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WO1998034625A1 - Substance aux fins de la reduction de teneurs en lipides et en cholesterol et technique afferente - Google Patents

Substance aux fins de la reduction de teneurs en lipides et en cholesterol et technique afferente Download PDF

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Publication number
WO1998034625A1
WO1998034625A1 PCT/FI1998/000106 FI9800106W WO9834625A1 WO 1998034625 A1 WO1998034625 A1 WO 1998034625A1 FI 9800106 W FI9800106 W FI 9800106W WO 9834625 A1 WO9834625 A1 WO 9834625A1
Authority
WO
WIPO (PCT)
Prior art keywords
chitosan
substance
microcrystalline chitosan
microcrystalline
gel
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.)
Ceased
Application number
PCT/FI1998/000106
Other languages
English (en)
Inventor
Henryk Struszczyk
Elina MÄKINEN
Olli KIVEKÄS
Harri HÄKLI
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novasso Oy
Original Assignee
Novasso Oy
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Novasso Oy filed Critical Novasso Oy
Priority to AU59890/98A priority Critical patent/AU5989098A/en
Priority to CA002280507A priority patent/CA2280507A1/fr
Priority to EP98903026A priority patent/EP1014997A1/fr
Priority to JP53381898A priority patent/JP2001512432A/ja
Publication of WO1998034625A1 publication Critical patent/WO1998034625A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • A61K31/716—Glucans
    • A61K31/722—Chitin, chitosan
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the invention relates to a substance and method for reduction of lipids by reducing their absorption in a living body.
  • the invention also includes a substance and method for reduction of serum cholesterol content.
  • the negative effects of lipids in many biological processes are described inter alia in: Laboratory Investigation; vol. 39, pages 574 — 583, 1978, Biochimica Biophysica Acta, vol. 515, pages 163 — 205, 1978 and International Journal of Pharmacy, vol. 74, pages 137 — 146, 1991.
  • the subsequent digestion and absorption of lipids affects negatively the weight control as well as causes health problems.
  • Cholesterol classified in lipid classification among precursor and derived lipids, an essential component of cell membranes and a precursor for steroid hormone synthesis, and triglycerides, an important energy source, are transported as lipoproteins in the blood.
  • Hyperlipopro- teinemias are disturbances of lipid transport that result from accelerated synthesis or retarded degradation of lipoproteins. This abnormal phenomenon known as hyperlipidemia is detected by finding an elevated concentration of cholesterol and triglycerides in serum. High contents of serum lipoproteins are clinically very important, because they may cause two life-threatening problems: atherosclerosis and pan- creatitis. Suitable reduction of the cholesterol-carrying lipoproteins, through diet and drugs, decreases a risk of myocardial infarction in subjects of hyperlipoproteinemia and hyperlipidemia.
  • a dietary therapy has failed to reduce the serum lipid concentration as well as in the case of hereditary hyperlipidemia and hyperlipoproteinemia, the use of lipid-lowering substances or special therapy is necessary.
  • the serum exchange technique to lower the blood lipid concentration is well known from the monograph "Topic in Plasmopho- resis", published by ISAO Press., Cleveland, 1985.
  • Another selected adsorption method by the lipid removal in blood perfusion is described in the paper Proc. Natl. Awd. Sci. Cuss., Vol. 8(110), p. 611 , 1987.
  • cholestyramine being a synthetic cationic polymer under the trade name Dowex 1 having cationing tertiary amino groups for clinical use as a hypocholesterolemic drug
  • Dowex 1 having cationing tertiary amino groups for clinical use as a hypocholesterolemic drug
  • Initial chitosan (1 ,4-linked- ⁇ -D-glucosamine) — a standard material obtained through deacetylation of chitin — has a lipid-lowering action similar to those of cholestyramine but without any toxic effects. This an- tihypercholesterolemic and antihyperlipidemic action is a result of the inhibition of fat digestion by initial chitosan.
  • the hypocholesterolemic activity of initial chitosan by oral administration has been found in rats and it is described in Nutr. Rep. Int., Vol. 18, p. 531 , 1978; Vol. 19, p. 327, 1979; Vol 20, p. 677, 1979; and Am. J. Clin. Nutr., Vol.
  • Hypocholesterolemic quaternary ammonium salts of initial chitosan are also described in WO 92/06136.
  • Initial chitosan binds the fatty acids to form the corresponding complex salts by natural ionic bonds. After ingestion, the resulting salts bind additional lipids, due to hydrophobic interaction of triglycerides, fatty and bile acids, cholesterol and other sterols.
  • Hydrochloric acid in the stomach does not hydrolyse chitosan-fatty acid salts, because this material hardly wets. The material grows in size during its transportation through the gastrointestinal tract and binds additional amounts of lipids.
  • the chitosan when ingested, promotes the binding and ex- cretion of fatty materials including cholesterol, sterols and triglycerides. This process is described in US Patent 4,223,023 and in J. Nutr. Sci. Vitaminol., Vol. 38, p. 609, 1992.
  • the studies of dietary action of initial chitosan applied in the diet in the amount of 3 to 6 g per day showed that the serum total cholesterol level significantly decreased. These studies are described in Biosc. Biotechn. Biochem., Vol. 57(9), p. 1439, 1993.
  • the well-known anticholesterolically acting initial chitosan is, however, characterized by several disadvantages, such as insufficient effectivity to reduce the cholesterol level, especially in a long-term treatment, too high dimension of particles of initial chitosan used, as a result of the nature of form of this polymer, non-direct tableting behaviour as well as the usefulness of the form of initial chitosan in general.
  • Microcrystalline chitosan as a most useful form of chitosan with high developed intrinsic surface, controlled biodegradability and bioactivity, and high sorption capacity being much higher than with initial chitosan, is well known from Finnish Patent 83426 and the corresponding International Application, publication No. WO 91/00298; Journal of Applied Polymer Science, Vol. 33, p. 177, 1987; British Polymer Journal, Vol. 23, p. 261 , 1990; Advances in Chitin Science, Vol. 1 , p. 482, J. Andre Publ., Lyon, 1996.
  • the object of this invention is to effectively reduce the lipids absorption in mammals, especially humans.
