分分解物の分子量分布測定方法 |
FI107432B (fi) * | 1997-02-06 | 2001-08-15 | Novasso Oy | Mikrokiteisen kitosaanin käyttö |
-
1998
- 1998-10-23 FI FI982291A patent/FI982291A/fi unknown
-
1999
- 1999-10-25 EP EP99954018A patent/EP1144458A1/en not_active Withdrawn
- 1999-10-25 CA CA002347967A patent/CA2347967A1/en not_active Abandoned
- 1999-10-25 JP JP2000578354A patent/JP2002528571A/ja active Pending
- 1999-10-25 WO PCT/FI1999/000885 patent/WO2000024785A1/en not_active Application Discontinuation
- 1999-10-25 CN CN99814701A patent/CN1331703A/zh active Pending
- 1999-10-25 AU AU10486/00A patent/AU1048600A/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO0024785A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO2000024785A1 (en) | 2000-05-04 |
AU1048600A (en) | 2000-05-15 |
FI982291A0 (fi) | 1998-10-23 |
CA2347967A1 (en) | 2000-05-04 |
JP2002528571A (ja) | 2002-09-03 |
CN1331703A (zh) | 2002-01-16 |
FI982291A (fi) | 2000-04-24 |
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