  • the object is attained by using microcrystalline chitosan in a form of microcrystalline powder and/or gel-like dispersion, orally administered in an amount suitable for effective re- duction of the absorption of lipids.
  • the substance for the reduction of lipids absorption in mammals comprises microcrystalline chitosan.
  • the microcrystalline chitosan can be in the form of a powder with an aver- age particle dimension lower than 100 ⁇ m and/or a gel-like dispersion with an average particle dimension lower than 100 ⁇ m.
  • the material is especially characterized by average molecular weight higher than 10.000 daltons, preferably 50.000 to 700.000 daltons and deacetylation degree higher than 60 %, preferably 70 to 95 %.
  • the microcrystalline chitosan powder as a component in the substance for lipids reduction, formed preferably by air-spray drying is characterized by water retention value of WRV not lower than 150 %, preferably 200 to 300 %, with high direct tabletting ability.
  • the microcrystalline chitosan powder as a component in the substance for lipids reduction, formed by lyophilization is characterized by water retention value not lower than 200 %, preferably 250 to 400 %.
  • the microcrystalline chitosan gel-like dispersion as a component in the substance for lipids reduction containing more than 0.1 wt-% of microcrystalline polymer, preferably 1 to 4 wt-%, is characterized by water retention value not lower than 500 %, preferably 800 to 5000 %.
  • the object of this invention is also to effectively reduce the serum cholesterol level in mammals, especially humans.
  • the object is attained by using microcrystalline chitosan with specified properties in the form of a gel-like dispersion and/or powder, orally administered in an amount suitable to give an effective reduction of the serum cholesterol content.
  • the substance for the reduction of serum cholesterol content in mammals by chitosan comprises microcrystalline chitosan.
  • the microcrystalline chitosan can be in the form of a powder with an average particle dimension lower than 80 ⁇ m and/or a gel-like dispersion with an average particle dimension lower than 200 ⁇ m.
  • the material is especially distinguished by average viscometric molecular weight higher than 1000 daltons, preferably 10,000 to 300,000 daltons, and a deacetylation degree in the range of 60 to 99 %, preferably 80 to 95 %.
  • the microcrystalline chitosan powder as a component in the substance for serum cholesterol level reduction is distinguished by a water retention value not lower than 100 %, preferably 150 to 250 %.
  • the microcrystalline chitosan gel-like dispersion as a component in the substance for serum cholesterol level reduction containing more than 0.5 wt-% of mi- crocrystalline polymer, preferably 1 to 3 wt-%, is distinguished by a water retention value not lower than 300 %, preferably 500 to 2000 %.
  • the microcrystalline chitosan is administered orally in the form of a gel-like dispersion and/or powder and/or tablets and/or capsules, together with and/or independently of food, or as the additives of food.
  • microcrystalline chitosan as the lipid and cholesterol binder is concerned with its ability to exist in a form of powder or/and gel-like dispersion, characterized by a very small average particle size which is not higher than 100 ⁇ m, preferably not higher than 80 ⁇ m and usually 10 to 65 ⁇ m, which sizes are impossible to produce by mechanical grinding of initial chitosan.
  • the above size of particles has effect directly on the lipid and cholesterol binding capacity.
  • microcrystalline chitosan especially in the form of air-spray dried powder, is the only chitosan form distinguished by direct tabletting behaviour connected with the ability of the individual particles of this polymer to form hydrogen bonds.
  • Fig. 1 is a microscopic photograph of microcrystalline chitosan powder, magnification 62 times, and
  • Fig. 2 is a microscopic photograph of initial chitosan, magnification
  • Microcrystalline chitosan the agent responsible for the advantageous effects is prepared by aggregating the glucosamine macromolecules from a solution of chitosan in an acid by introducing an alkaline solution and stirring.
  • the method is known as such, and reference is made to the documents mentioned above.
  • microcrystalline chitosan characterized by high developed intrinsic surface as a serum cholesterol content agent applied to mammals according to the invention is concerned with its very high susceptibility to complex the cholesterol, especially low density cholesterol, as well as triglycerides.
  • the microcrystalline chitosan according to the in- vention additionally binds the lipids, such as fatty acids and bile acids.
  • the behaviour of cholesterol and triglyceride complexing by microcrystalline chitosan (Fig. 1) with properties according to the invention is extraordinarily higher than well-known initial chitosan (Fig. 2) used previously.
  • There are extraordinary properties of microcrystalline chitosan such as high developed intrinsic surface (Fig. 1), high susceptibility for compiexation of cholesterol and triglycerides, biocompatibility, high ability for ionic bonds creation and high ability for hydrogen bonds formation that are superior to well-known initial chitosan.
  • microcrystalline chitosan according to the invention is characterized at first by its susceptibility to form suitable complexes with cholesterol, other sterols and triglycerides due to its high developed intrinsic surface, covered also by bound fatty acids producing suitable salts with this microcrystalline chitosan by natural ionic bonds.
  • a higher amount of bound fatty acid salts supports also much more the complexation of cholesterol, other sterols and triglycerides, in comparison with known initial chitosan.
  • Hydrochloric acid in the stomach not hydroiysing micro- crystalline chitosan complexes with cholesterol and triglycerides as well as salts with bound fatty acid, disperses, swells and emulgates these complexes.
  • microcrystalline chitosan due to its structural and surface advantages, also binds addi- tional amounts of cholesterol, triglycerides and lipids.
  • the complexation of cholesterol, other sterols and triglycerides by microcrystalline chitosan according to the invention is much higher and faster with beneficial effectivity, in comparison with well-known initial chitosan.
  • the complexed cholesterol, other sterols and triglycerides with accompanying lipids joined with microcrystalline chitosan are excreted from the organism.
  • Microcrystalline chitosan according to the invention is characterized by selective action against two different forms of cholesterol.
  • This micro- crystalline chitosan complexes with the low density cholesterol of LDL with a high effectivity, producing a negative effect on hypercholes- terolemic and hyperlipidemic phenomena, and often slightly increasing the high density cholesterol of HDL, having a positive action for a living organism, such as a human.
  • Microcrystalline chitosan used according to the method of invention is characterized by a special range of average molecular weight with highest effectivity for complexation of cholesterol, other sterols and triglycerides.
  • the average molecular weight of microcrystalline chitosan useful for reduction of serum cholesterol content is much lower than for binding of lipid and it is not lower than 1000 daltons, especially in the range of 10,000 to 300,000 daltons with deacetylation degree in the range of 60 to 99 %, especially 80 to 95 %.
  • microcrystalline chitosan according to the invention is continuous reduction of serum cholesterol content and stability of this process, in contrast to the initial chitosan where this phe- nomenon is not stable and usually is characterized by increase during its application.
  • microcrystalline chitosan use according to the invention is connected with variety of its possible forms from gel-like dispersion to powder. No special diet is necessary to be used together with microcrystalline chitosan.
  • binding capacity for chitosan and microcrystalline chitosan according to the modified method described in the Carbohydrate Polymers, v. 22, p. 117, 1993.
  • the binding capacity in percentage was calculated as the ratio of amount of fatty acid salt in the form of sodium undecylenic bound by chitosan to the total amount of this salt used for testing.
  • the content of total serum cholesterol and HDL cholesterol as well as triglyceride in humans and rabbits were determined according to the standards.
  • the capsules containing 0.383 g obtained microcrystalline chitosan powder were used for clinical tests in vivo.
  • a daily dose for the group of overweight persons with a weight ranged from 80 to 120 kg was 8 capsules with a total amount of microcrystalline chitosan of 3.064 g. No special diet was used for the testing persons. During 2 weeks of test, the persons were slimmed approximately 2 kg down.
  • Microcrystalline chitosan gel-like dispersion with properties described in Example 1 was used for binding the fatty acids.
  • the binding capacity of this dispersion after 15 min of treatment was 78 %.
  • This microcrystalline chitosan powder was characterized by binding capacity of 71.8 % of sodium undecylenic after 15 min of treatment.
  • Microcrystalline chitosan gel-like dispersion with properties described in Example 3 was used for binding the fatty acids.
  • the binding capacity for sodium undecylenic was 76.6 % after 15 min of treatment.
  • This microcrystalline chitosan was characterized by binding capacity of 64.6 % after 15 minutes of treatment.
  • Microcrystalline chitosan gel-like dispersion with properties described in Example 5 was used for binding the fatty acids.
  • the binding capacity for sodium undecylenic after 15 minutes of treatment was 86.6 %.
  • Microcrystalline chitosan gel-like dispersion with properties as in Ex- ample 1 was used for binding of fatty acids.
  • the binding capacity for sodium undecylenic after 15 min. of treatment was 86.2 %.
  • Microcrystalline chitosan gel-like dispersion with properties as in Ex- ample 9 was used for binding of fatty acids.
  • the binding capacity for sodium undecylenic was 86.8 %.
  • Example 3 1.0 weight part of microcrystalline chitosan gel-like dispersion with properties as in Example 3 was homogenized for 5 min with 50 rpm with 10 weight parts of yogurt to obtain the stable dispersion having specific behaviour of non-fatty dairy product causing the slimming process.
  • Example 14 1.5 weight parts of microcrystalline chitosan gel-like dispersion with properties as in Example 3 was homogenized with 10 weight parts of low caloric butter for 30 min with 30 rpm. The stable butter with specific behaviour of low fatty butter causing reduction of introduced fatty component to the human body was obtained.
  • Example 14
  • Example 10 0.7 weight parts of microcrystalline chitosan gel-like dispersion with properties as in Example 10 was homogenized for 20 min with 150 rpm with 15 weight parts of white cheese. The stable modified white cheese with specific behaviour of low fatty dairy product causing reduction of introduced fatty component to the human body was obtained.
  • the rabbits were fed with a fat rich feed using a normal feeding frequency during 2 months of test.
  • the total content of serum cholesterol, triglycerides and HDL cholesterol was determined at the beginning of microcrystalline chitosan application and at the end of the test of 1 month after microcrystalline chitosan application.
  • the results of determinations, in percentage to initial amount, are presented in the table below.
  • the val- ues of serum total cholesterol and triglyceride content during the testing time is presented in the Tables 4 and 5 below.
  • Triglyceride content mmol/l, as a function of time in months test person 0 3 5
  • the substance causing the reduction of the absorption of lipids and/or serum cholesterol content can be formed into a suitable composition, which can be administered separately as a predetermined dose, e.g. the effective amount of microcrystalline chitosan can be combined with inert pharmaceutically acceptable carriers.
  • the substance can also be incorporated into food, especially into food products containing lipids and/or cholesterol, whereby the microcrystalline chitosan will be administered together with the food.
  • the microcrystalline chitosan can be incorporated in the composition as such or in the form of a suitable complex.
  • the substance can be administered also to the body of a non-human mammal, such as domestic animals and pets, if there is a necessity to reduce the absorption of lipids and/or serum cholesterol content in these animals. All above-mentioned ways and compositions of oral administration can be used also for this alternative.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
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  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
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Abstract

Cette substance permettant de réduire l'absorption de lipides ainsi que de diminuer le taux de cholestérol sérique chez des mammifères comprend du chitosane microcristallin. Il est possible d'administrer ce chitosane microcristallin par voie orale en l'incorporant à des denrées alimentaires ou en confectionnant des unités posologiques renfermant une quantité prédéterminée dudit chitosane microcristallin. La dimension moyenne des particules du chitosane microcristallin ne dépasse pas 100 νm.
PCT/FI1998/000106 1997-02-06 1998-02-05 Substance aux fins de la reduction de teneurs en lipides et en cholesterol et technique afferente Ceased WO1998034625A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU59890/98A AU5989098A (en) 1997-02-06 1998-02-05 Substance and method for reduction of lipids and cholesterol
CA002280507A CA2280507A1 (fr) 1997-02-06 1998-02-05 Substance aux fins de la reduction de teneurs en lipides et en cholesterol et technique afferente
EP98903026A EP1014997A1 (fr) 1997-02-06 1998-02-05 Substance aux fins de la reduction de teneurs en lipides et en cholesterol et technique afferente
JP53381898A JP2001512432A (ja) 1997-02-06 1998-02-05 脂質およびコレステロールを減少させる物質および方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI970499 1997-02-06
FI970499A FI107432B (fi) 1997-02-06 1997-02-06 Mikrokiteisen kitosaanin käyttö

Publications (1)

Publication Number Publication Date
WO1998034625A1 true WO1998034625A1 (fr) 1998-08-13

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Application Number Title Priority Date Filing Date
PCT/FI1998/000106 Ceased WO1998034625A1 (fr) 1997-02-06 1998-02-05 Substance aux fins de la reduction de teneurs en lipides et en cholesterol et technique afferente

Country Status (6)

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EP (1) EP1014997A1 (fr)
JP (1) JP2001512432A (fr)
AU (1) AU5989098A (fr)
CA (1) CA2280507A1 (fr)
FI (1) FI107432B (fr)
WO (1) WO1998034625A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999036075A1 (fr) * 1998-01-17 1999-07-22 West Pharmaceutical Services Drug Delivery & Clinical Research Centre Limited Composition orale absorbant l'huile
WO2000024785A1 (fr) * 1998-10-23 2000-05-04 Novasso Oy Substance utilisee pour la reduction du taux de cholesterol et de lipides
KR20010085047A (ko) * 2001-07-25 2001-09-07 장태순 고분자 수용성 키토산의 고지방 식이에 의한 체 지방 증가억제 효과
KR20010085046A (ko) * 2001-07-25 2001-09-07 장태순 비만생쥐의 난소반응과 임신에서 고분자 수용성 키토산의효과
US6323189B1 (en) 1998-07-30 2001-11-27 E-Nutriceuticals, Inc. Chitosan-containing liquid compositions and methods for their preparation and use
WO2002085142A1 (fr) * 2001-04-25 2002-10-31 Oy Finnsoypro Ltd Aliment fonctionnel comprenant du chitosane microcristallin et des proteines de soja, procede de preparation correspondant
WO2004068971A1 (fr) * 2003-02-06 2004-08-19 Advanced Biopolymers As Produit alimentaire au chitosane
WO2004105516A1 (fr) * 2003-05-28 2004-12-09 Nutrinova Aliments dietetiques pour une alimentation visant a controler voire reduire le poids
WO2007068076A1 (fr) * 2005-12-16 2007-06-21 Dnp Canada Inc. Dérivés de chitine contre l'hyperlipémie

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060058261A1 (en) * 2004-09-15 2006-03-16 Andre Aube Chitin derivatives for hyperlipidemia

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4223023A (en) * 1978-10-12 1980-09-16 Ivan Furda Nonabsorbable lipid binder
EP0219156A1 (fr) * 1985-09-26 1987-04-22 Tofco S.A. Composition tempérant l'appétit et ayant une activité anti-gastrite
WO1991000298A1 (fr) * 1989-06-30 1991-01-10 Firextra Oy Methode pour la fabrication continue de chitosan microcristallin
US5654001A (en) * 1992-03-24 1997-08-05 Kirin Beer Kabushiki Kaisha Dietary lipid digestion-absorption inhibitory agents and ingesta

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4223023A (en) * 1978-10-12 1980-09-16 Ivan Furda Nonabsorbable lipid binder
EP0219156A1 (fr) * 1985-09-26 1987-04-22 Tofco S.A. Composition tempérant l'appétit et ayant une activité anti-gastrite
WO1991000298A1 (fr) * 1989-06-30 1991-01-10 Firextra Oy Methode pour la fabrication continue de chitosan microcristallin
US5654001A (en) * 1992-03-24 1997-08-05 Kirin Beer Kabushiki Kaisha Dietary lipid digestion-absorption inhibitory agents and ingesta

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PROC. INT. CONF. CHITIN CHITOSAN, 6th, 1994, STRUSZCZYK HENRYK et al., "Present State and Forecast of Microcrystalline Chitosan", pages 594-599. *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999036075A1 (fr) * 1998-01-17 1999-07-22 West Pharmaceutical Services Drug Delivery & Clinical Research Centre Limited Composition orale absorbant l'huile
US6323189B1 (en) 1998-07-30 2001-11-27 E-Nutriceuticals, Inc. Chitosan-containing liquid compositions and methods for their preparation and use
WO2000024785A1 (fr) * 1998-10-23 2000-05-04 Novasso Oy Substance utilisee pour la reduction du taux de cholesterol et de lipides
WO2002085142A1 (fr) * 2001-04-25 2002-10-31 Oy Finnsoypro Ltd Aliment fonctionnel comprenant du chitosane microcristallin et des proteines de soja, procede de preparation correspondant
KR20010085047A (ko) * 2001-07-25 2001-09-07 장태순 고분자 수용성 키토산의 고지방 식이에 의한 체 지방 증가억제 효과
KR20010085046A (ko) * 2001-07-25 2001-09-07 장태순 비만생쥐의 난소반응과 임신에서 고분자 수용성 키토산의효과
WO2004068971A1 (fr) * 2003-02-06 2004-08-19 Advanced Biopolymers As Produit alimentaire au chitosane
WO2004105516A1 (fr) * 2003-05-28 2004-12-09 Nutrinova Aliments dietetiques pour une alimentation visant a controler voire reduire le poids
WO2007068076A1 (fr) * 2005-12-16 2007-06-21 Dnp Canada Inc. Dérivés de chitine contre l'hyperlipémie

Also Published As

Publication number Publication date
AU5989098A (en) 1998-08-26
FI970499A0 (fi) 1997-02-06
JP2001512432A (ja) 2001-08-21
FI970499L (fi) 1998-08-07
FI107432B (fi) 2001-08-15
EP1014997A1 (fr) 2000-07-05
CA2280507A1 (fr) 1998-08-13

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